Structure Database (LMSD)

Common Name
(22E,24E)-1alpha,25-dihydroxy-26,27-dimethyl-22,23,24,24a-tetradehydro-24a-homovitamin D3
Systematic Name
(5Z,7E,22E,24E)-(1S,3R)-26,27-dimethyl-24a-homo-9,10-seco-5,7,10(19),22,24-cholestapentaene-1,3,25-triol
Synonyms
  • (22E,24E)-1alpha,25-dihydroxy-26,27-dimethyl-22,23,24,24a-tetradehydro-24a-homocholecalciferol
LM ID
LMST03020449
Formula
C30H46O3
Exact Mass
Calculate m/z
454.344696
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]

Biological Context

EB 1089 is a synthetic vitamin D analog that is 50-200 times more potent than calcitriol at inhibiting cell proliferation and differentiation, yet displays reduced calcemic activity compared to that of calcitriol.1 It has been shown to promote tumor regression in vitro by inducing apoptosis.2

This information has been provided by Cayman Chemical

References

1. Hansen, C.M., Hamberg, K.J., Binderup, E., et al. Seocalcitol (EB 1089): A vitamin D analogue of anti-cancer potential. Background, design, synthesis, pre-clinical and clinical evaluation. Curr. Pharm. Des. 6(7), 803-828 (2000).
2. James, S.Y., Mercer, E., Brady, M., et al. EB1089, a synthetic analogue of vitamin D, induces apoptosis in breast cancer cells in vivo and in vitro. Br. J. Pharmacol. 125(5), 953-962 (1998).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthesis and Biological Activity of 1a-hydroxylated Vitamin D Analogues with Poly-unsaturated Side Chains,
Vitamin D, 1994

String Representations

InChiKey (Click to copy)
LVLLALCJVJNGQQ-SEODYNFXSA-N
InChi (Click to copy)
InChI=1S/C30H46O3/c1-6-30(33,7-2)18-9-8-11-21(3)26-15-16-27-23(12-10-17-29(26,27)5)13-14-24-19-25(31)20-28(32)22(24)4/h8-9,11,13-14,18,21,25-28,31-33H,4,6-7,10,12,15-17,19-20H2,1-3,5H3/b11-8+,18-9+,23-13+,24-14-/t21-,25-,26-,27+,28+,29-/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(O)(CC)CC)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0539
PubChem CID
5288149
Cayman ID
21579
PDB ID
EB1
GuidePharm ID
2777

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 3
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 503.65
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 7.29
Molar Refractivity 139.24

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Created at
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Updated at
22nd Jan 2024