2-Hydroxy-4-Methoxybenzaldehyde

Details

• Internal ID: 954ebd86-a8af-461f-a963-af294da45296
• Taxonomy: Benzenoids > Phenols > Methoxyphenols
• IUPAC Name: 2-hydroxy-4-methoxybenzaldehyde
• SMILES (Canonical): COC1=CC(=C(C=C1)C=O)O
• SMILES (Isomeric): COC1=CC(=C(C=C1)C=O)O
• InChI: InChI=1S/C8H8O3/c1-11-7-3-2-6(5-9)8(10)4-7/h2-5,10H,1H3
• InChI Key: WZUODJNEIXSNEU-UHFFFAOYSA-N
• Popularity: 294 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15 g/mol
• Exact Mass: 152.047344113 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.21
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 673-22-3
• 4-Methoxysalicylaldehyde
• Benzaldehyde, 2-hydroxy-4-methoxy-
• o-Hydroxy-p-methoxybenzaldehyde
• 4-Methoxysalicyaldehyde
• 2-Hydroxy-4-methoxy-benzaldehyde
• p-Anisaldehyde, 2-hydroxy-
• Salicylaldehyde, 4-methoxy-
• 2-Formyl-5-methoxyphenol
• 2-Hydroxy-p-anisaldehyde
• MFCD00003327
• EINECS 211-604-0
• NSC 155334
• BRN 1072443
• UNII-2N395P88LW
• AI3-38507
• CHEMBL350966
• 4-methoxy-2-hydroxybenzaldehyde
• 2N395P88LW
• NSC-155334
• 4-08-00-01754 (Beilstein Handbook Reference)
• 2-hydroxyanisaldehyde
• 4-o-Methylresorcylaldehyde
• 2-hydroxy4methoxybenzaldehyde
• ghl.PD_Mitscher_leg0.298
• 4-Methoxysalicylaldehyde,(S)
• SCHEMBL133876
• 2-hydroxy-4methoxybenzaldehyde
• 2-Hydroxy-4-methoxybenazldehyde
• 4-methoxy-6-hydroxybenzaldehyde
• DTXSID1060970
• FEMA NO. 4435
• 2-hydroxyl-4-methoxybenzaldehyde
• 4-METHOXY SALICYLAIDEHYDE
• 2-hydroxy-4-methoxy benzaldehyde
• 4-methoxy-2-hydroxy-benzaldehyde
• CHEBI:183274
• CS-D1182
• HY-N0445
• BDBM50139368
• CL8285
• NSC155334
• s5156
• STL195538
• AKOS000112553
• 2-Hydroxy-4-methoxybenzaldehyde, 98%
• CCG-266224
• PS-3237
• AC-24065
• BP-11480
• LS-20027
• PD088138
• SY012932
• AM20060850
• FT-0602352
• H0699
• EN300-24375
• A835710
• W-104720
• Q15634116
• Z188964138
• InChI=1/C8H8O3/c1-11-7-3-2-6(5-9)8(10)4-7/h2-5,10H,1H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9972	99.72%
Caco-2	+	0.7627	76.27%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.9426	94.26%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8296	82.96%
OATP1B3 inhibitior	+	0.9931	99.31%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9264	92.64%
P-glycoprotein inhibitior	-	0.9752	97.52%
P-glycoprotein substrate	-	0.9743	97.43%
CYP3A4 substrate	-	0.6291	62.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7924	79.24%
CYP3A4 inhibition	-	0.9529	95.29%
CYP2C9 inhibition	-	0.9784	97.84%
CYP2C19 inhibition	+	0.5220	52.20%
CYP2D6 inhibition	-	0.9644	96.44%
CYP1A2 inhibition	+	0.5499	54.99%
CYP2C8 inhibition	-	0.7343	73.43%
CYP inhibitory promiscuity	-	0.8231	82.31%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.6528	65.28%
Carcinogenicity (trinary)	Non-required	0.5906	59.06%
Eye corrosion	+	0.9532	95.32%
Eye irritation	+	1.0000	100.00%
Skin irritation	+	0.9128	91.28%
Skin corrosion	-	0.9307	93.07%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8544	85.44%
Micronuclear	+	0.5663	56.63%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.7694	76.94%
Respiratory toxicity	-	0.7889	78.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	-	0.9625	96.25%
Nephrotoxicity	+	0.5496	54.96%
Acute Oral Toxicity (c)	III	0.7818	78.18%
Estrogen receptor binding	-	0.8601	86.01%
Androgen receptor binding	-	0.6845	68.45%
Thyroid receptor binding	-	0.7246	72.46%
Glucocorticoid receptor binding	-	0.8535	85.35%
Aromatase binding	-	0.7812	78.12%
PPAR gamma	-	0.6924	69.24%
Honey bee toxicity	-	0.9492	94.92%
Biodegradation	+	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.7940	79.40%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	219.7 nM	IC50	via Super-PRED
CHEMBL1973	P14679	Tyrosinase	30000 nM	IC50	PMID: 14741268

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.87%	91.11%
CHEMBL4208	P20618	Proteasome component C5	95.37%	90.00%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	93.76%	98.11%
CHEMBL1951	P21397	Monoamine oxidase A	92.84%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.68%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.79%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.81%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.92%	99.17%
CHEMBL3194	P02766	Transthyretin	86.78%	90.71%
CHEMBL2581	P07339	Cathepsin D	86.63%	98.95%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.67%	97.36%
CHEMBL2535	P11166	Glucose transporter	82.54%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.01%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.56%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	81.33%	94.73%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.17%	90.24%

Plants that contains it

• Hemidesmus indicus
• Juglans nigra
• Mondia whitei
• Periploca sepium
• Sclerocarya birrea subsp. caffra

Cross-Links

• PubChem: 69600
• NPASS: NPC78662
• ChEMBL: CHEMBL350966
• LOTUS: LTS0030238
• wikiData: Q15634116