(1S,2R,18R,22S,25R,28R,40S)-22-(carbamoylmethyl)-47,49-dichloro-2,18,32,35,37,48-hexahydroxy-19-[(2R)-4-methyl-2-(methylamino)pentanamido]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8,10,12(48),14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid

• ChemBase ID: 179439
• Molecular Formular: C53H52Cl2N8O17
• Molecular Mass: 1143.92938
• Monoisotopic Mass: 1142.2827476
• SMILES: c1c2cc(c(c1)Oc1cc3cc(c1O)Oc1ccc(cc1Cl)[C@H](C(C(=O)N[C@H](C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(=O)N[C@H](c3c(c4cc1ccc4O)c(cc(c3)O)O)C(=O)O)[C@@H]2O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl
• Canonical SMILES: CN[C@@H](C(=O)NC1C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H]2c3cc(Oc4ccc([C@H]1O)cc4Cl)c(c(c3)Oc1ccc(cc1Cl)[C@H]([C@@H]1NC(=O)[C@H](NC2=O)c2ccc(c(c2)c2c(O)cc(cc2[C@@H](NC1=O)C(=O)O)O)O)O)O)CC(C)C
• InChI: InChI=1S/C53H52Cl2N8O17/c1-19(2)10-29(57-3)47(71)62-42-44(68)21-5-8-33(27(54)12-21)79-35-14-23-15-36(46(35)70)80-34-9-6-22(13-28(34)55)45(69)43-52(76)61-41(53(77)78)26-16-24(64)17-32(66)38(26)25-11-20(4-7-31(25)65)39(49(73)63-43)60-50(74)40(23)59-48(72)30(18-37(56)67)58-51(42)75/h4-9,11-17,19,29-30,39-45,57,64-66,68-70H,10,18H2,1-3H3,(H2,56,67)(H,58,75)(H,59,72)(H,60,74)(H,61,76)(H,62,71)(H,63,73)(H,77,78)/t29-,30+,39?,40-,41+,42?,43?,44-,45-/m1/s1
• InChIKey: JHIKFOISFAQTJQ-DDSGOOQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,18R,22S,25R,28R,40S)-22-(carbamoylmethyl)-47,49-dichloro-2,18,32,35,37,48-hexahydroxy-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,^6.2^1^4,^1^7.1^8,^1^2.1^2^9,^3^3.0^1^0,^2^5.0^3^4,^3^9]pentaconta-3,5,8,10,12(48),14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid
• IUPAC Traditional name: (1S,2R,18R,22S,25R,28R,40S)-22-(carbamoylmethyl)-47,49-dichloro-2,18,32,35,37,48-hexahydroxy-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,^6.2^1^4,^1^7.1^8,^1^2.1^2^9,^3^3.0^1^0,^2^5.0^3^4,^3^9]pentaconta-3,5,8,10,12(48),14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid
• Synonyms: 22H-8,11:18,21-Dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-1H,16H-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine, vancomycin Aglycone Derivative; Aglucovancomycin B; Aglycovancomycin; Balhimycin Aglycon; Vancomycin Aglycon

Database IDs

• CAS Number: 82198-76-3
• PubChem SID: 164235349
• PubChem CID: 71752913

CALCULATED PROPERTIES

• Acid pKa: 3.0773365
• H Acceptors: 16
• H Donor: 15
• LogD (pH = 5.5): -1.7379025
• LogD (pH = 7.4): -2.0564494
• Log P: -1.7370611
• Molar Refractivity: 278.8095 cm^3
• Polarizability: 109.96697 Å^3
• Polar Surface Area: 406.86 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - V096515

Vancomycin (V096500) impurity.

REFERENCES

• Mann, M., et al.: Curr. Opin. Biotechnol., 7, 11 (1996)
• Krone, J., et al.: Anal. Biochem., 244, 124 (1996)