{"ymdb_id":"YMDB00079","created_at":"2011-05-29T15:54:39.000Z","updated_at":"2016-09-08T18:34:59.000Z","name":"Dihydrofolic acid","cas":"4033-27-6","state":"Solid","melting_point":"","description":"Dihydrofolic acid is a folic acid derivative acted upon by dihydrofolate reductase to produce tetrahydrofolic acid. Tetrahydrofolate is needed to make both purines and pyrimidines. Dihydrofolic acid is also known by the name dihydrofolate - more commonly vitamin B9. [Wikipedia]","experimental_water_solubility":"","experimental_logp_hydrophobicity":null,"location":"mitochondrion;cytoplasm","synthesis_reference":"Smith, Karin; Scrimgeour, K. G.; Huennekens, F. M.  Folic acid coenzymes and one-carbon metabolism. XV. Synthesis of a new form of dihydrofolate.    Biochemical and Biophysical Research Communications  (1963),  11(5),  388-92.","chebi_id":"15633","hmdb_id":"HMDB01056","kegg_id":"C00415","pubchem_id":"98792","cs_id":"89228","foodb_id":null,"wikipedia_link":"Dihydrofolic acid","biocyc_id":"DIHYDROFOLATE","iupac":"(2S)-2-[(4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid","traditional_iupac":"dihydrofolic acid","logp":"-1.7816132694652138","pka":"4.17230491299049","alogps_solubility":"1.41e-01 g/l","alogps_logp":"-0.93","alogps_logs":"-3.50","acceptor_count":"12","donor_count":"7","rotatable_bond_count":"9","polar_surface_area":"207.60000000000002","refractivity":"120.9914","polarizability":"44.310029663024785","formal_charge":"0","physiological_charge":"-2","pka_strongest_basic":"2.0926310636850247","pka_strongest_acidic":"3.373110634106839","bioavailability":"0","number_of_rings":"3","rule_of_five":"0","ghose_filter":"0","veber_rule":"0","mddr_like_rule":"1","synonyms":["7,8-Dihydro-L-folic acid","7,8-dihydrofolate","7,8-Dihydrofolic acid","7,8-Dihydropteroylglutamate","dihydrofolate","H2PteGlu","H2PteGlu1","L-N-[p-[[(2-amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-Glutamic acid","N-(4-(((2-amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-Glutamic acid","N-(4-{[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid","N-(7,8-dihydropteroyl)-L-glutamic acid","N-[4-[[(2-amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-Glutamic acid","N-[4-[[(2-amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-Glutamic acid"],"pathways":[{"name":"Folate biosynthesis","kegg_map_id":"00790"},{"name":"One carbon pool by folate","kegg_map_id":"00670"},{"name":"One Carbon Pool by Folate I","kegg_map_id":null},{"name":"Pyrimidine metabolism","kegg_map_id":"00240"}],"growth_conditions":[],"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":11731153,"citation":"Bayly, A. M., Berglez, J. M., Patel, O., Castelli, L. A., Hankins, E. G., Coloe, P., Hopkins Sibley, C., Macreadie, I. G. (2001). \"Folic acid utilisation related to sulfa drug resistance in Saccharomyces cerevisiae.\" FEMS Microbiol Lett 204:387-390."}],"proteins":[{"created_at":"2011-05-26T17:49:27.000Z","updated_at":"2011-07-22T17:54:37.000Z","name":"Dihydrofolate reductase","uniprot_id":"P07807","uniprot_name":"DYR_YEAST","enzyme":true,"transporter":false,"gene_name":"DFR1","num_residues":211,"molecular_weight":"24260.80078","theoretical_pi":"8.05","general_function":"Involved in dihydrofolate reductase activity","specific_function":"Key enzyme in folate metabolism. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis","reactions":[{"id":1455,"direction":"\u003e","locations":"mitochondrion;cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2485,"direction":"\u003e","locations":null,"altext":"5,6,7,8-tetrahydrofolate + NADP(+) = 7,8-dihydrofolate + NADPH.","export":false,"pw_reaction_id":null,"source":null},{"id":4147,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006448","source":"Smpdb"},{"id":4148,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006675","source":"Smpdb"},{"id":4149,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006676","source":"Smpdb"},{"id":4150,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006677","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":null,"genbank_gene_id":"M18578","genbank_protein_id":"171397","gene_card_id":"DFR1","chromosome_location":"chromosome 15","locus":"YOR236W","synonyms":[],"enzyme_classes":["1.5.1.3"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" NADP or NADPH binding"},{"category":"Function","description":" oxidoreductase activity, acting on the CH-NH group of donors"},{"category":"Function","description":" oxidoreductase activity, acting on the CH-NH group of donors, NAD or NADP as acceptor"},{"category":"Function","description":" dihydrofolate reductase activity"},{"category":"Function","description":" binding"},{"category":"Function","description":" nucleotide binding"},{"category":"Function","description":" oxidoreductase activity"},{"category":"Function","description":" catalytic activity"},{"category":"Process","description":" nitrogen compound metabolic process"},{"category":"Process","description":" cellular nitrogen compound metabolic process"},{"category":"Process","description":" nucleobase, nucleoside, nucleotide and nucleic acid metabolic process"},{"category":"Process","description":" nucleobase, nucleoside and nucleotide metabolic process"},{"category":"Process","description":" nucleoside phosphate metabolic process"},{"category":"Process","description":" nucleotide biosynthetic process"},{"category":"Process","description":" nucleotide metabolic process"},{"category":"Process","description":" glycine biosynthetic process"},{"category":"Process","description":" cellular metabolic process"},{"category":"Process","description":" cellular amino acid and derivative metabolic process"},{"category":"Process","description":" cellular amino acid metabolic process"},{"category":"Process","description":" oxidation reduction"},{"category":"Process","description":" serine family amino acid metabolic process"},{"category":"Process","description":" metabolic process"},{"category":"Process","description":" glycine metabolic process"}],"pfams":[{"name":"DHFR_1","identifier":"PF00186"}],"pathways":[{"name":"One carbon pool by folate","kegg_map_id":"00670"},{"name":"Folate biosynthesis","kegg_map_id":"00790"},{"name":"tetrahydrofolate biosynthesis","kegg_map_id":null}],"gene_sequence":"ATGGCTGGAGGAAAGATTCCTATTGTAGGAATTGTGGCATGTTTACAGCCGGAGATGGGGATAGGATTTCGTGGAGGTCTACCATGGAGGTTGCCCAGTGAAATGAAGTATTTCAGACAGGTCACTTCATTGACGAAAGATCCAAACAAAAAAAATGCTTTGATAATGGGAAGGAAGACATGGGAATCCATACCGCCCAAGTTTCGCCCACTGCCCAATAGAATGAATGTCATTATATCGAGAAGCTTCAAGGACGATTTTGTCCACGATAAAGAGAGATCAATAGTCCAAAGTAATTCATTGGCAAACGCAATAATGAACCTAGAAAGCAATTTTAAGGAGCATCTGGAAAGAATCTACGTGATTGGGGGTGGCGAAGTTTATAGTCAAATCTTCTCCATTACAGATCATTGGCTCATCACGAAAATAAATCCATTAGATAAAAACGCAACTCCTGCAATGGACACTTTCCTTGATGCGAAGAAATTGGAAGAAGTATTTAGCGAGCAAGATCCGGCCCAGCTGAAAGAATTTCTTCCCCCTAAAGTAGAGTTGCCCGAAACAGACTGTGATCAACGCTACTCGCTGGAAGAAAAAGGTTATTGCTTCGAATTCACTCTATACAATCGTAAATGA","protein_sequence":"MAGGKIPIVGIVACLQPEMGIGFRGGLPWRLPSEMKYFRQVTSLTKDPNKKNALIMGRKTWESIPPKFRPLPNRMNVIISRSFKDDFVHDKERSIVQSNSLANAIMNLESNFKEHLERIYVIGGGEVYSQIFSITDHWLITKINPLDKNATPAMDTFLDAKKLEEVFSEQDPAQLKEFLPPKVELPETDCDQRYSLEEKGYCFEFTLYNRK"},{"created_at":"2011-05-26T17:50:01.000Z","updated_at":"2011-07-22T17:54:37.000Z","name":"Folylpolyglutamate synthase 1","uniprot_id":"Q12676","uniprot_name":"FOLD_YEAST","enzyme":true,"transporter":false,"gene_name":"FOL3","num_residues":427,"molecular_weight":"47850.80078","theoretical_pi":"6.82","general_function":"Involved in tetrahydrofolylpolyglutamate synthase activity","specific_function":"Conversion of folates to polyglutamate derivatives","reactions":[{"id":1456,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2486,"direction":"\u003e","locations":"Cytoplasm;Mitochondrion. Cytoplasm;Mitochondrion","altext":"ATP + tetrahydropteroyl-(gamma-Glu)(n) + L-glutamate = ADP + phosphate + tetrahydropteroyl-(gamma-Glu)(n+1).","export":false,"pw_reaction_id":null,"source":null},{"id":4146,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006447","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":"Cytoplasm","genbank_gene_id":"Z49702","genbank_protein_id":"817872","gene_card_id":"FOL3","chromosome_location":"chromosome 13","locus":"YMR113W","synonyms":["Folylpoly-gamma-glutamate synthetase","FPGS","Tetrahydrofolylpolyglutamate synthase","Tetrahydrofolate synthase"],"enzyme_classes":["6.3.2.17"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" ligase activity"},{"category":"Function","description":" ligase activity, forming carbon-nitrogen bonds"},{"category":"Function","description":" binding"},{"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":" acid-amino acid ligase activity"},{"category":"Function","description":" tetrahydrofolylpolyglutamate synthase activity"},{"category":"Function","description":" catalytic activity"},{"category":"Process","description":" biosynthetic process"},{"category":"Process","description":" cellular metabolic process"},{"category":"Process","description":" cellular aromatic compound metabolic process"},{"category":"Process","description":" folic acid and derivative metabolic process"},{"category":"Process","description":" metabolic process"},{"category":"Process","description":" folic acid and derivative biosynthetic process"}],"pfams":[{"name":"Mur_ligase_M","identifier":"PF08245"}],"pathways":[{"name":"Folate biosynthesis","kegg_map_id":"00790"},{"name":"tetrahydrofolate biosynthesis","kegg_map_id":null}],"gene_sequence":"ATGGCCATTGAATTGGGACTTTCCCGTATTACAAAACTACTAGAGCATTTAGGCAATCCGCAAAACTCACTTAGAGTGCTGCACATTGCAGGGACAAATGGTAAAGGTTCAGTATGTACTTACCTATCTTCTGTGTTGCAACAAAAGTCCTACCAAATTGGAAAATTTACCACTCCACACTTGGTGCATGTTACTGATTCCATTACAATCAACAATAAGCCGATTCCGTTAGAGAGATACCAGAATATTAGATTACAACTAGAAGCTTTAAACAAGTCACACTCTTTAAAATGTACGGAATTCGAGCTATTAACATGTACCGCATTCAAATATTTTTATGATGTGCAGTGCCAATGGTGTGTCATAGAAGTAGGCCTTGGCGGAAGACTTGATGCGACCAATGTTATTCCAGGCGCAAATAAGGCATGTTGTGGTATTACTAAAATCAGTTTGGATCATGAAAGCTTTTTAGGTAACACCTTGTCTGAAATCTCTAAAGAGAAAGCAGGTATAATAACAGAAGGGGTACCCTTCACAGTGATTGATGGAACCAATGAGGCAAGTGTTATAAATGTTGTGAAAGAAAGATGCAAGGCTTTAGGGTCTGAACTATCCGTTACAGATTCTCAACTTAACGGAAATATGATTGACACCAACTCCTGGGGTTGTTTTGACTTGGCAAAATTGCCACTGAATGGAGAATATCAGATATTTAATCTCAGGGTGGCCATGGGTATGTTAGACTACTTACAAATGAACGAACTTATTGATATTACCAAGAATGAAGTAAGTACGAGATTGGCGAAGGTTGATTGGCCAGGAAGGTTATATCGTATGGATTATCGCTTTGACAAAGTAAGTAATAGGACAGTGCCTATATTAATGGACGGTGCCCACAATGGCTCAGCTGCAGTAGAGTTAGTTAAGTACCTAAGAAAGGAGTACGGAAACCAGCCTTTGACCTTTGTGATGGCAGTAACGCATGGGAAAAACTTGGAGCCGCTGCTCCAGCCATTATTGAGGCCTATAGATCAAGTAATTCTTACTCGGTTTAATAATGTGGAAGGTATGCCCTGGATTCATGCCACTGATCCTGAAGAAATAAAAGATTTTATTTTGACTCAAGGATACACAAAGGAGATAGTGATTGAAAATGATTTACATCAGGTATTGCCTTCTCTGGCGCATGTATCAGACGAGCAAAGACGGCCAATTGTTGTATGCGGTTCACTGTATTTATGTGGTGAATTATTACGGATTCACAATAGTCACTTGAGAAACTAA","protein_sequence":"MAIELGLSRITKLLEHLGNPQNSLRVLHIAGTNGKGSVCTYLSSVLQQKSYQIGKFTTPHLVHVTDSITINNKPIPLERYQNIRLQLEALNKSHSLKCTEFELLTCTAFKYFYDVQCQWCVIEVGLGGRLDATNVIPGANKACCGITKISLDHESFLGNTLSEISKEKAGIITEGVPFTVIDGTNEASVINVVKERCKALGSELSVTDSQLNGNMIDTNSWGCFDLAKLPLNGEYQIFNLRVAMGMLDYLQMNELIDITKNEVSTRLAKVDWPGRLYRMDYRFDKVSNRTVPILMDGAHNGSAAVELVKYLRKEYGNQPLTFVMAVTHGKNLEPLLQPLLRPIDQVILTRFNNVEGMPWIHATDPEEIKDFILTQGYTKEIVIENDLHQVLPSLAHVSDEQRRPIVVCGSLYLCGELLRIHNSHLRN"},{"created_at":"2011-05-26T17:50:40.000Z","updated_at":"2011-05-26T17:50:40.000Z","name":"Thymidylate synthase","uniprot_id":"P06785","uniprot_name":"TYSY_YEAST","enzyme":true,"transporter":false,"gene_name":"TMP1","num_residues":304,"molecular_weight":"35046.89844","theoretical_pi":"7.16","general_function":"Involved in thymidylate synthase activity","specific_function":"Required for both nuclear and mitochondrial DNA synthesis","reactions":[{"id":2013,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2487,"direction":"\u003e","locations":null,"altext":"5,10-methylenetetrahydrofolate + dUMP = dihydrofolate + dTMP.","export":false,"pw_reaction_id":null,"source":null},{"id":14234,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006678","source":"Smpdb"},{"id":14235,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006752","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":null,"genbank_gene_id":"J02706","genbank_protein_id":"172990","gene_card_id":"TMP1","chromosome_location":null,"locus":"YOR074C","synonyms":["TS","TSase"],"enzyme_classes":["2.1.1.45"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" transferase activity, transferring one-carbon groups"},{"category":"Function","description":" methyltransferase activity"},{"category":"Function","description":" 5,10-methylenetetrahydrofolate-dependent methyltransferase activity"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" thymidylate synthase activity"},{"category":"Function","description":" transferase activity"},{"category":"Process","description":" metabolic process"},{"category":"Process","description":" dTMP biosynthetic process"},{"category":"Process","description":" nitrogen compound metabolic process"},{"category":"Process","description":" cellular nitrogen compound metabolic process"},{"category":"Process","description":" nucleobase, nucleoside, nucleotide and nucleic acid metabolic process"},{"category":"Process","description":" nucleobase, nucleoside and nucleotide metabolic process"},{"category":"Process","description":" nucleoside phosphate metabolic process"},{"category":"Process","description":" nucleotide metabolic process"},{"category":"Process","description":" pyrimidine nucleotide metabolic process"},{"category":"Process","description":" pyrimidine nucleotide biosynthetic process"},{"category":"Process","description":" pyrimidine nucleoside monophosphate biosynthetic process"},{"category":"Process","description":" pyrimidine deoxyribonucleoside monophosphate biosynthetic process"}],"pfams":[{"name":"Thymidylat_synt","identifier":"PF00303"}],"pathways":[{"name":"Pyrimidine metabolism","kegg_map_id":"00240"},{"name":"One carbon pool by folate","kegg_map_id":"00670"},{"name":"One Carbon Pool by Folate I","kegg_map_id":null}],"gene_sequence":"ATGACTATGGACGGAAAAAACAAAGAAGAAGAGCAATATCTTGATCTATGCAAAAGAATCATTGATGAAGGTGAATTTAGGCCAGATAGAACAGGCACTGGTACGTTGAGTCTTTTTGCACCACCCCAGCTGCGTTTTAGTTTACGTGATGATACCTTCCCACTACTAACGACCAAGAAGGTTTTTACTAGAGGTATCATACTTGAACTATTGTGGTTTTTGGCCGGTGATACAGACGCTAACCTATTGTCTGAGCAAGGTGTTAAGATTTGGGACGGTAATGGATCTCGTGAATATTTAGATAAGATGGGGTTCAAAGATAGGAAAGTAGGAGATCTGGGGCCCGTTTACGGATTTCAATGGAGGCATTTTGGTGCTAAATACAAGACGTGCGATGACGACTATACTGGACAAGGTATTGATCAATTGAAACAGGTTATACATAAACTAAAGACAAATCCCTACGATAGAAGAATCATTATGAGTGCCTGGAACCCAGCTGATTTTGACAAAATGGCTTTGCCGCCATGCCATATTTTTTCACAGTTCTATGTCAGTTTCCCCAAAGAAGGAGAAGGATCCGGTAAGCCCCGCCTTTCATGCTTATTGTACCAACGTTCTTGTGATATGGGGTTGGGAGTACCATTTAACATTGCATCATATGCTTTGTTGACTAGAATGATTGCTAAAGTTGTCGACATGGAGCCAGGTGAGTTCATTCATACTTTGGGGGATGCACATGTTTATAAAGACCACATTGATGCCTTGAAAGAACAAATCACCAGAAATCCAAGACCATTCCCGAAACTAAAGATTAAAAGGGACGTTAAAGACATTGATGATTTCAAGTTGACAGACTTTGAAATTGAAGATTATAATCCTCATCCAAGAATTCAAATGAAAATGAGTGTATAA","protein_sequence":"MTMDGKNKEEEQYLDLCKRIIDEGEFRPDRTGTGTLSLFAPPQLRFSLRDDTFPLLTTKKVFTRGIILELLWFLAGDTDANLLSEQGVKIWDGNGSREYLDKMGFKDRKVGDLGPVYGFQWRHFGAKYKTCDDDYTGQGIDQLKQVIHKLKTNPYDRRIIMSAWNPADFDKMALPPCHIFSQFYVSFPKEGEGSGKPRLSCLLYQRSCDMGLGVPFNIASYALLTRMIAKVVDMEPGEFIHTLGDAHVYKDHIDALKEQITRNPRPFPKLKIKRDVKDIDDFKLTDFEIEDYNPHPRIQMKMSV"}]}