{"ymdb_id":"YMDB00322","created_at":"2011-05-29T18:06:04.000Z","updated_at":"2016-10-18T17:11:26.000Z","name":"Dihydroxyacetone phosphate","cas":"57-04-5","state":"Solid","melting_point":"","description":"Dihydroxyacetone phosphate (DHAP) is an important intermediate in lipid biosynthesis and in glycolysis.\nDihydroxyacetone phosphate is one of the two products of breakdown of fructose 1,6-bisphosphate, along with glyceraldehyde 3-phosphate. It is rapidly and reversibly isomerised to glyceraldehyde 3-phosphate. DHAP is also the product of the dehydrogenation of L-glycerol-3-phosphate, which is part of the entry of glycerol (sourced from triglycerides) into the glycolytic pathway. [Wikipedia]","experimental_water_solubility":"","experimental_logp_hydrophobicity":"","location":"mitochondrion;lipid particle;endoplasmic reticulum;cytoplasm","synthesis_reference":"Ballou, Clinton E.; Fischer, Hermann O. L. The synthesis of dihydroxyacetone phosphate. Journal of the American Chemical Society (1956), 78 1659-61.","chebi_id":"16108","hmdb_id":"HMDB01473","kegg_id":"C00111","pubchem_id":"668","cs_id":"648","foodb_id":null,"wikipedia_link":"Dihydroxyacetone_phosphate","biocyc_id":"DIHYDROXY-ACETONE-PHOSPHATE","iupac":"(3-hydroxy-2-oxopropoxy)phosphonic acid","traditional_iupac":"dihydroxyacetone-phosphate","logp":"-1.6517823150000002","pka":"6.220373471836065","alogps_solubility":"2.19e+01 g/l","alogps_logp":"-1.49","alogps_logs":"-0.89","acceptor_count":"5","donor_count":"3","rotatable_bond_count":"4","polar_surface_area":"104.06","refractivity":"30.472099999999998","polarizability":"12.641516377396067","formal_charge":"0","physiological_charge":"-2","pka_strongest_basic":"-3.3227461112640855","pka_strongest_acidic":"1.1902795898513006","bioavailability":"1","number_of_rings":"0","rule_of_five":"1","ghose_filter":"0","veber_rule":"0","mddr_like_rule":"0","synonyms":["1-hydroxy-3-(phosphonooxy)-2-Propanone","1-Hydroxy-3-(phosphonooxy)acetone","1,3-dihydroxy-2-Propanone mono(dihydrogen phosphate)","1,3-Dihydroxy-2-propanone phosphate","1,3-Dihydroxyacetone 1-phosphate","DHAP","di-OH-acetone-P","Dihydroxy-Acetone-P","dihydroxy-acetone-phosphate","dihydroxyacetone 3-phosphate","Dihydroxyacetone monophosphate","Dihydroxyacetone phosphate","Dihydroxyacetone phosphic acid","dihydroxyacetone-P","dihydroxyacetone-phosphate","Glycerone phosphate","glycerone-phosphate","Phosphoric 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glucose","concentration":"330.0","concentration_units":"\u0026#181;M","error":"10.0"},{"growth_media":"Synthetic medium with 2% glucose","concentration":"120.0","concentration_units":"\u0026#181;M","error":"10.0"},{"growth_media":"Synthetic medium with 2% galactose","concentration":"460.0","concentration_units":"\u0026#181;M","error":"70.0"}],"references":[{"pubmed_id":21051339,"citation":"UniProt Consortium (2011). \"Ongoing and future developments at the Universal Protein Resource.\" Nucleic Acids Res 39:D214-D219."},{"pubmed_id":21062828,"citation":"Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). \"BRENDA, the enzyme information system in 2011.\" Nucleic Acids Res 39:D670-D676."},{"pubmed_id":18846089,"citation":"Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). \"A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology.\" Nat Biotechnol 26:1155-1160."},{"pubmed_id":7878741,"citation":"Thevelein, J. M., Hohmann, S. (1995). \"Trehalose synthase: guard to the gate of glycolysis in yeast?\" Trends Biochem Sci 20:3-10."},{"pubmed_id":10935926,"citation":"Vaseghi, S., Baumeister, A., Rizzi, M., Reuss, M. (1999). \"In vivo dynamics of the pentose phosphate pathway in Saccharomyces cerevisiae.\" Metab Eng 1:128-140."},{"pubmed_id":10049376,"citation":"Athenstaedt, K., Weys, S., Paltauf, F., Daum, G. (1999). \"Redundant systems of phosphatidic acid biosynthesis via acylation of glycerol-3-phosphate or dihydroxyacetone phosphate in the yeast Saccharomyces cerevisiae.\" J Bacteriol 181:1458-1463."},{"pubmed_id":8435847,"citation":"Boles, E., Zimmermann, F. K. (1993). \"Saccharomyces cerevisiae phosphoglucose isomerase and fructose bisphosphate aldolase can be replaced functionally by the corresponding enzymes of Escherichia coli and Drosophila melanogaster.\" Curr Genet 23:187-191."},{"pubmed_id":11544256,"citation":"Zheng, Z., Zou, J. (2001). \"The initial step of the glycerolipid pathway: identification of glycerol 3-phosphate/dihydroxyacetone phosphate dual substrate acyltransferases in Saccharomyces cerevisiae.\" J Biol Chem 276:41710-41716."},{"pubmed_id":8196651,"citation":"Albertyn, J., Hohmann, S., Thevelein, J. M., Prior, B. A. (1994). \"GPD1, which encodes glycerol-3-phosphate dehydrogenase, is essential for growth under osmotic stress in Saccharomyces cerevisiae, and its expression is regulated by the high-osmolarity glycerol response pathway.\" Mol Cell Biol 14:4135-4144."},{"pubmed_id":3908097,"citation":"Inoue, Y., Watanabe, K., Shimosaka, M., Saikusa, T., Fukuda, Y., Murata, K., Kimura, A. (1985). \"Metabolism of 2-oxoaldehydes in yeasts. Purification and characterization of lactaldehyde dehydrogenase from Saccharomyces cerevisiae.\" Eur J Biochem 153:243-247."},{"pubmed_id":6229402,"citation":"Lagunas, R., Gancedo, C. (1983). \"Role of phosphate in the regulation of the Pasteur effect in Saccharomyces cerevisiae.\" Eur J Biochem 137:479-483."}],"proteins":[{"created_at":"2011-05-24T20:16:09.000Z","updated_at":"2011-07-22T17:54:38.000Z","name":"Dihydroxyacetone kinase 2","uniprot_id":"P43550","uniprot_name":"DAK2_YEAST","enzyme":true,"transporter":false,"gene_name":"DAK2","num_residues":591,"molecular_weight":"62134.0","theoretical_pi":"5.67","general_function":"Involved in glycerone kinase activity","specific_function":"ATP + glycerone = ADP + glycerone phosphate","reactions":[{"id":1465,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2308,"direction":"\u003e","locations":"","altext":"ATP + glycerone = ADP + glycerone phosphate.","export":false,"pw_reaction_id":null,"source":null},{"id":3899,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006416","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":null,"genbank_gene_id":"D50617","genbank_protein_id":"836702","gene_card_id":"DAK2","chromosome_location":"chromosome 6","locus":"YFL053W","synonyms":["DHA kinase 2","Glycerone kinase 2"],"enzyme_classes":["2.7.1.29"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" nucleoside binding"},{"category":"Function","description":" purine nucleoside binding"},{"category":"Function","description":" adenyl nucleotide binding"},{"category":"Function","description":" adenyl ribonucleotide binding"},{"category":"Function","description":" ATP binding"},{"category":"Function","description":" kinase activity"},{"category":"Function","description":" glycerone kinase activity"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" transferase activity"},{"category":"Function","description":" transferase activity, transferring phosphorus-containing groups"},{"category":"Function","description":" binding"},{"category":"Process","description":" small molecule metabolic process"},{"category":"Process","description":" alcohol metabolic process"},{"category":"Process","description":" polyol metabolic process"},{"category":"Process","description":" alditol metabolic process"},{"category":"Process","description":" glycerol metabolic process"},{"category":"Process","description":" metabolic process"}],"pfams":[{"name":"Dak1","identifier":"PF02733"},{"name":"Dak2","identifier":"PF02734"}],"pathways":[{"name":"Glycerolipid metabolism","kegg_map_id":"00561"},{"name":"Methane metabolism","kegg_map_id":"00680"},{"name":"Glycerol 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Available"},{"category":"Function","description":" nucleoside binding"},{"category":"Function","description":" purine nucleoside binding"},{"category":"Function","description":" adenyl nucleotide binding"},{"category":"Function","description":" adenyl ribonucleotide binding"},{"category":"Function","description":" ATP binding"},{"category":"Function","description":" kinase activity"},{"category":"Function","description":" glycerone kinase activity"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" transferase activity"},{"category":"Function","description":" transferase activity, transferring phosphorus-containing groups"},{"category":"Function","description":" binding"},{"category":"Process","description":" small molecule metabolic process"},{"category":"Process","description":" alcohol metabolic process"},{"category":"Process","description":" polyol metabolic process"},{"category":"Process","description":" alditol metabolic process"},{"category":"Process","description":" glycerol metabolic process"},{"category":"Process","description":" metabolic process"}],"pfams":[{"name":"Dak1","identifier":"PF02733"},{"name":"Dak2","identifier":"PF02734"}],"pathways":[{"name":"Glycerolipid metabolism","kegg_map_id":"00561"},{"name":"Methane 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D-glyceraldehyde 3-phosphate.","export":false,"pw_reaction_id":null,"source":null}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":null,"genbank_gene_id":"X15003","genbank_protein_id":"3696","gene_card_id":"FBA1","chromosome_location":"chromosome 11","locus":"YKL060C","synonyms":["FBP aldolase","FBPA","Fructose-1,6-bisphosphate aldolase"],"enzyme_classes":["4.1.2.13"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" ion binding"},{"category":"Function","description":" cation binding"},{"category":"Function","description":" metal ion binding"},{"category":"Function","description":" transition metal ion binding"},{"category":"Function","description":" zinc ion binding"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" aldehyde-lyase activity"},{"category":"Function","description":" fructose-bisphosphate aldolase activity"},{"category":"Function","description":" lyase activity"},{"category":"Function","description":" carbon-carbon lyase activity"},{"category":"Function","description":" binding"},{"category":"Process","description":" small molecule metabolic process"},{"category":"Process","description":" alcohol metabolic process"},{"category":"Process","description":" monosaccharide metabolic process"},{"category":"Process","description":" hexose metabolic process"},{"category":"Process","description":" glucose metabolic process"},{"category":"Process","description":" glucose catabolic process"},{"category":"Process","description":" glycolysis"},{"category":"Process","description":" metabolic process"}],"pfams":[{"name":"F_bP_aldolase","identifier":"PF01116"}],"pathways":[{"name":"Glycolysis / Gluconeogenesis","kegg_map_id":"00010"},{"name":"Pentose phosphate pathway","kegg_map_id":"00030"},{"name":"Fructose and mannose metabolism","kegg_map_id":"00051"},{"name":"Methane metabolism","kegg_map_id":"00680"}],"gene_sequence":"ATGGGTGTTGAACAAATCTTAAAGAGAAAGACCGGTGTCATCGTTGGTGAAGATGTCCACAACTTATTCACTTACGCTAAGGAACACAAGTTCGCTATTCCAGCTATTAACGTCACCTCTTCTTCTACTGCCGTCGCTGCTTTAGAAGCTGCTAGAGACAGCAAGTCCCCAATCATTTTGCAAACCTCTAACGGTGGTGCTGCTTACTTCGCTGGTAAGGGTATCTCTAACGAAGGTCAAAATGCTTCCATCAAGGGTGCTATTGCCGCTGCCCACTACATCAGATCCATTGCTCCAGCTTACGGTATCCCAGTTGTCTTACACTCTGACCACTGTGCCAAGAAGTTGTTGCCATGGTTCGATGGTATGTTGGAAGCTGATGAAGCTTACTTCAAGGAACACGGTGAACCATTATTCTCCTCCCACATGTTGGATTTGTCTGAAGAAACCGATGAAGAAAACATCTCTACTTGTGTCAAGTACTTCAAGAGAATGGCCGCTATGGACCAATGGTTAGAAATGGAAATCGGTATTACCGGTGGTGAAGAAGATGGTGTTAACAACGAAAACGCTGACAAGGAAGACTTGTACACCAAGCCAGAACAAGTTTACAACGTCTACAAGGCTTTGCACCCAATCTCTCCAAACTTCTCCATTGCTGCTGCTTTCGGTAACTGTCACGGTTTGTACGCTGGTGACATCGCTTTGAGACCAGAAATCTTGGCTGAACACCAAAAGTACACCAGAGAACAAGTTGGTTGCAAGGAAGAAAAGCCATTGTTCTTGGTCTTCCACGGTGGTTCCGGTTCTACTGTCCAAGAATTCCACACTGGTATTGACAACGGTGTTGTCAAGGTCAACTTGGACACTGACTGTCAATACGCTTACTTGACTGGTATCAGAGACTACGTCTTGAACAAGAAGGACTACATAATGTCCCCAGTCGGTAACCCAGAAGGTCCAGAAAAGCCAAACAAGAAGTTCTTCGACCCAAGAGTCTGGGTTAGAGAAGGTGAAAAGACCATGGGTGCTAAGATCACCAAGTCTTTGGAAACTTTCCGTACCACTAACACTTTATAA","protein_sequence":"MGVEQILKRKTGVIVGEDVHNLFTYAKEHKFAIPAINVTSSSTAVAALEAARDSKSPIILQTSNGGAAYFAGKGISNEGQNASIKGAIAAAHYIRSIAPAYGIPVVLHSDHCAKKLLPWFDGMLEADEAYFKEHGEPLFSSHMLDLSEETDEENISTCVKYFKRMAAMDQWLEMEIGITGGEEDGVNNENADKEDLYTKPEQVYNVYKALHPISPNFSIAAAFGNCHGLYAGDIALRPEILAEHQKYTREQVGCKEEKPLFLVFHGGSGSTVQEFHTGIDNGVVKVNLDTDCQYAYLTGIRDYVLNKKDYIMSPVGNPEGPEKPNKKFFDPRVWVREGEKTMGAKITKSLETFRTTNTL"},{"created_at":"2011-05-27T02:06:00.000Z","updated_at":"2011-05-29T05:06:35.000Z","name":"Triosephosphate isomerase","uniprot_id":"P00942","uniprot_name":"TPIS_YEAST","enzyme":true,"transporter":false,"gene_name":"TPI1","num_residues":248,"molecular_weight":"26795.30078","theoretical_pi":"5.81","general_function":"Involved in catalytic activity","specific_function":"D-glyceraldehyde 3-phosphate = glycerone phosphate","reactions":[{"id":2022,"direction":"\u003c\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2659,"direction":"\u003e","locations":null,"altext":"D-glyceraldehyde 3-phosphate = glycerone phosphate.","export":false,"pw_reaction_id":null,"source":null},{"id":3809,"direction":"\u003c\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006323","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":"1YPI","cellular_location":null,"genbank_gene_id":"AY557654","genbank_protein_id":"45269201","gene_card_id":"TPI1","chromosome_location":"chromosome 4","locus":"YDR050C","synonyms":["TIM","Triose-phosphate isomerase"],"enzyme_classes":["5.3.1.1"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" triose-phosphate isomerase activity"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" isomerase activity"},{"category":"Function","description":" intramolecular oxidoreductase activity"},{"category":"Function","description":" intramolecular oxidoreductase activity, interconverting aldoses and ketoses"},{"category":"Process","description":" metabolic process"}],"pfams":[{"name":"TIM","identifier":"PF00121"}],"pathways":[{"name":"Glycolysis / Gluconeogenesis","kegg_map_id":"00010"},{"name":"Fructose and mannose metabolism","kegg_map_id":"00051"},{"name":"Inositol phosphate metabolism","kegg_map_id":"00562"},{"name":"Glycolysis I","kegg_map_id":null}],"gene_sequence":"ATGGCTAGAACTTTCTTTGTCGGTGGTAACTTTAAATTAAACGGTTCCAAACAATCCATTAAGGAAATTGTTGAAAGATTGAACACTGCTTCTATCCCAGAAAATGTCGAGGTTGTTATCTGTCCTCCAGCTACCTACTTAGACTACTCTGTCTCTTTGGTTAAGAAGCCACAAGTCACTGTCGGTGCTCAAAACGCCTACTTGAAGGCTTCTGGTGCTTTCACCGGTGAAAACTCCGTTGACCAAATCAAGGATGTTGGTGCTAAGTGGGTTATTTTGGGTCACTCCGAAAGAAGATCTTACTTCCACGAAGATGACAAGTTCATTGCTGACAAGACCAAGTTCGCTTTAGGTCAAGGTGTCGGTGTCATCTTGTGTATCGGTGAAACTTTGGAAGAAAAGAAGGCCGGTAAGACTTTGGATGTTGTTGAAAGACAATTGAACGCTGTCTTGGAAGAAGTTAAGGACTGGACTAACGTCGTTGTCGCTTACGAACCAGTCTGGGCCATTGGTACCGGTTTGGCTGCTACTCCAGAAGATGCTCAAGATATTCACGCTTCCATCAGAAAGTTCTTGGCTTCCAAGTTGGGTGACAAGGCTGCCAGCGAATTGAGAATCTTATACGGTGGTTCCGCTAACGGTAGCAACGCCGTTACCTTCAAGGACAAGGCTGATGTCGATGGTTTCTTGGTCGGTGGTGCTTCTTTGAAGCCAGAATTTGTTGATATCATCAACTCTAGAAACTAA","protein_sequence":"MARTFFVGGNFKLNGSKQSIKEIVERLNTASIPENVEVVICPPATYLDYSVSLVKKPQVTVGAQNAYLKASGAFTGENSVDQIKDVGAKWVILGHSERRSYFHEDDKFIADKTKFALGQGVGVILCIGETLEEKKAGKTLDVVERQLNAVLEEVKDWTNVVVAYEPVWAIGTGLAATPEDAQDIHASIRKFLASKLGDKAASELRILYGGSANGSNAVTFKDKADVDGFLVGGASLKPEFVDIINSRN"}]}