(3S)-3-{[(1S)-1-{[(1S)-1-{[(1S,2R)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-2-carbamoyl-1-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-{[(1S)-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-[(2S,3R)-2-[(2S)-2-{[(2S)-1-[(2S)-5-carbamimidamido-2-[(2S)-5-carbamimidamido-2-{[(2S)-1-[(2S)-2,6-diaminohexanoyl]pyrrolidin-2-yl]formamido}pentanamido]pentanoyl]pyrrolidin-2-yl]formamido}-3-(4-hydroxyphenyl)propanamido]-3-hydroxybutanamido]propanoic acid

• ChemBase ID: 134280
• Molecular Formular: C154H257N49O40S
• Molecular Mass: 3467.05768
• Monoisotopic Mass: 3464.93031527
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(=O)N)C(=O)N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)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)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)CC(=O)N)CC(C)C)[C@H](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@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)N)CCCNC(=N)N)CCCNC(=N)N)Cc1ccc(cc1)O)CC(=O)O)CC(=O)N)Cc1ccc(cc1)O)CCCNC(=N)N)CC(C)C)CCCNC(=N)N
• InChI: InChI=1S/C154H257N49O40S/c1-15-81(10)120(146(239)195-104(68-79(6)7)134(227)187-101(123(164)216)72-115(161)211)199-142(235)111(76-204)197-138(231)109(74-117(163)213)192-135(228)103(67-78(4)5)189-136(229)105(69-85-40-46-88(207)47-41-85)190-130(223)93(32-18-22-57-157)179-127(220)94(33-19-23-58-158)184-145(238)119(80(8)9)198-124(217)82(11)177-125(218)99(54-65-244-14)182-132(225)98(52-53-114(160)210)181-126(219)92(31-17-21-56-156)178-128(221)95(34-24-59-173-151(165)166)180-133(226)102(66-77(2)3)188-131(224)97(36-26-61-175-153(169)170)185-147(240)121(83(12)205)200-140(233)106(70-86-42-48-89(208)49-43-86)191-137(230)108(73-116(162)212)193-139(232)110(75-118(214)215)196-148(241)122(84(13)206)201-141(234)107(71-87-44-50-90(209)51-45-87)194-144(237)113-39-29-64-203(113)150(243)100(37-27-62-176-154(171)172)186-129(222)96(35-25-60-174-152(167)168)183-143(236)112-38-28-63-202(112)149(242)91(159)30-16-20-55-155/h40-51,77-84,91-113,119-122,204-209H,15-39,52-76,155-159H2,1-14H3,(H2,160,210)(H2,161,211)(H2,162,212)(H2,163,213)(H2,164,216)(H,177,218)(H,178,221)(H,179,220)(H,180,226)(H,181,219)(H,182,225)(H,183,236)(H,184,238)(H,185,240)(H,186,222)(H,187,227)(H,188,224)(H,189,229)(H,190,223)(H,191,230)(H,192,228)(H,193,232)(H,194,237)(H,195,239)(H,196,241)(H,197,231)(H,198,217)(H,199,235)(H,200,233)(H,201,234)(H,214,215)(H4,165,166,173)(H4,167,168,174)(H4,169,170,175)(H4,171,172,176)/t81-,82-,83+,84+,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,119-,120-,121-,122-/m0/s1
• InChIKey: FBYWUGLFWCEKAN-KQQCXCAZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{[(1S)-1-{[(1S)-1-{[(1S,2R)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-2-carbamoyl-1-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-{[(1S)-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-[(2S,3R)-2-[(2S)-2-{[(2S)-1-[(2S)-5-carbamimidamido-2-[(2S)-5-carbamimidamido-2-{[(2S)-1-[(2S)-2,6-diaminohexanoyl]pyrrolidin-2-yl]formamido}pentanamido]pentanoyl]pyrrolidin-2-yl]formamido}-3-(4-hydroxyphenyl)propanamido]-3-hydroxybutanamido]propanoic acid
• IUPAC Traditional name: (3S)-3-{[(1S)-1-{[(1S)-1-{[(1S,2R)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-2-carbamoyl-1-{[(1S)-1-{[(1S,2S)-1-{[(1S)-1-{[(1S)-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-[(2S,3R)-2-[(2S)-2-{[(2S)-1-[(2S)-5-carbamimidamido-2-[(2S)-5-carbamimidamido-2-{[(2S)-1-[(2S)-2,6-diaminohexanoyl]pyrrolidin-2-yl]formamido}pentanamido]pentanoyl]pyrrolidin-2-yl]formamido}-3-(4-hydroxyphenyl)propanamido]-3-hydroxybutanamido]propanoic acid
• Synonyms: VIP Antagonist; VIPi; [Lys1, Pro2,5, Arg3,4, Tyr6]-VIP; [Lys1, Pro2,5, Arg3,4, Tyr6]-Vasoactive Intestinal Peptide human, porcine, rat

Database IDs

• CAS Number: 125093-93-8
• MDL Number: MFCD00133967
• PubChem SID: 162228557
• PubChem CID: 16144007

CALCULATED PROPERTIES

• Acid pKa: 3.4907086
• H Acceptors: 57
• H Donor: 54
• LogD (pH = 5.5): -35.225636
• LogD (pH = 7.4): -33.948326
• Log P: -19.526445
• Molar Refractivity: 923.8704 cm^3
• Polarizability: 345.14462 Å^3
• Polar Surface Area: 1519.95 Å^2
• Rotatable Bonds: 117
• 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)

Product Information

• Purity: ≥97% (HPLC)
• Compostion: Peptide content, ~70%

DETAILS

Sigma Aldrich - V2132

Amino Acid Sequence
Lys-Pro-Arg-Arg-Pro-Tyr-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
VIP receptor antagonist. Blocks VIP neurotransmission in the exocrine pancreas, but does not block the effects of PACAP, which shares 68% homology with VIP. In contrast, it blocks both VIP- and PACAP-stimulated cyclic AMP accumulation in an osteoblast-like cell line.