| Common Name |
16-Oxoandrostenediol
| Description |
16-Oxoandrostenediol is a naturally occurring androgenic steroid hormone generated by the adrenal glands. It has been found in the urine of newborn infants. Secretion of this steroid is suppressed by dexamethasone. Levels of this hormone are almost absent by 5 months of age. ((Steroids (1964), 3(1), 77-83.) ). 16-Oxoandrostenediol is a natural hormone with androgenic activity and that two potent antiandrogens: hydroxyflutamide (Eliexin) and bicalutamide (Casodex).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(3b,17b)-3b,17b-Dihydroxyandrost-5-en-16-oneHMDB
3b,17b-Dihydroxy-androst-5-en-16-oneHMDB
3b,17b-Dihydroxyandrost-5-en-16-oneHMDB
3beta,17beta-Dihydroxy-androst-5-en-16-oneHMDB
5-Androsten-3b,17b-diol-16-oneHMDB
Androst-5-ene-3b,17b-diol-16-oneHMDB
| Chemical Formlia |
C19H28O3
| Average Molecliar Weight |
304.4238
| Monoisotopic Molecliar Weight |
304.203844762
| IUPAC Name |
(2R,5S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-one
| Traditional Name |
5-androsten-3b,17b-diol-16-one
| CAS Registry Number |
1159-66-6
| SMILES |
C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CC(=O)[C@@H]2O
| InChI Identifier |
InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-15,17,20,22H,4-10H2,1-2H3/t12-,13?,14?,15?,17-,18-,19-/m0/s1
| InChI Key |
AKRBLZKRYPEVIK-IACDPKRHSA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Expected 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 Emlisifiers
| Cellliar locations |
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point203 – 205 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.12 mg/mLALOGPS
logP2.39ALOGPS
logP2.13ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)12.97ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.95 m3·mol-1ChemAxon
Polarizability34.66 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-052r-0094000000-bc00afb765c32f27cdb5View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-0a4r-0191000000-05d2e664ac4d9ef4363cView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0pvi-3590000000-c0b23f4d56161a228791View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-0udi-0029000000-1cc7a9092823445c7d7eView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-0udi-0079000000-0648fbf68146b515254aView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-0076-2090000000-98800c5259e32862774eView in MoNA
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane
| Biofluid Locations |
Not Available
| Tissue Location |
Adrenal Gland
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB021948
| KNApSAcK ID |
Not Available
| Chemspider ID |
Not Available
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00322
| Metagene Link |
HMDB00322
| METLIN ID |
5311
| PubChem Compound |
53477682
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: MK-8998
References |
| Synthesis Reference |
Aoki, Terumi; Yamamura, Hiroko; Takei, Kyoko; Mori, Hiromu. Synthesis of 16-oxygenated androst-5-en-3b-ol derivatives. Chemical & Pharmaceutical Bulletin (1964), 12(7), 808-12. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
Not Available |
PMID: 26976569