3-({1-[(1-{[1-({1-[(1-{[1-({5-amino-1-[(1-{[1-({1-[(1-{[5-amino-1-({5-amino-1-[(1-{[1-({2-carbamoyl-1-[(1-{[1-({1-[(1,2-dicarbamoylethyl)carbamoyl]-3-methylbutyl}carbamoyl)-2-methylbutyl]carbamoyl}-2-hydroxyethyl)carbamoyl]ethyl}carbamoyl)-3-methylbutyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl)carbamoyl]pentyl}carbamoyl)pentyl]carbamoyl}-2-methylpropyl)carbamoyl]ethyl}carbamoyl)-3-(methylsulfanyl)propyl]carbamoyl}-3-carbamoylpropyl)carbamoyl]pentyl}carbamoyl)-4-carbamimidamidobutyl]carbamoyl}-3-methylbutyl)carbamoyl]-4-carbamimidamidobutyl}carbamoyl)-2-hydroxypropyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl)carbamoyl]-2-carbamoylethyl}carbamoyl)-3-[2-(2-amino-3-phenylpropanamido)-3-hydroxybutanamido]propanoic acid

• ChemBase ID: 133141
• Molecular Formular: C126H207N37O34S
• Molecular Mass: 2816.28428
• Monoisotopic Mass: 2814.53268789
• SMILES: CCC(C)C(C(=O)NC(CC(C)C)C(=O)NC(CC(=O)N)C(=O)N)NC(=O)C(CO)NC(=O)C(CC(=O)N)NC(=O)C(CC(C)C)NC(=O)C(Cc1ccc(cc1)O)NC(=O)C(CCCCN)NC(=O)C(CCCCN)NC(=O)C(C(C)C)NC(=O)C(C)NC(=O)C(CCSC)NC(=O)C(CCC(=O)N)NC(=O)C(CCCCN)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(C)C)NC(=O)C(CCCNC(=N)N)NC(=O)C(C(C)O)NC(=O)C(Cc1ccc(cc1)O)NC(=O)C(CC(=O)N)NC(=O)C(CC(=O)O)NC(=O)C(C(C)O)NC(=O)C(Cc1ccccc1)N
• 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)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N)CC(=O)N)CC(C)C)C(CC)C)CO)CC(=O)N)CC(C)C)Cc1ccc(cc1)O)CCCCN)CCCCN)C(C)C)C)CCSC)CCC(=O)N)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(C(O)C)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(C(O)C)NC(=O)C(Cc1ccccc1)N)CC(=O)O)CC(=O)N)Cc1ccc(cc1)O)CCCNC(=N)N)CC(C)C)CCCNC(=N)N
• InChI: InChI=1S/C126H207N37O34S/c1-15-66(10)99(122(195)157-86(53-64(6)7)113(186)150-83(102(135)175)57-94(132)170)161-120(193)92(61-164)159-117(190)90(59-96(134)172)155-114(187)85(52-63(4)5)152-115(188)87(55-71-34-38-73(167)39-35-71)153-109(182)77(30-20-23-46-128)144-107(180)78(31-21-24-47-129)148-121(194)98(65(8)9)160-103(176)67(11)142-105(178)82(44-50-198-14)147-111(184)81(42-43-93(131)169)146-106(179)76(29-19-22-45-127)143-108(181)79(32-25-48-140-125(136)137)145-112(185)84(51-62(2)3)151-110(183)80(33-26-49-141-126(138)139)149-123(196)101(69(13)166)163-119(192)88(56-72-36-40-74(168)41-37-72)154-116(189)89(58-95(133)171)156-118(191)91(60-97(173)174)158-124(197)100(68(12)165)162-104(177)75(130)54-70-27-17-16-18-28-70/h16-18,27-28,34-41,62-69,75-92,98-101,164-168H,15,19-26,29-33,42-61,127-130H2,1-14H3,(H2,131,169)(H2,132,170)(H2,133,171)(H2,134,172)(H2,135,175)(H,142,178)(H,143,181)(H,144,180)(H,145,185)(H,146,179)(H,147,184)(H,148,194)(H,149,196)(H,150,186)(H,151,183)(H,152,188)(H,153,182)(H,154,189)(H,155,187)(H,156,191)(H,157,195)(H,158,197)(H,159,190)(H,160,176)(H,161,193)(H,162,177)(H,163,192)(H,173,174)(H4,136,137,140)(H4,138,139,141)
• InChIKey: BVEZAVADHLXCKB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-({1-[(1-{[1-({1-[(1-{[1-({5-amino-1-[(1-{[1-({1-[(1-{[5-amino-1-({5-amino-1-[(1-{[1-({2-carbamoyl-1-[(1-{[1-({1-[(1,2-dicarbamoylethyl)carbamoyl]-3-methylbutyl}carbamoyl)-2-methylbutyl]carbamoyl}-2-hydroxyethyl)carbamoyl]ethyl}carbamoyl)-3-methylbutyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl)carbamoyl]pentyl}carbamoyl)pentyl]carbamoyl}-2-methylpropyl)carbamoyl]ethyl}carbamoyl)-3-(methylsulfanyl)propyl]carbamoyl}-3-carbamoylpropyl)carbamoyl]pentyl}carbamoyl)-4-carbamimidamidobutyl]carbamoyl}-3-methylbutyl)carbamoyl]-4-carbamimidamidobutyl}carbamoyl)-2-hydroxypropyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl)carbamoyl]-2-carbamoylethyl}carbamoyl)-3-[2-(2-amino-3-phenylpropanamido)-3-hydroxybutanamido]propanoic acid
• IUPAC Traditional name: 3-({1-[(1-{[1-({1-[(1-{[1-({5-amino-1-[(1-{[1-({1-[(1-{[5-amino-1-({5-amino-1-[(1-{[1-({2-carbamoyl-1-[(1-{[1-({1-[(1,2-dicarbamoylethyl)carbamoyl]-3-methylbutyl}carbamoyl)-2-methylbutyl]carbamoyl}-2-hydroxyethyl)carbamoyl]ethyl}carbamoyl)-3-methylbutyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl)carbamoyl]pentyl}carbamoyl)pentyl]carbamoyl}-2-methylpropyl)carbamoyl]ethyl}carbamoyl)-3-(methylsulfanyl)propyl]carbamoyl}-3-carbamoylpropyl)carbamoyl]pentyl}carbamoyl)-4-carbamimidamidobutyl]carbamoyl}-3-methylbutyl)carbamoyl]-4-carbamimidamidobutyl}carbamoyl)-2-hydroxypropyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl)carbamoyl]-2-carbamoylethyl}carbamoyl)-3-[2-(2-amino-3-phenylpropanamido)-3-hydroxybutanamido]propanoic acid
• Synonyms: VIP 6-28; Vasoactive Intestinal Peptide Fragment 6-28 human, porcine, rat

Database IDs

• CAS Number: 69698-54-0
• MDL Number: MFCD00237319
• PubChem SID: 24900748; 162227418
• PubChem CID: 16133395

CALCULATED PROPERTIES

• Acid pKa: 3.490682
• H Acceptors: 44
• H Donor: 43
• LogD (pH = 5.5): -28.152412
• LogD (pH = 7.4): -25.216322
• Log P: -16.821795
• Molar Refractivity: 735.8605 cm^3
• Polarizability: 280.63657 Å^3
• Polar Surface Area: 1221.98 Å^2
• Rotatable Bonds: 97
• 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

Pharmacology Properties

• Gene Information: human ... VIP(7432)rat ... Vip(117064)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - V4508

Amino Acid Sequence
Phe-Thr-Asp-Asn-Tyr-Thr-Arg-Leu-Arg-Lys-Gln-Met-Ala-Val-Lys-Lys-Tyr-Leu-Asn-Ser-Ile-Leu-Asn-NH2
Biochem/physiol Actions
Potent VIP receptor antagonist