NAV

7-((Carboxy(4-Hydroxyphenyl)Acetyl)Amino)-7-Methoxy-(3-((1-Methyl-1h-Tetrazol-5-Yl)Thio)Methyl)-8-Oxo-5-Oxa-1-Azabicyclo[4.2.0]Oct-2-Ene-2-Carboxylic Acid

Identification

Generic Name
7-((Carboxy(4-Hydroxyphenyl)Acetyl)Amino)-7-Methoxy-(3-((1-Methyl-1h-Tetrazol-5-Yl)Thio)Methyl)-8-Oxo-5-Oxa-1-Azabicyclo[4.2.0]Oct-2-Ene-2-Carboxylic Acid
DrugBank Accession Number
DB04342
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 520.473
Monoisotopic: 520.101246958
Chemical Formula
C20H20N6O9S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBeta-lactamase OXA-10Not AvailablePseudomonas aeruginosa
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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-acyl-alpha amino acids and derivatives
Alternative Parents
Phenylacetamides / Oxacephems / 1-hydroxy-2-unsubstituted benzenoids / Alkylarylthioethers / 1,3-dicarbonyl compounds / Dicarboxylic acids and derivatives / Tetrazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Secondary carboxylic acid amides
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Substituents
1,3-dicarbonyl compound / 1-hydroxy-2-unsubstituted benzenoid / Alkylarylthioether / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Azetidine / Azole / Benzenoid / Beta-lactam
show 26 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
JWCSIUVGFCSJCK-LIUKBUMOSA-N
InChI
InChI=1S/C20H20N6O9S/c1-25-19(22-23-24-25)36-8-10-7-35-18-20(34-2,17(33)26(18)13(10)16(31)32)21-14(28)12(15(29)30)9-3-5-11(27)6-4-9/h3-6,12,18,27H,7-8H2,1-2H3,(H,21,28)(H,29,30)(H,31,32)/t12-,18-,20+/m1/s1
IUPAC Name
(6R,7R)-7-[(2R)-2-carboxy-2-(4-hydroxyphenyl)acetamido]-7-methoxy-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
CO[C@]1(NC(=O)[C@H](C(O)=O)C2=CC=C(O)C=C2)[C@H]2OCC(CSC3=NN=NN3C)=C(N2C1=O)C(O)=O

References

General References
Not Available
PubChem Compound
5488645
PubChem Substance
46505636
ChemSpider
4589914
ChEBI
94604
ZINC
ZINC000003831157
PDBe Ligand
MXL

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 Solubility0.751 mg/mLALOGPS
logP0.22ALOGPS
logP0.17Chemaxon
logS-2.8ALOGPS
pKa (Strongest Acidic)2.81Chemaxon
pKa (Strongest Basic)-1.7Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area206.3 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity133.7 m3·mol-1Chemaxon
Polarizability47.29 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9253
Blood Brain Barrier-0.9914
Caco-2 permeable-0.7721
P-glycoprotein substrateSubstrate0.7268
P-glycoprotein inhibitor INon-inhibitor0.7989
P-glycoprotein inhibitor IIInhibitor0.5
Renal organic cation transporterNon-inhibitor0.8587
CYP450 2C9 substrateNon-substrate0.7914
CYP450 2D6 substrateNon-substrate0.8291
CYP450 3A4 substrateSubstrate0.5676
CYP450 1A2 substrateNon-inhibitor0.8075
CYP450 2C9 inhibitorNon-inhibitor0.7409
CYP450 2D6 inhibitorNon-inhibitor0.8614
CYP450 2C19 inhibitorNon-inhibitor0.7233
CYP450 3A4 inhibitorInhibitor0.5245
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.684
Ames testNon AMES toxic0.6673
CarcinogenicityNon-carcinogens0.9182
BiodegradationNot ready biodegradable0.9144
Rat acute toxicity2.2482 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9759
hERG inhibition (predictor II)Non-inhibitor0.5569
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/MSsplash10-0udi-0100090000-d98ec19b1036e66b1c93
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0901330000-9e37280d3cfaa60c20f8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0259320000-b59a5254608d0f99908c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-7900000000-b5b475a9fd748c10cd3c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0aou-5941000000-e0c2ee687f0e8820a099
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01sa-1913700000-c946b52e5d675f2448e5
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-205.88928
predicted
DeepCCS 1.0 (2019)
[M+H]+208.28485
predicted
DeepCCS 1.0 (2019)
[M+Na]+214.19737
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Beta-lactamase OXA-10
Kind
Protein
Organism
Pseudomonas aeruginosa
Pharmacological action
Unknown
General Function
Penicillin binding
Specific Function
Hydrolyzes both carbenicillin and oxacillin.
Gene Name
bla
Uniprot ID
P14489
Uniprot Name
Beta-lactamase OXA-10
Molecular Weight
29506.575 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