| Common Name |
3b,17a,21-Trihydroxypregnenone
| Description |
3b,17a,21-Trihydroxypregnenone is an intermediate in the human fetus at midpregnancy converting it to cortisol (PMID 4231965 ). It has been found as an intermediate in alternative pathways in human adrenal steroidogenesis that take place under in vitro conditions of normal adrenal slices from patients with hypernephroid kidney carcinomas that bypass cholesterol, pregnenolone, progesterone and proceed to 21-hydroxypregnenolone (PMID 6247575 ).
| Structure |
| Synonyms |
| Value |
Source |
17,21-DihydroxypregnenoloneHMDB
17a,21-DihydroxypregnenoloneHMDB
3b,17a,21-Trihydroxypregn-5-en-20-oneHMDB
| Chemical Formlia |
C21H32O4
| Average Molecliar Weight |
348.4764
| Monoisotopic Molecliar Weight |
348.230059512
| IUPAC Name |
(1S,2S,10S,11S,14S,15S)-5,14-dihydroxy-14-(2-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one
| Traditional Name |
(1S,2S,10S,11S,14S,15S)-5,14-dihydroxy-14-(2-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one
| CAS Registry Number |
1167-48-2
| SMILES |
[H][C@@]12CC[C@](O)(CCO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C
| InChI Identifier |
InChI=1S/C21H32O4/c1-19-7-5-17-15(16(19)6-8-21(19,25)9-10-22)4-3-13-11-14(23)12-18(24)20(13,17)2/h12-13,15-17,22-23,25H,3-11H2,1-2H3/t13?,15-,16-,17-,19-,20-,21-/m0/s1
| InChI Key |
RJKJQHWLCLYSHD-DGFNXGTDSA-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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.055 mg/mLALOGPS
logP2.33ALOGPS
logP2.39ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8.84ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity97.84 m3·mol-1ChemAxon
Polarizability40.01 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| 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 |
FDB022000
| KNApSAcK ID |
Not Available
| Chemspider ID |
17215943
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00382
| Metagene Link |
HMDB00382
| METLIN ID |
5371
| PubChem Compound |
Not Available
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: APS-2-79 (hydrochloride)
References |
| Synthesis Reference |
Heer, J.; Miescher, K. Steroids. CIV. The synthesis of the dihydroxyacetone side chain in the steroid series. Helvetica Chimica Acta (1951), 34 359-72. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Pasqualini JR, Lowy J, Wiqvist N, Diczfalusy E: Biosynthesis of cortisol from 3 beta, 17 alpha,21-trihydroxypregn-5-en-20-one by the intact human foetus at midpregnancy. Biochim Biophys Acta. 1968 May 1;152(3):648-50. [PubMed:4231965 ]
- Kaufmann SH, Sinterhauf K, Lommer D: Alternative pathways in human corticosteroid biosynthesis. J Steroid Biochem. 1980 Jun;13(6):599-605. [PubMed:6247575 ]
|
PMID: 26134655