Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:02 UTC
HMDB IDHMDB0000431
Secondary Accession Numbers
  • HMDB00431
Metabolite Identification
Common Name16,17-Epiestriol
Description16,17-Epiestriol, also known as trans-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, 16,17-epiestriol is considered to be a steroid. Based on a literature review very few articles have been published on 16,17-Epiestriol.
Structure
Data?1582752131
Synonyms
ValueSource
1617-EpiestriolHMDB
16,17-Epi-estriolHMDB
16b,17a-EstriolHMDB
16b-Hydroxy-17a-estradiolHMDB
Estra-1,3,5(10)-triene-3,16b,17a-triolHMDB
trans-EstriolHMDB
Chemical FormulaC18H24O3
Average Molecular Weight288.3814
Monoisotopic Molecular Weight288.172544634
IUPAC Name(1S,10R,11S,13S,14S,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,13,14-triol
Traditional Name16,17-epiestriol
CAS Registry Number793-89-5
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-LMMHAMTPSA-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-beta-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 Point766.40 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-1.456 (est)The Good Scents Company Information System
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
DarkChem[M+H]+169.1131661259
DarkChem[M-H]-166.72431661259
AllCCS[M+H]+171.74932859911
AllCCS[M-H]-176.04132859911
DeepCCS[M-2H]-213.73330932474
DeepCCS[M+Na]+188.530932474
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
16,17-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
16,17-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
16,17-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
16,17-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
16,17-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
16,17-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
16,17-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
16,17-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
16,17-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
16,17-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
16,17-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
16,17-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
16,17-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
16,17-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
16,17-Epiestriol,2TBDMS,isomer #2CC(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)C3303.1Semi standard non polar33892256
16,17-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
16,17-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 - 16,17-Epiestriol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-1590000000-cf2f42c37e3436edbcfa2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16,17-Epiestriol GC-MS (3 TMS) - 70eV, Positivesplash10-009i-2033900000-46c301a46b654b6c6bf32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16,17-Epiestriol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16,17-Epiestriol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16,17-Epiestriol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16,17-Epiestriol GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16,17-Epiestriol GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16,17-Epiestriol GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16,17-Epiestriol GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16,17-Epiestriol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16,17-Epiestriol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16,17-Epiestriol GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16,17-Epiestriol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16,17-Epiestriol GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16,17-Epiestriol GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16,17-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 - 16,17-Epiestriol 10V, Positive-QTOFsplash10-000i-0090000000-11e0a31c4649eeadffb42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16,17-Epiestriol 20V, Positive-QTOFsplash10-0fki-0490000000-4179a69250f74019b4f82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16,17-Epiestriol 40V, Positive-QTOFsplash10-0fvi-4970000000-09555c37e0926cc7a8452017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16,17-Epiestriol 10V, Negative-QTOFsplash10-000i-0090000000-78e3342aed99bfff39702017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16,17-Epiestriol 20V, Negative-QTOFsplash10-000i-0090000000-66743ac1a583b78756a72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16,17-Epiestriol 40V, Negative-QTOFsplash10-062l-0090000000-a38189a9216fbf580f8c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16,17-Epiestriol 10V, Positive-QTOFsplash10-000i-0090000000-1126a56061a8c854c7552021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16,17-Epiestriol 20V, Positive-QTOFsplash10-0fga-0790000000-a1dba0b6195890b30d912021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16,17-Epiestriol 40V, Positive-QTOFsplash10-0a6v-3910000000-64d9abb8f215c1264e1f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16,17-Epiestriol 10V, Negative-QTOFsplash10-000i-0090000000-843a74fabb1d0eb512a12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16,17-Epiestriol 20V, Negative-QTOFsplash10-00kr-0090000000-4e0854fb8be9cf34de972021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16,17-Epiestriol 40V, Negative-QTOFsplash10-02br-0090000000-70686fa9219ae093945a2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022041
KNApSAcK IDNot Available
Chemspider ID13628086
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link16β,17α-Epiestriol
METLIN ID5420
PubChem Compound21252247
PDB IDNot Available
ChEBI ID1150237
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1682491
References
Synthesis ReferenceBreuer, H.; Pangels, Gerta. Isolation of 17-epiestriol and 16,17-epiestriol from the urine of pregnant women. Z. physiol. Chem. (1960), 322 177-83.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pierrat G, Prost M, Lavoue G, Lumbroso C: [Use of an ion exchanger as a rapid means of extraction, applied to the determination of urinary estrogens and pregnanediol in pregnancy, using colorimetry or gas chromatography]. Ann Biol Clin (Paris). 1976;34(6):423-30. [PubMed:1030927 ]