LIPID MAPS

Structure Database (LMSD)

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Common Name

Granadaene

Systematic Name

(2S)-5-amino-2-(27R-O-α-L-rhamnopyranosyl-2E,4E,6E,8E,10E,12E,14E,16E,18E,20E,22E,24E-octacosadodecaenoyl)pentanoic acid

Synonyms

12-Granadaene
alpha-N-(27R-O-alpha-L-rhamnopyranosyl-2E,4E,6E,8E,10E,12E,14E,16E,18E,20E,22E,24E-octacosadodecaenoyl) L-ornithine

LM ID

LMFA08020282

Formula

C₃₉H₅₂N₂O₈

Exact Mass

Calculate m/z

676.372368

Status

Active

Show lipids differing only in stereochemistry/bond geometry

No other lipid differing only in stereochemistry/bond geometry found

Classification

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Streptococcus agalactiae (#1311)

Bacilli (#91061)

Clarifying the structure of granadaene: total synthesis of related analogue [2]-granadaene and confirmation of its absolute stereochemistry.,
Bioorg Med Chem, 2012

Pubmed ID: 23043725

String Representations

InChiKey (Click to copy)

PPFISAQUKQQDHW-MXBVYNHDSA-N

InChi (Click to copy)

InChI=1S/C39H52N2O8/c1-31(48-39-37(45)36(44)35(43)32(2)49-39)27-24-22-20-18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-21-23-25-29-34(42)41-33(38(46)47)28-26-30-40/h3-25,29,31-33,35-37,39,43-45H,26-28,30,40H2,1-2H3,(H,41,42)(H,46,47)/b4-3+,7-5+,8-6+,11-9+,12-10+,15-13+,16-14+,19-17+,20-18+,23-21+,24-22+,29-25+/t31-,32+,33+,35+,36-,37-,39-/m1/s1

SMILES (Click to copy)

C[C@@H]1O[C@@H](O[C@@H](C/C=C/C=C/C=C/C=C/C=C/C=C/C=C/C=C/C=C/C=C/C=C/C=C/C(N[C@H](C(O)=O)CCCN)=O)C)[C@H](O)[C@H](O)[C@H]1O