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Bovine Metabolome Database



Showing metabocard for 5b-Cholestane-3a,7a,12a,23R,25-pentol (BMDB00513)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:58:02
Accession Number BMDB00513
Common Name 5b-Cholestane-3a,7a,12a,23R,25-pentol
Description 5b-Cholestane-3a,7a,12a,23R,25-pentol is a bile alcohol present in the urine of patients with cerebrotendinous xanthomatosis, but not in feces. A possible explanation for the urinary cholestanepentols is that the major serum bile alcohol, 5b-cholestane-3a,7a,12a,25-tetrol, might be hydroxylated at C-23 to form (23)-5b-cholestane-3a,7a,12a,23,25-pentols in the kidneys, an hypothesis supported by the fact that in our patient (23R)-5b-cholestane-3a,7a,12a,23,25-pentol was detected only in urine but were virtually absent in bile. (PMID 3700361)
Synonyms
  1. 17-(3,5-dihydroxy-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,7,12-triol
  2. 5b-Cholestane-3a,7a,12a,23R,25-pentol
Chemical IUPAC Name Not Available
Chemical Formula C27H48O5
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Dihydroxy steroids
Family
  • Mammalian_Metabolite
Species
  • secondary alcohol; tertiary alcohol
Biofunction
  • Hormones, Membrane component
Application
Source
  • Endogenous
Average Molecular Weight 452.667
Monoisotopic Molecular Weight 452.350189
Isomeric SMILES C[C@H](C[C@@H](O)CC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C
Canonical SMILES CC(CC(O)CC(C)(C)O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID 5499 Link Image
PubChem Compound Not Available
PubChem Substance Not Available
ChEBI ID Not Available
CAS Registry Number 59906-14-8
InChI Identifier InChI=1/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-/m1/s1
Synthesis Reference Hoshita, Takahiko; Yasuhara, Misao; Kihira, Kenji; Kuramoto, Taiju. Comparative biochemical studies of bile acids and bile alcohols. V. Identification of (23S)-5a-cholestane-3a,7a,12a,23,25-pentol in cerebrotendinous xanthomatosis. Steroids (1976), 27(5), 657-64.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.052199997 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 2.33 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References Not Available