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

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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.

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/)
Immunopharmacology Comments
In addition to its vascular and cardioprotective functions, VIP also regulates immune function and inflammatory responses. In a mouse model of autoimmune myocarditis, admninistration of VIP reduced signs of heart damage and reduced myocardial inflammatory infiltration and levels of myocardial autoantibodies [1]. In an atherosclerosis model, the anti-inflammatory effects of VIP included a reduction in Th1-driven inflammatory responses and an elevation in regulatory T cell numbers in atherosclerotic arteries and their draining lymph nodes. Together these findings suggest that VIP may be a valid therapeutic option for the treatment of heart inflammation and atherosclerosis.