Structure Database (LMSD)

Common Name
1alpha,17alpha,21-trihydroxy-20-oxo-22,23,24,25,26,27-hexanorvitamin D3
Systematic Name
(5Z,7E)-(1S,3R,17R)-1,3,17,21-tetrahydroxy-9,10-seco-5,7,10(19)-pregnatrien-20-one
Synonyms
  • 1alpha,17alpha,21-trihydroxy-20-oxo-22,23,24,25,26,27-hexanorcholecalciferol
LM ID
LMST03020005
Formula
C21H30O5
Exact Mass
Calculate m/z
362.209325
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)
Synthesis and immunoregulating activity of vitamin D analogues bearing pregnane side chains,
Bioord Med Chem letts, 1992

String Representations

InChiKey (Click to copy)
ZECRGLYRELFXSW-LAMPCNEESA-N
InChi (Click to copy)
InChI=1S/C21H30O5/c1-13-15(10-16(23)11-18(13)24)6-5-14-4-3-8-20(2)17(14)7-9-21(20,26)19(25)12-22/h5-6,16-18,22-24,26H,1,3-4,7-12H2,2H3/b14-5+,15-6-/t16-,17+,18+,20+,21+/m1/s1
SMILES (Click to copy)
[C@@H]1(O)C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@](C(CO)=O)(O)[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0006
PubChem CID
9547265

Calculated Physicochemical Properties

Heavy Atoms 26
Rings 3
Aromatic Rings 0
Rotatable Bonds 3
Van der Waals Molecular Volume 368.17
Topological Polar Surface Area 97.99
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 2.95
Molar Refractivity 100.30

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Created at
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Updated at
8th Dec 2023