| Common Name |
5b-Cholestane-3a,7a,12a,24,25-pentol
| Description |
5b-Cholestane-3a,7a,12a,24,25-pentol has been found excreted in the urine from a patient with sitosterolemia as glycine- and taurine-conjugated bile acids (PMID 7896564 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
3a,7a,12a,24,25-PentahydroxycoprostaneHMDB
3alpha,7alpha,12alpha,24R,25-Pentahydroxy-5beta-cholestaneHMDB
5beta-Cholestane-3alpha,7alpha,12alpha,24R,25-pentolHMDB
| Chemical Formlia |
C27H48O5
| Average Molecliar Weight |
452.667
| Monoisotopic Molecliar Weight |
452.350174646
| IUPAC Name |
(1S,2S,5R,9R,10R,11S,14R,15R,16S)-14-[(2R)-5,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
| Traditional Name |
(1S,2S,5R,9R,10R,11S,14R,15R,16S)-14-[(2R)-5,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
| CAS Registry Number |
58469-95-7
| SMILES |
[H][C@@]12CC[C@H]([C@H](C)CCC(O)C(C)(C)O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2C[C@H](O)CC[C@]12C
| InChI Identifier |
InChI=1S/C27H48O5/c1-15(6-9-22(30)25(2,3)32)18-7-8-19-24-20(14-23(31)27(18,19)5)26(4)11-10-17(28)12-16(26)13-21(24)29/h15-24,28-32H,6-14H2,1-5H3/t15-,16?,17-,18-,19+,20+,21-,22?,23+,24+,26+,27-/m1/s1
| InChI Key |
NHPWQASMMFUHIZ-OOOZRTEJSA-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
| 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 Solubility0.044 mg/mLALOGPS
logP2.54ALOGPS
logP2.43ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)13.85ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area101.15 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity126.07 m3·mol-1ChemAxon
Polarizability54 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
| 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 |
FDB022116
| KNApSAcK ID |
Not Available
| Chemspider ID |
13628107
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00556
| Metagene Link |
HMDB00556
| METLIN ID |
5540
| PubChem Compound |
21252253
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Naquotinib
References |
| Synthesis Reference |
Hoshita, Takahiko. Bile acids and sterols. XLVII. Synthesis of 3a,7a,12a,25x,26-and 3a,7a,12a,24x,25-pentahydroxycoprostanes. Journal of Biochemistry (Tokyo, Japan) (1962), 52 176-9. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Ohshima A, Une M, Hoshita T: Biochemical studies of inherited diseases related to abnormal cholesterol metabolism. II: Absence of unusual C28 and C29 bile acid homologs in bile and urine of sitosterolemia. Hiroshima J Med Sci. 1994 Sep;43(3):81-6. [PubMed:7896564 ]
|
PMID: 7514038