Structure database (LMSD)

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LM IDLMST05050024
Common NameSqualamine (W)
Systematic Name3β-N-1-(N-[3-(4-aminobutyl)]- 1,3-diaminopropane)-7α,24R-dihydroxy-5α-
cholestane 24-sulfate
Synonyms-
Exact Mass
627.4645 (neutral)    Calculate m/z:
FormulaC34H65N3O5S
CategorySterol Lipids [ST]
Main ClassSteroid conjugates [ST05]
Sub ClassOther Steroid conjugates [ST0505]
PubChem CID72495
KEGG IDC16841
CHEBI ID80765
InChIKeyUIRKNQLZZXALBI-MSVGPLKSSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C34H65N3O5S/c1-23(2)31(42-43(39,40)41)12-9-24(3)27-10-11-28-32-29(14-16-34(27,28)5)33(4)15-13-26(21-25(33)22-30(32)38)37-20-8-19-36-18-7-6-17-35/h23-32,36-38H,6-22,35H2,1-5H3,(H,39,40,41)/t24-,25-,26+,27-,28+,29+,30-,31-,32+,33+,34-/m1/s1
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SMILES
[C@]12([C@H](O)C[C@@]3([H])C[C@@H](NCCCNCCCCN)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@]([H])([C@@](C)([H])CC[C@@H](OS(=O)(=O)O)C(C)C)CC[C@@]21[H])[H]
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StatusActive
ReferencesSqualamine: an aminosterol antibiotic from the shark.
Moore, K S; S Wehrli, H Roder, M Rogers, J N Forrest, D McCrimmon, M Zasloff
PNAS (USA) 90 (4): 1354-8. PMC: 45871
Calculated physicochemical properties (?):
 Heavy Atoms43Rings4Aromatic Rings0Rotatable Bonds16
 van der Waals
Molecular Volume
642.78Topological Polar
Surface Area
133.91Hydrogen
Bond Donors
5Hydrogen
Bond Acceptors
5
 logP8.80Molar
Refractivity
177.23