Structure Database (LMSD)

Common Name
5-alpha-Bufol
Systematic Name
5α-Cholestane-3α,7α,12α,25,26-pentol
Synonyms
LM ID
LMST04030015
Formula
C27H48O5
Exact Mass
Calculate m/z
452.350175
Sum Composition
ST 27:0;O5
Status
Curated
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
Notophthalmus meridionalis kallerti (#2583465)
Amphibia (#8292)
Stero-bile Acids and Bile Alcohols*: XCVI Studies on the Bile Salta of the Newt and synthesis of 5α-Cholestane-3α,7α,1α ,25, 26 pentol (5α-Bufol),
J Biochem, 1967

String Representations

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

Other Databases

CHEBI ID
182127
LIPIDBANK ID
BBA0321
PubChem CID
5284193

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 4
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 470.17
Topological Polar Surface Area 101.15
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 5
logP 4.93
Molar Refractivity 127.27

Admin

Created at
-
Updated at
20th Mar 2024