Structure Database (LMSD)

Common Name
(22E)-25-hydroxy-24-oxo-22,23-didehydrovitamin D3
Systematic Name
(5Z,7E,22E)-(3S)-3,25-dihydroxy-9,10-seco-5,7,10(19),22-cholestatetraen-24-one
Synonyms
  • (22E)-25-hydroxy-24-oxo-22,23-didehydrocholecalciferol
LM ID
LMST03020104
Formula
C27H40O3
Exact Mass
Calculate m/z
412.297745
Status
Active
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
synthetic construct (#32630)
Syntheses of 24,25-dihydroxyvitamin D2, 24,25-dihydroxy-22-dehydrovitamin D3, 25-hydroxy-24-oxo-22-dehydrovitamin D3 and 22,24,25-trihydroxyvitamin D3.,
Chem Pharm Bull (Tokyo), 1987
Pubmed ID: 3496978

String Representations

InChiKey (Click to copy)
CPHSFAAHLTYWNP-QYMFTIPMSA-N
InChi (Click to copy)
InChI=1S/C27H40O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h9-11,15,19,22-24,28,30H,1,6-8,12-14,16-17H2,2-5H3/b15-9+,20-10+,21-11-/t19-,22+,23-,24+,27-/m1/s1
SMILES (Click to copy)
C1C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([H])([C@@]3(C)CCC\2)[C@]([H])(C)/C=C/C(=O)C(O)(C)C)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0119
PubChem CID
5283674

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 3
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 451.75
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 6.26
Molar Refractivity 123.97

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Created at
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Updated at
29th Jan 2024