Structure Database (LMSD)

Common Name
3alpha,7alpha,12alpha,26-Tetrahydroxy-5beta-cholest-23E-en-27-oic acid
Systematic Name
3α,7α,12α,26-Tetrahydroxy-5β-23E-cholestan-27-oic acid
Synonyms
LM ID
LMST04030200
Formula
C27H44O6
Exact Mass
Calculate m/z
464.31379
Sum Composition
ST 27:2;O6
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
Rhinella marina (#8386)
Amphibia (#8292)
Bile salts of the toad, Bufo marinus: characterization of a new unsaturated higher bile acid, 3 alpha,7 alpha,12 alpha,26-tetrahydroxy-5 beta-cholest-23-en-27-oic acid.,
J Lipid Res, 1994
Pubmed ID: 7806978

String Representations

InChiKey (Click to copy)
YMJUBWSBLMHBSR-KJNWYSPNSA-N
InChi (Click to copy)
InChI=1S/C27H44O6/c1-15(5-4-6-16(14-28)25(32)33)19-7-8-20-24-21(13-23(31)27(19,20)3)26(2)10-9-18(29)11-17(26)12-22(24)30/h4,6,15-24,28-31H,5,7-14H2,1-3H3,(H,32,33)/b6-4+/t15-,16?,17+,18-,19-,20+,21+,22-,23+,24+,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)C/C=C/C(C(O)=O)CO)CC[C@@]4([H])[C@]3([H])[C@H](O)C[C@]2([H])C[C@H](O)C1

Other Databases

CHEBI ID
186772
PubChem CID
52931536

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 4
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 473.68
Topological Polar Surface Area 118.22
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 6
logP 4.37
Molar Refractivity 127.16

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Created at
-
Updated at
23rd Mar 2021