{"ymdb_id":"YMDB00602","created_at":"2011-05-29T18:34:55.000Z","updated_at":"2016-09-08T18:35:40.000Z","name":"Biotinyl-5'-AMP","cas":"4130-20-5","state":"Solid","melting_point":null,"description":"Biotinyl-5'-AMP is the active form of biotin in mammals. Biotin is a water soluble, heterocyclic cofactor for a small number of enzymes that facilitate the transfer of CO2 during carboxylation, decarboxylation, and transcarboxylation reactions involved in fatty acid and carbohydrate metabolism. Biotin biosynthesis is found in plants, bacteria, and certain fungi. [Biocyc PWY0-1507]","experimental_water_solubility":null,"experimental_logp_hydrophobicity":null,"location":"cytoplasm","synthesis_reference":"Christner, James E.; Coon, Minor J.  Synthesis of (+)-biotinyl 5'-adenylate.    Methods Enzymol.  (1970),  18(Pt. A),  386-90. ","chebi_id":"3110","hmdb_id":"HMDB04220","kegg_id":"C05921","pubchem_id":"440839","cs_id":null,"foodb_id":null,"wikipedia_link":null,"biocyc_id":null,"iupac":"({5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoyl}oxy)({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid","traditional_iupac":"β-amp","logp":"-4.116413751955203","pka":"12.413157781220377","alogps_solubility":"2.24e+00 g/l","alogps_logp":"-1.24","alogps_logs":"-2.41","acceptor_count":"11","donor_count":"6","rotatable_bond_count":"11","polar_surface_area":"233.26999999999998","refractivity":"130.62720000000002","polarizability":"53.47973601939037","formal_charge":"0","physiological_charge":"-1","pka_strongest_basic":"4.988470655480461","pka_strongest_acidic":"0.8302692044640101","bioavailability":"0","number_of_rings":"5","rule_of_five":"0","ghose_filter":"0","veber_rule":"0","mddr_like_rule":"1","synonyms":["(+)-Biotinyl 5'-adenylate","5'-Adenylic acid anhydride with biotin","5'-Adenylic acid monoanhydride with biotin","B-AMP","beta-AMP","bio-5-AMP","Biotin anhydride with 5'-adenylic acid","Biotinoyl 5'-adenylate","Biotinyl 5'-AMP","Biotinyl-5'-AMP"],"pathways":[{"name":"Biotin metabolism","kegg_map_id":"00780"}],"growth_conditions":[],"references":[{"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":9688262,"citation":"Hoja, U., Wellein, C., Greiner, E., Schweizer, E. (1998). \"Pleiotropic phenotype of acetyl-CoA-carboxylase-defective yeast cells--viability of a BPL1-amber mutation depending on its readthrough by normal tRNA(Gln)(CAG).\" Eur J Biochem 254:520-526."}],"proteins":[{"created_at":"2011-05-26T18:43:08.000Z","updated_at":"2011-07-22T17:54:19.000Z","name":"Biotin--protein ligase","uniprot_id":"P48445","uniprot_name":"BPL1_YEAST","enzyme":true,"transporter":false,"gene_name":"BPL1","num_residues":690,"molecular_weight":"76362.39844","theoretical_pi":"6.91","general_function":"Involved in biotin-[acetyl-CoA-carboxylase] ligase activity","specific_function":"Post-translational modification of specific protein by attachment of biotin. Acts on various carboxylases such as acetyl- CoA-carboxylase, pyruvate carboxylase, propionyl CoA carboxylase, and 3-methylcrotonyl CoA carboxylase","reactions":[{"id":1348,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2547,"direction":"\u003e","locations":"Cytoplasm","altext":"ATP + biotin + apo-[methylmalonyl-CoA:pyruvate carboxytransferase] = AMP + diphosphate + [methylmalonyl-CoA:pyruvate carboxytransferase].","export":false,"pw_reaction_id":null,"source":null},{"id":2548,"direction":"\u003e","locations":"Cytoplasm","altext":"ATP + biotin + apo-[propionyl-CoA:carbon-dioxide ligase (ADP-forming)] = AMP + diphosphate + [propionyl-CoA:carbon-dioxide ligase (ADP-forming)].","export":false,"pw_reaction_id":null,"source":null},{"id":2549,"direction":"\u003e","locations":"Cytoplasm","altext":"ATP + biotin + apo-[3-methylcrotonoyl-CoA:carbon-dioxide ligase (ADP-forming)] = AMP + diphosphate + [3-methylcrotonoyl-CoA:carbon-dioxide ligase (ADP-forming)].","export":false,"pw_reaction_id":null,"source":null},{"id":2550,"direction":"\u003e","locations":"Cytoplasm","altext":"ATP + biotin + apo-[acetyl-CoA:carbon-dioxide ligase (ADP-forming)] = AMP + diphosphate + [acetyl-CoA:carbon-dioxide ligase (ADP-forming)].","export":false,"pw_reaction_id":null,"source":null}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":"Cytoplasm","genbank_gene_id":"U27182","genbank_protein_id":"886081","gene_card_id":"BPL1","chromosome_location":"chromosome 4","locus":"YDL141W","synonyms":["Biotin apo-protein ligase","Biotin--[methylmalonyl-CoA-carboxytransferase] ligase","Biotin--[propionyl-CoA-carboxylase [ATP-hydrolyzing]] ligase","Holocarboxylase synthetase","HCS","Biotin--[methylcrotonoyl-CoA-carboxylase] ligase","Biotin--[acetyl-CoA-carboxylase] ligase"],"enzyme_classes":["6.3.4.-","6.3.4.9","6.3.4.10","6.3.4.11","6.3.4.15"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" ligase activity, forming carbon-nitrogen bonds"},{"category":"Function","description":" biotin-protein ligase activity"},{"category":"Function","description":" biotin-[acetyl-CoA-carboxylase] ligase activity"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" ligase activity"},{"category":"Process","description":" metabolic process"},{"category":"Process","description":" macromolecule metabolic process"},{"category":"Process","description":" macromolecule modification"},{"category":"Process","description":" protein modification process"}],"pfams":[{"name":"BPL_C","identifier":"PF02237"},{"name":"BPL_LipA_LipB","identifier":"PF03099"},{"name":"BPL_N","identifier":"PF09825"}],"pathways":[{"name":"Biotin metabolism","kegg_map_id":"00780"}],"gene_sequence":"ATGAATGTATTAGTCTATAATGGCCCAGGGACTACGCCAGGATCAGTTAAGCATGCTGTTGAAAGTTTACGTGACTTTTTGGAACCCTATTACGCCGTCAGTACTGTCAATGTTAAGGTATTACAGACAGAACCATGGATGTCAAAGACCTCCGCTGTAGTTTTTCCTGGTGGTGCCGATCTTCCTTACGTTCAAGCTTGTCAACCCATTATTTCTCGATTGAAACATTTTGTTAGCAAACAAGGTGGTGTCTTTATCGGATTTTGTGCAGGAGGTTACTTTGGCACCAGCCGTGTAGAATTTGCTCAAGGTGACCCTACAATGGAAGTATCAGGAAGCAGGGATTTGCGATTCTTTCCGGGAACAAGCAGAGGACCTGCGTACAATGGATTTCAGTATAACAGCGAGGCCGGTGCACGTGCAGTTAAATTGAATCTTCCAGATGGCTCACAGTTCTCAACTTATTTCAATGGAGGAGCCGTTTTTGTTGATGCAGATAAATTTGATAATGTCGAGATCTTGGCCACGTACGCAGAACACCCGGATGTGCCTTCTTCTGACTCAGGAAAAGGTCAAAGTGAAAACCCAGCTGCTGTAGTGCTATGTACGGTCGGAAGAGGAAAGGTTTTACTCACTGGACCACACCCTGAATTCAACGTCCGTTTTATGAGGAAATCCACAGATAAGCATTTTCTTGAAACCGTTGTGGAAAACCTGAAAGCACAGGAAATCATGAGGTTGAAATTTATGAGAACGGTTCTTACCAAAACTGGGTTGAATTGTAATAATGACTTCAATTATGTAAGAGCTCCAAATTTGACACCACTGTTTATGGCTAGTGCACCTAATAAGCGGAATTACTTGCAAGAAATGGAAAACAACTTAGCTCATCATGGAATGCATGCAAATAATGTTGAACTCTGCTCAGAATTAAACGCCGAAACTGACTCTTTCCAATTTTATAGAGGCTATAGAGCCTCTTACGATGCAGCAAGTTCGTCCTTGCTTCATAAAGAGCCAGATGAGGTTCCTAAGACCGTAATATTTCCTGGCGTAGATGAAGATATTCCACCATTTCAATATACGCCCAATTTTGACATGAAAGAATACTTCAAGTATCTGAATGTTCAAAACACCATAGGTTCTTTACTTCTATATGGTGAAGTTGTTACATCAACGAGTACCATATTGAATAATAATAAATCCTTATTAAGTTCGATCCCTGAAAGCACTTTACTTCACGTGGGTACTATTCAGGTTTCTGGGCGTGGGAGAGGTGGTAACACTTGGATTAATCCTAAAGGTGTTTGCGCATCAACGGCCGTCGTAACAATGCCGCTTCAATCGCCTGTGACTAATCGAAATATATCAGTTGTTTTTGTCCAGTATCTTTCTATGCTTGCTTACTGTAAGGCGATACTTTCGTACGCTCCTGGATTTTCAGATATTCCTGTTAGGATCAAATGGCCCAATGACCTTTATGCTTTGAGCCCCACCTACTATAAGCGTAAAAACTTGAAATTGGTTAACACCGGTTTTGAGCATACAAAGTTGCCCTTAGGTGATATCGAGCCCGCTTATCTTAAGATCTCTGGTTTATTAGTTAATACCCACTTCATAAACAATAAATATTGTTTGCTACTTGGCTGTGGTATAAATTTGACTAGTGATGGTCCTACAACTTCATTACAAACTTGGATTGATATCCTGAATGAAGAACGCCAACAATTACACCTTGATTTATTGCCAGCAATAAAGGCAGAAAAGCTGCAGGCACTCTATATGAATAACCTTGAGGTCATATTAAAACAGTTTATTAACTACGGAGCTGCGGAAATATTGCCAAGTTATTATGAGTTGTGGTTACATAGTAACCAAATAGTAACATTACCAGATCACGGAAATACGCAAGCCATGATTACTGGTATCACGGAAGACTACGGTTTACTGATTGCAAAAGAATTGGTAAGCGGTAGTTCCACTCAATTTACAGGAAACGTTTATAATTTACAGCCGGACGGTAACACTTTTGATATCTTCAAGAGCTTAATTGCTAAAAAGGTTCAGAGTTAA","protein_sequence":"MNVLVYNGPGTTPGSVKHAVESLRDFLEPYYAVSTVNVKVLQTEPWMSKTSAVVFPGGADLPYVQACQPIISRLKHFVSKQGGVFIGFCAGGYFGTSRVEFAQGDPTMEVSGSRDLRFFPGTSRGPAYNGFQYNSEAGARAVKLNLPDGSQFSTYFNGGAVFVDADKFDNVEILATYAEHPDVPSSDSGKGQSENPAAVVLCTVGRGKVLLTGPHPEFNVRFMRKSTDKHFLETVVENLKAQEIMRLKFMRTVLTKTGLNCNNDFNYVRAPNLTPLFMASAPNKRNYLQEMENNLAHHGMHANNVELCSELNAETDSFQFYRGYRASYDAASSSLLHKEPDEVPKTVIFPGVDEDIPPFQYTPNFDMKEYFKYLNVQNTIGSLLLYGEVVTSTSTILNNNKSLLSSIPESTLLHVGTIQVSGRGRGGNTWINPKGVCASTAVVTMPLQSPVTNRNISVVFVQYLSMLAYCKAILSYAPGFSDIPVRIKWPNDLYALSPTYYKRKNLKLVNTGFEHTKLPLGDIEPAYLKISGLLVNTHFINNKYCLLLGCGINLTSDGPTTSLQTWIDILNEERQQLHLDLLPAIKAEKLQALYMNNLEVILKQFINYGAAEILPSYYELWLHSNQIVTLPDHGNTQAMITGITEDYGLLIAKELVSGSSTQFTGNVYNLQPDGNTFDIFKSLIAKKVQS"}]}