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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (29)transporters (2) Show 31 proteins XML

enzymes (29)transporters (2) Show 31 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:39:00 UTC

HMDB ID

HMDB0000153

Secondary Accession Numbers

HMDB00153

Metabolite Identification

Common Name

Estriol

Description

Estriol is a metabolite of estrone metabolized via 16alpha-hydroxyestrone through the enzyme 16alpha-hydroxysteroid dehydrogenase (EC 1.1.1.147) or to 2- or 4-hydroxyestrone (catechol estrogens) by the action of catecho-O-methyltransferase (EC 2.1.1.6). The latter metabolites can be formed in the brain and may compete with receptors for catecholamines. Metabolites are conjugated with sulfate or glucuronide before excretion by the kidney. During pregnancy, estriol constitutes 60-70% of the total estrogens, increasing to 300-500-fold in relation to non-pregnant women. The late term human fetus produces relatively large amounts of 16 alphahydroxy DHEA, which serves the mother as a precursor of estriol. It has been shown that 90% of the precursors for the formation of estriol are of fetal origin. If abnormal maternal serum screening results, specifically low levels of unconjugated estriol in the second trimester are detected, a diagnosis of Smith-Lemli-Opitz syndrome (SLOS),or RSH is suspected. SLOS is an autosomal recessive disorder caused by mutations of the gene encoding 7-dehydrocholesterol reductase (EC 1.3.1.21, DHCR7). (PMID: 16202579 , 16112271 , 16097001 ).

Structure

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

HMDB0000153
     RDKit          3D
Estriol
 45 48  0  0  0  0  0  0  0  0999 V2000
   -2.0881    1.1969    1.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9997   -0.2575    0.6820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3178   -1.0986    1.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1689   -1.1076    1.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7857   -0.7655    0.3453 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1965   -0.4122    0.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9929   -0.3655    1.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3170   -0.0198    1.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9007    0.2908    0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2410    0.6391    0.0323 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1052    0.2429   -0.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7927   -0.0997   -0.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8869   -0.1588   -2.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033    0.7140   -1.6850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0232    0.2848   -0.4409 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3079   -0.3829   -0.6801 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2296    0.3023   -1.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5984    0.1010   -0.9590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4867   -0.5122   -1.8293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3712   -0.7107    0.3042 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3361   -0.4201    1.2650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0640    1.4066    1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3122    1.4426    1.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9950    1.8910    0.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7513   -2.1385    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6959   -0.7560    2.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5222   -0.4234    2.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5180   -2.1099    1.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7037   -1.6883   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5369   -0.6077    2.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9484    0.0206    2.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8365    0.6778    0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4837    0.4732   -1.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3906    0.2859   -2.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5832   -1.2060   -2.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0081    0.7532   -2.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1173    1.7566   -1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0761    1.1672    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083   -1.4563   -0.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2447   -0.2227   -2.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0176    1.3604   -1.8014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9578    1.0989   -0.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1207    0.1249   -2.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3804   -1.8042    0.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2030   -1.0460    2.0055 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
 18 20  1  0
 20 21  1  0
 16  2  1  0
 20  2  1  0
 15  5  1  0
 12  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  7 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  1
 16 39  1  6
 17 40  1  0
 17 41  1  0
 18 42  1  1
 19 43  1  0
 20 44  1  6
 21 45  1  0
M  END


  Mrv1652309152018252D          

 24 27  0  0  0  0            999 V2000
10001.078110001.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8009 9998.1252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.364510000.1943    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6525 9998.9603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.0781 9998.9603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2277 9999.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5133 9999.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5133 9998.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2277 9998.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9386 9999.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9386 9998.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6531 9998.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3676 9998.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.365610001.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.651110000.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6511 9999.7870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3656 9999.3746    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.864810000.8671    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.080210000.6121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.0801 9999.7871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.8648 9999.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.349610000.1996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.119710001.6517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.174610000.1996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8  2  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  9 11  1  0  0  0  0
 10  6  1  0  0  0  0
 16 10  1  0  0  0  0
 16  4  1  6  0  0  0
 13 17  1  0  0  0  0
 17  3  1  1  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  1  1  0  0  0
 22 24  1  6  0  0  0
 17 20  1  0  0  0  0
 20  5  1  6  0  0  0
 14 19  1  0  0  0  0
 19  1  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0000153

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12C[C@@H](O)[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/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1

> <INCHI_KEY>
PROQIPRRNZUXQM-ZXXIGWHRSA-N

> <FORMULA>
C18H24O3

> <MOLECULAR_WEIGHT>
288.3814

> <EXACT_MASS>
288.172544634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.08429086433415

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol

> <ALOGPS_LOGP>
2.54

> <JCHEM_LOGP>
2.6705977213333343

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.6240954646046

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.326834303487214

> <JCHEM_PKA_STRONGEST_BASIC>
-3.15653538815926

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
81.2662

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000153
     RDKit          3D
Estriol
 45 48  0  0  0  0  0  0  0  0999 V2000
   -2.0881    1.1969    1.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9997   -0.2575    0.6820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3178   -1.0986    1.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1689   -1.1076    1.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7857   -0.7655    0.3453 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1965   -0.4122    0.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9929   -0.3655    1.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3170   -0.0198    1.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9007    0.2908    0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2410    0.6391    0.0323 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1052    0.2429   -0.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7927   -0.0997   -0.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8869   -0.1588   -2.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033    0.7140   -1.6850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0232    0.2848   -0.4409 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3079   -0.3829   -0.6801 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2296    0.3023   -1.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5984    0.1010   -0.9590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4867   -0.5122   -1.8293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3712   -0.7107    0.3042 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3361   -0.4201    1.2650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0640    1.4066    1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3122    1.4426    1.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9950    1.8910    0.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7513   -2.1385    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6959   -0.7560    2.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5222   -0.4234    2.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5180   -2.1099    1.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7037   -1.6883   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5369   -0.6077    2.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9484    0.0206    2.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8365    0.6778    0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4837    0.4732   -1.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3906    0.2859   -2.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5832   -1.2060   -2.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0081    0.7532   -2.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1173    1.7566   -1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0761    1.1672    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083   -1.4563   -0.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2447   -0.2227   -2.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0176    1.3604   -1.8014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9578    1.0989   -0.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1207    0.1249   -2.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3804   -1.8042    0.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2030   -1.0460    2.0055 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
 18 20  1  0
 20 21  1  0
 16  2  1  0
 20  2  1  0
 15  5  1  0
 12  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  7 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  1
 16 39  1  6
 17 40  1  0
 17 41  1  0
 18 42  1  1
 19 43  1  0
 20 44  1  6
 21 45  1  0
M  END

HEADER    PROTEIN                                 15-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-SEP-20         0                                  
HETATM    1  C   UNK     0    8668.6798669.359   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8660.6958663.167   0.000  0.00  0.00           O+0
HETATM    3  H   UNK     0    8667.3478667.029   0.000  0.00  0.00           H+0
HETATM    4  H   UNK     0    8666.0188664.726   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8668.6798664.726   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0    8663.3588666.255   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8662.0258665.485   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.0258663.945   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.3588663.175   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.6858665.485   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.6858663.945   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.0198663.175   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.3538663.945   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.3498668.579   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8666.0158667.809   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8666.0158666.269   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8667.3498665.499   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8670.1488668.285   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8668.6838667.809   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8668.6838666.269   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8670.1488665.793   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8671.0538667.039   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8670.6238669.750   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0    8672.5938667.039   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    8                                                            
CONECT    3   17                                                            
CONECT    4   16                                                            
CONECT    5   20                                                            
CONECT    6    7   10                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9    2                                                  
CONECT    9    8   11                                                       
CONECT   10   11    6   16                                                  
CONECT   11   10   12    9                                                  
CONECT   12   11   13                                                       
CONECT   13   12   17                                                       
CONECT   14   15   19                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   10    4                                             
CONECT   17   16   13    3   20                                             
CONECT   18   19   22   23                                                  
CONECT   19   18   20   14    1                                             
CONECT   20   19   21   17    5                                             
CONECT   21   20   22                                                       
CONECT   22   18   21   24                                                  
CONECT   23   18                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0000153
HETATM    1  C1  UNL     1      -2.088   1.197   1.102  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.000  -0.257   0.682  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.318  -1.099   1.711  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.169  -1.108   1.644  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.786  -0.766   0.345  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.197  -0.412   0.364  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.993  -0.366   1.486  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.317  -0.020   1.366  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.901   0.291   0.142  1.00  0.00           C  
HETATM   10  O1  UNL     1       6.241   0.639   0.032  1.00  0.00           O  
HETATM   11  C10 UNL     1       4.105   0.243  -0.969  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.793  -0.100  -0.850  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.887  -0.159  -2.055  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.703   0.714  -1.685  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.023   0.285  -0.441  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.308  -0.383  -0.680  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.230   0.302  -1.583  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.598   0.101  -0.959  1.00  0.00           C  
HETATM   19  O2  UNL     1      -4.487  -0.512  -1.829  1.00  0.00           O  
HETATM   20  C18 UNL     1      -3.371  -0.711   0.304  1.00  0.00           C  
HETATM   21  O3  UNL     1      -4.336  -0.420   1.265  1.00  0.00           O  
HETATM   22  H1  UNL     1      -3.064   1.407   1.591  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.312   1.443   1.865  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.995   1.891   0.250  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.751  -2.138   1.603  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.696  -0.756   2.702  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.522  -0.423   2.471  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.518  -2.110   1.975  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.704  -1.688  -0.311  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.537  -0.608   2.431  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.948   0.021   2.231  1.00  0.00           H  
HETATM   32  H11 UNL     1       6.836   0.678   0.842  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.484   0.473  -1.977  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.391   0.286  -2.914  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.583  -1.206  -2.194  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.008   0.753  -2.540  1.00  0.00           H  
HETATM   37  H16 UNL     1       1.117   1.757  -1.583  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.076   1.167   0.249  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.208  -1.456  -0.883  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.245  -0.223  -2.576  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.018   1.360  -1.801  1.00  0.00           H  
HETATM   42  H21 UNL     1      -3.958   1.099  -0.638  1.00  0.00           H  
HETATM   43  H22 UNL     1      -5.121   0.125  -2.243  1.00  0.00           H  
HETATM   44  H23 UNL     1      -3.380  -1.804   0.049  1.00  0.00           H  
HETATM   45  H24 UNL     1      -4.203  -1.046   2.006  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   16   20
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   15   29
CONECT    6    7    7   12
CONECT    7    8   30
CONECT    8    9    9   31
CONECT    9   10   11
CONECT   10   32
CONECT   11   12   12   33
CONECT   12   13
CONECT   13   14   34   35
CONECT   14   15   36   37
CONECT   15   16   38
CONECT   16   17   39
CONECT   17   18   40   41
CONECT   18   19   20   42
CONECT   19   43
CONECT   20   21   44
CONECT   21   45
END

HMDB0000153
     RDKit          3D
Estriol
 45 48  0  0  0  0  0  0  0  0999 V2000
   -2.0881    1.1969    1.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9997   -0.2575    0.6820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3178   -1.0986    1.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1689   -1.1076    1.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7857   -0.7655    0.3453 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1965   -0.4122    0.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9929   -0.3655    1.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3170   -0.0198    1.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9007    0.2908    0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2410    0.6391    0.0323 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1052    0.2429   -0.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7927   -0.0997   -0.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8869   -0.1588   -2.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033    0.7140   -1.6850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0232    0.2848   -0.4409 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3079   -0.3829   -0.6801 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2296    0.3023   -1.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5984    0.1010   -0.9590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4867   -0.5122   -1.8293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3712   -0.7107    0.3042 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3361   -0.4201    1.2650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0640    1.4066    1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3122    1.4426    1.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9950    1.8910    0.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7513   -2.1385    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6959   -0.7560    2.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5222   -0.4234    2.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5180   -2.1099    1.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7037   -1.6883   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5369   -0.6077    2.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9484    0.0206    2.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8365    0.6778    0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4837    0.4732   -1.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3906    0.2859   -2.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5832   -1.2060   -2.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0081    0.7532   -2.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1173    1.7566   -1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0761    1.1672    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083   -1.4563   -0.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2447   -0.2227   -2.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0176    1.3604   -1.8014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9578    1.0989   -0.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1207    0.1249   -2.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3804   -1.8042    0.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2030   -1.0460    2.0055 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
 18 20  1  0
 20 21  1  0
 16  2  1  0
 20  2  1  0
 15  5  1  0
 12  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  7 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  1
 16 39  1  6
 17 40  1  0
 17 41  1  0
 18 42  1  1
 19 43  1  0
 20 44  1  6
 21 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(16alpha,17beta)-Estra-1,3,5(10)-triene-3,16,17-triol	ChEBI
1,3,5(10)-Estratriene-3,16-alpha,17beta-triol	ChEBI
16alpha,17beta-Estriol	ChEBI
16alpha-Hydroxyestradiol	ChEBI
3,16alpha,17beta-Trihydroxy-Delta(1,3,5)-estratriene	ChEBI
Deuslon-a	ChEBI
Estriel	ChEBI
Oestriol	ChEBI
Trihydroxyestrin	ChEBI
(16a,17b)-Estra-1,3,5(10)-triene-3,16,17-triol	Generator
(16Α,17β)-estra-1,3,5(10)-triene-3,16,17-triol	Generator
1,3,5(10)-Estratriene-3,16-a,17b-triol	Generator
1,3,5(10)-Estratriene-3,16-α,17β-triol	Generator
16a,17b-Estriol	Generator
16Α,17β-estriol	Generator
16a-Hydroxyestradiol	Generator
16Α-hydroxyestradiol	Generator
3,16a,17b-Trihydroxy-delta(1,3,5)-estratriene	Generator
3,16Α,17β-trihydroxy-δ(1,3,5)-estratriene	Generator
3,16a,17b-Trihydroxy-δ(1,3,5)-estratriene	HMDB
13b-Methyl-1,3,5(10)-gonatriene-3,16a,17b-triol	HMDB
16-alpha,17-beta-Estriol	HMDB
16-alpha,17-beta-Oestriol	HMDB
16-alpha-Hydroxyestradiol	HMDB
16a-Estriol	HMDB
16alpha,17beta-Oestriol	HMDB
16alpha-Hydroxy-17beta-estradiol	HMDB
16alpha-Hydroxyoestradiol	HMDB
3,16a,17b-Estriol	HMDB
3,16a,17b-Trihydroxyestra-1,3,5(10)-triene	HMDB
3,16alpha,17beta-Trihydroxy-1,3,5(10)-estratriene	HMDB
3,16alpha,17beta-Trihydroxyestra-1,3,5(10)-triene	HMDB
Aacifemine	HMDB
Colpogyn	HMDB
Colpovister	HMDB
Destriol	HMDB
Deuslon a	HMDB
Estra-1,3,5(10)-triene-3,16a,17b-triol	HMDB
Estratriol	HMDB
Follicular hormone hydrate	HMDB
Gynasan	HMDB
Hemostyptanon	HMDB
Holin V	HMDB
Hormomed	HMDB
Incurin	HMDB
Klimax e	HMDB
Klimoral	HMDB
Oekolp	HMDB
Oestratriol	HMDB
Oestriolum	HMDB
Orestin	HMDB
Orgastyptin	HMDB
Ortho-gynest	HMDB
Ovesterin	HMDB
Ovestin	HMDB
Ovestinon	HMDB
Ovestrion	HMDB
Ovo-vinces	HMDB
Theelol	HMDB
Tridestrin	HMDB
Triovex	HMDB
16-alpha-Hydroxy-estradiol	HMDB
(16beta,17beta)-Estra-1,3,5(10)-triene-3,16,17-triol	HMDB
16beta Hydroxy estradiol	HMDB
16beta-Hydroxy-estradiol	HMDB
Epiestriol	HMDB
16 alpha Hydroxy estradiol	HMDB
16alpha,17beta Estriol	HMDB
Estra-1,3,5(10)-triene-3,16beta,17beta-triol	HMDB
13beta-Methyl-1,3,5(10)-gonatriene-3,16alpha,17beta-triol	HMDB
13β-Methyl-1,3,5(10)-gonatriene-3,16α,17β-triol	HMDB
16alpha-Estriol	HMDB
16α-Estriol	HMDB
3,16alpha,17beta-Estriol	HMDB
3,16α,17β-Estriol	HMDB
3,16α,17β-Trihydroxyestra-1,3,5(10)-triene	HMDB
Estriol	HMDB

Chemical Formula

C₁₈H₂₄O₃

Average Molecular Weight

288.3814

Monoisotopic Molecular Weight

288.172544634

IUPAC Name

(1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol

Traditional Name

(1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol

CAS Registry Number

50-27-1

SMILES

[H][C@@]12C[C@@H](O)[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/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1

InChI Key

PROQIPRRNZUXQM-ZXXIGWHRSA-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
17-hydroxysteroid
16-hydroxysteroid
16-alpha-hydroxysteroid
Hydroxysteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Cyclic alcohol
Secondary alcohol
1,2-diol
Polyol
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

17beta-hydroxy steroid (CHEBI:27974 )
3-hydroxy steroid (CHEBI:27974 )
16alpha-hydroxy steroid (CHEBI:27974 )
C18 steroids (estrogens) and derivatives (C05141 )
Estrane and derivatives (C05141 )
Estrogens (C05141 )
C18 steroids (estrogens) and derivatives (LMST02010003 )

Ontology

Physiological effect

Health effect

Observation

Pregnancy (HMDB: HMDB0000153)

Endocrine system disorder

Diabetes mellitus type 2 (HMDB: HMDB0000153)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 484160)
Amniotic Fluid (PMID: 2994907)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0000153)

Organ substructure

Adrenal cortex (HMDB: HMDB0000153)
Adrenal cortex (HMDB: HMDB0000153)

Organ

Gland

Adrenal Gland (HMDB: HMDB0000153)
Adrenal Gland (HMDB: HMDB0000153)

Excreta

Biofluid or Excreta

Urine (PMID: 8478958)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000153)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000153)

Source

Exogenous

Exogenous (HMDB: HMDB0000153)

Food

Food (HMDB: HMDB0000153)

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)

Pulse

Bean

Common bean (FooDB: FOOD00134)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Fruit

Tropical fruit

Pomegranate (FooDB: FOOD00151)

Endogenous

Endogenous (HMDB: HMDB0000153)

Plant

Plant (HMDB: HMDB0000153)
Fabaceae (HMDB: HMDB0000153)

Hormone (HMDB: HMDB0000153)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000153)

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0000153)

Pharmaceutical (HMDB: HMDB0000153)

Biomarker

Diabetes mellitus type 2 (MarkerDB: MDB00000074)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	282 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	2.45	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	2.54	ALOGPS
logP	2.67	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	81.27 m³·mol⁻¹	ChemAxon
Polarizability	33.08 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]+	168.846	31661259
DarkChem	[M-H]-	167.09	31661259
AllCCS	[M+H]+	172.383	32859911
AllCCS	[M-H]-	175.988	32859911
DeepCCS	[M-2H]-	212.642	30932474
DeepCCS	[M+Na]+	187.456	30932474
AllCCS	[M+H]+	172.4	32859911
AllCCS	[M+H-H2O]+	169.1	32859911
AllCCS	[M+NH4]+	175.4	32859911
AllCCS	[M+Na]+	176.3	32859911
AllCCS	[M-H]-	176.0	32859911
AllCCS	[M+Na-2H]-	175.8	32859911
AllCCS	[M+HCOO]-	175.8	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.	5.12 minutes	32390414
Predicted by Siyang on May 30, 2022	11.9922 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.71 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2061.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	247.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	168.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	274.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	547.4 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	506.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	83.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	928.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	443.0 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	1377.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	316.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	363.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	300.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	156.9 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	79.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Estriol	[H][C@@]12C[C@@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	3943.9	Standard polar	33892256
Estriol	[H][C@@]12C[C@@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	2917.3	Standard non polar	33892256
Estriol	[H][C@@]12C[C@@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	2941.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Estriol,1TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1C[C@@H](O[Si](C)(C)C)[C@@H]2O	2789.2	Semi standard non polar	33892256
Estriol,1TMS,isomer #2	C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1C[C@@H](O)[C@@H]2O[Si](C)(C)C	2794.1	Semi standard non polar	33892256
Estriol,1TMS,isomer #3	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C[C@@H](O)[C@@H]2O	2771.9	Semi standard non polar	33892256
Estriol,2TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C[C@@H](O[Si](C)(C)C)[C@@H]2O	2842.9	Semi standard non polar	33892256
Estriol,2TMS,isomer #2	C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1C[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C	2782.1	Semi standard non polar	33892256
Estriol,2TMS,isomer #3	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C[C@@H](O)[C@@H]2O[Si](C)(C)C	2842.9	Semi standard non polar	33892256
Estriol,3TMS,isomer #1	C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C	2907.4	Semi standard non polar	33892256
Estriol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@]2(C)[C@H]1O	3065.1	Semi standard non polar	33892256
Estriol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@@]21C	3081.3	Semi standard non polar	33892256
Estriol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@@H](O)[C@@H]2O	3084.3	Semi standard non polar	33892256
Estriol,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]1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O	3374.5	Semi standard non polar	33892256
Estriol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@]2(C)[C@H]1O[Si](C)(C)C(C)(C)C	3303.1	Semi standard non polar	33892256
Estriol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C	3391.4	Semi standard non polar	33892256
Estriol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O[Si](C)(C)C(C)(C)C	3664.8	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Amniotic Fluid
Blood
Urine

Tissue Locations

Adrenal Cortex
Adrenal Gland
Kidney
Liver
Placenta
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Estrone Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Amniotic Fluid	Detected and Quantified	0.0023 +/- 0.0007 uM	Adult (>18 years old)	Both	Normal	2994907	details
Blood	Detected and Quantified	0.006 +/- 0.002 uM	Adult (>18 years old)	Both	Normal	2994907	details
Blood	Detected and Quantified	0.000100 -0.00700 uM	Adult (>18 years old)	Female	Normal	Molecular You	details
Urine	Detected and Quantified	0.001 +/- 0.00055 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	8478958	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Amniotic Fluid	Detected and Quantified	0.004 +/- 0.002 uM	Adult (>18 years old)	Both	Ambulant pregnancy	2994907	details
Blood	Detected and Quantified	0.205 +/- 0.04 uM	Adult (>18 years old)	Female	Diabetes	484160	details
Blood	Detected and Quantified	<0.00000002 uM	Children (1-13 years old)	Female	Aromatase deficiency	9177373	details

Associated Disorders and Diseases

Disease References

Pregnancy
Andreolini F, Borra C, Caccamo F, Di Corcia A, Nicoletti I, Samperi R, Improta F: Estriol and its conjugates in late pregnancy determined by extraction with Carbopack B and liquid chromatography with fluorometric detection. Clin Chem. 1985 Oct;31(10):1698-702. [PubMed:2994907 ]
Diabetes mellitus type 2
Giussi GA, Ballejo G, Benedetti WL: Estriol serum levels, neonatal vitality and stromal villous edema in diabetic pregnancies. Acta Diabetol Lat. 1979 Apr-Jun;16(2):105-10. [PubMed:484160 ]
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 ]

Associated OMIM IDs

125853 (Diabetes mellitus type 2)
613546 (Aromatase deficiency)

External Links

DrugBank ID

DB04573

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB006781

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

27974

Food Biomarker Ontology

Not Available

VMH ID

ESTRIOL

MarkerDB ID

MDB00000074

Good Scents ID

Not Available

References

Synthesis Reference

Leeds, Norma S.; Fukushima, David K.; Gallagher, T. F. Studies of steroid ring D epoxides of enol acetates; a new synthesis of estriol and of androstane-3b,16a,17b-triol. Journal of the American Chemical Society (1954), 76 2943-8.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Diczfalusy E: The early history of estriol. J Steroid Biochem. 1984 Apr;20(4B):945-53. [PubMed:6374294 ]
Kashork CD, Sutton VR, Fonda Allen JS, Schmidt DE, Likhite ML, Potocki L, O'Brien WE, Shaffer LG: Low or absent unconjugated estriol in pregnancy: an indicator for steroid sulfatase deficiency detectable by fluorescence in situ hybridization and biochemical analysis. Prenat Diagn. 2002 Nov;22(11):1028-32. [PubMed:12424769 ]
Furuhashi N, Tsujiei M: [Clinical significance of serum and urinary estriol analysis in endocrine tests of the gonadal and placental system]. Nihon Rinsho. 1989 Dec;48 Suppl:1260-2. [PubMed:2621854 ]
Ronin-Walknowska E, Szczygielski A, Skoczowska M: [Usefulness of determining free estriol, placental lactogen, progesterone, placental alkaline phosphatase, uric acid, hematocrit, hemoglobin and proteins in the blood and estrogen in the urine in the prognosis of the status of newborn infants in EPH gestosis]. Ginekol Pol. 1987 Jan;58(1):21-6. [PubMed:3583036 ]
Fredricsson B, Carlstrom K, Eneroth P: Short-term variations in urinary estriol and renal function. Possible effects of extraneous conditions. Gynecol Obstet Invest. 1978;9(5):268-76. [PubMed:752645 ]
Andreolini F, Borra C, Caccamo F, Di Corcia A, Nicoletti I, Samperi R, Improta F: Estriol and its conjugates in late pregnancy determined by extraction with Carbopack B and liquid chromatography with fluorometric detection. Clin Chem. 1985 Oct;31(10):1698-702. [PubMed:2994907 ]
Truran PL, Read GF, Walker S: Radioimmunoassay for salivary estriol, with use of an 125I radioligand and a solid-phase separation technique. Clin Chem. 1982 Dec;28(12):2393-7. [PubMed:7139918 ]
Izumi H, Saito N, Ichiki S, Makino Y, Yukitake K, Kaneoka T: Prenatal diagnosis of congenital lipoid adrenal hyperplasia. Obstet Gynecol. 1993 May;81(5 ( Pt 2)):839-41. [PubMed:8469492 ]
Guedeney X, Chanez C, Grenier A, Scherrmann JM: Temperature-dependent immunoreactive assay to screen for digoxin-like immunoreactive factor(s). Clin Chem. 1991 Nov;37(11):1900-4. [PubMed:1718632 ]
Andreolini F, Di Corcia A, Lagana A, Samperi R, Raponi G: Preliminary isolation of urinary placental estriol before gas or liquid chromatography. Clin Chem. 1983 Dec;29(12):2076-8. [PubMed:6640903 ]
Evans JJ, Wilkinson AR, Aickin DR: Salivary estriol concentrations during normal pregnancies, and a comparison with plasma estriol. Clin Chem. 1984 Jan;30(1):120-1. [PubMed:6690116 ]
Kono H, Furuhashi N, Shinkawa O, Takahashi T, Tsujiei M, Yajima A: The maternal serum cortisol levels after onset of labor. Tohoku J Exp Med. 1987 Jun;152(2):133-7. [PubMed:3629582 ]
Moore ML: Biochemical markers for preterm labor and birth: what is their role in the care of pregnant women? MCN Am J Matern Child Nurs. 1999 Mar-Apr;24(2):80-6. [PubMed:10083784 ]
Pentikainen PJ, Pentikainen LA, Azarnoff DL, Dujovne CA: Plasma levels and excretion of estrogens in urine in chronic lever disease. Gastroenterology. 1975 Jul;69(1):20-7. [PubMed:1171044 ]
Nutman A, Freud E, Itzhaky D, Dolfin T, Tepper R: High maternal estriol level in pregnancy as a predictor of surgical intervention for undescended testis. Fertil Steril. 2005 Jul;84(1):249-52. [PubMed:16009196 ]
Pasqualini JR: Enzymes involved in the formation and transformation of steroid hormones in the fetal and placental compartments. J Steroid Biochem Mol Biol. 2005 Dec;97(5):401-15. Epub 2005 Oct 3. [PubMed:16202579 ]
Lardy H, Marwah A, Marwah P: C(19)-5-ene steroids in nature. Vitam Horm. 2005;71:263-99. [PubMed:16112271 ]
Shinawi M, Szabo S, Popek E, Wassif CA, Porter FD, Potocki L: Recognition of Smith-Lemli-Opitz syndrome (RSH) in the fetus: utility of ultrasonography and biochemical analysis in pregnancies with low maternal serum estriol. Am J Med Genet A. 2005 Sep 15;138(1):56-60. [PubMed:16097001 ]
Soldan SS, Alvarez Retuerto AI, Sicotte NL, Voskuhl RR: Immune modulation in multiple sclerosis patients treated with the pregnancy hormone estriol. J Immunol. 2003 Dec 1;171(11):6267-74. [PubMed:14634144 ]
Trimesta [Link]

Only showing the first 10 proteins. There are 31 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 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

Estriol + NAD → 16b-Hydroxyestrone + NADH + Hydrogen Ion	details
Estriol + NADP → 16b-Hydroxyestrone + NADPH + Hydrogen Ion	details

Enzyme Details

2. 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

Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronide	details

Enzyme Details

3. Estrogen receptor beta

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner. Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA- binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual
Gene Name:: ESR2
Uniprot ID:: Q92731
Molecular weight:: 59215.8

References

Mishra RG, Stanczyk FZ, Burry KA, Oparil S, Katzenellenbogen BS, Nealen ML, Katzenellenbogen JA, Hermsmeyer RK: Metabolite ligands of estrogen receptor-beta reduce primate coronary hyperreactivity. Am J Physiol Heart Circ Physiol. 2006 Jan;290(1):H295-303. Epub 2005 Sep 30. [PubMed:16199482 ]

Enzyme Details

4. 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

Estriol + NAD → 16b-Hydroxyestrone + NADH + Hydrogen Ion	details
Estriol + NADP → 16b-Hydroxyestrone + NADPH + Hydrogen Ion	details

Enzyme Details

5. 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

Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronide	details

Enzyme Details

6. 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

Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronide	details

Enzyme Details

7. 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

Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronide	details

Enzyme Details

8. 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

Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronide	details

Enzyme Details

9. UDP-glucuronosyltransferase 2B15

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 displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:: UGT2B15
Uniprot ID:: P54855
Molecular weight:: 61035.815

Reactions

Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronide	details

Enzyme Details

10. UDP-glucuronosyltransferase 2A1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:: UGT2A1
Uniprot ID:: Q9Y4X1
Molecular weight:: 60771.605

Reactions

Uridine diphosphate glucuronic acid + Estriol → Uridine 5'-diphosphate + Estriol-16-Glucuronide	details

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Kim WY, Benet LZ: P-glycoprotein (P-gp/MDR1)-mediated efflux of sex-steroid hormones and modulation of P-gp expression in vitro. Pharm Res. 2004 Jul;21(7):1284-93. [PubMed:15290871 ]

Enzyme Details

2. Solute carrier organic anion transporter family member 1A2

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:: SLCO1A2
Uniprot ID:: P46721
Molecular weight:: 74144.1

References

Kanai N, Lu R, Bao Y, Wolkoff AW, Vore M, Schuster VL: Estradiol 17 beta-D-glucuronide is a high-affinity substrate for oatp organic anion transporter. Am J Physiol. 1996 Feb;270(2 Pt 2):F326-31. [PubMed:8779894 ]

Only showing the first 10 proteins. There are 31 proteins in total.

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Showing metabocard for Estriol (HMDB0000153)

MOL for HMDB0000153 (Estriol)

3D MOL for HMDB0000153 (Estriol)

3D SDF for HMDB0000153 (Estriol)

3D-SDF for HMDB0000153 (Estriol)

PDB for HMDB0000153 (Estriol)

3D PDB for HMDB0000153 (Estriol)

SMILES for HMDB0000153 (Estriol)

INCHI for HMDB0000153 (Estriol)

Structure for HMDB0000153 (Estriol)

3D Structure for HMDB0000153 (Estriol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

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Transporters

References

References