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name Structure Reference Source Properties Activities Metabolism

Pyridoxine

AlkaPlorer ID: AK009949

Synonym: None

IUPAC Name: 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol

Structure

SMILES: CC1=NC=C(CO)C(CO)=C1O

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InChI: InChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3

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InChIKey: LXNHXLLTXMVWPM-UHFFFAOYSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Escherichia coli Escherichia Enterobacteriaceae Enterobacterales Gammaproteobacteria Pseudomonadota None Bacteria

Properties Information

Molecule Weight: 169.18

TPSA？: 73.58000000000001

MolLogP？: 0.0802199999999998

Number of H-Donors: 3

Number of H-Acceptors: 4

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Cenchrus americanus Cenchrus americanus Activity 44.0 % 10.1016/j.cropro.2007.02.012
Cenchrus americanus Cenchrus americanus Activity 91.0 % 10.1016/j.cropro.2007.02.012
Cenchrus americanus Cenchrus americanus Activity nan None 10.1016/j.cropro.2007.02.012
Homo sapiens 15-hydroxyprostaglandin dehydrogenase [NAD+] Potency 14125.4 nM None
Homo sapiens Acetylcholinesterase AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 14321.7 nM None
Homo sapiens Alpha-1a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Androgen Receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Bile salt export pump IC50 1000000.0 nM 10.1124/dmd.111.040758
Homo sapiens Bile salt export pump IC50 1000000.0 nM 10.1124/dmd.112.047068
Homo sapiens Cyclooxygenase-1 AC50 3000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cyclooxygenase-1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cytochrome P450 1A2 AC50 nan None None
Homo sapiens Cytochrome P450 2C19 AC50 nan None None
Homo sapiens Cytochrome P450 2C9 AC50 nan None None
Homo sapiens Cytochrome P450 2D6 AC50 nan None None
Homo sapiens Cytochrome P450 3A4 AC50 nan None None
Homo sapiens Dopamine D1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 15848.9 nM None
Homo sapiens Estrogen receptor alpha AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens HERG AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histone deacetylase 6 Inhibition 2.11 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 3.49 % 10.6019/CHEMBL4808148
Homo sapiens Homo sapiens Activity 25.0 % 10.1128/aac.00247-07
Homo sapiens Homo sapiens Activity 45.8 % 10.1128/aac.00247-07
Homo sapiens Homo sapiens Activity nan None 10.1128/aac.00247-07
Homo sapiens Homo sapiens DILI_Concern nan None 10.1016/j.drudis.2016.02.015
Homo sapiens Homo sapiens DILI_severity_class 0.0 None 10.1016/j.drudis.2016.02.015
Homo sapiens Lysine-specific demethylase 4D-like Potency 12589.3 nM None
Homo sapiens Monoamine oxidase A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Mu opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Norepinephrine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 3A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 4A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Plasma fCmax 0.122 uM 10.1124/dmd.111.040758
Homo sapiens Progesterone receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Pyridoxal kinase Km 9900.0 nM 10.1021/np9005019
Homo sapiens Serotonin 1a (5-HT1a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2b (5-HT2b) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Thrombin AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Thromboxane A2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Vascular endothelial growth factor receptor 2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Bile salt export pump IC50 1000000.0 nM 10.1124/dmd.111.040758
Rattus norvegicus GABA receptor alpha-1 subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
None ADMET Cmax 30.0 nM 10.1021/acs.jmedchem.0c01177
None ADMET Cmax 60.0 nM 10.1021/acs.jmedchem.0c01177
None ADMET Drugexcretion 0.7 umol/hr 10.1021/acs.jmedchem.0c01177
None ADMET Drugexcretion 1.5 umol 10.1021/acs.jmedchem.0c01177
None ADMET TIME 3.0 hr 10.1021/acs.jmedchem.0c01177
None ADMET Tmax 1.0 hr 10.1021/acs.jmedchem.0c01177
None ADMET Tmax 3.0 hr 10.1021/acs.jmedchem.0c01177
None Hepatotoxicity DILI positive/negative 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx1000865
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx900326k
None Hepatotoxicity Hepatotoxicity nan None 10.1124/dmd.110.035113
None NON-PROTEIN TARGET Hepatotoxicity (acute) 0.0 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (animal toxicity known) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (benign tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (granulomatous hepatitis) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (mechanism) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 2.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 6.0 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (time to onset) nan None 10.1016/s0399-8320(04)95062-2
None No relevant target LogD7.4 -0.58 None 10.6019/CHEMBL3301361
None Unchecked Ac50 6.31 uM None
None Unchecked Ac50 8.913 uM None
None Unchecked AC50 6309.6 nM None
None Unchecked AC50 8912.5 nM None
None Unchecked Hepatotoxicity (acute) 1.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (association with vascular disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (choleostasis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (chronic liver disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cirrhosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (comment) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cytolytic) 1.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (malignant tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (severe hepatitis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (steatosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (successful reintroduction) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked Potency 28183.8 nM None
None Unchecked Reduction 0.0 % 10.1016/j.bmcl.2004.06.079
None Unchecked Reduction 4.0 % 10.1016/j.bmcl.2004.06.079

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT014608 C[SAH].Cc1ncc(CO)c(CO)c1O>>COCc1c(CO)cnc(C)c1O RXN-20798
AKRT015281 Cc1ncc(C=O)c(CO)c1O>>Cc1ncc(CO)c(CO)c1O R01910
AKRT015296 Cc1ncc(CO)c(C=O)c1O>>Cc1ncc(CO)c(CO)c1O PYRIDOXINE-4-DEHYDROGENASE-RXN
AKRT015303 Cc1ncc(CO)c(CO)c1O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O>>Cc1ncc(COP(=O)(O)O)c(CO)c1O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O None
AKRT015304 Cc1ncc(CO)c(CO)c1O.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1>>Cc1ncc(CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c(CO)c1O 2.4.1.160-RXN
AKRT015305 Cc1ncc(CO)c(CO)c1O.OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O>>Cc1ncc(CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c(CO)c1O MNXR131830
AKRT015306 Cc1ncc(CO)c(CO)c1O>>Cc1ncc(C=O)c(CO)c1O PYRIDOXINE-5-DEHYDROGENASE-RXN
AKRT015307 Cc1ncc(CO)c(CO)c1O>>Cc1ncc(CO)c(C=O)c1O PYRIDOXINE-4-OXIDASE-RXN
AKRT015308 Cc1ncc(CO)c(CO)c1O>>Cc1ncc(COP(=O)(O)O)c(CO)c1O PNKIN-RXN
AKRT015370 Cc1ncc(COP(=O)(O)O)c(CO)c1O>>Cc1ncc(CO)c(CO)c1O RXN-14181
AKRT015380 Cc1ncc(CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c(CO)c1O>>Cc1ncc(CO)c(CO)c1O enzymemap_63029