orexin-B   Click here for help

GtoPdb Ligand ID: 1699

Synonyms: hypocretin-2 | orexin b
Compound class: Endogenous peptide in human, mouse or rat
Comment: A alternative structure for this ligand is represented by CID 56947114.
Additional labelled orexin-B probes that are useful experimental tools include [13C6]- and [15N]-radiolabelled peptides [6].
Species: Human
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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 CSCCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=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)NCC(=O)NC(C(=O)NC(C(=O)NCC(=O)N1CCCC1C(=O)N1CCCC1C(=O)NCC(=O)NC(C(=O)NC(C(=O)N)CCCN=C(N)N)CO)CC(C)C)CCC(=O)N)CCCN=C(N)N)CC(C)C)CCC(=O)N)CCCN=C(N)N)CC(C)C)CC(C)C)CCC(=O)N)C)CO)CC(=O)N)Cc1nc[nH]c1)C)C)C(CC)C)CC(C)C)C(O)C)N
Isomeric SMILES CSCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=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)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N)CCCN=C(N)N)CO)CC(C)C)CCC(=O)N)CCCN=C(N)N)CC(C)C)CCC(=O)N)CCCN=C(N)N)CC(C)C)CC(C)C)CCC(=O)N)C)CO)CC(=O)N)Cc1nc[nH]c1)C)C)[C@H](CC)C)CC(C)C)[C@H](O)C)N
InChI InChI=1S/C123H212N44O35S/c1-18-63(12)96(164-114(196)80(46-62(10)11)163-119(201)97(67(16)170)165-102(184)69(124)35-41-203-17)118(200)143-50-91(175)146-64(13)99(181)147-65(14)101(183)157-81(47-68-49-136-57-145-68)113(195)162-82(48-90(128)174)105(187)141-52-93(177)150-83(55-168)115(197)148-66(15)100(182)153-74(30-33-88(126)172)108(190)160-79(45-61(8)9)112(194)161-78(44-60(6)7)111(193)155-72(26-21-38-139-123(134)135)106(188)156-75(31-34-89(127)173)109(191)159-77(43-59(4)5)110(192)154-71(25-20-37-138-122(132)133)103(185)140-51-92(176)149-73(29-32-87(125)171)107(189)158-76(42-58(2)3)104(186)144-54-95(179)166-39-23-28-86(166)120(202)167-40-22-27-85(167)117(199)142-53-94(178)151-84(56-169)116(198)152-70(98(129)180)24-19-36-137-121(130)131/h49,57-67,69-86,96-97,168-170H,18-48,50-56,124H2,1-17H3,(H2,125,171)(H2,126,172)(H2,127,173)(H2,128,174)(H2,129,180)(H,136,145)(H,140,185)(H,141,187)(H,142,199)(H,143,200)(H,144,186)(H,146,175)(H,147,181)(H,148,197)(H,149,176)(H,150,177)(H,151,178)(H,152,198)(H,153,182)(H,154,192)(H,155,193)(H,156,188)(H,157,183)(H,158,189)(H,159,191)(H,160,190)(H,161,194)(H,162,195)(H,163,201)(H,164,196)(H,165,184)(H4,130,131,137)(H4,132,133,138)(H4,134,135,139)/t63-,64-,65-,66-,67+,69-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,96-,97-/m0/s1
InChI Key OHOWSYIKESXDMN-WMQZXSDYSA-N
References
1. Ammoun S, Holmqvist T, Shariatmadari R, Oonk HB, Detheux M, Parmentier M, Akerman KE, Kukkonen JP. (2003)
Distinct recognition of OX1 and OX2 receptors by orexin peptides.
J Pharmacol Exp Ther, 305 (2): 507-14. [PMID:12606634]
2. Hoang QV, Bajic D, Yanagisawa M, Nakajima S, Nakajima Y. (2003)
Effects of orexin (hypocretin) on GIRK channels.
J Neurophysiol, 90 (2): 693-702. [PMID:12702704]
3. Holmqvist T, Akerman KE, Kukkonen JP. (2002)
Orexin signaling in recombinant neuron-like cells.
FEBS Lett, 526 (1-3): 11-4. [PMID:12208495]
4. Johansson L, Ekholm ME, Kukkonen JP. (2008)
Multiple phospholipase activation by OX(1) orexin/hypocretin receptors.
Cell Mol Life Sci, 65 (12): 1948-56. [PMID:18488139]
5. Langmead CJ, Jerman JC, Brough SJ, Scott C, Porter RA, Herdon HJ. (2004)
Characterisation of the binding of [3H]-SB-674042, a novel nonpeptide antagonist, to the human orexin-1 receptor.
Br J Pharmacol, 141 (2): 340-6. [PMID:14691055]
6. Lindström M, Schinkelshoek M, Tienari PJ, Kukkonen JP, Renkonen R, Fronczek R, Lammers GJ, Itkonen O. (2021)
Orexin-A measurement in narcolepsy: A stability study and a comparison of LC-MS/MS and immunoassays.
Clin Biochem, 90: 34-39. [PMID:33539807]
7. Okumura T, Takeuchi S, Motomura W, Yamada H, Egashira Si S, Asahi S, Kanatani A, Ihara M, Kohgo Y. (2001)
Requirement of intact disulfide bonds in orexin-A-induced stimulation of gastric acid secretion that is mediated by OX1 receptor activation.
Biochem Biophys Res Commun, 280 (4): 976-81. [PMID:11162621]
8. Putula J, Turunen PM, Jäntti MH, Ekholm ME, Kukkonen JP. (2011)
Agonist ligand discrimination by the two orexin receptors depends on the expression system.
Neurosci Lett, 494 (1): 57-60. [PMID:21362456]
9. Sakurai T, Amemiya A, Ishii M, Matsuzaki I, Chemelli RM, Tanaka H, Williams SC, Richardson JA, Kozlowski GP, Wilson S et al.. (1998)
Orexins and orexin receptors: a family of hypothalamic neuropeptides and G protein-coupled receptors that regulate feeding behavior.
Cell, 92 (4): 573-85. [PMID:9491897]
10. Smart D, Jerman JC, Brough SJ, Rushton SL, Murdock PR, Jewitt F, Elshourbagy NA, Ellis CE, Middlemiss DN, Brown F. (1999)
Characterization of recombinant human orexin receptor pharmacology in a Chinese hamster ovary cell-line using FLIPR.
Br J Pharmacol, 128 (1): 1-3. [PMID:10498827]
11. Tang J, Chen J, Ramanjaneya M, Punn A, Conner AC, Randeva HS. (2008)
The signalling profile of recombinant human orexin-2 receptor.
Cell Signal, 20 (9): 1651-61. [PMID:18599270]
12. Turunen PM, Ekholm ME, Somerharju P, Kukkonen JP. (2010)
Arachidonic acid release mediated by OX1 orexin receptors.
Br J Pharmacol, 159 (1): 212-21. [PMID:20002100]