LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

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

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

5,6-trans-Vitamin D3 is an isomer of vitamin D3 .¹ In vivo, 5,6-trans-vitamin D3 (1, 3, and 10 µg/day) increases tibia ash weight and bone mineralization in vitamin D-deficient chicks. 5,6-trans-Vitamin D3 (25 µg/animal) induces intestinal calcium transport and bone calcium mobilization in anephric rats fed a low-calcium and vitamin D-deficient diet.²

This information has been provided by Cayman Chemical

References

1. Boris, A., Hurley, J.F., and Trmal, T. Relative activities of some metabolites and analogs of cholecalciferol in stimulation of tibia ash weight in chicks otherwise deprived of vitamin D. J. Nutr. 107(2), 194-198 (1977).

2. Holick, M.F., Garabedian, M., and DeLuca, H.F. 5,6-Trans isomers of cholecalciferol and 25-hydroxycholecalciferol. Substitutes for 1,25-dihydroxycholecalciferol in anephric animals. Biochemistry 11(14), 2715-2719 (1972).

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