NAV

(6S)-N-[(2S,3R,6R,7R)-3-(Acetyloxymethyl)-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]octan-7-yl]-6-[(2-aminoacetyl)amino]-7-hydroxy-7-oxoheptanimidate

Identification

Generic Name
(6S)-N-[(2S,3R,6R,7R)-3-(Acetyloxymethyl)-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]octan-7-yl]-6-[(2-aminoacetyl)amino]-7-hydroxy-7-oxoheptanimidate
DrugBank Accession Number
DB04488
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 487.504
Monoisotopic: 487.149874172
Chemical Formula
C19H27N4O9S
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
UD-alanyl-D-alanine carboxypeptidaseNot AvailableStreptomyces sp. (strain R61)
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
JDAREAJBQYNCGO-UPMYTKPLSA-M
InChI
InChI=1S/C19H28N4O9S/c1-9(24)32-7-10-8-33-17-14(16(27)23(17)15(10)19(30)31)22-12(25)5-3-2-4-11(18(28)29)21-13(26)6-20/h10-11,14-15,17H,2-8,20H2,1H3,(H,21,26)(H,22,25)(H,28,29)(H,30,31)/p-1/t10-,11+,14-,15+,17-/m1/s1
IUPAC Name
(Z,6S)-N-[(2S,3R,6R,7R)-3-[(acetyloxy)methyl]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]octan-7-yl]-6-(2-aminoacetamido)-6-carboxyhexanimidate
SMILES
[H][C@]12SC[C@@H](COC(C)=O)[C@H](N1C(=O)[C@H]2\N=C(/[O-])CCCC[C@H](NC(=O)CN)C(O)=O)C(O)=O

References

General References
Not Available
PubChem Compound
131704283
PubChem Substance
46504718
PDBe Ligand
H2A
PDB Entries
1pw8

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 Solubility0.392 mg/mLALOGPS
logP-1.9ALOGPS
logP-4.1Chemaxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3Chemaxon
pKa (Strongest Basic)8.14Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area211.75 Å2Chemaxon
Rotatable Bond Count13Chemaxon
Refractivity122.37 m3·mol-1Chemaxon
Polarizability47.24 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability0Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9927
Blood Brain Barrier-0.9664
Caco-2 permeable-0.7356
P-glycoprotein substrateSubstrate0.8162
P-glycoprotein inhibitor INon-inhibitor0.8032
P-glycoprotein inhibitor IINon-inhibitor0.9908
Renal organic cation transporterNon-inhibitor0.8968
CYP450 2C9 substrateNon-substrate0.8644
CYP450 2D6 substrateNon-substrate0.8132
CYP450 3A4 substrateNon-substrate0.5605
CYP450 1A2 substrateNon-inhibitor0.7723
CYP450 2C9 inhibitorNon-inhibitor0.8016
CYP450 2D6 inhibitorNon-inhibitor0.8849
CYP450 2C19 inhibitorNon-inhibitor0.747
CYP450 3A4 inhibitorNon-inhibitor0.8974
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8973
Ames testNon AMES toxic0.7178
CarcinogenicityNon-carcinogens0.9339
BiodegradationNot ready biodegradable0.8055
Rat acute toxicity2.1757 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9747
hERG inhibition (predictor II)Non-inhibitor0.7278
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 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-200.27771
predicted
DeepCCS 1.0 (2019)
[M+H]+202.1026
predicted
DeepCCS 1.0 (2019)
[M+Na]+207.70842
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. D-alanyl-D-alanine carboxypeptidase
Kind
Protein
Organism
Streptomyces sp. (strain R61)
Pharmacological action
Unknown
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Catalyzes distinct carboxypeptidation and transpeptidation reactions during the last stages of wall peptidoglycan synthesis. Mistaking a beta-lactam antibiotic molecule for a normal substrate (i.e....
Gene Name
Not Available
Uniprot ID
P15555
Uniprot Name
D-alanyl-D-alanine carboxypeptidase
Molecular Weight
42916.725 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