malacidin A (CHEBI:140173)

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CHEBI:140173 - malacidin A

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ChEBI ID	CHEBI:140173
ChEBI Name	malacidin A
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Definition	A homodetic cyclic peptide containing a 28-membered ring and consisting of 3-methyl-N-[(2E,4Z)-8-methylnona-2,4-dienoyl]-L-α-aspartyl, (2S)-2,3-diaminobutanoyl, D-valyl, L-lysyl, 3-hydroxy-L-α-aspartyl, L-α-aspartyl, glycyl, 3-methyl-D-α-aspartyl, L-valyl, and (4R)-methyl-L-proline joined in sequence and cyclised by condensation of the β-amino group of the 2,3-diaminobutanoyl residue with the carboxy group of the 4-methylproline residue.
Last Modified	20 February 2018
Submitter	Kristian Axelsen
Downloads	Molfile

Formula	C56H88N12O20
Net Charge	0
Average Mass	1249.384
Monoisotopic Mass	1248.62378
SMILES	CC(C)CC/C=C\C=C\C(=O)N[C@H](C(=O)N[C@@H]1C(=O)N[C@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(O)C(=O)O)C(=O)N[C@@H](CC(=O)O)C(=O)NCC(=O)N[C@H](C(C)C(=O)O)C(=O)N[C@@H](C(C)C)C(=O)N2C[C@H](C)C[C@H]2C(=O)NC1C)C(C)C(=O)O
InChI	InChI=1S/C56H88N12O20/c1-25(2)17-13-11-12-14-19-35(69)62-40(29(8)54(83)84)50(79)66-42-31(10)59-47(76)34-21-28(7)24-68(34)53(82)39(27(5)6)65-49(78)41(30(9)55(85)86)63-36(70)23-58-45(74)33(22-37(71)72)61-52(81)43(44(73)56(87)88)67-46(75)32(18-15-16-20-57)60-48(77)38(26(3)4)64-51(42)80/h11-12,14,19,25-34,38-44,73H,13,15-18,20-24,57H2,1-10H3,(H,58,74)(H,59,76)(H,60,77)(H,61,81)(H,62,69)(H,63,70)(H,64,80)(H,65,78)(H,66,79)(H,67,75)(H,71,72)(H,83,84)(H,85,86)(H,87,88)/b12-11-,19-14+/t28-,29?,30?,31?,32+,33+,34+,38-,39+,40+,41-,42+,43+,44?/m1/s1
InChIKey	USNOUEMKNKRWQT-ORRWAHHJSA-N

Wikipedia

Roles Classification

Chemical Role:	Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:	antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria. bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. calcium-dependent antibiotics Any antimicrobial agent whose activity is dependent on the presence of calcium ions.

ChEBI Ontology

Outgoing Relation(s)
	malacidin A (CHEBI:140173) has role antibacterial agent (CHEBI:33282)
	malacidin A (CHEBI:140173) has role bacterial metabolite (CHEBI:76969)
	malacidin A (CHEBI:140173) has role calcium-dependent antibiotics (CHEBI:140190)
	malacidin A (CHEBI:140173) is a homodetic cyclic peptide (CHEBI:24613)
	malacidin A (CHEBI:140173) is a lipopeptide (CHEBI:46895)

IUPAC Name
N-[(4S,7R,10S,13S,16S,22R,25S,29R,30aS)-10-(4-aminobutyl)-22-(1-carboxyethyl)-13-[carboxy(hydroxy)methyl]-16-(carboxymethyl)-7,25-diisopropyl-3,29-dimethyl-1,5,8,11,14,17,20,23,26-nonaoxotriacontahydropyrrolo[2,1-c][1,4,7,10,13,16,19,22,25]nonaazacyclooctacosin-4-yl]-3-methyl-N²-[(2E,4Z)-8-methylnona-2,4-dienoyl]-L-α-asparagine

Manual Xrefs	Databases
Malacidin	Wikipedia

Citations