Structure Database (LMSD)

Common Name
(22E,24E)-1alpha,26a-dihydroxy-22,23,24,25-tetradehydro-26a-homo-27-norvitamin D3
Systematic Name
(5Z,7E,22E,24E)-(1S,3R)-26a-homo-27-nor-9,10-seco-5,7,10(19),22,24-cholestapentaene-1,3,26a-triol
Synonyms
  • (22E,24E)-1alpha,26a-dihydroxy-22,23,24,25-tetradehydro-26a-homo-27-norcholecalciferol
LM ID
LMST03020114
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)
Synthesis and Biological Activity of 1a-hydroxylated Vitamin D Analogues with Poly-unsaturated Side Chains,
Vitamin D, 1994

String Representations

InChiKey (Click to copy)
XLVDCYSDODCPIR-QJQWSQMNSA-N
InChi (Click to copy)
InChI=1S/C27H40O3/c1-19(9-6-4-5-7-16-28)24-13-14-25-21(10-8-15-27(24,25)3)11-12-22-17-23(29)18-26(30)20(22)2/h4-6,9,11-12,19,23-26,28-30H,2,7-8,10,13-18H2,1,3H3/b5-4+,9-6+,21-11+,22-12-/t19-,23-,24-,25+,26+,27-/m1/s1
SMILES (Click to copy)
[C@@H]1(O)C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([C@@](C)([H])/C=C/C=C/CCO)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0129
PubChem CID
9547360

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 451.75
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 6.12
Molar Refractivity 125.39

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Created at
-
Updated at
8th Dec 2023