You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
Name(2S)-2-[(3aR,4R,7S,7aS)-1,3-dioxooctahydro-2H-4,7-methanoisoindol-2-yl]propanoic acid
Accession NumberDB07823
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: 237.2518
Monoisotopic: 237.100107973
Chemical FormulaC12H15NO4
InChI KeyInChIKey=REFMTLIXGKZVDF-VRGHQRLXSA-N
InChI
InChI=1S/C12H15NO4/c1-5(12(16)17)13-10(14)8-6-2-3-7(4-6)9(8)11(13)15/h5-9H,2-4H2,1H3,(H,16,17)/t5-,6-,7+,8-,9+/m0/s1
IUPAC Name
(2S)-2-[(1R,2R,6S,7S)-3,5-dioxo-4-azatricyclo[5.2.1.0²,⁶]decan-4-yl]propanoic acid
SMILES
[H][C@@](C)(N1C(=O)[C@@]2([H])[C@@]3([H])CC[C@]([H])(C3)[C@@]2([H])C1=O)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoindoles and derivatives
Sub ClassIsoindolines
Direct ParentIsoindolones
Alternative Parents
Substituents
  • Norbornane monoterpenoid
  • Monoterpenoid
  • Isoindolone
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Dicarboximide
  • N-alkylpyrrolidine
  • 2-pyrrolidone
  • Pyrrolidone
  • Carboxylic acid imide, n-substituted
  • Pyrrolidine
  • Carboxylic acid imide
  • Tertiary amine
  • Lactam
  • Carboxamide group
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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+0.9712
Blood Brain Barrier+0.926
Caco-2 permeable+0.5
P-glycoprotein substrateNon-substrate0.7552
P-glycoprotein inhibitor INon-inhibitor0.9634
P-glycoprotein inhibitor IINon-inhibitor0.9483
Renal organic cation transporterNon-inhibitor0.9022
CYP450 2C9 substrateNon-substrate0.7189
CYP450 2D6 substrateNon-substrate0.8246
CYP450 3A4 substrateNon-substrate0.5703
CYP450 1A2 substrateNon-inhibitor0.8804
CYP450 2C9 inhibitorNon-inhibitor0.9456
CYP450 2D6 inhibitorNon-inhibitor0.9606
CYP450 2C19 inhibitorNon-inhibitor0.9442
CYP450 3A4 inhibitorNon-inhibitor0.9749
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9856
Ames testNon AMES toxic0.8376
CarcinogenicityNon-carcinogens0.9507
BiodegradationReady biodegradable0.5306
Rat acute toxicity1.9653 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9738
hERG inhibition (predictor II)Non-inhibitor0.9814
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 Solubility13.4 mg/mLALOGPS
logP0.56ALOGPS
logP0.45ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.72ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.68 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity57 m3·mol-1ChemAxon
Polarizability23.11 Å3ChemAxon
Number of Rings3ChemAxon
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
Escherichia coli
Pharmacological action
unknown
General Function:
Beta-lactamase activity
Specific Function:
Not Available
Gene Name:
blaCTX-M-9a
Uniprot ID:
Q9L5C8
Molecular Weight:
30951.03 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 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Beta-lactamase activity
Specific Function:
This protein is a serine beta-lactamase with a substrate specificity for cephalosporins.
Gene Name:
ampC
Uniprot ID:
P00811
Molecular Weight:
41555.3 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 ]
Comments
comments powered by Disqus
Drug created on September 15, 2010 15:26 / Updated on September 16, 2013 18:07