NAV

L-gamma-glutamyl-S-(naphthalen-1-ylmethyl)-L-cysteinylglycine

Identification

Generic Name
L-gamma-glutamyl-S-(naphthalen-1-ylmethyl)-L-cysteinylglycine
DrugBank Accession Number
DB03885
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 447.505
Monoisotopic: 447.146406237
Chemical Formula
C21H25N3O6S
Synonyms
  • 1-menaphthyl glutathione conjugate
  • L-gammaGlu-S-(1-Naphthylmethyl)-L-Cys-Gly-OH
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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
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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 / Naphthalenes / N-acyl amines / Dicarboxylic acids and derivatives / Secondary carboxylic acid amides
show 9 more
Substituents
Alpha-amino acid / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid / Amino acid or derivatives / Aromatic homopolycyclic compound / Benzenoid / Carbonyl group
show 28 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
IHZCIRSQSFPOLH-IRXDYDNUSA-N
InChI
InChI=1S/C21H25N3O6S/c22-16(21(29)30)8-9-18(25)24-17(20(28)23-10-19(26)27)12-31-11-14-6-3-5-13-4-1-2-7-15(13)14/h1-7,16-17H,8-12,22H2,(H,23,28)(H,24,25)(H,26,27)(H,29,30)/t16-,17-/m0/s1
IUPAC Name
(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(naphthalen-1-yl)methyl]sulfanyl}ethyl]carbamoyl}butanoic acid
SMILES
[H]N([H])[C@@H](CCC(=O)N([H])[C@@H](CSCC1=CC=CC2=CC=CC=C12)C(=O)N([H])CC(O)=O)C(O)=O

References

General References
Not Available
PubChem Compound
449471
PubChem Substance
46505686
ChemSpider
395998
ZINC
ZINC000012504001
PDBe Ligand
GGC
PDB Entries
3ljr

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
logP-1.9Chemaxon
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
Refractivity114.88 m3·mol-1Chemaxon
Polarizability46.15 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8847
Blood Brain Barrier+0.64
Caco-2 permeable-0.7654
P-glycoprotein substrateSubstrate0.723
P-glycoprotein inhibitor INon-inhibitor0.8758
P-glycoprotein inhibitor IINon-inhibitor0.9914
Renal organic cation transporterNon-inhibitor0.8692
CYP450 2C9 substrateNon-substrate0.8609
CYP450 2D6 substrateNon-substrate0.8056
CYP450 3A4 substrateNon-substrate0.6717
CYP450 1A2 substrateNon-inhibitor0.9
CYP450 2C9 inhibitorNon-inhibitor0.906
CYP450 2D6 inhibitorNon-inhibitor0.8208
CYP450 2C19 inhibitorNon-inhibitor0.8657
CYP450 3A4 inhibitorNon-inhibitor0.7273
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9622
Ames testNon AMES toxic0.5651
CarcinogenicityNon-carcinogens0.9306
BiodegradationNot ready biodegradable0.9424
Rat acute toxicity2.0967 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9703
hERG inhibition (predictor II)Non-inhibitor0.6539
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/MSsplash10-00os-0109300000-0ace7696fb89a1315fea
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-4593200000-739a2418cd92bc503a25
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f79-5359100000-260de83b89d597c40ef5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-0951000000-eb96a7887e5dd6dfed3b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-9612000000-c4dbeaa879c0d0e56df6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-6910000000-9afbfbcb0f59afd25da6
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-190.97636
predicted
DeepCCS 1.0 (2019)
[M+H]+193.37193
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.28445
predicted
DeepCCS 1.0 (2019)

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52