NAV

gamma-Glutamyl[S-(2-iodobenzyl)cysteinyl]glycine

Identification

Generic Name
gamma-Glutamyl[S-(2-iodobenzyl)cysteinyl]glycine
DrugBank Accession Number
DB03597
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 523.343
Monoisotopic: 523.027399561
Chemical Formula
C17H22IN3O6S
Synonyms
Not Available
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UcGMP-specific 3',5'-cyclic phosphodiesteraseNot AvailableHumans
UGlutathione S-transferase Mu 4Not AvailableHumans
UHigh affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9ANot AvailableHumans
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

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
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-amino acid / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid / Amino acid or derivatives / Aromatic homomonocyclic compound / Aryl halide / Aryl iodide
show 34 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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)carbamoyl]-2-{[(2-iodophenyl)methyl]sulfanyl}ethyl]carbamoyl}butanoic acid
SMILES
[H]N([H])[C@@H](CCC(=O)N([H])[C@@H](CSCC1=CC=CC=C1I)C(=O)N([H])CC(O)=O)C(O)=O

References

General References
Not Available
PubChem Compound
447108
PubChem Substance
46508001
ChemSpider
394293
ZINC
ZINC000014880825
PDBe Ligand
IBG
PDB Entries
1gul / 1m9b

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.0301 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
Polarizability45.41 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/MSsplash10-0zmi-0065950000-8d19ca58d3aa77bf9913
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xr-6786690000-8a594a4886bed4d982e5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-002r-6169600000-680c3f98694196ffde8e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-006x-0950000000-656c8444f778f88c77ae
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-9351100000-e958451328a9a4a37f28
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004l-5920000000-92bd54139eb3c3b8f2b8
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-192.33272
predicted
DeepCCS 1.0 (2019)
[M+H]+194.72829
predicted
DeepCCS 1.0 (2019)
[M+Na]+200.66673
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. cGMP-specific 3',5'-cyclic phosphodiesterase
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
Details2. Glutathione S-transferase Mu 4
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
Details3. High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A
Kind
Protein
Organism
Humans
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 at June 13, 2005 13:24 / Updated at June 12, 2020 16:52