PACAP-27   Click here for help

GtoPdb Ligand ID: 2257

Synonyms: pituitary adenylate cyclase activating polypeptide-27
Compound class: Endogenous peptide in human, mouse or rat
Comment: Sequences of human, mouse, rat and sheep PACAP-27 are identical. As is often the case with peptide molecules, representations of the stereochemistry of PACAP-27 may vary across different resources.
Species: Human, Mouse, Rat, Sheep
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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
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)N)CC(C)C)C(C)C)C)C)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(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(C(O)C)NC(=O)C(NC(=O)C(C(CC)C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(Cc1[nH]cnc1)N)CO)CC(=O)O)Cc1ccccc1)CC(=O)O)CO)Cc1ccc(cc1)O)CO)CCCNC(=N)N)Cc1ccc(cc1)O)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)N)CC(C)C)C(C)C)C)C)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(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(C(O)C)NC(=O)C(NC(=O)C(C(CC)C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(Cc1[nH]cnc1)N)CO)CC(=O)O)Cc1ccccc1)CC(=O)O)CO)Cc1ccc(cc1)O)CO)CCCNC(=N)N)Cc1ccc(cc1)O)CCCNC(=N)N
InChI InChI=1S/C142H224N40O39S/c1-16-75(10)113(179-108(191)66-156-120(201)102(63-109(192)193)173-135(216)104(67-183)176-119(200)88(146)62-84-65-153-70-157-84)139(220)174-101(58-80-28-18-17-19-29-80)133(214)182-114(79(14)186)140(221)175-103(64-110(194)195)132(213)178-106(69-185)136(217)172-100(61-83-39-45-87(189)46-40-83)131(212)177-105(68-184)134(215)164-93(34-27-54-155-142(151)152)126(207)170-98(59-81-35-41-85(187)42-36-81)129(210)163-92(33-26-53-154-141(149)150)124(205)161-89(30-20-23-50-143)122(203)165-94(47-48-107(147)190)127(208)166-95(49-55-222-15)121(202)159-78(13)118(199)180-111(73(6)7)137(218)167-91(32-22-25-52-145)123(204)162-90(31-21-24-51-144)125(206)171-99(60-82-37-43-86(188)44-38-82)130(211)169-97(57-72(4)5)128(209)160-76(11)116(197)158-77(12)117(198)181-112(74(8)9)138(219)168-96(115(148)196)56-71(2)3/h17-19,28-29,35-46,65,70-79,88-106,111-114,183-189H,16,20-27,30-34,47-64,66-69,143-146H2,1-15H3,(H2,147,190)(H2,148,196)(H,153,157)(H,156,201)(H,158,197)(H,159,202)(H,160,209)(H,161,205)(H,162,204)(H,163,210)(H,164,215)(H,165,203)(H,166,208)(H,167,218)(H,168,219)(H,169,211)(H,170,207)(H,171,206)(H,172,217)(H,173,216)(H,174,220)(H,175,221)(H,176,200)(H,177,212)(H,178,213)(H,179,191)(H,180,199)(H,181,198)(H,182,214)(H,192,193)(H,194,195)(H4,149,150,154)(H4,151,152,155)
InChI Key RZGBUJXSKLDAFE-UHFFFAOYSA-N
Natural/Endogenous Targets
Target
PAC1 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 8.9 pKi - 4
⤷ pKi 8.9 (Ki 1.3x10-9 M) [4]
Description: inhibition of [125I]-VIP binding to membranes from CHO cells stably expressing the recombinant receptor
PAC1 receptor Ligand is endogenous in the given species Rn Agonist Agonist 8.5 – 8.8 pKi - 1
⤷ pKi 8.8 (Ki 1.5x10-9 M) [1]
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 8.5 (Ki 3x10-9 M) [1]
Description: inhibition of [125I]-[Ac-His1]PACAP-27 binding to membranes from CHO cells stably expressing the rat PAC1 receptor isoform lacking the hip and hop exons
PAC1 receptor Ligand is endogenous in the given species Hs Agonist Agonist 6.9 – 8.5 pKi - 2
⤷ pKi 8.5 (Ki 2.9x10-9 M) [2]
Description: inhibition of [125I]-PACAP-27 binding to membranes from HEK293 cells stably expressing the full length receptor (ENST00000304166)
pKi 8.5 (Ki 3.1x10-9 M) [2]
Description: inhibition of [125I]-PACAP-27 binding to membranes from HEK293 cells stably expressing the PAC1 short receptor (ENST00000409363)
pKi 6.9 (Ki 1.29x10-7 M) [2]
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 10.0 – 10.1 pEC50 - 1
⤷ pEC50 10.1 (EC50 8x10-11 M) [1]
Description: stimulation of adenylate cyclase in CHO cells stably expressing the rat PAC1 receptor isoform lacking the hip and hop exons
pEC50 10.0 (EC50 1x10-10 M) [1]
Description: stimulation of adenylate cyclase in CHO cells stably expressing the rat PAC1 receptor isoform including the hop1 exon
PAC1 receptor Ligand is endogenous in the given species Hs Agonist Agonist 7.4 – 10.6 pEC50 - 2-3,6
⤷ pEC50 10.6 (EC50 2.6x10-11 M) [3]
Description: cyclic AMP formation in CHO cells stably expressing recombinant receptor
pEC50 9.1 (EC50 8x10-10 M) [2]
Description: stimulation of cyclic AMP formation in HEK293 cells stably expressing the full length receptor (ENST00000304166)
pEC50 9.0 (EC50 1x10-9 M) [2]
Description: stimulation of cyclic AMP formation in HEK293 cells stably expressing the PAC1 short receptor (ENST00000409363)
pEC50 8.7 (EC50 2x10-9 M) [6]
Description: stimulation of cyclic AMP formation in NIH/3T3 cells stably expressing the recombinant receptor
pEC50 8.5 (EC50 3.3x10-9 M) [3]
Description: calcium influx in CHO cells stably expressing recombinant receptor
pEC50 7.4 (EC50 3.7x10-8 M) [2]
Description: stimulation of cyclic AMP formation in HEK293 cells stably expressing the PAC1 very short receptor
VPAC1 receptor Ligand is endogenous in the given species Hs Agonist Agonist 7.6 – 9.9 pEC50 - 3,6
⤷ pEC50 9.9 (EC50 1.3x10-10 M) [3]
Description: cyclic AMP formation in CHO cells stably expressing recombinant receptor
pEC50 8.2 (EC50 6x10-9 M) [6]
Description: stimulation of cyclic AMP formation in CHO cells stably expressing the recombinant receptor
pEC50 7.6 (EC50 2.26x10-8 M) [3]
Description: calcium influx in CHO cells stably expressing recombinant receptor
VPAC2 receptor Ligand is endogenous in the given species Hs Agonist Agonist 7.6 – 9.4 pEC50 - 3,6
⤷ pEC50 9.4 (EC50 3.8x10-10 M) [3]
Description: cyclic AMP formation in CHO cells stably expressing recombinant receptor
pEC50 8.4 (EC50 4x10-9 M) [6]
Description: stimulation of cyclic AMP formation in CHO cells stably expressing the recombinant receptor
pEC50 7.6 (EC50 2.39x10-8 M) [3]
Description: calcium influx in CHO cells stably expressing recombinant receptor
VPAC1 receptor Ligand is endogenous in the given species Rn Agonist Agonist 9.0 pIC50 - 5
⤷ pIC50 9.0 (IC50 1x10-9 M) [5]
Description: inhibition of [125I]-VIP binding to membranes from CHO cells stably expressing the recombinant receptor
VPAC1 receptor Ligand is endogenous in the given species Hs Agonist Agonist 7.8 – 8.5 pIC50 - 5-6
⤷ pIC50 8.5 (IC50 3x10-9 M) [5]
Description: inhibition of [125I]-VIP binding to membranes from CHO cells stably expressing the recombinant receptor
pIC50 7.8 (IC50 1.5x10-8 M) [6]
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 pIC50 - 5
⤷ pIC50 8.0 (IC50 1x10-8 M) [5]
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 7.6 – 8.0 pIC50 - 5-7
⤷ pIC50 8.0 (IC50 1x10-8 M) [5]
Description: inhibition of [125I]Ro25 1553 binding to membranes from CHO cells stably expressing the recombinant receptor
pIC50 7.7 (IC50 2.1x10-8 M) [7]
Description: inhibition of [125I]-PACAP-27 binding to membranes from CHO cells stably expressing the recombinant receptor
pIC50 7.6 (IC50 2.5x10-8 M) [6]
Description: inhibition of [125I]-VIP binding to membranes from CHO cells stably expressing the recombinant receptor
PAC1 receptor Ligand is endogenous in the given species Hs Agonist Agonist 7.6 pIC50 - 6
⤷ pIC50 7.6 (IC50 2.5x10-8 M) [6]
Description: inhibition of [125I]-PACAP-27 binding to membranes from NIH/3T3 cells stably expressing the recombinant receptor
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
VIP and PACAP receptors comments