NAV

(2S,5R,6R)-6-({(6S)-6-[(Ammonioacetyl)amino]-6-carboxylatohexanoyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Identification

Generic Name
(2S,5R,6R)-6-({(6S)-6-[(Ammonioacetyl)amino]-6-carboxylatohexanoyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
DrugBank Accession Number
DB03820
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 429.468
Monoisotopic: 429.144394864
Chemical Formula
C17H25N4O7S
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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Penicillins / N-acyl-L-alpha-amino acids / Alpha amino acid amides / Medium-chain fatty acids / Heterocyclic fatty acids / N-acyl amines / Dicarboxylic acids and derivatives / Thiazolidines / Tertiary carboxylic acid amides / Quaternary ammonium salts
show 14 more
Substituents
Aliphatic heteropolycyclic compound / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Amine / Amino acid / Amino acid or derivatives / Azacycle / Azetidine / Beta-lactam
show 35 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
LDJWRKFRKCXUDO-RBQWDTSBSA-M
InChI
InChI=1S/C17H26N4O7S/c1-17(2)12(16(27)28)21-13(24)11(14(21)29-17)20-9(22)6-4-3-5-8(15(25)26)19-10(23)7-18/h8,11-12,14H,3-7,18H2,1-2H3,(H,19,23)(H,20,22)(H,25,26)(H,27,28)/p-1/t8-,11+,12-,14+/m0/s1
IUPAC Name
(2S,5R,6R)-6-[(6S)-6-(2-azaniumylacetamido)-6-carboxylatohexanamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
SMILES
[H]N([C@@H](CCCCC(=O)N([H])[C@@H]1C(=O)N2[C@@H](C([O-])=O)C(C)(C)S[C@]12[H])C([O-])=O)C(=O)C[N+]([H])([H])[H]

References

General References
Not Available
PubChem Compound
131704259
PubChem Substance
46504856
ChemSpider
4450683
PDBe Ligand
HEL
PDB Entries
1pw1

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 Solubility1.97 mg/mLALOGPS
logP-1.4ALOGPS
logP-4.2Chemaxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.09Chemaxon
pKa (Strongest Basic)8.14Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area186.41 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity133.42 m3·mol-1Chemaxon
Polarizability41.8 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9903
Blood Brain Barrier-0.9717
Caco-2 permeable-0.738
P-glycoprotein substrateSubstrate0.7417
P-glycoprotein inhibitor INon-inhibitor0.8202
P-glycoprotein inhibitor IINon-inhibitor0.9934
Renal organic cation transporterNon-inhibitor0.932
CYP450 2C9 substrateNon-substrate0.8539
CYP450 2D6 substrateNon-substrate0.8026
CYP450 3A4 substrateSubstrate0.5603
CYP450 1A2 substrateNon-inhibitor0.8668
CYP450 2C9 inhibitorNon-inhibitor0.8539
CYP450 2D6 inhibitorNon-inhibitor0.8973
CYP450 2C19 inhibitorNon-inhibitor0.792
CYP450 3A4 inhibitorNon-inhibitor0.9108
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9691
Ames testNon AMES toxic0.7859
CarcinogenicityNon-carcinogens0.8633
BiodegradationNot ready biodegradable0.8255
Rat acute toxicity2.1677 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9971
hERG inhibition (predictor II)Non-inhibitor0.8385
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]-198.97203
predicted
DeepCCS 1.0 (2019)
[M+H]+200.86743
predicted
DeepCCS 1.0 (2019)
[M+Na]+206.51683
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