Cannabis Compound Database: Showing Compound Card for L-Phenylalanine (CDB000134)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (16)transporters (2) Show 28 proteins XML

Record Information

Version

1.0

Created at

2020-03-18 23:26:03 UTC

Updated at

2022-12-13 23:36:24 UTC

CannabisDB ID

CDB000134

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

L-Phenylalanine

Description

Phenylalanine, abbreviated Phe or F, is a neutral, nonpolar, hydrophobic, essential amino acid. It is the precursor of the amino acid tyrosine, a precursor of the skin pigment melanin and a precursor of catecholamines that include tyramine, dopamine, epinephrine, and norepinephrine. Catecholamines are neurotransmitters that act as adrenalin-like substances. Interestingly, several psychotropic drugs (mescaline, morphine, codeine, and papaverine) also have phenylalanine as a constituent. Phenylalanine is highly concentrated in the human brain and plasma and is found naturally in mammalian breast milk. Normal metabolism of phenylalanine requires biopterin, iron, niacin, vitamin B6, copper, and vitamin C. An average adult ingests 5 g of phenylalanine per day and may optimally need up to 8 g daily. Phenylalanine is highly concentrated in several high protein foods, such as meat, cottage cheese, and wheat germ. Phenylalanine is also found in Cannabis plants (PMID: 6991645 ). An additional dietary source of phenylalanine is artificial sweeteners containing aspartame. Generally, aspartame should be avoided by phenylketonurics and pregnant women. When present in sufficiently high levels, phenylalanine can act as a neurotoxin and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural cells and neural tissue. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of phenylalanine are associated with at least five inborn errors of metabolism, including Hartnup disorder, hyperphenylalaninemia due to guanosine triphosphate cyclohydrolase deficiency, phenylketonuria (PKU), tyrosinemia type 2 (or Richner-Hanhart syndrome), and tyrosinemia type III (TYRO3). Untreated PKU can lead to intellectual disability, seizures, behavioural problems, and mental disorders. Classic PKU dramatically affects myelination and white matter tracts in untreated infants; this may be one major cause of neurological disorders associated with PKU. PKU patients have elevated serum plasma levels of phenylalanine, up to 400 times normal. High plasma concentrations of phenylalanine influence the blood-brain barrier transport of large neutral amino acids. The high plasma phenylalanine concentrations increase phenylalanine entry into the brain and restrict the entry of other large neutral amino acids (PMID: 19191004 ). Phenylalanine has been found to interfere with different cerebral enzyme systems. PKU individuals may have a musty smell and lighter skin, likely related to altered conversion of phenylalanine to the skin pigment melanin. Mild phenylketonuria may be an unsuspected cause of hyperactivity, learning problems, and other developmental problems in children. It has been recently suggested that PKU may resemble amyloid diseases, such as Alzheimer's disease and Parkinson's disease, due to the formation of toxic amyloid-like assemblies of phenylalanine (PMID: 22706200 ). Phenylalanine also has some potential benefits. Phenylalanine can act as an analgesic, providing relief for premenstrual syndrome and may enhance the effects of acupuncture and electric transcutaneous nerve stimulation (TENS) for Parkinson's patients. Phenylalanine and tyrosine, like L-DOPA, produce a catecholamine-like effect. Phenylalanine is better absorbed than tyrosine and may cause fewer headaches. Low phenylalanine diets have been prescribed for certain cancers with mixed results. For some tumours that use more phenylalanine than others (such as melatonin-producing tumours called melanomas) may benefit from low phenylalanine diets.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-2-Amino-3-phenylpropionic acid	ChEBI
(S)-alpha-Amino-beta-phenylpropionic acid	ChEBI
3-Phenyl-L-alanine	ChEBI
beta-Phenyl-L-alanine	ChEBI
F	ChEBI
Phe	ChEBI
PHENYLALANINE	ChEBI
(S)-2-Amino-3-phenylpropionate	Generator
(S)-a-Amino-b-phenylpropionate	Generator
(S)-a-Amino-b-phenylpropionic acid	Generator
(S)-alpha-Amino-beta-phenylpropionate	Generator
(S)-Α-amino-β-phenylpropionate	Generator
(S)-Α-amino-β-phenylpropionic acid	Generator
b-Phenyl-L-alanine	Generator
Β-phenyl-L-alanine	Generator
(-)-beta-Phenylalanine	HMDB
(L)-Phenylalanine	HMDB
(S)-(-)-Phenylalanine	HMDB
(S)-2-Amino-3-phenylpropanoate	HMDB
(S)-2-Amino-3-phenylpropanoic acid	HMDB
(S)-alpha-Amino-benzenepropanoate	HMDB
(S)-alpha-Amino-benzenepropanoic acid	HMDB
(S)-alpha-Aminobenzenepropanoate	HMDB
(S)-alpha-Aminobenzenepropanoic acid	HMDB
(S)-alpha-Aminohydrocinnamate	HMDB
(S)-alpha-Aminohydrocinnamic acid	HMDB
(S)-Phenylalanine	HMDB
alpha-Aminohydrocinnamate	HMDB
alpha-Aminohydrocinnamic acid	HMDB
beta-Phenyl-alpha-alanine	HMDB
beta-Phenylalanine	HMDB
L-2-Amino-3-phenylpropionate	HMDB
L-2-Amino-3-phenylpropionic acid	HMDB
Phenyl-alanine	HMDB
Phenylalamine	HMDB
L-Isomer phenylalanine	HMDB
Phenylalanine, L isomer	HMDB
Phenylalanine, L-isomer	HMDB
Endorphenyl	HMDB
(6S)-Tetrahydrofolate	HMDB
(6S)-Tetrahydrofolic acid	HMDB
(6S)-THFA	HMDB
5,6,7,8-Tetrahydrofolate	HMDB
Tetrahydrofolate	HMDB
THF	HMDB
5,6,7,8-Tetrahydrofolic acid	HMDB

Chemical Formula

C₉H₁₁NO₂

Average Molecular Weight

165.19

Monoisotopic Molecular Weight

165.079

IUPAC Name

(2S)-2-amino-3-phenylpropanoic acid

Traditional Name

L-phenylalanine

CAS Registry Number

5297-02-9

SMILES

N[C@@H](CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1

InChI Key

COLNVLDHVKWLRT-QMMMGPOBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
L-alpha-amino acid
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

proteinogenic amino acid (CHEBI:17295 )
L-alpha-amino acid (CHEBI:17295 )
phenylalanine (CHEBI:17295 )
erythrose 4-phosphate/phosphoenolpyruvate family amino acid (CHEBI:17295 )
Common amino acids (C00079 )

Ontology

Ingestion

Source:

Food

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

Organ and components:

Prostate

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Role

Indirect biological role:

Industrial application:

Food and nutrition:

Nutritional supplement

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	283 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	26.9 mg/mL	Not Available
logP	-1.38	AVDEEF,A (1997)

Predicted Properties

Property	Value	Source
logP	-1.4	ALOGPS
logP	-1.2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	2.47	ChemAxon
pKa (Strongest Basic)	9.45	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	45.12 m³·mol⁻¹	ChemAxon
Polarizability	17.03 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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)	splash10-00dl-9300000000-4782928378caea601f9b	2018-05-25	View Spectrum
GC-MS	L-Phenylalanine, 2 TMS, GC-MS Spectrum	splash10-0fr6-1930000000-a37fbccaf826443ef70c	Spectrum
GC-MS	L-Phenylalanine, non-derivatized, GC-MS Spectrum	splash10-014l-1940000000-537e2725d621246630c1	Spectrum
GC-MS	L-Phenylalanine, 2 TMS, GC-MS Spectrum	splash10-00di-9630000000-ead0919f9a19d2352d80	Spectrum
GC-MS	L-Phenylalanine, 1 TMS, GC-MS Spectrum	splash10-00di-2900000000-cb2d6dc4bf9515150328	Spectrum
GC-MS	L-Phenylalanine, 2 TMS, GC-MS Spectrum	splash10-014l-2960000000-f77489792f0652dd5613	Spectrum
GC-MS	L-Phenylalanine, non-derivatized, GC-MS Spectrum	splash10-014l-0970000000-792b341dd28b9e30bac2	Spectrum
GC-MS	L-Phenylalanine, non-derivatized, GC-MS Spectrum	splash10-0fr6-1930000000-a37fbccaf826443ef70c	Spectrum
GC-MS	L-Phenylalanine, non-derivatized, GC-MS Spectrum	splash10-014l-1940000000-537e2725d621246630c1	Spectrum
GC-MS	L-Phenylalanine, non-derivatized, GC-MS Spectrum	splash10-0ul9-3659000000-b85be4e71798e2fdc47b	Spectrum
GC-MS	L-Phenylalanine, non-derivatized, GC-MS Spectrum	splash10-00di-9630000000-ead0919f9a19d2352d80	Spectrum
GC-MS	L-Phenylalanine, non-derivatized, GC-MS Spectrum	splash10-00di-2900000000-cb2d6dc4bf9515150328	Spectrum
GC-MS	L-Phenylalanine, non-derivatized, GC-MS Spectrum	splash10-014l-2960000000-f77489792f0652dd5613	Spectrum
Predicted GC-MS	L-Phenylalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006x-9600000000-df38fcb743d8f44fb876	Spectrum
Predicted GC-MS	L-Phenylalanine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-7900000000-f21569d2ec75b88e1bda	Spectrum
Predicted GC-MS	L-Phenylalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Phenylalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Phenylalanine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Phenylalanine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Phenylalanine, 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)	splash10-014i-0900000000-0f3b994108b8a9fd2a56	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0gb9-2900000000-c14d44c8a67621757f3d	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9300000000-08c642dab7f49c00da43	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-7dce1e473976f7d2143e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0f6x-9600000000-711557391093b0d8500a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-0c25a5c116eac7bb059b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-2804f79084ac4e67e155	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-8a71bb1f8424064d7caf	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0f6x-9800000000-e027ff6bb67ce55e80a5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-9f6185e9c7d54189f369	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-df5f72fe2bba91742427	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0ir3-0988735721-bac229222fe7b52812a8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0900000000-453477dec847a3672ffe	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0010963000-079a66bf710f6778bceb	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0000009000-62dbe98de4ecde484fb3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-03di-0900000000-80558c17dc1845663c85	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0002-3900000000-e1ee31d41e48824e84b7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0f6x-9500000000-cc11290a37615f24e16e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-1a6020bce0e1a9a14832	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-38c044a112152626962e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-014i-0900000000-9b908abfcb63153d60b3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-1900000000-3ba5964e151bb1d56188	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-2900000000-20a7d24da0281f5b3b78	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0udi-5900000000-1800642a835b49f3398a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0fb9-9300000000-f262384c85fb843f8a11	2012-08-31	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Transcription/Translation	Not Available	Not Available
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
Tyrosine 3-monooxygenase	TH	11p15.5	P07101	details
Phenylalanine--tRNA ligase alpha subunit	FARSA	19p13.2	Q9Y285	details
Phenylalanine--tRNA ligase, mitochondrial	FARS2	6p25.1	O95363	details
Tyrosine aminotransferase	TAT	16q22.1	P17735	details
Aromatic-L-amino-acid decarboxylase	DDC	7p12.2	P20711	details
Lactoperoxidase	LPO	17q23.1	P22079	details
Phenylalanine-4-hydroxylase	PAH	12q22-q24.2	P00439	details
Peroxiredoxin-6	PRDX6	1q25.1	P30041	details
Myeloperoxidase	MPO	17q23.1	P05164	details
Aspartate aminotransferase, cytoplasmic	GOT1	10q24.1-q25.1	P17174	details
Aspartate aminotransferase, mitochondrial	GOT2	16q21	P00505	details
Eosinophil peroxidase	EPX	17q23.1	P11678	details
Kynurenine--oxoglutarate transaminase 1	CCBL1	9q34.11	Q16773	details
Phenylalanine--tRNA ligase beta subunit	FARSB	2q36.1	Q9NSD9	details
L-amino-acid oxidase	IL4I1	19q13.3-q13.4	Q96RQ9	details
FARSLA protein	FARSLA		Q6IBR2	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Large neutral amino acids transporter small subunit 2	SLC7A8	14q11.2	Q9UHI5	details
Monocarboxylate transporter 10	SLC16A10	6q21-q22	Q8TF71	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Tyrosine 3-monooxygenase	TH	11p15.5	P07101	details
Phenylalanine--tRNA ligase, mitochondrial	FARS2	6p25.1	O95363	details
Lactoperoxidase	LPO	17q23.1	P22079	details
Phenylalanine-4-hydroxylase	PAH	12q22-q24.2	P00439	details
Myeloperoxidase	MPO	17q23.1	P05164	details
Eosinophil peroxidase	EPX	17q23.1	P11678	details
Phenylalanine--tRNA ligase beta subunit	FARSB	2q36.1	Q9NSD9	details
Angiotensin-converting enzyme 2	ACE2	Xp22	Q9BYF1	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Tyrosine 3-monooxygenase	TH	11p15.5	P07101	details
Angiotensin-converting enzyme 2	ACE2	Xp22	Q9BYF1	details

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.307 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.335 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.150 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.208 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.143 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.0507 mg/g dry wt	David S. Wishart,...	details

External Links

HMDB ID

HMDB0000159

DrugBank ID

DB00120

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

6140

PDB ID

Not Available

ChEBI ID

17295

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
van Spronsen FJ, Hoeksma M, Reijngoud DJ: Brain dysfunction in phenylketonuria: is phenylalanine toxicity the only possible cause? J Inherit Metab Dis. 2009 Feb;32(1):46-51. doi: 10.1007/s10545-008-0946-2. Epub 2009 Jan 13. [PubMed:19191004 ]
Adler-Abramovich L, Vaks L, Carny O, Trudler D, Magno A, Caflisch A, Frenkel D, Gazit E: Phenylalanine assembly into toxic fibrils suggests amyloid etiology in phenylketonuria. Nat Chem Biol. 2012 Aug;8(8):701-6. doi: 10.1038/nchembio.1002. Epub 2012 Jun 17. [PubMed:22706200 ]

Only showing the first 10 proteins. There are 28 proteins in total.

Show All

Enzymes

Enzyme Details

1. Tyrosine 3-monooxygenase

General function:: Involved in monooxygenase activity
Specific function:: Plays an important role in the physiology of adrenergic neurons.
Gene Name:: TH
Uniprot ID:: P07101
Molecular weight:: 55611.26

Enzyme Details

2. Phenylalanine--tRNA ligase alpha subunit

General function:: Involved in nucleotide binding
Specific function:: Not Available
Gene Name:: FARSA
Uniprot ID:: Q9Y285
Molecular weight:: 57563.225

Enzyme Details

3. Phenylalanine--tRNA ligase, mitochondrial

General function:: Involved in nucleotide binding
Specific function:: Catalyzes direct attachment of p-Tyr (Tyr) to tRNAPhe. Permits also, with a lower efficiency, the attachment of m-Tyr to tRNAPhe, thereby opening the way for delivery of the misacylated tRNA to the ribosome and incorporation of ROS-damaged amino acid into proteins.
Gene Name:: FARS2
Uniprot ID:: O95363
Molecular weight:: 52356.21

Enzyme Details

4. 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

5. Aromatic-L-amino-acid decarboxylase

General function:: Involved in carboxy-lyase activity
Specific function:: Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:: DDC
Uniprot ID:: P20711
Molecular weight:: 53893.755

Enzyme Details

6. Lactoperoxidase

General function:: Involved in peroxidase activity
Specific function:: May contribute to airway host defense against infection.
Gene Name:: LPO
Uniprot ID:: P22079
Molecular weight:: 70983.6

Enzyme Details

7. Phenylalanine-4-hydroxylase

General function:: Involved in amino acid binding
Specific function:: Not Available
Gene Name:: PAH
Uniprot ID:: P00439
Molecular weight:: 51861.565

Enzyme Details

8. Peroxiredoxin-6

General function:: Involved in antioxidant activity
Specific function:: Involved in redox regulation of the cell. Can reduce H(2)O(2) and short chain organic, fatty acid, and phospholipid hydroperoxides. May play a role in the regulation of phospholipid turnover as well as in protection against oxidative injury.
Gene Name:: PRDX6
Uniprot ID:: P30041
Molecular weight:: 25034.715

Enzyme Details

9. Myeloperoxidase

General function:: Involved in peroxidase activity
Specific function:: Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:: MPO
Uniprot ID:: P05164
Molecular weight:: 83867.71

Enzyme Details

10. 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

Transporters

Enzyme Details

1. Large neutral amino acids transporter small subunit 2

General function:: Involved in transport
Specific function:: Sodium-independent, high-affinity transport of small and large neutral amino acids such as alanine, serine, threonine, cysteine, phenylalanine, tyrosine, leucine, arginine and tryptophan, when associated with SLC3A2/4F2hc. Acts as an amino acid exchanger. Has higher affinity for L-phenylalanine than LAT1 but lower affinity for glutamine and serine. L-alanine is transported at physiological concentrations. Plays a role in basolateral (re)absorption of neutral amino acids. Involved in the uptake of methylmercury (MeHg) when administered as the L-cysteine or D,L-homocysteine complexes, and hence plays a role in metal ion homeostasis and toxicity. Involved in the cellular activity of small molecular weight nitrosothiols, via the stereoselective transport of L-nitrosocysteine (L-CNSO) across the transmembrane. Plays an essential role in the reabsorption of neutral amino acids from the epithelial cells to the bloodstream in the kidney
Gene Name:: SLC7A8
Uniprot ID:: Q9UHI5
Molecular weight:: 58381.1

Enzyme Details

2. Monocarboxylate transporter 10

General function:: Involved in transmembrane transport
Specific function:: Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells
Gene Name:: SLC16A10
Uniprot ID:: Q8TF71
Molecular weight:: 55492.1

Only showing the first 10 proteins. There are 28 proteins in total.

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Showing Compound Card for L-Phenylalanine (CDB000134)

Structure for CDB000134 (L-Phenylalanine)

Enzymes

Transporters