Structure Database (LMSD)

Common Name
(22E,24E)-1alpha,25-dihydroxy-22,23,24,24a-tetradehydro-24a,24b-dihomovitamin D3
Systematic Name
(5Z,7E,22E,24E)-(1S,3R)-24a,24b-dihomo-9,10-seco-5,7,10(19),22,24-cholestapentaene-1,3,25-triol
Synonyms
  • (22E,24E)-1alpha,25-dihydroxy-22,23,24,24a-tetradehydro-24a,24b-dihomocholecalciferol
LM ID
LMST03020395
Formula
C29H44O3
Exact Mass
Calculate m/z
440.329045
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 D3 Analogues with Hydroxylated Side Chains, Multi-Homologated in The 24- or 24,26,27-Positions,
Vitamin D, 1991

String Representations

InChiKey (Click to copy)
SYLQVDSHYYZGRV-IRLMEWJWSA-N
InChi (Click to copy)
InChI=1S/C29H44O3/c1-20(10-7-6-8-16-28(3,4)32)25-14-15-26-22(11-9-17-29(25,26)5)12-13-23-18-24(30)19-27(31)21(23)2/h6-8,10,12-13,20,24-27,30-32H,2,9,11,14-19H2,1,3-5H3/b8-6+,10-7+,22-12+,23-13-/t20-,24-,25-,26+,27+,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/CC(O)(C)C)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0479
PubChem CID
9547504

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 486.35
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 6.90
Molar Refractivity 134.62

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Created at
-
Updated at
31st May 2022