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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (60)transporters (2) Show 62 proteins XML

enzymes (60)transporters (2) Show 62 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:41:25 UTC

HMDB ID

HMDB0000145

Secondary Accession Numbers

HMDB0004449
HMDB00145
HMDB04449

Metabolite Identification

Common Name

Estrone

Description

Estrone is a major mammalian estrogen. The conversion of the natural C19 steroids, testosterone and androstenedione into estrone is dependent on a complex key reaction catalyzed by the cytochrome P450 aromatase (EC 1.14.14.1, unspecific monooxygenase), which is expressed in many tissues of the adult human (e.g. ovary, fat tissue), but not in the liver. The ovaries after menopause continue to produce androstenedione and testosterone in significant amounts and these androgens are converted in fat, muscle, and skin into estrone. When women between the ages of 45 and 64 years have prophylactic oophorectomy (when hysterectomy is performed for benign disease to prevent the development of ovarian cancer), evidence suggests that oophorectomy increases the subsequent risk of coronary heart disease (CHD) and osteoporosis. Whereas 14,000 women die of ovarian cancer every year nearly 490,000 women die of heart disease and 48,000 women die within 1 year after hip fracture. Therefore, the decision to perform prophylactic oophorectomy should be approached with great caution for the majority of women who are at low risk of developing ovarian cancer. Steroid sulfatase (EC 3.1.6.2, STS) hydrolyzes steroid sulfates, such as estrone sulfate to estrone which can be converted to steroids with potent estrogenic properties, that is, estradiol; STS activity is much higher in breast tumors and high levels of STS mRNA expression in tumors are associated with a poor prognosis. The biological roles of estrogens in tumorigenesis are certainly different between the endometrium and breast, although both are considered "estrogen-dependent tissues". 17beta-hydroxysteroid dehydrogenases (EC 1.1.1.62, 17-HSDs) are enzymes involved in the formation of active sex steroids. estrone is interconverted by two enzymes 17-HSD types. Type 1 converts estrone to estradiol and Type 2 catalyzes the reverse reaction. (PMID: 17653961 , 17513923 , 17470679 , 17464097 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000145
     RDKit          3D
Estrone
 42 45  0  0  0  0  0  0  0  0999 V2000
   -2.4507   -0.5081    1.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688   -0.7693    0.2945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4724   -1.9846    0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0372   -1.8188   -0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4582   -0.4674   -0.5702 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9112   -0.2898   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7331   -1.3689   -0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1032   -1.3188   -0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6531   -0.1422    0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0359   -0.0339    0.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8263    0.9413    0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4623    0.8859    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6194    2.0889    0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2899    1.9703   -0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3464    0.6585    0.0993 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7086    0.4491   -0.4120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7368    1.4652   -0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0294    0.6604   -0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6284   -0.7660   -0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2643   -1.7118   -0.6255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5048   -0.5144    2.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0253   -1.4059    2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0976    0.3544    1.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5683   -2.6410    0.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981   -2.5892   -0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2267   -2.5095   -1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129   -2.2068    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3109   -0.2918   -1.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3511   -2.3230   -0.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7435   -2.1691   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3381   -0.2918    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2439    1.8818    0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4140    2.1096    1.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1419    3.0224    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4461    2.0060   -1.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246    2.8274    0.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269    0.5735    1.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6998    0.2039   -1.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6650    2.2630   -0.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7170    1.9745    0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3575    0.8387   -1.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7938    0.9471    0.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 16  2  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  7 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  1
 16 38  1  6
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
M  END


  Mrv1652310301918522D          

 23 26  0  0  0  0            999 V2000
10001.446810001.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1679 9998.1252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.0195 9998.9603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.731110000.1943    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.4468 9998.9603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0192 9999.7809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.0192 9998.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7337 9998.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7337 9999.3684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.732510001.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.018010000.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5939 9999.7799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8795 9999.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8795 9998.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5939 9998.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3084 9998.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3084 9999.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.231610000.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.447010000.6136    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.4470 9999.7886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.2316 9999.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.716510000.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.486510001.6532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11  6  1  0  0  0  0
  6  3  1  6  0  0  0
  9  4  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 12  1  0  0  0  0
 14  2  1  0  0  0  0
  6 17  1  0  0  0  0
 16  7  1  0  0  0  0
 18 19  1  0  0  0  0
 18 22  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  2  0  0  0  0
 20  5  1  6  0  0  0
  9 20  1  0  0  0  0
 10 19  1  0  0  0  0
 19  1  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0000145

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1

> <INCHI_KEY>
DNXHEGUUPJUMQT-CBZIJGRNSA-N

> <FORMULA>
C18H22O2

> <MOLECULAR_WEIGHT>
270.3661

> <EXACT_MASS>
270.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.24404121393373

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

> <ALOGPS_LOGP>
4.03

> <JCHEM_LOGP>
4.309029034000001

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.957534565528498

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.32695754200012

> <JCHEM_PKA_STRONGEST_BASIC>
-5.448299376893847

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
79.0824

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.94e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000145
     RDKit          3D
Estrone
 42 45  0  0  0  0  0  0  0  0999 V2000
   -2.4507   -0.5081    1.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688   -0.7693    0.2945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4724   -1.9846    0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0372   -1.8188   -0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4582   -0.4674   -0.5702 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9112   -0.2898   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7331   -1.3689   -0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1032   -1.3188   -0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6531   -0.1422    0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0359   -0.0339    0.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8263    0.9413    0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4623    0.8859    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6194    2.0889    0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2899    1.9703   -0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3464    0.6585    0.0993 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7086    0.4491   -0.4120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7368    1.4652   -0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0294    0.6604   -0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6284   -0.7660   -0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2643   -1.7118   -0.6255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5048   -0.5144    2.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0253   -1.4059    2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0976    0.3544    1.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5683   -2.6410    0.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981   -2.5892   -0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2267   -2.5095   -1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129   -2.2068    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3109   -0.2918   -1.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3511   -2.3230   -0.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7435   -2.1691   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3381   -0.2918    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2439    1.8818    0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4140    2.1096    1.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1419    3.0224    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4461    2.0060   -1.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246    2.8274    0.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269    0.5735    1.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6998    0.2039   -1.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6650    2.2630   -0.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7170    1.9745    0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3575    0.8387   -1.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7938    0.9471    0.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 16  2  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  7 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  1
 16 38  1  6
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
M  END

HEADER    PROTEIN                                 30-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-OCT-19         0                                  
HETATM    1  C   UNK     0    8669.3678669.359   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8661.3808663.167   0.000  0.00  0.00           O+0
HETATM    3  H   UNK     0    8666.7038664.726   0.000  0.00  0.00           H+0
HETATM    4  H   UNK     0    8668.0318667.029   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8669.3678664.726   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0    8666.7038666.258   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8666.7038663.178   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8668.0368663.947   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8668.0368665.488   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.0348668.582   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8666.7008667.812   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.0428666.256   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.7088665.486   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.7088663.946   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.0428663.176   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.3768663.946   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.3768665.486   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8670.8328668.288   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8669.3688667.812   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8669.3688666.272   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8670.8328665.796   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8671.7378667.042   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8671.3088669.753   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   14                                                            
CONECT    3    6                                                            
CONECT    4    9                                                            
CONECT    5   20                                                            
CONECT    6    9   11    3   17                                             
CONECT    7    8   16                                                       
CONECT    8    7    9                                                       
CONECT    9    6    8    4   20                                             
CONECT   10   11   19                                                       
CONECT   11   10    6                                                       
CONECT   12   13   17                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15    2                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17    7                                                  
CONECT   17   16   12    6                                                  
CONECT   18   19   22   23                                                  
CONECT   19   18   20   10    1                                             
CONECT   20   19   21    5    9                                             
CONECT   21   20   22                                                       
CONECT   22   18   21                                                       
CONECT   23   18                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0000145
HETATM    1  C1  UNL     1      -2.451  -0.508   1.787  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.269  -0.769   0.294  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.472  -1.985   0.055  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.037  -1.819  -0.232  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.458  -0.467  -0.570  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.911  -0.290  -0.313  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.733  -1.369  -0.557  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.103  -1.319  -0.353  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.653  -0.142   0.110  1.00  0.00           C  
HETATM   10  O1  UNL     1       6.036  -0.034   0.335  1.00  0.00           O  
HETATM   11  C10 UNL     1       3.826   0.941   0.355  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.462   0.886   0.150  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.619   2.089   0.432  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.290   1.970  -0.322  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.346   0.659   0.099  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.709   0.449  -0.412  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.737   1.465  -0.154  1.00  0.00           C  
HETATM   18  C17 UNL     1      -4.029   0.660  -0.368  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.628  -0.766  -0.290  1.00  0.00           C  
HETATM   20  O2  UNL     1      -4.264  -1.712  -0.626  1.00  0.00           O  
HETATM   21  H1  UNL     1      -1.505  -0.514   2.337  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.025  -1.406   2.163  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.098   0.354   1.982  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.568  -2.641   0.973  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.998  -2.589  -0.744  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.227  -2.509  -1.089  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.613  -2.207   0.610  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.311  -0.292  -1.660  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.351  -2.323  -0.924  1.00  0.00           H  
HETATM   30  H10 UNL     1       4.744  -2.169  -0.547  1.00  0.00           H  
HETATM   31  H11 UNL     1       6.338  -0.292   1.285  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.244   1.882   0.723  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.414   2.110   1.516  1.00  0.00           H  
HETATM   34  H14 UNL     1       2.142   3.022   0.166  1.00  0.00           H  
HETATM   35  H15 UNL     1       0.446   2.006  -1.401  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.325   2.827   0.018  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.227   0.574   1.179  1.00  0.00           H  
HETATM   38  H18 UNL     1      -1.700   0.204  -1.496  1.00  0.00           H  
HETATM   39  H19 UNL     1      -2.665   2.263  -0.946  1.00  0.00           H  
HETATM   40  H20 UNL     1      -2.717   1.975   0.804  1.00  0.00           H  
HETATM   41  H21 UNL     1      -4.358   0.839  -1.429  1.00  0.00           H  
HETATM   42  H22 UNL     1      -4.794   0.947   0.364  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   16   19
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   15   28
CONECT    6    7    7   12
CONECT    7    8   29
CONECT    8    9    9   30
CONECT    9   10   11
CONECT   10   31
CONECT   11   12   12   32
CONECT   12   13
CONECT   13   14   33   34
CONECT   14   15   35   36
CONECT   15   16   37
CONECT   16   17   38
CONECT   17   18   39   40
CONECT   18   19   41   42
CONECT   19   20   20
END

HMDB0000145
     RDKit          3D
Estrone
 42 45  0  0  0  0  0  0  0  0999 V2000
   -2.4507   -0.5081    1.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688   -0.7693    0.2945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4724   -1.9846    0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0372   -1.8188   -0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4582   -0.4674   -0.5702 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9112   -0.2898   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7331   -1.3689   -0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1032   -1.3188   -0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6531   -0.1422    0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0359   -0.0339    0.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8263    0.9413    0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4623    0.8859    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6194    2.0889    0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2899    1.9703   -0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3464    0.6585    0.0993 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7086    0.4491   -0.4120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7368    1.4652   -0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0294    0.6604   -0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6284   -0.7660   -0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2643   -1.7118   -0.6255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5048   -0.5144    2.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0253   -1.4059    2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0976    0.3544    1.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5683   -2.6410    0.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981   -2.5892   -0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2267   -2.5095   -1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129   -2.2068    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3109   -0.2918   -1.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3511   -2.3230   -0.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7435   -2.1691   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3381   -0.2918    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2439    1.8818    0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4140    2.1096    1.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1419    3.0224    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4461    2.0060   -1.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246    2.8274    0.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269    0.5735    1.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6998    0.2039   -1.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6650    2.2630   -0.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7170    1.9745    0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3575    0.8387   -1.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7938    0.9471    0.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 16  2  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  7 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  1
 16 38  1  6
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxy-1,3,5(10)-estratrien-17-one	ChEBI
Follicular hormone	ChEBI
Folliculin	ChEBI
Oestrone	ChEBI
(+)-Estrone	HMDB
1,3,5(10)-Estratrien-3-ol-17-one	HMDB
3-Hydroxy-17-keto-estra-1,3,5-triene	HMDB
3-Hydroxyestra-1,3,5(10)-trien-17-one	HMDB
3-Hydroxyestra-1,3,5(10)-triene-17-one	HMDB
3-Hydroxyoestra-1,3,5(10)-trien-17-one	HMDB
D1,3,5(10)-Estratrien-3-ol-17-one	HMDB
Estrone, (+-)-isomer	HMDB
Hyrex brand OF estrone	HMDB
Estrone, (9 beta)-isomer	HMDB
Estrovarin	HMDB
Kestrone	HMDB
Wehgen	HMDB
Estrone, (8 alpha)-isomer	HMDB
Hauck brand OF estrone	HMDB
Unigen	HMDB
Vortech brand OF estrone	HMDB

Chemical Formula

C₁₈H₂₂O₂

Average Molecular Weight

270.3661

Monoisotopic Molecular Weight

270.161979948

IUPAC Name

(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

Traditional Name

(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

CAS Registry Number

53-16-7

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3

InChI Identifier

InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1

InChI Key

DNXHEGUUPJUMQT-CBZIJGRNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrogens and derivatives

Alternative Parents

Substituents

Estrogen-skeleton
3-hydroxysteroid
Hydroxysteroid
17-oxosteroid
Oxosteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Ketone
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

17-oxo steroid (CHEBI:17263 )
3-hydroxy steroid (CHEBI:17263 )
estrane (C00468 )
C18 steroids (estrogens) and derivatives (C00468 )
Estrane and derivatives (C00468 )
Estrogens (C00468 )
C18 steroids (estrogens) and derivatives (LMST02010004 )

Ontology

Physiological effect

Health effect

Observation

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Mood disorder

Major depressive disorder (HMDB: HMDB0000145)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 6460495)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0000145)
Mitochondrion (HMDB: HMDB0000145)

Organ

Excreta

Biofluid or Excreta

Urine (PMID: 8478958)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000145)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000145)

Source

Exogenous

Exogenous (HMDB: HMDB0000145)

Food

Food (HMDB: HMDB0000145)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Endogenous

Endogenous (HMDB: HMDB0000145)

Plant

Animal

Animal (HMDB: HMDB0000145)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Androgen and Estrogen Metabolism (HMDB: HMDB0000145)
Sulfate/Sulfite Metabolism (HMDB: HMDB0000145)
Androstenedione Metabolism (HMDB: HMDB0000145)
Androstenedione Metabolism (PathBank: SMP0087421)
Estrone Metabolism (PathBank: SMP0087272)

Disease pathway

17-beta Hydroxysteroid Dehydrogenase III Deficiency (PathBank: SMP0120437)
Aromatase Deficiency (PathBank: SMP0120848)
Sulfite Oxidase Deficiency (PathBank: SMP0120816)

Lipid metabolism pathway (HMDB: HMDB0000145)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000145)

Cellular process

Cell signaling (HMDB: HMDB0000145)

Biochemical process

Lipid transport (HMDB: HMDB0000145)

System process

Reproduction (HMDB: HMDB0000145)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000145)
Anti impotence (HMDB: HMDB0000145)
Anti menopausal (HMDB: HMDB0000145)
Anti prostat adenomic (HMDB: HMDB0000145)
Anti vaginitic (HMDB: HMDB0000145)
Aphrodisiac (HMDB: HMDB0000145)
Carcinogenic (HMDB: HMDB0000145)
Estrogenic (HMDB: HMDB0000145)
Transdermal (HMDB: HMDB0000145)

Molecular messenger

Signaling molecule (HMDB: HMDB0000145)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000145)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000145)

Biomarker

X-Linked Ichthyosis (MarkerDB: MDB00000069)
Menstrual Cycle (MarkerDB: MDB00000069)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	258 - 260 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.03 mg/mL	Not Available
LogP	3.13	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	170.629	30932474
[M+H]+	MetCCS_train_pos	164.305	30932474
[M-H]-	Not Available	170.629	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000181
[M+H]+	Not Available	164.583	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000181

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0039 g/L	ALOGPS
logP	4.03	ALOGPS
logP	4.31	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.08 m³·mol⁻¹	ChemAxon
Polarizability	31.24 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	164.272	31661259
DarkChem	[M-H]-	162.184	31661259
AllCCS	[M+H]+	166.571	32859911
AllCCS	[M-H]-	173.791	32859911
DeepCCS	[M-2H]-	211.545	30932474
DeepCCS	[M+Na]+	186.127	30932474
AllCCS	[M+H]+	166.6	32859911
AllCCS	[M+H-H2O]+	163.2	32859911
AllCCS	[M+NH4]+	169.7	32859911
AllCCS	[M+Na]+	170.6	32859911
AllCCS	[M-H]-	173.8	32859911
AllCCS	[M+Na-2H]-	173.5	32859911
AllCCS	[M+HCOO]-	173.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.16 minutes	32390414
Predicted by Siyang on May 30, 2022	15.2423 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.59 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2300.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	418.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	197.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	202.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	478.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	673.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	656.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	86.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1352.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	478.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1434.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	400.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	416.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	292.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	273.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	28.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Estrone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	3277.3	Standard polar	33892256
Estrone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	2661.4	Standard non polar	33892256
Estrone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	2707.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Estrone,1TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CCC2=O	2664.0	Semi standard non polar	33892256
Estrone,1TMS,isomer #2	C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	2640.1	Semi standard non polar	33892256
Estrone,2TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	2674.5	Semi standard non polar	33892256
Estrone,2TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	2497.6	Standard non polar	33892256
Estrone,2TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	2830.9	Standard polar	33892256
Estrone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12	2950.6	Semi standard non polar	33892256
Estrone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@]12C	2913.0	Semi standard non polar	33892256
Estrone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]12C	3214.9	Semi standard non polar	33892256
Estrone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]12C	2910.8	Standard non polar	33892256
Estrone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]12C	3083.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Estrone GC-MS (1 TMS)	splash10-05ox-3951000000-8bc438f505b3cf49b21f	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Estrone GC-MS (1 MEOX; 1 TMS)	splash10-003u-4942000000-a72ea34d85d9d524c247	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Estrone GC-MS (1 MEOX; 1 TMS)	splash10-0019-8931000000-aad9803af812c7c40f53	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Estrone EI-B (Non-derivatized)	splash10-00di-2940000000-2d417e7ecb4a8b87b817	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Estrone EI-B (Non-derivatized)	splash10-00di-0980000000-5b293db89a0f2efeb784	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Estrone GC-MS (Non-derivatized)	splash10-05ox-3951000000-8bc438f505b3cf49b21f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Estrone GC-MS (Non-derivatized)	splash10-003u-4942000000-a72ea34d85d9d524c247	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Estrone GC-MS (Non-derivatized)	splash10-0019-8931000000-aad9803af812c7c40f53	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estrone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0adl-1970000000-871531490fb22b8fe12f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estrone GC-MS (1 TMS) - 70eV, Positive	splash10-009t-1093000000-a8d755d13e3b819514c8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estrone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estrone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estrone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Estrone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-2930000000-c99df908474247066a2b	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00di-0190000000-071e67516e11357ff64e	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a4j-4910000000-20e059a7c508ba492af3	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-067i-9700000000-9ff5214f08822f238fa9	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone EI-B (HITACHI M-80) , Positive-QTOF	splash10-00di-2940000000-3b9744c27d6a3d2eff6e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone LC-ESI-qTof , Positive-QTOF	splash10-0ukc-2690000000-7afb48e267c7b334213b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone Linear Ion Trap , negative-QTOF	splash10-014i-0690000000-a76244de959b06ec896e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone LC-ESI-ITFT , positive-QTOF	splash10-0a59-0910000000-4a1bc1cbc90c3e5281e6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone LC-ESI-ITFT , positive-QTOF	splash10-0a59-0900000000-0830d4ad43804976f508	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone LC-ESI-ITFT , positive-QTOF	splash10-0udi-0390000000-41440e74b3f0b5f365d7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone LC-ESI-ITFT , positive-QTOF	splash10-0udi-0390000000-fdc0255246e3a9013d0a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone , positive-QTOF	splash10-0a59-2910000000-fc5173d435c3c7fc603c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone LC-ESI-QFT , positive-QTOF	splash10-00di-0390000000-25cecb1c4785e7bffd56	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone 35V, Positive-QTOF	splash10-0pb9-0930000000-d947dbed0baa600d21a1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone 10V, Positive-QTOF	splash10-00di-0190000000-38b40bed2e5c895d292f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone 20V, Positive-QTOF	splash10-0pc0-0920000000-391eea72f6dda0eaa3c2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone 45V, Negative-QTOF	splash10-0159-0900000000-350b322964f2315bf505	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone 30V, Negative-QTOF	splash10-014i-0690000000-277d92852a8f35c82f11	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone 40V, Negative-QTOF	splash10-0002-0910000000-db57c4d24dab84acfe27	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Estrone 60V, Negative-QTOF	splash10-014i-0900000000-61f2965f743c194d4628	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone 10V, Positive-QTOF	splash10-00di-0190000000-64cf013a5b0ad5e8bf56	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone 20V, Positive-QTOF	splash10-00fr-0590000000-40418c285df2157226dc	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone 40V, Positive-QTOF	splash10-0fb9-6980000000-724c68b368fbe3d38f5e	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone 10V, Negative-QTOF	splash10-014i-0090000000-6778bd7122813b501c1e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone 20V, Negative-QTOF	splash10-014i-0090000000-0f2e0b96bc30b346c581	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrone 40V, Negative-QTOF	splash10-0f9i-1090000000-9ccbd9f351dd1f8e52cb	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	2012-12-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver
Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Sulfur metabolism	Not Available
Androgen and Estrogen Metabolism
Sulfite oxidase deficiency		Not Available
17-Beta Hydroxysteroid Dehydrogenase III Deficiency		Not Available
Aromatase deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00020 (0.00011-0.00030) uM	Adult (>18 years old)	Male	Normal	The Merck Manual,...	details
Blood	Detected and Quantified	0.00012 (0.0-0.00024) uM	Adult (>18 years old)	Female	Normal	The Merck Manual,...	details
Blood	Detected and Quantified	0.00017 +/- 0.000071 uM	Adult (>18 years old)	Female	Normal	8478958	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.0013 +/- 0.00085 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	8478958	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00035 (0.00014-0.00056) uM	Adult (>18 years old)	Female	Menstrual cycle (follicular phase)	The Merck Manual,...	details
Blood	Detected and Quantified	0.00050 (0.00028-0.00074) uM	Adult (>18 years old)	Female	Menstrual cycle (midcycle)	The Merck Manual,...	details
Blood	Detected and Quantified	0.00030 (0.00018-0.00042) uM	Adult (>18 years old)	Female	Menstrual cycle (luteal phase)	The Merck Manual,...	details
Blood	Detected and Quantified	0.00022 (0.00013-0.00038) uM	Adult (>18 years old)	Male	Severe coronary artery disease	6460495	details
Blood	Detected and Quantified	0.00021 (0.00011-0.00037) uM	Adult (>18 years old)	Both	Minor electrocardiongraphic abnormalities and/or arrhythmia with negative coronary arteriograms	6460495	details
Blood	Detected and Quantified	<0.00004 uM	Children (1-13 years old)	Female	Aromatase deficiency	9177373	details
Blood	Detected and Quantified	0.000111-0.000318 uM	Adult (>18 years old)	Male	X-linked ichthyosis	3864567	details

Associated Disorders and Diseases

Disease References

Menstrual cycle
(). The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.. .
Aromatase deficiency
Mullis PE, Yoshimura N, Kuhlmann B, Lippuner K, Jaeger P, Harada H: Aromatase deficiency in a female who is compound heterozygote for two new point mutations in the P450arom gene: impact of estrogens on hypergonadotropic hypogonadism, multicystic ovaries, and bone densitometry in childhood. J Clin Endocrinol Metab. 1997 Jun;82(6):1739-45. doi: 10.1210/jcem.82.6.3994. [PubMed:9177373 ]
X-linked ichthyosis
Lykkesfeldt G, Bennett P, Lykkesfeldt AE, Micic S, Moller S, Svenstrup B: Abnormal androgen and oestrogen metabolism in men with steroid sulphatase deficiency and recessive X-linked ichthyosis. Clin Endocrinol (Oxf). 1985 Oct;23(4):385-93. [PubMed:3864567 ]

Associated OMIM IDs

613546 (Aromatase deficiency)
308100 (X-linked ichthyosis)

External Links

DrugBank ID

DB00655

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17263

Food Biomarker Ontology

Not Available

VMH ID

ESTRONE

MarkerDB ID

MDB00000069

Good Scents ID

Not Available

References

Synthesis Reference

Kocovsky, Paved; Baines, Richard S. Synthesis of estrone via a thallium(III)-mediated fragmentation of a 19-hydroxyandrost-5-ene precursor. Tetrahedron Letters (1993), 34(38), 6139-40.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Pfeiffer E, Graf E, Gerstner S, Metzler M: Stimulation of estradiol glucuronidation: a protective mechanism against estradiol-mediated carcinogenesis? Mol Nutr Food Res. 2006 Apr;50(4-5):385-9. [PubMed:16598814 ]
Czernik PJ, Little JM, Barone GW, Raufman JP, Radominska-Pandya A: Glucuronidation of estrogens and retinoic acid and expression of UDP-glucuronosyltransferase 2B7 in human intestinal mucosa. Drug Metab Dispos. 2000 Oct;28(10):1210-6. [PubMed:10997942 ]
Kuhl H, Wiegratz I: Can 19-nortestosterone derivatives be aromatized in the liver of adult humans? Are there clinical implications? Climacteric. 2007 Aug;10(4):344-53. [PubMed:17653961 ]
Parker WH, Broder MS, Liu Z, Shoupe D, Farquhar C, Berek JS: Ovarian conservation at the time of hysterectomy for benign disease. Clin Obstet Gynecol. 2007 Jun;50(2):354-61. [PubMed:17513923 ]
Stanway SJ, Delavault P, Purohit A, Woo LW, Thurieau C, Potter BV, Reed MJ: Steroid sulfatase: a new target for the endocrine therapy of breast cancer. Oncologist. 2007 Apr;12(4):370-4. [PubMed:17470679 ]
Ito K: Hormone replacement therapy and cancers: the biological roles of estrogen and progestin in tumorigenesis are different between the endometrium and breast. Tohoku J Exp Med. 2007 May;212(1):1-12. [PubMed:17464097 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 62 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Arylsulfatase D

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: ARSD
Uniprot ID:: P51689
Molecular weight:: 64859.3

Enzyme Details

2. Arylsulfatase E

General function:: Involved in catalytic activity
Specific function:: May be essential for the correct composition of cartilage and bone matrix during development. Has no activity toward steroid sulfates
Gene Name:: ARSE
Uniprot ID:: P51690
Molecular weight:: 65668.4

Enzyme Details

3. Estrogen sulfotransferase

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of estradiol and estrone. May play a role in the regulation of estrogen receptor activity by metabolizing free estradiol. Maximally sulfates beta-estradiol and estrone at concentrations of 20 nM. Also sulfates dehydroepiandrosterone, pregnenolone, ethinylestradiol, equalenin, diethylstilbesterol and 1-naphthol, at significantly higher concentrations; however, cortisol, testosterone and dopamine are not sulfated.
Gene Name:: SULT1E1
Uniprot ID:: P49888
Molecular weight:: 35126.185

Reactions

Phosphoadenosine phosphosulfate + Estrone → Adenosine 3',5'-diphosphate + Estrone sulfate	details

Enzyme Details

4. Estradiol 17-beta-dehydrogenase 2

General function:: Involved in oxidoreductase activity
Specific function:: Capable of catalyzing the interconversion of testosterone and androstenedione, as well as estradiol and estrone. Also has 20-alpha-HSD activity. Uses NADH while EDH17B3 uses NADPH.
Gene Name:: HSD17B2
Uniprot ID:: P37059
Molecular weight:: 42784.75

Reactions

Estradiol + NAD(P)(+) → Estrone + NAD(P)H	details
Estradiol + NAD → Estrone + NADH + Hydrogen Ion	details
Estradiol + NADP → Estrone + NADPH + Hydrogen Ion	details

Enzyme Details

5. UDP-glucuronosyltransferase 2B28

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:: UGT2B28
Uniprot ID:: Q9BY64
Molecular weight:: 38742.9

Reactions

Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

6. Estradiol 17-beta-dehydrogenase 8

General function:: Involved in oxidoreductase activity
Specific function:: NAD-dependent 17-beta-hydroxysteroid dehydrogenase with highest activity towards estradiol. Has very low activity towards testosterone. The heteroteramer with CBR4 has NADH-dependent 3-ketoacyl-acyl carrier protein reductase activity. May play a role in biosynthesis of fatty acids in mitochondria.
Gene Name:: HSD17B8
Uniprot ID:: Q92506
Molecular weight:: 26973.56

Reactions

Estradiol + NAD(P)(+) → Estrone + NAD(P)H	details
Estradiol + NAD → Estrone + NADH + Hydrogen Ion	details
Estradiol + NADP → Estrone + NADPH + Hydrogen Ion	details

Enzyme Details

7. UDP-glucuronosyltransferase 2B4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:: UGT2B4
Uniprot ID:: P06133
Molecular weight:: 60512.035

Reactions

Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

8. UDP-glucuronosyltransferase 1-4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:: UGT1A4
Uniprot ID:: P22310
Molecular weight:: 60024.535

Reactions

Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

9. UDP-glucuronosyltransferase 2B10

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT2B10
Uniprot ID:: P36537
Molecular weight:: 60773.485

Reactions

Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

10. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

Reactions

Estrone + Uridine diphosphate glucuronic acid → Estrone glucuronide + Uridine 5'-diphosphate	details

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:: SLCO1B1
Uniprot ID:: Q9Y6L6
Molecular weight:: 76448.0

Enzyme Details

2. Solute carrier family 22 member 7

General function:: Involved in transmembrane transport
Specific function:: Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:: SLC22A7
Uniprot ID:: Q9Y694
Molecular weight:: 60025.0

Only showing the first 10 proteins. There are 62 proteins in total.

Show all enzymes and transporters

Showing metabocard for Estrone (HMDB0000145)

MOL for HMDB0000145 (Estrone)

3D MOL for HMDB0000145 (Estrone)

3D SDF for HMDB0000145 (Estrone)

3D-SDF for HMDB0000145 (Estrone)

PDB for HMDB0000145 (Estrone)

3D PDB for HMDB0000145 (Estrone)

SMILES for HMDB0000145 (Estrone)

INCHI for HMDB0000145 (Estrone)

Structure for HMDB0000145 (Estrone)

3D Structure for HMDB0000145 (Estrone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

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Transporters