Eptifibatide (CHEM019165)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:52:37 UTC
Update Date2016-11-09 01:15:56 UTC
Accession NumberCHEM019165
Identification
Common NameEptifibatide
ClassSmall Molecule
DescriptionA 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.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N(6)-Amidino-N(2)-(3-mercaptopropionyl)-L-lysylglycyl-L-alpha-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide, cyclic(1-6)-disulfideChEBI
S(1),S(6)-Cyclo[N(6)-carbamimidoyl-N(2)-(3-sulfanylpropanoyl)-L-lysylglycyl-L-alpha-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide]ChEBI
N(6)-Amidino-N(2)-(3-mercaptopropionyl)-L-lysylglycyl-L-a-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide, cyclic(1-6)-disulfideGenerator
N(6)-Amidino-N(2)-(3-mercaptopropionyl)-L-lysylglycyl-L-a-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide, cyclic(1-6)-disulphideGenerator
N(6)-Amidino-N(2)-(3-mercaptopropionyl)-L-lysylglycyl-L-alpha-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide, cyclic(1-6)-disulphideGenerator
N(6)-Amidino-N(2)-(3-mercaptopropionyl)-L-lysylglycyl-L-α-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide, cyclic(1-6)-disulfideGenerator
N(6)-Amidino-N(2)-(3-mercaptopropionyl)-L-lysylglycyl-L-α-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide, cyclic(1-6)-disulphideGenerator
S(1),S(6)-Cyclo[N(6)-carbamimidoyl-N(2)-(3-sulfanylpropanoyl)-L-lysylglycyl-L-a-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide]Generator
S(1),S(6)-Cyclo[N(6)-carbamimidoyl-N(2)-(3-sulfanylpropanoyl)-L-lysylglycyl-L-α-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide]Generator
S(1),S(6)-Cyclo[N(6)-carbamimidoyl-N(2)-(3-sulphanylpropanoyl)-L-lysylglycyl-L-a-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide]Generator
S(1),S(6)-Cyclo[N(6)-carbamimidoyl-N(2)-(3-sulphanylpropanoyl)-L-lysylglycyl-L-alpha-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide]Generator
S(1),S(6)-Cyclo[N(6)-carbamimidoyl-N(2)-(3-sulphanylpropanoyl)-L-lysylglycyl-L-α-aspartyl-L-tryptophyl-L-prolyl-L-cysteinamide]Generator
IntegrelinMeSH
IntegrilinMeSH
EpifibatideMeSH
EpifibratideMeSH
Chemical FormulaC35H49N11O9S2
Average Molecular Mass831.970 g/mol
Monoisotopic Mass831.316 g/mol
CAS Registry Number188627-80-7
IUPAC Name2-[(3R,11S,17S,20S,25aS)-11-(4-carbamimidamidobutyl)-1,9,12,15,18-pentahydroxy-3-(C-hydroxycarbonimidoyl)-20-[(1H-indol-3-yl)methyl]-21-oxo-3H,4H,7H,8H,11H,14H,17H,20H,21H,23H,24H,25H,25aH-pyrrolo[2,1-g]1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-17-yl]acetic acid
Traditional Nameeptifibatide
SMILES[H][C@@]12CCCN1C(=O)[C@]([H])(CC1=CNC3=CC=CC=C13)N=C(O)[C@]([H])(CC(O)=O)N=C(O)CN=C(O)[C@]([H])(CCCCNC(N)=N)N=C(O)CCSSC[C@]([H])(N=C2O)C(O)=N
InChI IdentifierInChI=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
InChI KeyCZKPOZZJODAYPZ-LROMGURASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Hippuric acid or derivatives
  • Benzamide
  • Pyrrolo[2,3-d]pyrimidine
  • Benzoic acid or derivatives
  • Pyrrolopyrimidine
  • Benzoyl
  • Aminopyrimidine
  • Pyrimidone
  • Monocyclic benzene moiety
  • Pyrimidine
  • Substituted pyrrole
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Pyrrole
  • Vinylogous amide
  • Heteroaromatic compound
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid salt
  • Azacycle
  • Organic alkali metal salt
  • Carboxylic acid
  • Organoheterocyclic compound
  • Organic salt
  • Organic oxygen compound
  • Organic sodium salt
  • Organic nitrogen compound
  • Amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic zwitterion
  • Primary amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.098 g/LALOGPS
logP0.44ALOGPS
logP-0.46ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)2.91ChemAxon
pKa (Strongest Basic)12.03ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area342.33 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity233.38 m³·mol⁻¹ChemAxon
Polarizability83.08 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xr-3491108370-630de58d9d30d2e7f36dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2010000930-137906b30e70465cd6e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0829-9410000000-9e2af0d871f8a9f3487aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0cel-2001000920-0227fe4c5a0680753437Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-7010003910-ce5b37eb25c1d82268f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kbf-9411010000-7a8fb556bd984876a59aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEptifibatide
Chemspider IDNot Available
ChEBI ID291902
PubChem Compound ID448812
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available