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Identification
NameN-(3-Phenyl-2-Sulfanylpropanoyl)Phenylalanylalanine
Accession NumberDB02558  (EXPT02428)
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: 400.491
Monoisotopic: 400.145677956
Chemical FormulaC21H24N2O4S
InChI KeyInChIKey=CNILVMARPONFBX-JCGIZDLHSA-N
InChI
InChI=1S/C21H24N2O4S/c1-14(21(26)27)22-19(24)17(12-15-8-4-2-5-9-15)23-20(25)18(28)13-16-10-6-3-7-11-16/h2-11,14,17-18,28H,12-13H2,1H3,(H,22,24)(H,23,25)(H,26,27)/t14-,17-,18+/m0/s1
IUPAC Name
(2S)-2-[(2S)-3-phenyl-2-[(2R)-3-phenyl-2-sulfanylpropanamido]propanamido]propanoic acid
SMILES
[H][C@@](C)(NC(=O)[C@]([H])(CC1=CC=CC=C1)NC(=O)[C@]([H])(S)CC1=CC=CC=C1)C(O)=O
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
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • Phenylpropylamine
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Fatty acyl
  • Benzenoid
  • Fatty amide
  • Monocyclic benzene moiety
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Alkylthiol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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+0.8375
Blood Brain Barrier+0.7149
Caco-2 permeable-0.7859
P-glycoprotein substrateSubstrate0.5191
P-glycoprotein inhibitor INon-inhibitor0.9348
P-glycoprotein inhibitor IINon-inhibitor0.9948
Renal organic cation transporterNon-inhibitor0.9542
CYP450 2C9 substrateNon-substrate0.6699
CYP450 2D6 substrateNon-substrate0.8467
CYP450 3A4 substrateNon-substrate0.7174
CYP450 1A2 substrateNon-inhibitor0.911
CYP450 2C9 inhibitorNon-inhibitor0.8319
CYP450 2D6 inhibitorNon-inhibitor0.9297
CYP450 2C19 inhibitorNon-inhibitor0.9326
CYP450 3A4 inhibitorNon-inhibitor0.6665
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9183
Ames testNon AMES toxic0.8772
CarcinogenicityNon-carcinogens0.8499
BiodegradationNot ready biodegradable0.8921
Rat acute toxicity1.9103 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9969
hERG inhibition (predictor II)Non-inhibitor0.9599
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 Solubility0.00712 mg/mLALOGPS
logP2.94ALOGPS
logP2.81ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.85ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area95.5 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity108.8 m3·mol-1ChemAxon
Polarizability41.48 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 Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
Thermolysin-like specificity, but is almost confined on acting on polypeptides of up to 30 amino acids (PubMed:15283675, PubMed:8168535). Biologically important in the destruction of opioid peptides such as Met- and Leu-enkephalins by cleavage of a Gly-Phe bond (PubMed:17101991). Able to cleave angiotensin-1, angiotensin-2 and angiotensin 1-9 (PubMed:15283675). Involved in the degradation of at...
Gene Name:
MME
Uniprot ID:
P08473
Molecular Weight:
85513.225 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. 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 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:18