N-({(1R)-1-carboxy-2-[(4-fluorobenzyl)sulfanyl]ethyl}carbamoyl)-L-glutamic acid

Identification

Name
N-({(1R)-1-carboxy-2-[(4-fluorobenzyl)sulfanyl]ethyl}carbamoyl)-L-glutamic acid
Accession Number
DB07754
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
40R868KZFF
CAS number
Not Available
Weight
Average: 402.395
Monoisotopic: 402.089699867
Chemical Formula
C16H19FN2O7S
InChI Key
IDTMSHGCAZPVLC-RYUDHWBXSA-N
InChI
InChI=1S/C16H19FN2O7S/c17-10-3-1-9(2-4-10)7-27-8-12(15(24)25)19-16(26)18-11(14(22)23)5-6-13(20)21/h1-4,11-12H,5-8H2,(H,20,21)(H,22,23)(H,24,25)(H2,18,19,26)/t11-,12-/m0/s1
IUPAC Name
(2S)-2-({[(1R)-1-carboxy-2-{[(4-fluorophenyl)methyl]sulfanyl}ethyl]carbamoyl}amino)pentanedioic acid
SMILES
[H][[email protected]@](CCC(O)=O)(NC(=O)N[[email protected]@]([H])(CSCC1=CC=C(F)C=C1)C(O)=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlutamate carboxypeptidase 2Not 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
25113157
PubChem Substance
99444225
ChemSpider
25059183
HET
FBD
PDB Entries
3d7d

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 Solubility0.09 mg/mLALOGPS
logP0.61ALOGPS
logP1.02ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.11ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.03 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity92.14 m3·mol-1ChemAxon
Polarizability38.08 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6452
Blood Brain Barrier+0.8431
Caco-2 permeable-0.6737
P-glycoprotein substrateSubstrate0.5476
P-glycoprotein inhibitor INon-inhibitor0.9194
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9071
CYP450 2C9 substrateNon-substrate0.732
CYP450 2D6 substrateNon-substrate0.8217
CYP450 3A4 substrateNon-substrate0.707
CYP450 1A2 substrateNon-inhibitor0.8334
CYP450 2C9 inhibitorNon-inhibitor0.7835
CYP450 2D6 inhibitorNon-inhibitor0.8847
CYP450 2C19 inhibitorNon-inhibitor0.6928
CYP450 3A4 inhibitorNon-inhibitor0.7816
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9407
Ames testNon AMES toxic0.7943
CarcinogenicityNon-carcinogens0.9544
BiodegradationNot ready biodegradable0.9559
Rat acute toxicity2.3503 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9122
hERG inhibition (predictor II)Non-inhibitor0.8714
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 glutamic acid and derivatives. These are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Glutamic acid and derivatives
Alternative Parents
N-carbamoyl-alpha amino acids / Cysteine and derivatives / Tricarboxylic acids and derivatives / Fluorobenzenes / Aryl fluorides / Ureas / Sulfenyl compounds / Dialkylthioethers / Carboxylic acids / Organopnictogen compounds
show 5 more
Substituents
Glutamic acid or derivatives / N-carbamoyl-alpha-amino acid / N-carbamoyl-alpha-amino acid or derivatives / Cysteine or derivatives / Tricarboxylic acid or derivatives / Fluorobenzene / Halobenzene / Aryl fluoride / Aryl halide / Monocyclic benzene moiety
show 19 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Tetrahydrofolyl-poly(glutamate) polymer binding
Specific Function
Has both folate hydrolase and N-acetylated-alpha-linked-acidic dipeptidase (NAALADase) activity. Has a preference for tri-alpha-glutamate peptides. In the intestine, required for the uptake of fola...
Gene Name
FOLH1
Uniprot ID
Q04609
Uniprot Name
Glutamate carboxypeptidase 2
Molecular Weight
84330.015 Da
References
  1. 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]

Drug created on September 15, 2010 15:25 / Updated on December 01, 2017 15:55