4-Hydroxyphenylpyruvic acid
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Identification
- Generic Name
- 4-Hydroxyphenylpyruvic acid
- DrugBank Accession Number
- DB07718
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 180.1574
Monoisotopic: 180.042258744 - Chemical Formula
- C9H8O4
- Synonyms
- (4-hydroxyphenyl)pyruvic acid
- (p-hydroxyphenyl)pyruvic acid
- p-Hydroxyphenylpyruvic acid
- External IDs
- NSC-100738
- NSC-666757
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AProthrombin inhibitorHumans AMacrophage migration inhibitory factor inhibitorHumans UPrephenate dehydrogenase Not Available Aquifex aeolicus (strain VF5) - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
Pathway Category Phenylketonuria Disease Tyrosine Metabolism Metabolic Tyrosinemia Type I Disease Tyrosinemia Type 3 (TYRO3) Disease Disulfiram Action Pathway Drug action Phenylalanine and Tyrosine Metabolism Metabolic Alkaptonuria Disease Hawkinsinuria Disease Tyrosinemia Type 2 (or Richner-Hanhart Syndrome) Disease Tyrosinemia, Transient, of the Newborn Disease Dopamine beta-Hydroxylase Deficiency Disease Monoamine Oxidase-A Deficiency (MAO-A) Disease - 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
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpyruvic acid derivatives. These are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenylpyruvic acid derivatives
- Direct Parent
- Phenylpyruvic acid derivatives
- Alternative Parents
- Phenylpropanoic acids / 1-hydroxy-2-unsubstituted benzenoids / Alpha-keto acids and derivatives / Alpha-hydroxy ketones / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 3-phenylpropanoic-acid / Alpha-hydroxy ketone / Alpha-keto acid / Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Keto acid
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- phenols, oxo carboxylic acid (CHEBI:15999)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 0YP1694WNQ
- CAS number
- 156-39-8
- InChI Key
- KKADPXVIOXHVKN-UHFFFAOYSA-N
- InChI
- InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)
- IUPAC Name
- 3-(4-hydroxyphenyl)-2-oxopropanoic acid
- SMILES
- OC(=O)C(=O)CC1=CC=C(O)C=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000707
- KEGG Compound
- C01179
- PubChem Compound
- 979
- PubChem Substance
- 99444189
- ChemSpider
- 954
- ChEBI
- 15999
- ChEMBL
- CHEMBL607712
- ZINC
- ZINC000000895711
- PDBe Ligand
- ENO
- Wikipedia
- 4-Hydroxyphenylpyruvic_acid
- PDB Entries
- 1ca7 / 3gac / 3ggo / 3tx6 / 3uk0 / 3ukj / 4eyq / 4jb0 / 4kig / 5zbf … show 2 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 1.49 mg/mL ALOGPS logP 1.12 ALOGPS logP 1.6 Chemaxon logS -2.1 ALOGPS pKa (Strongest Acidic) 2.91 Chemaxon pKa (Strongest Basic) -6 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 74.6 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 44.69 m3·mol-1 Chemaxon Polarizability 16.75 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 + 0.8829 Blood Brain Barrier + 0.6663 Caco-2 permeable - 0.6945 P-glycoprotein substrate Non-substrate 0.7002 P-glycoprotein inhibitor I Non-inhibitor 0.961 P-glycoprotein inhibitor II Non-inhibitor 0.9607 Renal organic cation transporter Non-inhibitor 0.9201 CYP450 2C9 substrate Non-substrate 0.8473 CYP450 2D6 substrate Non-substrate 0.9196 CYP450 3A4 substrate Non-substrate 0.7244 CYP450 1A2 substrate Non-inhibitor 0.9836 CYP450 2C9 inhibitor Non-inhibitor 0.9768 CYP450 2D6 inhibitor Non-inhibitor 0.9701 CYP450 2C19 inhibitor Non-inhibitor 0.9761 CYP450 3A4 inhibitor Non-inhibitor 0.965 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9844 Ames test Non AMES toxic 0.896 Carcinogenicity Non-carcinogens 0.9065 Biodegradation Ready biodegradable 0.8661 Rat acute toxicity 1.7101 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9655 hERG inhibition (predictor II) Non-inhibitor 0.9699
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 145.2842277 predictedDarkChem Lite v0.1.0 [M-H]- 142.2891902 predictedDarkChem Standard v0.1.0 [M-H]- 145.5274277 predictedDarkChem Lite v0.1.0 [M-H]- 145.7220277 predictedDarkChem Lite v0.1.0 [M-H]- 134.65358 predictedDeepCCS 1.0 (2019) [M+H]+ 148.5023277 predictedDarkChem Lite v0.1.0 [M+H]+ 146.9305277 predictedDarkChem Lite v0.1.0 [M+H]+ 146.5963277 predictedDarkChem Lite v0.1.0 [M+H]+ 146.5342277 predictedDarkChem Lite v0.1.0 [M+H]+ 137.04913 predictedDeepCCS 1.0 (2019) [M+Na]+ 146.1642277 predictedDarkChem Lite v0.1.0 [M+Na]+ 146.0345277 predictedDarkChem Lite v0.1.0 [M+Na]+ 146.1695277 predictedDarkChem Lite v0.1.0 [M+Na]+ 145.9266277 predictedDarkChem Lite v0.1.0 [M+Na]+ 144.47086 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsProthrombin
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C. Functions in blood homeostasis, inflammation and wound healing. Thrombin triggers the production of pro-inflammatory cytokines, such as MCP-1/CCL2 and IL8/CXCL8, in endothelial cells (PubMed:30568593, PubMed:9780208)
- Specific Function
- calcium ion binding
- Gene Name
- F2
- Uniprot ID
- P00734
- Uniprot Name
- Prothrombin
- Molecular Weight
- 70036.295 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]
- 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]
2. DetailsMacrophage migration inhibitory factor
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Pro-inflammatory cytokine involved in the innate immune response to bacterial pathogens (PubMed:15908412, PubMed:17443469, PubMed:23776208). The expression of MIF at sites of inflammation suggests a role as mediator in regulating the function of macrophages in host defense (PubMed:15908412, PubMed:17443469, PubMed:23776208). Counteracts the anti-inflammatory activity of glucocorticoids (PubMed:15908412, PubMed:17443469, PubMed:23776208). Has phenylpyruvate tautomerase and dopachrome tautomerase activity (in vitro), but the physiological substrate is not known (PubMed:11439086, PubMed:17526494). It is not clear whether the tautomerase activity has any physiological relevance, and whether it is important for cytokine activity (PubMed:11439086, PubMed:17526494)
- Specific Function
- chemoattractant activity
- Gene Name
- MIF
- Uniprot ID
- P14174
- Uniprot Name
- Macrophage migration inhibitory factor
- Molecular Weight
- 12476.19 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]
- 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]
3. DetailsPrephenate dehydrogenase
- Kind
- Protein
- Organism
- Aquifex aeolicus (strain VF5)
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- NAD+ binding
- Gene Name
- tyrA
- Uniprot ID
- O67636
- Uniprot Name
- Prephenate dehydrogenase
- Molecular Weight
- 34849.26 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 21:25 / Updated at August 26, 2024 19:22