Showing metabocard for Estriol (BMDB0000153)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:20:15 UTC
Update Date2020-06-04 18:59:02 UTC
MCDB ID BMDB0000153
Secondary Accession Numbers
  • BMDB00153
Metabolite Identification
Common NameEstriol
DescriptionEstriol, also known as 16a,17b-estriol or ovestin, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, estriol is considered to be a steroid lipid molecule. Estriol is a drug which is used as a test to determine the general health of an unborn fetus. Estriol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Estriol participates in a number of enzymatic reactions, within cattle. In particular, Estriol can be biosynthesized from 16a-hydroxyestrone; which is mediated by the enzyme estradiol 17-beta-dehydrogenase 1. In addition, Estriol can be biosynthesized from estradiol; which is mediated by the enzyme cytochrome P450 3A5. In cattle, estriol is involved in the metabolic pathway called the estrone metabolism pathway. Estriol is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(16alpha,17beta)-Estra-1,3,5(10)-triene-3,16,17-triolChEBI
1,3,5(10)-Estratriene-3,16-alpha,17beta-triolChEBI
16alpha,17beta-EstriolChEBI
16alpha-HydroxyestradiolChEBI
3,16alpha,17beta-Trihydroxy-Delta(1,3,5)-estratrieneChEBI
Deuslon-aChEBI
EstrielChEBI
OestriolChEBI
TrihydroxyestrinChEBI
(16a,17b)-Estra-1,3,5(10)-triene-3,16,17-triolGenerator
(16Α,17β)-estra-1,3,5(10)-triene-3,16,17-triolGenerator
1,3,5(10)-Estratriene-3,16-a,17b-triolGenerator
1,3,5(10)-Estratriene-3,16-α,17β-triolGenerator
16a,17b-EstriolGenerator
16Α,17β-estriolGenerator
16a-HydroxyestradiolGenerator
16Α-hydroxyestradiolGenerator
3,16a,17b-Trihydroxy-delta(1,3,5)-estratrieneGenerator
3,16Α,17β-trihydroxy-δ(1,3,5)-estratrieneGenerator
3,16a,17b-Trihydroxy-δ(1,3,5)-estratrieneHMDB
13b-Methyl-1,3,5(10)-gonatriene-3,16a,17b-triolHMDB
16-alpha,17-beta-EstriolHMDB
16-alpha,17-beta-OestriolHMDB
16-alpha-HydroxyestradiolHMDB
16a-EstriolHMDB
16alpha,17beta-OestriolHMDB
16alpha-Hydroxy-17beta-estradiolHMDB
16alpha-HydroxyoestradiolHMDB
3,16a,17b-EstriolHMDB
3,16a,17b-Trihydroxyestra-1,3,5(10)-trieneHMDB
3,16alpha,17beta-Trihydroxy-1,3,5(10)-estratrieneHMDB
3,16alpha,17beta-Trihydroxyestra-1,3,5(10)-trieneHMDB
AacifemineHMDB
ColpogynHMDB
ColpovisterHMDB
DestriolHMDB
Deuslon aHMDB
Estra-1,3,5(10)-triene-3,16a,17b-triolHMDB
EstratriolHMDB
Follicular hormone hydrateHMDB
GynasanHMDB
HemostyptanonHMDB
Holin VHMDB
HormomedHMDB
IncurinHMDB
Klimax eHMDB
KlimoralHMDB
OekolpHMDB
OestratriolHMDB
OestriolumHMDB
OrestinHMDB
OrgastyptinHMDB
Ortho-gynestHMDB
OvesterinHMDB
OvestinHMDB
OvestinonHMDB
OvestrionHMDB
Ovo-vincesHMDB
TheelolHMDB
TridestrinHMDB
TriovexHMDB
16-alpha-Hydroxy-estradiolHMDB
(16beta,17beta)-Estra-1,3,5(10)-triene-3,16,17-triolHMDB
16beta Hydroxy estradiolHMDB
16beta-Hydroxy-estradiolHMDB
EpiestriolHMDB
16 alpha Hydroxy estradiolHMDB
16alpha,17beta EstriolHMDB
Estra-1,3,5(10)-triene-3,16beta,17beta-triolHMDB
13beta-Methyl-1,3,5(10)-gonatriene-3,16alpha,17beta-triolHMDB
13β-Methyl-1,3,5(10)-gonatriene-3,16α,17β-triolHMDB
16alpha-EstriolHMDB
16α-EstriolHMDB
3,16alpha,17beta-EstriolHMDB
3,16α,17β-EstriolHMDB
3,16α,17β-Trihydroxyestra-1,3,5(10)-trieneHMDB
EstriolHMDB
Chemical FormulaC18H24O3
Average Molecular Weight288.3814
Monoisotopic Molecular Weight288.172544634
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 Number50-27-1
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 KeyPROQIPRRNZUXQM-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.
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point282 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.45HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
Polarizability33.08 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-005a-1983000000-2f46d0d29b48132f76702014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4970000000-1aa2bbf3f32fd687c37d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-005a-1983000000-2f46d0d29b48132f76702017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-1390000000-492aa66975c4e026b9d82017-08-28View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-009i-2033900000-46c301a46b654b6c6bf32017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-5900000000-2102cb581ac98fea87b02012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-1900000000-1fab12be883127f80c672012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-5900000000-2102cb581ac98fea87b02012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-000i-4970000000-1aa2bbf3f32fd687c37d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0390000000-891430228022fb330b422017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-7ce66600861479086f4f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-000i-1970000000-6d5c77ab4f1744109b862021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-331480c31f6585f70cf22021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0zg0-0590000000-6ee9bd7dbdbd777f46a42021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2900000000-d7ae7d481cc02d1ab8392021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2920000000-d7d95b3d24e7be97e8482021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-3aa436f48e23664bd4552021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-b047d204e97271aa8a652017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0490000000-c0c0bd8b1dc1381c06fa2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-3950000000-b7180dbe548021fd7fc92017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-743915792d6f69593b2b2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-8469d578b4631e8de9952017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02p0-0190000000-738399876b56d0e183d52017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-843a74fabb1d0eb512a12021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0090000000-4e0854fb8be9cf34de972021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02br-0090000000-70686fa9219ae093945a2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-1126a56061a8c854c7552021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fga-0790000000-a1dba0b6195890b30d912021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6v-3910000000-64d9abb8f215c1264e1f2021-09-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-3950000000-c2f0781bc5056d66aaf52014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Not Available2012-12-04View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.00003 +/- 0.00001 uM details
Detected and Quantified0.00003 +/- 0.00001 uM details
HMDB IDHMDB0000153
DrugBank IDDB04573
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006781
KNApSAcK IDNot Available
Chemspider ID5553
KEGG Compound IDC05141
BioCyc IDESTRIOL
BiGG ID45207
Wikipedia LinkEstriol
METLIN ID2581
PubChem Compound5756
PDB IDNot Available
ChEBI ID27974
References
Synthesis ReferenceLeeds, 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
  1. Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3. [PubMed:512140 ]