3,4,5-Trimethoxyphenol

Details

• Internal ID: 64e4992d-c596-41b7-967a-9676614ede1b
• Taxonomy: Benzenoids > Phenols > Methoxyphenols
• IUPAC Name: 3,4,5-trimethoxyphenol
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)O
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)O
• InChI: InChI=1S/C9H12O4/c1-11-7-4-6(10)5-8(12-2)9(7)13-3/h4-5,10H,1-3H3
• InChI Key: VTCDZPUMZAZMSB-UHFFFAOYSA-N
• Popularity: 69 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₂O₄
• Molecular Weight: 184.19 g/mol
• Exact Mass: 184.07355886 g/mol
• Topological Polar Surface Area (TPSA): 47.90 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.42
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• Antiarol
• 642-71-7
• Phenol, 3,4,5-trimethoxy-
• MFCD00008389
• CHEBI:2760
• WXG8D4R582
• EINECS 211-387-2
• AI3-38432
• 3,4,5-TRIMETHOXY PHENOL
• Spectrum_000525
• SpecPlus_000623
• 1,3,5-trimethoxyphenol
• Spectrum3_001208
• Spectrum4_001487
• Spectrum5_000193
• 3,4,5-trirnethoxyphenol
• 3,4,5-trimethoxy-phenol
• UNII-WXG8D4R582
• BSPBio_002596
• KBioGR_002093
• KBioSS_001005
• SPECTRUM200110
• DivK1c_006719
• SCHEMBL210578
• CHEMBL1319047
• KBio1_001663
• KBio2_001005
• KBio2_003573
• KBio2_006141
• KBio3_002096
• 3,4,5-Trimethoxyphenol, 97%
• 3,4,5-trimethoxyphenol;Antiarol
• DTXSID20214405
• TRIMETHOXYPHENOL, 3,4,5-
• s4936
• 3',4',5'-TRIMETHOXYPHENOL
• AKOS005258271
• AC-5984
• CCG-214337
• CS-W017005
• GF-0143
• HY-W016289
• NCGC00095916-01
• NCGC00095916-02
• SY061990
• FT-0614170
• FT-0614171
• EN300-80256
• A834698
• SR-05000002420
• SR-05000002420-1
• W-104852
• BRD-K28698314-001-01-3
• BRD-K28698314-001-02-1
• Q27105809
• Z1219738605
• InChI=1/C9H12O4/c1-11-7-4-6(10)5-8(12-2)9(7)13-3/h4-5,10H,1-3H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9822	98.22%
Caco-2	+	0.6828	68.28%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8262	82.62%
OATP2B1 inhibitior	-	0.8617	86.17%
OATP1B1 inhibitior	+	0.9511	95.11%
OATP1B3 inhibitior	+	0.9743	97.43%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9505	95.05%
P-glycoprotein inhibitior	-	0.9709	97.09%
P-glycoprotein substrate	-	0.9796	97.96%
CYP3A4 substrate	-	0.6947	69.47%
CYP2C9 substrate	-	0.7845	78.45%
CYP2D6 substrate	+	0.4222	42.22%
CYP3A4 inhibition	-	0.8694	86.94%
CYP2C9 inhibition	-	0.9924	99.24%
CYP2C19 inhibition	-	0.8607	86.07%
CYP2D6 inhibition	-	0.9368	93.68%
CYP1A2 inhibition	-	0.7735	77.35%
CYP2C8 inhibition	+	0.4526	45.26%
CYP inhibitory promiscuity	-	0.7873	78.73%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7550	75.50%
Carcinogenicity (trinary)	Non-required	0.6154	61.54%
Eye corrosion	+	0.5237	52.37%
Eye irritation	+	0.9907	99.07%
Skin irritation	+	0.5505	55.05%
Skin corrosion	-	0.9130	91.30%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4645	46.45%
Micronuclear	-	0.6467	64.67%
Hepatotoxicity	-	0.6216	62.16%
skin sensitisation	-	0.6669	66.69%
Respiratory toxicity	-	0.8000	80.00%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.9000	90.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.6473	64.73%
Estrogen receptor binding	-	0.8088	80.88%
Androgen receptor binding	-	0.7897	78.97%
Thyroid receptor binding	-	0.6708	67.08%
Glucocorticoid receptor binding	-	0.8891	88.91%
Aromatase binding	-	0.7570	75.70%
PPAR gamma	-	0.8322	83.22%
Honey bee toxicity	-	0.9389	93.89%
Biodegradation	+	0.6000	60.00%
Crustacea aquatic toxicity	+	0.6151	61.51%
Fish aquatic toxicity	+	0.7813	78.13%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	28183.8 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.11%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.12%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.55%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.90%	86.33%
CHEMBL2535	P11166	Glucose transporter	84.94%	98.75%
CHEMBL4208	P20618	Proteasome component C5	84.57%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.89%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.40%	94.00%
CHEMBL1255126	O15151	Protein Mdm4	80.61%	90.20%

Plants that contains it

• Ailanthus altissima
• Ailanthus integrifolia
• Antiaris toxicaria
• Aquilaria sinensis
• Diospyros eriantha
• Drypetes gossweileri
• Gardenia jasminoides
• Lettowianthus stellatus
• Tripterygium wilfordii
• Vitis vinifera

Cross-Links

• PubChem: 69505
• NPASS: NPC232654
• ChEMBL: CHEMBL1319047
• LOTUS: LTS0080994
• wikiData: Q27105809