Structure Database (LMSD)

Common Name
1alpha-hydroxy-26,27-dinorvitamin D3 25-carboxylic acid
Systematic Name
(5Z,7E)-(1S,3R)-1,3-dihydroxy-25-homo-9,10-seco-5,7,10(19)-cholatrien-25-oic acid
Synonyms
  • 1alpha-hydroxy-26,27-dinorcholecalciferol 25-carboxylic acid
LM ID
LMST03020025
Formula
C25H38O4
Exact Mass
Calculate m/z
402.27701
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)
Unsaturated steroids. Part 12. Synthesis of 1α,3β-dihydroxy-24-nor-9,10-secochola-5,7,10(19)trien-23-oic (calcitroic) acid and of the cholic-and 25-homocholic acid analogues,
J. Chem. Soc., Perkin Trans. 1, 1985

String Representations

InChiKey (Click to copy)
FMONOGKOJOGACR-LIWPMISOSA-N
InChi (Click to copy)
InChI=1S/C25H38O4/c1-16(6-4-8-24(28)29)21-11-12-22-18(7-5-13-25(21,22)3)9-10-19-14-20(26)15-23(27)17(19)2/h9-10,16,20-23,26-27H,2,4-8,11-15H2,1,3H3,(H,28,29)/b18-9+,19-10-/t16-,20-,21-,22+,23+,25-/m1/s1
SMILES (Click to copy)
[C@@H]1(O)C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([C@@](C)([H])CCCC(=O)O)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0026
PubChem CID
9547285

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 428.58
Topological Polar Surface Area 77.76
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 4
logP 5.59
Molar Refractivity 116.40

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Created at
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Updated at
17th Jan 2024