Navigation

name Structure Reference Source Properties Activities Metabolism

Rebeccamycin

AlkaPlorer ID: AK011771

Synonym: None

IUPAC Name: 5,21-dichloro-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione

Structure

SMILES: CO[C@H]1[C@H](O)[C@@H](O)[C@H](N2C3=C(Cl)C=CC=C3C3=C2C2=C(C4=C3C(=O)N=C4O)C3=CC=CC(Cl)=C3N2)O[C@@H]1CO

copy

InChI: InChI=1S/C27H21Cl2N3O7/c1-38-24-13(8-33)39-27(23(35)22(24)34)32-20-10(5-3-7-12(20)29)15-17-16(25(36)31-26(17)37)14-9-4-2-6-11(28)18(9)30-19(14)21(15)32/h2-7,13,22-24,27,30,33-35H,8H2,1H3,(H,31,36,37)/t13-,22-,23-,24-,27-/m1/s1

copy

InChIKey: QEHOIJJIZXRMAN-QZQSLCQPSA-N

copy

Source

Species Genus Family Order Class Phylum Kingdom Domain
None Nocardia Nocardiaceae Mycobacteriales Actinomycetes Actinomycetota None Bacteria

Properties Information

Molecule Weight: 570.3850000000002

TPSA？: 149.52999999999997

MolLogP？: 3.820700000000004

Number of H-Donors: 5

Number of H-Acceptors: 7

RingCount: 7

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus cereus Bacillus cereus Antimicrobial activity nan None 10.1021/jm980396d
Bacillus cereus Bacillus cereus Inhibition zone 9.0 mM 10.1021/jm970843+
Bacillus cereus Bacillus cereus MIC 6.25 ug.mL-1 10.1021/jm9603779
Bacillus cereus Bacillus cereus MIC 10900.0 nM 10.1021/jm9702084
Bacillus cereus Bacillus cereus MIC 10900.0 nM 10.1021/jm970843+
Bacillus cereus Bacillus cereus MIC 10900.0 nM 10.1021/jm980396d
Bacillus cereus Bacillus cereus MIC 10900.0 nM 10.1021/jm980702n
Homo sapiens A549 IC50 300.0 nM 10.1021/jm011045t
Homo sapiens cAMP-dependent protein kinase (PKA) IC50 nan nM 10.1016/S0960-894X(00)80167-5
Homo sapiens CEM-SS CC50 1050.0 nM 10.1021/jm970843+
Homo sapiens CEM-SS CC50 1050.0 nM 10.1021/jm980396d
Homo sapiens CEM-SS CC50 1050.0 nM 10.1021/jm980702n
Homo sapiens CEM-SS IC50 520.0 nM 10.1021/jm970843+
Homo sapiens CEM-SS IC50 520.0 nM 10.1021/jm980396d
Homo sapiens CEM-SS IC50 520.0 nM 10.1021/jm980702n
Homo sapiens CEM-SS Selectivity index 2.0 SI 10.1021/jm980702n
Homo sapiens DNA topoisomerase I MIC 1.0 ug.mL-1 10.1021/jm9603779
Homo sapiens DNA topoisomerase I MIC 1750.0 nM 10.1021/jm9702084
Homo sapiens DNA topoisomerase I MIC 1750.0 nM 10.1021/jm970843+
Homo sapiens DNA topoisomerase I MIC 1750.0 nM 10.1021/jm980396d
Homo sapiens DNA topoisomerase I MIC 1750.0 nM 10.1021/jm980702n
Homo sapiens DNA topoisomerase II MIC 17500.0 nM 10.1021/jm9702084
Homo sapiens DNA topoisomerase II beta MIC 10.0 ug.mL-1 10.1021/jm9603779
Homo sapiens DU-145 IC50 nan nM 10.1021/jm049213f
Homo sapiens DU-145 IC50 nan None 10.1016/j.bmcl.2010.05.088
Homo sapiens Dual-specificity tyrosine-phosphorylation regulated kinase 1A IC50 19.0 nM 10.1016/j.ejmech.2018.08.093
Homo sapiens HT-29 IC50 300.0 nM 10.1021/jm011045t
Homo sapiens HT-29 IC50 300.0 nM 10.1021/jm049213f
Homo sapiens K562 IC50 200.0 nM 10.1021/jm011045t
Homo sapiens K562 IC50 4000.0 nM 10.1016/j.bmc.2008.07.017
Homo sapiens K562 IC50 6000.0 nM 10.1021/jm0493764
Homo sapiens Protein kinase C alpha IC50 100000.0 nM 10.1021/jm9603779
Homo sapiens Protein kinase C alpha IC50 100000.0 nM 10.1021/jm9702084
Homo sapiens Protein kinase C (PKC) IC50 100000.0 nM 10.1016/S0960-894X(00)80167-5
Homo sapiens Protein kinase C (PKC) IC50 175000.0 nM 10.1021/jm980396d
Homo sapiens SW-620 IC50 4000.0 nM 10.1016/j.bmc.2008.07.017
Homo sapiens SW-620 IC50 4000.0 nM 10.1021/jm0493764
Mus musculus B16 IC50 480.0 nM 10.1021/jm9603779
Mus musculus B16 IC50 480.0 nM 10.1021/jm9702084
Mus musculus B16 IC50 480.0 nM 10.1021/jm970843+
Mus musculus L1210 Activity 69.0 % 10.1021/jm011045t
Mus musculus L1210 IC50 100.0 nM 10.1021/jm011045t
Mus musculus L1210 IC50 140.0 nM 10.1016/j.bmcl.2010.05.088
Mus musculus L1210 IC50 140.0 nM 10.1021/jm049213f
Mus musculus Mus musculus Mean survival in days 15.0 None 10.1021/jm9603779
Mus musculus Mus musculus Mean survival in days 16.5 None 10.1021/jm9603779
Mus musculus Mus musculus Mean survival in days 18.0 None 10.1021/jm9603779
Mus musculus Mus musculus Mean survival in days 26.0 None 10.1021/jm9603779
Mus musculus Mus musculus Mean survival in days 27.5 None 10.1021/jm9603779
Mus musculus Mus musculus Mean survival in days 30.5 None 10.1021/jm9603779
Mus musculus Mus musculus T/C x100 106.0 None 10.1021/jm9603779
Mus musculus Mus musculus T/C x100 112.0 None 10.1021/jm9603779
Mus musculus Mus musculus T/C x100 124.0 None 10.1021/jm9603779
Mus musculus Mus musculus T/C x100 136.0 None 10.1021/jm9603779
Mus musculus Mus musculus T/C x100 150.0 None 10.1021/jm9603779
Mus musculus Mus musculus T/C x100 164.0 None 10.1021/jm9603779
Mus musculus P388 Activity 0.81 None 10.1021/jm980702n
Mus musculus P388 Activity 1.29 None 10.1021/jm980702n
Mus musculus P388 Fraction change 29.0 % 10.1021/jm980702n
Mus musculus P388 IC50 300.0 nM 10.1021/jm9603779
Mus musculus P388 IC50 500.0 nM 10.1021/jm9702084
Mus musculus P388 IC50 1220.0 nM 10.1021/jm970843+
Mus musculus P388 IC50 1220.0 nM 10.1021/jm980396d
Mus musculus P388 IC50 1220.0 nM 10.1021/jm980702n
Mus musculus P388 IC50 10500.0 nM 10.1021/jm980396d
Mus musculus P388 Ratio 8.5 None 10.1021/jm980702n
Mus musculus P388CPT5 IC50 10500.0 nM 10.1021/jm970843+
Mus musculus P388CPT5 IC50 10500.0 nM 10.1021/jm980702n
Streptomyces chartreusis Streptomyces chartreusis Antimicrobial activity nan None 10.1021/jm980396d
Streptomyces chartreusis Streptomyces chartreusis Inhibition zone 9.0 mM 10.1021/jm970843+
None Nucleic Acid DeltaTm 0.0 None 10.1021/jm980396d
None Unchecked IC50 100000.0 nM 10.1021/jm9603779
None Unchecked Resistance index 8.6 None 10.1021/jm980396d
None Unchecked Selectivity index 2.0 None 10.1021/jm970843+
None Unchecked Selectivity index 2.0 None 10.1021/jm980396d

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT012661 C[33S].O=C1NC(=O)c2c1c1c3cccc(Cl)c3[nH]c1c1c2c2cccc(Cl)c2n1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O>>CO[C@H]1[C@H](O)[C@@H](O)[C@H](n2c3c(Cl)cccc3c3c4c(c5c6cccc(Cl)c6[nH]c5c32)C(=O)NC4=O)O[C@@H]1CO None
AKRT014731 C[SAH].O=C1NC(=O)c2c1c1c3cccc(Cl)c3[nH]c1c1c2c2cccc(Cl)c2n1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O>>CO[C@@H]1[C@@H](CO)O[C@@H](n2c3c(Cl)cccc3c3c4c(c5c6cccc(Cl)c6[nH]c5c32)C(=O)NC4=O)[C@H](O)[C@H]1O RXN-10847