NAV

3-(4-carbamoyl-1-carboxy-2-methylsulfonyl-buta-1,3-dienylamino)-indolizine-2-carboxylic acid

Identification

Generic Name
3-(4-carbamoyl-1-carboxy-2-methylsulfonyl-buta-1,3-dienylamino)-indolizine-2-carboxylic acid
DrugBank Accession Number
DB02876
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 377.372
Monoisotopic: 377.068155917
Chemical Formula
C16H15N3O6S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBeta-lactamaseNot AvailableEnterobacter cloacae
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
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
ARSFRLAHCNFFCE-IBXIYJDRSA-N
InChI
InChI=1S/C16H15N3O6S/c17-13(21)5-4-10(9-26(24)25)14(16(22)23)18-15-11(8-20)7-12-3-1-2-6-19(12)15/h1-8,18,26H,9H2,(H2,17,21)(H,22,23)/b5-4+,14-10-
IUPAC Name
(2Z)-2-[(2-formylindolizin-3-yl)amino]-5-(C-hydroxycarbonimidoyl)-3-(sulfonylmethyl)penta-2,4-dienoic acid
SMILES
[H]C(=C([H])C(\CS(=O)=O)=C(\NC1=C(C=O)C=C2C=CC=CN12)C(O)=O)C(O)=N

References

General References
Not Available
PubChem Compound
6399008
PubChem Substance
46505117
ChemSpider
16743959
ZINC
ZINC000150339198
PDBe Ligand
DVR
PDB Entries
1ga0

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
Water Solubility0.0409 mg/mLALOGPS
logP0.5ALOGPS
logP-2.8Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)0.47Chemaxon
pKa (Strongest Basic)11.66Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area149.03 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity108.66 m3·mol-1Chemaxon
Polarizability35.5 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7161
Blood Brain Barrier-0.6079
Caco-2 permeable-0.6433
P-glycoprotein substrateNon-substrate0.6861
P-glycoprotein inhibitor INon-inhibitor0.9296
P-glycoprotein inhibitor IINon-inhibitor0.9772
Renal organic cation transporterNon-inhibitor0.9477
CYP450 2C9 substrateNon-substrate0.7714
CYP450 2D6 substrateNon-substrate0.8168
CYP450 3A4 substrateNon-substrate0.6101
CYP450 1A2 substrateNon-inhibitor0.7512
CYP450 2C9 inhibitorNon-inhibitor0.6827
CYP450 2D6 inhibitorNon-inhibitor0.8673
CYP450 2C19 inhibitorNon-inhibitor0.751
CYP450 3A4 inhibitorNon-inhibitor0.8469
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9219
Ames testNon AMES toxic0.5939
CarcinogenicityNon-carcinogens0.8261
BiodegradationNot ready biodegradable0.7864
Rat acute toxicity2.4963 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9656
hERG inhibition (predictor II)Non-inhibitor0.8567
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/MSsplash10-03fr-0009000000-35164701c21aab1a2c0f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-0090000000-382afcd3d9aa10370773
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01qd-0093000000-a96835b08b79dbf42ee8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0159-0090000000-505a4c89cb5a8398fef9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0007-2960000000-a41e048c37ca4aaa5ec4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-9612000000-b35bd9cfb2207aaf489d
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]-180.53464
predicted
DeepCCS 1.0 (2019)
[M+H]+182.93022
predicted
DeepCCS 1.0 (2019)
[M+Na]+188.84273
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Beta-lactamase
Kind
Protein
Organism
Enterobacter cloacae
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
P05364
Uniprot Name
Beta-lactamase
Molecular Weight
41301.33 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

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