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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:00 UTC
HMDB IDHMDB0000347
Secondary Accession Numbers
  • HMDB00347
Metabolite Identification
Common Name16b-Hydroxyestradiol
Description16b-Hydroxyestradiol, which is better known as epiestriol (or 16beta-epiestriol or 16beta-hydroxy-17beta-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, epiestriol is considered to be a steroid molecule. Formally 16b-hydroxyestradiol is a 3-hydroxy steroid that is 17beta-estradiol substituted by a beta-hydroxy group at position 16. In other words, it has hydroxyl groups at the C3, 16-beta, and 17-beta positions. It is an oxidative metabolite of 17beta-estradiol (PMID: 12865317 ). Epiestriol is found in all vertebrates. Epiestriol is a minor and weak endogenous estrogen. It is the 16beta-epimer of estriol (which is 16alpha-hydroxy-17beta-estradiol). Epiestriol has been used clinically in the treatment of acne. In addition to its estrogenic actions, epiestriol has been found to possess significant anti-inflammatory properties without glycogenic activity or immunosuppressive effects (PMID: 9120824 ).
Structure
Data?1582752125
Synonyms
ValueSource
16-EpiestriolChEBI
16beta,17beta-EstriolChEBI
ActriolChEBI
EpiestriolChEBI
EpiestriolumChEBI
EpioestriolumChEBI
Estra-1,3,5(10)-triene-3,16beta,17-triolChEBI
Estra-1,3,5(10)-triene-3,16beta,17beta-triolChEBI
16b,17b-EstriolGenerator
16Β,17β-estriolGenerator
Estra-1,3,5(10)-triene-3,16b,17-triolGenerator
Estra-1,3,5(10)-triene-3,16β,17-triolGenerator
Estra-1,3,5(10)-triene-3,16b,17b-triolGenerator
Estra-1,3,5(10)-triene-3,16β,17β-triolGenerator
16beta-Hydroxy-17beta-estradiolHMDB
16b-Hydroxy-17b-estradiolHMDB
16Β-hydroxy-17β-estradiolHMDB
16-Epi-estriolHMDB
16-EpiestratriolHMDB
(16alpha,17beta)-Estra-1,3,5(10)-triene-3,16,17-triolHMDB
(16beta,17beta)-Estra-1,3,5(10)-triene-3,16,17-triolHMDB
16 alpha Hydroxy estradiolHMDB
16-alpha-Hydroxy-estradiolHMDB
16alpha,17beta EstriolHMDB
16alpha,17beta-EstriolHMDB
16beta Hydroxy estradiolHMDB
16beta-Hydroxy-estradiolHMDB
EstriolHMDB
OvestinHMDB
16Β-hydroxyestradiolHMDB
16b-HydroxyestradiolGenerator
Chemical FormulaC18H24O3
Average Molecular Weight288.3814
Monoisotopic Molecular Weight288.172544634
IUPAC Name(1S,10R,11S,13S,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,13S,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 Number547-81-9
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-ZMSHIADSSA-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
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available153.573http://allccs.zhulab.cn/database/detail?ID=AllCCS00001228
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
Polarizability33.05 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]+168.84731661259
DarkChem[M-H]-166.19831661259
AllCCS[M+H]+171.4232859911
AllCCS[M-H]-175.98832859911
DeepCCS[M-2H]-213.80730932474
DeepCCS[M+Na]+188.62630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
16b-Hydroxyestradiol[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
16b-Hydroxyestradiol[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
16b-Hydroxyestradiol[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
16b-Hydroxyestradiol,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
16b-Hydroxyestradiol,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
16b-Hydroxyestradiol,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
16b-Hydroxyestradiol,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
16b-Hydroxyestradiol,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
16b-Hydroxyestradiol,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
16b-Hydroxyestradiol,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
16b-Hydroxyestradiol,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
16b-Hydroxyestradiol,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@@]21C3081.3Semi standard non polar33892256
16b-Hydroxyestradiol,1TBDMS,isomer #3CC(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]2O3084.3Semi standard non polar33892256
16b-Hydroxyestradiol,2TBDMS,isomer #1CC(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]2O3374.5Semi standard non polar33892256
16b-Hydroxyestradiol,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
16b-Hydroxyestradiol,2TBDMS,isomer #3CC(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)C3391.4Semi standard non polar33892256
16b-Hydroxyestradiol,3TBDMS,isomer #1CC(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)C3664.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-1590000000-cf2f42c37e3436edbcfa2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (3 TMS) - 70eV, Positivesplash10-009i-2033900000-46c301a46b654b6c6bf32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestradiol GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 16b-Hydroxyestradiol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-0290000000-c1aaa2c05e9fd0323ef62012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 16b-Hydroxyestradiol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4i-2900000000-3b5302633684d0176de22012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 16b-Hydroxyestradiol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0a4i-7900000000-1705b9f7f2b39ae9ba412012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 10V, Positive-QTOFsplash10-000i-0090000000-11e0a31c4649eeadffb42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 20V, Positive-QTOFsplash10-0fki-0490000000-4179a69250f74019b4f82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 40V, Positive-QTOFsplash10-0fvi-4970000000-09555c37e0926cc7a8452017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 10V, Negative-QTOFsplash10-000i-0090000000-78e3342aed99bfff39702017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 20V, Negative-QTOFsplash10-000i-0090000000-66743ac1a583b78756a72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 40V, Negative-QTOFsplash10-062l-0090000000-a38189a9216fbf580f8c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 10V, Negative-QTOFsplash10-000i-0090000000-843a74fabb1d0eb512a12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 20V, Negative-QTOFsplash10-00kr-0090000000-4e0854fb8be9cf34de972021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 40V, Negative-QTOFsplash10-02br-0090000000-70686fa9219ae093945a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 10V, Positive-QTOFsplash10-000i-0090000000-1126a56061a8c854c7552021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 20V, Positive-QTOFsplash10-0fga-0790000000-a1dba0b6195890b30d912021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestradiol 40V, Positive-QTOFsplash10-0a6v-3910000000-64d9abb8f215c1264e1f2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021970
KNApSAcK IDNot Available
Chemspider ID62155
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5336
PubChem Compound68929
PDB IDNot Available
ChEBI ID87620
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceLing, Yangzhi; Xu, Chunfang; Fang, Guofu; Liu, Weiqin. Improved synthesis of estriol via hydroboration. Yiyao Gongye (1988), 19(12), 533-5.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lee AJ, Cai MX, Thomas PE, Conney AH, Zhu BT: Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology. 2003 Aug;144(8):3382-98. [PubMed:12865317 ]
  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 ]
  3. Nambara T, Matsuki Y, Igarashi J, Kawarada Y, Kurata M: Studies on steroid conjugates. XII. Occurrence of 16-epiestriol 16-glucuronide in human pregnancy urine. Chem Pharm Bull (Tokyo). 1974 Oct;22(10):2242-5. [PubMed:4377544 ]
  4. Adlercreutz H, Martin F, Pulkkinen M, Dencker H, Rimer U, Sjoberg NO, Tikkanen MJ: Intestinal metabolism of estrogens. J Clin Endocrinol Metab. 1976 Sep;43(3):497-505. [PubMed:956337 ]
  5. Latman NS, Kishore V, Bruot BC: 16-epiestriol: an anti-inflammatory steroid without glycogenic activity. J Pharm Sci. 1994 Jun;83(6):874-7. doi: 10.1002/jps.2600830623. [PubMed:9120824 ]