(1S,2R,19R,22R,34S,37R,40R,52S)-22-amino-5,63-dichloro-64-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(8-methylnonanamido)oxan-2-yl]oxy}-2-{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-26,31,44,49-tetrahydroxy-21,35,38,54,56,59-hexaoxo-47-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7,13,28-trioxa-20,36,39,53,55,58-hexaazaundecacyclo[38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylic acid

• ChemBase ID: 178114
• Molecular Formular: C88H97Cl2N9O33
• Molecular Mass: 1879.65828
• Monoisotopic Mass: 1877.55658197
• SMILES: c1c2ccc(c1Cl)Oc1cc3cc(c1O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1NC(=O)CCCCCCC(C)C)O)O)CO)Oc1ccc(cc1Cl)C[C@@H]1C(=O)N[C@H](C(=O)N[C@H]3C(=O)N[C@H]3C(=O)N[C@@H]([C@@H]2O[C@@H]2O[C@H]([C@H]([C@@H]([C@@H]2NC(=O)C)O)O)CO)C(=O)N[C@H](c2c(c4cc3ccc4O)c(cc(c2)O)O[C@@H]2[C@H]([C@@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)O)c2cc(cc(c2)Oc2c(ccc([C@H](C(=O)N1)N)c2)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](Oc2c3cc4cc2Oc2ccc(cc2Cl)C[C@@H]2C(=O)N[C@H](C(=O)N[C@H]4C(=O)N[C@H]4C(=O)N[C@@H]([C@@H](c5ccc(O3)c(Cl)c5)O[C@@H]3O[C@@H](CO)[C@H]([C@@H]([C@@H]3NC(=O)C)O)O)C(=O)N[C@H](c3c(c5cc4ccc5O)c(cc(c3)O)O[C@H]3O[C@H](CO)[C@H]([C@H]([C@@H]3O)O)O)C(=O)O)c3cc(O)cc(c3)Oc3cc([C@H](C(=O)N2)N)ccc3O)[C@H]([C@H]([C@@H]1O)O)NC(=O)CCCCCCC(C)C
• InChI: InChI=1S/C88H97Cl2N9O33/c1-33(2)8-6-4-5-7-9-60(108)94-68-74(113)71(110)58(31-101)129-87(68)132-78-55-25-40-26-56(78)126-52-17-13-38(23-47(52)90)77(131-86-67(92-34(3)103)73(112)70(109)57(30-100)128-86)69-84(121)98-66(85(122)123)45-28-42(105)29-54(127-88-76(115)75(114)72(111)59(32-102)130-88)61(45)44-22-37(12-14-49(44)106)63(81(118)99-69)96-83(120)65(40)97-82(119)64-39-20-41(104)27-43(21-39)124-53-24-36(11-15-50(53)107)62(91)80(117)93-48(79(116)95-64)19-35-10-16-51(125-55)46(89)18-35/h10-18,20-29,33,48,57-59,62-77,86-88,100-102,104-107,109-115H,4-9,19,30-32,91H2,1-3H3,(H,92,103)(H,93,117)(H,94,108)(H,95,116)(H,96,120)(H,97,119)(H,98,121)(H,99,118)(H,122,123)/t48?,57-,58-,59-,62-,63?,64?,65-,66+,67-,68-,69?,70-,71-,72-,73-,74-,75+,76+,77-,86+,87+,88+/m1/s1
• InChIKey: GHOXVFYORXUCPY-URFIKAHSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,19R,22R,34S,37R,40R,52S)-22-amino-5,63-dichloro-64-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(8-methylnonanamido)oxan-2-yl]oxy}-2-{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-26,31,44,49-tetrahydroxy-21,35,38,54,56,59-hexaoxo-47-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7,13,28-trioxa-20,36,39,53,55,58-hexaazaundecacyclo[38.14.2.2^3,^6.2^1^4,^1^7.2^1^9,^3^4.1^8,^1^2.1^2^3,^2^7.1^2^9,^3^3.1^4^1,^4^5.0^1^0,^3^7.0^4^6,^5^1]hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylic acid
• IUPAC Traditional name: (1S,2R,19R,22R,34S,37R,40R,52S)-22-amino-5,63-dichloro-64-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(8-methylnonanamido)oxan-2-yl]oxy}-2-{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-26,31,44,49-tetrahydroxy-21,35,38,54,56,59-hexaoxo-47-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7,13,28-trioxa-20,36,39,53,55,58-hexaazaundecacyclo[38.14.2.2^3,^6.2^1^4,^1^7.2^1^9,^3^4.1^8,^1^2.1^2^3,^2^7.1^2^9,^3^3.1^4^1,^4^5.0^1^0,^3^7.0^4^6,^5^1]hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylic acid
• Synonyms: Teicoplanin A2; Teichomycin A2; MDL-507; Targocid; Targosid; Teicoplanin

Database IDs

• CAS Number: 91032-26-7
• PubChem SID: 164234024
• PubChem CID: 16198036

CALCULATED PROPERTIES

• Acid pKa: 3.036166
• H Acceptors: 31
• H Donor: 24
• LogD (pH = 5.5): -2.4189506
• LogD (pH = 7.4): -2.8004017
• Log P: -2.4168184
• Molar Refractivity: 450.855 cm^3
• Polarizability: 179.9767 Å^3
• Polar Surface Area: 662.41 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol; Water
• Apperance: White Amorphous Powder
• Melting Point: 250°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T015500

Glycopeptide antibiotic complex produced by Actinoplanes teichomyceticus; structurally related to vancomycin. Comprised of 5 major components differentiated by a specific fatty acid moiety. Inhibits peptidoglycan synthesis in the cell wall of gram-positiv

REFERENCES

• Cynamon, M.H., et al.: Antimicrob. Agents Chemother., 21, 504 (1982)
• Williams, A.H., et al.: J. Antimicrob. Chemother., 14, 441 (1982)
• Dunayevskiy, Y., et al.: J. Med. Chem., 41, 1201 (1982)
• Chinchilla, D., et al.: Anal. Bioanal. Chem., 383, 625 (2005)