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Structure Database (LMSD)

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Common Name

previtamin D3

Systematic Name

(6Z)-(3S)-9,10-seco-5(10),6,8-cholestatrien-3-ol

Synonyms

precholecalciferol
(6Z)-tacalciol

LM ID

LMST03020222

Formula

C₂₇H₄₄O

Exact Mass

Calculate m/z

384.339215

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Previtamin D3 is an intermediate in the synthesis of the calcitriol precursor vitamin D3 .^1,2 It is formed from 7-dehydro cholesterol in the epidermis via photolytic conversion by UVB radiation and is isomerized to vitamin D3. The rate of previtamin D3 synthesis is dependent on the solar zenith angle, which is affected by the latitude, season, and time of day. It is also dependent on the level of skin pigmentation and age, among other factors, with a negative correlation to higher pigmentation and age.^3,2,4

This information has been provided by Cayman Chemical

References

1. Rosen, C.J. Vitamin D insufficiency. N. Engl. J. Med. 364(3), 248-254 (2011).

2. Chen, T.C., Chimeh, F., Lu, Z., et al. Factors that influence the cutaneous synthesis and dietary sources of vitamin D. Arch. Biochem. Biophys. 460(2), 213-217 (2007).

3. Holick, M.F., Chen, T.C., Lu, Z., et al. Vitamin D and skin physiology: A D-lightful story. J. Bone Miner. Res. 22 Suppl 2., V28-33 (2007).

4. Webb, A.R. Who, what, where and when-influences on cutaneous vitamin D synthesis. Prog. Biophys. Mol. Biol. 92(1), 17-25 (2006).

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References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Rattus norvegicus (#10116)

Mammalia (#40674)

Photometabolism of 7-dehydrocholesterol to previtamin D3 in skin.,
Biochem Biophys Res Commun, 1977

Pubmed ID: 194588

String Representations

InChiKey (Click to copy)

YUGCAAVRZWBXEQ-WHTXLNIXSA-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/h10,12-13,19,21,24-26,28H,6-9,11,14-18H2,1-5H3/b13-12-/t21-,24+,25-,26+,27-/m1/s1

SMILES (Click to copy)

C(/C1C[C@@H](O)CCC=1C)=C/C1[C@]2([H])CC[C@@]([H])([C@@]2(C)CCC=1)[C@]([H])(C)CCCC(C)C