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Identification
NameN-({(1R)-1-carboxy-2-[(4-fluorobenzyl)sulfanyl]ethyl}carbamoyl)-L-glutamic acid
Accession NumberDB07754
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: 402.395
Monoisotopic: 402.089699867
Chemical FormulaC16H19FN2O7S
InChI KeyInChIKey=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][C@@](CCC(O)=O)(NC(=O)N[C@@]([H])(CSCC1=CC=C(F)C=C1)C(O)=O)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-carbamoyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an carbamoyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-carbamoyl-alpha amino acids
Alternative Parents
Substituents
  • N-carbamoyl-alpha-amino acid
  • S-alkyl-l-cysteine
  • Tricarboxylic acid or derivatives
  • Halobenzene
  • Fluorobenzene
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl fluoride
  • Urea
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
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
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot 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 folate. In the brain, modulates excitatory neurotransmission through the hydrolysis of the neuropeptide, N-aceylaspartylglutamate (NAAG), thereby releasing glutamate. Isoform PSM-4 and isoform PSM-5 would...
Gene Name:
FOLH1
Uniprot ID:
Q04609
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 ]
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Drug created on September 15, 2010 15:25 / Updated on September 16, 2013 18:07