Structure Database (LMSD)

Common Name
24,24-difluoro-1alpha,25-dihydroxy-24a-homovitamin D3
Systematic Name
(5Z,7E)-(1S,3R)-24,24-difluoro-24a-homo-9,10-seco-5,7,10(19)-cholestatrien-1,3,25-triol
Synonyms
  • 24,24-difluoro-1alpha,25-dihydroxy-24a-homocholecalciferol
LM ID
LMST03020316
Formula
C28H44O3F2
Exact Mass
Calculate m/z
466.325853
Status
Curated
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)
26,27-Diethyl-1 alpha,25-dihydroxyvitamin D3 and 24,24-difluoro-24-homo-1 alpha,25-dihydroxyvitamin D3: highly potent inducer for differentiation of human leukemia cells HL-60.,
Chem Pharm Bull (Tokyo), 1987
Pubmed ID: 3435961

String Representations

InChiKey (Click to copy)
NPQFBPMBIMOXJU-YQMUYLDZSA-N
InChi (Click to copy)
InChI=1S/C28H44F2O3/c1-18(12-14-28(29,30)17-26(3,4)33)23-10-11-24-20(7-6-13-27(23,24)5)8-9-21-15-22(31)16-25(32)19(21)2/h8-9,18,22-25,31-33H,2,6-7,10-17H2,1,3-5H3/b20-8+,21-9-/t18-,22-,23-,24+,25+,27-/m1/s1
SMILES (Click to copy)
[C@@H]1(O)C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([C@@](C)([H])CCC(F)(F)CC(O)(C)C)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0350
PubChem CID
9547463

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 3
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 486.47
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 7.49
Molar Refractivity 131.03

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Created at
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Updated at
15th Feb 2022