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Identification
- Generic Name
- (2E)-3-(3,4-DIHYDROXYPHENYL)-2-IMINOPROPANOIC ACID
- DrugBank Accession Number
- DB07979
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for (2E)-3-(3,4-DIHYDROXYPHENYL)-2-IMINOPROPANOIC ACID (DB07979)
- Weight
- Average: 195.1721
Monoisotopic: 195.053157781 - Chemical Formula
- C9H9NO4
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism UD-amino-acid oxidase Not Available Humans - 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
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- VFINRVRRNHRWEQ-POHAHGRESA-N
- InChI
- InChI=1S/C9H9NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,10-12H,3H2,(H,13,14)/b10-6-
- IUPAC Name
- 3-(3,4-dihydroxyphenyl)-2-iminopropanoic acid
- SMILES
- [H]N=C(CC1=CC(O)=C(O)C=C1)C(O)=O
References
- General References
- Not Available
- External Links
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 0.533 mg/mL ALOGPS logP 0.69 ALOGPS logP 0.82 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 3.62 Chemaxon pKa (Strongest Basic) 2.6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 101.61 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 59.15 m3·mol-1 Chemaxon Polarizability 18.07 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8149 Blood Brain Barrier - 0.8251 Caco-2 permeable - 0.8353 P-glycoprotein substrate Substrate 0.5 P-glycoprotein inhibitor I Non-inhibitor 0.9831 P-glycoprotein inhibitor II Non-inhibitor 0.9666 Renal organic cation transporter Non-inhibitor 0.8666 CYP450 2C9 substrate Non-substrate 0.7295 CYP450 2D6 substrate Non-substrate 0.8408 CYP450 3A4 substrate Non-substrate 0.6551 CYP450 1A2 substrate Non-inhibitor 0.8879 CYP450 2C9 inhibitor Non-inhibitor 0.9721 CYP450 2D6 inhibitor Non-inhibitor 0.9118 CYP450 2C19 inhibitor Non-inhibitor 0.9498 CYP450 3A4 inhibitor Non-inhibitor 0.926 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9611 Ames test AMES toxic 0.7647 Carcinogenicity Non-carcinogens 0.9254 Biodegradation Ready biodegradable 0.6321 Rat acute toxicity 2.3100 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.986 hERG inhibition (predictor II) Non-inhibitor 0.9488
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0fft-2900000000-6715ff6e987d925ee61a Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0fka-2900000000-91eb2a056247ee979efa Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0uxv-2900000000-63875ebd35402ce57add Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-1900000000-1ed904c3b597cb067cfd Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00ea-5900000000-133de2d9db9811544567 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-05fu-7900000000-4cca94b51eceadd949c0 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-015d-9300000000-d81194212a536b2e6cc5 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]- 139.36899 predictedDeepCCS 1.0 (2019) [M+H]+ 141.76454 predictedDeepCCS 1.0 (2019) [M+Na]+ 148.32469 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Catalyzes the oxidative deamination of D-amino acids with broad substrate specificity (PubMed:16616139, PubMed:17088322, PubMed:17303072, PubMed:18544534, PubMed:20368421, PubMed:20567862, PubMed:20603179, PubMed:22203986, PubMed:23219954, PubMed:23391306, PubMed:25030849, PubMed:25701391, PubMed:29274788, PubMed:29326945, PubMed:30938755, PubMed:31799256, PubMed:32730563, PubMed:33484270, PubMed:34041270, PubMed:37558109, PubMed:38035964). Required to catabolize D-amino acids synthesized endogenously, of gastrointestinal bacterial origin or obtained from the diet, and to use these as nutrients (By similarity). Regulates the level of D-amino acid neurotransmitters in the brain, such as D-serine, a co-agonist of N-methyl D-aspartate (NMDA) receptors, and may modulate synaptic transmission (PubMed:17303072). Catalyzes the first step of the racemization of D-DOPA to L-DOPA, for possible use in an alternative dopamine biosynthesis pathway (PubMed:17303072). Also catalyzes the first step of the chiral inversion of N(gamma)-nitro-D-arginine methyl ester (D-NNA) to its L-enantiomer L-NNA that acts as a nitric oxide synthase inhibitor (By similarity). The hydrogen peroxide produced in the reaction provides protection against microbial infection; it contributes to the oxidative killing activity of phagocytic leukocytes and protects against bacterial colonization of the small intestine (By similarity). Enzyme secreted into the lumen of the intestine may not be catalytically active and could instead be proteolytically cleaved into peptides with antimicrobial activity (By similarity). The hydrogen peroxide produced in the reaction may also play a role in promoting cellular senescence in response to DNA damage (PubMed:30659069). Could act as a detoxifying agent which removes D-amino acids accumulated during aging (PubMed:17303072)
- Specific Function
- D-amino-acid oxidase activity
- Gene Name
- DAO
- Uniprot ID
- P14920
- Uniprot Name
- D-amino-acid oxidase
- Molecular Weight
- 39473.75 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at September 15, 2010 21:27 / Updated at June 12, 2020 16:52