Pyridoxal

Details

• Internal ID: 69989f13-3188-4dcd-bb95-b59c22c13602
• Taxonomy: Organoheterocyclic compounds > Pyridines and derivatives > Pyridine carboxaldehydes > Pyridoxals and derivatives
• IUPAC Name: 3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde
• SMILES (Canonical): CC1=NC=C(C(=C1O)C=O)CO
• SMILES (Isomeric): CC1=NC=C(C(=C1O)C=O)CO
• InChI: InChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,4,10,12H,3H2,1H3
• InChI Key: RADKZDMFGJYCBB-UHFFFAOYSA-N
• Popularity: 5,685 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.16 g/mol
• Exact Mass: 167.058243149 g/mol
• Topological Polar Surface Area (TPSA): 70.40 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.40
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• Pyridoxaldehyde
• 66-72-8
• 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde
• 3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde
• Piridoxal
• 4-Pyridinecarboxaldehyde, 3-hydroxy-5-(hydroxymethyl)-2-methyl-
• EINECS 200-630-8
• NSC 19613
• BRN 0383768
• CHEBI:17310
• Oprea1_534980
• UNII-3THM379K8A
• 3-Hydroxy-5-hydroxymethyl-2-methyl-4-pyridincarbaldehyd
• 3THM379K8A
• DTXSID4046020
• 3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarboxaldehyde
• 3-Hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carboxaldehyde
• NCGC00142580-03
• 3-hydroxy-5-(hydroxymethyl)-2-methyl-pyridine-4-carbaldehyde
• 5-21-13-00044 (Beilstein Handbook Reference)
• 2-methyl-3-hydroxy-4-formyl-5-hydroxymethylpyridine
• DTXCID2026020
• CAS-66-72-8
• NSC19613
• Pyridocalx
• pyridoxal-
• nchembio.93-comp2
• PYRIDOXAL [MI]
• bmse000110
• PYRIDOXAL [WHO-DD]
• SCHEMBL29906
• MLS003876810
• CHEMBL102970
• EX-A576
• AIDS006783
• AIDS-006783
• Tox21_111561
• BBL004877
• BDBM50366979
• STL137770
• AKOS000634540
• Tox21_111561_1
• DB00147
• GS-3388
• NCGC00142580-01
• NCGC00142580-04
• NCGC00142580-05
• AS-83252
• SMR002533344
• LS-134382
• CS-0028583
• EN300-24934
• C00250
• D82489
• Q3065731
• 1,3-Dihydro-6-methylfuro[3,4-c]pyridine-1,7-diol
• 6-methyl-1,3-Dihydro-furo[3,4-c]pyridine-1,7-diol
• 849ADF16-456D-4BAB-A7EA-93A4C9D428AF
• Z56922082
• 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde #
• 4-Pyridinecarboxaldehyde, 3-hydroxy-5-(hydroxymethyl)-2-methyl- (9CI)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9813	98.13%
Caco-2	+	0.5853	58.53%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8952	89.52%
OATP2B1 inhibitior	-	0.8613	86.13%
OATP1B1 inhibitior	+	0.8100	81.00%
OATP1B3 inhibitior	+	0.9671	96.71%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9569	95.69%
P-glycoprotein inhibitior	-	0.9773	97.73%
P-glycoprotein substrate	-	0.9606	96.06%
CYP3A4 substrate	-	0.5863	58.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8685	86.85%
CYP3A4 inhibition	-	0.8435	84.35%
CYP2C9 inhibition	-	0.9194	91.94%
CYP2C19 inhibition	-	0.8778	87.78%
CYP2D6 inhibition	-	0.9437	94.37%
CYP1A2 inhibition	-	0.7841	78.41%
CYP2C8 inhibition	-	0.8859	88.59%
CYP inhibitory promiscuity	-	0.7875	78.75%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8200	82.00%
Carcinogenicity (trinary)	Non-required	0.7192	71.92%
Eye corrosion	-	0.9888	98.88%
Eye irritation	+	0.5906	59.06%
Skin irritation	-	0.7049	70.49%
Skin corrosion	-	0.9369	93.69%
Ames mutagenesis	+	0.5056	50.56%
Human Ether-a-go-go-Related Gene inhibition	-	0.6282	62.82%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	-	0.7769	77.69%
skin sensitisation	-	0.7672	76.72%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6816	68.16%
Acute Oral Toxicity (c)	III	0.5398	53.98%
Estrogen receptor binding	-	0.7332	73.32%
Androgen receptor binding	-	0.8225	82.25%
Thyroid receptor binding	-	0.7935	79.35%
Glucocorticoid receptor binding	-	0.8358	83.58%
Aromatase binding	-	0.6504	65.04%
PPAR gamma	-	0.6149	61.49%
Honey bee toxicity	-	0.9745	97.45%
Biodegradation	+	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	-	0.9199	91.99%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	14125.4 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	31622.8 nM	Potency	via CMAUP
CHEMBL3257	Q06278	Aldehyde oxidase	30000 nM	Ki	PMID: 7365745
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	31622.8 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	31622.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.90%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	93.49%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.76%	96.09%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	86.59%	93.10%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.21%	89.34%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.66%	96.00%
CHEMBL1937	Q92769	Histone deacetylase 2	82.86%	94.75%
CHEMBL2581	P07339	Cathepsin D	82.60%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.43%	94.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.00%	90.08%

Plants that contains it

• Allium sativum
• Arabidopsis thaliana

Cross-Links

• PubChem: 1050
• NPASS: NPC52831
• ChEMBL: CHEMBL102970
• LOTUS: LTS0187773
• wikiData: Q3065731