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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-08-16 03:16:38 UTC
HMDB IDHMDB0000347
Secondary Accession Numbers
  • HMDB00347
Metabolite Identification
Common Name16b-Hydroxyestradiol
Description16b-Hydroxyestradiol is a hydroxylated metabolite of estradiol or estrone that has a hydroxyl group at C3-beta, 16-alpha, and 17-beta position. Estriol is a major urinary estrogen. During pregnancy, large amount of estriol is produced by the placenta. Isomers with inversion of the hydroxyl group or groups are called epiestriol.
Structure
Thumb
Synonyms
ValueSource
16-EpiestriolChEBI
16beta,17beta-EstriolChEBI
16beta-Hydroxy-17beta-estradiolChEBI
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
16b-Hydroxy-17b-estradiolGenerator
16β-hydroxy-17β-estradiolGenerator
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
16-Epi-estriolHMDB
16-EpiestratriolHMDB
(16alpha,17beta)-Estra-1,3,5(10)-triene-3,16,17-triolMeSH
(16beta,17beta)-Estra-1,3,5(10)-triene-3,16,17-triolMeSH
16 alpha Hydroxy estradiolMeSH
16-alpha-Hydroxy-estradiolMeSH
16alpha,17beta EstriolMeSH
16alpha,17beta-EstriolMeSH
16beta Hydroxy estradiolMeSH
16beta-Hydroxy-estradiolMeSH
EstriolMeSH
OvestinMeSH
Chemical FormulaC18H24O3
Average Molecular Weight288.3814
Monoisotopic Molecular Weight288.172544634
IUPAC Name(1S,10R,11S,13S,14R,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,13,14-triol
Traditional Name(1S,10R,11S,13S,14R,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]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
DescriptionThis compound 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
StatusDetected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity81.27 m3·mol-1ChemAxon
Polarizability32.91 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0290000000-c1aaa2c05e9fd0323ef6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-2900000000-3b5302633684d0176de2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-7900000000-1705b9f7f2b39ae9ba41View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected but not Quantified Not AvailableNot AvailableNormal details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB021970
    KNApSAcK IDNot Available
    Chemspider ID62155
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB0000347
    METLIN ID5336
    PubChem Compound68929
    PDB IDNot Available
    ChEBI 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. 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 ]
    2. 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 ]
    3. 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 ]