Structure Database (LMSD)

Common Name
(17Z)-1alpha,25-dihydroxy-26,27-dimethyl-17,20,22,22,23,23-hexadehydrovitamin D3
Systematic Name
(5Z,7E,17Z)-(1S,3R)-26,27-dimethyl-9,10-seco-5,7,10(19),17(20)-cholestatetraen-22-yne-1,3,25-triol
Synonyms
  • (17Z)-1alpha,25-dihydroxy-26,27-dimethyl-17,20,22,22,23,23-hexadehydrocholecalciferol
LM ID
LMST03020391
Formula
C29H42O3
Exact Mass
Calculate m/z
438.313395
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)
Chemistry and Biology of 22,23-yne Analogs of Calcitriol,
Vitamin D, 1994

String Representations

InChiKey (Click to copy)
UENVSUKLKMJWQW-IGELHMHJSA-N
InChi (Click to copy)
InChI=1S/C29H42O3/c1-6-29(32,7-2)17-8-10-20(3)25-14-15-26-22(11-9-16-28(25,26)5)12-13-23-18-24(30)19-27(31)21(23)4/h12-13,24,26-27,30-32H,4,6-7,9,11,14-19H2,1-3,5H3/b22-12+,23-13-,25-20-/t24-,26+,27+,28-/m1/s1
SMILES (Click to copy)
[C@@H]1(O)C(=C)/C(=C\C=C2\[C@]3([H])CC/C(=C(/C#CCC(O)(CC)CC)\C)/[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

CHEBI ID
168224
LIPIDBANK ID
VVD0475
PubChem CID
9547500

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 3
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 483.71
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 6.63
Molar Refractivity 133.40

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Created at
-
Updated at
31st May 2022