1,2-Dimethoxybenzene

Details

• Internal ID: 89895218-96b5-4333-a219-1dc4457fda4d
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Methoxybenzenes > Dimethoxybenzenes
• IUPAC Name: 1,2-dimethoxybenzene
• SMILES (Canonical): COC1=CC=CC=C1OC
• SMILES (Isomeric): COC1=CC=CC=C1OC
• InChI: InChI=1S/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3
• InChI Key: ABDKAPXRBAPSQN-UHFFFAOYSA-N
• Popularity: 1,290 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₀O₂
• Molecular Weight: 138.16 g/mol
• Exact Mass: 138.068079557 g/mol
• Topological Polar Surface Area (TPSA): 18.50 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.70
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• Veratrole
• 91-16-7
• Veratrol
• O-DIMETHOXYBENZENE
• Pyrocatechol dimethyl ether
• Catechol dimethyl ether
• Benzene, 1,2-dimethoxy-
• 2-Methoxyanisole
• O,O-Dimethyl catechol
• 2-Dimethoxybenzol
• Benzene, o-dimethoxy-
• Synthol
• methylguaiacol
• FEMA No. 3799
• Brenzkatechindimethylether
• Methyl guaiacol
• Dimethylether pyrokatechinu
• MFCD00008357
• NSC 16934
• o-dimethoxy-benzene
• Orthodimethoxybenzene
• DIMETHOXYBENZENE
• 1,2-dimethoxy benzene
• 1,2-dimethoxy-benzene
• Dimethylether pyrokatechinu [Czech]
• EINECS 202-045-3
• UNII-61WJZ2Q41I
• AI3-02281
• 61WJZ2Q41I
• CHEMBL1668603
• DTXSID7047065
• CHEBI:59114
• NSC-16934
• EC 202-045-3
• 1,2-Dimethoxybenzene puriss.
• Guaiacol methylether
• veratrol-
• dimethoxy benzene
• 1,2-Dimethoxybenzene (veratrole)
• catechol dimethylether
• Dimethoxybenzene, O-
• VERATROLE [MI]
• Benceno, 1,2-dimetoxi-
• bmse010219
• VERATROL [WHO-DD]
• NCIOpen2_004258
• WLN: 1OR BO1
• ghl.PD_Mitscher_leg0.397
• SCHEMBL105872
• DTXCID5027065
• FEMA 3799
• CS-B1822
• HY-B1812
• NSC16934
• Tox21_302297
• 1,2-DIMETHOXYBENZENE [FHFI]
• BBL011562
• BDBM50336488
• STL146732
• 1,2-Dimethoxybenzene, >=99%, FG
• AKOS000120951
• CCG-327696
• CAS-91-16-7
• NCGC00256103-01
• AS-12860
• LS-29871
• PD158007
• SY001445
• D0627
• FT-0659804
• FT-0664408
• 1,2-Dimethoxybenzene, ReagentPlus(R), 99%
• EN300-16122
• D70447
• 1,2-Dimethoxybenzene, puriss., >=99.0% (GC)
• A843745
• Q131994
• Q-200062
• 1,2-Dimethoxybenzene, Vetec(TM) reagent grade, 98%
• Z53833941
• F1908-0109
• InChI=1/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9972	99.72%
Caco-2	+	0.9369	93.69%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.9000	90.00%
Subcellular localzation	Mitochondria	0.8594	85.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9768	97.68%
OATP1B3 inhibitior	+	0.9845	98.45%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9549	95.49%
P-glycoprotein inhibitior	-	0.9896	98.96%
P-glycoprotein substrate	-	0.9750	97.50%
CYP3A4 substrate	-	0.7423	74.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4320	43.20%
CYP3A4 inhibition	-	0.9505	95.05%
CYP2C9 inhibition	-	0.9678	96.78%
CYP2C19 inhibition	-	0.6180	61.80%
CYP2D6 inhibition	-	0.9436	94.36%
CYP1A2 inhibition	+	0.6298	62.98%
CYP2C8 inhibition	-	0.8877	88.77%
CYP inhibitory promiscuity	-	0.6209	62.09%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7078	70.78%
Carcinogenicity (trinary)	Warning	0.5496	54.96%
Eye corrosion	+	0.9477	94.77%
Eye irritation	+	1.0000	100.00%
Skin irritation	+	0.8218	82.18%
Skin corrosion	-	0.7410	74.10%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5438	54.38%
Micronuclear	-	0.8667	86.67%
Hepatotoxicity	+	0.7409	74.09%
skin sensitisation	+	0.8905	89.05%
Respiratory toxicity	-	0.8889	88.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.9875	98.75%
Nephrotoxicity	+	0.6938	69.38%
Acute Oral Toxicity (c)	III	0.8819	88.19%
Estrogen receptor binding	-	0.9495	94.95%
Androgen receptor binding	-	0.8968	89.68%
Thyroid receptor binding	-	0.8711	87.11%
Glucocorticoid receptor binding	-	0.9305	93.05%
Aromatase binding	-	0.8840	88.40%
PPAR gamma	-	0.9326	93.26%
Honey bee toxicity	-	0.9405	94.05%
Biodegradation	+	0.8000	80.00%
Crustacea aquatic toxicity	+	0.9100	91.00%
Fish aquatic toxicity	+	0.7169	71.69%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL261	P00915	Carbonic anhydrase I	10400 nM; 10400 nM	Ki; Ki	PMID: 22245047; PMID: 21282059
CHEMBL205	P00918	Carbonic anhydrase II	500 nM; 500 nM; 500 nM	Ki; Ki; Ki	PMID: 21282059; via Super-PRED; PMID: 22245047
CHEMBL3729	P22748	Carbonic anhydrase IV	14320 nM; 14320 nM	Ki; Ki	PMID: 22230050; PMID: 22245047
CHEMBL3594	Q16790	Carbonic anhydrase IX	8630 nM	Ki	PMID: 21282059
CHEMBL2326	P43166	Carbonic anhydrase VII	7250 nM	Ki	PMID: 22668600
CHEMBL3242	O43570	Carbonic anhydrase XII	8360 nM	Ki	PMID: 21282059
CHEMBL3510	Q9ULX7	Carbonic anhydrase XIV	6830 nM	Ki	PMID: 22668600

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.60%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.34%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.76%	86.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.73%	89.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.27%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.14%	96.00%
CHEMBL1255126	O15151	Protein Mdm4	83.14%	90.20%
CHEMBL2535	P11166	Glucose transporter	83.02%	98.75%

Plants that contains it

• Acacia paradoxa
• Adonis sutchuenensis
• Astragalus ernestii
• Averrhoa carambola
• Berneuxia thibetica
• Bongardia chrysogonum
• Eragrostis curvula
• Fritillaria meleagris
• Humulus scandens
• Isophysis tasmanica
• Matricaria discoidea
• Metasequoia glyptostroboides
• Ophrys × arachnitiformis
• Petasites japonicus
• Philenoptera laxiflora
• Plantago lundborgii
• Sideritis arborescens
• Silene latifolia
• Solanum pseudoquina
• Triadica sebifera

Cross-Links

• PubChem: 7043
• NPASS: NPC206876
• ChEMBL: CHEMBL1668603
• LOTUS: LTS0266065
• wikiData: Q131994