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Echinomycin

AlkaPlorer ID: AK000271

Synonym: None

IUPAC Name: N-[(1R,4S,7R,11S,14R,17S,20R,24S,27S)-2,4,12,15,17,25-hexamethyl-27-methylsulfanyl-3,6,10,13,16,19,23,26-octaoxo-11,24-di(propan-2-yl)-20-(quinoxaline-2-carbonylamino)-9,22-dioxa-28-thia-2,5,12,15,18,25-hexazabicyclo[12.12.3]nonacosan-7-yl]quinoxaline-2-carboxamide

Structure

SMILES: CS[C@H]1SC[C@H]2C(=O)N(C)[C@@H](C(C)C)C(=O)OC[C@@H](N=C(O)C3=CN=C4C=CC=CC4=N3)C(O)=N[C@@H](C)C(=O)N(C)[C@@H]1C(=O)N(C)[C@@H](C(C)C)C(=O)OC[C@@H](N=C(O)C1=CN=C3C=CC=CC3=N1)C(O)=N[C@@H](C)C(=O)N2C

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InChI: InChI=1S/C51H64N12O12S2/c1-25(2)38-49(72)74-22-36(59-42(65)34-21-53-30-17-13-15-19-32(30)57-34)44(67)55-28(6)46(69)63(10)40-48(71)62(9)39(26(3)4)50(73)75-23-35(58-41(64)33-20-52-29-16-12-14-18-31(29)56-33)43(66)54-27(5)45(68)60(7)37(47(70)61(38)8)24-77-51(40)76-11/h12-21,25-28,35-40,51H,22-24H2,1-11H3,(H,54,66)(H,55,67)(H,58,64)(H,59,65)/t27-,28-,35+,36+,37-,38-,39-,40+,51-/m0/s1

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InChIKey: AUJXLBOHYWTPFV-VLNMHYLBSA-N

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Reference

PubChem CID: 44582409

NPASS: NPC214827

Source

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

Properties Information

Molecule Weight: 1101.2789999999995

TPSA？: 315.76

MolLogP？: 3.4655000000000085

Number of H-Donors: 4

Number of H-Acceptors: 18

RingCount: 6

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus anthracis Bacillus anthracis MIC 1.0 ug.mL-1 10.1021/np030397v
Bos taurus Calf thymus DNA Activity nan None 10.1016/j.bmc.2010.12.009
Bos taurus Calf thymus DNA Tm 79.0 degrees C 10.1016/j.bmc.2010.12.009
Electrophorus electricus Acetylcholinesterase Inhibition -10.15 % 10.1016/j.bmc.2012.09.040
Enterococcus faecalis Enterococcus faecalis Activity nan None 10.1016/j.bmcl.2009.01.010
Enterococcus faecalis Enterococcus faecalis log10CFU/ml -1.42 None 10.1016/j.bmcl.2009.01.010
Enterococcus faecalis Enterococcus faecalis log10CFU/ml 0.04 None 10.1016/j.bmcl.2009.01.010
Enterococcus faecalis Enterococcus faecalis MBC 0.11 uM 10.1016/j.bmcl.2009.01.010
Enterococcus faecalis Enterococcus faecalis MBIC 0.22 uM 10.1016/j.bmcl.2009.01.010
Enterococcus faecalis Enterococcus faecalis MIC 10.0 nM 10.1016/j.bmcl.2009.01.010
Equus caballus Cholinesterase Inhibition -7.37 % 10.1016/j.bmc.2012.09.040
Homo sapiens Beta-hexosaminidase subunit alpha Activity nan None 10.1021/ml400323x
Homo sapiens BeWo IC50 1.0 ug.mL-1 10.1016/j.bmcl.2003.09.086
Homo sapiens CCRF-CEM IC50 500.0 nM 10.1021/jm030253d
Homo sapiens HCT-116 IC50 3.0 nM 10.1016/j.bmcl.2009.01.010
Homo sapiens HT-29 Apoptotic cells 47.5 % 10.1016/j.bmcl.2003.09.086
Homo sapiens HT-29 IC50 2.2 ug.mL-1 10.1016/j.bmcl.2003.09.086
Homo sapiens Huh-7 CC50 10000.0 nM 10.1073/pnas.0802982105
Homo sapiens PANC-1 IC50 1.8 ug.mL-1 10.1016/j.bmcl.2003.09.086
Homo sapiens SNU-16 IC50 1.6e-07 ug.mL-1 10.1016/s0960-894x(98)00113-9
Mus musculus B16 IC50 6.5e-08 ug.mL-1 10.1016/s0960-894x(98)00113-9
Mus musculus B16 IC50 0.4 ug.mL-1 10.1016/j.bmcl.2003.09.086
Mus musculus B16 MST 21.0 day 10.1016/s0960-894x(98)00113-9
Mus musculus B16 MST 23.0 day 10.1016/s0960-894x(98)00113-9
Mus musculus B16 MST 24.0 day 10.1016/s0960-894x(98)00113-9
Mus musculus B16 MST 25.0 day 10.1016/s0960-894x(98)00113-9
Mus musculus P388 Activity 0.00147 ug ml-1 10.1021/np700738k
Mus musculus P388 IC50 4.3e-05 ug.mL-1 10.1016/s0960-894x(98)00113-9
Mus musculus P388 MST 26.0 day 10.1016/s0960-894x(98)00113-9
Mus musculus P388 MST 27.0 day 10.1016/s0960-894x(98)00113-9
Mus musculus P388 MST 31.0 day 10.1016/s0960-894x(98)00113-9
Mus musculus P388 MST 32.0 day 10.1016/s0960-894x(98)00113-9
Mus musculus P388 MST 33.0 day 10.1016/s0960-894x(98)00113-9
Plasmodium falciparum Plasmodium falciparum EC50 73.7 nM 10.1073/pnas.0802982105
Plasmodium falciparum Plasmodium falciparum EC50 524.0 nM 10.1073/pnas.0802982105
Plasmodium falciparum Plasmodium falciparum LD50 7.0 ng/ml 10.1021/np030397v
Staphylococcus aureus Staphylococcus aureus Activity nan None 10.1016/j.bmcl.2009.01.010
Staphylococcus aureus Staphylococcus aureus log10CFU/ml -2.39 None 10.1016/j.bmcl.2009.01.010
Staphylococcus aureus Staphylococcus aureus log10CFU/ml -1.79 None 10.1016/j.bmcl.2009.01.010
Staphylococcus aureus Staphylococcus aureus log10CFU/ml -1.54 None 10.1016/j.bmcl.2009.01.010
Staphylococcus aureus Staphylococcus aureus log10CFU/ml -1.23 None 10.1016/j.bmcl.2009.01.010
Staphylococcus aureus Staphylococcus aureus log10CFU/ml 0.423 None 10.1016/j.bmcl.2009.01.010
Staphylococcus aureus Staphylococcus aureus log10CFU/ml 0.61 None 10.1016/j.bmcl.2009.01.010
Staphylococcus aureus Staphylococcus aureus MBC 0.45 uM 10.1016/j.bmcl.2009.01.010
Staphylococcus aureus Staphylococcus aureus MBC 0.91 uM 10.1016/j.bmcl.2009.01.010
Staphylococcus aureus Staphylococcus aureus MBIC 0.03 uM 10.1016/j.bmcl.2009.01.010
Staphylococcus aureus Staphylococcus aureus MBIC 0.22 uM 10.1016/j.bmcl.2009.01.010
Staphylococcus aureus Staphylococcus aureus MBIC 4.0 uM 10.1016/j.bmcl.2009.01.010
Staphylococcus aureus Staphylococcus aureus MIC 10.0 nM 10.1016/j.bmcl.2009.01.010
Staphylococcus aureus Staphylococcus aureus MIC 30.0 nM 10.1016/j.bmcl.2009.01.010
None NON-PROTEIN TARGET Hepatotoxicity (acute) 4.8 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (animal toxicity known) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (benign tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (granulomatous hepatitis) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (mechanism) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 8.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 29.4 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (time to onset) nan None 10.1016/s0399-8320(04)95062-2
None Nucleic Acid EC50 1.2 nM 10.1016/j.ejmech.2012.01.033
None Unchecked Activity nan None 10.1021/ml400323x
None Unchecked Hepatotoxicity (acute) 4.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (association with vascular disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (choleostasis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (chronic liver disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cirrhosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (comment) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cytolytic) 3.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (malignant tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (severe hepatitis) 1.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (steatosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (successful reintroduction) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked IFI 34.62 % 10.1073/pnas.0802982105

Metabolism Information