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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:02 UTC

HMDB ID

HMDB0000429

Secondary Accession Numbers

HMDB00429

Metabolite Identification

Common Name

17alpha-Estradiol

Description

17alpha-Estradiol (also known as 17alpha-E2, 17-epiestradiol) belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, epiestriol is considered to be a steroid molecule. 17alpha-Estradiol is also classified as an estradiol. Specifically, estradiols are characterized by an estra-1,3,5(10)-triene substituted by hydroxy groups at positions 3 and 17. 17alpha-Estradiol is considered as a 17alpha-hydroxy steroid and a 3-hydroxy steroid. 17alpha-Estradiol is a weak endogenous steroidal estrogen that is related to 17beta-estradiol. 17beta-estradiol is better known simply as estradiol or E2 (PMID: 16728493 ). Therefore, 17alpha-Estradiol is the C17 alpha epimer of 17beta-estradiol (PMID: 16728493 ). 17alpha-Estradiol is found in all vertebrates. It has approximately 100-fold lower estrogenic potency than 17beta-estradiol. 17alpha-estradiol is a non-feminizing estrogen with significantly reduced binding affinity for the classic estrogen receptors ERalpha and ERbeta. Although 17alpha-estradiol is far weaker than 17beta-estradiol as an agonist of the nuclear estrogen receptors, it has been found to bind to and activate the brain-expressed ER-X with a greater potency than that of 17beta-estradiol. 17alpha-Estradiol is a potent 5-alpha reductase inhibitor that has been shown to improve metabolic function, enhance insulin sensitivity, and reduce fat and inflammation in older lab animals without causing feminization (PMID: 26809497 ). It has also been shown that 17alpha-Estradiol also increases AMPK levels and reduced mTOR activity in visceral adipose tissue (PMID: 26809497 ).

Structure

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

HMDB0000429
     RDKit          3D
17alpha-Estradiol
 44 47  0  0  0  0  0  0  0  0999 V2000
   -2.1765    1.9777    0.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1399    0.5640    0.6965 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3563    0.4055    1.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1118    0.5640    1.7709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6582   -0.2295    0.6232 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0858   -0.1391    0.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9256    0.2084    1.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3124    0.2922    1.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8518    0.0242    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2130    0.1003   -0.1676 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0155   -0.3290   -1.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6530   -0.4037   -0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -0.7851   -1.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.2648   -1.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453    0.1306   -0.6041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5175   -0.3933   -0.3326 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4818   -0.3359   -1.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8227   -0.1626   -0.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5268    0.0318    0.7348 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6013   -1.2165    1.3492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3706    2.6057    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087    1.9463   -0.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1633    2.4116    0.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285   -0.5750    2.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7050    1.1796    2.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5872    0.2977    2.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3419    1.6447    1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4043   -1.3092    0.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5953    0.4376    2.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9775    0.5631    2.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7942   -0.7025   -0.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4891   -0.5308   -1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143   -0.3902   -2.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324   -1.9012   -2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473   -1.0781   -2.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960    0.5580   -2.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2171    1.2590   -0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -1.3797    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5177   -1.3494   -1.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2908    0.3911   -2.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2786    0.7632   -1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4851   -1.0388   -0.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2691    0.7448    1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1661   -1.8550    0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  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  1  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  1
  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  6
 16 38  1  1
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  1
 20 44  1  0
M  END

17a-Estradiol.mol
  Mrv1652304202019422D          

 23 26  0  0  0  0            999 V2000
   -2.0637   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7782   -1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -0.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -0.5198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5086   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2933   -0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7782    0.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933    0.9727    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5482    1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086    0.7177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5086    1.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    1.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    0.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6348   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    0.3052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  1  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  0  0  0  0
  6 20  2  0  0  0  0
 19 21  1  6  0  0  0
  9 22  1  1  0  0  0
 10 23  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000429

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17-,18+/m1/s1

> <INCHI_KEY>
VOXZDWNPVJITMN-SFFUCWETSA-N

> <FORMULA>
C18H24O2

> <MOLECULAR_WEIGHT>
272.382

> <EXACT_MASS>
272.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.927942457761795

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
3.745501328333334

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.37769223665565

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.327060716263132

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8839974156894889

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
79.90469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.13e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000429
     RDKit          3D
17alpha-Estradiol
 44 47  0  0  0  0  0  0  0  0999 V2000
   -2.1765    1.9777    0.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1399    0.5640    0.6965 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3563    0.4055    1.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1118    0.5640    1.7709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6582   -0.2295    0.6232 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0858   -0.1391    0.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9256    0.2084    1.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3124    0.2922    1.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8518    0.0242    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2130    0.1003   -0.1676 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0155   -0.3290   -1.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6530   -0.4037   -0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -0.7851   -1.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.2648   -1.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453    0.1306   -0.6041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5175   -0.3933   -0.3326 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4818   -0.3359   -1.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8227   -0.1626   -0.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5268    0.0318    0.7348 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6013   -1.2165    1.3492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3706    2.6057    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087    1.9463   -0.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1633    2.4116    0.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285   -0.5750    2.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7050    1.1796    2.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5872    0.2977    2.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3419    1.6447    1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4043   -1.3092    0.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5953    0.4376    2.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9775    0.5631    2.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7942   -0.7025   -0.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4891   -0.5308   -1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143   -0.3902   -2.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324   -1.9012   -2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473   -1.0781   -2.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960    0.5580   -2.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2171    1.2590   -0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -1.3797    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5177   -1.3494   -1.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2908    0.3911   -2.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2786    0.7632   -1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4851   -1.0388   -0.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2691    0.7448    1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1661   -1.8550    0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  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  1  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  1
  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  6
 16 38  1  1
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  1
 20 44  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 17a-Estradiol.mol                                 
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0      -3.852  -2.510   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.186  -3.280   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.852  -0.970   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.519  -0.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.519  -3.280   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.185  -2.510   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.149  -3.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.483  -2.510   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.483  -0.970   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.816  -0.200   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.281  -0.676   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.186   0.570   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.281   1.816   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.757   3.280   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.816   1.340   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.816   2.880   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.483   2.110   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.149   1.340   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.149  -0.200   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.185  -0.970   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       0.149  -1.740   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.483   0.570   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.816  -1.740   0.000  0.00  0.00           H+0
CONECT    1    2    3    5                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3   20                                                       
CONECT    5    1    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   19   22                                             
CONECT   10    9   11   15   23                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   10   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    9   20   21                                             
CONECT   20   19    4    6                                                  
CONECT   21   19                                                            
CONECT   22    9                                                            
CONECT   23   10                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0000429
HETATM    1  C1  UNL     1      -2.176   1.978   0.179  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.140   0.564   0.697  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.356   0.405   1.949  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.112   0.564   1.771  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.658  -0.230   0.623  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.086  -0.139   0.440  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.926   0.208   1.463  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.312   0.292   1.272  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.852   0.024   0.044  1.00  0.00           C  
HETATM   10  O1  UNL     1       6.213   0.100  -0.168  1.00  0.00           O  
HETATM   11  C10 UNL     1       4.015  -0.329  -1.004  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.653  -0.404  -0.787  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.807  -0.785  -1.932  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.422  -0.265  -1.903  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.145   0.131  -0.604  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.517  -0.393  -0.333  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.482  -0.336  -1.434  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.823  -0.163  -0.760  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.527   0.032   0.735  1.00  0.00           C  
HETATM   20  O2  UNL     1      -3.601  -1.216   1.349  1.00  0.00           O  
HETATM   21  H1  UNL     1      -1.371   2.606   0.613  1.00  0.00           H  
HETATM   22  H2  UNL     1      -2.109   1.946  -0.924  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.163   2.412   0.461  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.629  -0.575   2.405  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.705   1.180   2.684  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.587   0.298   2.753  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.342   1.645   1.626  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.404  -1.309   0.840  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.595   0.438   2.466  1.00  0.00           H  
HETATM   30  H10 UNL     1       4.978   0.563   2.067  1.00  0.00           H  
HETATM   31  H11 UNL     1       6.794  -0.703  -0.029  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.489  -0.531  -1.954  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.314  -0.390  -2.861  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.832  -1.901  -2.094  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.247  -1.078  -2.322  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.296   0.558  -2.671  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.217   1.259  -0.591  1.00  0.00           H  
HETATM   38  H18 UNL     1      -1.472  -1.380   0.144  1.00  0.00           H  
HETATM   39  H19 UNL     1      -2.518  -1.349  -1.932  1.00  0.00           H  
HETATM   40  H20 UNL     1      -2.291   0.391  -2.231  1.00  0.00           H  
HETATM   41  H21 UNL     1      -4.279   0.763  -1.167  1.00  0.00           H  
HETATM   42  H22 UNL     1      -4.485  -1.039  -0.876  1.00  0.00           H  
HETATM   43  H23 UNL     1      -4.269   0.745   1.132  1.00  0.00           H  
HETATM   44  H24 UNL     1      -4.166  -1.855   0.864  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   43
CONECT   20   44
END

HMDB0000429
     RDKit          3D
17alpha-Estradiol
 44 47  0  0  0  0  0  0  0  0999 V2000
   -2.1765    1.9777    0.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1399    0.5640    0.6965 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3563    0.4055    1.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1118    0.5640    1.7709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6582   -0.2295    0.6232 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0858   -0.1391    0.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9256    0.2084    1.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3124    0.2922    1.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8518    0.0242    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2130    0.1003   -0.1676 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0155   -0.3290   -1.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6530   -0.4037   -0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -0.7851   -1.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.2648   -1.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453    0.1306   -0.6041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5175   -0.3933   -0.3326 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4818   -0.3359   -1.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8227   -0.1626   -0.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5268    0.0318    0.7348 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6013   -1.2165    1.3492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3706    2.6057    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087    1.9463   -0.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1633    2.4116    0.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285   -0.5750    2.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7050    1.1796    2.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5872    0.2977    2.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3419    1.6447    1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4043   -1.3092    0.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5953    0.4376    2.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9775    0.5631    2.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7942   -0.7025   -0.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4891   -0.5308   -1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143   -0.3902   -2.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324   -1.9012   -2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473   -1.0781   -2.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960    0.5580   -2.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2171    1.2590   -0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -1.3797    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5177   -1.3494   -1.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2908    0.3911   -2.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2786    0.7632   -1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4851   -1.0388   -0.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2691    0.7448    1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1661   -1.8550    0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  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  1  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  1
  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  6
 16 38  1  1
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  1
 20 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Alfatradiol	ChEBI
alpha-Estradiol	ChEBI
Estra-1,3,5(10)trien-3,17alpha-diol	ChEBI
Estradiol-17alpha	ChEBI
a-Estradiol	Generator
Α-estradiol	Generator
Estra-1,3,5(10)trien-3,17a-diol	Generator
Estra-1,3,5(10)trien-3,17α-diol	Generator
Estradiol-17a	Generator
Estradiol-17α	Generator
17a-Estradiol	Generator
17Α-estradiol	Generator
1,3,5-Estratriene-3,17a-diol	HMDB
13b-Methyl-1,3,5(10)-gonatriene-3,17a-diol	HMDB
17-Epiestradiol	HMDB
17a-Oestradiol	HMDB
3,17-Dihydroxyestratriene	HMDB
3,17a-Dihydroxyestra-1,3,5(10)-triene	HMDB
3,17a-Dihydroxyoestra-1,3,5(10)-triene	HMDB
Epiestradiol	HMDB
Epiestrol	HMDB
Estra-1,3,5(10)-triene-3,17a-diol	HMDB
Oestra-1,3,5(10)-triene-3,17a-diol	HMDB
17alpha-Estradiol	KEGG

Chemical Formula

C₁₈H₂₄O₂

Average Molecular Weight

272.382

Monoisotopic Molecular Weight

272.177630012

IUPAC Name

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

Traditional Name

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

CAS Registry Number

57-91-0

SMILES

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

InChI Identifier

InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17-,18+/m1/s1

InChI Key

VOXZDWNPVJITMN-SFFUCWETSA-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
17-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

17alpha-hydroxy steroid (CHEBI:17160 )
3-hydroxy steroid (CHEBI:17160 )
estradiol (CHEBI:17160 )
C18 steroids (estrogens) and derivatives (C02537 )
Estrane and derivatives (C02537 )
C18 steroids (estrogens) and derivatives (LMST02010029 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 499589)

Excreta

Biofluid or Excreta

Urine (PMID: 9812172)

Cellular substructure

Membrane (HMDB: HMDB0000429)
Extracellular (HMDB: HMDB0000429)

Source

Exogenous

Exogenous (HMDB: HMDB0000429)

Food

Fruit

Drupe

Apricot (FooDB: FOOD00144)

Tropical fruit

Pomegranate (FooDB: FOOD00151)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0000429)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Glutaryl Co A Dehydrogenase Deficiency (Gdhd) (MarkerDB: MDB00029982)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	216 - 219 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0039 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	3.57	ALOGPS
logP	3.75	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.9 m³·mol⁻¹	ChemAxon
Polarizability	31.93 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	166.031	31661259
DarkChem	[M-H]-	163.238	31661259
AllCCS	[M+H]+	168.875	32859911
AllCCS	[M-H]-	174.15	32859911
DeepCCS	[M-2H]-	212.545	30932474
DeepCCS	[M+Na]+	187.345	30932474
AllCCS	[M+H]+	168.9	32859911
AllCCS	[M+H-H2O]+	165.5	32859911
AllCCS	[M+NH4]+	172.0	32859911
AllCCS	[M+Na]+	172.9	32859911
AllCCS	[M-H]-	174.2	32859911
AllCCS	[M+Na-2H]-	174.0	32859911
AllCCS	[M+HCOO]-	173.9	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.	6.33 minutes	32390414
Predicted by Siyang on May 30, 2022	13.736 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.6 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2196.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	335.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	187.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	458.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	659.5 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	605.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	93.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1191.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	473.5 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	1456.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	383.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	404.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	294.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	225.7 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	47.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
17alpha-Estradiol	[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	3547.9	Standard polar	33892256
17alpha-Estradiol	[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	2655.4	Standard non polar	33892256
17alpha-Estradiol	[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	2739.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
17alpha-Estradiol,1TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1CC[C@H]2O[Si](C)(C)C	2677.5	Semi standard non polar	33892256
17alpha-Estradiol,1TMS,isomer #2	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@H]2O	2655.2	Semi standard non polar	33892256
17alpha-Estradiol,2TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@H]2O[Si](C)(C)C	2708.0	Semi standard non polar	33892256
17alpha-Estradiol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@@]21C	2965.7	Semi standard non polar	33892256
17alpha-Estradiol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@H]2O	2953.9	Semi standard non polar	33892256
17alpha-Estradiol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@H]2O[Si](C)(C)C(C)(C)C	3270.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 17alpha-Estradiol GC-MS (2 TMS)	splash10-00p0-3970000000-ea6c869f7a3556f5fb55	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 17alpha-Estradiol GC-MS (Non-derivatized)	splash10-00p0-3970000000-ea6c869f7a3556f5fb55	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17alpha-Estradiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-1490000000-9f16d080d50dcea52de4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17alpha-Estradiol GC-MS (2 TMS) - 70eV, Positive	splash10-0udr-2279400000-cea6d26f1ab9c44b5160	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17alpha-Estradiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17alpha-Estradiol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17alpha-Estradiol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17alpha-Estradiol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17alpha-Estradiol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17alpha-Estradiol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-2950000000-9cd3211b8fd922d6f32b	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 - 17alpha-Estradiol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00di-0090000000-1ba1e242ed699b46bf67	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17alpha-Estradiol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a59-7900000000-0dae6df990a37c6c3fb3	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17alpha-Estradiol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0a4i-8900000000-956bcdeac1a836c6b83c	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17alpha-Estradiol 30V, Positive-QTOF	splash10-0a4i-0190000000-452a42851493e9ce5c80	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17alpha-Estradiol 40V, Positive-QTOF	splash10-004i-0690000000-71ce13a2bfc9d4213bb7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17alpha-Estradiol 20V, Positive-QTOF	splash10-05fr-0090000000-2f90ef030c1d0edf8ad0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17alpha-Estradiol 10V, Positive-QTOF	splash10-00di-0090000000-abcf1c18fabe5707d6dd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17alpha-Estradiol 50V, Positive-QTOF	splash10-004j-0930000000-a22a631636419abce8d1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17alpha-Estradiol 10V, Negative-QTOF	splash10-00di-0090000000-a3dd3e1428abd9a33604	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17alpha-Estradiol 40V, Negative-QTOF	splash10-00dj-0690000000-8ffd5ef2044d03b46720	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17alpha-Estradiol 20V, Negative-QTOF	splash10-00di-0090000000-7155e44ebc26fe65b901	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17alpha-Estradiol 20V, Positive-QTOF	splash10-05fr-0090000000-86e488508b64b443756f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17alpha-Estradiol 40V, Positive-QTOF	splash10-004i-0690000000-2e46725f97f4019883a5	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 10V, Positive-QTOF	splash10-0ab9-0090000000-6ced41e08d82a4b04630	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 20V, Positive-QTOF	splash10-0ab9-0590000000-4d9df1569ae569967694	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 40V, Positive-QTOF	splash10-004u-4690000000-661cc510ebfd4c2a2465	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 10V, Negative-QTOF	splash10-00di-0090000000-d0a3fa240c972ee299db	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 20V, Negative-QTOF	splash10-00di-0090000000-5e0ebfacd0ec2ed930f5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 40V, Negative-QTOF	splash10-054o-0090000000-da2f1bf0efabdae03188	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 10V, Positive-QTOF	splash10-00di-0090000000-75c81b9a2f86b3e98ca7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 20V, Positive-QTOF	splash10-05i1-0690000000-f9708f269ca012832fdc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 40V, Positive-QTOF	splash10-05dj-3910000000-ae2ec96914444b71ca58	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 10V, Negative-QTOF	splash10-00di-0090000000-fb43b1971567fc332aa7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 20V, Negative-QTOF	splash10-00di-0090000000-28ae91cf9a3f37856adb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha-Estradiol 40V, Negative-QTOF	splash10-0f79-0090000000-325f0a631253fd5784bb	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.3200 +/- 0.0001 uM	Adult (>18 years old)	Male	Normal	499589	details
Urine	Detected and Quantified	0.000262+/-0.000065 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9812172	details
Urine	Detected and Quantified	2.3 +/- 1.6 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12118531	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	9.4 +/- 5.0 umol/mmol creatinine	Adult (>18 years old)	Both	Glutaryl-CoA dehydrogenase deficiency (GDHD)	12118531	details

Associated Disorders and Diseases

Disease References

Glutaryl-CoA dehydrogenase deficiency (GDHD)
Pitt J, Carpenter K, Wilcken B, Boneh A: 3-Hydroxyglutarate excretion is increased in ketotic patients: implications for glutaryl-CoA dehydrogenase deficiency testing. J Inherit Metab Dis. 2002 May;25(2):83-8. [PubMed:12118531 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112198

KNApSAcK ID

Not Available

Chemspider ID

61840

KEGG Compound ID

C02537

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

17α-Estradiol

METLIN ID

5418

PubChem Compound

68570

PDB ID

Not Available

ChEBI ID

17160

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029982

Good Scents ID

Not Available

References

Synthesis Reference

Gardi, Rinaldo; Pedrali, Cesare; Ercoli, Alberto. 3-Cyclopentyl ethers of 16,17-oxygenated estrogens. New synthesis of 17a-estradiol. Gazzetta Chimica Italiana (1963), 93(8-9), 1028-43.

Material Safety Data Sheet (MSDS)

Not Available

General References

Corbier P, Roffi J, Rhoda J, Valens M: [Female sex behavior of male rats castrated at birth and given female sex hormones: effects of hour of castration]. C R Seances Acad Sci III. 1981 Nov 23;293(11):649-54. [PubMed:6800584 ]
Vic P, Garcia M, Andre J, Humeau C, Rochefort H: [Early effect of estradiol on ultrastructure of chromatin in the endometrium and hormone-dependent mammary tumors]. C R Acad Sci Hebd Seances Acad Sci D. 1978 Jul 17;287(3):141-4. [PubMed:100250 ]
Salat-Baroux J, Scemama-Kestenberg H, Couturier JY, Firmin C, Agnes E, Levy G, Vuillard E: [Postovulatory hormones in plasma, peritoneal and follicular compartments]. J Gynecol Obstet Biol Reprod (Paris). 1982;11(4):447-56. [PubMed:6292281 ]
Zhu BT, Han GZ, Shim JY, Wen Y, Jiang XR: Quantitative structure-activity relationship of various endogenous estrogen metabolites for human estrogen receptor alpha and beta subtypes: Insights into the structural determinants favoring a differential subtype binding. Endocrinology. 2006 Sep;147(9):4132-50. doi: 10.1210/en.2006-0113. Epub 2006 May 25. [PubMed:16728493 ]
Stout MB, Steyn FJ, Jurczak MJ, Camporez JG, Zhu Y, Hawse JR, Jurk D, Palmer AK, Xu M, Pirtskhalava T, Evans GL, de Souza Santos R, Frank AP, White TA, Monroe DG, Singh RJ, Casaclang-Verzosa G, Miller JD, Clegg DJ, LeBrasseur NK, von Zglinicki T, Shulman GI, Tchkonia T, Kirkland JL: 17alpha-Estradiol Alleviates Age-related Metabolic and Inflammatory Dysfunction in Male Mice Without Inducing Feminization. J Gerontol A Biol Sci Med Sci. 2017 Jan;72(1):3-15. doi: 10.1093/gerona/glv309. Epub 2016 Jan 24. [PubMed:26809497 ]

Showing metabocard for 17alpha-Estradiol (HMDB0000429)

MOL for HMDB0000429 (17alpha-Estradiol)

3D MOL for HMDB0000429 (17alpha-Estradiol)

3D SDF for HMDB0000429 (17alpha-Estradiol)

3D-SDF for HMDB0000429 (17alpha-Estradiol)

PDB for HMDB0000429 (17alpha-Estradiol)

3D PDB for HMDB0000429 (17alpha-Estradiol)

SMILES for HMDB0000429 (17alpha-Estradiol)

INCHI for HMDB0000429 (17alpha-Estradiol)

Structure for HMDB0000429 (17alpha-Estradiol)

3D Structure for HMDB0000429 (17alpha-Estradiol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra