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Identification
- Generic Name
- Lysine Nz-Carboxylic Acid
- DrugBank Accession Number
- DB03801
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Lysine Nz-Carboxylic Acid (DB03801)
- Weight
- Average: 190.1971
Monoisotopic: 190.095356946 - Chemical Formula
- C7H14N2O4
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism ACyclin-dependent kinase 2 inhibitorHumans UBeta-lactamase OXA-10 Not Available Pseudomonas aeruginosa UUDP-N-acetylmuramoylalanine--D-glutamate ligase Not Available Escherichia coli (strain K12) UAlanine racemase Not Available Geobacillus stearothermophilus UUDP-N-acetylmuramoyl-L-alanyl-D-glutamate--2,6-diaminopimelate ligase Not Available Escherichia coli (strain K12) UParathion hydrolase Not Available Flavobacterium sp. (strain ATCC 27551) UFolylpolyglutamate synthase Not Available Lactobacillus casei UDihydroorotase Not Available Escherichia coli (strain K12) UD-hydantoinase Not Available Ralstonia pickettii UBeta-lactamase OXA-1 Not Available Escherichia coli UL-hydantoinase Not Available Arthrobacter aurescens UD-hydantoinase Not Available Geobacillus stearothermophilus UMethylmalonyl-CoA carboxyltransferase 5S subunit Not Available Propionibacterium freudenreichii subsp. shermanii UIsoaspartyl dipeptidase Not Available Escherichia coli (strain K12) UBeta-lactamase OXA-2 Not Available Salmonella typhimurium UAlanine racemase, catabolic Not Available Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228) UEndonuclease III Not Available Helicobacter pylori (strain ATCC 700392 / 26695) UHydrolase Not Available Thermus sp. UAlpha-L-fucosidase, putative Not Available Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099) - 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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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 l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- L-alpha-amino acids
- Alternative Parents
- Medium-chain fatty acids / Amino fatty acids / Organic carbonic acids and derivatives / Carbamic acids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines show 2 more
- Substituents
- Aliphatic acyclic compound / Amine / Amino acid / Amino fatty acid / Carbamic acid / Carbamic acid derivative / Carbonic acid derivative / Carbonyl group / Carboxylic acid / Fatty acid show 13 more
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- non-proteinogenic L-alpha-amino acid, L-lysine derivative (CHEBI:43575)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- J9ET8AZ2P7
- CAS number
- Not Available
- InChI Key
- PWIKLEYMFKCERQ-YFKPBYRVSA-N
- InChI
- InChI=1S/C7H14N2O4/c8-5(6(10)11)3-1-2-4-9-7(12)13/h5,9H,1-4,8H2,(H,10,11)(H,12,13)/t5-/m0/s1
- IUPAC Name
- (2S)-2-amino-6-(carboxyamino)hexanoic acid
- SMILES
- N[C@@H](CCCCNC(O)=O)C(O)=O
References
- General References
- Not Available
- External Links
- PDB Entries
- 1aa1 / 1bwv / 1e4d / 1e8c / 1e9y / 1e9z / 1ef2 / 1ejr / 1ejs / 1ejt … show 719 more
Clinical Trials
- Clinical Trials
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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
Property Value Source Water Solubility 13.5 mg/mL ALOGPS logP -3.3 ALOGPS logP -2.8 Chemaxon logS -1.2 ALOGPS pKa (Strongest Acidic) 2.14 Chemaxon pKa (Strongest Basic) 9.53 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 112.65 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 44.11 m3·mol-1 Chemaxon Polarizability 19.15 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.5806 Blood Brain Barrier + 0.8497 Caco-2 permeable - 0.82 P-glycoprotein substrate Non-substrate 0.5691 P-glycoprotein inhibitor I Non-inhibitor 0.9727 P-glycoprotein inhibitor II Non-inhibitor 0.9341 Renal organic cation transporter Non-inhibitor 0.9469 CYP450 2C9 substrate Non-substrate 0.7954 CYP450 2D6 substrate Non-substrate 0.8046 CYP450 3A4 substrate Non-substrate 0.7711 CYP450 1A2 substrate Non-inhibitor 0.8951 CYP450 2C9 inhibitor Non-inhibitor 0.946 CYP450 2D6 inhibitor Non-inhibitor 0.9597 CYP450 2C19 inhibitor Non-inhibitor 0.9243 CYP450 3A4 inhibitor Non-inhibitor 0.8912 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9936 Ames test Non AMES toxic 0.6521 Carcinogenicity Non-carcinogens 0.9254 Biodegradation Ready biodegradable 0.6107 Rat acute toxicity 1.5244 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9812 hERG inhibition (predictor II) Non-inhibitor 0.9653
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00di-9300000000-0674aa2a425ae236b67d Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-3900000000-96b60bc231463a4eb565 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0900000000-f782b68f8c35127e988f Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-9300000000-da816a669121d783f6e8 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-002b-2900000000-ade61e7561c2ff964758 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-006x-9100000000-b6ab605a4e6d027fbfd5 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-9000000000-c9a4f616c8941b8f38d4 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 135.93112 predictedDeepCCS 1.0 (2019) [M+H]+ 139.67488 predictedDeepCCS 1.0 (2019) [M+Na]+ 149.1717 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serine/threonine-protein kinase involved in the control of the cell cycle; essential for meiosis, but dispensable for mitosis (PubMed:10499802, PubMed:10884347, PubMed:10995386, PubMed:10995387, PubMed:11051553, PubMed:11113184, PubMed:12944431, PubMed:15800615, PubMed:17495531, PubMed:19966300, PubMed:20935635, PubMed:21262353, PubMed:21596315, PubMed:28216226, PubMed:28666995). Phosphorylates CABLES1, CTNNB1, CDK2AP2, ERCC6, NBN, USP37, p53/TP53, NPM1, CDK7, RB1, BRCA2, MYC, NPAT, EZH2 (PubMed:10499802, PubMed:10995386, PubMed:10995387, PubMed:11051553, PubMed:11113184, PubMed:12944431, PubMed:15800615, PubMed:19966300, PubMed:20935635, PubMed:21262353, PubMed:21596315, PubMed:28216226). Triggers duplication of centrosomes and DNA (PubMed:11051553). Acts at the G1-S transition to promote the E2F transcriptional program and the initiation of DNA synthesis, and modulates G2 progression; controls the timing of entry into mitosis/meiosis by controlling the subsequent activation of cyclin B/CDK1 by phosphorylation, and coordinates the activation of cyclin B/CDK1 at the centrosome and in the nucleus (PubMed:18372919, PubMed:19238148, PubMed:19561645). Crucial role in orchestrating a fine balance between cellular proliferation, cell death, and DNA repair in embryonic stem cells (ESCs) (PubMed:18372919, PubMed:19238148, PubMed:19561645). Activity of CDK2 is maximal during S phase and G2; activated by interaction with cyclin E during the early stages of DNA synthesis to permit G1-S transition, and subsequently activated by cyclin A2 (cyclin A1 in germ cells) during the late stages of DNA replication to drive the transition from S phase to mitosis, the G2 phase (PubMed:18372919, PubMed:19238148, PubMed:19561645). EZH2 phosphorylation promotes H3K27me3 maintenance and epigenetic gene silencing (PubMed:20935635). Cyclin E/CDK2 prevents oxidative stress-mediated Ras-induced senescence by phosphorylating MYC (PubMed:19966300). Involved in G1-S phase DNA damage checkpoint that prevents cells with damaged DNA from initiating mitosis; regulates homologous recombination-dependent repair by phosphorylating BRCA2, this phosphorylation is low in S phase when recombination is active, but increases as cells progress towards mitosis (PubMed:15800615, PubMed:20195506, PubMed:21319273). In response to DNA damage, double-strand break repair by homologous recombination a reduction of CDK2-mediated BRCA2 phosphorylation (PubMed:15800615). Involoved in regulation of telomere repar by mediating phosphorylation of NBN (PubMed:28216226). Phosphorylation of RB1 disturbs its interaction with E2F1 (PubMed:10499802). NPM1 phosphorylation by cyclin E/CDK2 promotes its dissociates from unduplicated centrosomes, thus initiating centrosome duplication (PubMed:11051553). Cyclin E/CDK2-mediated phosphorylation of NPAT at G1-S transition and until prophase stimulates the NPAT-mediated activation of histone gene transcription during S phase (PubMed:10995386, PubMed:10995387). Required for vitamin D-mediated growth inhibition by being itself inactivated (PubMed:20147522). Involved in the nitric oxide- (NO) mediated signaling in a nitrosylation/activation-dependent manner (PubMed:20079829). USP37 is activated by phosphorylation and thus triggers G1-S transition (PubMed:21596315). CTNNB1 phosphorylation regulates insulin internalization (PubMed:21262353). Phosphorylates FOXP3 and negatively regulates its transcriptional activity and protein stability (By similarity). Phosphorylates ERCC6 which is essential for its chromatin remodeling activity at DNA double-strand breaks (PubMed:29203878)
- Specific Function
- ATP binding
- Gene Name
- CDK2
- Uniprot ID
- P24941
- Uniprot Name
- Cyclin-dependent kinase 2
- Molecular Weight
- 33929.215 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Pseudomonas aeruginosa
- Pharmacological action
- Unknown
- General Function
- Hydrolyzes both carbenicillin and oxacillin.
- Specific Function
- beta-lactamase activity
- Gene Name
- bla
- Uniprot ID
- P14489
- Uniprot Name
- Beta-lactamase OXA-10
- Molecular Weight
- 29506.575 Da
References
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Cell wall formation (Probable). Catalyzes the addition of glutamate to the nucleotide precursor UDP-N-acetylmuramoyl-L-alanine (UMA) (PubMed:1765076).
- Specific Function
- ATP binding
- Gene Name
- murD
- Uniprot ID
- P14900
- Uniprot Name
- UDP-N-acetylmuramoylalanine--D-glutamate ligase
- Molecular Weight
- 46973.185 Da
References
- Kind
- Protein
- Organism
- Geobacillus stearothermophilus
- Pharmacological action
- Unknown
- General Function
- Catalyzes the interconversion of L-alanine and D-alanine. Also weakly active on serine.
- Specific Function
- alanine racemase activity
- Gene Name
- alr
- Uniprot ID
- P10724
- Uniprot Name
- Alanine racemase
- Molecular Weight
- 43592.715 Da
References
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Catalyzes the addition of meso-diaminopimelic acid to the nucleotide precursor UDP-N-acetylmuramoyl-L-alanyl-D-glutamate (UMAG) in the biosynthesis of bacterial cell-wall peptidoglycan. Is also able to use many meso-diaminopimelate analogs as substrates, although much less efficiently, but not L-lysine.
- Specific Function
- ATP binding
- Gene Name
- murE
- Uniprot ID
- P22188
- Uniprot Name
- UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--2,6-diaminopimelate ligase
- Molecular Weight
- 53343.13 Da
References
- Kind
- Protein
- Organism
- Flavobacterium sp. (strain ATCC 27551)
- Pharmacological action
- Unknown
- General Function
- Has an unusual substrate specificity for synthetic organophosphate triesters and phosphorofluoridates. All of the phosphate triesters found to be substrates are synthetic compounds. The identity of any naturally occurring substrate for the enzyme is unknown. Has no detectable activity with phosphate monoesters or diesters and no activity as an esterase or protease. It catalyzes the hydrolysis of the insecticide paraoxon at a rate approaching the diffusion limit and thus appears to be optimally evolved for utilizing this synthetic substrate (By similarity).
- Specific Function
- aryldialkylphosphatase activity
- Gene Name
- opd
- Uniprot ID
- P0A433
- Uniprot Name
- Parathion hydrolase
- Molecular Weight
- 39003.24 Da
References
- Kind
- Protein
- Organism
- Lactobacillus casei
- Pharmacological action
- Unknown
- General Function
- Involved in the conversion of folates to polyglutamate derivatives, and likely functions in the retention of cellular folate pools. Catalyzes successive MgATP-dependent additions of glutamate to a pteroylmonoglutamate substrate, with a high preference for 5,10-methylenetetrahydrofolate (mTHF). Thus, metabolizes mTHF to the tetraglutamate derivative, but longer glutamate chain length products are not observed. Tetrahydrofolate (H4PteGlu) and 10-formyl-H4PteGlu are poorer folate substrates. In contrast to E.coli FolC, this enzyme does not display dihydrofolate synthase activity.
- Specific Function
- ATP binding
- Gene Name
- fgs
- Uniprot ID
- P15925
- Uniprot Name
- Folylpolyglutamate synthase
- Molecular Weight
- 46588.815 Da
References
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Catalyzes the reversible cyclization of carbamoyl aspartate to dihydroorotate.
- Specific Function
- dihydroorotase activity
- Gene Name
- pyrC
- Uniprot ID
- P05020
- Uniprot Name
- Dihydroorotase
- Molecular Weight
- 38827.045 Da
References
- Kind
- Protein
- Organism
- Ralstonia pickettii
- Pharmacological action
- Unknown
- General Function
- Catalyzes the stereospecific hydrolysis of the cyclic amide bond of D-hydantoin derivatives.
- Specific Function
- hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds
- Gene Name
- hyuA
- Uniprot ID
- Q8VTT5
- Uniprot Name
- D-hydantoinase
- Molecular Weight
- 49931.52 Da
References
- Kind
- Protein
- Organism
- Escherichia coli
- Pharmacological action
- Unknown
- General Function
- This is an oxacillin-hydrolyzing beta-lactamase.
- Specific Function
- beta-lactamase activity
- Gene Name
- bla
- Uniprot ID
- P13661
- Uniprot Name
- Beta-lactamase OXA-1
- Molecular Weight
- 30879.895 Da
References
- Kind
- Protein
- Organism
- Arthrobacter aurescens
- Pharmacological action
- Unknown
- General Function
- Rather more predominant for the cleavage of aryl- than for alkyl-hydantoin derivatives. The stereoselectivity of this enzyme depends on the substrate used for bioconversion: strictly L-selective for the cleavage of D,L-5-indolylmethylhydantoin, but D-selective for the hydrolysis of D,L-methylthioethylhydantoin.
- Specific Function
- allantoinase activity
- Gene Name
- lhyD
- Uniprot ID
- P81006
- Uniprot Name
- L-hydantoinase
- Molecular Weight
- 49596.275 Da
References
- Kind
- Protein
- Organism
- Geobacillus stearothermophilus
- Pharmacological action
- Unknown
- General Function
- Catalyzes the stereospecific hydrolysis of the cyclic amide bond of D-hydantoin. Has no activity on dihydropyrimidines.
- Specific Function
- hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds
- Gene Name
- Not Available
- Uniprot ID
- Q45515
- Uniprot Name
- D-hydantoinase
- Molecular Weight
- 51724.68 Da
References
- Kind
- Protein
- Organism
- Propionibacterium freudenreichii subsp. shermanii
- Pharmacological action
- Unknown
- General Function
- The 5S subunit specifically catalyzes the transfer of the carboxyl group from biotin of the 1.3S subunit to pyruvate to form oxaloacetate and 1.3S biotin.
- Specific Function
- metal ion binding
- Gene Name
- Not Available
- Uniprot ID
- Q70AC7
- Uniprot Name
- Methylmalonyl-CoA carboxyltransferase 5S subunit
- Molecular Weight
- 55649.06 Da
References
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Catalyzes the hydrolytic cleavage of a subset of L-isoaspartyl (L-beta-aspartyl) dipeptides. Used to degrade proteins damaged by L-isoaspartyl residues formation. The best substrate for the enzyme reported thus far is iso-Asp-Leu.
- Specific Function
- beta-aspartyl-peptidase activity
- Gene Name
- iadA
- Uniprot ID
- P39377
- Uniprot Name
- Isoaspartyl dipeptidase
- Molecular Weight
- 41083.515 Da
References
- Kind
- Protein
- Organism
- Salmonella typhimurium
- Pharmacological action
- Unknown
- General Function
- This is an oxacillin-hydrolyzing beta-lactamase.
- Specific Function
- beta-lactamase activity
- Gene Name
- bla
- Uniprot ID
- P0A1V8
- Uniprot Name
- Beta-lactamase OXA-2
- Molecular Weight
- 31685.78 Da
References
- Kind
- Protein
- Organism
- Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
- Pharmacological action
- Unknown
- General Function
- Isomerizes L-alanine to D-alanine which is then oxidized to pyruvate by DadA.
- Specific Function
- alanine racemase activity
- Gene Name
- dadX
- Uniprot ID
- Q9HTQ2
- Uniprot Name
- Alanine racemase, catabolic
- Molecular Weight
- 38914.32 Da
References
- Kind
- Protein
- Organism
- Helicobacter pylori (strain ATCC 700392 / 26695)
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- 4 iron, 4 sulfur cluster binding
- Gene Name
- Not Available
- Uniprot ID
- O25323
- Uniprot Name
- Endonuclease III
- Molecular Weight
- 25286.105 Da
- Kind
- Protein
- Organism
- Thermus sp.
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds
- Gene Name
- Not Available
- Uniprot ID
- Q7SIE9
- Uniprot Name
- Hydrolase
- Molecular Weight
- 50675.185 Da
- Kind
- Protein
- Organism
- Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
- Pharmacological action
- Unknown
- General Function
- Alpha-L-fucosidase is responsible for hydrolyzing the alpha-1,6-linked fucose joined to the reducing-end N-acetylglucosamine of the carbohydrate moieties of glycoproteins.
- Specific Function
- alpha-L-fucosidase activity
- Gene Name
- Not Available
- Uniprot ID
- Q9WYE2
- Uniprot Name
- Alpha-L-fucosidase, putative
- Molecular Weight
- 52204.95 Da
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22