Structure Database (LMSD)

HO O H H H
Common Name
1-oxoprevitamin D3
Systematic Name
(6Z)-(3R)-3-hydroxy-9,10-seco-5(10),6,8-cholestatriene-1-one
Synonyms
  • 1-oxoprecholecalciferol
LM ID
LMST03020158
Formula
C27H42O2
Exact Mass
Calculate m/z
398.31848
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

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

String Representations

InChiKey (Click to copy)
ANAXKKUNYOIUKN-NFYUOBAISA-N
InChi (Click to copy)
InChI=1S/C27H42O2/c1-18(2)8-6-9-19(3)24-13-14-25-21(10-7-15-27(24,25)5)11-12-22-16-23(28)17-26(29)20(22)4/h10-12,18-19,23-25,28H,6-9,13-17H2,1-5H3/b12-11-/t19-,23-,24-,25+,27-/m1/s1
SMILES (Click to copy)
C(/C1C[C@@H](O)CC(=O)C=1C)=C/C1[C@]2([H])CC[C@@]([H])([C@@]2(C)CCC=1)[C@]([H])(C)CCCC(C)C

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthesis of 1β-hydroxyvitamin D3 and 1β,25-dihydroxyvitamin D3,
J Chem Soc Chem Commun, 1977

Other Databases

LIPIDBANK ID
VVD0176
PubChem CID
5283686

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 3
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 445.60
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 7.08
Molar Refractivity 122.09

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Created at
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Updated at
29th Jan 2024