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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:39:09 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
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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.047 g/LALOGPS
logP10(2.45) g/LALOGPS
logP10(3.44) g/LChemAxon
logS10(-3.8) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.72131661259
DarkChem[M-H]-166.19931661259
AllCCS[M+H]+169.91132859911
AllCCS[M-H]-175.54132859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
16b-Hydroxyestrone,1TMS,#1C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1C[C@H](O[Si](C)(C)C)C2=O2768.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
16b-Hydroxyestrone,1TMS,#2C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C[C@H](O)C2=O2786.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
16b-Hydroxyestrone,1TMS,#3C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1CC(O)=C2O[Si](C)(C)C2768.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
16b-Hydroxyestrone,2TMS,#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)C2=O2875.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
16b-Hydroxyestrone,2TMS,#2C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C2779.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
16b-Hydroxyestrone,2TMS,#3C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC(O)=C2O[Si](C)(C)C2839.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
16b-Hydroxyestrone,1TBDMS,#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)C1=O3049.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
16b-Hydroxyestrone,1TBDMS,#2CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)[C@@H](O)C[C@@H]123088.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
16b-Hydroxyestrone,1TBDMS,#3CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@]12C3043.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
16b-Hydroxyestrone,2TBDMS,#1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]123412.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
16b-Hydroxyestrone,2TBDMS,#2CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]2C13287.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
16b-Hydroxyestrone,2TBDMS,#3CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]12C3331.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-2690000000-4da4066a9998d4bb71522017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (2 TMS) - 70eV, Positivesplash10-016r-3279600000-35209b189461208c98042017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 10V, Positive-QTOFsplash10-000i-0090000000-ea49b0e7c1a26f8807b32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 20V, Positive-QTOFsplash10-0ap0-0490000000-7a9632ca2f7369b28ad32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 40V, Positive-QTOFsplash10-0gb9-7980000000-f674402195ec376faeb72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 10V, Negative-QTOFsplash10-000i-0090000000-91f32a5e866ea149a4a42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 20V, Negative-QTOFsplash10-000i-0090000000-f8524ff8a5fae66251ad2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 40V, Negative-QTOFsplash10-02dl-1090000000-5ac386a35fc2bb3cc1f02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 10V, Positive-QTOFsplash10-000i-0090000000-8269f9806e3a6460adb92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 20V, Positive-QTOFsplash10-00ks-0590000000-2d8e09d2baef368efec12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 40V, Positive-QTOFsplash10-00dj-0920000000-bce8e0246e58d9e59bbd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 10V, Negative-QTOFsplash10-000i-0090000000-fcaf0435bbf678a207f72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 20V, Negative-QTOFsplash10-000i-0090000000-48bccddc063fe7e2f9982021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 40V, Negative-QTOFsplash10-02di-0090000000-080f7d164203318ad3382021-09-22Wishart LabView Spectrum
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 IDNot Available
Good Scents IDNot Available
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

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
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
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
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
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
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