Structure Database (LMSD)

Common Name
25-dihydroxy-19-nor-22-oxavitamin D3
Systematic Name
(7E)-(3S)-19-nor-22-oxa-9,10-seco-5,7-cholestadiene-3,25-diol
Synonyms
  • 25-dihydroxy-19-nor-22-oxacholecalciferol
LM ID
LMST03020569
Formula
C25H42O3
Exact Mass
Calculate m/z
390.313395
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)
Singly dehydroxylated A-ring analogues of 19-nor-1alpha,25-dihydroxyvitamin D3 and 19-nor-22-oxa-1alpha,25-dihydroxyvitamin D3: novel vitamin D3 analogues with potent transcriptional activity but extremely low affinity for vitamin D receptor.,
Biol Pharm Bull, 1998
Pubmed ID: 9881643

String Representations

InChiKey (Click to copy)
RTFHONCBOHAFCK-LUNNJSPDSA-N
InChi (Click to copy)
InChI=1S/C25H42O3/c1-18(28-16-15-24(2,3)27)22-12-13-23-20(8-6-14-25(22,23)4)11-10-19-7-5-9-21(26)17-19/h10-11,18,21-23,26-27H,5-9,12-17H2,1-4H3/b19-10+,20-11+/t18-,21-,22+,23-,25+/m0/s1
SMILES (Click to copy)
C1C/C(=C\C=C2\[C@]3([H])CC[C@@]([C@@](C)([H])OCCC(O)(C)C)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0670
PubChem CID
9547664

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 425.07
Topological Polar Surface Area 49.69
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 6.70
Molar Refractivity 117.17

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Created at
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Updated at
23rd Jan 2024