BIRD-PRD_000492: uk63052

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000492
• Status: Status: REF ONLY
• Name: uk63052

BIRD information

• Type: Cyclic depsipeptide / Antibiotic

Details

• QUINOMYCIN UK63052 IS A BICYCLIC OCTADEPSIPEPTIDE, A MEMBER OF THE QUINOXALINE CLASS OF ANTIBIOTICS. HERE, QUINOMYCIN IS REPRESENTED BY GROUPING TOGETHER THE SEQUENCE (SEQRES) AND THE TWO LIGANDS (HET) HQU
• QUINOMYCIN UK63052 IS A BICYCLIC OCTADEPSIPEPTIDE. BICYCLIZATION IS ACHIEVED BY LINKING THE N- AND THE C- TERMINI, AND A THIOACETAL BOND BETWEEN RESIDUES 3 AND 7. THE TWO HYDROXYQUINOXALINE CHROMOPHORES ARE LINKED TO THE D-SERINE RESIDUES, RESIDUES 1 AND 5.

• Downloads: Molecular definition / Chemical definition / Family definition

Synonyms

• 2-Quinoxalinecarboxmide, 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]nonacosan e-7,20-diyl]bis- (ChemBank)
• AIDS 073381 (PubChem)
• Antibiotic UK 63052 (ChemSpider)
• Antibiotic UK 63052 (9CI) (SciFinder)
• Antibiotics UK 63052 (PubChem)
• Echinomycin (ChemBank)
• Echinomycin A (ChemBank)
• Levomycin (ChemBank)
• NCI60_009979 (PubChem)
• NSC 630678 (PubChem)
• Neuro_000276 (PubChem)
• QUINOMYCIN (PDB)
• Quinomycin A (ChemBank)
• S-426-S (Lepetit) (ChemBank)
• SW 163G (SciFinder)
• SW-163G (Beilstein)
• Streptomyces antibiotic (PubChem)
• Streptomyces antibiotic UK-63052 (PubChem, ChemSpider)
• UK 63052 (SciFinder, PubChem)

Source

• Streptomyces braegensis, N617-29, :

External info

• Beilstein: 11250492
• PubChem: 131388
• CAS: 120763-23-7
• CAS: 120832-02-2
• [MESH_Unique_ID] MESH: C059030

Family

quinoxaline

TRIOSTIN A / Echinomycin / uk63052

Related structures

• Triostin A isoamyl acetate solvate, seqres C5 ALA-CYS*!,CYS*!-VAL*,SER*- C5 CYS*!-VAL*,SER*-ALA-CYS*!, / CCDC: CULVUA / PubMed / Reference
• Triostin A isoamyl acetate solvate, seqres C5 ALA-CYS*!,CYS*!-VAL*,SER*- C5 CYS*!-VAL*,SER*-ALA-CYS*!, / CCDC: CULVUA10 / Reference
• Triostin C chloroform solvate hydrate, seqres C5 ALA-CYS*!,CYS*!-LEU*,SER*- C5 CYS*!-LEU*,SER*-ALA-CYS*!, / CCDC: ZILGOQ / Reference
• Triostin A hydrochloride dimethylformamide solvate, seqres C5 ALA-CYS*!,CYS*!-VAL*,SER*- C5 CYS*!-VAL*,SER*-ALA-CYS*!, / CCDC: ZILHAD / Reference
• Des-N-tetramethyltriostin A dodecahydrate, Tandem dodecahydrate / CCDC: TANDEM30 / PubMed / Reference
• Des-N-tetramethyltriostin A tetradecahydrate / CCDC: BICKON / PubMed / Reference
• des-N-Tetramethyl-triostin A dodecahydrate / CCDC: TANDEM20 / PubMed / Reference
• Echinomycin bis(quinoline) acetone solvate hydrate, Echinomycin 2QN, seqres C5 ALA-CYS*!,CYS*!-VAL*,SER*- C5 CYS*!-VAL*,SER*-ALA-CYS*!, / CCDC: ZILGIK / Reference
• Des-N-tetramethyl-triostin A dodecahydrate / CCDC: TANDEM / Reference
• Des-N-tetramethyl-triostin A methanol solvate hydrate / CCDC: TMTRST / Reference

Chemical information

Composition

Formula: C₅₆H₆₈N₁₀O₁₄S₂ / Formula weight: 1169.328

• Others: Type: peptide-like

History

• External links: UniChem / ChemSpider / Wikipedia search / Google search

Details

SMILES

• ACDLabs 12.01: O=C3N(C)C8(C(=O)OCC(NC(=O)c1nc2c(cc1O)cccc2)C(=O)NC(C(=O)N(C)C4C(=O)N(C)C7(C(=O)OCC(C(=O)NC(C(=O)N(C)C3C(SC(C)CC)SC4)C)NC(=O)c5nc6c(cc5O)cccc6)CC7C)C)CC8C
• CACTVS 3.370: CC[CH](C)S[CH]1SC[CH]2N(C)C(=O)[CH](C)NC(=O)[CH](COC(=O)[C]3(C[CH]3C)N(C)C(=O)[CH]1N(C)C(=O)[CH](C)NC(=O)[CH](COC(=O)[C]4(C[CH]4C)N(C)C2=O)NC(=O)c5nc6ccccc6cc5O)NC(=O)c7nc8ccccc8cc7O
• OpenEye OEToolkits 1.7.6: CCC(C)SC1C2C(=O)N(C3(CC3C)C(=O)OCC(C(=O)NC(C(=O)N(C(CS1)C(=O)N(C4(CC4C)C(=O)OCC(C(=O)NC(C(=O)N2C)C)NC(=O)c5c(cc6ccccc6n5)O)C)C)C)NC(=O)c7c(cc8ccccc8n7)O)C

SMILES CANONICAL

• CACTVS 3.370: CC[C@@H](C)S[C@H]1SC[C@@H]2N(C)C(=O)[C@H](C)NC(=O)[C@@H](COC(=O)[C@@]3(C[C@@H]3C)N(C)C(=O)[C@H]1N(C)C(=O)[C@H](C)NC(=O)[C@@H](COC(=O)[C@@]4(C[C@@H]4C)N(C)C2=O)NC(=O)c5nc6ccccc6cc5O)NC(=O)c7nc8ccccc8cc7O
• OpenEye OEToolkits 1.7.6: CC[C@@H](C)SC1[C@H]2C(=O)N([C@]3(C[C@@H]3C)C(=O)OC[C@H](C(=O)N[C@H](C(=O)N([C@@H](CS1)C(=O)N([C@]4(C[C@@H]4C)C(=O)OC[C@H](C(=O)N[C@H](C(=O)N2C)C)NC(=O)c5c(cc6ccccc6n5)O)C)C)C)NC(=O)c7c(cc8ccccc8n7)O)C

InChI

• InChI 1.03: InChI=1S/C56H68N10O14S2/c1-11-29(4)82-52-43-51(76)66(10)56(23-28(56)3)54(78)80-25-36(61-46(71)41-39(67)20-32-16-12-14-18-34(32)59-41)44(69)57-30(5)48(73)63(7)38(26-81-52)50(75)65(9)55(22-27(55)2)53(77)79-24-37(45(70)58-31(6)49(74)64(43)8)62-47(72)42-40(68)21-33-17-13-15-19-35(33)60-42/h12-21,27-31,36-38,43,52,67-68H,11,22-26H2,1-10H3,(H,57,69)(H,58,70)(H,61,71)(H,62,72)/t27-,28-,29+,30-,31-,36+,37+,38-,43+,52+,55-,56-/m0/s1

InChIKey

• InChI 1.03: VABRZWDEEDQLRD-SXUOMVPDSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: N,N'-{(1S,1'R,2S,2''S,8'R,11'S,14'R,17'S,21'R,24'S,27'R)-27'-[(2R)-butan-2-ylsulfanyl]-2,2'',3',11',13',16',24',26'-octamethyl-2',5',9',12',15',18',22',25'-octaoxo-6',19'-dioxa-28'-thia-3',10',13',16',23',26'-hexaazadispiro[cyclopropane-1,4'-bicyclo[12.12.3]nonacosane-17',1''-cyclopropane]-8',21'-diyl}bis(3-hydroxyquinoline-2-carboxamide) #

PDB entries

Showing all 2 items

PDB-193d:
SOLUTION STRUCTURE OF A QUINOMYCIN BISINTERCALATOR-DNA COMPLEX

PDB-193d:
SOLUTION STRUCTURE OF A QUINOMYCIN BISINTERCALATOR-DNA COMPLEX