Molecule

Coumermycin A1

AlkaPlorer ID: AK004277

Synonym: None

IUPAC Name: 2-N,4-N-bis[4-hydroxy-7-[(2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyl-4-(5-methyl-1H-pyrrole-2-carbonyl)oxyoxan-2-yl]oxy-8-methyl-2-oxochromen-3-yl]-3-methyl-1H-pyrrole-2,4-dicarboximidic acid

Structure

SMILES: CO[C@@H]1[C@@H](OC(=O)C2=CC=C(C)N2)[C@@H](O)[C@H](OC2=CC=C3C(O)=C(N=C(O)C4=CNC(C(O)=NC5=C(O)C6=CC=C(O[C@@H]7OC(C)(C)[C@H](OC)[C@@H](OC(=O)C8=CC=C(C)N8)[C@H]7O)C(C)=C6OC5=O)=C4C)C(=O)OC3=C2C)OC1(C)C

InChI: InChI=1S/C55H59N5O20/c1-21-12-16-29(57-21)48(67)77-42-38(63)52(79-54(6,7)44(42)71-10)73-31-18-14-26-36(61)34(50(69)75-40(26)24(31)4)59-46(65)28-20-56-33(23(28)3)47(66)60-35-37(62)27-15-19-32(25(5)41(27)76-51(35)70)74-53-39(64)43(45(72-11)55(8,9)80-53)78-49(68)30-17-13-22(2)58-30/h12-20,38-39,42-45,52-53,56-58,61-64H,1-11H3,(H,59,65)(H,60,66)/t38-,39-,42+,43+,44-,45-,52-,53-/m1/s1

InChIKey: WTIJXIZOODAMJT-DHFGXMAYSA-N

Reference

Identification of the Coumermycin A <sub>1</sub> Biosynthetic Gene Cluster of <i>Streptomyces rishiriensis</i> DSM 40489

PubChem CID: 163186164

CAS: 4434-05-3

LOTUS: LTS0239572

NPASS: NPC315858

{

NPAtlas: NPA024721

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Streptomyces rishiriensis	Streptomyces	Streptomycetaceae	Kitasatosporales	Actinomycetes	Actinomycetota	None	Bacteria

Properties Information

Molecule Weight: 1110.0919999999996

TPSA？: 361.87

MolLogP？: 6.340000000000007

Number of H-Donors: 9

Number of H-Acceptors: 20

RingCount: 9

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Escherichia coli	DNA gyrase	IC50	30.0	nM	10.1016/j.bmc.2016.04.043
Escherichia coli	Escherichia coli	MIC	6.25	ug.mL-1	10.1016/j.bmc.2016.04.043
Homo sapiens	MCF7	IC50	2000.0	nM	10.1021/acs.jmedchem.8b00825
Homo sapiens	SK-BR-3	IC50	2000.0	nM	10.1021/acs.jmedchem.8b00825
Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	12.5	ug.mL-1	10.1016/j.bmc.2016.04.043
Staphylococcus aureus	DNA gyrase	IC50	6.0	nM	10.1016/j.bmc.2016.04.043
Staphylococcus aureus	Staphylococcus aureus	MIC	0.0012	ug.mL-1	10.1016/j.bmc.2016.04.043
Staphylococcus aureus	Topoisomerase IV	IC50	100000.0	nM	10.1016/j.bmc.2016.04.043
Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	0.78	ug.mL-1	10.1016/j.bmc.2016.04.043
None	Unchecked	IC50	5000.0	nM	10.1016/j.bmc.2016.04.043

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT011269	CO[C@@H]1[C@@H](OC(=O)c2ccc(C)[nH]2)[C@@H](O)[C@H](Oc2ccc3c(O)c(NC(=O)c4c[nH]c(C(=O)Nc5c(O)c6ccc(O[C@@H]7OC(C)(C)[C@H](OC)[C@@H](OC(=O)c8ccc(C)[nH]8)[C@H]7O)c(C)c6oc5=O)c4C)c(=O)oc3c2C)OC1(C)C>>*SC(=O)c1ccc(C)[nH]1	MNXR135528
AKRT011270	CO[C@@H]1[C@@H](OC(=O)c2ccc(C)[nH]2)[C@@H](O)[C@H](Oc2ccc3c(O)c(NC(=O)c4c[nH]c(C(=O)Nc5c(O)c6ccc(O[C@@H]7OC(C)(C)[C@H](OC)[C@@H](OC(=O)c8ccc(C)[nH]8)[C@H]7O)c(C)c6oc5=O)c4C)c(=O)oc3c2C)OC1(C)C>>CO[C@@H]1[C@@H](O)[C@@H](O)[C@H](Oc2ccc3c(O)c(NC(=O)c4c[nH]c(C(=O)Nc5c(O)c6ccc(O[C@@H]7OC(C)(C)[C@H](OC)[C@@H](O)[C@H]7O)c(C)c6oc5=O)c4C)c(=O)oc3c2C)OC1(C)C	MNXR135528