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Identification
NameGamma-Glutamyl[S-(2-Iodobenzyl)Cysteinyl]Glycine
Accession NumberDB03597  (EXPT01826)
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: 523.343
Monoisotopic: 523.027399561
Chemical FormulaC17H22IN3O6S
InChI KeyQFYJAEOZTBVJQM-QWHCGFSZSA-N
InChI
InChI=1S/C17H22IN3O6S/c18-11-4-2-1-3-10(11)8-28-9-13(16(25)20-7-15(23)24)21-14(22)6-5-12(19)17(26)27/h1-4,12-13H,5-9,19H2,(H,20,25)(H,21,22)(H,23,24)(H,26,27)/t12-,13+/m0/s1
IUPAC Name
(2S)-2-amino-4-{[(1S)-1-[(carboxymethyl)carbamoyl]-2-{[(2-iodophenyl)methyl]sulfanyl}ethyl]carbamoyl}butanoic acid
SMILES
N[C@@H](CCC(=O)N[[email protected]](CSCC1=CC=CC=C1I)C(=O)NCC(O)=O)C(O)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
cGMP-specific 3',5'-cyclic phosphodiesteraseProteinunknownNot AvailableHumanO76074 details
Glutathione S-transferase Mu 4ProteinunknownNot AvailableHumanQ03013 details
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9AProteinunknownNot AvailableHumanO76083 details
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
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6477
Blood Brain Barrier+0.5703
Caco-2 permeable-0.6873
P-glycoprotein substrateSubstrate0.6078
P-glycoprotein inhibitor INon-inhibitor0.8553
P-glycoprotein inhibitor IINon-inhibitor0.9971
Renal organic cation transporterNon-inhibitor0.9061
CYP450 2C9 substrateNon-substrate0.8845
CYP450 2D6 substrateNon-substrate0.8275
CYP450 3A4 substrateNon-substrate0.7087
CYP450 1A2 substrateNon-inhibitor0.8745
CYP450 2C9 inhibitorNon-inhibitor0.9058
CYP450 2D6 inhibitorNon-inhibitor0.8246
CYP450 2C19 inhibitorNon-inhibitor0.7892
CYP450 3A4 inhibitorNon-inhibitor0.8853
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.963
Ames testNon AMES toxic0.5956
CarcinogenicityNon-carcinogens0.9401
BiodegradationNot ready biodegradable0.9885
Rat acute toxicity2.2538 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.97
hERG inhibition (predictor II)Non-inhibitor0.8032
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 Solubility0.0301 mg/mLALOGPS
logP-2.4ALOGPS
logP-2ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)1.81ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area158.82 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity111.79 m3·mol-1ChemAxon
Polarizability45.46 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gamma-glutamyl peptides. These are oligo- and polypeptides consisting of any C-terminal alpha peptide having a gamma-glutamyl residue attached at the N alpha-position.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma-glutamyl peptides
Alternative Parents
Substituents
  • Gamma-glutamyl alpha peptide
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • L-alpha-amino acid
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid
  • Iodobenzene
  • Halobenzene
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • N-acyl-amine
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Aryl iodide
  • Aryl halide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organoiodide
  • Organohalogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Metal ion binding
Specific Function:
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP (PubMed:9714779, PubMed:15489334). Specifically regulates nitric-oxide-generated cGMP (PubMed:15489334).
Gene Name:
PDE5A
Uniprot ID:
O76074
Molecular Weight:
99984.14 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein homodimerization activity
Specific Function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Active on 1-chloro-2,4-dinitrobenzene.
Gene Name:
GSTM4
Uniprot ID:
Q03013
Molecular Weight:
25561.095 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Metal ion binding
Specific Function:
Specifically hydrolyzes the second messenger cGMP, which is a key regulator of many important physiological processes. Highly specific: compared to other members of the cyclic nucleotide phosphodiesterase family, has the highest affinity and selectivity for cGMP (PubMed:9624146, PubMed:18757755, PubMed:21483814). Specifically regulates natriuretic-peptide-dependent cGMP signaling in heart, acti...
Gene Name:
PDE9A
Uniprot ID:
O76083
Molecular Weight:
68491.95 Da
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23