Structure Database (LMSD)

Common Name
(17S,20R)-1alpha,25-dihydroxy-17,20-methano-21-norvitamin D3
Systematic Name
(5Z,7E)-(1S,3R,17S,20R)-17,20-methano-21-nor-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol
Synonyms
  • (17S,20R)-1alpha,25-dihydroxy-17,20-methano-21-norcholecalciferol
LM ID
LMST03020177
Formula
C27H42O3
Exact Mass
Calculate m/z
414.313395
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)
Design and synthesis of 1 α,25-dihydroxyvitamin D3 analogues with fixed torsion angle C(16-17-20-22),
Tetrahedron Letts, 1998

String Representations

InChiKey (Click to copy)
XCUVBGNTCMZQAU-FFDNLMTISA-N
InChi (Click to copy)
InChI=1S/C27H42O3/c1-18-20(15-22(28)16-24(18)29)10-9-19-7-5-13-26(4)23(19)11-14-27(26)17-21(27)8-6-12-25(2,3)30/h9-10,21-24,28-30H,1,5-8,11-17H2,2-4H3/b19-9+,20-10-/t21-,22-,23+,24+,26+,27+/m1/s1
SMILES (Click to copy)
[C@@H]1(O)C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]4(C[C@]4(CCCC(O)(C)C)[H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0195
PubChem CID
9547397

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 4
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 444.67
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 6.32
Molar Refractivity 123.46

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Created at
-
Updated at
29th Jan 2024