2-{[1-(2-{2-[2-(2-amino-3-phenylpropanamido)acetamido]-3-phenylpropanamido}-4-methylpentanoyl)pyrrolidin-2-yl]formamido}-N-(1-{[4-carbamimidamido-1-({5-carbamimidamido-1-[2-({1-[(1-carbamoyl-2-hydroxyethyl)carbamoyl]ethyl}carbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl}carbamoyl)butyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl)-3-methylpentanamide

• ChemBase ID: 133222
• Molecular Formular: C69H103N19O14
• Molecular Mass: 1422.67502
• Monoisotopic Mass: 1421.79318907
• SMILES: CCC(C)C(C(=O)NC(Cc1ccc(cc1)O)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCNC(=N)N)C(=O)N1CCCC1C(=O)NC(C)C(=O)NC(CO)C(=O)N)NC(=O)C1CCCN1C(=O)C(CC(C)C)NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)C(Cc1ccccc1)N
• Canonical SMILES: CCC(C(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1CCCC1C(=O)NC(C(=O)NC(C(=O)N)CO)C)CCCNC(=N)N)CCCNC(=N)N)Cc1ccc(cc1)O)NC(=O)C1CCCN1C(=O)C(NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)C(Cc1ccccc1)N)CC(C)C)C
• InChI: InChI=1S/C69H103N19O14/c1-6-40(4)56(86-64(99)54-24-16-32-88(54)67(102)51(33-39(2)3)84-61(96)49(35-43-19-11-8-12-20-43)80-55(91)37-78-59(94)46(70)34-42-17-9-7-10-18-42)65(100)83-50(36-44-25-27-45(90)28-26-44)62(97)81-47(21-13-29-76-68(72)73)60(95)82-48(22-14-30-77-69(74)75)66(101)87-31-15-23-53(87)63(98)79-41(5)58(93)85-52(38-89)57(71)92/h7-12,17-20,25-28,39-41,46-54,56,89-90H,6,13-16,21-24,29-38,70H2,1-5H3,(H2,71,92)(H,78,94)(H,79,98)(H,80,91)(H,81,97)(H,82,95)(H,83,100)(H,84,96)(H,85,93)(H,86,99)(H4,72,73,76)(H4,74,75,77)
• InChIKey: IQNSWGKGZHMSIZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[1-(2-{2-[2-(2-amino-3-phenylpropanamido)acetamido]-3-phenylpropanamido}-4-methylpentanoyl)pyrrolidin-2-yl]formamido}-N-(1-{[4-carbamimidamido-1-({5-carbamimidamido-1-[2-({1-[(1-carbamoyl-2-hydroxyethyl)carbamoyl]ethyl}carbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl}carbamoyl)butyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl)-3-methylpentanamide
• IUPAC Traditional name: 2-{[1-(2-{2-[2-(2-amino-3-phenylpropanamido)acetamido]-3-phenylpropanamido}-4-methylpentanoyl)pyrrolidin-2-yl]formamido}-N-(1-{[4-carbamimidamido-1-({5-carbamimidamido-1-[2-({1-[(1-carbamoyl-2-hydroxyethyl)carbamoyl]ethyl}carbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl}carbamoyl)butyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl)-3-methylpentanamide
• Synonyms: Phe-Gly-Phe-Leu-Pro-Ile-Tyr-Arg-Arg-Pro-Ala-Ser-NH2; Granuliberin R

Database IDs

• CAS Number: 64704-41-2
• MDL Number: MFCD00080191
• PubChem SID: 24895328; 162227499
• PubChem CID: 25082836

CALCULATED PROPERTIES

• Acid pKa: 9.503247
• H Acceptors: 21
• H Donor: 19
• LogD (pH = 5.5): -9.903517
• LogD (pH = 7.4): -7.9521165
• Log P: -4.0404506
• Molar Refractivity: 394.9786 cm^3
• Polarizability: 145.47661 Å^3
• Polar Surface Area: 535.89 Å^2
• Rotatable Bonds: 40
• Lipinski's Rule of Five: false

PROPERTIES

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

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - G7897

Biochem/physiol Actions
Mast cell degranulating peptide found in the skin of the frog, Rana rugosa.