CyclicPepedia Knowledge Base
Eptifibatide
Basic information
| CPKB ID | CP00304 |
| IUPAC Name | 2-[(3S,6S,12S,20R,23S)-20-carbamoyl-12-[4-(diaminomethylideneamino)butyl]-3-(1H-indol-3-ylmethyl)-2,5,8,11,14,22-hexaoxo-17,18-dithia-1,4,7,10,13,21-hexazabicyclo[21.3.0]hexacosan-6-yl]acetic acid |
| Synonyms |
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| Source |
Synthetic construct [Division : Synthetic]
Wikipedia: Synthetic construct PubChem |
| Function | |
| Information |
Eptifibatide is a synthetic homodetic cyclic peptide comprising N(alpha)-(3-sulfanylpropanoyl)homoarginyl, glycyl, aspartyl, tryptophyl, prolyl and cysteinamide residues connected in sequence and cyclised via a disulfide bond. Derived from a protein found in the venom of the southeastern pygmy rattlesnake, Sistrurus miliarus barbouri, eptifibatide is an anti-coagulant that inhibits platelet aggregation by selectively blocking the platelet glycoprotein IIb/IIIa receptor, so preventing the binding of fibrinogen, von Willebrand factor, and other adhesive ligands. It is used in the management of unstable angina and in patients undergoing coronary angioplasty and stenting procedures. It has a role as a platelet aggregation inhibitor and an anticoagulant. It is an organic disulfide, a macrocycle and a homodetic cyclic peptide. |
Legend
Structure
| Molecular Formula |
C35H49N11O9S2 |
| Molecular Weight | 831.3156141 g/mol |
| SMILES | N=C(N)NCCCC[C@@H]1NC(=O)CCSSC[C@@H](C(N)=O)NC(=O)[C@@H]2CCCN2C(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](CC(=O)O)NC(=O)CNC1=O |
| InChI | InChI=1S/C35H49N11O9S2/c36-30(51)25-18-57-56-13-10-27(47)42-22(8-3-4-11-39-35(37)38)31(52)41-17-28(48)43-23(15-29(49)50)32(53)44-24(14-19-16-40-21-7-2-1-6-20(19)21)34(55)46-12-5-9-26(46)33(54)45-25/h1-2,6-7,16,22-26,40H,3-5,8-15,17-18H2,(H2,36,51)(H,41,52)(H,42,47)(H,43,48)(H,44,53)(H,45,54)(H,49,50)(H4,37,38,39)/t22-,23-,24-,25-,26-/m0/s1 |
| InChIKey | CZKPOZZJODAYPZ-CWXWOLIANA-N |
|
2D Structure
PubChem|448812
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Sequence
| One-letter code |
CXGDWPC |
| IUPAC Condensed | deamino-Cys(1)-hArg-Gly-Asp-Trp-Pro-Cys(1)-NH2 |
| Amino acid chain | deamino--Cys(1)--hArg--Gly--Asp--Trp--Pro--Cys-NH2(1) |
| Graph representation | deamino,Cys,hArg,Gly,Asp,Trp,Pro,Cys-NH2 @1,7 |
| One letter code from Structure | KGDWPC |
| Amino acid chain from Structure | Lys(1)--Gly--Asp--Trp--Pro--CO(1) |
| Description of the conversion sequence | The one letter code and Amino acid chain derived from the structural transformation may be inconsistent, with the Amino acid chain containing Essential Amino acid and the one letter code not. |
| svg Image |
Structure Properties
| Property Name | Property Value | |
|---|---|---|
| Exact Mass | 831.3156141 | |
| Number of Rings | 4.0 | |
| Complexity | 0.912280702 | |
| XlogP3 AA | -1.84473 | |
| Heavy Atom Count | 57.0 | |
| Hydrogen Bond Donor Count | 11.0 | |
| Hydrogen Bond Acceptor Count | 11.0 | |
| Rotatable Bond Count | 10.0 |
| Property Name | Property Value | |
|---|---|---|
| Formal Charge | 0.0 | |
| Refractivity | 212.2182 | |
| Rule_of_Five | 0.0 | |
| Number of Atoms | 57.0 | |
| Topological Polar Surface Area | 323.89 | |
| Refractivity | 212.2182 | |
| Veber Rule | 0.0 | |
| Ghose Filter | 0.0 |
| Property Name | Property Value | |
|---|---|---|
| RDKit Fingerprint |
11000111110100100111110011111000011000100111110000111011101001001110101101101110111111000110110011110101110101001010011001110111000001011001111000001111000100000100001010011011100111011111100110110000101001001000000110000101010100000101001110001110011101101111000110001110000110101111110000000010011011010111001001010001110100000011111111111110101100010010111100001001001011000010100000101010010101000110100100001111000010110101101000110111110011100000111100010010111000011000000100000110001011010111100100101110111100011110110111011101000110001101101011010110101000101100010111000100000110111100101110110001001010011010100000111101110000101100100110110111011011000110111110111111010111011101011100010000101101000000010111110011101101111110101010110010001110101011101110011010000111111001011010011011001101011011100100101101111010110000011011111001100001110111011101110011000110000101111000010011000101100110111100110100011100111110110000011111001000011001110101010000011001010110001001110001110101000101000000111001111111110111110110001110110001001011000101001000101001100011100011001001110110000101001001111010000001101001000111101101110110010100101011011000101110110110100111001001010011111110111011000001110001001101110010100110011111010111001010011001111111000110101110101010000001111101110101001001011010111101100111110110101001001011111111010001011110110111110010110001011101001111001000000011000001001100000011100101101011001000000011111110101001001011001110111100111101110001110000111011011010010000100100100111111011110101011000110100111111110100100111101000100100100111001011010111100010000011100110001011011010100010110110110100000000110010010010011011001011000110001011100101000000110000111110000100100101000111010110101000100000100011011001011100111110010110100010001000100001111010000011110001111111101100100111111000111111100111111010000001100001010000111111101010010100001101101110011100101101000011011001010111011110001111110110100011011001011111011000001011101101100111000001111100110110001000000001101110010100100000111001000011 |
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| Morgan Fingerprint |
0000110000100000000100000000100000000000000000000000010000000000100000000000000010000000001000000000000000000000000100010000000010000000000010000001000000000000100000000000000100000000000000000000010000000000000000000000000000000001000000000000000000000000000000000000000000000000000000001000000000000100000000000010000000000100100001100000100000000000000111000010100000000000000000000000010000000000001000000000000000000000000100000001000010000010000000001010000000100000001000100000000000000000000000010001000000000000000000000000000000000000000001010010000000000000000000000000000100000000100000001000000000000000000000010000000000100000000000000010000000000000010100000001000000001000000000000000000000000000011000000010001000000000000000000000000000000011000000000000000000000000000001000000000000001011000100000000000000001000100000000110000001001001000000000000000000000000000000010000011100010000000000000110000000000010000000010000000000000000001000000000000000000000000000010000000000000010000010100000000000010000 |
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| MACCS Keys |
00000000000000100000000001000000000010000001000000000110000000000101000000000111001111001011100111001100111000110000011111111101110110001111101100111011011111110111110 |
Sequence Properties
| Property Name | Property Value | |
|---|---|---|
| Boman Index | 0.412857142857142 | |
| Instability | -5.05714285714285 | |
| Charge | -1.12551864830296 |
Binding Target
Detail
Uniprot: P05106
Kind: Protein>Membrane protein
Organism: Homo sapiens(Human)
Evidevce: DrugBank
Sequence: MRARPRPRPLWATVLALGALAGVGVGGPNICTTRGVSSCQQCLAVSPMCAWCSDEALPLGSPRCDLKENLLKDNCAPESIEFPVSEARVLEDRPLSDKGSGDSSQVTQVSPQRIALRLRPDDSKNFSIQVRQVEDYPVDIYYLMDLSYSMKDDLWSIQNLGTKLATQMRKLTSNLRIGFGAFVDKPVSPYMYISPPEALENPCYDMKTTCLPMFGYKHVLTLTDQVTRFNEEVKKQSVSRNRDAPEGGFDAIMQATVCDEKIGWRNDASHLLVFTTDAKTHIALDGRLAGIVQPNDGQCHVGSDNHYSASTTMDYPSLGLMTEKLSQKNINLIFAVTENVVNLYQNYSELIPGTTVGVLSMDSSNVLQLIVDAYGKIRSKVELEVRDLPEELSLSFNATCLNNEVIPGLKSCMGLKIGDTVSFSIEAKVRGCPQEKEKSFTIKPVGFKDSLIVQVTFDCDCACQAQAEPNSHRCNNGNGTFECGVCRCGPGWLGSQCECSEEDYRPSQQDECSPREGQPVCSQRGECLCGQCVCHSSDFGKITGKYCECDDFSCVRYKGEMCSGHGQCSCGDCLCDSDWTGYYCNCTTRTDTCMSSNGLLCSGRGKCECGSCVCIQPGSYGDTCEKCPTCPDACTFKKECVECKKFDRGALHDENTCNRYCRDEIESVKELKDTGKDAVNCTYKNEDDCVVRFQYYEDSSGKSILYVVEEPECPKGPDILVVLLSVMGAILLIGLAALLIWKLLITIHDRKEFAKFEEERARAKWDTANNPLYKEATSTFTNITYRGT
General Function:
Virus receptor activity
Specific Function:
Integrin alpha-V/beta-3 (ITGAV:ITGB3) is a receptor for cytotactin, fibronectin, laminin, matrix metalloproteinase-2, osteopontin, osteomodulin, prothrombin, thrombospondin, vitronectin and von Willebrand factor. Integrin alpha-IIb/beta-3 (ITGA2B:ITGB3) is a receptor for fibronectin, fibrinogen, plasminogen, prothrombin, thrombospondin and vitronectin. Integrins alpha-IIb/beta-3 and alpha-V/beta-3 recognize the sequence R-G-D in a wide array of ligands. Integrin alpha-IIb/beta-3 recognizes the sequence H-H-L-G-G-G-A-K-Q-A-G-D-V in fibrinogen gamma chain. Following activation integrin alpha-IIb/beta-3 brings about platelet/platelet interaction through binding of soluble fibrinogen. This step leads to rapid platelet aggregation which physically plugs ruptured endothelial surface. Fibrinogen binding enhances SELP expression in activated platelets (By similarity).(Microbial infection) Integrin ITGAV:ITGB3 acts as a receptor for herpes virus 8/HHV-8 (PubMed:18045938). Integrin ITGAV:ITGB3 acts as a receptor for coxsackievirus A9 (PubMed:7519807). Acts as a receptor for Hantaan virus (PubMed:9618541). Integrin ITGAV:ITGB3 acts as a receptor for cytomegalovirus/HHV-5 (PubMed:15834425). Integrin ITGA5:ITGB3 acts as a receptor for human metapneumovirus (PubMed:24478423). Integrin ITGAV:ITGB3 acts aP05556s a receptor for human parechovirus 1 (PubMed:11160695). Integrin ITGAV:ITGB3 acts as a receptor for west nile virus (PubMed:23658209). In case of HIV-1 infection, the interaction with extracellular viral Tat protein seems to enhance angiogenesis in Kaposi's sarcoma lesions (PubMed:10397733).
Additional database information: TTD[Integrin beta-3]
Detail
Uniprot: A0A024R8I1
Kind: Protein group>Membrane protein
Organism: Homo sapiens(Human)
Evidevce: DrugBank
Sequence: MRARPRPRPLWATVLALGALAGVGVGGPNICTTRGVSSCQQCLAVSPMCAWCSDEALPLGSPRCDLKENLLKDNCAPESIEFPVSEARVLEDRPLSDKGSGDSSQVTQVSPQRIALRLRPDDSKNFSIQVRQVEDYPVDIYYLMDLSYSMKDDLWSIQNLGTKLATQMRKLTSNLRIGFGAFVDKPVSPYMYISPPEALENPCYDMKTTCLPMFGYKHVLTLTDQVTRFNEEVKKQSVSRNRDAPEGGFDAIMQATVCDEKIGWRNDASHLLVFTTDAKTHIALDGRLAGIVQPNDGQCHVGSDNHYSASTTMDYPSLGLMTEKLSQKNINLIFAVTENVVNLYQNYSELIPGTTVGVLSMDSSNVLQLIVDAYGKIRSKVELEVRDLPEELSLSFNATCLNNEVIPGLKSCMGLKIGDTVSFSIEAKVRGCPQEKEKSFTIKPVGFKDSLIVQVTFDCDCACQAQAEPNSHRCNNGNGTFECGVCRCGPGWLGSQCECSEEDYRPSQQDECSPREGQPVCSQRGECLCGQCVCHSSDFGKITGKYCECDDFSCVRYKGEMCSGHGQCSCGDCLCDSDWTGYYCNCTTRTDTCMSSNGLLCSGRGKCECGSCVCIQPGSYGDTCEKCPTCPDACTFKKECVECKKFDRGALHDENTCNRYCRDEIESVKELKDTGKDAVNCTYKNEDDCVVRFQYYEDSSGKSILYVVEEPECPKGPDILVVLLSVMGAILLIGLAALLIWKLLITIHDRKEFAKFEEERARAKWDTANNPLYKEATSTFTNITYRGT
General Function:
Voltage-gated calcium channel activity
Specific Function:
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1B gives rise to N-type calcium currents.
Additional database information: TTD[Voltage-dependent N-type calcium channel]
Biologic Description
Drug Indication PubChem|448812
For treatment of myocardial infarction and acute coronary syndrome.
Pharmacology PubChem|448812
Eptifibatide is an anti-coagulant that selectively and reversibly blocks the platelet glycoprotein IIb/IIIa receptor.
Toxicity PubChem|448812
Eptifibatide was not lethal to rats, rabbits, or monkeys when administered by continuous intravenous infusion for 90 minutes at a total dose of 45 mg/kg (about 2 to 5 times the recommended maximum daily human dose on a body surface area basis)
Metabolism PubChem|448812
No major metabolites have been detected in human plasma. Deamidated eptifibatide and other, more polar metabolites have been detected in urine.
Manufacturers
| Manufacturers Name | Value | |
|---|---|---|
| CreativePeptides | ||
| Bayer healthcare pharmaceuticals | ||
| Upsher smith laboratories | ||
| Merck |
| Manufacturers Name | Value | |
|---|---|---|
| Apotex | ||
| Baxter Healthcare Corp | ||
| Pharmasources | ||
| Novartis | ||
| AstraZeneca |
Forecasting tools
| Forecasting tools | Value | |
|---|---|---|
| Structure to Sequence | ||
| Structure Properties | ||
| Sequence to Structure | ||
| Sequence Properties | ||
| Expasy ProtParam Tool | CXGDWPC | |
| SEA | RUN SEA Predictions |
Information Source
| Property Name | Property ID | |
|---|---|---|
| Patents | CZKPOZZJODAYPZ-CWXWOLIANA-N | |
| pubchem | 448812 | |
| Drugbank | DB00063 | |
| DRAMP3 | ||
| Uniprot | ||
| Cybase | ||
| CONOSERVER | ||
| BindingDB | BDBM50092098 | |
| CHEMBL | CHEMBL1174 | |
| CTD | D000077542 | |
| Wikipedia | Eptifibatide | |
| KEGG Compound/Drug | ||
| CHEBI | CHEBI:291902 | |
| EPA DSSTox | DTXSID7046673 | |
| FDA Global Substance Registration System (GSRS) | NA8320J834 | |
| DTP/NCI | ||
| Chemspider | CZKPOZZJODAYPZ-CWXWOLIANA-N |
Reference
| Pubmed_ID | Title | DOI | Journal | |
|---|---|---|---|---|
3254038 |
None |
Yao Xue Xue Bao |
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Studies of chemical constituents of Manis pentadactylaAbstract
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