(2S)-2-[(3aR,4R,7S,7aS)-1,3-dioxooctahydro-2H-4,7-methanoisoindol-2-yl]propanoic acid

Identification

Name
(2S)-2-[(3aR,4R,7S,7aS)-1,3-dioxooctahydro-2H-4,7-methanoisoindol-2-yl]propanoic acid
Accession Number
DB07823
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 237.2518
Monoisotopic: 237.100107973
Chemical Formula
C12H15NO4
InChI Key
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][[email protected]@](C)(N1C(=O)[[email protected]@]2([H])[[email protected]@]3([H])CC[[email protected]]([H])(C3)[[email protected]@]2([H])C1=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UBeta-lactamaseNot AvailableEscherichia coli
UBeta-lactamaseNot AvailableEscherichia coli (strain K12)
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
1933963
PubChem Substance
99444294
ChemSpider
1482883
HET
GF1
PDB Entries
3g31 / 3gsg

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 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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 alanine and derivatives. These are compounds containing alanine or a derivative thereof resulting from reaction of alanine 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
Alanine and derivatives
Alternative Parents
Monoterpenoids / Isoindolones / Pyrrolidine-2-ones / N-substituted carboxylic acid imides / N-alkylpyrrolidines / Dicarboximides / Lactams / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds
show 5 more
Substituents
Alanine or derivatives / Isoindolone / Norbornane monoterpenoid / Monoterpenoid / Isoindoline / Isoindole or derivatives / N-alkylpyrrolidine / 2-pyrrolidone / Pyrrolidone / Carboxylic acid imide, n-substituted
show 17 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not 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
Uniprot Name
Beta-lactamase
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
Uniprot Name
Beta-lactamase
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]

Drug created on September 15, 2010 15:26 / Updated on December 01, 2017 15:56