4-[2-(2-{6-amino-2-[2-(2-aminoacetamido)-3-phenylpropanamido]hexanamido}-3-carbamoylpropanamido)-3-methylbutanamido]-4-[(1-{[1-({1-[(1-{[4-carbamimidamido-1-({[(1-carbamoyl-2-phenylethyl)carbamoyl]methyl}carbamoyl)butyl]carbamoyl}ethyl)carbamoyl]-2-hydroxypropyl}carbamoyl)-3-(methylsulfanyl)propyl]carbamoyl}-3-(methylsulfanyl)propyl)carbamoyl]butanoic acid

• ChemBase ID: 153339
• Molecular Formular: C65H103N19O17S2
• Molecular Mass: 1486.76042
• Monoisotopic Mass: 1485.72207493
• SMILES: CC(C)C(C(=O)NC(CCC(=O)O)C(=O)NC(CCSC)C(=O)NC(CCSC)C(=O)NC(C(C)O)C(=O)NC(C)C(=O)NC(CCCNC(=N)N)C(=O)NCC(=O)NC(Cc1ccccc1)C(=O)N)NC(=O)C(CC(=O)N)NC(=O)C(CCCCN)NC(=O)C(Cc1ccccc1)NC(=O)CN
• Canonical SMILES: NCCCCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)N)Cc1ccccc1)CCCNC(=N)N)C)C(O)C)CCSC)CCSC)CCC(=O)O)C(C)C)CC(=O)N)NC(=O)C(Cc1ccccc1)NC(=O)CN
• InChI: InChI=1S/C65H103N19O17S2/c1-35(2)52(83-62(99)47(32-48(68)86)82-57(94)41(20-13-14-26-66)78-61(98)46(76-49(87)33-67)31-39-18-11-8-12-19-39)63(100)81-42(22-23-51(89)90)58(95)79-43(24-28-102-5)59(96)80-44(25-29-103-6)60(97)84-53(37(4)85)64(101)74-36(3)55(92)77-40(21-15-27-72-65(70)71)56(93)73-34-50(88)75-45(54(69)91)30-38-16-9-7-10-17-38/h7-12,16-19,35-37,40-47,52-53,85H,13-15,20-34,66-67H2,1-6H3,(H2,68,86)(H2,69,91)(H,73,93)(H,74,101)(H,75,88)(H,76,87)(H,77,92)(H,78,98)(H,79,95)(H,80,96)(H,81,100)(H,82,94)(H,83,99)(H,84,97)(H,89,90)(H4,70,71,72)
• InChIKey: VOQFXDFZGBDKIR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[2-(2-{6-amino-2-[2-(2-aminoacetamido)-3-phenylpropanamido]hexanamido}-3-carbamoylpropanamido)-3-methylbutanamido]-4-[(1-{[1-({1-[(1-{[4-carbamimidamido-1-({[(1-carbamoyl-2-phenylethyl)carbamoyl]methyl}carbamoyl)butyl]carbamoyl}ethyl)carbamoyl]-2-hydroxypropyl}carbamoyl)-3-(methylsulfanyl)propyl]carbamoyl}-3-(methylsulfanyl)propyl)carbamoyl]butanoic acid
• IUPAC Traditional name: 4-[2-(2-{6-amino-2-[2-(2-aminoacetamido)-3-phenylpropanamido]hexanamido}-3-carbamoylpropanamido)-3-methylbutanamido]-4-[(1-{[1-({1-[(1-{[4-carbamimidamido-1-({[(1-carbamoyl-2-phenylethyl)carbamoyl]methyl}carbamoyl)butyl]carbamoyl}ethyl)carbamoyl]-2-hydroxypropyl}carbamoyl)-3-(methylsulfanyl)propyl]carbamoyl}-3-(methylsulfanyl)propyl)carbamoyl]butanoic acid
• Synonyms: Gly-Phe-Lys-Asn-Val-Glu-Met-Met-Thr-Ala-Arg-Gly-Phe-NH2; Allatotropin

Database IDs

• CAS Number: 120928-88-3
• PubChem SID: 162247478
• PubChem CID: 71311646

CALCULATED PROPERTIES

• Acid pKa: -1.0257459
• H Acceptors: 22
• H Donor: 21
• LogD (pH = 5.5): -13.868466
• LogD (pH = 7.4): -11.75331
• Log P: -8.764331
• Molar Refractivity: 388.66 cm^3
• Polarizability: 148.16512 Å^3
• Polar Surface Area: 606.85 Å^2
• Rotatable Bonds: 50
• 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)
• Compostion: Peptide content, ~70%
• Empirical Formula (Hill Notation): C65H103N19O17S2

DETAILS

Sigma Aldrich - A1686

Biochem/physiol Actions
Novel Manduca sexta neurohormone which stimulates the release of juvenile hormone from the corpora allata in vitro.