Structure Database (LMSD)

Common Name
1alpha,25-dihydroxy-(26,26)-(27,27)-diethanovitamin D3
Systematic Name
(5Z,7E)-(1S,3R)-(26,26)-(27,27)-diethano-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol
Synonyms
  • 1alpha,25-dihydroxy-(26,26)-(27,27)-diethanocholecalciferol
LM ID
LMST03020481
Formula
C31H48O3
Exact Mass
Calculate m/z
468.360345
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)
Ultrasonically Induced Conjugate Addition of Iodides to Electron-Deficient Olefins and Its Application to the Synthesis of Side-Chain Analogs of the Hormone 1a,25-Dihydroxyvitamin D3,
J Org Chem, 1993

String Representations

InChiKey (Click to copy)
XLOOAPQXGQUZDQ-FLOOHNOFSA-N
InChi (Click to copy)
InChI=1S/C31H48O3/c1-20(6-4-17-31(34,24-10-11-24)25-12-13-25)27-14-15-28-22(7-5-16-30(27,28)3)8-9-23-18-26(32)19-29(33)21(23)2/h8-9,20,24-29,32-34H,2,4-7,10-19H2,1,3H3/b22-8+,23-9-/t20-,26-,27-,28+,29+,30-/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)(C4CC4)C4CC4)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

CHEBI ID
169498
LIPIDBANK ID
VVD0571
PubChem CID
9547585

Calculated Physicochemical Properties

Heavy Atoms 34
Rings 5
Aromatic Rings 0
Rotatable Bonds 8
Van der Waals Molecular Volume 501.51
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 7.34
Molar Refractivity 139.67

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Created at
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Updated at
26th Mar 2024