BIRD-PRD_000488: TRIOSTIN A

基本情報

• 登録情報: データベース: 生物学的重要分子辞書 (BIRD) / ID: PRD_000488
• 状態: 状態: REF ONLY
• 名称: TRIOSTIN A

BIRD information

• タイプ: Cyclic depsipeptide / 抗がん剤

詳細

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

• ダウンロード: Molecular definition / Chemical definition / Family definition

別称

• B100928K382 (PubChem)
• NCI60_001953 (PubChem)
• NSC 244425 (SciFinder)
• NSC2444425 (PubChem)
• TRIOSTIN (PDB)
• Triostin A (SciFinder, PubChem, ChemSpider)
• Triostins (Merck)
• dilactone (Beilstein)

Annotation

• 分子機能: 抗腫瘍剤 / 情報源: NovelAntibiotics
• 分子機能: antibacterial activity / 情報源: PubChem

由来

• Streptomyces triostinicus, Norine: NOR01129
• Streptomycineae (バクテリア), :

External info

• Beilstein: 604469
• Merck: 14:9733
• NovelAntibiotics: 140098
• ChemSpider: 65433
• PubChem: 316447
• CAS: 13758-27-5
• [KEGG_Compound_ID] KEGG: C15721
• [MESH_Unique_ID] MESH: C031945
• WikiPedia
• Nature

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

組成

組成式: C₅₀H₆₂N₁₂O₁₂S₂ / 化学式量: 1087.23

• その他: タイプ: peptide-like

履歴

• 外部リンク: UniChem / ChemSpider / Wikipedia search / Google search

詳細

SMILES

• ACDLabs 12.01: O=C3N(C)C(C(=O)OCC(NC(=O)c1nc2c(nc1)cccc2)C(=O)NC(C(=O)N(C)C4C(=O)N(C)C(C(=O)OCC(C(=O)NC(C(=O)N(C3CSSC4)C)C)NC(=O)c5nc6c(nc5)cccc6)C(C)C)C)C(C)C
• CACTVS 3.370: CC(C)[CH]1N(C)C(=O)[CH]2CSSC[CH](N(C)C(=O)[CH](C)NC(=O)[CH](COC1=O)NC(=O)c3cnc4ccccc4n3)C(=O)N(C)[CH](C(C)C)C(=O)OC[CH](NC(=O)c5cnc6ccccc6n5)C(=O)N[CH](C)C(=O)N2C
• OpenEye OEToolkits 1.7.6: CC1C(=O)N(C2CSSCC(C(=O)N(C(C(=O)OCC(C(=O)N1)NC(=O)c3cnc4ccccc4n3)C(C)C)C)N(C(=O)C(NC(=O)C(COC(=O)C(N(C2=O)C)C(C)C)NC(=O)c5cnc6ccccc6n5)C)C)C

SMILES CANONICAL

• CACTVS 3.370: CC(C)[C@@H]1N(C)C(=O)[C@@H]2CSSC[C@H](N(C)C(=O)[C@H](C)NC(=O)[C@@H](COC1=O)NC(=O)c3cnc4ccccc4n3)C(=O)N(C)[C@@H](C(C)C)C(=O)OC[C@@H](NC(=O)c5cnc6ccccc6n5)C(=O)N[C@@H](C)C(=O)N2C
• OpenEye OEToolkits 1.7.6: C[C@H]1C(=O)N([C@H]2CSSC[C@@H](C(=O)N([C@H](C(=O)OC[C@H](C(=O)N1)NC(=O)c3cnc4ccccc4n3)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)c5cnc6ccccc6n5)C)C)C

InChI

• InChI 1.03: InChI=1S/C50H62N12O12S2/c1-25(2)39-49(71)73-21-35(57-41(63)33-19-51-29-15-11-13-17-31(29)55-33)43(65)53-28(6)46(68)60(8)38-24-76-75-23-37(47(69)61(39)9)59(7)45(67)27(5)54-44(66)36(22-74-50(72)40(26(3)4)62(10)48(38)70)58-42(64)34-20-52-30-16-12-14-18-32(30)56-34/h11-20,25-28,35-40H,21-24H2,1-10H3,(H,53,65)(H,54,66)(H,57,63)(H,58,64)/t27-,28-,35+,36+,37-,38-,39-,40-/m0/s1

InChIKey

• InChI 1.03: GULVULFEAVZHHC-IITWSDOJSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: N,N-[(1R,4S,7R,11S,14R,17S,20R,24S)-2,4,12,15,17,25-hexamethyl-3,6,10,13,16,19,23,26-octaoxo-11,24-di(propan-2-yl)-9,22-dioxa-28,29-dithia-2,5,12,15,18,25-hexaazabicyclo[12.12.4]triacontane-7,20-diyl]diquinoxaline-2-carboxamide
• OpenEye OEToolkits 1.7.6: N-[(1R,4S,7R,11S,14R,17S,20R,24S)-2,4,12,15,17,25-hexamethyl-3,6,10,13,16,19,23,26-octakis(oxidanylidene)-11,24-di(propan-2-yl)-20-(quinoxalin-2-ylcarbonylamino)-9,22-dioxa-28,29-dithia-2,5,12,15,18,25-hexazabicyclo[12.12.4]triacontan-7-yl]quinoxaline-2-carboxamide

PDBエントリ

全6件を表示しています

PDB-185d:
SEQUENCE SPECIFICITY OF QUINOXALINE ANTIBIOTICS. 1. SOLUTION STRUCTURE OF A 1:1 COMPLEX BETWEEN TRIOSTIN A AND [D(GACGTC)]2 AND COMPARISON WITH THE SOLUTION STRUCTURE OF THE [N-MECYS3, N-MECYS7]TANDEM-[D(GATATC)]2 COMPLEX

PDB-185d:
SEQUENCE SPECIFICITY OF QUINOXALINE ANTIBIOTICS. 1. SOLUTION STRUCTURE OF A 1:1 COMPLEX BETWEEN TRIOSTIN A AND [D(GACGTC)]2 AND COMPARISON WITH THE SOLUTION STRUCTURE OF THE [N-MECYS3, N-MECYS7]TANDEM-[D(GATATC)]2 COMPLEX

PDB-1vs2:
Interactions of quinoxaline antibiotic and DNA: the molecular structure of a TRIOSTIN A-D(GCGTACGC) complex

PDB-1vs2:
Interactions of quinoxaline antibiotic and DNA: the molecular structure of a TRIOSTIN A-D(GCGTACGC) complex

PDB-1vtg:
THE MOLECULAR STRUCTURE OF A DNA-TRIOSTIN A COMPLEX

PDB-1vtg:
THE MOLECULAR STRUCTURE OF A DNA-TRIOSTIN A COMPLEX