LIPID MAPS

Structure Database (LMSD)

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Common Name

25-Hydroxy-3-epivitamin D3

Systematic Name

(5Z,7E)-(3R)-9,10-seco-5,7,10(19)-cholestatriene-3,25-diol

Synonyms

LM ID

LMST03020646

Formula

C₂₇H₄₄O₂

Exact Mass

Calculate m/z

400.334131

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

3-epi-25-hydroxy Vitamin D3 is the C-3 epimer of 25-hydroxy vitamin D3 .¹ Dietary administration of 3-epi-25-hydroxy vitamin D3 (0.5 and 1 IU/g) decreases levels of serum parathyroid hormone (PTH) in male, but not female, weanling rats.

This information has been provided by Cayman Chemical

References

1. Djekic-Ivankovic, M., Lavery, P., Agellon, S., et al. The C-3α epimer of 25-hydroxycholecalciferol from endogenous and exogenous sources supports normal growth and bone mineral density in weanling rats. J. Nutr. 147(2), 141-151 (2017).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

C-3 epimers can account for a significant proportion of total circulating 25-hydroxyvitamin D in infants, complicating accurate measurement and interpretation of vitamin D status.,
J Clin Endocrinol Metab, 2006

Pubmed ID: 16720650

String Representations

InChiKey (Click to copy)

JWUBBDSIWDLEOM-UEGFJKGBSA-N

InChi (Click to copy)

InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23-,24-,25+,27-/m1/s1

SMILES (Click to copy)

C1/C(=C/C=C2\CCC[C@]3(C)[C@]([C@]([H])(C)CCCC(O)(C)C)([H])CC[C@@]\23[H])/C(=C)CC[C@H]1O