(3S)-3-{[(1R)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-2-carboxy-1-{[(1S)-1-carboxy-2-hydroxyethyl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-methylpropyl]carbamoyl}pentyl]carbamoyl}-2-carbamoylethyl]carbamoyl}pentyl]carbamoyl}-3-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]propanoic acid

• ChemBase ID: 155507
• Molecular Formular: C44H73N13O16
• Molecular Mass: 1040.12792
• Monoisotopic Mass: 1039.52982332
• SMILES: CCCC[C@H](C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CO)C(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](Cc1c[nH]cn1)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CO)CC(=O)O)CC(C)C)C(C)C)NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](Cc1nc[nH]c1)N)CC(=O)O)CCCC)CC(=O)N
• InChI: InChI=1S/C44H73N13O16/c1-6-7-10-25(50-41(69)29(16-33(60)61)52-36(64)24(46)14-23-18-48-20-49-23)37(65)53-28(15-32(47)59)40(68)51-26(11-8-9-12-45)38(66)57-35(22(4)5)43(71)55-27(13-21(2)3)39(67)54-30(17-34(62)63)42(70)56-31(19-58)44(72)73/h18,20-22,24-31,35,58H,6-17,19,45-46H2,1-5H3,(H2,47,59)(H,48,49)(H,50,69)(H,51,68)(H,52,64)(H,53,65)(H,54,67)(H,55,71)(H,56,70)(H,57,66)(H,60,61)(H,62,63)(H,72,73)/t24-,25+,26-,27-,28-,29-,30-,31-,35-/m0/s1
• InChIKey: QSFXTURAJLIZNL-IBFMKUTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{[(1R)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-2-carboxy-1-{[(1S)-1-carboxy-2-hydroxyethyl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-methylpropyl]carbamoyl}pentyl]carbamoyl}-2-carbamoylethyl]carbamoyl}pentyl]carbamoyl}-3-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]propanoic acid
• IUPAC Traditional name: (3S)-3-{[(1R)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-2-carboxy-1-{[(1S)-1-carboxy-2-hydroxyethyl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-methylpropyl]carbamoyl}pentyl]carbamoyl}-2-carbamoylethyl]carbamoyl}pentyl]carbamoyl}-3-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]propanoic acid
• Synonyms: Nle-Antiflammin-2

Database IDs

• PubChem SID: 162249645
• PubChem CID: 71312146

CALCULATED PROPERTIES

• Acid pKa: 2.8191457
• H Acceptors: 19
• H Donor: 16
• LogD (pH = 5.5): -12.2883005
• LogD (pH = 7.4): -13.614902
• Log P: -12.048248
• Molar Refractivity: 251.052 cm^3
• Polarizability: 99.30246 Å^3
• Polar Surface Area: 488.74 Å^2
• Rotatable Bonds: 36
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Empirical Formula (Hill Notation): C47H79N13O15

DETAILS

Sigma Aldrich - A228

Application
Anti-inflammatory peptide; inhibits phospholipase A2 and the synthesis of platelet-activating factor.
Packaging
Product supplied in a sealed glass ampoule.