3,4-Dimethoxybenzoic acid

Details

• Internal ID: e3e70700-aad0-49a5-9726-b0040ee70aa4
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Methoxybenzoic acids and derivatives > P-methoxybenzoic acids and derivatives
• IUPAC Name: 3,4-dimethoxybenzoic acid
• SMILES (Canonical): COC1=C(C=C(C=C1)C(=O)O)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)C(=O)O)OC
• InChI: InChI=1S/C9H10O4/c1-12-7-4-3-6(9(10)11)5-8(7)13-2/h3-5H,1-2H3,(H,10,11)
• InChI Key: DAUAQNGYDSHRET-UHFFFAOYSA-N
• Popularity: 489 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 182.17 g/mol
• Exact Mass: 182.05790880 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.40
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• VERATRIC ACID
• 93-07-2
• Benzoic acid, 3,4-dimethoxy-
• Dimethylprotocatechuic acid
• Veratrumenoic acid
• Veratrylic acid
• 3,4-Dimethylprotocatechuic acid
• 3,4-Dimethoxy-benzoic acid
• MFCD00002500
• 3,4-Dimethoxybenzoic acid (Veratric acid)
• NSC 7721
• CHEBI:296881
• EINECS 202-215-7
• BRN 0518285
• UNII-1YY04E7RR4
• 1YY04E7RR4
• CHEMBL118903
• NSC-7721
• EC 202-215-7
• veratrumsyre-
• Spectrum_000512
• Spectrum2_001082
• Spectrum3_001774
• Spectrum4_001582
• Spectrum5_000264
• 3,4-Dimethoxyenzioc acid
• 3,4 dimethoxybenzoic acid
• 3,4-dimethoxybenzoic-acid
• 3,4dimethoxy benzoic acid
• bmse010207
• Epitope ID:119695
• VERATRIC ACID [MI]
• 3,4-Dimethoxy benzoic acid
• BSPBio_003267
• KBioGR_002164
• KBioSS_000992
• SPECTRUM212140
• VERATRIC ACID [INCI]
• MLS002207141
• SCHEMBL114848
• SPBio_001124
• METHYL2-BENZYLOXYBENZOATE
• 3,4-bis(methyloxy)benzoic acid
• DTXSID6059077
• KBio2_000992
• KBio2_003560
• KBio2_006128
• KBio3_002768
• NSC7721
• Protocatechuic Acid Dimethyl Ether
• AMY40073
• HY-N2007
• BBL025942
• BDBM50336487
• CCG-39276
• STK397279
• 3,4-Dimethoxybenzoic acid, >=99%
• AKOS000119433
• BS-3989
• CS-T-46379
• SDCCGMLS-0066972.P001
• NCGC00095539-01
• NCGC00095539-02
• AC-10246
• LS-37122
• SMR000112092
• SY010549
• CS-0018327
• D0631
• FT-0648222
• FT-0667233
• 3,?4-?Dimethoxybenzoic Acid (Veratric Acid)
• EN300-20508
• D71090
• Q425928
• SR-05000002417
• SR-05000002417-1
• W-100257
• BRD-K14520048-001-02-6
• BRD-K14520048-001-04-2
• F2191-0107
• MEBEVERINE HYDROCHLORIDE IMPURITY D [EP IMPURITY]
• Z104478452
• InChI=1/C9H10O4/c1-12-7-4-3-6(9(10)11)5-8(7)13-2/h3-5H,1-2H3,(H,10,11
• TWO

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9829	98.29%
Caco-2	+	0.8211	82.11%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.9143	91.43%
Subcellular localzation	Mitochondria	0.9093	90.93%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9744	97.44%
OATP1B3 inhibitior	+	0.9724	97.24%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9405	94.05%
P-glycoprotein inhibitior	-	0.9618	96.18%
P-glycoprotein substrate	-	0.9553	95.53%
CYP3A4 substrate	-	0.7466	74.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8571	85.71%
CYP3A4 inhibition	-	0.9430	94.30%
CYP2C9 inhibition	-	0.9602	96.02%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9537	95.37%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.4759	47.59%
CYP inhibitory promiscuity	-	0.9062	90.62%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7026	70.26%
Carcinogenicity (trinary)	Non-required	0.6745	67.45%
Eye corrosion	+	0.7114	71.14%
Eye irritation	+	0.9972	99.72%
Skin irritation	+	0.7548	75.48%
Skin corrosion	-	0.9517	95.17%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7415	74.15%
Micronuclear	-	0.5093	50.93%
Hepatotoxicity	+	0.5253	52.53%
skin sensitisation	-	0.8904	89.04%
Respiratory toxicity	-	0.8778	87.78%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	-	0.9125	91.25%
Nephrotoxicity	+	0.4586	45.86%
Acute Oral Toxicity (c)	III	0.5484	54.84%
Estrogen receptor binding	-	0.6516	65.16%
Androgen receptor binding	-	0.8139	81.39%
Thyroid receptor binding	-	0.8360	83.60%
Glucocorticoid receptor binding	-	0.8634	86.34%
Aromatase binding	-	0.7611	76.11%
PPAR gamma	-	0.8029	80.29%
Honey bee toxicity	-	0.9821	98.21%
Biodegradation	+	0.7250	72.50%
Crustacea aquatic toxicity	-	0.9052	90.52%
Fish aquatic toxicity	+	0.9100	91.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL261	P00915	Carbonic anhydrase I	6830 nM	Ki	PMID: 21282059
CHEMBL205	P00918	Carbonic anhydrase II	6180 nM	Ki	PMID: 21282059
CHEMBL3729	P22748	Carbonic anhydrase IV	6480 nM	Ki	PMID: 22687439
CHEMBL3594	Q16790	Carbonic anhydrase IX	8250 nM	Ki	PMID: 21282059
CHEMBL3025	P23280	Carbonic anhydrase VI	24420 nM	Ki	PMID: 22687439
CHEMBL2326	P43166	Carbonic anhydrase VII	7150 nM	Ki	PMID: 22668600
CHEMBL3242	O43570	Carbonic anhydrase XII	6700 nM	Ki	PMID: 21282059
CHEMBL3510	Q9ULX7	Carbonic anhydrase XIV	740 nM; 740 nM	Ki; Ki	PMID: 22668600; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.37%	86.33%
CHEMBL1255126	O15151	Protein Mdm4	93.82%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.72%	99.17%
CHEMBL3194	P02766	Transthyretin	89.50%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.45%	96.09%
CHEMBL2535	P11166	Glucose transporter	87.48%	98.75%
CHEMBL4208	P20618	Proteasome component C5	87.23%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.54%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.98%	96.00%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	83.13%	87.67%

Plants that contains it

• Artemisia capillaris
• Betula pendula
• Chelonanthus albus
• Citrus maxima
• Coriandrum sativum
• Crataegus laevigata
• Cryptocarya amygdalina
• Dendrobium chrysanthum
• Dendrobium chrysotoxum
• Dendrobium fimbriatum
• Dendrobium loddigesii
• Dendrobium moniliforme
• Dendrobium nobile
• Endospermum diadenum
• Ferula latipinna
• Foeniculum vulgare
• Forsythia suspensa
• Forsythia viridissima
• Gardenia jasminoides
• Goniothalamus amuyon
• Gymnacranthera farquhariana var. paniculata
• Handroanthus impetiginosus
• Hypericum laricifolium
• Lysimachia monelli
• Magnolia salicifolia
• Ornithogalum thyrsoides
• Peperomia tetraphylla
• Phaseolus vulgaris
• Phyllanthus oligospermus
• Pulicaria paludosa
• Reynoutria multiflora
• Schisandra sphenanthera
• Spiraea formosana
• Tecomella undulata
• Trifolium pratense
• Trollius chinensis
• Trollius macropetalus
• Viburnum dilatatum

Cross-Links

• PubChem: 7121
• NPASS: NPC285776
• ChEMBL: CHEMBL118903
• LOTUS: LTS0151848
• wikiData: Q425928