Gamma-Glutamyl[S-(2-Iodobenzyl)Cysteinyl]Glycine

Identification

Name
Gamma-Glutamyl[S-(2-Iodobenzyl)Cysteinyl]Glycine
Accession Number
DB03597  (EXPT01826)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 523.343
Monoisotopic: 523.027399561
Chemical Formula
C17H22IN3O6S
InChI Key
QFYJAEOZTBVJQM-STQMWFEESA-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-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[(2-iodophenyl)methyl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid
SMILES
[H][[email protected]](N)(CCC(O)=N[[email protected]@]([H])(CSCC1=CC=CC=C1I)C(O)=NCC(O)=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UcGMP-specific 3',5'-cyclic phosphodiesteraseNot AvailableHuman
UGlutathione S-transferase Mu 4Not AvailableHuman
UHigh affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9ANot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
447108
PubChem Substance
46508001
ChemSpider
394293
HET
IBG
PDB Entries
1m9b

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00601 mg/mLALOGPS
logP-1.2ALOGPS
logP-0.33ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area165.8 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity112.83 m3·mol-1ChemAxon
Polarizability45.76 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Gamma-glutamyl peptides / Glutamine and derivatives / N-acyl-alpha amino acids / Alpha amino acid amides / Cysteine and derivatives / L-alpha-amino acids / Iodobenzenes / N-acyl amines / Dicarboxylic acids and derivatives / Aryl iodides
show 11 more
Substituents
Alpha-oligopeptide / Gamma-glutamyl alpha peptide / Glutamine or derivatives / N-acyl-alpha amino acid or derivatives / N-acyl-alpha-amino acid / Cysteine or derivatives / Alpha-amino acid amide / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / Alpha-amino acid
show 34 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not 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, ...
Gene Name
PDE5A
Uniprot ID
O76074
Uniprot Name
cGMP-specific 3',5'-cyclic phosphodiesterase
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
Uniprot Name
Glutathione S-transferase Mu 4
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 phosphodie...
Gene Name
PDE9A
Uniprot ID
O76083
Uniprot Name
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A
Molecular Weight
68491.95 Da

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:16