(1R,18R,19S,22S,34R,37R,40S,53R)-53-amino-5,15-dichloro-64-{[(1R,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-(8-methylnonanamido)cyclohexyl]oxy}-18-{[(2R,3R,4R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-25,30,43,48-tetrahydroxy-20,36,39,54,56,59-hexaoxo-27-{[(1R,2S,3S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxy}-7,13,46-trioxa-21,35,38,55,57,60-hexaazaundecacyclo[38.15.2.23,6.214,17.219,34.18,12.129,33.141,45.010,37.023,28.047,52]hexahexaconta-3,5,8,10,12(64),14,16,23(28),24,26,29(61),30,32,41(58),42,44,47(52),48,50,62,65-henicosaene-22-carboxylic acid

• ChemBase ID: 179712
• Molecular Formular: C90H101Cl2N9O31
• Molecular Mass: 1875.71264
• Monoisotopic Mass: 1873.59805286
• SMILES: [C@@H]12NC(=O)[C@H](NC(=O)[C@@H]3NC(=O)[C@H]4NC(=O)[C@H](NC(=O)[C@@H](c5c(Oc6cc4cc(c6)O)c(O)ccc5)N)Cc4cc(c(Oc5c(c(Oc6c(cc([C@H]2O[C@H]2[C@@H]([C@H](C([C@H](O2)CO)O)O)NC(=O)C)cc6)Cl)cc3c5)O[C@H]2[C@@H]([C@H](C([C@H](C2)CO)O)O)NC(=O)CCCCCCC(C)C)cc4)Cl)c2cc(c3c([C@H](NC1=O)C(=O)O)cc(cc3O[C@H]1[C@H]([C@H](C([C@H](C1)CO)O)O)O)O)c(cc2)O
• Canonical SMILES: OC[C@H]1C[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([C@@H]([C@H]3NC(=O)C)O)O)C(=O)N[C@@H](c3c(c5cc4ccc5O)c(cc(c3)O)O[C@@H]3C[C@H](CO)C([C@@H]([C@@H]3O)O)O)C(=O)O)c3cc(O)cc(c3)Oc3c([C@H](C(=O)N2)N)cccc3O)[C@@H]([C@H](C1O)O)NC(=O)CCCCCCC(C)C
• InChI: InChI=1S/C90H101Cl2N9O31/c1-35(2)9-6-4-5-7-12-63(110)96-70-58(27-42(32-102)73(111)77(70)115)130-82-60-25-41-26-61(82)128-56-18-15-39(24-51(56)92)80(132-90-71(94-36(3)105)78(116)76(114)62(34-104)131-90)72-88(123)100-69(89(124)125)49-30-45(107)31-57(129-59-28-43(33-103)74(112)79(117)75(59)113)64(49)48-23-38(14-16-53(48)108)66(85(120)101-72)98-87(122)68(41)99-86(121)67-40-21-44(106)29-46(22-40)126-81-47(10-8-11-54(81)109)65(93)84(119)95-52(83(118)97-67)20-37-13-17-55(127-60)50(91)19-37/h8,10-11,13-19,21-26,29-31,35,42-43,52,58-59,62,65-80,90,102-104,106-109,111-117H,4-7,9,12,20,27-28,32-34,93H2,1-3H3,(H,94,105)(H,95,119)(H,96,110)(H,97,118)(H,98,122)(H,99,121)(H,100,123)(H,101,120)(H,124,125)/t42-,43-,52?,58-,59-,62-,65-,66?,67?,68-,69+,70+,71-,72?,73?,74?,75-,76?,77-,78-,79+,80-,90+/m1/s1
• InChIKey: MJRQUHHZUFSBLY-RNWCHONWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,18R,19S,22S,34R,37R,40S,53R)-53-amino-5,15-dichloro-64-{[(1R,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-(8-methylnonanamido)cyclohexyl]oxy}-18-{[(2R,3R,4R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-25,30,43,48-tetrahydroxy-20,36,39,54,56,59-hexaoxo-27-{[(1R,2S,3S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxy}-7,13,46-trioxa-21,35,38,55,57,60-hexaazaundecacyclo[38.15.2.2^3,^6.2^1^4,^1^7.2^1^9,^3^4.1^8,^1^2.1^2^9,^3^3.1^4^1,^4^5.0^1^0,^3^7.0^2^3,^2^8.0^4^7,^5^2]hexahexaconta-3,5,8,10,12(64),14,16,23(28),24,26,29(61),30,32,41(58),42,44,47(52),48,50,62,65-henicosaene-22-carboxylic acid
• IUPAC Traditional name: (1R,18R,19S,22S,34R,37R,40S,53R)-53-amino-5,15-dichloro-64-{[(1R,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-(8-methylnonanamido)cyclohexyl]oxy}-18-{[(2R,3R,4R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-25,30,43,48-tetrahydroxy-20,36,39,54,56,59-hexaoxo-27-{[(1R,2S,3S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxy}-7,13,46-trioxa-21,35,38,55,57,60-hexaazaundecacyclo[38.15.2.2^3,^6.2^1^4,^1^7.2^1^9,^3^4.1^8,^1^2.1^2^9,^3^3.1^4^1,^4^5.0^1^0,^3^7.0^2^3,^2^8.0^4^7,^5^2]hexahexaconta-3,5,8,10,12(64),14,16,23(28),24,26,29(61),30,32,41(58),42,44,47(52),48,50,62,65-henicosaene-22-carboxylic acid
• Synonyms: Targocid; Teicoplanin

Database IDs

• CAS Number: 61036-62-2
• PubChem SID: 164235622
• PubChem CID: 71753043

CALCULATED PROPERTIES

• Acid pKa: 3.0996768
• H Acceptors: 29
• H Donor: 24
• LogD (pH = 5.5): -2.505646
• LogD (pH = 7.4): -3.2128212
• Log P: -2.4927905
• Molar Refractivity: 458.3312 cm^3
• Polarizability: 182.14583 Å^3
• Polar Surface Area: 643.95 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Inhibitor of bacterial cell wall synthesis

Product Information

• Description: Teicoplanin A2 1-5
• Biological Source: Isol. from Actinoplanes teichomyceticus
• Application(s): Antibiotic; Highly active against staphylococci and gram-positive anaerobes

REFERENCES

• Ger. Pat., 1976, Gruppo Lepetit, 2 608 216; CA, 86, 3563x, (isol)
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• Parenti, F. et al., J. Antibiot., 1978, 31, 276, (isol, props)
• Pallanza, R. et al., J. Antimicrob. Chemother., 1983, 11, 94; 419, (props)
• Borghi, A. et al., J. Antibiot., 1984, 37, 615; 1989, 42, 361, (isol, struct, bibl)
• Malabaric, J.C. et al., J. Antibiot., 1984, 37, 988, (struct)
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• Parenti, F. et al., Fortschr. Antimikrob. Antineoplast. Chemother., 1991, 10, 105; 111, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 211
• Brogden, R.N. et al., Drugs, 1994, 47, 823, (rev)
• Goldstein, B.P. et al., Glycopept. Antibiot., (Ed. Nagarajan, R.), M. Dekker, 1994, 273-307, (rev)
• Trautmann, M. et al., Infection (Munich), 1994, 22, 430, (rev)
• McMullin, C.M. et al., J. Antimicrob. Chemother., 1994, 34, 425, (hplc)
• Heydorn, A. et al., J. Biol. Chem., 2000, 275, 6201-6206, (biosynth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TAI400