MetaCyc Compound: vitamin D2

Synonyms: ergocalciferol

Superclasses: a vitamina vitamin D

Vitamin D refers to a group of fat-soluble secosteroids responsible for enhancing intestinal absorption of calcium, iron, magnesium, phosphate and zinc.

In humans, the most important compounds in this group are vitamin D3 (cholecalciferol), which is produced in animal skin from 7-dehydrocholesterol after exposure to UV light and heat, and vitamin D2 (ergocalciferol), which is produced in plants and fungi from ergosterol after exposure to UV light.

In its activated form, vitamin D3 is necessary for optimal absorption and regulation of dietary Ca2+ and phosphate. This nutrient is essential for the prevention of rickets, a bone-softening disease (reviewed in [DeLuca04, Dusso05, Lips06]).

There is controversy in the literature as to whether supplemental vitamin D2 is as effective as vitamin D3 in maintaining circulating levels of the calcidiol vitamin D metabolite [Houghton06, Holick08]. The production of vitamin D analogs is n active area of research (reviewed in [Prosser04].

Chemical Formula: C28H44O

Molecular Weight: 396.66 Daltons

Monoisotopic Molecular Weight: 396.3392160345 Daltons

vitamin D<SUB>2</SUB> compound structure


InChI: InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26?,27?,28+/m0/s1


Unification Links: CAS:50-14-6, ChemSpider:4474626, HMDB:HMDB00900, PubChem:58855793

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 489.6793Inferred by computational analysis [Latendresse13]

Reactions known to produce the compound:

Not in pathways:
ergosterol + UV light → vitamin D2

Enzymes inhibited by vitamin D2, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: calcitriol 24-hydroxylase [Ohyama91]

This compound has been characterized as an alternative substrate of the following enzymes: vitamin D 25-hydroxylase

Revised 26-Sep-2014 by Caspi R, SRI International


DeLuca04: DeLuca HF (2004). "Overview of general physiologic features and functions of vitamin D." Am J Clin Nutr 80(6 Suppl);1689S-96S. PMID: 15585789

Dusso05: Dusso AS, Brown AJ, Slatopolsky E (2005). "Vitamin D." Am J Physiol Renal Physiol 289(1);F8-28. PMID: 15951480

Holick08: Holick MF, Biancuzzo RM, Chen TC, Klein EK, Young A, Bibuld D, Reitz R, Salameh W, Ameri A, Tannenbaum AD (2008). "Vitamin D2 is as effective as vitamin D3 in maintaining circulating concentrations of 25-hydroxyvitamin D." J Clin Endocrinol Metab 93(3);677-81. PMID: 18089691

Houghton06: Houghton LA, Vieth R (2006). "The case against ergocalciferol (vitamin D2) as a vitamin supplement." Am J Clin Nutr 84(4);694-7. PMID: 17023693

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Lips06: Lips P (2006). "Vitamin D physiology." Prog Biophys Mol Biol 92(1);4-8. PMID: 16563471

Ohyama91: Ohyama Y, Okuda K (1991). "Isolation and characterization of a cytochrome P-450 from rat kidney mitochondria that catalyzes the 24-hydroxylation of 25-hydroxyvitamin D3." J Biol Chem 266(14);8690-5. PMID: 2026586

Prosser04: Prosser DE, Jones G (2004). "Enzymes involved in the activation and inactivation of vitamin D." Trends Biochem Sci 29(12);664-73. PMID: 15544953

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.5 on Fri Nov 27, 2015, BIOCYC13B.