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Nbeta-acetylstreptothricin D

AlkaPlorer ID: AK033490

Synonym: 'Antibiotic AN 201II', '2-{(3S)-3-Acetamido-6-{(3S)-3-amino-6-{(3S)-3,6-diaminohexanoylamino}hexanoylamino}hexanoylamino}-4-O-carbamoyl-2-deoxy-N-(3aS,7R,7aS)-7-hydroxy-4-oxo-3a,4,5,6,7,7a-hexahydro-1H-imidazo4,5-cp yridin-2-yl-beta-D-gulopyranosylamine', '(2R,3S,4R)-Nβ-acetylstreptothricin D', 'AN-201 II'

IUPAC Name: [(2R,3R,4S,5R,6R)-6-[[(3aS,7R,7aS)-7-hydroxy-4-oxo-1,3a,5,6,7,7a-hexahydroimidazo[4,5-c]pyridin-2-yl]amino]-5-[[(3S)-3-acetamido-6-[[(3S)-3-amino-6-[[(3S)-3,6-diaminohexanoyl]amino]hexanoyl]amino]hexanoyl]amino]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl] carbamate

Structure

SMILES: CC(=O)N[C@@H](CCCNC(=O)C[C@@H](N)CCCNC(=O)C[C@@H](N)CCCN)CC(=O)N[C@@H]1[C@H](O)[C@@H](OC(N)=O)[C@@H](CO)O[C@H]1NC1=N[C@@H]2C(=O)NC[C@@H](O)[C@H]2N1

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InChI: InChI=1S/C33H60N12O11/c1-16(47)41-19(7-4-10-39-23(50)12-18(36)6-3-9-38-22(49)11-17(35)5-2-8-34)13-24(51)42-27-28(52)29(56-32(37)54)21(15-46)55-31(27)45-33-43-25-20(48)14-40-30(53)26(25)44-33/h17-21,25-29,31,46,48,52H,2-15,34-36H2,1H3,(H2,37,54)(H,38,49)(H,39,50)(H,40,53)(H,41,47)(H,42,51)(H2,43,44,45)/t17-,18-,19-,20+,21+,25+,26-,27+,28-,29-,31+/m0/s1

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InChIKey: WPMGFKKSCCXUAK-YFZUDYRPSA-N

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Properties Information

Molecule Weight: 800.9160000000002

TPSA？: 382.22

MolLogP？: -6.348800000000017

Number of H-Donors: 14

Number of H-Acceptors: 17

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus subtilis Bacillus subtilis MIC 128.0 ug.mL-1 10.1021/np2000733
Candida albicans Candida albicans MIC 128.0 ug.mL-1 10.1021/np2000733
Enterococcus faecalis Enterococcus faecalis MIC 128.0 ug.mL-1 10.1021/np2000733
Escherichia coli Escherichia coli MIC 128.0 ug.mL-1 10.1021/np2000733
Homo sapiens A549 IC50 10000.0 nM 10.1021/np2000733
Homo sapiens HeLa IC50 10000.0 nM 10.1021/np2000733
Homo sapiens HepG2 IC50 10000.0 nM 10.1021/np2000733
Morganella morganii Morganella morganii MIC 128.0 ug.mL-1 10.1021/np2000733
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 128.0 ug.mL-1 10.1021/np2000733
Mycolicibacterium smegmatis Mycolicibacterium smegmatis MIC 128.0 ug.mL-1 10.1021/np2000733
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 128.0 ug.mL-1 10.1021/np2000733
Staphylococcus aureus Staphylococcus aureus MIC 128.0 ug.mL-1 10.1021/np2000733

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT004638 CC(=O)[CoA].NCCC[C@H](N)CC(=O)NCCC[C@H](N)CC(=O)NCCC[C@H](N)CC(=O)N[C@@H]1[C@H](O)[C@@H](OC(N)=O)[C@@H](CO)O[C@H]1/N=C1/N[C@@H]2C(=O)NC[C@@H](O)[C@H]2N1>>CC(=O)N[C@@H](CCCNC(=O)C[C@@H](N)CCCNC(=O)C[C@@H](N)CCCN)CC(=O)N[C@@H]1[C@H](O)[C@@H](OC(N)=O)[C@@H](CO)O[C@H]1/N=C1\N[C@@H]2C(=O)NC[C@@H](O)[C@H]2N1 57004