(3R,6R,11S,14S,17S,20S,23R,26S,29R,34R,37S,40R,45aS)-3,14,23,34,40-pentakis(carboxymethyl)-20-(hydroxymethyl)-11,17-bis[(4-hydroxyphenyl)methyl]-37-methyl-26-(2-methylpropyl)-1,4,9,12,15,18,21,24,27,32,35,38,41-tridecaoxo-tetratetracontahydro-1H-pyrrolo[2,1-}]1,4,7,10,13,16,19,24,27,30,33,36,39-tridecaazacyclotritetracontane-6,29-dicarboxylic acid

• ChemBase ID: 128480
• Molecular Formular: C65H85N13O30
• Molecular Mass: 1528.4395
• Monoisotopic Mass: 1527.55252839
• SMILES: O=C1N2CCC[C@H]2C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H](CCC(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@H](CCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H]1CC(=O)O)C)CC(=O)O)C(=O)O)CC(C)C)CC(=O)O)CO)Cc1ccc(O)cc1)CC(=O)O)Cc1ccc(O)cc1)C(=O)O
• Canonical SMILES: OC[C@@H]1NC(=O)[C@@H](Cc2ccc(cc2)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](NC(=O)CC[C@@H](NC(=O)[C@H](CC(=O)O)NC(=O)[C@@H]2CCCN2C(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CC[C@@H](NC(=O)[C@H](NC(=O)[C@H](NC1=O)CC(=O)O)CC(C)C)C(=O)O)CC(=O)O)C)CC(=O)O)C(=O)O)Cc1ccc(cc1)O
• InChI: InChI=1S/C65H85N13O30/c1-28(2)19-36-55(96)69-34(64(105)106)15-17-47(83)68-39(22-48(84)85)54(95)66-29(3)53(94)76-43(26-52(92)93)63(104)78-18-4-5-45(78)62(103)75-42(25-51(90)91)58(99)70-35(65(107)108)14-16-46(82)67-37(20-30-6-10-32(80)11-7-30)56(97)73-40(23-49(86)87)60(101)72-38(21-31-8-12-33(81)13-9-31)57(98)77-44(27-79)61(102)74-41(24-50(88)89)59(100)71-36/h6-13,28-29,34-45,79-81H,4-5,14-27H2,1-3H3,(H,66,95)(H,67,82)(H,68,83)(H,69,96)(H,70,99)(H,71,100)(H,72,101)(H,73,97)(H,74,102)(H,75,103)(H,76,94)(H,77,98)(H,84,85)(H,86,87)(H,88,89)(H,90,91)(H,92,93)(H,105,106)(H,107,108)/t29-,34+,35+,36-,37-,38-,39+,40-,41+,42+,43+,44-,45-/m0/s1
• InChIKey: MGMBOQJARKXIAL-LCLLRQAKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,6R,11S,14S,17S,20S,23R,26S,29R,34R,37S,40R,45aS)-3,14,23,34,40-pentakis(carboxymethyl)-20-(hydroxymethyl)-11,17-bis[(4-hydroxyphenyl)methyl]-37-methyl-26-(2-methylpropyl)-1,4,9,12,15,18,21,24,27,32,35,38,41-tridecaoxo-tetratetracontahydro-1H-pyrrolo[2,1-}]1,4,7,10,13,16,19,24,27,30,33,36,39-tridecaazacyclotritetracontane-6,29-dicarboxylic acid
• IUPAC Traditional name: mycobacillin
• Synonyms: Cyclo(L-alanyl-D-α-aspartyl-L-prolyl-D-α-aspartyl-D-γ-glutamyl-L-tyrosyl-L-α-aspartyl-L-tyrosyl-L-seryl-D-α-aspartyl-L-leucyl-D-γ-glutamyl-D-α-aspartyl); Mycobacillin

Database IDs

• CAS Number: 18524-67-9
• PubChem SID: 162222787
• PubChem CID: 16129676; 57307378
• Wikipedia Title: Mycobacillin

CALCULATED PROPERTIES

• LogD (pH = 5.5): -19.289848
• LogD (pH = 7.4): -30.259459
• Log P: -7.70472
• Molar Refractivity: 352.7302 cm^3
• Polarizability: 138.48466 Å^3
• Polar Surface Area: 691.3 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false
• Acid pKa: 2.920858
• H Acceptors: 30
• H Donor: 22

PROPERTIES

Physical Property

• Melting Point: 235–240 °C