| Version |
2.5 |
| Creation Date |
2008-08-28 22:53:21 |
| Update Date |
2009-05-05 21:01:27 |
| Accession Number |
HMDB06915 |
| Secondary Accession Numbers |
Not Available |
| Common Name |
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid |
| Description |
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid is an intermediate in tyrosine metabolism. It is reversibly converted from 4-hydroxyphenylpyruvate via phenylpyruvate tautomerase. 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid is typically a terminal product of tyrosine metabolism. |
| Synonyms |
- 2-Hydroxy-3-(4-hydroxyphenyl)propenoate
- 4-Hydroxy-enol-phenylpyruvate
- 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid
|
| Chemical IUPAC Name |
(Z)-2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoic acid |
| Chemical Formula |
C9H8O4 |
| Chemical Structure |
 |
| Chemical Taxonomy |
| Kingdom |
|
| Super Class |
|
| Class |
- Hydroxy Acids
- Aromatic Acids
|
| Sub Class |
- Medium chain hydroxy acids
|
| Family |
|
| Species |
- enol
- phenol or hydroxyhetarene
- carboxylic acid
- aromatic compound
|
| Biofunction |
| — |
| Application |
| — |
| Source |
|
|
| Average Molecular Weight |
180.157 |
| Monoisotopic Molecular Weight |
180.042252 |
| Isomeric SMILES |
OC(=O)C(O)=CC1=CC=C(O)C=C1 |
| Canonical SMILES |
OC(=O)C(O)=CC1=CC=C(O)C=C1 |
| KEGG Compound ID |
C05350  |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB06915 |
| Metagene Link |
HMDB06915 |
| METLIN ID |
Not Available |
| PubChem Compound |
636708 |
| PubChem Substance |
7728 |
| ChEBI ID |
Not Available |
| CAS Registry Number |
Not Available |
| InChI Identifier |
InChI=1/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-5,10-11H,(H,12,13)/b8-5- |
| Synthesis Reference |
Not Available |
| Melting Point (Experimental) |
Not Available |
| Experimental Water Solubility |
Not Available
Source: PhysProp
|
| Predicted Water Solubility |
0.814 mg/mL [Predicted by ALOGPS]
Calculated using ALOGPS
|
| Physiological Charge |
-1 |
| State |
Solid |
| Experimental LogP/Hydrophobicity |
Not Available
Source: PhysProp
|
| Predicted LogP/Hydrophobicity |
1.28 [Predicted by ALOGPS]
Calculated using ALOGPS
|
| Material Safety Data Sheet (MSDS) |
Not Available |
| MOL File |
Show |
| SDF File |
Show |
| PDB File |
Show |
| 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 |
Not Available |
| Simplified TOCSY Spectrum |
Not Available |
| BMRB Spectrum |
Not Available |
| Cellular Location |
Not Available |
| Biofluid Location |
Not Available |
| Tissue Location |
Not Available |
| Concentrations (Normal) |
Not Available |
| Concentrations (Abnormal) |
Not Available |
| Associated Disorders |
Not Available |
| OMIM ID |
Not Available |
| Pathways |
|
| General References |
Not Available |
| Metabolic Enzymes |
- Macrophage migration inhibitory factor
- cDNA, FLJ92196, Homo sapiens macrophage migration inhibitory factor(glycosylation-inhibiting factor) (MIF), mRNA (Macrophage migration inhibitory factor) (Glycosylation-inhibiting factor)
|
|
Enzyme 1
[top]
|
| Enzyme 1 ID |
5332 |
| Enzyme 1 Name |
Macrophage migration inhibitory factor |
| Enzyme 1 Synonyms |
- MIF
- Phenylpyruvate tautomerase
- Glycosylation-inhibiting factor
- GIF
|
| Enzyme 1 Gene Name |
MIF |
| Enzyme 1 Protein Sequence |
>Macrophage migration inhibitory factor
MPMFIVNTNVPRASVPDGFLSELTQQLAQATGKPPQYIAVHVVPDQLMAFGGSSEPCALC
SLHSIGKIGGAQNRSYSKLLCGLLAERLRISPDRVYINYYDMNAANVGWNNSTFA
|
| Enzyme 1 Number of Residues |
115 |
| Enzyme 1 Molecular Weight |
12476 |
| Enzyme 1 Theoretical pI |
8.05 |
| Enzyme 1 GO Classification |
Not Available |
| Enzyme 1 General Function |
Not Available |
| Enzyme 1 Specific Function |
The expression of MIF at sites of inflammation suggest a role for the mediator in regulating the function of macrophage in host defense. Also acts as a phenylpyruvate tautomerase |
| Enzyme 1 Pathways |
|
| Enzyme 1 Reactions |
- keto-phenylpyruvate = enol-phenylpyruvate
|
| Enzyme 1 Pfam Domain Function |
|
| Enzyme 1 Signals |
|
| Enzyme 1 Transmembrane Regions |
|
| Enzyme 1 Essentiality |
Not Available |
| Enzyme 1 GenBank ID Protein |
188556 |
| Enzyme 1 UniProtKB/Swiss-Prot ID |
P14174 |
| Enzyme 1 UniProtKB/Swiss-Prot Entry Name |
MIF_HUMAN |
| Enzyme 1 PDB ID |
1GIF |
| Enzyme 1 PDB File |
Show |
| Enzyme 1 3D Structure |
|
| Enzyme 1 Cellular Location |
Not Available |
| Enzyme 1 Gene Sequence |
>348 bp
ATGCCGATGTTCATCGTAAACACCAACGTGCCCCGCGCCTCCGTGCCGGACGGGTTCCTC
TCCGAGCTCACCCAGCAGCTGGCGCAGGCCACCGGCAAGCCCCCCCAGTACATCGCGGTG
CACGTGGTCCCGGACCAGCTCATGGCCTTCGGCGGCTCCAGCGAGCCGTGCGCGCTCTGC
AGCCTGCACAGCATCGGCAAGATCGGCGGCGCGCAGAACCGCTCCTACAGCAAGCTGCTG
TGCGGCCTGCTGGCCGAGCGCCTGCGCATCAGCCCGGACAGGGTCTACATCAACTATTAC
GACATGAACGCGGCCAGTGTGGGCTGGAACAACTCCACCTTCGCCTAA
|
| Enzyme 1 GenBank Gene ID |
M25639 |
| Enzyme 1 GeneCard ID |
MIF |
| Enzyme 1 GenAtlas ID |
MIF |
| Enzyme 1 HGNC ID |
HGNC:7097 |
| Enzyme 1 Chromosome Location |
22 |
| Enzyme 1 Locus |
22q11.23 |
| Enzyme 1 SNPs |
SNPJam Report |
| Enzyme 1 General References |
- Weiser WY, Temple PA, Witek-Giannotti JS, Remold HG, Clark SC, David JR: Molecular cloning of a cDNA encoding a human macrophage migration inhibitory factor. Proc Natl Acad Sci U S A. 1989 Oct;86(19):7522-6. [PubMed ]
- Mikayama T, Nakano T, Gomi H, Nakagawa Y, Liu YC, Sato M, Iwamatsu A, Ishii Y, Weiser WY, Ishizaka K: Molecular cloning and functional expression of a cDNA encoding glycosylation-inhibiting factor. Proc Natl Acad Sci U S A. 1993 Nov 1;90(21):10056-60. [PubMed ]
- Paralkar V, Wistow G: Cloning the human gene for macrophage migration inhibitory factor (MIF). Genomics. 1994 Jan 1;19(1):48-51. [PubMed ]
- Bernhagen J, Mitchell RA, Calandra T, Voelter W, Cerami A, Bucala R: Purification, bioactivity, and secondary structure analysis of mouse and human macrophage migration inhibitory factor (MIF). Biochemistry. 1994 Nov 29;33(47):14144-55. [PubMed ]
- Wistow GJ, Shaughnessy MP, Lee DC, Hodin J, Zelenka PS: A macrophage migration inhibitory factor is expressed in the differentiating cells of the eye lens. Proc Natl Acad Sci U S A. 1993 Feb 15;90(4):1272-5. [PubMed ]
- Hochstrasser DF, Frutiger S, Paquet N, Bairoch A, Ravier F, Pasquali C, Sanchez JC, Tissot JD, Bjellqvist B, Vargas R, et al.: Human liver protein map: a reference database established by microsequencing and gel comparison. Electrophoresis. 1992 Dec;13(12):992-1001. [PubMed ]
- Zeng FY, Weiser WY, Kratzin H, Stahl B, Karas M, Gabius HJ: The major binding protein of the interferon antagonist sarcolectin in human placenta is a macrophage migration inhibitory factor. Arch Biochem Biophys. 1993 May 15;303(1):74-80. [PubMed ]
- Gevaert K, Goethals M, Martens L, Van Damme J, Staes A, Thomas GR, Vandekerckhove J: Exploring proteomes and analyzing protein processing by mass spectrometric identification of sorted N-terminal peptides. Nat Biotechnol. 2003 May;21(5):566-9. Epub 2003 Mar 31. [PubMed ]
- Kleemann R, Hausser A, Geiger G, Mischke R, Burger-Kentischer A, Flieger O, Johannes FJ, Roger T, Calandra T, Kapurniotu A, Grell M, Finkelmeier D, Brunner H, Bernhagen J: Intracellular action of the cytokine MIF to modulate AP-1 activity and the cell cycle through Jab1. Nature. 2000 Nov 9;408(6809):211-6. [PubMed ]
- Shen L, Hu J, Lu H, Wu M, Qin W, Wan D, Li YY, Gu J: The apoptosis-associated protein BNIPL interacts with two cell proliferation-related proteins, MIF and GFER. FEBS Lett. 2003 Apr 10;540(1-3):86-90. [PubMed ]
- Sugimoto H, Suzuki M, Nakagawa A, Tanaka I, Nishihira J: Crystal structure of macrophage migration inhibitory factor from human lymphocyte at 2.1 A resolution. FEBS Lett. 1996 Jul 1;389(2):145-8. [PubMed ]
- Kato Y, Muto T, Tomura T, Tsumura H, Watarai H, Mikayama T, Ishizaka K, Kuroki R: The crystal structure of human glycosylation-inhibiting factor is a trimeric barrel with three 6-stranded beta-sheets. Proc Natl Acad Sci U S A. 1996 Apr 2;93(7):3007-10. [PubMed ]
- Sun HW, Bernhagen J, Bucala R, Lolis E: Crystal structure at 2.6-A resolution of human macrophage migration inhibitory factor. Proc Natl Acad Sci U S A. 1996 May 28;93(11):5191-6. [PubMed ]
- Lubetsky JB, Swope M, Dealwis C, Blake P, Lolis E: Pro-1 of macrophage migration inhibitory factor functions as a catalytic base in the phenylpyruvate tautomerase activity. Biochemistry. 1999 Jun 1;38(22):7346-54. [PubMed ]
|
| Enzyme 1 Metabolite References |
Not Available |
|
Enzyme 2
[top]
|
| Enzyme 2 ID |
16510 |
| Enzyme 2 Name |
cDNA, FLJ92196, Homo sapiens macrophage migration inhibitory factor(glycosylation-inhibiting factor) (MIF), mRNA (Macrophage migration inhibitory factor) (Glycosylation-inhibiting factor) |
| Enzyme 2 Synonyms |
Not Available |
| Enzyme 2 Gene Name |
MIF |
| Enzyme 2 Protein Sequence |
>cDNA, FLJ92196, Homo sapiens macrophage migration inhibitory factor(glycosylation-inhibiting factor) (MIF), mRNA (Macrophage migration inhibitory factor) (Glycosylation-inhibiting factor)
MPMFIVNTNVPRASVPDGFLSELTQQLAQATGKPPQYIAVHVVPDQLMAFGGSSEPCALC
SLHSIGKIGGAQNRSYSKLLCGLLAERLRISPDRVYINYYDMNAANVGWNNSTFA
|
| Enzyme 2 Number of Residues |
115 |
| Enzyme 2 Molecular Weight |
12476 |
| Enzyme 2 Theoretical pI |
8.05 |
| Enzyme 2 GO Classification |
Not Available |
| Enzyme 2 General Function |
Not Available |
| Enzyme 2 Specific Function |
Not Available |
| Enzyme 2 Pathways |
Not Available |
| Enzyme 2 Reactions |
Not Available |
| Enzyme 2 Pfam Domain Function |
|
| Enzyme 2 Signals |
|
| Enzyme 2 Transmembrane Regions |
|
| Enzyme 2 Essentiality |
Not Available |
| Enzyme 2 GenBank ID Protein |
Not Available |
| Enzyme 2 UniProtKB/Swiss-Prot ID |
B2R4S3 |
| Enzyme 2 UniProtKB/Swiss-Prot Entry Name |
B2R4S3_HUMAN |
| Enzyme 2 PDB ID |
1GIF |
| Enzyme 2 PDB File |
Show |
| Enzyme 2 3D Structure |
|
| Enzyme 2 Cellular Location |
Not Available |
| Enzyme 2 Gene Sequence |
Not Available |
| Enzyme 2 GenBank Gene ID |
AK311929 |
| Enzyme 2 GeneCard ID |
B2R4S3 |
| Enzyme 2 GenAtlas ID |
Not Available |
| Enzyme 2 HGNC ID |
Not Available |
| Enzyme 2 Chromosome Location |
22 |
| Enzyme 2 Locus |
22q11.23 |
| Enzyme 2 SNPs |
SNPJam Report |
| Enzyme 2 General References |
Not Available |
| Enzyme 2 Metabolite References |
Not Available |
