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34310-86-6 molecular structure
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(1S,2R,5S,6S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadec-7-ene-5,6-diol

ChemBase ID: 170338
Molecular Formular: C27H46O2
Molecular Mass: 402.65294
Monoisotopic Mass: 402.34978071
SMILES and InChIs

SMILES:
C1[C@@H]([C@H](C2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@H]1[C@@H](CCCC(C)C)C)C)O)O
Canonical SMILES:
CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H]([C@H]2O)O)C)C
InChI:
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(29)24(28)14-16-27(23,5)22(19)13-15-26(20,21)4/h10,17-22,24-25,28-29H,6-9,11-16H2,1-5H3/t18-,19+,20-,21+,22+,24+,25+,26-,27-/m1/s1
InChIKey:
CZDKQKOAHAICSF-GFYXKKFXSA-N

Cite this record

CBID:170338 http://www.chembase.cn/molecule-170338.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,2R,5S,6S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadec-7-ene-5,6-diol
IUPAC Traditional name
(1S,2R,5S,6S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadec-7-ene-5,6-diol
Synonyms
(3β,4α)-Cholest-5-ene-3,4-diol
Cholest-5-ene-3β,4α-diol
4α-Hydroxy Cholesterol
CAS Number
34310-86-6
PubChem SID
164226248
PubChem CID
12955779

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC H917975 external link Add to cart
PubChem 12955779 external link
Data Source Data ID Price
TRC
H917975 external link Add to cart Please log in.
Data Source Data ID
PubChem 12955779 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.5001745  H Acceptors
H Donor LogD (pH = 5.5) 6.193893 
LogD (pH = 7.4) 6.1938925  Log P 6.193893 
Molar Refractivity 121.824 cm3 Polarizability 48.564686 Å3
Polar Surface Area 40.46 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Ethyl Acetate expand Show data source
Apperance
Off-White to Brownish Orange Solid expand Show data source
Melting Point
>177°C (dec.) expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
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DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - H917975 external link
A metabolite of Cholesterol. It is formed from Cholesterol by the drug-metabolizing enzyme cytochrome P 450 3A4. A potential ligand for the nuclear receptor LXR and also a new endogenous CYP3A marker.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Breuer, O., et al.: J. Lipid Res., 36, 2275 (1995)
  • • Pikuleva, I., et al.: J. Biol. Chem., 273, 18153 (1995)
  • • Chawla, A., et al.: Science, 294, 1866 (1995)
  • • Bodin, K., et al.: J. Biol. Chem., 276, 38685 (1995)
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PATENTS

PATENTS

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INTERNET

INTERNET

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