Structure Database (LMSD)

Common Name
(5E)-3-epivitamin D3
Systematic Name
(5E,7E)-(3R)-9,10-seco-5,7,10(19)-cholestatrien-3-ol
Synonyms
  • (5E)-3-epicholecalciferol
LM ID
LMST03020221
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
synthetic construct (#32630)
Conformational analysis of vitamin D and analogues. 13C and 1H nuclear magnetic resonance study.,
J Org Chem, 1977
Pubmed ID: 198519

String Representations

InChiKey (Click to copy)
QYSXJUFSXHHAJI-RWLOMQAJSA-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

CHEBI ID
191256
LIPIDBANK ID
VVD0240
PubChem CID
5283712

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
19th Jan 2022