Structure database (LMSD)

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LM IDLMSP01080041
Common NameCapnine
Systematic Name(2R,3R)-2-amino-3-hydroxy-15-methylhexadecane-1-sulfonic acid
Synonyms-
Exact Mass
351.2443 (neutral)    Calculate m/z:
FormulaC17H37NO4S
CategorySphingolipids [SP]
Main ClassSphingoid bases [SP01]
Sub ClassSphingoid base analogs [SP0108]
PubChem CID11405452
InChIKeyXMTQSVIYISYLNK-DLBZAZTESA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C17H37NO4S/c1-15(2)12-10-8-6-4-3-5-7-9-11-13-17(19)16(18)14-23(20,21)22/h15-17,19H,3-14,18H2,1-2H3,(H,20,21,22)/t16-,17+/m0/s1
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SMILES
[C@H](N)(CS(=O)(=O)O)[C@H](O)CCCCCCCCCCCC(C)C
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StatusActive
SpeciesGliding bacteria of the genus Cytophaga.
ReferencesGodchaux, W., 3rd, and E. R. Leadbetter. 1984.
Sulfonolipids of gliding bacteria.
Structure of the N-acylaminosulfonates. J Biol Chem 259: 2982-2990.

Kamiyama, T., T. Umino, Y. Itezono, Y. Nakamura, T. Satoh, and K. Yokose. 1995.
Sulfobacins A and B, novel von Willebrand factor receptor antagonists. II. Structural elucidation.
J Antibiot (Tokyo) 48: 929-936.

White, R. H. 1984.
Biosynthesis of the sulfonolipid 2-amino-3-hydroxy-15-methylhexadecane-1-sulfonic acid
in the gliding bacterium Cytophaga johnsonae.
J Bacteriol 159: 42-46.

Abbanat, D. R., W. Godchaux, 3rd, G. Polychroniou, and E. R. Leadbetter. 1985.
Biosynthesis of a sulfonolipid in gliding bacteria.
Biochem Biophys Res Commun 130: 873-878.
Calculated physicochemical properties (?):
 Heavy Atoms23Rings0Aromatic Rings0Rotatable Bonds15
 van der Waals
Molecular Volume
367.33Topological Polar
Surface Area
100.62Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
4
 logP5.62Molar
Refractivity
97.44