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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Benitez R, Delgado-Maroto V, Caro M, Forte-Lago I, Duran-Prado M, O'Valle F, Lichtman AH, Gonzalez-Rey E, Delgado M. (2018)
Vasoactive Intestinal Peptide Ameliorates Acute Myocarditis and Atherosclerosis by Regulating Inflammatory and Autoimmune Responses.
J Immunol, 200 (11): 3697-3710. [PMID:29669783]
2. Ciccarelli E, Svoboda M, De Neef P, Di Paolo E, Bollen A, Dubeaux C, Vilardaga JP, Waelbroeck M, Robberecht P. (1995)
Pharmacological properties of two recombinant splice variants of the PACAP type I receptor, transfected and stably expressed in CHO cells.
Eur J Pharmacol, 288 (3): 259-67. [PMID:7774670]
3. Dautzenberg FM, Mevenkamp G, Wille S, Hauger RL. (1999)
N-terminal splice variants of the type I PACAP receptor: isolation, characterization and ligand binding/selectivity determinants.
J Neuroendocrinol, 11 (12): 941-9. [PMID:10583729]
4. Dickson L, Aramori I, McCulloch J, Sharkey J, Finlayson K. (2006)
A systematic comparison of intracellular cyclic AMP and calcium signalling highlights complexities in human VPAC/PAC receptor pharmacology.
Neuropharmacology, 51 (6): 1086-98. [PMID:16930633]
5. Gaudin P, Couvineau A, Maoret JJ, Rouyer-Fessard C, Laburthe M. (1996)
Stable expression of the recombinant human VIP1 receptor in clonal Chinese hamster ovary cells: pharmacological, functional and molecular properties.
Eur J Pharmacol, 302 (1-3): 207-14. [PMID:8791009]
6. Gourlet P, Rathé J, De Neef P, Cnudde J, Vandermeers-Piret MC, Waelbroeck M, Robberecht P. (1998)
Interaction of lipophilic VIP derivatives with recombinant VIP1/PACAP and VIP2/PACAP receptors.
Eur J Pharmacol, 354 (1): 105-11. [PMID:9726637]
7. Gourlet P, Vandermeers A, Van Rampelbergh J, De Neef P, Cnudde J, Waelbroeck M, Robberecht P. (1998)
Analogues of VIP, helodermin, and PACAP discriminate between rat and human VIP1 and VIP2 receptors.
Ann N Y Acad Sci, 865: 247-52. [PMID:9928018]
8. Gourlet P, Vandermeers A, Vertongen P, Rathe J, De Neef P, Cnudde J, Waelbroeck M, Robberecht P. (1997)
Development of high affinity selective VIP1 receptor agonists.
Peptides, 18 (10): 1539-45. [PMID:9437714]
9. Ishihara T, Nakamura S, Kaziro Y, Takahashi T, Takahashi K, Nagata S. (1991)
Molecular cloning and expression of a cDNA encoding the secretin receptor.
EMBO J, 10 (7): 1635-41. [PMID:1646711]
10. Juarranz MG, Van Rampelbergh J, Gourlet P, De Neef P, Cnudde J, Robberecht P, Waelbroeck M. (1999)
Different vasoactive intestinal polypeptide receptor domains are involved in the selective recognition of two VPAC(2)-selective ligands.
Mol Pharmacol, 56 (6): 1280-7. [PMID:10570056]
11. Moody TW, Jensen RT, Fridkin M, Gozes I. (2002)
(N-stearyl, norleucine17)VIPhybrid is a broad spectrum vasoactive intestinal peptide receptor antagonist.
J Mol Neurosci, 18 (1-2): 29-35. [PMID:11931347]
12. Mutt V, Said SI. (1974)
Structure of the porcine vasoactive intestinal octacosapeptide. The amino-acid sequence. Use of kallikrein in its determination.
Eur J Biochem, 42 (2): 581-9. [PMID:4829446]
13. Nicole P, Du K, Couvineau A, Laburthe M. (1998)
Site-directed mutagenesis of human vasoactive intestinal peptide receptor subtypes VIP1 and VIP2: evidence for difference in the structure-function relationship.
J Pharmacol Exp Ther, 284 (2): 744-50. [PMID:9454823]
14. Nicole P, Lins L, Rouyer-Fessard C, Drouot C, Fulcrand P, Thomas A, Couvineau A, Martinez J, Brasseur R, Laburthe M. (2000)
Identification of key residues for interaction of vasoactive intestinal peptide with human VPAC1 and VPAC2 receptors and development of a highly selective VPAC1 receptor agonist. Alanine scanning and molecular modeling of the peptide.
J Biol Chem, 275 (31): 24003-12. [PMID:10801840]
15. Said SI, Mutt V. (1972)
Isolation from porcine-intestinal wall of a vasoactive octacosapeptide related to secretin and to glucagon.
Eur J Biochem, 28 (2): 199-204. [PMID:5069712]
16. Sreedharan SP, Patel DR, Huang JX, Goetzl EJ. (1993)
Cloning and functional expression of a human neuroendocrine vasoactive intestinal peptide receptor.
Biochem Biophys Res Commun, 193: 546-553. [PMID:8390245]
17. Sreedharan SP, Patel DR, Xia M, Ichikawa S, Goetzl EJ. (1994)
Human vasoactive intestinal peptide1 receptors expressed by stable transfectants couple to two distinct signaling pathways.
Biochem Biophys Res Commun, 203 (1): 141-8. [PMID:8074647]
18. Xia M, Sreedharan SP, Bolin DR, Gaufo GO, Goetzl EJ. (1997)
Novel cyclic peptide agonist of high potency and selectivity for the type II vasoactive intestinal peptide receptor.
J Pharmacol Exp Ther, 281 (2): 629-33. [PMID:9152366]