Compound ID | 2126

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Moiramide A, B, C

Class: Natural product antibiotic

Spectrum of activity: Gram-positive
Details of activity: Inhibits fatty acid synthesis by binding to AccABCD which catalyzes the first committed step in fatty acid synthesis (carboxylation of acetyl-CoA by acetyl-CoA carboxylase, ACC).
Description: Natural product produced by Pseudomonas fluorescens
Year first mentioned: 1994
Development status: Experimental
Chemical structure(s):
Moiramide A
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Molecular weight: 285.34
Iso. SMILES: C/C=C/C=C/C=C/C(=O)N[C@@H](CC(=O)O)C1=CC=CC=C1
InChI Key: QOUZNKNYXDVAOK-QNIMBLPESA-N
Can. SMILES: C/C=C/C=C/C=C/C(=O)N[C@@H](CC(=O)O)C1=CC=CC=C1
InChI: InChI=1S/C17H19NO3/c1-2-3-4-5-9-12-16(19)18-15(13-17(20)21)14-10-7-6-8-11-14/h2-12,15H,13H2,1H3,(H,18,19)(H,20,21)/b3-2+,5-4+,12-9+/t15-/m0/s1
Moiramide B
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Molecular weight: 453.53
Iso. SMILES: C/C=C/C=C/C(=O)N[C@@H](CC(=O)N[C@@H](C(C)C)C(=O)[C@H]1[C@@H](C(=O)NC1=O)C)C2=CC=CC=C2
InChI Key: WMLLJSBRSSYYPT-PQUJRENYSA-N
Can. SMILES: C/C=C/C=C/C(=O)N[C@@H](CC(=O)N[C@@H](C(C)C)C(=O)[C@H]1[C@H](C)C(=O)NC1=O)C2=CC=CC=C2
InChI: InChI=1S/C25H31N3O5/c1-5-6-8-13-19(29)26-18(17-11-9-7-10-12-17)14-20(30)27-22(15(2)3)23(31)21-16(4)24(32)28-25(21)33/h5-13,15-16,18,21-22H,14H2,1-4H3,(H,26,29)(H,27,30)(H,28,32,33)/b6-5+,13-8+/t16-,18-,21+,22-/m0/s1
Moiramide C
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Molecular weight: 495.57
Iso. SMILES: C/C=C/C=C/C=C/C(=O)N[C@@H](CC(=O)N[C@@H](C(C)C)C(=O)[C@@]1([C@@H](C(=O)NC1=O)C)O)C2=CC=CC=C2
InChI Key: MDWPTHONDMTCBU-DEOIRRQKSA-N
Can. SMILES: C/C=C/C=C/C=C/C(=O)N[C@@H](CC(=O)N[C@@H](C(C)C)C(=O)[C@@]1([C@H](C)C(=O)NC1=O)O)C2=CC=CC=C2
InChI: InChI=1S/C27H33N3O6/c1-5-6-7-8-12-15-21(31)28-20(19-13-10-9-11-14-19)16-22(32)29-23(17(2)3)24(33)27(36)18(4)25(34)30-26(27)35/h5-15,17-18,20,23,36H,16H2,1-4H3,(H,28,31)(H,29,32)(H,30,34,35)/b6-5+,8-7+,15-12+/t18-,20+,23+,27-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/moiramide-B
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/10391070
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/10108000
Citations:
  • https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/cmdc.202200631
  • https://pubs.acs.org/doi/pdf/10.1021/acs.biochem.6b00641
  • https://pubs.acs.org/doi/pdf/10.1021/jo00087a020

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