VIP   Click here for help

GtoPdb Ligand ID: 1152

Immunopharmacology Ligand
Compound class: Endogenous peptide in human, mouse or rat
Comment: Sequences of human, mouse and rat VIP are identical

VIP was first isolated and sequenced from pig small intestine [12,15].

As with many peptide molecules, there is ambiguity surrounding representations of the exact stereochemistry of VIP. The structure shown here does not specify stereochemistry.
Species: Human, Mouse, Rat
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View more information in the IUPHAR Pharmacology Education Project: vasoactive intestinal peptide

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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)O)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(NC(=O)C(C(C)C)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(Cc1nc[nH]c1)N)CO)CC(=O)O)C)Cc1ccccc1)CC(=O)O)CC(=O)N)Cc1ccc(cc1)O)CCCNC(=N)N)CC(C)C)CCCNC(=N)N
Isomeric 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)O)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(NC(=O)C(C(C)C)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(Cc1nc[nH]c1)N)CO)CC(=O)O)C)Cc1ccccc1)CC(=O)O)CC(=O)N)Cc1ccc(cc1)O)CCCNC(=N)N)CC(C)C)CCCNC(=N)N
InChI InChI=1S/C147H237N43O43S/c1-18-75(12)115(142(229)180-96(56-72(6)7)131(218)183-104(145(232)233)63-110(155)200)188-139(226)106(68-192)185-134(221)101(62-109(154)199)177-130(217)95(55-71(4)5)174-132(219)97(58-81-37-41-84(195)42-38-81)175-125(212)88(33-23-26-49-149)167-123(210)89(34-24-27-50-150)171-140(227)113(73(8)9)186-118(205)76(13)164-121(208)93(47-53-234-17)170-127(214)92(45-46-107(152)197)169-122(209)87(32-22-25-48-148)166-124(211)90(35-28-51-161-146(156)157)168-129(216)94(54-70(2)3)173-126(213)91(36-29-52-162-147(158)159)172-143(230)116(78(15)193)189-136(223)98(59-82-39-43-85(196)44-40-82)176-133(220)100(61-108(153)198)178-135(222)103(65-112(203)204)182-144(231)117(79(16)194)190-137(224)99(57-80-30-20-19-21-31-80)181-141(228)114(74(10)11)187-119(206)77(14)165-128(215)102(64-111(201)202)179-138(225)105(67-191)184-120(207)86(151)60-83-66-160-69-163-83/h19-21,30-31,37-44,66,69-79,86-106,113-117,191-196H,18,22-29,32-36,45-65,67-68,148-151H2,1-17H3,(H2,152,197)(H2,153,198)(H2,154,199)(H2,155,200)(H,160,163)(H,164,208)(H,165,215)(H,166,211)(H,167,210)(H,168,216)(H,169,209)(H,170,214)(H,171,227)(H,172,230)(H,173,213)(H,174,219)(H,175,212)(H,176,220)(H,177,217)(H,178,222)(H,179,225)(H,180,229)(H,181,228)(H,182,231)(H,183,218)(H,184,207)(H,185,221)(H,186,205)(H,187,206)(H,188,226)(H,189,223)(H,190,224)(H,201,202)(H,203,204)(H,232,233)(H4,156,157,161)(H4,158,159,162)
InChI Key VBUWHHLIZKOSMS-UHFFFAOYSA-N
Natural/Endogenous Targets
Target
PAC1 receptor
secretin receptor
VPAC1 receptor
VPAC2 receptor
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
VPAC1 receptor Ligand is endogenous in the given species Hs Agonist Agonist 8.5 – 9.8 pKi - 5,13-14,16-18
⤷ pKi 9.8 (Ki 1.6x10-10 M) [17]
Description: inhibition of [125I]-VIP binding to membranes from HEK293 cells stably expressing the recombinant receptor
pKi 9.7 (Ki 2x10-10 M) [17]
Description: cyclic AMP formation in CHO cells stably expressing recombinant receptor
pKi 9.7 (Ki 2x10-10 M) [17]
Description: cyclic AMP formation in HEK293 cells stably expressing recombinant receptor
pKi 9.1 (Ki 8x10-10 M) [16]
Description: inhibition of [125I]-VIP binding to membranes from COS cells transiently expressing the recombinant receptor
pKi 9.1 (Ki 8.2x10-10 M) [17]
Description: inhibition of [125I]-VIP binding to membranes from CHO cells stably expressing the recombinant receptor
pKi 9.0 (Ki 9x10-10 M) [14]
Description: inhibition of [125I]-VIP binding to membranes from CHO cells stably expressing the recombinant receptor
pKi 9.0 (Ki 9x10-10 M) [5]
Description: inhibition of [125I]-VIP binding to membranes from CHO cells stably expressing the recombinant receptor
pKi 8.9 (Ki 1.4x10-9 M) [13]
Description: inhibition of [125I]-VIP binding to membranes from COS cells transiently expressing the recombinant receptor
pKi 8.5 (Ki 3.4x10-9 M) [18]
Description: inhibition of [125I]-VIP binding to CHO cells stably expressing the recombinant receptor
VPAC2 receptor Ligand is endogenous in the given species Hs Agonist Agonist 7.8 – 8.8 pKi - 13-14,18
⤷ pKi 8.8 (Ki 1.7x10-9 M) [14]
Description: inhibition of [125I]-VIP binding to membranes from CHO cells stably expressing the recombinant receptor
pKi 8.7 (Ki 1.8x10-9 M) [13]
Description: inhibition of [125I]-VIP binding to membranes from COS cells transiently expressing the recombinant receptor
pKi 7.8 (Ki 1.6x10-8 M) [18]
Description: inhibition of [125I]-VIP binding to CHO cells stably expressing the recombinant receptor
PAC1 receptor Ligand is endogenous in the given species Hs Agonist Agonist <6.0 – 8.4 pKi - 3
⤷ pKi 8.4 (Ki 4.4x10-9 M) [3]
Description: inhibition of [125I]-PACAP-27 binding to membranes from HEK293 cells stably expressing the PAC1 short receptor (ENST00000409363)
pKi 6.3 (Ki 4.58x10-7 M) [3]
Description: inhibition of [125I]-PACAP-27 binding to membranes from HEK293 cells stably expressing the full length receptor (ENST00000304166)
pKi <6.0 (Ki >1x10-6 M) [3]
Description: inhibition of [125I]-PACAP-27 binding to membranes from HEK293 cells stably expressing the PAC1 very short receptor
PAC1 receptor Ligand is endogenous in the given species Rn Agonist Agonist 5.5 – 5.8 pKi - 2
⤷ pKi 5.8 (Ki 1.5x10-6 M) [2]
Description: inhibition of [125I]-[Ac-His1]PACAP-27 binding to membranes from CHO cells stably expressing the rat PAC1 receptor isoform including the hop1 exon
pKi 5.5 (Ki 3.5x10-6 M) [2]
Description: inhibition of [125I]-[Ac-His1]PACAP-27 binding to membranes from CHO cells stably expressing the rat PAC1 receptor isoform including the hop1 exon
VPAC1 receptor Ligand is endogenous in the given species Hs Agonist Agonist 7.9 – 10.0 pEC50 - 4,10-11,14,18
⤷ pEC50 10.0 (EC50 1.1x10-10 M) [4]
Description: cyclic AMP formation in CHO cells stably expressing recombinant receptor
pEC50 9.4 (EC50 4x10-10 M) [14]
Description: stimulation of cyclic AMP formation in CHO cells stably expressing the recombinant receptor
pEC50 9.3 (EC50 5x10-10 M) [10]
Description: cyclic AMP formation in CHO cells stably expressing recombinant receptor
pEC50 8.9 (EC50 1.2x10-9 M) [18]
Description: stimulation of cyclic AMP formation in CHO cells stably expressing the recombinant receptor
pEC50 8.5 (EC50 3x10-9 M) [11]
Description: stimulation of cyclic AMP formation in CHO cells stably expressing the recombinant receptor
pEC50 7.9 (EC50 1.41x10-8 M) [4]
Description: calcium influx in CHO cells stably expressing recombinant receptor
VPAC2 receptor Ligand is endogenous in the given species Hs Agonist Agonist 7.3 – 9.3 pEC50 - 4,10-11,14,18
⤷ pEC50 9.3 (EC50 5x10-10 M) [14]
Description: stimulation of cyclic AMP formation in CHO cells stably expressing the recombinant receptor
pEC50 9.2 (EC50 6.3x10-10 M) [4]
Description: cyclic AMP formation in CHO cells stably expressing recombinant receptor
pEC50 8.5 (EC50 3x10-9 M) [11]
Description: stimulation of cyclic AMP formation in CHO cells stably expressing the recombinant receptor
pEC50 7.9 (EC50 1.4x10-8 M) [18]
Description: stimulation of cyclic AMP formation in CHO cells stably expressing the recombinant receptor
pEC50 7.8 (EC50 1.5x10-8 M) [10]
Description: cyclic AMP formation in CHO cells stably expressing recombinant receptor
pEC50 7.3 (EC50 5.09x10-8 M) [4]
Description: calcium influx in CHO cells stably expressing recombinant receptor
PAC1 receptor Ligand is endogenous in the given species Hs Agonist Agonist <6.0 – 8.7 pEC50 - 3-4,11
⤷ pEC50 8.7 (EC50 2.1x10-9 M) [3]
Description: stimulation of cyclic AMP formation in HEK293 cells stably expressing the PAC1 short receptor (ENST00000409363)
pEC50 7.8 (EC50 1.51x10-8 M) [4]
Description: cyclic AMP formation in CHO cells stably expressing recombinant receptor
pEC50 6.7 (EC50 1.86x10-7 M) [3]
Description: stimulation of cyclic AMP formation in HEK293 cells stably expressing the full length receptor (ENST00000304166)
pEC50 6.4 (EC50 3.89x10-7 M) [4]
Description: calcium influx in CHO cells stably expressing recombinant receptor
pEC50 6.4 (EC50 3.73x10-7 M) [3]
Description: stimulation of cyclic AMP formation in HEK293 cells stably expressing the PAC1 very short receptor
pEC50 <6.0 (EC50 >1x10-6 M) [11]
Description: stimulation of cyclic AMP formation in NIH/3T3 cells stably expressing the recombinant receptor
PAC1 receptor Ligand is endogenous in the given species Rn Agonist Agonist 7.1 pEC50 - 2
⤷ pEC50 7.1 (EC50 8x10-8 M) [2]
Description: stimulation of adenylate cyclase in CHO cells stably expressing the rat PAC1 receptor isoform lacking the hip and hop exons
pEC50 7.1 (EC50 8x10-8 M) [2]
Description: stimulation of adenylate cyclase in CHO cells stably expressing the rat PAC1 receptor isoform including the hop1 exon
VPAC1 receptor Ligand is endogenous in the given species Rn Agonist Agonist 8.7 – 9.0 pIC50 - 6-8
⤷ pIC50 9.0 (IC50 1x10-9 M) [7]
Description: inhibition of [125I]-VIP binding to membranes from CHO cells stably expressing the recombinant receptor
pIC50 8.7 (IC50 2x10-9 M) [6]
Description: inhibition of [125I]-VIP binding to membranes from CHO cells stably expressing the recombinant receptor
pIC50 8.7 (IC50 2x10-9 M) [8]
Description: Inhibition of [125I]VIP binding in membranes from CHO cells expressing recombinant receptor
VPAC1 receptor Ligand is endogenous in the given species Hs Agonist Agonist 8.0 – 9.3 pIC50 - 6-8,10-11
⤷ pIC50 9.3 (IC50 5x10-10 M) [10]
Description: inhibition of [125I]-VIP binding to membranes from CHO cells stably expressing the recombinant receptor
pIC50 8.7 (IC50 2x10-9 M) [6]
Description: inhibition of [125I]-VIP binding to membranes from CHO cells stably expressing the recombinant receptor
pIC50 8.7 (IC50 2x10-9 M) [8]
Description: Inhibition of [125I]VIP binding in membranes from LoVo cells expressing recombinant receptor
pIC50 8.7 (IC50 2x10-9 M) [7]
Description: inhibition of [125I]-VIP binding to membranes from CHO cells stably expressing the recombinant receptor
pIC50 8.0 (IC50 1x10-8 M) [11]
Description: inhibition of [125I]-VIP binding to membranes from CHO cells stably expressing the recombinant receptor
VPAC2 receptor Ligand is endogenous in the given species Rn Agonist Agonist 8.0 – 8.4 pIC50 - 6-8
⤷ pIC50 8.4 (IC50 4x10-9 M) [8]
Description: Inhibition of [125I]VIP binding in membranes from CHO cells expressing recombinant receptor
pIC50 8.4 (IC50 4x10-9 M) [7]
Description: inhibition of [125I]Ro25 1553 binding to membranes from CHO cells stably expressing the recombinant receptor
pIC50 8.0 (IC50 1x10-8 M) [6]
Description: inhibition of [125I]Ro25 1553 binding to membranes from CHO cells stably expressing the recombinant receptor
VPAC2 receptor Ligand is endogenous in the given species Hs Agonist Agonist 7.7 – 8.5 pIC50 - 6-8,10-11
⤷ pIC50 8.5 (IC50 3x10-9 M) [7]
Description: inhibition of [125I]Ro25 1553 binding to membranes from CHO cells stably expressing the recombinant receptor
pIC50 8.5 (IC50 3x10-9 M) [10]
Description: inhibition of [125I]Ro25 1553 binding to membranes from CHO cells stably expressing the recombinant receptor
pIC50 8.3 (IC50 5x10-9 M) [8]
Description: Inhibition of [125I]VIP binding in membranes from CHO cells expressing recombinant receptor
pIC50 8.0 (IC50 1x10-8 M) [6]
Description: inhibition of [125I]Ro25 1553 binding to membranes from CHO cells stably expressing the recombinant receptor
pIC50 7.7 (IC50 2x10-8 M) [11]
Description: inhibition of [125I]-VIP binding to membranes from CHO cells stably expressing the recombinant receptor
secretin receptor Ligand is endogenous in the given species Rn Agonist Agonist 6.2 pIC50 - 8
⤷ pIC50 6.2 (IC50 6x10-7 M) [8]
Description: Inhibition of [125I]Tyr25 secretin binding in membranes from CHO cells expressing recombinant receptor
PAC1 receptor Ligand is endogenous in the given species Hs Agonist Agonist <6.0 pIC50 - 11
⤷ pIC50 <6.0 (IC50 >1x10-6 M) [11]
Description: inhibition of [125I]-PACAP-27 binding to membranes from NIH/3T3 cells stably expressing the recombinant receptor
PAC1 receptor Ligand is endogenous in the given species Rn Agonist Agonist 5.7 pIC50 - 8
⤷ pIC50 5.7 (IC50 2x10-6 M) [8]
Description: Inhibition of [125I]-Ac-His1-PACAP-27 binding in membranes from CHO cells expressing recombinant receptor
secretin receptor Ligand is endogenous in the given species Hs Agonist Partial agonist 5.4 pIC50 - 9
⤷ pIC50 5.4 [9]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Potency order of endogenous ligands at PAC1 receptor PACAP-27 (ADCYAP1, P18509), PACAP-38 (ADCYAP1, P18509) >> VIP (VIP, P01282)
Potency order of endogenous ligands at VPAC2 receptor VIP (VIP, P01282), PACAP-38 (ADCYAP1, P18509), PACAP-27 (ADCYAP1, P18509) > PHI >> GHRH (GHRH, P01286), secretin (SCT, P09683)
Potency order of endogenous ligands at VPAC1 receptor VIP (VIP, P01282), PACAP-27 (ADCYAP1, P18509), PACAP-38 (ADCYAP1, P18509) >> GHRH (GHRH, P01286), PHI, secretin (SCT, P09683)
Ligand mentioned in the following text fields
VIP and PACAP receptors overview