TP508   Click here for help

GtoPdb Ligand ID: 9284

Synonyms: Chrysalin
Compound class: Peptide
Comment: TP508 is a synthetic 23 amino acid peptide corresponding to amino acids 183 to 205 of the endogenous wound healing molecule human thrombin [8]. TP508 has been investigated as an activator of soft and hard tissue repair [1,4-5,7,9], and for its potential to mitigate tissue damage caused by radiation exposure [3,6]. TP508 may also provide an alternative to stem cell therapy in regenerative medicine.
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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.

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)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NCC(=O)NCC(=O)N1CCCC1C(=O)NC(C(=O)NC(C(=O)O)C(C)C)Cc1ccccc1)CO)CC(=O)O)CCC(=O)O)CS)C)CC(=O)O)CCCN=C(N)N)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C1CCCN1C(=O)C(NC(=O)C(Cc1ccc(cc1)O)NC(=O)CNC(=O)C(N)C)CCCCN)CC(=O)O)CCC(=O)O
Isomeric SMILES CC(C)[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H]1CCCN1C(=O)CNC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(=O)O)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CS)NC(=O)[C@H](C)NC(=O)[C@H](CC(=O)O)NC(=O)CNC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)CNC(=O)[C@H](C)N)C(=O)O
InChI InChI=1S/C97H146N28O36S/c1-48(2)79(96(160)161)123-91(155)60(35-51-15-6-5-7-16-51)119-93(157)66-20-13-33-124(66)73(133)45-104-68(128)40-106-85(149)64(46-126)121-89(153)62(38-77(140)141)114-72(132)44-109-84(148)57(27-29-75(136)137)117-92(156)65(47-162)122-81(145)50(4)110-87(151)61(37-76(138)139)113-71(131)43-107-82(146)54(19-12-32-103-97(101)102)115-86(150)55(17-8-10-30-98)111-69(129)42-108-83(147)56(26-28-74(134)135)116-90(154)63(39-78(142)143)120-94(158)67-21-14-34-125(67)95(159)58(18-9-11-31-99)118-88(152)59(36-52-22-24-53(127)25-23-52)112-70(130)41-105-80(144)49(3)100/h5-7,15-16,22-25,48-50,54-67,79,126-127,162H,8-14,17-21,26-47,98-100H2,1-4H3,(H,104,128)(H,105,144)(H,106,149)(H,107,146)(H,108,147)(H,109,148)(H,110,151)(H,111,129)(H,112,130)(H,113,131)(H,114,132)(H,115,150)(H,116,154)(H,117,156)(H,118,152)(H,119,157)(H,120,158)(H,121,153)(H,122,145)(H,123,155)(H,134,135)(H,136,137)(H,138,139)(H,140,141)(H,142,143)(H,160,161)(H4,101,102,103)/t49-,50-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,79-/m0/s1
InChI Key MOZAQZCGIKWACU-VKDININFSA-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. Derkach DN, Wadekar SA, Perkins KB, Rousseau E, Dreiza CM, Cheung-Flynn J, Ramos HC, Ugarova TP, Sheller MR. (2010)
RGD-dependent binding of TP508 to integrin alphavbeta3 mediates cell adhesion and induction of nitric oxide.
Thromb Haemost, 104 (1): 172-82. [PMID:20508901]
2. Fife C, Mader JT, Stone J, Brill L, Satterfield K, Norfleet A, Zwernemann A, Ryaby JT, Carney DH. (2007)
Thrombin peptide Chrysalin stimulates healing of diabetic foot ulcers in a placebo-controlled phase I/II study.
Wound Repair Regen, 15 (1): 23-34. [PMID:17244316]
3. Kantara C, Moya SM, Houchen CW, Umar S, Ullrich RL, Singh P, Carney DH. (2015)
Novel regenerative peptide TP508 mitigates radiation-induced gastrointestinal damage by activating stem cells and preserving crypt integrity.
Lab Invest, 95 (11): 1222-33. [PMID:26280221]
4. Li X, Wang H, Touma E, Qi Y, Rousseau E, Quigg RJ, Ryaby JT. (2007)
TP508 accelerates fracture repair by promoting cell growth over cell death.
Biochem Biophys Res Commun, 364 (1): 187-93. [PMID:17942078]
5. Olszewska-Pazdrak B, Carney DH. (2013)
Systemic administration of thrombin peptide TP508 enhances VEGF-stimulated angiogenesis and attenuates effects of chronic hypoxia.
J Vasc Res, 50 (3): 186-96. [PMID:23594718]
6. Olszewska-Pazdrak B, McVicar SD, Rayavara K, Moya SM, Kantara C, Gammarano C, Olszewska P, Fuller GM, Sower LE, Carney DH. (2016)
Nuclear Countermeasure Activity of TP508 Linked to Restoration of Endothelial Function and Acceleration of DNA Repair.
Radiat Res, 186 (2): 162-174. [PMID:27388041]
7. Ryaby JT, Sheller MR, Levine BP, Bramlet DG, Ladd AL, Carney DH. (2006)
Thrombin peptide TP508 stimulates cellular events leading to angiogenesis, revascularization, and repair of dermal and musculoskeletal tissues.
J Bone Joint Surg Am, 88 Suppl 3: 132-9. [PMID:17079379]
8. Tsopanoglou NE, Papaconstantinou ME, Flordellis CS, Maragoudakis ME. (2004)
On the mode of action of thrombin-induced angiogenesis: thrombin peptide, TP508, mediates effects in endothelial cells via alphavbeta3 integrin.
Thromb Haemost, 92 (4): 846-57. [PMID:15467917]
9. Vartanian KB, Chen HY, Kennedy J, Beck SK, Ryaby JT, Wang H, Hoying JB. (2006)
The non-proteolytically active thrombin peptide TP508 stimulates angiogenic sprouting.
J Cell Physiol, 206 (1): 175-80. [PMID:16021627]
10. Wang H, Li X, Tomin E, Doty SB, Lane JM, Carney DH, Ryaby JT. (2005)
Thrombin peptide (TP508) promotes fracture repair by up-regulating inflammatory mediators, early growth factors, and increasing angiogenesis.
J Orthop Res, 23 (3): 671-9. [PMID:15885490]