Structure Database (LMSD)

Common Name
1alpha,25-dihydroxy-2alpha-hydroxymethyl-19-nor-20-epivitamin D3
Systematic Name
(7E)-(1R,2S,3R,20S)-2-hydroxymethyl-19-nor-9,10-seco-5,7-cholestadiene-1,3,25-triol
Synonyms
  • 1alpha,25-dihydroxy-2alpha-hydroxymethyl-19-nor-20-epicholecalciferol
LM ID
LMST03020560
Formula
C27H46O4
Exact Mass
Calculate m/z
434.33961
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)
New 1alpha,25-dihydroxy-19-norvitamin D3 compounds of high biological activity: synthesis and biological evaluation of 2-hydroxymethyl, 2-methyl, and 2-methylene analogues.,
J Med Chem, 1998
Pubmed ID: 9804706

String Representations

InChiKey (Click to copy)
HLHLJFDURNATDT-JNMQUVJDSA-N
InChi (Click to copy)
InChI=1S/C27H46O4/c1-18(7-5-13-26(2,3)31)22-11-12-23-20(8-6-14-27(22,23)4)10-9-19-15-24(29)21(17-28)25(30)16-19/h9-10,18,21-25,28-31H,5-8,11-17H2,1-4H3/b19-9-,20-10+/t18-,21-,22+,23-,24+,25+,27+/m0/s1
SMILES (Click to copy)
[C@@H]1(O)C/C(=C\C=C2\[C@]3([H])CC[C@@]([C@](C)([H])CCCC(O)(C)C)([H])[C@@]3(C)CCC\2)/C[C@@H](O)[C@@H]1CO

Other Databases

LIPIDBANK ID
VVD0661
PubChem CID
9547656

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 3
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 468.46
Topological Polar Surface Area 80.92
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 4
logP 5.90
Molar Refractivity 127.50

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Created at
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Updated at
23rd Jan 2024