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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:01 UTC
HMDB IDHMDB0000372
Secondary Accession Numbers
  • HMDB00372
Metabolite Identification
Common Name16-Oxoestrone
DescriptionEstrone (also oestrone) is an estrogenic hormone secreted by the ovary. Its molecular formula is C18H22O2. estrone has a melting point of 254.5 degrees Celsius. estrone is one of the three estrogens, which also include estriol and estradiol. estrone is the least prevalent of the three hormones, estradiol being prevalent almost always in a female body, estriol being prevalent primarily during pregnancy. estrone sulfate is relevant to health and disease due to its conversion to estrone sulfate, a long-lived derivative of estrone. estrone sulfate acts as a pool of estrone which can be converted as needed to the more active estradiol.
Structure
Data?1582752127
Synonyms
ValueSource
16-KetoestroneHMDB
3-Hydroxy-1,3,5(10)-estratriene-16,17-dioneHMDB
Chemical FormulaC18H20O3
Average Molecular Weight284.3496
Monoisotopic Molecular Weight284.141244506
IUPAC Name(15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-13,14-dione
Traditional Name(15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-13,14-dione
CAS Registry Number1228-73-5
SMILES
C[C@]12CCC3C(CCC4=C3C=CC(O)=C4)C1CC(=O)C2=O
InChI Identifier
InChI=1S/C18H20O3/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/h3,5,8,13-15,19H,2,4,6-7,9H2,1H3/t13?,14?,15?,18-/m0/s1
InChI KeyANPHVANSJXDRTP-VLVBFLKRSA-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
  • 16-oxosteroid
  • 17-oxosteroid
  • Oxosteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Ketone
  • Cyclic ketone
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point231 - 235 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP2.86ALOGPS
logP4.15ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.83 m³·mol⁻¹ChemAxon
Polarizability31.49 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]+167.68631661259
DarkChem[M-H]-163.42131661259
AllCCS[M+H]+168.61432859911
AllCCS[M-H]-174.94732859911
DeepCCS[M-2H]-202.52430932474
DeepCCS[M+Na]+177.85630932474
AllCCS[M+H]+168.632859911
AllCCS[M+H-H2O]+165.232859911
AllCCS[M+NH4]+171.732859911
AllCCS[M+Na]+172.632859911
AllCCS[M-H]-174.932859911
AllCCS[M+Na-2H]-174.632859911
AllCCS[M+HCOO]-174.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
16-OxoestroneC[C@]12CCC3C(CCC4=C3C=CC(O)=C4)C1CC(=O)C2=O3743.4Standard polar33892256
16-OxoestroneC[C@]12CCC3C(CCC4=C3C=CC(O)=C4)C1CC(=O)C2=O2528.0Standard non polar33892256
16-OxoestroneC[C@]12CCC3C(CCC4=C3C=CC(O)=C4)C1CC(=O)C2=O2858.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
16-Oxoestrone,1TMS,isomer #1C[C@]12CCC3C4=CC=C(O[Si](C)(C)C)C=C4CCC3C1CC(=O)C2=O2840.0Semi standard non polar33892256
16-Oxoestrone,1TMS,isomer #2C[C@]12CCC3C4=CC=C(O)C=C4CCC3C1C=C(O[Si](C)(C)C)C2=O2786.0Semi standard non polar33892256
16-Oxoestrone,2TMS,isomer #1C[C@]12CCC3C4=CC=C(O[Si](C)(C)C)C=C4CCC3C1C=C(O[Si](C)(C)C)C2=O2821.2Semi standard non polar33892256
16-Oxoestrone,2TMS,isomer #1C[C@]12CCC3C4=CC=C(O[Si](C)(C)C)C=C4CCC3C1C=C(O[Si](C)(C)C)C2=O2729.0Standard non polar33892256
16-Oxoestrone,2TMS,isomer #1C[C@]12CCC3C4=CC=C(O[Si](C)(C)C)C=C4CCC3C1C=C(O[Si](C)(C)C)C2=O3087.1Standard polar33892256
16-Oxoestrone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CCC1C2CC[C@]2(C)C(=O)C(=O)CC123080.5Semi standard non polar33892256
16-Oxoestrone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2C3CCC4=CC(O)=CC=C4C3CC[C@]2(C)C1=O3074.9Semi standard non polar33892256
16-Oxoestrone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4C3CC[C@]2(C)C1=O3343.8Semi standard non polar33892256
16-Oxoestrone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4C3CC[C@]2(C)C1=O3181.7Standard non polar33892256
16-Oxoestrone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4C3CC[C@]2(C)C1=O3317.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoestrone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-0970000000-c33450029c2a510fb1dd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoestrone GC-MS (1 TMS) - 70eV, Positivesplash10-0032-1095000000-28ce684570c9033f6ecb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoestrone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoestrone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoestrone GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoestrone GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoestrone GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoestrone 10V, Positive-QTOFsplash10-000i-0090000000-6d759bc421714d0d29202017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoestrone 20V, Positive-QTOFsplash10-0a4r-0390000000-d8c66380533ac80c418f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoestrone 40V, Positive-QTOFsplash10-0gdi-7980000000-4a05c980006c31f9644c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoestrone 10V, Negative-QTOFsplash10-001i-0090000000-71415abfa8ce5bdff3d32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoestrone 20V, Negative-QTOFsplash10-001i-0090000000-66dbf6c2ee8a27f150f22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoestrone 40V, Negative-QTOFsplash10-0gdi-1090000000-dd632ccd4b6912edb4b72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoestrone 10V, Negative-QTOFsplash10-001i-0090000000-78a425e25a58a7330ede2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoestrone 20V, Negative-QTOFsplash10-001i-0090000000-ea975f2e73cc3dfd69ff2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoestrone 40V, Negative-QTOFsplash10-01sl-0390000000-45c573c062efce8ba0452021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoestrone 10V, Positive-QTOFsplash10-000i-0090000000-5bc7bcd7c5f2680941202021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoestrone 20V, Positive-QTOFsplash10-004r-0590000000-13c3647f4ba51b6998ee2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoestrone 40V, Positive-QTOFsplash10-004i-1790000000-7983b1aed115bbdf442d2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Liver
  • Placenta
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 IDFDB021991
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC14441
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5361
PubChem Compound53477688
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis Referenceuffman, Max N. 16-Keto estrogens. (1950), US 2522178 19500912 CAN 45:6349 AN 1951:6349
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available