1.0 2016-09-30 22:46:42 UTC 2020-06-04 20:33:28 UTC BMDB0001491 BMDB01491 Pyridoxal 5'-phosphate Pyridoxal 5'-phosphate, also known as phosphopyridoxal or PLP, belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives are compounds containing a pyridoxal moiety, which consists of a pyridine ring substituted at positions 2,3,4, and 5 by a methyl group, a hydroxyl group, a carbaldehyde group, and a hydroxymethyl group, respectively. Pyridoxal 5'-phosphate is a drug which is used for nutritional supplementation and for treating dietary shortage or imbalance. Pyridoxal 5'-phosphate exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Pyridoxal 5'-phosphate exists in all living species, ranging from bacteria to humans. In cattle, pyridoxal 5'-phosphate is involved in the metabolic pathway called the glycine and serine metabolism pathway. Pyridoxal 5'-phosphate is a potentially toxic compound. Pyridoxal 5'-phosphate has been found to be associated with several diseases known as rheumatoid arthritis, epilepsy, early-onset, vitamin b6-dependent, odontohypophosphatasia, and pyridoxamine 5-prime-phosphate oxidase deficiency; also pyridoxal 5'-phosphate has been linked to the inborn metabolic disorders including celiac disease. 3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphate Codecarboxylase Phosphoric acid mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester PLP Pyridoxal 5'-(dihydrogen phosphate) Pyridoxal 5-monophosphoric acid ester Pyridoxal 5-phosphate Pyridoxal phosphate PYRIDOXAL-5'-phosphATE 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphoric acid Phosphate mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester Pyridoxal 5'-(dihydrogen phosphoric acid) Pyridoxal 5-monophosphate ester Pyridoxal 5-phosphoric acid Pyridoxal phosphoric acid PYRIDOXAL-5'-phosphoric acid Pyridoxal 5'-phosphoric acid Apolon b6 Biosechs Coenzyme b6 Hairoxal Hexermin-p Hi-pyridoxin Hiadelon Himitan PAL-p Phosphopyridoxal Phosphopyridoxal coenzyme Pidopidon Piodel Pydoxal Pyridoxal p Pyridoxal-p Pyridoxyl phosphate Pyromijin Sechvitan Vitahexin-p Vitazechs Phosphate, pyridoxal Pyridoxal 5 phosphate C8H10NO6P 247.1419 247.024573569 [(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid pyridoxal phosphate 54-47-7 CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14) NGVDGCNFYWLIFO-UHFFFAOYSA-N belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives are compounds containing a pyridoxal moiety, which consists of a pyridine ring substituted at positions 2,3,4, and 5 by a methyl group, a hydroxyl group, a carbaldehyde group, and a hydroxymethyl group, respectively. Organic compounds Organoheterocyclic compounds Pyridines and derivatives Pyridine carboxaldehydes Pyridoxals and derivatives Aryl-aldehydes Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Hydroxypyridines Methylpyridines Monoalkyl phosphates Organic oxides Organonitrogen compounds Organopnictogen compounds Vinylogous acids Aldehyde Alkyl phosphate Aromatic heteromonocyclic compound Aryl-aldehyde Azacycle Heteroaromatic compound Hydrocarbon derivative Hydroxypyridine Methylpyridine Monoalkyl phosphate Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organonitrogen compound Organooxygen compound Organopnictogen compound Phosphoric acid ester Pyridoxal Vinylogous acid Aromatic heteromonocyclic compounds methylpyridines monohydroxypyridine pyridinecarbaldehyde vitamin B6 phosphate Solid melting_point 255 °C water_solubility 28 mg/mL logp -0.55 ALOGPS logs -1.64 ALOGPS logp -2.1 ChemAxon pka_strongest_acidic 1.68 ChemAxon pka_strongest_basic 4.11 ChemAxon iupac [(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid ChemAxon average_mass 247.1419 ChemAxon mono_mass 247.024573569 ChemAxon smiles CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O ChemAxon formula C8H10NO6P ChemAxon inchi InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14) ChemAxon inchikey NGVDGCNFYWLIFO-UHFFFAOYSA-N ChemAxon polar_surface_area 116.95 ChemAxon refractivity 54.75 ChemAxon polarizability 20.9 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Alanine Metabolism SMP0087164 Ammonia Recycling SMP0087177 Arginine and Proline Metabolism SMP0087178 Aspartate Metabolism SMP0087165 beta-Alanine Metabolism SMP0087180 Carnitine Synthesis SMP0087187 Cysteine Metabolism SMP0087189 Folate Metabolism SMP0087196 Glucose-Alanine Cycle SMP0087221 Glutamate Metabolism SMP0087169 Glycine and Serine Metabolism SMP0087245 Histidine Metabolism SMP0087219 Homocysteine Degradation SMP0087201 Lysine Degradation SMP0087203 Malate-Aspartate Shuttle SMP0087204 Methionine Metabolism SMP0087249 Phenylalanine and Tyrosine Metabolism SMP0087218 Porphyrin Metabolism SMP0087243 Propanoate Metabolism SMP0087248 Selenoamino Acid Metabolism SMP0087161 Spermidine and Spermine Biosynthesis SMP0087213 Sphingolipid Metabolism SMP0087244 Starch and Sucrose Metabolism SMP0087252 Taurine and Hypotaurine Metabolism SMP0087214 Threonine and 2-Oxobutanoate Degradation SMP0087262 Tryptophan Metabolism SMP0087237 Tyrosine Metabolism SMP0087235 Urea Cycle SMP0087224 Valine, Leucine, and Isoleucine Degradation SMP0087234 Vitamin B6 Metabolism SMP0087240 Specdb::NmrTwoD 1076 Specdb::NmrTwoD 1657 Specdb::CMs 1939 Specdb::CMs 2377 Specdb::CMs 31340 Specdb::CMs 32161 Specdb::CMs 32162 Specdb::CMs 38094 Specdb::CMs 156931 Specdb::NmrOneD 1718 Specdb::NmrOneD 4860 Specdb::NmrOneD 4861 Specdb::NmrOneD 147900 Specdb::NmrOneD 147901 Specdb::NmrOneD 147902 Specdb::NmrOneD 147903 Specdb::NmrOneD 147904 Specdb::NmrOneD 147905 Specdb::NmrOneD 147906 Specdb::NmrOneD 147907 Specdb::NmrOneD 147908 Specdb::NmrOneD 147909 Specdb::NmrOneD 147910 Specdb::NmrOneD 147911 Specdb::NmrOneD 147912 Specdb::NmrOneD 147913 Specdb::NmrOneD 147914 Specdb::NmrOneD 147915 Specdb::NmrOneD 147916 Specdb::NmrOneD 147917 Specdb::NmrOneD 147918 Specdb::NmrOneD 147919 Specdb::MsMs 1610 Specdb::MsMs 1611 Specdb::MsMs 1612 Specdb::MsMs 5354 Specdb::MsMs 5355 Specdb::MsMs 5356 Specdb::MsMs 5357 Specdb::MsMs 5358 Specdb::MsMs 5359 Specdb::MsMs 5360 Specdb::MsMs 5361 Specdb::MsMs 5362 Specdb::MsMs 20057 Specdb::MsMs 20058 Specdb::MsMs 20059 Specdb::MsMs 21608 Specdb::MsMs 21609 Specdb::MsMs 21610 Specdb::MsMs 438274 Specdb::MsMs 438275 Specdb::MsMs 438276 Specdb::MsMs 438277 Specdb::MsMs 438278 Specdb::MsMs 439165 Specdb::MsMs 439170 Erythrocyte Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Kidney Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk 0.557 +/- 0.522 uM Raw milk from Holstein cows Coburn SP, Mahuren JD, Pauly TA, Ericson KL, Townsend DW: Alkaline phosphatase activity and pyridoxal phosphate concentrations in the milk of various species. J Nutr. 1992 Dec;122(12):2348-53. doi: 10.1093/jn/122.12.2348. 1453218 Neuron Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Skeletal Muscle Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 C00018 DB00114 FDB021820 1022 1051 18405 C00007503 Pyridoxal_phosphate PYRIDOXAL_PHOSPHATE 33526 6275 Coburn SP, Mahuren JD, Pauly TA, Ericson KL, Townsend DW: Alkaline phosphatase activity and pyridoxal phosphate concentrations in the milk of various species. J Nutr. 1992 Dec;122(12):2348-53. doi: 10.1093/jn/122.12.2348. 1453218 BMDBP00082 Serine racemase A0JNI4 SRR Enzyme BMDBP00083 Serine hydroxymethyltransferase, mitochondrial Q3SZ20 SHMT2 Enzyme BMDBP00085 Serine palmitoyltransferase 1 Q3MHG1 SPTLC1 Enzyme BMDBP00087 Serine hydroxymethyltransferase, cytosolic Q5E9P9 SHMT1 Enzyme BMDBP00088 L-serine dehydratase/L-threonine deaminase Q0VCW4 SDS Enzyme BMDBP00161 Alpha-1,4 glucan phosphorylase B0JYK6 PYGM Enzyme BMDBP00214 Pyridoxine-5'-phosphate oxidase Q5E9K3 PNPO Enzyme BMDBP00215 Cysteine conjugate-beta lyase; cytoplasmic (Glutamine transaminase K, kyneurenine aminotransferase) A0JN49 CCBL1 Enzyme BMDBP00216 Pyridoxal phosphate phosphatase Q3ZBF9 PDXP Enzyme BMDBP00217 Similar to aspartate aminotransferase Q862R2 Enzyme BMDBP00218 Similar to aspartate aminotransferase Q862Q8 Enzyme BMDBP00219 Cytoplasmic cysteine conjugate-beta lyase A5D991 CCBL1 Enzyme BMDBP00220 Glutamate decarboxylase B6A7R2 GAD2 Enzyme BMDBP00221 Mitochondrial amidoxime reducing component 2 Q1LZH1 MTARC2 Enzyme BMDBP00222 4-aminobutyrate aminotransferase A2VDK2 ABAT Enzyme BMDBP00223 Pyridoxal phosphate phosphatase PHOSPHO2 Q2KI06 PHOSPHO2 Enzyme BMDBP00224 Glutamic-pyruvate transaminase Q7YRA0 GPT Enzyme BMDBP00225 1-aminocyclopropane-1-carboxylate synthase Q0V8M2 ACS Enzyme BMDBP00226 Branched-chain-amino-acid aminotransferase A4IFQ7 BCAT1 Enzyme BMDBP00227 Branched-chain-amino-acid aminotransferase, mitochondrial Q5EA40 BCAT2 Enzyme BMDBP00228 Branched-chain-amino-acid aminotransferase Q0V8J6 BCAT2 Enzyme BMDBP00229 Branched-chain-amino-acid aminotransferase Q5E9U7 BCAT2 Enzyme BMDBP00239 Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q5E9N4 AADAT Enzyme BMDBP00366 2-amino-3-ketobutyrate coenzyme A ligase, mitochondrial Q0P5L8 GCAT Enzyme BMDBP00539 Selenocysteine lyase A2VDS1 SCLY Enzyme BMDBP00561 Histidine decarboxylase Q5EA83 HDC Enzyme BMDBP00567 Aspartate aminotransferase, cytoplasmic P33097 GOT1 Enzyme BMDBP00569 Aspartate aminotransferase, mitochondrial P12344 GOT2 Enzyme BMDBP00571 Putative aspartate aminotransferase, cytoplasmic 2 Q2T9S8 GOT1L1 Enzyme BMDBP00596 4-aminobutyrate aminotransferase, mitochondrial Q9BGI0 ABAT Enzyme BMDBP00624 5-aminolevulinate synthase, nonspecific, mitochondrial A6QLI6 ALAS1 Enzyme BMDBP00629 5-aminolevulinate synthase, erythroid-specific, mitochondrial Q3ZC31 ALAS2 Enzyme BMDBP00793 Alanine--glyoxylate aminotransferase 2, mitochondrial Q17QF0 AGXT2 Enzyme BMDBP00818 Cystathionine gamma-lyase Q58DW2 CTH Enzyme BMDBP00855 Phosphoserine aminotransferase A6QR28 PSAT1 Enzyme BMDBP00858 Alanine aminotransferase 1 A4IFH5 GPT Enzyme BMDBP00859 Tyrosine aminotransferase Q58CZ9 TAT Enzyme BMDBP00861 Kynurenine--oxoglutarate transaminase 3 Q0P5G4 KYAT3 Enzyme BMDBP00862 Glutamate decarboxylase 1 Q0VCA1 GAD1 Enzyme BMDBP00922 Ornithine decarboxylase P27117 ODC1 Enzyme BMDBP00923 Arginine decarboxylase Q2TBX3 ADC Enzyme BMDBP00936 Aromatic-L-amino-acid decarboxylase P27718 DDC Enzyme BMDBP01172 Glycogen phosphorylase, brain form Q3B7M9 PYGB Enzyme BMDBP01208 Glycogen phosphorylase, liver form Q0VCM4 PYGL Enzyme BMDBP01247 Glycogen phosphorylase, muscle form P79334 PYGM Enzyme BMDBP01327 Ornithine aminotransferase, mitochondrial Q3ZCF5 OAT Enzyme BMDBP01361 Tyrosine aminotransferase A6H7B2 TAT Enzyme BMDBP01362 SPTLC2 protein A5PKM3 SPTLC2 Enzyme BMDBP01363 Molybdenum cofactor sulfurase Q9N0E7 MOCOS Enzyme BMDBP01364 Pyridoxal-dependent decarboxylase domain-containing protein 1 A7MBC2 PDXDC1 Enzyme BMDBP01365 Cystathionine beta-synthase A7MBF8 CBS Enzyme BMDBP01366 Ethanolamine-phosphate phospho-lyase Q5E9S4 ETNPPL Enzyme BMDBP01367 Serine--pyruvate aminotransferase A7MBF1 AGXT Enzyme BMDBP01368 NFS1 protein A5PKG4 NFS1 Enzyme BMDBP01369 1-aminocyclopropane-1-carboxylate synthase-like protein 1 Q5E9H2 ACCS Enzyme BMDBP01370 Serum albumin P02769 ALB Enzyme BMDBP01371 SDSL protein A5PKH5 SDSL Enzyme BMDBP01372 Pyridoxal phosphate homeostasis protein Q3T0G5 PLPBP Enzyme BMDBP01373 CTH protein B0JYP8 CTH Enzyme BMDBP01374 Aromatic-L-amino-acid decarboxylase A5PJV5 DDC Enzyme BMDBP01375 SGPL1 protein A5D788 SGPL1 Enzyme BMDBP01376 Acidic amino acid decarboxylase GADL1 A6QM00 GADL1 Enzyme