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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:00 UTC
HMDB IDHMDB0000356
Secondary Accession Numbers
  • HMDB00356
Metabolite Identification
Common Name17-Epiestriol
Description17-Epiestriol, also known as 17alpha-estriol, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 17-epiestriol is considered to be a steroid lipid molecule. 17-Epiestriol is a hydroxylated metabolite of estradiol or estrone that has a hydroxyl group at the C3-beta, 16-alpha, and 17-beta positions. Estriol is a major urinary estrogen. During pregnancy, a large amount of estriol is produced by the placenta. Isomers with inversion of the hydroxyl group or groups are called epiestriol.
Structure
Data?1599233951
Synonyms
ValueSource
(16alpha,17alpha)-Estra-1(10),2,4-triene-3,16,17-triolChEBI
(8R,9S,13S,14S,16R,17S)-13-Methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,16,17-triolChEBI
1,3,5(10)-Estratriene-3,16alpha,17alpha-triolChEBI
16alpha,17alpha-EstriolChEBI
16alpha-Hydroxy-17alpha-estradiolChEBI
17alpha-EstriolChEBI
3,16alpha,17alpha-Trihydroxy-1,3,5(10)-estratrieneChEBI
(16a,17a)-Estra-1(10),2,4-triene-3,16,17-triolGenerator
(16Α,17α)-estra-1(10),2,4-triene-3,16,17-triolGenerator
1,3,5(10)-Estratriene-3,16a,17a-triolGenerator
1,3,5(10)-Estratriene-3,16α,17α-triolGenerator
16a,17a-EstriolGenerator
16Α,17α-estriolGenerator
16a-Hydroxy-17a-estradiolGenerator
16Α-hydroxy-17α-estradiolGenerator
17a-EstriolGenerator
17Α-estriolGenerator
3,16a,17a-Trihydroxy-1,3,5(10)-estratrieneGenerator
3,16Α,17α-trihydroxy-1,3,5(10)-estratrieneGenerator
(16a,17a)-Estra-1,3,5(10)-triene-3,16,17-triolHMDB
(16Α,17α)-estra-1,3,5(10)-triene-3,16,17-triolHMDB
(16alpha,17alpha)-Estra-1,3,5(10)-triene-3,16,17-triolHMDB
17-Epi-estriolHMDB
17alpha-EpiestriolHMDB
17Α-epiestriolHMDB
Estra-1,3,5(10)-triene-3,16alpha,17alpha-triolHMDB
Estra-1,3,5(10)-triene-3,16α,17α-triolHMDB
17-EpiestriolChEMBL
Chemical FormulaC18H24O3
Average Molecular Weight288.3814
Monoisotopic Molecular Weight288.172544634
IUPAC Name(1S,10R,11S,13R,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,13,14-triol
Traditional Name(1S,10R,11S,13R,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-triene-5,13,14-triol
CAS Registry Number1228-72-4
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 KeyPROQIPRRNZUXQM-PNVOZDDCSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens 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 FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.54ALOGPS
logP2.67ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity81.27 m³·mol⁻¹ChemAxon
Polarizability32.95 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-211.25130932474
DeepCCS[M+Na]+186.04230932474
AllCCS[M+H]+171.732859911
AllCCS[M+H-H2O]+168.532859911
AllCCS[M+NH4]+174.732859911
AllCCS[M+Na]+175.632859911
AllCCS[M-H]-176.032859911
AllCCS[M+Na-2H]-175.932859911
AllCCS[M+HCOO]-175.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
17-Epiestriol[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=C33943.9Standard polar33892256
17-Epiestriol[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=C32917.3Standard non polar33892256
17-Epiestriol[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=C32941.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
17-Epiestriol,1TMS,isomer #1C[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]2O2789.2Semi standard non polar33892256
17-Epiestriol,1TMS,isomer #2C[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)C2794.1Semi standard non polar33892256
17-Epiestriol,1TMS,isomer #3C[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]2O2771.9Semi standard non polar33892256
17-Epiestriol,2TMS,isomer #1C[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]2O2842.9Semi standard non polar33892256
17-Epiestriol,2TMS,isomer #2C[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)C2782.1Semi standard non polar33892256
17-Epiestriol,2TMS,isomer #3C[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)C2842.9Semi standard non polar33892256
17-Epiestriol,3TMS,isomer #1C[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)C2907.4Semi standard non polar33892256
17-Epiestriol,1TBDMS,isomer #1CC(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]1O3065.1Semi standard non polar33892256
17-Epiestriol,1TBDMS,isomer #2CC(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@]12C3081.3Semi standard non polar33892256
17-Epiestriol,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@H](O)[C@H](O)C[C@@H]123084.3Semi standard non polar33892256
17-Epiestriol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]123374.5Semi standard non polar33892256
17-Epiestriol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@]12C3303.1Semi standard non polar33892256
17-Epiestriol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C[C@@H]123391.4Semi standard non polar33892256
17-Epiestriol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]123664.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 17-Epiestriol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-1390000000-492aa66975c4e026b9d82017-09-07Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Epiestriol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Epiestriol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Epiestriol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Epiestriol GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Epiestriol GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Epiestriol GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Epiestriol GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Epiestriol GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Epiestriol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Epiestriol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Epiestriol GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Epiestriol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Epiestriol GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Epiestriol GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17-Epiestriol GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Epiestriol 10V, Positive-QTOFsplash10-000i-0190000000-b047d204e97271aa8a652017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Epiestriol 20V, Positive-QTOFsplash10-00dr-0490000000-c0c0bd8b1dc1381c06fa2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Epiestriol 40V, Positive-QTOFsplash10-0ufr-3950000000-b7180dbe548021fd7fc92017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Epiestriol 10V, Negative-QTOFsplash10-000i-0090000000-743915792d6f69593b2b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Epiestriol 20V, Negative-QTOFsplash10-000i-0090000000-8469d578b4631e8de9952017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Epiestriol 40V, Negative-QTOFsplash10-02p0-0190000000-738399876b56d0e183d52017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Epiestriol 10V, Positive-QTOFsplash10-000i-0090000000-1126a56061a8c854c7552021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Epiestriol 20V, Positive-QTOFsplash10-0fga-0790000000-a1dba0b6195890b30d912021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Epiestriol 40V, Positive-QTOFsplash10-0a6v-3910000000-64d9abb8f215c1264e1f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Epiestriol 10V, Negative-QTOFsplash10-000i-0090000000-843a74fabb1d0eb512a12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Epiestriol 20V, Negative-QTOFsplash10-00kr-0090000000-4e0854fb8be9cf34de972021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17-Epiestriol 40V, Negative-QTOFsplash10-02br-0090000000-70686fa9219ae093945a2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB07702
Phenol Explorer Compound IDNot Available
FooDB IDFDB021978
KNApSAcK IDNot Available
Chemspider ID225189
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link17-epiestriol
METLIN ID5345
PubChem Compound256737
PDB IDNot Available
ChEBI ID42156
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBreuer, Heinz. Isolation of 17-epiestriol from the urine of pregnant women. Nature (London, United Kingdom) (1960), 185 613-14.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lee SH, Nam SY, Chung BC: Altered profile of endogenous steroids in the urine of patients with prolactinoma. Clin Biochem. 1998 Oct;31(7):529-35. [PubMed:9812172 ]
  2. Xu X, Veenstra TD, Fox SD, Roman JM, Issaq HJ, Falk R, Saavedra JE, Keefer LK, Ziegler RG: Measuring fifteen endogenous estrogens simultaneously in human urine by high-performance liquid chromatography-mass spectrometry. Anal Chem. 2005 Oct 15;77(20):6646-54. [PubMed:16223252 ]