Structure Database (LMSD)

Common Name
24,26-cyclocholesterol
Systematic Name
(25S)-24S,26-cyclocholest-5-en-3β-ol
Synonyms
LM ID
LMST01110008
Formula
C27H44O
Exact Mass
Calculate m/z
384.339215
Sum Composition
ST 27:2;O
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Calysterols and cyclopropyl sidechain derivatives [ST0111]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Spirastrella cf. vagabunda G300463 (#297665)
Demospongiae (#6042)
Chemical proof of absolute configuration of 24,26-cyclocholesterol by biomimetic conversion to 27-norergostenes,
Tetrahedron Letts, 1983

String Representations

InChiKey (Click to copy)
KQRCOBZIWSKXCB-POEGTNMLSA-N
InChi (Click to copy)
InChI=1S/C27H44O/c1-17(5-6-19-15-18(19)2)23-9-10-24-22-8-7-20-16-21(28)11-13-26(20,3)25(22)12-14-27(23,24)4/h7,17-19,21-25,28H,5-6,8-16H2,1-4H3/t17-,18+,19+,21+,22+,23-,24+,25+,26+,27-/m1/s1
SMILES (Click to copy)
C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CC[C@@]5([H])C[C@]5([H])C)CC[C@@]4([H])[C@]3([H])CC=C2C[C@@H](O)C1

Other Databases

CHEBI ID
173047
PubChem CID
14680449

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 5
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 420.01
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 7.28
Molar Refractivity 117.38

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Created at
-
Updated at
13th Jan 2022