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Bovine Metabolome Database



Showing metabocard for Homogentisic acid (BMDB00130)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-06-19 19:36:30
Accession Number BMDB00130
Common Name Homogentisic acid
Description An intermediate of the metabolic breakdown of tyrosine and phenylalanine; it occurs in the urine in cases of alkaptonuria. (OMIN 203500) Homogentisic acid is the primary precursor of melanin synthesis in Vibrio cholerae.
Synonyms
  1. (2,5-dihydroxyphenyl)-Acetate
  2. (2,5-dihydroxyphenyl)-Acetic acid
  3. 2,5-Dihydroxy-a-toluate
  4. 2,5-Dihydroxy-a-toluic acid
  5. 2,5-Dihydroxy-alpha-toluate
  6. 2,5-Dihydroxy-alpha-toluic acid
  7. 2,5-Dihydroxy-benzeneacetate
  8. 2,5-Dihydroxy-benzeneacetic acid
  9. 2,5-Dihydroxyphenylacetate
  10. 2,5-Dihydroxyphenylacetic acid
  11. Alcapton
  12. Homogentisate
  13. Homogentisate acid
  14. Homogentisinate
  15. Homogentisinic acid;Melanic acid.
Chemical IUPAC Name 2-(2,5-dihydroxyphenyl)acetic acid
Chemical Formula C8H8O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Alcohols
Class
  • Hydroxy Acids
Sub Class
  • Miscellaneous catecholamines
Family
  • Mammalian_Metabolite
Species
  • phenol or hydroxyhetarene; carboxylic acid; aromatic compound
Biofunction
  • Component of Phenylalanine metabolism; Component of Tyrosine metabolism
Application
Source
  • Endogenous
Average Molecular Weight 168.147
Monoisotopic Molecular Weight 168.042252
Isomeric SMILES OC(=O)CC1=C(O)C=CC(O)=C1
Canonical SMILES OC(=O)CC1=C(O)C=CC(O)=C1
KEGG Compound ID C00544 Link Image
BioCyc ID Not Available
BiGG ID 1485308 Link Image
Wikipedia Link Homogentisic acid Link Image
METLIN ID 331 Link Image
PubChem Compound 780 Link Image
PubChem Substance 2799 Link Image
ChEBI ID 5755 Link Image
CAS Registry Number 451-13-8
InChI Identifier InChI=1/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
Synthesis Reference Not Available
Melting Point (Experimental) 153 oC
Experimental Water Solubility 850 mg/mL at 25 oC [BEILSTEIN] Source: PhysProp
Predicted Water Solubility 8.10 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity 0.86 [SANGSTER (1994)] Source: PhysProp
Predicted LogP/Hydrophobicity 0.81 [Predicted by ALOGPS]; 0.887 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Bruker)
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
Download File
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High Energy
Download File
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Simplified TOCSY Spectrum Show Image
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BMRB Spectrum Show Image
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Cellular Location
  • Cytoplasm
Biofluid Location Not Available
Tissue Location
Tissue References
Cartilage
Connective Tissue
Kidney
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Tyrosine Metabolism
HMDB Pathways
Name Tyrosine Metabolism
Image Show Link Image
KEGG Pathways
Name Tyrosine Metabolism
Image Show Link Image
SimCell Pathways
Name Tyrosine Metabolism
Image Show Link Image
Graph
SBML
General References
  1. Wikipedia Link Image
Metabolic Enzymes
  1. 4-hydroxyphenylpyruvate dioxygenase
Enzyme 1 [top]
Enzyme 1 ID 684
Enzyme 1 Name 4-hydroxyphenylpyruvate dioxygenase
Enzyme 1 Synonyms
  1. 4-hydroxyphenylpyruvic acid oxidase
  2. HPPDase
  3. 4HPPD
  4. HPD
Enzyme 1 Gene Name HPD
Enzyme 1 Protein Sequence >4-hydroxyphenylpyruvate dioxygenase
MTTYSDKGEKPERGRFLHFHSVTFWVGNAKQAASYYCSKLGFEPLAYKGLETGSREVVSH
VVKQGQIVFVFSSALNPWNKEMGDHLVKHGDGVKDIAFEVEDCDYIVQKARERGAKIVRE
PWVEQDKLGKVKFAVLQTYGDTTHTLVEKMNYTGRFLPGFEAPPFMDPQLSKLPSCSLEI
IDHIVGNQPDQEMVSASEWYLKNLQFHRFWSVDDTQVHTEYSSLRSVVVANYEESIKMPI
NEPAPGKKKSQIQEYVDYNGGAGVQHIALKTKDIITAIRHLRERGVEFLAVPSTYYKQLR
EKLKMAKIRVKENIDILEELKILVDYDEKGYLLQIFTKPMQDRPTLFLEVIQRHNHQGFG
AGNFNSLFKAFEEEQDLRGNLTDMEPNGVVSGM
Enzyme 1 Number of Residues 393
Enzyme 1 Molecular Weight 44963.0
Enzyme 1 Theoretical pI 6.71
Enzyme 1 GO Classification
Function
Process
Component
Enzyme 1 General Function Amino acid transport and metabolism
Enzyme 1 Specific Function 4-hydroxyphenylpyruvate + O(2) = homogentisate + CO(2)
Enzyme 1 Pathways
  • Amino-acid degradation
  • L-phenylalanine degradation
  • acetoacetate and fumarate from L-phenylalanine:step 3/6
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 59857863 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q5EA20 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name HPPD_BOVIN Link Image
Enzyme 1 PDB ID 1SQI Link Image
Enzyme 1 PDB File Show
Enzyme 1 3D Structure
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1182 bp
ATGACGACTTACAGCGACAAAGGAGAGAAGCCTGAAAGAGGCCGATTCCTCCACTTTCAC
TCTGTGACCTTCTGGGTTGGCAATGCCAAGCAGGCTGCGTCATATTACTGCAGTAAGCTG
GGCTTTGAGCCCCTAGCCTACAAGGGCCTGGAGACCGGTTCCCGGGAAGTGGTGAGCCAT
GTGGTCAAGCAAGGGCAGATCGTGTTCGTCTTCTCCTCTGCCCTCAACCCCTGGAACAAA
GAGATGGGCGATCACCTGGTGAAACACGGCGATGGAGTGAAGGACATTGCGTTCGAGGTG
GAGGACTGTGACTACATTGTGCAGAAAGCCCGGGAACGAGGCGCCAAGATTGTGCGGGAG
CCTTGGGTAGAGCAAGATAAGCTTGGGAAGGTGAAGTTTGCTGTGCTACAGACGTATGGG
GACACGACACACACCCTGGTGGAGAAGATGAACTATACTGGCCGGTTCCTGCCTGGATTC
GAGGCACCACCATTCATGGACCCCCAACTTTCCAAGCTGCCCAGCTGCAGTCTCGAGATA
ATCGATCACATTGTGGGAAACCAGCCTGATCAAGAGATGGTGTCTGCCTCTGAATGGTAC
CTGAAGAACTTGCAGTTCCACCGTTTCTGGTCCGTGGATGACACGCAGGTGCACACGGAG
TACAGCTCTCTGCGGTCCGTCGTGGTGGCCAATTATGAGGAATCCATCAAGATGCCCATT
AATGAGCCAGCACCGGGCAAGAAGAAGTCCCAGATCCAGGAATATGTGGACTATAACGGG
GGCGCTGGGGTCCAGCACATTGCTCTCAAGACCAAAGACATCATCACAGCAATTCGCCAC
TTGAGAGAGAGAGGCGTGGAGTTTTTGGCTGTTCCATCCACATACTACAAACAACTGCGG
GAGAAGCTCAAGATGGCCAAGATCCGGGTGAAGGAGAATATTGATATCCTAGAGGAGCTG
AAGATCCTGGTAGACTACGACGAGAAAGGCTACCTCCTGCAGATTTTCACCAAACCCATG
CAGGACCGGCCCACGCTCTTCCTGGAAGTCATTCAGCGCCACAATCACCAGGGTTTTGGA
GCCGGCAACTTCAACTCACTGTTCAAGGCCTTCGAGGAGGAGCAGGACCTGCGAGGCAAC
CTCACCGACATGGAGCCCAATGGGGTTGTGTCCGGCATGTAG
Enzyme 1 GenBank Gene ID BT020749 Link Image
Enzyme 1 GeneCard ID HPD Link Image
Enzyme 1 GenAtlas ID Not Available
Enzyme 1 HGNC ID Not Available
Enzyme 1 Chromosome Location Chromosome:1
Enzyme 1 Locus 12q24-qter
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available