BIRD-PRD_000203: Chloroorienticin 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_000203
• 状態: 状態: REF ONLY
• 名称: Chloroorienticin A

BIRD information

• タイプ: 糖ペプチド / 抗生剤

詳細

• CHLOROORIENTICIN A IS A TRICYCLIC GLYCOPEPTIDE, A MEMBER OF THE VANCOMYCIN FAMILY. THE SCAFFOLD IS A HEPTAPEPTIDE WITH THE CONFIGURATION D-D-L-D-D-L-L. IT IS FURTHER GLYCOSYLATED BY ONE DISACCHARIDE AND ONE MONOSACCHARIDE HERE, CHLOROORIENTICIN A IS REPRESENTED BY GROUPING TOGETHER THE SEQUENCE (SEQRES) AND THE THREE LIGANDS (HET) BGC AND TWO RER.
• CHLOROORIENTICIN A IS A TRICYCLIC GLYCOPEPTIDE, GLYCOSYLATED BY ONE DISACCHARIDE ON RESIDUE 4 AND ONE MONOSACCHARIDE ON RESIDUE 6.

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

別称

• (2S,3R,4S,6S)-6-{[(2S,3R,4S,5S,6R)-2-{[(1S,2R,18R,19R,22S,25R,28R,40S)-22-(2-amino-2-oxoethyl)-2-{[(2R,4S,5R,6S)-4-ammonio-5-hydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-40-carboxy-5,15-dichloro-18,32,35,37-tetrahydroxy-19-{[(2R)-4-methyl-2-(methylammonio)pentanoyl]amino}-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo [26.14.2.2~3,6~.2~14,17~.1~8,12~.1~29,33~.0~10,25~.0~34,39~]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34,36,38,46,49-pentadecaen-48-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-3-hydroxy-2,4-dimethyltetrahydro-2H-pyran-4-aminium (PDB)
• (4''R)-22-O-(3-Amino-2,3,6-trideoxy-3-C-methyl-alpha-L-arabino-hexopyranosyl)vancomycin (PubChem)
• 4-EPI-VANCOSAMINYL DERIVATIVE OF VANCOMYCIN (PDB)
• 8-82846A (PubChem)
• A 82846B (PubChem)
• A-82846B (PubChem)
• A83846B (PubChem)
• Antibiotic A 82846B (PubChem)
• Antibiotic PA 45052A (PubChem)
• Chloroeremomycin (PubChem, KEGG)
• Chloroorienticin A (PubChem, KEGG)
• LY 264826 (PubChem)
• LY-264826 (PubChem)
• PA 45052A (PubChem)
• Vancomycin, 22-O-(3-amino-2,3,6-trideoxy-3-C-methyl-alpha-L-arabino-hexopyranosyl)-, (4''R)- (PubChem)
• antibiotic A82846B (PubChem)

Annotation

• 分子機能: Glycopeptide antibiotic / 情報源: PubMed: 7626632

由来

• Amycolatopsis orientalis (previously designated Norcardia orientalis and Streptomyces orientalis), :
• AMYCOLATOPSIS ORIENTALIS (バクテリア), Norine: NOR00681

External info

• ChemIDplus: 118395736
• MESH: C057893
• ChemSpider: 143874
• ChemSpider: 2641045
• ChemSpider: 391744
• ChemSpider: 393335
• PubChem: 164062
• PubChem: 23451523
• PubChem: 3396476
• PubChem: 443579
• PubChem: 445806
• CAS: 118395-73-6
• [KEGG_Compound_ID] KEGG: C12014
• chemicalland21.com: ANTIBIOTICS.htm
• ChemDrug
• LookChem
• ctdbase.org
• ASM
• SGMJOURNALS
• PNAS
• PNAS
• Medscape
• Prous.com
• RSC
• PMC
• ChemicalBook
• ACS

Family

glycopeptide antibiotic

Chloroorienticin A / Vancomycin / DESVANCOSAMINYL VANCOMYCIN / VANCOMYCIN AGLYCON / Decaplanin / Teicoplanin A2-2 beta-D-Glucopyranuronic acid / Teicoplanin Aglycone / BIRD: PRD_000211 / Balhimycin / Deglucobalhimycin / MonodeChloro- Teicoplanin A2-2 / desulfo-A47934 / teicoplanin

Related structures

• carboxy-decarboxamido-vancomycin hydrate / CCDC: VANCMN / Reference
• Vancomycin-N-acetyl-D-alanine-D-alanine / CCDC: COGQIY / Reference
• Vancomycin M43A hydrate / CCDC: VADNET / Reference
• Vancomycin dichloride acetic acid hydrate / CCDC: TUCMEJ / Reference
• Vancomycin acetate dichloride hydrate / CCDC: TUCMEJ01 / PubMed / Reference
• tetrakis(balhimycin) dicitrate triacetate 2-methyl-2,4-pentanediol hydrate, seqres A7 LEU*-TYR*-ASN-GLY*-GLY*-TYR*-GLY* / CCDC: NOSVOG / Reference
• ureido-balhimycin hydrate / CCDC: HICHUW / Reference
• Sodium N-acetyl-D-alanyl-D-alanine vancomycin 2-(4-morpholino)ethylsulfonate polyethylene glycol decahydrate, seqres C6 SER*!-ASN-GLY*-GLY*-SER*!,UND, A2 LEU-SER*!, A2 SER*!-GLY*, A2 ALA*-ALA / CCDC: LOKFOH / PubMed / Reference
• hexakis(Vancomycin) hexakis(N-acetyl-D-alanyl-D-alanine) sulfate dioxane solvate hydrate, seqres C6 SER*!-ASN-GLY*-GLY*-SER*!,UND, A2 LEU-SER*!, A2 SER*!-GLY*, A2 ALA*-ALA / CCDC: LOKFUN / PubMed / Reference
• hexakis(Vancomycin) hexakis(N,N'-diacetyllysyl-D-alanyl-D-lactate) hydrate, seqres C6 SER*!-ASN-GLY*-GLY*-SER*!,UND, A2 LEU-SER*!, A2 SER*!-GLY*, A2 LYS*-ALA* / CCDC: LOKGAU / PubMed / Reference
• aqua-vancomycin-copper(ii) hemikis(sodium chloride) hydrate / CCDC: NIXMAJ / PubMed / Reference
• bis(vancomycinium) monohydrogen phosphate sodium trichloride hydrate / CCDC: WUPWAG / Reference
• bis(vancomycinium) N-acetyl-D-alaninate sodium trichloride tritriacontahydrate / CCDC: WUPWEK / Reference

Chemical information

組成

組成式: C₇₃H₈₈Cl₂N₁₀O₂₆ / 化学式量: 1592.437

• 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=C3NC(C(=O)O)c1cc(O)cc(O)c1c2c(O)ccc(c2)C%10C(=O)NC3C(OC4OC(C(O)C(N)(C4)C)C)c%11ccc(Oc9c(OC6OC(CO)C(O)C(O)C6OC5OC(C)C(O)C(N)(C)C5)c8Oc7ccc(cc7Cl)C(O)C(NC(=O)C(NC)CC(C)C)C(=O)NC(C(=O)NC(c(c8)c9)C(=O)N%10)CC(=O)N)c(Cl)c%11
• CACTVS 3.370: CN[CH](CC(C)C)C(=O)N[CH]1[CH](O)c2ccc(Oc3cc4cc(Oc5ccc(cc5Cl)[CH](O[CH]6C[C](C)(N)[CH](O)[CH](C)O6)[CH]7NC(=O)[CH](NC(=O)[CH]4NC(=O)[CH](CC(N)=O)NC1=O)c8ccc(O)c(c8)c9c(O)cc(O)cc9[CH](NC7=O)C(O)=O)c3O[CH]%10O[CH](CO)[CH](O)[CH](O)[CH]%10O[CH]%11C[C](C)(N)[CH](O)[CH](C)O%11)c(Cl)c2
• OpenEye OEToolkits 1.7.6: CC1C(C(CC(O1)OC2c3ccc(c(c3)Cl)Oc4cc5cc(c4OC6C(C(C(C(O6)CO)O)O)OC7CC(C(C(O7)C)O)(C)N)Oc8ccc(cc8Cl)C(C(C(=O)NC(C(=O)NC5C(=O)NC9c1ccc(c(c1)-c1c(cc(cc1O)O)C(NC(=O)C2NC9=O)C(=O)O)O)CC(=O)N)NC(=O)C(CC(C)C)NC)O)(C)N)O

SMILES CANONICAL

• CACTVS 3.370: CN[C@H](CC(C)C)C(=O)N[C@@H]1[C@H](O)c2ccc(Oc3cc4cc(Oc5ccc(cc5Cl)[C@@H](O[C@H]6C[C@](C)(N)[C@@H](O)[C@H](C)O6)[C@@H]7NC(=O)[C@H](NC(=O)[C@@H]4NC(=O)[C@H](CC(N)=O)NC1=O)c8ccc(O)c(c8)c9c(O)cc(O)cc9[C@H](NC7=O)C(O)=O)c3O[C@@H]%10O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%10O[C@H]%11C[C@](C)(N)[C@@H](O)[C@H](C)O%11)c(Cl)c2
• OpenEye OEToolkits 1.7.6: C[C@H]1[C@@H]([C@@](C[C@@H](O1)O[C@@H]2c3ccc(c(c3)Cl)Oc4cc5cc(c4O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O[C@H]7C[C@]([C@H]([C@@H](O7)C)O)(C)N)Oc8ccc(cc8Cl)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]9c1ccc(c(c1)-c1c(cc(cc1O)O)[C@H](NC(=O)[C@H]2NC9=O)C(=O)O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)(C)N)O

InChI

• InChI 1.03: InChI=1S/C73H88Cl2N10O26/c1-26(2)14-38(79-7)64(96)84-54-56(91)30-9-12-42(36(74)16-30)106-44-18-32-19-45(60(44)111-71-61(58(93)57(92)46(25-86)108-71)110-49-24-73(6,78)63(95)28(4)105-49)107-43-13-10-31(17-37(43)75)59(109-48-23-72(5,77)62(94)27(3)104-48)55-69(101)83-53(70(102)103)35-20-33(87)21-41(89)50(35)34-15-29(8-11-40(34)88)51(66(98)85-55)82-67(99)52(32)81-65(97)39(22-47(76)90)80-68(54)100/h8-13,15-21,26-28,38-39,46,48-49,51-59,61-63,71,79,86-89,91-95H,14,22-25,77-78H2,1-7H3,(H2,76,90)(H,80,100)(H,81,97)(H,82,99)(H,83,101)(H,84,96)(H,85,98)(H,102,103)/t27-,28-,38+,39-,46+,48-,49-,51+,52+,53-,54+,55-,56+,57+,58-,59+,61+,62-,63-,71-,72-,73-/m0/s1

InChIKey

• InChI 1.03: XJHXLMVKYIVZTE-LOALFDMRSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: (1S,2R,18R,19R,22S,25R,28R,40S)-2-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-22-(2-amino-2-oxoethyl)-5,15-dichloro-18,32,35,37-tetrahydroxy-19-{[(2R)-4-methyl-2-(methylamino)pentanoyl]amino}-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2~3,6~.2~14,17~.1~8,12~.1~29,33~.0~10,25~.0~34,39~]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid (non-preferred name) #

PDBエントリ

全3件を表示しています

PDB-1gac:
NMR structure of asymmetric homodimer of a82846b, a glycopeptide antibiotic, complexed with its cell wall pentapeptide fragment

PDB-1gac:
NMR structure of asymmetric homodimer of a82846b, a glycopeptide antibiotic, complexed with its cell wall pentapeptide fragment

PDB-1gac:
NMR structure of asymmetric homodimer of a82846b, a glycopeptide antibiotic, complexed with its cell wall pentapeptide fragment