(4S)-4-{[(1S)-3-carbamoyl-1-{[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamoyl}propyl]carbamoyl}-4-(2-{2-[(2S)-2-{[(2S)-1-{2-[(2S)-2-(2-{2-[(2S)-2-{2-[(2S)-4-carbamoyl-2-[(2S)-2-{2-[(2S)-2-(2-{[(2S)-1-(2-acetamido-2-methylpropanoyl)pyrrolidin-2-yl]formamido}-2-methylpropanamido)propanamido]-2-methylpropanamido}propanamido]butanamido]-2-methylpropanamido}-3-methylbutanamido]-2-methylpropanamido}acetamido)-4-methylpentanamido]-2-methylpropanoyl}pyrrolidin-2-yl]formamido}-3-methylbutanamido]-2-methylpropanamido}-2-methylpropanamido)butanoic acid

• ChemBase ID: 125668
• Molecular Formular: C92H150N22O25
• Molecular Mass: 1964.3078
• Monoisotopic Mass: 1963.11424841
• SMILES: CC(C)C[C@@H](C(=O)NC(C)(C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](Cc1ccccc1)CO)NC(=O)CNC(=O)C(C)(C)NC(=O)[C@H](C(C)C)NC(=O)C(C)(C)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@@H]1CCCN1C(=O)C(C)(C)NC(=O)C
• Canonical SMILES: OC[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C(NC(=O)C(NC(=O)[C@H](C(C)C)NC(=O)[C@@H]1CCCN1C(=O)C(NC(=O)[C@@H](NC(=O)CNC(=O)C(NC(=O)[C@H](C(C)C)NC(=O)C(NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C(NC(=O)[C@@H](NC(=O)C(NC(=O)[C@@H]1CCCN1C(=O)C(NC(=O)C)(C)C)(C)C)C)(C)C)C)CCC(=O)N)(C)C)(C)C)CC(C)C)(C)C)(C)C)(C)C)CCC(=O)O)CCC(=O)N)Cc1ccccc1
• InChI: InChI=1S/C92H150N22O25/c1-47(2)43-58(72(127)108-92(24,25)84(139)113-41-29-33-59(113)73(128)103-65(48(3)4)75(130)111-90(20,21)82(137)112-89(18,19)80(135)102-56(37-40-64(120)121)70(125)101-55(35-38-61(93)117)69(124)98-54(46-115)44-53-31-27-26-28-32-53)99-63(119)45-95-77(132)85(10,11)110-76(131)66(49(5)6)104-81(136)88(16,17)107-71(126)57(36-39-62(94)118)100-67(122)50(7)96-78(133)86(12,13)106-68(123)51(8)97-79(134)87(14,15)109-74(129)60-34-30-42-114(60)83(138)91(22,23)105-52(9)116/h26-28,31-32,47-51,54-60,65-66,115H,29-30,33-46H2,1-25H3,(H2,93,117)(H2,94,118)(H,95,132)(H,96,133)(H,97,134)(H,98,124)(H,99,119)(H,100,122)(H,101,125)(H,102,135)(H,103,128)(H,104,136)(H,105,116)(H,106,123)(H,107,126)(H,108,127)(H,109,129)(H,110,131)(H,111,130)(H,112,137)(H,120,121)/t50-,51-,54-,55-,56-,57-,58-,59-,60-,65-,66-/m0/s1
• InChIKey: LGHSQOCGTJHDIL-UTXLBGCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-3-carbamoyl-1-{[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamoyl}propyl]carbamoyl}-4-(2-{2-[(2S)-2-{[(2S)-1-{2-[(2S)-2-(2-{2-[(2S)-2-{2-[(2S)-4-carbamoyl-2-[(2S)-2-{2-[(2S)-2-(2-{[(2S)-1-(2-acetamido-2-methylpropanoyl)pyrrolidin-2-yl]formamido}-2-methylpropanamido)propanamido]-2-methylpropanamido}propanamido]butanamido]-2-methylpropanamido}-3-methylbutanamido]-2-methylpropanamido}acetamido)-4-methylpentanamido]-2-methylpropanoyl}pyrrolidin-2-yl]formamido}-3-methylbutanamido]-2-methylpropanamido}-2-methylpropanamido)butanoic acid
• IUPAC Traditional name: alamethicin
• Synonyms: Alamethicin

Database IDs

• CAS Number: 27061-78-5
• PubChem SID: 162220018
• PubChem CID: 16132042
• CHEMBL: 438243
• Chemspider ID: 17288702
• Wikipedia Title: Alamethicin

CALCULATED PROPERTIES

• Acid pKa: 4.0946937
• H Acceptors: 25
• H Donor: 22
• LogD (pH = 5.5): -7.242025
• LogD (pH = 7.4): -8.925522
• Log P: -5.8232164
• Molar Refractivity: 499.6144 cm^3
• Polarizability: 195.59917 Å^3
• Polar Surface Area: 708.13 Å^2
• Rotatable Bonds: 53
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Insoluble in water; Soluble in DMSO, methanol, ethanol
• Apperance: Off white solid
• Melting Point: 255-270 °C