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Showing metabocard for 16b-Hydroxyestrone (HMDB0000313)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
enzymes (6) Show 6 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:03 UTC
HMDB IDHMDB0000313
Secondary Accession Numbers
  • HMDB00313
Metabolite Identification
Common Name16b-Hydroxyestrone
Description16b-Hydroxyestrone belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 16b-hydroxyestrone is considered to be a steroid lipid molecule. 16b-Hydroxyestrone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752123
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(16beta)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-oneChEBI
16-HydroxyestroneChEBI
3,16-Dihydroxyestra-1,3,5(10)-trien-17-oneChEBI
3,16beta-Dihydroxy-estra-1,3,5(10)-trien-17-oneChEBI
(16b)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-oneGenerator
(16Β)-3,16-dihydroxyestra-1,3,5(10)-trien-17-oneGenerator
3,16b-Dihydroxy-estra-1,3,5(10)-trien-17-oneGenerator
3,16Β-dihydroxy-estra-1,3,5(10)-trien-17-oneGenerator
16alpha-HydroxyestroneHMDB
16beta-HydroxyestroneHMDB
3,16-Dihydroxy-estra-1,3,5(10)-trien-17-oneHMDB
16 alpha-HydroxyestroneHMDB
16 beta-HydroxyestroneHMDB
16-alpha-HydroxyestroneHMDB
Chemical FormulaC18H22O3
Average Molecular Weight286.3655
Monoisotopic Molecular Weight286.15689457
IUPAC Name(1S,10R,11S,13S,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one
Traditional Name16 α-hydroxyestrone
CAS Registry Number966-06-3
SMILES
[H][C@@]12C[C@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3
InChI Identifier
InChI=1S/C18H22O3/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/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,18+/m1/s1
InChI KeyWPOCIZJTELRQMF-LFRCEIEQSA-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
  • Hydroxysteroid
  • 17-oxosteroid
  • Oxosteroid
  • 16-beta-hydroxysteroid
  • 16-hydroxysteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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 Solubility0.047 g/LALOGPS
logP2.45ALOGPS
logP3.44ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity80.57 m³·mol⁻¹ChemAxon
Polarizability32.29 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-2690000000-4da4066a9998d4bb7152Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-016r-3279600000-35209b189461208c9804Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-ea49b0e7c1a26f8807b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-0490000000-7a9632ca2f7369b28ad3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-7980000000-f674402195ec376faeb7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-91f32a5e866ea149a4a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-f8524ff8a5fae66251adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02dl-1090000000-5ac386a35fc2bb3cc1f0Spectrum
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021940
KNApSAcK IDNot Available
Chemspider ID17215934
KEGG Compound IDC05300
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5302
PubChem Compound22833517
PDB IDNot Available
ChEBI ID87628
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceBiggerstaff, W. R.; Gallagher, T. F. 3,16b-Dihydroxy-1,3,5-estratrien-17-one and related compounds. Journal of Organic Chemistry (1957), 22 1220-2.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yokoyama K, Tajima M, Yoshida H, Nakayama M, Tokutome G, Sakagami H, Hosoya T: Plasma pteridine concentrations in patients with chronic renal failure. Nephrol Dial Transplant. 2002 Jun;17(6):1032-6. [PubMed:12032193 ]

Enzymes

Enzyme Details
1. Estradiol 17-beta-dehydrogenase 2
General function:
Involved in oxidoreductase activity
Specific function:
Capable of catalyzing the interconversion of testosterone and androstenedione, as well as estradiol and estrone. Also has 20-alpha-HSD activity. Uses NADH while EDH17B3 uses NADPH.
Gene Name:
HSD17B2
Uniprot ID:
P37059
Molecular weight:
42784.75
Reactions
Estriol + NAD → 16b-Hydroxyestrone + NADH + Hydrogen Iondetails
Estriol + NADP → 16b-Hydroxyestrone + NADPH + Hydrogen Iondetails
Enzyme Details
2. Estradiol 17-beta-dehydrogenase 8
General function:
Involved in oxidoreductase activity
Specific function:
NAD-dependent 17-beta-hydroxysteroid dehydrogenase with highest activity towards estradiol. Has very low activity towards testosterone. The heteroteramer with CBR4 has NADH-dependent 3-ketoacyl-acyl carrier protein reductase activity. May play a role in biosynthesis of fatty acids in mitochondria.
Gene Name:
HSD17B8
Uniprot ID:
Q92506
Molecular weight:
26973.56
Reactions
Estriol + NAD → 16b-Hydroxyestrone + NADH + Hydrogen Iondetails
Estriol + NADP → 16b-Hydroxyestrone + NADPH + Hydrogen Iondetails
Enzyme Details
3. Estradiol 17-beta-dehydrogenase 1
General function:
Involved in estradiol 17-beta-dehydrogenase activity
Specific function:
Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH.
Gene Name:
HSD17B1
Uniprot ID:
P14061
Molecular weight:
34949.715
Reactions
Estriol + NAD → 16b-Hydroxyestrone + NADH + Hydrogen Iondetails
Estriol + NADP → 16b-Hydroxyestrone + NADPH + Hydrogen Iondetails
Enzyme Details
4. 3-keto-steroid reductase
General function:
Involved in oxidoreductase activity
Specific function:
Responsible for the reduction of the keto group on the C-3 of sterols.
Gene Name:
HSD17B7
Uniprot ID:
P56937
Molecular weight:
38205.77
Reactions
Estriol + NAD → 16b-Hydroxyestrone + NADH + Hydrogen Iondetails
Estriol + NADP → 16b-Hydroxyestrone + NADPH + Hydrogen Iondetails
Enzyme Details
5. 17-beta-hydroxysteroid dehydrogenase type 6
General function:
Involved in oxidoreductase activity
Specific function:
NAD-dependent oxidoreductase with broad substrate specificity that shows both oxidative and reductive activity (in vitro). Has 17-beta-hydroxysteroid dehydrogenase activity towards various steroids (in vitro). Converts 5-alpha-androstan-3-alpha,17-beta-diol to androsterone and estradiol to estrone (in vitro). Has 3-alpha-hydroxysteroid dehydrogenase activity towards androsterone (in vitro). Has retinol dehydrogenase activity towards all-trans-retinol (in vitro). Can convert androsterone to epi-androsterone. Androsterone is first oxidized to 5-alpha-androstane-3,17-dione and then reduced to epi-andosterone. Can act on both C-19 and C-21 3-alpha-hydroxysteroids.
Gene Name:
HSD17B6
Uniprot ID:
O14756
Molecular weight:
35965.41
Reactions
Estriol + NAD → 16b-Hydroxyestrone + NADH + Hydrogen Iondetails
Estriol + NADP → 16b-Hydroxyestrone + NADPH + Hydrogen Iondetails
Enzyme Details
6. Estradiol 17-beta-dehydrogenase 12
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of estrone (E1) into estradiol (E2), suggesting a central role in estrogen formation. Its strong expression in ovary and mammary gland suggest that it may constitute the major enzyme responsible for the conversion of E1 to E2 in women. Also has 3-ketoacyl-CoA reductase activity, reducing both long chain 3-ketoacyl-CoAs and long chain fatty acyl-CoAs, suggesting a role in long fatty acid elongation.
Gene Name:
HSD17B12
Uniprot ID:
Q53GQ0
Molecular weight:
34323.875
Reactions
Estriol + NAD → 16b-Hydroxyestrone + NADH + Hydrogen Iondetails
Estriol + NADP → 16b-Hydroxyestrone + NADPH + Hydrogen Iondetails