(1S,2R,18R,22S,25R,28R,40S)-22-(carbamoylmethyl)-47,49-dichloro-48-{[(2S,3R,4S,6R)-3-{[(2S,4S,5S,6S)-4-{[2-(decylamino)ethyl]amino}-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,18,32,35,37-pentahydroxy-19-[(2R)-4-methyl-2-(methylamino)pentanamido]-20,23,26,42,44-pentaoxo-36-{[(phosphonomethyl)amino]methyl}-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: 178115
• Molecular Formular: C80H106Cl2N11O27P
• Molecular Mass: 1755.634901
• Monoisotopic Mass: 1753.63742918
• SMILES: c1c2cc(c(c1)Oc1cc3cc(c1O[C@@H]1O[C@H](C([C@@H]([C@@H]1O[C@@H]1O[C@H]([C@H]([C@](C1)(NCCNCCCCCCCCCC)C)O)C)O)O)CO)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(c(c(c3)O)CNCP(=O)(O)O)O)C(=O)O)[C@@H]2O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl
• Canonical SMILES: CCCCCCCCCCNCCN[C@@]1(C)C[C@H](O[C@@H]2[C@@H](O[C@H](C([C@@H]2O)O)CO)Oc2c3cc4cc2Oc2ccc(cc2Cl)[C@@H](O)[C@@H]2NC(=O)[C@H](NC(=O)[C@@H]4NC(=O)[C@H](CC(=O)N)NC(=O)C([C@@H](c4ccc(O3)c(Cl)c4)O)NC(=O)[C@@H](CC(C)C)NC)c3ccc(c(c3)c3c([C@@H](NC2=O)C(=O)O)cc(c(c3O)CNCP(=O)(O)O)O)O)O[C@H]([C@H]1O)C
• InChI: InChI=1S/C80H106Cl2N11O27P/c1-7-8-9-10-11-12-13-14-21-85-22-23-87-80(5)32-57(115-37(4)71(80)103)119-70-68(102)67(101)55(34-94)118-79(70)120-69-53-28-41-29-54(69)117-52-20-17-40(27-46(52)82)65(99)63-77(109)91-61(78(110)111)43-30-50(96)44(33-86-35-121(112,113)114)66(100)58(43)42-25-38(15-18-49(42)95)59(74(106)93-63)90-75(107)60(41)89-73(105)48(31-56(83)97)88-76(108)62(92-72(104)47(84-6)24-36(2)3)64(98)39-16-19-51(116-53)45(81)26-39/h15-20,25-30,36-37,47-48,55,57,59-65,67-68,70-71,79,84-87,94-96,98-103H,7-14,21-24,31-35H2,1-6H3,(H2,83,97)(H,88,108)(H,89,105)(H,90,107)(H,91,109)(H,92,104)(H,93,106)(H,110,111)(H2,112,113,114)/t37-,47+,48-,55+,57-,59?,60+,61-,62?,63?,64+,65+,67?,68-,70+,71+,79-,80-/m0/s1
• InChIKey: ONUMZHGUFYIKPM-RKWQKVODSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,18R,22S,25R,28R,40S)-22-(carbamoylmethyl)-47,49-dichloro-48-{[(2S,3R,4S,6R)-3-{[(2S,4S,5S,6S)-4-{[2-(decylamino)ethyl]amino}-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,18,32,35,37-pentahydroxy-19-[(2R)-4-methyl-2-(methylamino)pentanamido]-20,23,26,42,44-pentaoxo-36-{[(phosphonomethyl)amino]methyl}-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-48-{[(2S,3R,4S,6R)-3-{[(2S,4S,5S,6S)-4-{[2-(decylamino)ethyl]amino}-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,18,32,35,37-pentahydroxy-19-[(2R)-4-methyl-2-(methylamino)pentanamido]-20,23,26,42,44-pentaoxo-36-{[(phosphonomethyl)amino]methyl}-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: N3''-[2-(Decylamino)ethyl]-29-[[(phosphonomethyl)amino]methyl]vancomycin; Arbelic; TelavancinDISCONTINUED

Database IDs

• CAS Number: 372151-71-8
• PubChem SID: 164234025
• PubChem CID: 71752341

CALCULATED PROPERTIES

• Acid pKa: 1.5501921
• H Acceptors: 29
• H Donor: 23
• LogD (pH = 5.5): -7.229935
• LogD (pH = 7.4): -5.932732
• Log P: -6.162543
• Molar Refractivity: 429.4118 cm^3
• Polarizability: 171.76878 Å^3
• Polar Surface Area: 598.09 Å^2
• Rotatable Bonds: 30
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T015800

Broad spectrum, semi-synthetic glycopeptide antibiotic; inhibits bacterial cell wall formation and disrupts cell membrane integrity. Antibacterial.

REFERENCES

• Judice, J.K., et al.: Bioorg. Med. Chem. Lett., 13, 4165 (2003)
• King, A., et al.: J. Antimicrob. Chemother., 53, 797 (2003)
• Stryjewski, M.E., et al.: Clin. Infect. Dis., 40, 1601 (2003)