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Enterobactin

AlkaPlorer ID: AK016332

Synonym: None

IUPAC Name: N-[(3S,7S,11S)-7,11-bis[(2,3-dihydroxybenzoyl)amino]-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl]-2,3-dihydroxybenzamide

Structure

SMILES: O=C1OC[C@H](N=C(O)C2=CC=CC(O)=C2O)C(=O)OC[C@H](N=C(O)C2=C(O)C(O)=CC=C2)C(=O)OC[C@@H]1N=C(O)C1=CC=CC(O)=C1O

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InChI: InChI=1S/C30H27N3O15/c34-19-7-1-4-13(22(19)37)25(40)31-16-10-46-29(44)18(33-27(42)15-6-3-9-21(36)24(15)39)12-48-30(45)17(11-47-28(16)43)32-26(41)14-5-2-8-20(35)23(14)38/h1-9,16-18,34-39H,10-12H2,(H,31,40)(H,32,41)(H,33,42)/t16-,17-,18-/m0/s1

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InChIKey: SERBHKJMVBATSJ-BZSNNMDCSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Escherichia coli Escherichia Enterobacteriaceae Enterobacterales Gammaproteobacteria Pseudomonadota None Bacteria

Properties Information

Molecule Weight: 669.5520000000004

TPSA？: 298.05

MolLogP？: 0.9833999999999994

Number of H-Donors: 9

Number of H-Acceptors: 15

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Escherichia coli Escherichia coli Growth zone 0.0 mM 10.1021/jm00122a013
Escherichia coli Escherichia coli Growth zone 28.0 mM 10.1021/jm00122a013
Escherichia coli Escherichia coli Growth zone 40.0 mM 10.1021/jm00122a013
Escherichia coli Escherichia coli Growth zone nan None 10.1021/jm00122a013
Escherichia coli Escherichia coli Inhibitory diameter 25.0 mM 10.1021/jm00381a010
Escherichia coli Escherichia coli Inhibitory diameter 25.0 mM 10.1021/jm00381a011
Escherichia coli Escherichia coli Inhibitory diameter nan None 10.1021/jm00381a010
Escherichia coli Escherichia coli Inhibitory diameter nan None 10.1021/jm00381a011
Escherichia coli Escherichia coli Zone of stimulation 24.0 mM 10.1016/S0960-894X(01)80456-X
Escherichia coli Escherichia coli Zone of stimulation 30.0 mM 10.1016/S0960-894X(01)80456-X
Escherichia coli Escherichia coli Zone of stimulation 38.0 mM 10.1016/S0960-894X(01)80456-X
Escherichia coli Escherichia coli Zone of stimulation 40.0 mM 10.1016/S0960-894X(01)80456-X
Homo sapiens Serotransferrin Fe removed 6.0 % 10.1021/jm00357a022
Vibrio cholerae Vibrio cholerae Growth zone 0.0 mM 10.1021/jm00122a013
Vibrio cholerae Vibrio cholerae Growth zone 22.0 mM 10.1021/jm00122a013
Vibrio cholerae Vibrio cholerae Growth zone 28.0 mM 10.1021/jm00122a013
None Unchecked Kd 0.5 nM 10.1021/jm500325k
None Unchecked pM 35.5 None 10.1021/jm00197a001
None Unchecked Ratio 120.0 None 10.1021/jm00357a022

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT000448 *C(=O)[C@H](CO)NC(=O)c1cccc(O)c1O.*C(=O)[C@H](CO)NC(=O)c1cccc(O)c1O.*C(=O)[C@H](CO)NC(=O)c1cccc(O)c1O>>O=C(N[C@H]1COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC1=O)c1cccc(O)c1O ENTG-RXN
AKRT021758 Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OC(=O)[C@@H](N)CO)[C@@H](O)[C@H]1O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OC(=O)c2cccc(O)c2O)[C@@H](O)[C@H]1O>>O=C(N[C@H]1COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC1=O)c1cccc(O)c1O MNXR134498
AKRT022509 O=C(N[C@H](CO)C(=O)O)c1cccc(O)c1O.O=C(N[C@H](CO)C(=O)O)c1cccc(O)c1O.O=C(N[C@H](CO)C(=O)O)c1cccc(O)c1O>>O=C(N[C@H]1COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC1=O)c1cccc(O)c1O MNXR183777
AKRT022522 O=C(N[C@H]1COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC1=O)c1cccc(O)c1O.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1>>O=C(N[C@H]1COC(=O)[C@@H](NC(=O)c2cc([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)cc(O)c2O)COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC1=O)c1cccc(O)c1O.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1 None
AKRT022523 O=C(N[C@H]1COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC1=O)c1cccc(O)c1O.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1>>O=C(N[C@H]1COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC(=O)[C@@H](NC(=O)c2cc([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)cc(O)c2O)COC1=O)c1cccc(O)c1O RXN-20004
AKRT022524 O=C(N[C@H]1COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC1=O)c1cccc(O)c1O>>O=C(NC(CO)C(=O)O)c1cccc(O)c1O MNXR153455
AKRT022525 O=C(N[C@H]1COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC1=O)c1cccc(O)c1O>>O=C(N[C@@H](CO)C(=O)O)c1cccc(O)c1O RXN0-1661
AKRT022526 O=C(N[C@H]1COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC1=O)c1cccc(O)c1O>>O=C(N[C@@H](COC(=O)[C@H](COC(=O)[C@H](CO)NC(=O)c1cccc(O)c1O)NC(=O)c1cccc(O)c1O)C(=O)O)c1cccc(O)c1O RXN-14477
AKRT022527 O=C(N[C@H]1COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC1=O)c1cccc(O)c1O>>O=C1N[C@H]2COC(=O)[C@@H]3COC(=O)[C@H](COC2=O)NC(=O)c2cccc4c2O[Fe-3]25(Oc6cccc1c6O2)(O4)Oc1cccc(c1O5)C(=O)N3 RXN-20002
AKRT022528 O=C(N[C@H]1COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC1=O)c1cccc(O)c1O>>O=C1N[C@H]2CO[C@@H](O)[C@@H]3CO[C@H](O)[C@@H](CO[C@@H]2O)NC(=O)c2cccc4c2O[Fe]25(Oc6cccc1c6O2)(Oc1cccc(c1O5)C(=O)N3)O4 MNXR157449
AKRT023613 O=C1N[C@H]2COC(=O)[C@@H]3COC(=O)[C@H](COC2=O)NC(=O)c2cccc4c2O[Fe-3]25(Oc6cccc1c6O2)(Oc1cccc(c1O5)C(=O)N3)O4.O=C1N[C@H]2COC(=O)[C@@H]3COC(=O)[C@H](COC2=O)NC(=O)c2cccc4c2O[Fe-3]25(Oc6cccc1c6O2)(Oc1cccc(c1O5)C(=O)N3)O4>>O=C(N[C@H]1COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC(=O)[C@@H](NC(=O)c2cccc(O)c2O)COC1=O)c1cccc(O)c1O MNXR135813