Also known as: Echinomycin, Tg824j6rqt, 512-64-1, S-426-s (lepetit), Nsc-526417, N,n'-((1r,4s,7r,11s,14r,17s,20r,24s)-11,24-diisopropyl-2,4,12,15,17,25-hexamethyl-27-(methylthio)-3,6,10,13,16,19,23,26-octaoxo-9,22-dioxa-28-thia-2,5,12,15,18,25-hexaazabicyclo[12.12.3]nonacosane-7,20-diyl)bis(quinoxaline-2-carboxamide)

Molecular Formula

C₅₁H₆₄N₁₂O₁₂S₂

Molecular Weight

1101.3 g/mol

InChI Key

AUJXLBOHYWTPFV-VITLIGDRSA-N

FDA UNII

TG824J6RQT

A cytotoxic polypeptide quinoxaline antibiotic isolated from Streptomyces echinatus that binds to DNA and inhibits RNA synthesis.

1 2D Structure

2D Structure

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[(1R,4S,7R,11S,14R,17S,20R,24S)-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

2.1.2 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

2.1.3 InChI Key

AUJXLBOHYWTPFV-VITLIGDRSA-N

2.1.4 Canonical SMILES

CC1C(=O)N(C2CSC(C(C(=O)N(C(C(=O)OCC(C(=O)N1)NC(=O)C3=NC4=CC=CC=C4N=C3)C(C)C)C)N(C(=O)C(NC(=O)C(COC(=O)C(N(C2=O)C)C(C)C)NC(=O)C5=NC6=CC=CC=C6N=C5)C)C)SC)C

2.1.5 Isomeric SMILES

C[C@H]1C(=O)N([C@H]2CSC([C@@H](C(=O)N([C@H](C(=O)OC[C@H](C(=O)N1)NC(=O)C3=NC4=CC=CC=C4N=C3)C(C)C)C)N(C(=O)[C@@H](NC(=O)[C@@H](COC(=O)[C@@H](N(C2=O)C)C(C)C)NC(=O)C5=NC6=CC=CC=C6N=C5)C)C)SC)C

2.2 Other Identifiers

2.2.1 UNII

TG824J6RQT

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Echinomycin

2. Nsc 526417

3. Nsc-526417

4. Nsc526417

2.3.2 Depositor-Supplied Synonyms

1. Echinomycin

2. Tg824j6rqt

3. 512-64-1

4. S-426-s (lepetit)

5. Nsc-526417

6. N,n'-((1r,4s,7r,11s,14r,17s,20r,24s)-11,24-diisopropyl-2,4,12,15,17,25-hexamethyl-27-(methylthio)-3,6,10,13,16,19,23,26-octaoxo-9,22-dioxa-28-thia-2,5,12,15,18,25-hexaazabicyclo[12.12.3]nonacosane-7,20-diyl)bis(quinoxaline-2-carboxamide)

7. Unii-tg824j6rqt

8. Nsc-13502

9. Sk 302b

10. Nsc 526417

11. Brn 0078671

12. Echinomycin [mi]

13. Antibiotic A-654i

14. 4-27-00-09726 (beilstein Handbook Reference)

15. Chembl503868

16. Schembl13464701

17. Sk-302b

18. Db15582

19. Stereoisomer Of N,n'-(2,4,12,15,17,25-hexamethyl-11,24-bis(1-methylethyl)-27-(methylthio)-3,6,10,13,16,19,23,26-octaoxo-9,22-dioxa-28-thia-2,5,12,15,18,25-hexaazabicyclo(12.12.3)nonacosane-7,20-diyl)bis(2-quinoxalinecarboxamide)

20. Hy-106101

21. Cs-0024860

22. L-valine, N-(2-quinoxalinylcarbonyl)-o-(n-(2-quinoxalinylcarbonyl)-d-seryl-l-alanyl-3-mercapto-n,s-dimethylcysteinyl-n-methyl-l-valyl)-d-seryl-l-alanyl-n-methylcysteinyl-n-methyl-, (8->1)-lactone, Cyclic (3->7)-thioether

23. N-(2-quinoxalinylcarbonyl)-o-(n-(2-quinoxalinylcarbonyl)-d-seryl-l-alanyl-3-mercapto-n,s-dimethylcysteinyl-n-methyl-l-valyl)-d-seryl-l-alanyl-n-methylcysteinyl-n-methyl L-valine (8->1)-lactone Cyclic (3->7)-thioester

2.4 Create Date

2006-06-21

3 Chemical and Physical Properties

Molecular Formula	C₅₁H₆₄N₁₂O₁₂S₂
Molecular Weight	1101.3 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	18
Rotatable Bond Count	7
Exact Mass	1100.42080787 g/mol
Monoisotopic Mass	1100.42080787 g/mol
Topological Polar Surface Area	352 Å²
Heavy Atom Count	77
Formal Charge	0
Complexity	2200
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

Nucleic Acid Synthesis Inhibitors

Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)

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Echinomycin

Echinomycin

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