(1S,18R,19R,22S,25R,28R,40R)-4-{[(2S,4R,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,4R,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-49-chloro-32,35,37-trihydroxy-22-(4-hydroxyphenyl)-19-[(2S)-2-(methylamino)-2-(4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)acetamido]-20,23,26,42,44-pentaoxo-18-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-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(48),9,11,14,16,29,31,33(45),34,36,38,46,49-pentadecaene-40-carboxylic acid

• ChemBase ID: 125987
• Molecular Formular: C89H102ClN9O36
• Molecular Mass: 1909.25388
• Monoisotopic Mass: 1907.61159831
• SMILES: CN[C@H](C(=O)N[C@@H]1[C@H](O[C@@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@H]2O)c2ccc(cc2)Oc2cc3cc(Oc4cc(O[C@H]5C[C@@H](N)[C@@H](O)[C@H](C)O5)c(cc4Cl)C[C@@H]4NC(=O)[C@H](NC(=O)[C@@H]3NC(=O)[C@@H](NC1=O)c1ccc(O)cc1)c1ccc(O)c(c1)c1c(O)cc(O)cc1[C@@H](NC4=O)C(=O)O)c2O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@H]1C[C@@H](N)[C@@H](O)[C@H](C)O1)c1ccc(O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)cc1
• Canonical SMILES: OC[C@@H]1O[C@@H](O[C@@H]2c3ccc(cc3)Oc3cc4[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]2NC(=O)[C@H](c2ccc(cc2)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)NC)c2ccc(cc2)O)C(=O)N[C@H]2C(=O)N[C@@H](Cc5c(cc(Oc(c3O[C@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O[C@H]3C[C@@H](N)[C@H]([C@@H](O3)C)O)O)O)c4)c(Cl)c5)O[C@H]3C[C@@H](N)[C@H]([C@@H](O3)C)O)C(=O)N[C@H](c3c(c4cc2ccc4O)c(O)cc(c3)O)C(=O)O)[C@@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C89H102ClN9O36/c1-31-67(106)47(91)26-58(124-31)130-52-28-53-46(90)20-38(52)21-49-80(116)98-65(86(122)123)45-24-41(103)25-51(105)60(45)44-19-37(11-18-50(44)104)63(82(118)94-49)96-84(120)64-39-22-54(78(55(23-39)129-53)135-89-79(74(113)71(110)57(30-101)132-89)133-59-27-48(92)68(107)32(2)125-59)127-42-16-9-36(10-17-42)77(134-88-76(115)73(112)70(109)56(29-100)131-88)66(85(121)95-62(83(119)97-64)35-5-12-40(102)13-6-35)99-81(117)61(93-4)34-7-14-43(15-8-34)128-87-75(114)72(111)69(108)33(3)126-87/h5-20,22-25,28,31-33,47-49,56-59,61-77,79,87-89,93,100-115H,21,26-27,29-30,91-92H2,1-4H3,(H,94,118)(H,95,121)(H,96,120)(H,97,119)(H,98,116)(H,99,117)(H,122,123)/t31-,32-,33-,47+,48+,49-,56-,57+,58-,59-,61-,62-,63+,64+,65+,66+,67-,68-,69-,70-,71+,72+,73+,74-,75+,76+,77+,79+,87-,88-,89-/m0/s1
• InChIKey: JWFVWARSGMYXRN-HTQQBIQNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,18R,19R,22S,25R,28R,40R)-4-{[(2S,4R,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,4R,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-49-chloro-32,35,37-trihydroxy-22-(4-hydroxyphenyl)-19-[(2S)-2-(methylamino)-2-(4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)acetamido]-20,23,26,42,44-pentaoxo-18-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-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(48),9,11,14,16,29,31,33(45),34,36,38,46,49-pentadecaene-40-carboxylic acid
• IUPAC Traditional name: (1S,18R,19R,22S,25R,28R,40R)-4-{[(2S,4R,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,4R,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-49-chloro-32,35,37-trihydroxy-22-(4-hydroxyphenyl)-19-[(2S)-2-(methylamino)-2-(4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)acetamido]-20,23,26,42,44-pentaoxo-18-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-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(48),9,11,14,16,29,31,33(45),34,36,38,46,49-pentadecaene-40-carboxylic acid
• Synonyms: Avoparcin

Database IDs

• CAS Number: 37332-99-3
• PubChem SID: 162220330
• PubChem CID: 20055225
• Chemspider ID: 16736403
• Wikipedia Title: Avoparcin

CALCULATED PROPERTIES

• Acid pKa: 2.8851175
• H Acceptors: 37
• H Donor: 26
• LogD (pH = 5.5): -10.038316
• LogD (pH = 7.4): -7.217785
• Log P: -6.0991144
• Molar Refractivity: 453.859 cm^3
• Polarizability: 183.1177 Å^3
• Polar Surface Area: 710.41 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false