Structure Database (LMSD)

H H HO OH OH H
Common Name
1alpha,25-dihydroxy-26,26, 26,27,27,27-hexamethylvitamin D3
Systematic Name
(5Z,7E)-(1S,3R)-26,26, 26,27,27,27-hexamethyl-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol
Synonyms
  • 1alpha,25-dihydroxy-26,26,26,27,27,27-hexamethylcholecalciferol
LM ID
LMST03020532
Formula
C33H56O3
Exact Mass
Calculate m/z
500.422945
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Secosteroids [ST03]
Vitamin D3 and derivatives [ST0302]

String Representations

InChiKey (Click to copy)
LRXRKNNUOLDWCL-WIEVNKIHSA-N
InChi (Click to copy)
InChI=1S/C33H56O3/c1-22(12-10-19-33(36,30(3,4)5)31(6,7)8)27-16-17-28-24(13-11-18-32(27,28)9)14-15-25-20-26(34)21-29(35)23(25)2/h14-15,22,26-29,34-36H,2,10-13,16-21H2,1,3-9H3/b24-14+,25-15-/t22-,26-,27-,28+,29+,32-/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)(C(C)(C)C)C(C)(C)C)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Dokdonia donghaensis (#326320)
Flavobacteriia (#117743)
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

Other Databases

LIPIDBANK ID
VVD0623
PubChem CID
9547636

Calculated Physicochemical Properties

Heavy Atoms 36
Rings 3
Aromatic Rings 0
Rotatable Bonds 8
Van der Waals Molecular Volume 560.83
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 8.62
Molar Refractivity 153.14

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Created at
-
Updated at
2nd Feb 2024