Compound ID | 732

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Decaplanin

Synonym(s): M 861410

Class: Glycopeptide

Agent Type: Natural product; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Cell wall synthesis inhibitor
Description: Natural product from an actinomycete strain Y-86,36910 (putatively identified as Kibdelosporangium; also produced by Amycolatopsis orientalis); Chin NX, Niu WW and Neu HC. Decaplanin, a novel glycopeptide antibiotic. 31st-ICAAC 1991;167.
Institute where first reported: Aventis (Sanofi Aventis, France)
Year first mentioned: 1991
Highest development stage: Preclinical
Development status: Experimental
Reason dropped: Fails to show non-inferiority to vancomycin
Chemical structure(s):
Click here for structure editor
Molecular weight: 1560.95
Iso. SMILES: CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)C(C(C(=O)NC(C(=O)NC5C(=O)NC7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9O)O)C(NC(=O)C(C(C%10=CC=C(O4)C=C%10)OC%11CC(C(C(O%11)C)O)(C)N)NC7=O)C(=O)O)CC(=O)N)NC(=O)C(CC(C)C)NC)O)Cl)CO)O)O)O)O)O
InChI Key: SJSZMXQSCZCGFO-UHFFFAOYSA-N
Can. SMILES: CC(C)CC(C(=O)NC1C(C2=CC=C(C(=C2)Cl)OC3=C(C4=CC(=C3)C(C(=O)NC5C6=CC=C(C(=C6)C7=C(C=C(C=C7C(C(=O)O)NC(=O)C(C(C8=CC=C(C=C8)O4)OC9CC(C)(C(C(C)O9)O)N)NC5=O)O)O)O)NC(=O)C(CC(=O)N)NC1=O)OC%10C(C(C(C(CO)O%10)O)O)OC%11C(C(C(C(C)O%11)O)O)O)O)NC
InChI: InChI=1S/C72H86ClN9O28/c1-25(2)15-37(76-6)63(95)81-51-54(89)30-10-14-41(36(73)17-30)106-43-19-31-18-42(60(43)109-71-61(57(92)55(90)44(24-83)107-71)110-70-58(93)56(91)53(88)26(3)104-70)105-33-11-7-28(8-12-33)59(108-46-23-72(5,75)62(94)27(4)103-46)52-68(100)80-50(69(101)102)35-20-32(84)21-40(86)47(35)34-16-29(9-13-39(34)85)48(65(97)82-52)79-66(98)49(31)78-64(96)38(22-45(74)87)77-67(51)99/h7-14,16-21,25-27,37-38,44,46,48-59,61-62,70-71,76,83-86,88-94H,15,22-24,75H2,1-6H3,(H2,74,87)(H,77,99)(H,78,96)(H,79,98)(H,80,100)(H,81,95)(H,82,97)(H,101,102)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/195570
Guide to Pharmacology: decaplanin
Citations:
  • https://patents.google.com/patent/EP0356894A1/en
  • https://doi.org/10.1128/aac.36.4.873
    • Patent: EP0356894A1

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