Structure Database (LMSD)

Common Name
1alpha,25-dihydroxy-2beta-(6-hydroxyhexyl)vitamin D3
Systematic Name
(5Z,7E)-(1S,2R,3R)-2-(6-hydroxyhexyl)-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol
Synonyms
  • 1alpha,25-dihydroxy-2beta-(6-hydroxyhexyl)cholecalciferol
LM ID
LMST03020534
Formula
C33H56O4
Exact Mass
Calculate m/z
516.41786
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)
Synthetic studies of vitamin D analogs. XXIV. Synthesis of active vitamin D3 analogs substituted at the 2 beta-position and their preventive effects on bone mineral loss in ovariectomized rats.,
Chem Pharm Bull (Tokyo), 1997
Pubmed ID: 9353890

String Representations

InChiKey (Click to copy)
MAINXJQGDLCPQQ-ALINLBMXSA-N
InChi (Click to copy)
InChI=1S/C33H56O4/c1-23(12-10-19-32(3,4)37)28-17-18-29-25(13-11-20-33(28,29)5)15-16-26-22-30(35)27(31(36)24(26)2)14-8-6-7-9-21-34/h15-16,23,27-31,34-37H,2,6-14,17-22H2,1,3-5H3/b25-15+,26-16-/t23-,27-,28-,29+,30-,31-,33-/m1/s1
SMILES (Click to copy)
[C@@H]1(O)C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([C@@](C)([H])CCCC(O)(C)C)([H])[C@@]3(C)CCC\2)/C[C@@H](O)[C@H]1CCCCCCO

Other Databases

CHEBI ID
169808
LIPIDBANK ID
VVD0625
PubChem CID
9547638

Calculated Physicochemical Properties

Heavy Atoms 37
Rings 3
Aromatic Rings 0
Rotatable Bonds 12
Van der Waals Molecular Volume 569.62
Topological Polar Surface Area 80.92
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 4
logP 8.02
Molar Refractivity 155.11

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Created at
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Updated at
17th Feb 2022