You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameD-phenylalanyl-N-[(1S)-4-{[amino(iminio)methyl]amino}-1-(chloroacetyl)butyl]-L-prolinamide
Accession NumberDB06841
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 451.97
Monoisotopic: 451.222441627
Chemical FormulaC21H32ClN6O3
InChI KeyInChIKey=KWPACVJPAFGBEQ-IKGGRYGDSA-O
InChI
InChI=1S/C21H31ClN6O3/c22-13-18(29)16(8-4-10-26-21(24)25)27-19(30)17-9-5-11-28(17)20(31)15(23)12-14-6-2-1-3-7-14/h1-3,6-7,15-17H,4-5,8-13,23H2,(H,27,30)(H4,24,25,26)/p+1/t15-,16+,17+/m1/s1
IUPAC Name
[amino({[(4S)-4-{[(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-6-chloro-5-oxohexyl]amino})methylidene]azanium
SMILES
[H][C@@](N)(CC1=CC=CC=C1)C(=O)N1CCC[C@@]1([H])C(=O)N[C@@]([H])(CCCNC(N)=[NH2+])C(=O)CCl
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • Alpha-amino acid amide
  • Phenylpropylamine
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine carboxylic acid or derivatives
  • N-acylpyrrolidine
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Alpha-aminoketone
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Ketone
  • Guanidine
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboximidamide
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alkyl halide
  • Alkyl chloride
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9525
Blood Brain Barrier+0.6817
Caco-2 permeable-0.6525
P-glycoprotein substrateSubstrate0.6634
P-glycoprotein inhibitor INon-inhibitor0.8761
P-glycoprotein inhibitor IINon-inhibitor0.6459
Renal organic cation transporterInhibitor0.538
CYP450 2C9 substrateNon-substrate0.8267
CYP450 2D6 substrateNon-substrate0.7625
CYP450 3A4 substrateNon-substrate0.614
CYP450 1A2 substrateNon-inhibitor0.6999
CYP450 2C9 inhibitorNon-inhibitor0.797
CYP450 2D6 inhibitorNon-inhibitor0.8364
CYP450 2C19 inhibitorNon-inhibitor0.5079
CYP450 3A4 inhibitorNon-inhibitor0.7123
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7653
Ames testNon AMES toxic0.6233
CarcinogenicityNon-carcinogens0.8774
BiodegradationNot ready biodegradable0.6985
Rat acute toxicity2.5276 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.755
hERG inhibition (predictor II)Non-inhibitor0.6695
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.045 mg/mLALOGPS
logP0.33ALOGPS
logP-0.095ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)12.47ChemAxon
pKa (Strongest Basic)11.81ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area156.14 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity129.93 m3·mol-1ChemAxon
Polarizability46.67 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Thrombospondin receptor activity
Specific Function:
Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C. Functions in blood homeostasis, inflammation and wound healing.
Gene Name:
F2
Uniprot ID:
P00734
Molecular Weight:
70036.295 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Comments
comments powered by Disqus
Drug created on September 15, 2010 15:17 / Updated on September 16, 2013 18:04