| Common Name |
27-Norcholestanehexol
| Description |
27-Norcholestanehexol is a bile alcohol. Bile alcohols have been found to be present as minor components in the bile and urine in healthy subjects. Bile alcohols are end products for cholesterol elimination as well as major biliary constituents; in mammals, cholesterol is metabolized by additional enzymes that litimately transform it to bile acids. Bile alcohols are preferentially excreted as glucuronides into the urine, which constitute about 10% of total bile acids. The excretion of glucuronidated bile alcohols in urine is suggested to reflect an alternative metabolism of intermediates in the normal biosynthesis of bile acids. (PMID: 6548247 , 11718684 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
27-Norcholestane-3,7,12,24,25,26-hexolHMDB
27-N-5-CHMeSH
27-Nor-5beta-cholestane- 3alpha,7alpha,12alpha,24alpha,24xi,25xi,26-hexolMeSH
| Chemical Formlia |
C26H46O6
| Average Molecliar Weight |
454.6398
| Monoisotopic Molecliar Weight |
454.329439204
| IUPAC Name |
(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-2,15-dimethyl-14-[(2R)-5,6,7-trihydroxyheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
| Traditional Name |
27-norcholestanehexol
| CAS Registry Number |
91999-66-5
| SMILES |
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)C(O)CO
| InChI Identifier |
InChI=1S/C26H46O6/c1-14(4-7-20(29)22(31)13-27)17-5-6-18-24-19(12-23(32)26(17,18)3)25(2)9-8-16(28)10-15(25)11-21(24)30/h14-24,27-32H,4-13H2,1-3H3/t14-,15+,16-,17-,18+,19+,20?,21-,22?,23+,24+,25+,26-/m1/s1
| InChI Key |
PYLPANOYZCSFOX-UCIVWCSPSA-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 Solubility0.25 mg/mLALOGPS
logP1.89ALOGPS
logP1.11ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)13.34ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area121.38 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity122.98 m3·mol-1ChemAxon
Polarizability52.9 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 |
FDB022873
| KNApSAcK ID |
Not Available
| Chemspider ID |
170096
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB02157
| Metagene Link |
HMDB02157
| METLIN ID |
Not Available
| PubChem Compound |
196302
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Chloroxylenol
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Nakagawa M, Une M, Takenaka S, Tazawa Y, Nozaki S, Imanaka T, Kuramoto T: Urinary bile alcohol profiles in healthy and cholestatic children. Clin Chim Acta. 2001 Dec;314(1-2):101-6. [PubMed:11718684 ]
- Karlaganis G, Karlaganis V, Sjovall J: Identification of 27-nor-5 beta-cholestane-3 alpha,7 alpha,12 alpha,24 xi, 25 xi,26-hexol and partial characterization of the bile alcohol profile in urine. J Lipid Res. 1984 Jul;25(7):693-702. [PubMed:6548247 ]
|
PMID: 11741201