Cannabis Compound Database: Showing Compound Card for 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto) (CDB005145)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (8) Show 10 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:13:52 UTC

Updated at

2020-12-07 19:11:40 UTC

CannabisDB ID

CDB005145

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto)

Description

Phenylpyruvic acid, also known as keto-phenylpyruvate or a-ketohydrocinnamate, belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. Phenylpyruvic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Phenylpyruvic acid exists in all living species, ranging from bacteria to humans. Within humans, phenylpyruvic acid participates in a number of enzymatic reactions. In particular, phenylpyruvic acid and L-glutamic acid can be biosynthesized from L-phenylalanine and oxoglutaric acid; which is mediated by the enzyme aspartate aminotransferase, cytoplasmic. In addition, phenylpyruvic acid can be biosynthesized from L-phenylalanine through the action of the enzyme L-amino-acid oxidase. In humans, phenylpyruvic acid is involved in the metabolic disorder called tyrosinemia type 3 (tyro3). Phenylpyruvic acid is a potentially toxic compound. Phenylpyruvic acid, with regard to humans, has been found to be associated with the diseases such as primary biliary cirrhosis; phenylpyruvic acid has also been linked to the inborn metabolic disorder phenylketonuria. High levels of phenylpyruvic acid can be found in the urine of individuals with phenylketonuria (PKU), an inborn error of metabolism. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid. Metabolites of this transamination reaction include phenylacetate, Phenylpyruvic acid and phenethylamine. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. A "musty or mousy" odor of skin, hair, sweat and urine (due to phenylacetate accumulation); and a tendency to hypopigmentation and eczema are also observed. 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto) is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Phenyl-2-oxopropanoate	ChEBI
3-Phenyl-2-oxopropanoic acid	ChEBI
3-Phenylpyruvic acid	ChEBI
alpha-Ketohydrocinnamic acid	ChEBI
alpha-Oxo-benzenepropanoic acid	ChEBI
beta-Phenylpyruvic acid	ChEBI
Keto-phenylpyruvate	ChEBI
Phenylbrenztraubensaeure	ChEBI
Phenylpyruvate	ChEBI
3-PHENYLPYRUVate	Generator
a-Ketohydrocinnamate	Generator
a-Ketohydrocinnamic acid	Generator
alpha-Ketohydrocinnamate	Generator
α-Ketohydrocinnamate	Generator
α-Ketohydrocinnamic acid	Generator
a-Oxo-benzenepropanoate	Generator
a-Oxo-benzenepropanoic acid	Generator
alpha-Oxo-benzenepropanoate	Generator
α-Oxo-benzenepropanoate	Generator
α-Oxo-benzenepropanoic acid	Generator
b-Phenylpyruvate	Generator
b-Phenylpyruvic acid	Generator
beta-Phenylpyruvate	Generator
β-Phenylpyruvate	Generator
β-Phenylpyruvic acid	Generator
keto-Phenylpyruvic acid	Generator
2-Oxo-3-phenylpropanoate	HMDB, KEGG
2-Oxo-3-phenylpropanoic acid	HMDB, Generator
a-Hydroxycinnamic acid	HMDB
FEMA 3892	HMDB
Phenylpyruvic acid	ChEBI
2-Oxo-3-phenylpropionic acid	HMDB
3-Phenyl-2-oxopropionic acid	HMDB
alpha-Oxobenzenepropanoic acid	HMDB
alpha-Oxobenzenepropionic acid	HMDB
α-Oxobenzenepropanoic acid	HMDB
α-Oxobenzenepropionic acid	HMDB

Chemical Formula

C₉H₈O₃

Average Molecular Weight

164.16

Monoisotopic Molecular Weight

164.0473

IUPAC Name

2-oxo-3-phenylpropanoic acid

Traditional Name

phenylpyruvic acid

CAS Registry Number

156-06-9

SMILES

OC(=O)C(=O)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12)

InChI Key

BTNMPGBKDVTSJY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives 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

Substituents

Phenylpyruvate
3-phenylpropanoic-acid
Keto acid
Alpha-keto acid
Alpha-hydroxy ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:30851 )

Ontology

Physiological effect

Health effect:

Health condition:

Primary biliary cirrhosis

Disposition

Source:

Endogenous

Biological:

Microbe:

Lactobacillus

Biological location:

Biofluid and excreta:

Subcellular:

Role

Industrial application:

Food and nutrition:

Flavoring agent

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	154 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	112 mg/mL	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.9	ChemAxon
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	-9.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	42.71 m³·mol⁻¹	ChemAxon
Polarizability	15.75 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00kf-9300000000-d1a7d23e7c5270b16883	2014-09-20	View Spectrum
GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), 1 TMS, GC-MS Spectrum	splash10-00ko-9700000000-1a891469df1de787159b	Spectrum
GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum	splash10-0006-1900000000-7dc1a5344d13e4dc19ac	Spectrum
GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum	splash10-001i-0900000000-bbbc84c54d03c4a14e51	Spectrum
GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum	splash10-0a4i-0900000000-00b547b0371603520b61	Spectrum
GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), 1 TMS; 1 MEOX, GC-MS Spectrum	splash10-00di-9100000000-fdd48b632e63c8478078	Spectrum
GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-000f-9300000000-8cd32f87e04ae0b6d6fb	Spectrum
GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-014u-9720000000-7a0b66e6c18ff42ac05e	Spectrum
GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), 2 TMS, GC-MS Spectrum	splash10-0006-9760000000-d94111a7b9babceb265b	Spectrum
GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum	splash10-00ko-9700000000-1a891469df1de787159b	Spectrum
GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum	splash10-00di-9100000000-fdd48b632e63c8478078	Spectrum
GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum	splash10-000f-9300000000-8cd32f87e04ae0b6d6fb	Spectrum
GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum	splash10-014u-9720000000-7a0b66e6c18ff42ac05e	Spectrum
GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum	splash10-0006-9760000000-d94111a7b9babceb265b	Spectrum
GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum	splash10-000f-9300000000-8cd32f87e04ae0b6d6fb	Spectrum
GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum	splash10-014u-9720000000-7a0b66e6c18ff42ac05e	Spectrum
GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum	splash10-0006-9760000000-d94111a7b9babceb265b	Spectrum
GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum	splash10-00ko-9700000000-cec4a53271b8d66c2abc	Spectrum
Predicted GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9300000000-9a8a36c751256480752e	Spectrum
Predicted GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00r6-9500000000-3e83cb905f1fd4362497	Spectrum
Predicted GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-066r-0900000000-ceb2ce23352e0f45ee33	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9200000000-ed4a6740d574858da982	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9000000000-c239a9a599daa607e47f	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-014i-0900000000-36e00f6baa5d907e851b	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative	splash10-014i-0900000000-843a66173124c8fdf184	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-014i-0900000000-272f6079d347e1b34e86	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-1900000000-5d025096b1bb0e80dc1c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014m-3900000000-9d0be907ecb6cc5efe8c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9200000000-a4fc563b3536eafc044d	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-0f660ae6dc074d939404	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-1900000000-d229883bf098b04e0fcb	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-5900000000-a107b725b71a6441a80c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03xr-1900000000-8ba05dd4c5612aae9f50	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9300000000-946fa61c2a2596d7592d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-fa13a9bfbb6c03b2e12d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014l-4900000000-2d56731d3ebcebf8079a	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9200000000-9b3ae8fbf3992b1b2f28	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-089373761153dce3ca74	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phenylalanine and Tyrosine Metabolism
Phenylketonuria		Not Available
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)		Not Available
Tyrosinemia Type 3 (TYRO3)		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Macrophage migration inhibitory factor	MIF	22q11.23	P14174	details
Tyrosine aminotransferase	TAT	16q22.1	P17735	details
Aspartate aminotransferase, cytoplasmic	GOT1	10q24.1-q25.1	P17174	details
Aspartate aminotransferase, mitochondrial	GOT2	16q21	P00505	details
Kynurenine--oxoglutarate transaminase 1	CCBL1	9q34.11	Q16773	details
UDP-glucuronosyltransferase 1-1	UGT1A1	2q37	P22309	details
4-hydroxyphenylpyruvate dioxygenase	HPD	12q24-qter	P32754	details
L-amino-acid oxidase	IL4I1	19q13.3-q13.4	Q96RQ9	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
4-hydroxyphenylpyruvate dioxygenase	HPD	12q24-qter	P32754	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Macrophage migration inhibitory factor	MIF	22q11.23	P14174	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000205

DrugBank ID

DB03884

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

30851

References

General References

Not Available

Enzymes

Enzyme Details

1. Macrophage migration inhibitory factor

General function:: Involved in cell surface binding
Specific function:: Pro-inflammatory cytokine. Involved in the innate immune response to bacterial pathogens. The expression of MIF at sites of inflammation suggests a role as mediator in regulating the function of macrophages in host defense. Counteracts the anti-inflammatory activity of glucocorticoids. Has phenylpyruvate tautomerase and dopachrome tautomerase activity (in vitro), but the physiological substrate is not known. It is not clear whether the tautomerase activity has any physiological relevance, and whether it is important for cytokine activity.
Gene Name:: MIF
Uniprot ID:: P14174
Molecular weight:: 12476.19

Enzyme Details

2. Tyrosine aminotransferase

General function:: Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:: Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using glutamic acid, with 2-oxoglutarate as cosubstrate (in vitro). Has much lower affinity and transaminase activity towards phenylalanine.
Gene Name:: TAT
Uniprot ID:: P17735
Molecular weight:: 50398.895

Enzyme Details

3. Aspartate aminotransferase, cytoplasmic

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Plays a key role in amino acid metabolism (By similarity).
Gene Name:: GOT1
Uniprot ID:: P17174
Molecular weight:: 46247.14

Enzyme Details

4. Aspartate aminotransferase, mitochondrial

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:: GOT2
Uniprot ID:: P00505
Molecular weight:: 47517.285

Enzyme Details

5. Kynurenine--oxoglutarate transaminase 1

General function:: Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to form reactive metabolites. Catalyzes the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond.
Gene Name:: CCBL1
Uniprot ID:: Q16773
Molecular weight:: 47874.765

Enzyme Details

6. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Enzyme Details

7. 4-hydroxyphenylpyruvate dioxygenase

General function:: Involved in 4-hydroxyphenylpyruvate dioxygenase activity
Specific function:: Key enzyme in the degradation of tyrosine.
Gene Name:: HPD
Uniprot ID:: P32754
Molecular weight:: 40497.105

Enzyme Details

8. L-amino-acid oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Lysosomal L-amino-acid oxidase with highest specific activity with phenylalanine. May play a role in lysosomal antigen processing and presentation (By similarity).
Gene Name:: IL4I1
Uniprot ID:: Q96RQ9
Molecular weight:: 65327.26

Showing Compound Card for 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto) (CDB005145)

Structure for CDB005145 (2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto))

Enzymes