Structure Database (LMSD)

Systematic Name
(6E)-(8S)-8,25-dihydroxy-9,10-seco-4,6,10(19)-cholestatrien-3-one
Synonyms
LM ID
LMST03020166
Formula
C27H42O3
Exact Mass
Calculate m/z
414.313395
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Secosteroids [ST03]
Vitamin D3 and derivatives [ST0302]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Mus musculus (#10090)
Mammalia (#40674)
Isolation, identification, and chemical synthesis of 8 alpha,25-dihydroxy-9,10-seco-4,6,10(19)-cholestatrien-3-one. A new metabolite of 25-hydroxyvitamin D3 produced by mouse myeloid leukemia cells (M1).,
J Biol Chem, 1987
Pubmed ID: 3477540

String Representations

InChiKey (Click to copy)
CIYNDEHOHLAUJG-BBMMVLKRSA-N
InChi (Click to copy)
InChI=1S/C27H42O3/c1-19-9-10-22(28)18-21(19)13-17-27(30)16-7-15-26(5)23(11-12-24(26)27)20(2)8-6-14-25(3,4)29/h13,17-18,20,23-24,29-30H,1,6-12,14-16H2,2-5H3/b17-13+/t20-,23-,24-,26-,27+/m1/s1
SMILES (Click to copy)
C1C(=C)C(/C=C/[C@]2(O)[C@]3([H])CC[C@@]([H])([C@@]3(C)CCC2)[C@]([H])(C)CCCC(O)(C)C)=CC(=O)C1

Other Databases

CHEBI ID
169000
LIPIDBANK ID
VVD0184
PubChem CID
5283691

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 3
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 454.39
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 6.49
Molar Refractivity 124.06

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Created at
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Updated at
23rd Jan 2024