{"ymdb_id":"YMDB01072","created_at":"2011-07-21T17:07:15.000Z","updated_at":"2016-09-08T18:36:14.000Z","name":"2-phenylethanol","cas":"60-12-8","state":"Liquid","melting_point":"-27 oC","description":"Phenethyl alcohol (2-phenylethanol) is an alcohol with a pleasant floral odor that occurs widely in nature. It is found in a variety of essential oils, including rose, carnation, hyacinth, Aleppo pine, orange blossom, ylang-ylang, geranium, neroli, and champaca. It is therefore a common ingredient in flavors and perfumery, particularly when the smell of rose is desired. It is responsible for honey-like aromas, a major aroma component of Muscat wine. It is used as an additive in cigarettes. It is also used as a preservative in soaps due to its stability in basic conditions. In biology it is of interest due to its antimicrobial properties.","experimental_water_solubility":"22.2 mg/mL at 25 oC [VALVANI, SC et al. (1981)]","experimental_logp_hydrophobicity":"1.36 [HANSCH,C ET AL. (1995)]","location":"extracellular;mitochondrion;cytoplasm","synthesis_reference":null,"chebi_id":"49000","hmdb_id":null,"kegg_id":"C05853","pubchem_id":"6054","cs_id":"5830","foodb_id":null,"wikipedia_link":"Phenethyl_alcohol","biocyc_id":null,"iupac":"2-phenylethan-1-ol","traditional_iupac":"phenylethanol","logp":"1.4945572536666667","pka":null,"alogps_solubility":"1.13e+01 g/l","alogps_logp":"1.51","alogps_logs":"-1.03","acceptor_count":"1","donor_count":"1","rotatable_bond_count":"2","polar_surface_area":"20.23","refractivity":"37.6289","polarizability":"13.867704086240545","formal_charge":"0","physiological_charge":"0","pka_strongest_basic":"-2.4130330705294574","pka_strongest_acidic":"15.88195457126324","bioavailability":"1","number_of_rings":"1","rule_of_five":"1","ghose_filter":"0","veber_rule":"1","mddr_like_rule":"0","synonyms":["1-Phenyl-2-ethanol","1-phenyl-2-ethanol (beta-phenylethanol)","2-Hydroxyethylbenzene","2-PEA","2-Phenethanol","2-Phenethyl Alcohol","2-PhenyIethanol","2-PHENYL-ETHANOL","2-Phenylethanol","2-Phenylethyl alcohol","Benzeneethanol","Benzeneethanol (2-Phenylethanol)","benzenethanol","Benzyl Carbinol","Benzylmethanol","beta-Fenethylalkohol","beta-Fenylethanol","beta-Hydroxyethylbenzene","beta-P.E.A.","beta-PEA","beta-Phenethanol","beta-Phenethyl alcohol","beta-Phenylethanol","beta-Phenylethyl alcohol","Ethanol, 2-phenyl-","Hydroxyethylbenzene","Mellol","Methanol, benzyl-","Orange oil","PEA","Phenethanol","Phenethyl alcohol","Phenylethanol","Phenylethyl alcohol","Phenylethyl, b- alcohol","Rose oil"],"pathways":[{"name":"Phenylalanine metabolism","kegg_map_id":"00360"}],"growth_conditions":[],"references":[{"pubmed_id":12957907,"citation":"Verstrepen, K. J., Van Laere, S. D., Vanderhaegen, B. M., Derdelinckx, G., Dufour, J. P., Pretorius, I. S., Winderickx, J., Thevelein, J. M., Delvaux, F. R. (2003). \"Expression levels of the yeast alcohol acetyltransferase genes ATF1, Lg-ATF1, and ATF2 control the formation of a broad range of volatile esters.\" Appl Environ Microbiol 69:5228-5237."},{"pubmed_id":10552428,"citation":"Antonelli, A., Castellari, L., Zambonelli, C., Carnacini, A. (1999). \"Yeast influence on volatile composition of wines.\" J Agric Food Chem 47:1139-1144."},{"pubmed_id":20151225,"citation":"Tsakiris, A., Koutinas, A. A., Psarianos, C., Kourkoutas, Y., Bekatorou, A. (2010). \"A new process for wine production by penetration of yeast in uncrushed frozen grapes.\" Appl Biochem Biotechnol 162:1109-1121."},{"pubmed_id":12236692,"citation":"Patel, S., Shibamoto, T. (2002). \"Effect of different strains of Saccharomyces cerevisiae on production of volatiles in Napa Gamay wine and Petite Sirah wine.\" J Agric Food Chem 50:5649-5653."},{"pubmed_id":12702265,"citation":"Leskovac, V., Trivic, S., Pericin, D. (2002). \"The three zinc-containing alcohol dehydrogenases from baker's yeast, Saccharomyces cerevisiae.\" FEMS Yeast Res 2:481-494."},{"pubmed_id":17287358,"citation":"Chi, A., Huttenhower, C., Geer, L. Y., Coon, J. J., Syka, J. E., Bai, D. L., Shabanowitz, J., Burke, D. J., Troyanskaya, O. G., Hunt, D. F. (2007). \"Analysis of phosphorylation sites on proteins from Saccharomyces cerevisiae by electron transfer dissociation (ETD) mass spectrometry.\" Proc Natl Acad Sci U S A 104:2193-2198."},{"pubmed_id":12423374,"citation":"Larroy, C., Pares, X., Biosca, J. A. (2002). \"Characterization of a Saccharomyces cerevisiae NADP(H)-dependent alcohol dehydrogenase (ADHVII), a member of the cinnamyl alcohol dehydrogenase family.\" Eur J Biochem 269:5738-5745."},{"pubmed_id":12499363,"citation":"Dickinson, J. R., Salgado, L. E., Hewlins, M. J. (2003). \"The catabolism of amino acids to long chain and complex alcohols in Saccharomyces cerevisiae.\" J Biol Chem 278:8028-8034."},{"pubmed_id":11742541,"citation":"Larroy, C., Fernandez, M. R., Gonzalez, E., Pares, X., Biosca, J. A. (2002). \"Characterization of the Saccharomyces cerevisiae YMR318C (ADH6) gene product as a broad specificity NADPH-dependent alcohol dehydrogenase: relevance in aldehyde reduction.\" Biochem J 361:163-172."}],"proteins":[{"created_at":"2011-05-27T02:08:01.000Z","updated_at":"2011-07-22T17:54:08.000Z","name":"NADP-dependent alcohol dehydrogenase 7","uniprot_id":"P25377","uniprot_name":"ADH7_YEAST","enzyme":true,"transporter":false,"gene_name":"ADH7","num_residues":361,"molecular_weight":"39348.19922","theoretical_pi":"7.35","general_function":"Involved in zinc ion binding","specific_function":"NADP-dependent alcohol dehydrogenase with a broad substrate 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reduction"},{"category":"Process","description":" metabolic process"}],"pfams":[{"name":"ADH_N","identifier":"PF08240"},{"name":"ADH_zinc_N","identifier":"PF00107"}],"pathways":[{"name":"Glycolysis / Gluconeogenesis","kegg_map_id":"00010"},{"name":"Glycerolipid metabolism","kegg_map_id":"00561"},{"name":"Ethanol fermentation","kegg_map_id":null},{"name":"Glycerol metabolism","kegg_map_id":null},{"name":"Isoleucine degradation","kegg_map_id":null},{"name":"Leucine Degradation","kegg_map_id":null},{"name":"Phenylalanine metabolism","kegg_map_id":"00360"},{"name":"Pyruvate metabolism","kegg_map_id":"00620"},{"name":"Tryptophan metabolism","kegg_map_id":"00380"},{"name":"Tyrosine metabolism","kegg_map_id":"00350"},{"name":"Valine Degradation","kegg_map_id":null}],"gene_sequence":"ATGCTTTACCCAGAAAAATTTCAGGGCATCGGTATTTCCAACGCAAAGGATTGGAAGCATCCTAAATTAGTGAGTTTTGACCCAAAACCCTTTGGCGATCATGACGTTGATGTTGAAATTGAAGCCTGTGGTATCTGCGGATCTGATTTTCATATAGCCGTTGGTAATTGGGGTCCAGTCCCAGAAAATCAAATCCTTGGACATGAAATAATTGGCCGCGTGGTGAAGGTTGGATCCAAGTGCCACACTGGGGTAAAAATCGGTGACCGTGTTGGTGTTGGTGCCCAAGCCTTGGCGTGTTTTGAGTGTGAACGTTGCAAAAGTGACAACGAGCAATACTGTACCAATGACCACGTTTTGACTATGTGGACTCCTTACAAGGACGGCTACATTTCACAAGGAGGCTTTGCCTCCCACGTGAGGCTTCATGAACACTTTGCTATTCAAATACCAGAAAATATTCCAAGTCCGCTAGCCGCTCCATTATTGTGTGGTGGTATTACAGTTTTCTCTCCACTACTAAGAAATGGCTGTGGTCCAGGTAAGAGGGTAGGTATTGTTGGCATCGGTGGTATTGGGCATATGGGGATTCTGTTGGCTAAAGCTATGGGAGCCGAGGTTTATGCGTTTTCGCGAGGCCACTCCAAGCGGGAGGATTCTATGAAACTCGGTGCTGATCACTATATTGCTATGTTGGAGGATAAAGGCTGGACAGAACAATACTCTAACGCTTTGGACCTTCTTGTCGTTTGCTCATCATCTTTGTCGAAAGTTAATTTTGACAGTATCGTTAAGATTATGAAGATTGGAGGCTCCATCGTTTCAATTGCTGCTCCTGAAGTTAATGAAAAGCTTGTTTTAAAACCGTTGGGCCTAATGGGAGTATCAATCTCAAGCAGTGCTATCGGATCTAGGAAGGAAATCGAACAACTATTGAAATTAGTTTCCGAAAAGAATGTCAAAATATGGGTGGAAAAACTTCCGATCAGCGAAGAAGGCGTCAGCCATGCCTTTACAAGGATGGAAAGCGGAGACGTCAAATACAGATTTACTTTGGTCGATTATGATAAGAAATTCCATAAATAG","protein_sequence":"MLYPEKFQGIGISNAKDWKHPKLVSFDPKPFGDHDVDVEIEACGICGSDFHIAVGNWGPVPENQILGHEIIGRVVKVGSKCHTGVKIGDRVGVGAQALACFECERCKSDNEQYCTNDHVLTMWTPYKDGYISQGGFASHVRLHEHFAIQIPENIPSPLAAPLLCGGITVFSPLLRNGCGPGKRVGIVGIGGIGHMGILLAKAMGAEVYAFSRGHSKREDSMKLGADHYIAMLEDKGWTEQYSNALDLLVVCSSSLSKVNFDSIVKIMKIGGSIVSIAAPEVNEKLVLKPLGLMGVSISSSAIGSRKEIEQLLKLVSEKNVKIWVEKLPISEEGVSHAFTRMESGDVKYRFTLVDYDKKFHK"},{"created_at":"2011-05-27T02:09:59.000Z","updated_at":"2011-07-22T17:54:08.000Z","name":"NADP-dependent alcohol dehydrogenase 6","uniprot_id":"Q04894","uniprot_name":"ADH6_YEAST","enzyme":true,"transporter":false,"gene_name":"ADH6","num_residues":360,"molecular_weight":"39617.30078","theoretical_pi":"6.73","general_function":"Involved in zinc ion binding","specific_function":"NADP-dependent alcohol dehydrogenase with a broad substrate specificity","reactions":[{"id":1295,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1297,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1304,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1306,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2660,"direction":"\u003e","locations":"","altext":"An alcohol + NADP(+) = an aldehyde + NADPH.","export":false,"pw_reaction_id":null,"source":null},{"id":3860,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006381","source":"Smpdb"},{"id":3900,"direction":"\u003c\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006417","source":"Smpdb"},{"id":3901,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006521","source":"Smpdb"},{"id":3902,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006526","source":"Smpdb"},{"id":3903,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006538","source":"Smpdb"},{"id":3904,"direction":"\u003c\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006558","source":"Smpdb"},{"id":3905,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006972","source":"Smpdb"},{"id":3906,"direction":"\u003c\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006976","source":"Smpdb"},{"id":3907,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006980","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":"1Q1N","cellular_location":null,"genbank_gene_id":"Z54141","genbank_protein_id":"984691","gene_card_id":"ADH6","chromosome_location":"chromosome 13","locus":"YMR318C","synonyms":["NADP-dependent alcohol dehydrogenase VI","ScADHVI"],"enzyme_classes":["1.1.1.2"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" zinc ion binding"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" binding"},{"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":" oxidoreductase activity"},{"category":"Process","description":" oxidation reduction"},{"category":"Process","description":" metabolic process"}],"pfams":[{"name":"ADH_N","identifier":"PF08240"},{"name":"ADH_zinc_N","identifier":"PF00107"}],"pathways":[{"name":"Glycolysis / Gluconeogenesis","kegg_map_id":"00010"},{"name":"Glycerolipid metabolism","kegg_map_id":"00561"},{"name":"Ethanol fermentation","kegg_map_id":null},{"name":"Glycerol metabolism","kegg_map_id":null},{"name":"Isoleucine degradation","kegg_map_id":null},{"name":"Leucine Degradation","kegg_map_id":null},{"name":"Phenylalanine metabolism","kegg_map_id":"00360"},{"name":"Pyruvate metabolism","kegg_map_id":"00620"},{"name":"Tryptophan metabolism","kegg_map_id":"00380"},{"name":"Tyrosine metabolism","kegg_map_id":"00350"},{"name":"Valine Degradation","kegg_map_id":null}],"gene_sequence":"ATGTCTTATCCTGAGAAATTTGAAGGTATCGCTATTCAATCACACGAAGATTGGAAAAACCCAAAGAAGACAAAGTATGACCCAAAACCATTTTACGATCATGACATTGACATTAAGATCGAAGCATGTGGTGTCTGCGGTAGTGATATTCATTGTGCAGCTGGTCATTGGGGCAATATGAAGATGCCGCTAGTCGTTGGTCATGAAATCGTTGGTAAAGTTGTCAAGCTAGGGCCCAAGTCAAACAGTGGGTTGAAAGTCGGTCAACGTGTTGGTGTAGGTGCTCAAGTCTTTTCATGCTTGGAATGTGACCGTTGTAAGAATGATAATGAACCATACTGCACCAAGTTTGTTACCACATACAGTCAGCCTTATGAAGACGGCTATGTGTCGCAGGGTGGCTATGCAAACTACGTCAGAGTTCATGAACATTTTGTGGTGCCTATCCCAGAGAATATTCCATCACATTTGGCTGCTCCACTATTATGTGGTGGTTTGACTGTGTACTCTCCATTGGTTCGTAACGGTTGCGGTCCAGGTAAAAAAGTTGGTATAGTTGGTCTTGGTGGTATCGGCAGTATGGGTACATTGATTTCCAAAGCCATGGGGGCAGAGACGTATGTTATTTCTCGTTCTTCGAGAAAAAGAGAAGATGCAATGAAGATGGGCGCCGATCACTACATTGCTACATTAGAAGAAGGTGATTGGGGTGAAAAGTACTTTGACACCTTCGACCTGATTGTAGTCTGTGCTTCCTCCCTTACCGACATTGACTTCAACATTATGCCAAAGGCTATGAAGGTTGGTGGTAGAATTGTCTCAATCTCTATACCAGAACAACACGAAATGTTATCGCTAAAGCCATATGGCTTAAAGGCTGTCTCCATTTCTTACAGTGCTTTAGGTTCCATCAAAGAATTGAACCAACTCTTGAAATTAGTCTCTGAAAAAGATATCAAAATTTGGGTGGAAACATTACCTGTTGGTGAAGCCGGCGTCCATGAAGCCTTCGAAAGGATGGAAAAGGGTGACGTTAGATATAGATTTACCTTAGTCGGCTACGACAAAGAATTTTCAGACTAG","protein_sequence":"MSYPEKFEGIAIQSHEDWKNPKKTKYDPKPFYDHDIDIKIEACGVCGSDIHCAAGHWGNMKMPLVVGHEIVGKVVKLGPKSNSGLKVGQRVGVGAQVFSCLECDRCKNDNEPYCTKFVTTYSQPYEDGYVSQGGYANYVRVHEHFVVPIPENIPSHLAAPLLCGGLTVYSPLVRNGCGPGKKVGIVGLGGIGSMGTLISKAMGAETYVISRSSRKREDAMKMGADHYIATLEEGDWGEKYFDTFDLIVVCASSLTDIDFNIMPKAMKVGGRIVSISIPEQHEMLSLKPYGLKAVSISYSALGSIKELNQLLKLVSEKDIKIWVETLPVGEAGVHEAFERMEKGDVRYRFTLVGYDKEFSD"}]}