Structure Database (LMSD)

Common Name
(5E)-vitamin D3
Systematic Name
(5E,7E)-(3S)-9,10-seco-5,7,10(19)-cholestatrien-3-ol
Synonyms
  • (5E)-cholecalciferol
  • (5E)-calciol
LM ID
LMST03020220
Formula
C27H44O
Exact Mass
Calculate m/z
384.339215
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
Homo sapiens (#9606)
Mammalia (#40674)
Studies on vitamin D (calciferol) and its analogues. 12. Structural and synthetic studies of 5,6-trans-vitamin D3 and the stereoisomers of 10,19-dihydrovitamin D3 including dihydrotachysterol3.,
J Org Chem, 1977
Pubmed ID: 195026

String Representations

InChiKey (Click to copy)
QYSXJUFSXHHAJI-FVUVGDFOSA-N
InChi (Click to copy)
InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13+/t21-,24+,25-,26+,27-/m1/s1
SMILES (Click to copy)
[C@@H]1(O)C/C(=C\C=C2\[C@]3([H])CC[C@@]([H])([C@@]3(C)CCC\2)[C@]([H])(C)CCCC(C)C)/C(=C)CC1

Other Databases

HMDB ID
HMDB06719
CHEBI ID
145213
LIPIDBANK ID
VVD0239
PubChem CID
5283711
Cayman ID
31225

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 439.45
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 7.91
Molar Refractivity 121.70

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Created at
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Updated at
23rd Jan 2024