| Common Name |
16-a-Hydroxypregnenolone
| Description |
16-a-Hydroxypregnenolone is a normal urinary metabolite with increased total excretion in newborn infants with congenital adrenal hyperplasia due to 21-hydroxylase deficiency. (PMID 6980322 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(3beta,16alpha)-3,16-Dihydroxypregn-5-en-20-oneChEBI
16-alpha-HydroxypregnenoloneChEBI
(3b,16a)-3,16-Dihydroxypregn-5-en-20-oneGenerator
(3β,16α)-3,16-dihydroxypregn-5-en-20-oneGenerator
16-α-hydroxypregnenoloneGenerator
16 alpha-HydroxypregnenoloneHMDB
16-a-Hydroxy-pregnenoloneHMDB
16-alpha-Hydroxy-pregnenoloneHMDB
16alpha-HydroxypregnenoloneHMDB
3b,16a-Dihydroxypreg-5-en-20-oneHMDB
3b,16a-Dihydroxypregn-5-en-20-oneHMDB
3b,16a-Dihydroxypregnen-5-en-20-oneHMDB
5-Pregnene-3b,16a-diol-20-oneHMDB
Pregn-5-en-3b,16a-diol-20-oneHMDB
3 alpha,16 alpha-Dihydroxypregn-5-en-20-oneMeSH
3 beta,16 alpha-Dihydroxypregn-5-en-20-oneMeSH
3 beta,16 beta-Dihydroxypregn-5-en-20-oneMeSH
| Chemical Formlia |
C21H32O3
| Average Molecliar Weight |
332.477
| Monoisotopic Molecliar Weight |
332.23514489
| IUPAC Name |
1-[(1S,2R,5S,10S,11S,13R,14R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethan-1-one
| Traditional Name |
16α-hydroxypregnenolone
| CAS Registry Number |
520-88-7
| SMILES |
[H][C@@]12C[C@@H](O)[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
| InChI Identifier |
InChI=1S/C21H32O3/c1-12(22)19-18(24)11-17-15-5-4-13-10-14(23)6-8-20(13,2)16(15)7-9-21(17,19)3/h4,14-19,23-24H,5-11H2,1-3H3/t14-,15+,16-,17-,18+,19-,20-,21-/m0/s1
| InChI Key |
ZAKJZPQDUPCXSD-YRWKUUEZSA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Detected and 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.057 mg/mLALOGPS
logP2.79ALOGPS
logP2.35ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)14.75ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity95.27 m3·mol-1ChemAxon
Polarizability38.91 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, Positivesplash10-0159-0049000000-2ccfec5d85aa1a19cec3View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-014j-0194000000-e0041edd20068fee3d7bView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0a6v-1391000000-a896ab547c468e369ce5View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-001i-0019000000-2ab7fa56b70d72f5890dView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-01q9-0029000000-8ccb6ff65b91e81bbea5View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-00ri-1093000000-56249f185b497261aed4View in MoNA
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Umbilical cord
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified16.1 +/- 2.3 uMNewborn (0-30 days old)BothNormal
6455919
details
UrineDetected and Quantified0.05 (0.0 – 0.1) umol/mmol creatinineNewborn (0-30 days old)Not SpecifiedNormal
6980322
details
|
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
UrineDetected but not Quantified Newborn (0-30 days old)Not Available
Congenital adrenal hyperplasia
6980322
details
| 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 |
FDB021942
| KNApSAcK ID |
Not Available
| Chemspider ID |
4955002
| KEGG Compound ID |
C06390
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00315
| Metagene Link |
HMDB00315
| METLIN ID |
5304
| PubChem Compound |
6452574
| PDB ID |
Not Available
| ChEBI ID |
771
Product: Glaucocalyxin B
References |
| Synthesis Reference |
Pierrepoint, C. G.; Griffiths, Keith; Grant, James K. In vitro studies of feminizing tumors of the testis of man and dog. Proc. Int. Congr. Horm. Steroids, 2nd (1967), Meeting Date 1966, 761-6. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Lee SH, Nam SY, Chung BC: Altered profile of endogenous steroids in the urine of patients with prolactinoma. Clin Biochem. 1998 Oct;31(7):529-35. [PubMed:9812172 ]
- Homoki J, Teller WM: Increased urinary excretion of total 16 alpha-hydroxypregnenolone in newborn infants with congenital adrenal hyperplasia due to 21-hydroxylase deficiency. Klin Wochenschr. 1982 Apr 15;60(8):407-10. [PubMed:6980322 ]
|
PMID: 15795231