Structure Database (LMSD)

Common Name
5beta-Cyprinol
Systematic Name
5β-Cholestane-3α,7α,12α,26,27-pentol
Synonyms
LM ID
LMST04030041
Formula
C27H48O5
Exact Mass
Calculate m/z
452.350175
Sum Composition
ST 27:0;O5
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Bile acids and derivatives [ST04]
C27 bile acids, alcohols, and derivatives [ST0403]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Conger myriaster (#7943)
Actinopteri (#186623)
The isolation of a new bile alcohol, 5b-cholestane-3a,7a,12a,26,27-pentol from the bile of Conger myriaster,
Steroids, 1964
Homo sapiens (#9606)
Mammalia (#40674)
Significance of bile alcohol in urine of a patient with cholestasis: identification of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,26,27-pentol ( beta-cyprinol) and 5 beta-cholestane-3 alpha,7 alpha,12 alpha,26-tetrol (27-deoxy-5 beta-cyprinol).,
Chem Pharm Bull (Tokyo), 1984
Pubmed ID: 6499098

String Representations

InChiKey (Click to copy)
JNMALBXXJSWZQY-JKUZLEDPSA-N
InChi (Click to copy)
InChI=1S/C27H48O5/c1-16(5-4-6-17(14-28)15-29)20-7-8-21-25-22(13-24(32)27(20,21)3)26(2)10-9-19(30)11-18(26)12-23(25)31/h16-25,28-32H,4-15H2,1-3H3/t16-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
SMILES (Click to copy)
C1[C@]2(C)[C@@]3([H])C[C@H](O)[C@]4(C)[C@@]([H])([C@]([H])(C)CCCC(CO)CO)CC[C@@]4([H])[C@]3([H])[C@H](O)C[C@]2([H])C[C@H](O)C1

Other Databases

CHEBI ID
37913
LIPIDBANK ID
BBA0356
PubChem CID
5284215

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 4
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 470.17
Topological Polar Surface Area 101.15
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 5
logP 4.78
Molar Refractivity 127.20

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Created at
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Updated at
20th Mar 2024