BIRD-PRD_000204: Vancomycin

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_000204
• 状態: 状態: REF ONLY
• 名称: Vancomycin

BIRD information

• タイプ: 糖ペプチド / 抗生剤

詳細

• VANCOMYCIN IS A TRICYCLIC GLYCOPEPTIDE. THE SCAFFOLD IS A HEPTAPEPTIDE WITH THE CONFIGURATION D-D-L-D-D-L-L. IT IS FURTHER GLYCOSYLATED BY A DISACCHARIDE MADE OF D-GLUCOSE AND VANCOSAMINE. HERE, VANCOMYCIN IS REPRESENTED BY GROUPING TOUGHER THE SEQUENCE (SEQRES) AND THE TWO LIGANDS (HET) BGC AND RER.
• VANCOMYCIN IS A TRICYCLIC GLYCOPEPTIDE, GLYCOSYLATED BY A DISACCHARIDE (RESIDUES 8 AND 9) ON RESIDUE 4.

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

別称

• (1S,2R,18R,22S,25R,28R,40R)-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,4S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-22-(carbamoylmethyl)-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-[(2R)-4-methyl-2-(methylamino)pentanamido]-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(39),35,37,46,49-pentadecaene-40-carboxylic acid (DrugBank)
• AIDS070034 (PubChem)
• Diatracin (SciFinder)
• EINECS 2150772-6 (PubChem)
• HSDB3262 (PubChem)
• K288 (Norine)
• LS-161387 (PubChem)
• Lopac-_001267 (PubChem)
• Lyphocin (ABX_Guide, ChemSpider)
• Prestwick0_000497 (PubChem)
• Prestwick1_000497 (PubChem)
• Prestwick2_000497 (PubChem)
• SPBio_002314 (PubChem)
• VANCOMYCIN (PDB)
• Vancin (Norine)
• Vancled (Norine)
• Vancocin (SciFinder, KEGG, DrugBank, ABX_Guide, PubChem, ChemSpider)
• Vancocin HCL (DrugBank)
• Vancocin Hydrochloride (KEGG)
• Vancocin Pulvule (ABX_Guide)
• Vancocine (SciFinder)
• Vancoled (DrugBank)
• Vancomicina (PubChem, ChemSpider)
• Vancomycin (SciFinder, KEGG, DrugBank, Norine, PubChem, ChemSpider)
• Vancomycin HCL (DrugBank)
• Vancomycin Hcl (ABX_Guide)
• Vancomycin Hydrochloride (ChemBank)
• Vancomycin Monohydrochloride (ChemBank)
• Vancomycine (PubChem, ChemSpider)
• Vancomycinum (PubChem, ChemSpider)
• Vancor (DrugBank, ChemSpider)
• vancomycin (Merck)

Annotation

• 分子機能: Antibacterial / 情報源: KEGG
• 分子機能: treatment of serious infections caused by susceptible strains of (beta-lactam-resistant) methicillin-resistant staphlococci / 情報源: DrugBank
• 分子機能: drug of last resort / 情報源: DrugBank
• 分子機能: cell wall synthesis inhibitor (prevents addition of N-acetylmuramic acid(NAM) and N-acetylglucosamine(NAG)-peptide subunits from being added into petidoglycan matrix, a major structural component of Gram-positive cell walls) / 情報源: DrugBank
• 分子機能: alters bacterial-cell-membrane permeability and RNA synthesis / 情報源: DrugBank
• 分子機能: Not active in vitro against gram-negative bacilli, mycobacteria, or fungi / 情報源: DrugBank
• 分子機能: 抗生剤 / 情報源: Norine
• 分子機能: Used in prophylaxis and treatment of infections caused by Gram-positive bacteria / 情報源: Norine
• 分子機能: Drug of last resort / 情報源: Norine
• 分子機能: Antibacterial / 情報源: NovelAntibiotics
• 分子機能: treatment of bone and joint infections, pneumonia, septicemia, endocarditis, and prophylaxis / 情報源: ABX_Guide
• 分子機能: antibacterial activity / 情報源: PubChem
• 分子機能: inhibits cell wall assembly / 情報源: PubChem
• 分子機能: toxic to kidneys and inner ear / 情報源: PubChem

由来

• Streptomyces orientalis (バクテリア), KEGG: D00212
• Amycolatopsis orientalis (バクテリア), Norine: NOR00681

External info

• ATC: A07AA09
• ATC: J01XA01
• Beilstein: 424559
• ChemBank: 1833
• ChemDB: 3969013
• DrugBank: DB00512
• Merck: 14:9929
• NovelAntibiotics: 510136
• ChemSpider: 14253
• Norine: NOR00681
• ChEBI: 28001
• PubChem: 14969
• CAS: 1404-90-6
• [KEGG_Compound_ID] KEGG: C06689
• [KEGG_Drug_ID] KEGG: D00212
• [MESH_Unique_ID] MESH: D014640
• WikiPedia: Vancomycin
• Vancomycin.co: www.vancomycin.co.uk
• Merck: vancomycin
• RXLIST: vancomycin.htm
• WikiPedia

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: C₆₆H₇₅Cl₂N₉O₂₄ / 化学式量: 1449.254

• その他: タイプ: peptide-like

履歴

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

詳細

SMILES

• CACTVS 3.385: CN[CH](CC(C)C)C(=O)N[CH]1[CH](O)c2ccc(Oc3cc4cc(Oc5ccc(cc5Cl)[CH](O)[CH]6NC(=O)[CH](NC(=O)[CH]4NC(=O)[CH](CC(N)=O)NC1=O)c7ccc(O)c(c7)c8c(O)cc(O)cc8[CH](NC6=O)C(O)=O)c3O[CH]9O[CH](CO)[CH](O)[CH](O)[CH]9O[CH]%10C[C](C)(N)[CH](O)[CH](C)O%10)c(Cl)c2
• OpenEye OEToolkits 2.0.7: CC1C(C(CC(O1)OC2C(C(C(OC2Oc3c4cc5cc3Oc6ccc(cc6Cl)C(C(C(=O)NC(C(=O)NC5C(=O)NC7c8ccc(c(c8)-c9c(cc(cc9O)O)C(NC(=O)C(C(c1ccc(c(c1)Cl)O4)O)NC7=O)C(=O)O)O)CC(=O)N)NC(=O)C(CC(C)C)NC)O)CO)O)O)(C)N)O

SMILES CANONICAL

• CACTVS 3.385: CN[C@H](CC(C)C)C(=O)N[C@@H]1[C@H](O)c2ccc(Oc3cc4cc(Oc5ccc(cc5Cl)[C@@H](O)[C@@H]6NC(=O)[C@H](NC(=O)[C@@H]4NC(=O)[C@H](CC(N)=O)NC1=O)c7ccc(O)c(c7)c8c(O)cc(O)cc8[C@H](NC6=O)C(O)=O)c3O[C@@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@H]9O[C@H]%10C[C@](C)(N)[C@H](O)[C@H](C)O%10)c(Cl)c2
• OpenEye OEToolkits 2.0.7: C[C@H]1[C@H]([C@@](C[C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2Oc3c4cc5cc3Oc6ccc(cc6Cl)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]7c8ccc(c(c8)-c9c(cc(cc9O)O)[C@H](NC(=O)[C@H]([C@@H](c1ccc(c(c1)Cl)O4)O)NC7=O)C(=O)O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)CO)O)O)(C)N)O

PDBエントリ

全24件を表示しています

1aa5

1aa5

1c0q

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1fvm

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1pnv

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1sho

1sho

3run

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5m2h

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7c4u

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