Structure database (LMSD)

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LM IDLMST05050025
Common NameDendrogenin A
Systematic Name5α-hydroxy-6β-[2-(1H-imidazol-4-yl)-ethylamino]-cholestan-3β-ol
Synonyms-
Exact Mass
513.4294 (neutral)    Calculate m/z:
FormulaC32H55N3O2
CategorySterol Lipids [ST]
Main ClassSteroid conjugates [ST05]
Sub ClassOther Steroid conjugates [ST0505]
PubChem CID9806490
InChIKeyAVFNYTPENXWWCA-BULFVYHESA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C32H55N3O2/c1-21(2)7-6-8-22(3)26-9-10-27-25-17-29(34-16-13-23-19-33-20-35-23)32(37)18-24(36)11-15-31(32,5)28(25)12-14-30(26,27)4/h19-22,24-29,34,36-37H,6-18H2,1-5H3,(H,33,35)/t22-,24+,25+,26-,27+,28+,29-,30-,31-,32+/m1/s1
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SMILES
[C@]12(C[C@@H](NCCC3=CN=CN3)[C@@]3(O)C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@]([H])([C@@](C)([H])CCCC(C)C)CC[C@@]21[H])[H]
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StatusActive
ReferencesDendrogenin A arises from cholesterol and histamine metabolism and shows cell differentiation and anti-tumour properties.
de Medina P, Paillasse MR, Segala G, Voisin M, Mhamdi L, Dalenc F,
Lacroix-Triki M,Filleron T, Pont F, Saati TA, Morisseau C,Hammock BD,
Silvente-Poirot S, Poirot M.
Nat Commun. 2013;4:1840.
Calculated physicochemical properties (?):
 Heavy Atoms37Rings5Aromatic Rings1Rotatable Bonds9
 van der Waals
Molecular Volume
534.76Topological Polar
Surface Area
81.17Hydrogen
Bond Donors
4Hydrogen
Bond Acceptors
3
 logP7.10Molar
Refractivity
151.96