| Common Name |
5a-Cholestane-3a,7a,12a,23,25-pentol
| Description |
5a-Cholestane-3a,7a,12a,23,25-pentol is a bile acid found in the urine of patients with cerebrotendinous xanthomatosis. (PMID 1805458 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(3a,5a,7a,12a,23S)-Cholestane-3,7,12,23,25-pentolHMDB
| Chemical Formlia |
C27H48O5
| Average Molecliar Weight |
452.667
| Monoisotopic Molecliar Weight |
452.350174646
| IUPAC Name |
(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-14-[(2S)-4,6-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,7R,9R,10R,11S,14R,15R,16S)-14-[(2S)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
| CAS Registry Number |
137252-15-4
| SMILES |
[H][C@@]12CC[C@H]([C@@H](C)CC(O)CC(C)(C)O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@@]2([H])C[C@H](O)CC[C@]12C
| InChI Identifier |
InChI=1S/C27H48O5/c1-15(10-18(29)14-25(2,3)32)19-6-7-20-24-21(13-23(31)27(19,20)5)26(4)9-8-17(28)11-16(26)12-22(24)30/h15-24,28-32H,6-14H2,1-5H3/t15-,16+,17+,18?,19+,20-,21-,22+,23-,24-,26-,27+/m0/s1
| InChI Key |
OXSBBBPDYVCAKC-KHMINMIBSA-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 Solubility0.052 mg/mLALOGPS
logP2.33ALOGPS
logP2.05ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)14.93ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area101.15 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity126.34 m3·mol-1ChemAxon
Polarizability53.69 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 |
FDB022118
| KNApSAcK ID |
Not Available
| Chemspider ID |
13628108
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00558
| Metagene Link |
HMDB00558
| METLIN ID |
5542
| PubChem Compound |
21252254
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Pirmenol (hydrochloride)
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Kihira K, Fukuda K, Kuramoto T, Kuriyama M, Fujiyama J, Osame M, Hoshita T: Identification of (23S)-5 alpha-cholestane-3 alpha,7 alpha,12 alpha,23,25-pentol in urine of patients with cerebrotendinous xanthomatosis. Steroids. 1991 Sep;56(9):464-8. [PubMed:1805458 ]
|
PMID: 23174562