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Bovine Rumen Metabolome Database



Showing metabocard for L-Phenylalanine (RMDB00159)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-10-28 12:38:18
Accession Number RMDB00159
Common Name L-Phenylalanine
Description Phenylalanine is an essential amino acid and the precursor for the amino acid tyrosine. Like tyrosine, it is the precursor of catecholamines in the body (tyramine, dopamine, epinephrine and norepinephrine). The psychotropic drugs (mescaline, morphine, codeine, and papaverine) also have phenylalanine as a constituent. Phenylalanine is a precursor of the neurotransmitters called catecholamines, which are adrenalin-like substances. Phenylalanine is highly concentrated in the human brain and plasma. 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 high protein foods, such as meat, cottage cheese and wheat germ. A new dietary source of phenylalanine is artificial sweeteners containing aspartame. Aspartame appears to be nutritious except in hot beverages; however, it should be avoided by phenylketonurics and pregnant women. Phenylketonurics, who have a genetic error of phenylalanine metabolism, have elevated serum plasma levels of phenylalanine up to 400 times normal. Mild phenylketonuria can be an unsuspected cause of hyperactivity, learning problems, and other developmental problems in children. Phenylalanine can be an effective pain reliever. Its use in premenstrual syndrome and Parkinson's may enhance the effects of acupuncture and electric transcutaneous nerve stimulation (TENS). Phenylalanine and tyrosine, like L-dopa, produce a catecholamine effect. Phenylalanine is better absorbed than tyrosine and may cause fewer headaches. Low phenylalanine diets have been prescribed for certain cancers with mixed results. Some tumors use more phenylalanine (particularly melatonin-producing tumors called melanoma). One strategy is to exclude this amino acid from the diet, i.e., a Phenylketonuria (PKU) diet (compliance is a difficult issue; it is hard to quantify and is under-researched). The other strategy is just to increase phenylalanine's competing amino acids, i.e., tryptophan, valine, isoleucine and leucine, but not tyrosine. (http://www.dcnutrition.com)
Synonyms
  1. (-)-beta-Phenylalanine
  2. (L)-Phenylalanine
  3. (S)-(-)-Phenylalanine
  4. (S)-2-Amino-3-phenylpropionate
  5. (S)-2-Amino-3-phenylpropionic acid
  6. (S)-2-amino-3-phenylpropanoate
  7. (S)-2-amino-3-phenylpropanoic acid
  8. (S)-Phenylalanine
  9. (S)-alpha-Amino-benzenepropanoate
  10. (S)-alpha-Amino-benzenepropanoic acid
  11. (S)-alpha-Amino-beta-phenylpropionate
  12. (S)-alpha-Amino-beta-phenylpropionic acid
  13. (S)-alpha-Aminobenzenepropanoate
  14. (S)-alpha-Aminobenzenepropanoic acid
  15. (S)-alpha-Aminohydrocinnamate
  16. (S)-alpha-Aminohydrocinnamic acid
  17. 3-Phenyl-L-alanine
  18. L-2-Amino-3-phenylpropionate
  19. L-2-Amino-3-phenylpropionic acid
  20. Phe
  21. Phenylalamine
  22. Phenylalanine
  23. alpha-Aminohydrocinnamate
  24. alpha-Aminohydrocinnamic acid
  25. beta-Phenyl-L-alanine
  26. beta-Phenyl-alpha-alanine
  27. beta-Phenylalanine
  28. phenyl-Alanine
Chemical IUPAC Name 2-amino-3-phenyl-propanoic acid
Chemical Formula C9H11NO2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Amino Acids
Sub Class
  • NA
Family
  • Mammalian_Metabolite
Species
  • primary amine; primary aliphatic amine (alkylamine); carboxylic acid; aromatic compound; alpha-aminoacid
Biofunction
  • Essential amino acids; Component of Aminoacyl-tRNA biosynthesis; Component of Novobiocin biosynthesis; Component of Phenylalanine metabolism; Component of Phenylalanine, tyrosine and tryptophan biosynthesis; Component of Tyrosine metabolism
Application
Source
  • Exogenous
Average Molecular Weight 165.189
Monoisotopic Molecular Weight 165.078979
Isomeric SMILES N[C@@H](CC1=CC=CC=C1)C(O)=O
Canonical SMILES NC(CC1=CC=CC=C1)C(O)=O
KEGG Compound ID C00079 Link Image
BioCyc ID PHE Link Image
BiGG ID 33775 Link Image
Wikipedia Link L-Phenylalanine Link Image
METLIN ID 28 Link Image
PubChem Compound 6140 Link Image
PubChem Substance 7847089 Link Image
ChEBI ID 17295 Link Image
CAS Registry Number 63-91-2
InChI Identifier InChI=1/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
Synthesis Reference Zhou, Hua; Zhong, Yao; Sun, Guanghai; Wei, Ping. Preparation of L-phenylalanine by an aqueous two-phase system. Huaxue Fanying Gongcheng Yu Gongyi (2006), 22(2), 146-150.
Melting Point (Experimental) 283 oC
Experimental Water Solubility 26.9 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 4.14 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity -1.38 [AVDEEF,A (1997)] Source: PhysProp
Predicted LogP/Hydrophobicity -1.35 [Predicted by ALOGPS]; -1.4 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • Extracellular
  • mitochondria
Biofluid Location
  • Rumen
  • Blood
  • Cow_Milk
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 17-29 uM
Age N/A
Sex Both
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
Biofluid Rumen
Value 33.5 +/- 16.8 uM
Age 4-5 years old
Sex Female (lactating)
Condition Normal (0% barley grain in dry matter (DM) basis)
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Concentrations (Abnormal)
Biofluid Rumen
Value 36 +/- 13 uM
Age 4-5 years old
Sex Female (lactating)
Condition 15% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 64 +/- 17 uM
Age 4-5 years old
Sex Female (lactating)
Condition 30% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 65 +/- 20 uM
Age 4-5 years old
Sex Female (lactating)
Condition 45% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image
Metabolic Enzymes
  1. Phenylalanine-4-hydroxylase
  2. GTP cyclohydrolase 1 feedback regulatory protein
Enzyme 1 [top]
Enzyme 1 ID 389
Enzyme 1 Name Phenylalanine-4-hydroxylase
Enzyme 1 Synonyms
  1. PAH
  2. Phe-4-monooxygenase
Enzyme 1 Gene Name PAH
Enzyme 1 Protein Sequence >Phenylalanine-4-hydroxylase
MSALVLESRALGRKLSDFGQETSYIEGNSDQNAVSLIFSLKEEVGALARVLRLFEENDIN
LTHIESRPSRLRKDEYEFFTNLDQRSVPALANIIKILRHDIGATVHELSRDKKKDTVPWF
PRTIQELDNFANQVLSYGAELDADHPGFKDPVYRARRKQFADIAYNYRHGQPIPRVEYTE
EEKKTWGTVFRTLKSLYKTHACYEHNHIFPLLEKYCGFREDNIPQLEEVSQFLQSCTGFR
LRPVAGLLSSRDFLGGLAFRVFHCTQYIRHGSKPMYTPEPDICHELLGHVPLFSDRSFAQ
FSQEIGLASLGAPDEYIEKLATIYWFTVEFGLCKQGDSIKAYGAGLLSSFGELQYCLSDK
PKLLPLELEKTAVQEYTITEFQPLYYVAESFNDAKEKVRNFAATIPRPFSVHYDPYTQRI
EVLDNTQQLKILADSISSEVEILCSALQKLK
Enzyme 1 Number of Residues 451
Enzyme 1 Molecular Weight 51726.2
Enzyme 1 Theoretical pI 6.20
Enzyme 1 GO Classification
Function
Process
Component
Enzyme 1 General Function Amino acid transport and metabolism
Enzyme 1 Specific Function L-phenylalanine + tetrahydrobiopterin + O(2) = L-tyrosine + 4a-hydroxytetrahydrobiopterin
Enzyme 1 Pathways
  • Amino-acid degradation
  • L-phenylalanine degradation
  • acetoacetate and fumarate from L-phenylalanine:step 1/6
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 146231900 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q2KIH7 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name PH4H_BOVIN Link Image
Enzyme 1 PDB ID 2PHM Link Image
Enzyme 1 PDB File Show
Enzyme 1 3D Structure
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1356 bp
ATGTCAGCTCTGGTCCTGGAGAGCCGAGCCTTGGGCAGGAAACTCAGCGACTTTGGACAG
GAAACGAGCTATATTGAAGGCAACTCTGATCAAAATGCTGTATCGCTGATCTTCTCACTC
AAAGAAGAAGTTGGTGCACTGGCCAGAGTATTACGTTTATTTGAGGAGAATGATATAAAC
CTGACCCACATTGAATCAAGACCTTCACGTTTAAGGAAAGACGAGTATGAATTTTTCACC
AATCTGGATCAACGCAGCGTGCCTGCCCTGGCAAACATCATCAAGATCTTGAGACATGAC
ATTGGTGCCACTGTGCACGAGCTTTCCCGGGATAAGAAGAAAGACACAGTGCCCTGGTTT
CCAAGAACCATTCAGGAACTCGACAACTTTGCCAACCAGGTTCTCAGCTATGGAGCTGAA
CTGGATGCAGATCACCCGGGATTTAAAGATCCTGTATACCGAGCAAGACGGAAGCAATTC
GCTGACATTGCCTACAACTATAGACATGGGCAGCCCATTCCTCGAGTGGAATACACGGAG
GAAGAAAAAAAAACATGGGGGACGGTATTCAGGACCCTGAAGTCCTTGTATAAGACCCAT
GCTTGCTATGAGCACAACCACATTTTCCCCCTTCTGGAAAAGTATTGCGGCTTCCGTGAA
GATAACATTCCCCAGCTCGAAGAGGTTTCTCAGTTTCTGCAGAGTTGCACTGGTTTCCGC
CTCCGACCAGTCGCTGGCCTGCTTTCTTCTCGGGATTTCTTGGGTGGCCTGGCTTTCCGA
GTCTTCCACTGCACTCAGTACATCAGACATGGGTCTAAGCCCATGTATACACCAGAACCG
GACATATGCCATGAGCTCTTGGGACATGTACCTTTGTTTTCAGATCGCAGCTTTGCCCAG
TTTTCGCAGGAGATCGGCCTTGCCTCCCTGGGTGCACCTGATGAGTACATTGAAAAACTT
GCAACAATTTACTGGTTTACTGTGGAGTTTGGGCTCTGCAAGCAAGGAGACTCCATAAAG
GCATATGGTGCTGGGCTCCTGTCATCCTTTGGTGAATTACAGTATTGCCTATCAGACAAG
CCAAAGCTCCTTCCTCTGGAACTGGAGAAGACCGCTGTCCAGGAGTATACGATCACAGAG
TTCCAGCCTCTGTATTATGTGGCTGAGAGTTTTAATGATGCCAAGGAGAAAGTGAGGAAC
TTTGCTGCCACAATCCCACGGCCCTTCTCAGTTCATTATGACCCATACACTCAACGGATT
GAGGTCTTGGACAACACCCAGCAACTTAAGATTTTGGCTGACTCCATCAGTAGTGAAGTT
GAGATCCTTTGCAGTGCCCTCCAGAAATTAAAGTGA
Enzyme 1 GenBank Gene ID BT030585 Link Image
Enzyme 1 GeneCard ID PAH Link Image
Enzyme 1 GenAtlas ID Not Available
Enzyme 1 HGNC ID Not Available
Enzyme 1 Chromosome Location Chromosome:1
Enzyme 1 Locus 12q22-q24.2
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available
Enzyme 2 [top]
Enzyme 2 ID 1278
Enzyme 2 Name GTP cyclohydrolase 1 feedback regulatory protein
Enzyme 2 Synonyms
  1. GTP cyclohydrolase I feedback regulatory protein
  2. GFRP
Enzyme 2 Gene Name GCHFR
Enzyme 2 Protein Sequence >GTP cyclohydrolase 1 feedback regulatory protein
MPYLLISTQIRMEVGPTVVGDEHSDPELMQHLGASKRSVLGNNFSEYYVNDPPRIVLDKL
ERRGFRVLSMTGVGQTLVWCLHKE
Enzyme 2 Number of Residues 84
Enzyme 2 Molecular Weight 9557.0
Enzyme 2 Theoretical pI 6.79
Enzyme 2 GO Classification
Function
Process
Component
Enzyme 2 General Function Involved in protein binding
Enzyme 2 Specific Function Mediates tetrahydrobiopterin inhibition of GTP cyclohydrolase 1. This inhibition is reversed by L-phenylalanine
Enzyme 2 Pathways Not Available
Enzyme 2 Reactions Not Available
Enzyme 2 Pfam Domain Function
Enzyme 2 Signals
  • None
Enzyme 2 Transmembrane Regions
  • None
Enzyme 2 Essentiality Not Available
Enzyme 2 GenBank ID Protein 81674344 Link Image
Enzyme 2 UniProtKB/Swiss-Prot ID Q32L41 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name GFRP_BOVIN Link Image
Enzyme 2 PDB ID 1IS8 Link Image
Enzyme 2 PDB File Show
Enzyme 2 3D Structure
Enzyme 2 Cellular Location Not Available
Enzyme 2 Gene Sequence >255 bp
ATGCCCTACCTGCTCATCAGCACCCAGATACGCATGGAGGTGGGCCCCACCGTGGTGGGC
GATGAGCACTCAGATCCAGAACTGATGCAGCATCTGGGGGCCTCAAAAAGAAGTGTCCTG
GGAAACAACTTCTCTGAGTACTACGTGAATGACCCTCCTCGAATCGTCCTGGACAAGCTG
GAGCGCAGGGGCTTCCGTGTGCTGAGCATGACAGGGGTGGGCCAGACGCTGGTGTGGTGC
CTGCACAAGGAGTGA
Enzyme 2 GenBank Gene ID BC109778 Link Image
Enzyme 2 GeneCard ID GCHFR Link Image
Enzyme 2 GenAtlas ID Not Available
Enzyme 2 HGNC ID Not Available
Enzyme 2 Chromosome Location Chromosome:1
Enzyme 2 Locus 15q15
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 General References Not Available
Enzyme 2 Metabolite References Not Available