Structure Database (LMSD)

Common Name
(22E,24E)-1alpha,25-dihydroxy-26,27-dimethyl-22,23,24,24a-tetradehydro-24a-homovitamin D3
Systematic Name
(5Z,7E,22E,24E)-(1S,3R)-26,27-dimethyl-24a-homo-9,10-seco-5,7,10(19),22,24-cholestapentaene-1,3,25-triol
Synonyms
  • (22E,24E)-1alpha,25-dihydroxy-26,27-dimethyl-22,23,24,24a-tetradehydro-24a-homocholecalciferol
LM ID
LMST03020449
Formula
C30H46O3
Exact Mass
Calculate m/z
454.344695
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)
LVLLALCJVJNGQQ-SEODYNFXSA-N
InChi (Click to copy)
InChI=1S/C30H46O3/c1-6-30(33,7-2)18-9-8-11-21(3)26-15-16-27-23(12-10-17-29(26,27)5)13-14-24-19-25(31)20-28(32)22(24)4/h8-9,11,13-14,18,21,25-28,31-33H,4,6-7,10,12,15-17,19-20H2,1-3,5H3/b11-8+,18-9+,23-13+,24-14-/t21-,25-,26-,27+,28+,29-/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/C(O)(CC)CC)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0539
PubChem CID
5288149
Cayman ID
21579
PDB ID
EB1
GuidePharm ID
2777

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 3
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 503.65
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 7.29
Molar Refractivity 139.24

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Created at
-
Updated at
22nd Jan 2024