Structure Database (LMSD)

Common Name
(22E,24E,26E)-1alpha,26b-dihydroxy-22,23,24,25,26,26a-hexadehydro-26a,26b-dihomo-27-norvitamin D3
Systematic Name
(5Z,7E,22E,24E,26E)-(1S,3R)-26a,26b-dihomo-27-nor-9,10-seco-5,7,10(19),22,24,26(26a)-cholestahexaene-1,3,26b-triol
Synonyms
  • (22E,24E,26E)-1alpha,26b-dihydroxy-22,23,24,25,26,26a-hexadehydro-26a,26b-dihomo-27-norcholecalciferol
LM ID
LMST03020312
Formula
C28H40O3
Exact Mass
Calculate m/z
424.297745
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 Biological Activity of 1a-Hydroxylated Vitamin D3 Analogues with Hydroxylated Side Chains, Multi-Homologated in The 24- or 24,26,27-Positions,
Vitamin D, 1991

String Representations

InChiKey (Click to copy)
DHSBJCJEENJGKO-QDVNLBANSA-N
InChi (Click to copy)
InChI=1S/C28H40O3/c1-20(10-7-5-4-6-8-17-29)25-14-15-26-22(11-9-16-28(25,26)3)12-13-23-18-24(30)19-27(31)21(23)2/h4-8,10,12-13,20,24-27,29-31H,2,9,11,14-19H2,1,3H3/b5-4+,8-6+,10-7+,22-12+,23-13-/t20-,24-,25-,26+,27+,28-/m1/s1
SMILES (Click to copy)
[C@@H]1(O)C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([C@@](C)([H])/C=C/C=C/C=C/CO)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

CHEBI ID
176865
LIPIDBANK ID
VVD0343
PubChem CID
9547460

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 466.41
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 6.28
Molar Refractivity 129.91

Admin

Created at
-
Updated at
31st May 2022