1,3,5-Trimethoxybenzene

Details

• Internal ID: a4d0ae42-6e3c-4adb-9635-72901c683926
• Taxonomy: Benzenoids > Phenol ethers > Anisoles
• IUPAC Name: 1,3,5-trimethoxybenzene
• SMILES (Canonical): COC1=CC(=CC(=C1)OC)OC
• SMILES (Isomeric): COC1=CC(=CC(=C1)OC)OC
• InChI: InChI=1S/C9H12O3/c1-10-7-4-8(11-2)6-9(5-7)12-3/h4-6H,1-3H3
• InChI Key: LKUDPHPHKOZXCD-UHFFFAOYSA-N
• Popularity: 446 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₂O₃
• Molecular Weight: 168.19 g/mol
• Exact Mass: 168.078644241 g/mol
• Topological Polar Surface Area (TPSA): 27.70 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.71
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• 621-23-8
• Phloroglucinol trimethyl ether
• sym-Trimethoxybenzene
• Benzene, 1,3,5-trimethoxy-
• 1,3,5-Trimethyoxybenzene
• MFCD00008385
• O,O,O-1,3,5-Trimethylresorcinol
• EINECS 210-673-4
• NSC 90060
• UNII-00VJI3VG3D
• BRN 1307993
• 00VJI3VG3D
• DTXSID0045963
• CHEBI:31038
• NSC-90060
• NCGC00095239-01
• 4-06-00-07362 (Beilstein Handbook Reference)
• DTXCID8025963
• 1,3,5-Trimethoxybenzene (JAN)
• 1,3,5-TRIMETHOXYBENZENE [JAN]
• CAS-621-23-8
• 1,3,5-Trimethoxy benzene
• 1,5-Trimethoxybenzene
• Spectrum_001404
• 1,5-Trimethyoxybenzene
• 1,3,5-trimethoxybenzol
• Spectrum2_000426
• Spectrum3_001030
• Spectrum4_001163
• Spectrum5_001766
• 1,3,5 -trimethoxybenzene
• 1,3,5-trimethoxy-benzene
• 2,4,6-Trimethoxy-benzene
• NCIOpen2_001419
• SCHEMBL28493
• BSPBio_002819
• KBioGR_001765
• KBioSS_001884
• SPECTRUM231043
• MLS002207155
• SPBio_000412
• CHEMBL1605492
• KBio2_001884
• KBio2_004452
• KBio2_007020
• KBio3_002039
• HMS1763E15
• HMS1923E11
• HY-Y0678
• NSC90060
• Tox21_111489
• CCG-39953
• s6294
• AKOS000120577
• Tox21_111489_1
• AM10837
• CS-W009141
• TRIMETHYLPHLOROGLUCINOL [WHO-DD]
• NCGC00095239-02
• NCGC00095239-03
• NCGC00095239-05
• AS-10870
• LS-32251
• SMR001306732
• SY018307
• FT-0606514
• P0250
• PHLOROGLUCINOL TRIMETHYL ETHER [INCI]
• EN300-16208
• D01792
• D70893
• A833592
• 1,3,5-Trimethoxybenzene, ReagentPlus(R), >=99%
• Q-200071
• BRD-K81884069-001-02-8
• BRD-K81884069-001-03-6
• Q27114090
• Z54718053
• 1,3,5-Trimethoxybenzene, Vetec(TM) reagent grade, 98%
• 1,3,5-Trimethoxybenzene, Standard for quantitative NMR, TraceCERT(R)
• InChI=1/C9H12O3/c1-10-7-4-8(11-2)6-9(5-7)12-3/h4-6H,1-3H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9963	99.63%
Caco-2	+	0.7025	70.25%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.8857	88.57%
Subcellular localzation	Mitochondria	0.8327	83.27%
OATP2B1 inhibitior	-	0.8664	86.64%
OATP1B1 inhibitior	+	0.9601	96.01%
OATP1B3 inhibitior	+	0.9814	98.14%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8932	89.32%
P-glycoprotein inhibitior	-	0.9783	97.83%
P-glycoprotein substrate	-	0.9894	98.94%
CYP3A4 substrate	-	0.8122	81.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4320	43.20%
CYP3A4 inhibition	-	0.8713	87.13%
CYP2C9 inhibition	-	0.9912	99.12%
CYP2C19 inhibition	-	0.8797	87.97%
CYP2D6 inhibition	-	0.9620	96.20%
CYP1A2 inhibition	+	0.5177	51.77%
CYP2C8 inhibition	-	0.9769	97.69%
CYP inhibitory promiscuity	-	0.7124	71.24%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6027	60.27%
Carcinogenicity (trinary)	Non-required	0.5502	55.02%
Eye corrosion	+	0.8003	80.03%
Eye irritation	+	0.9937	99.37%
Skin irritation	+	0.5764	57.64%
Skin corrosion	-	0.9587	95.87%
Ames mutagenesis	-	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7064	70.64%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.5210	52.10%
skin sensitisation	-	0.7943	79.43%
Respiratory toxicity	-	0.9667	96.67%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.9625	96.25%
Nephrotoxicity	+	0.5176	51.76%
Acute Oral Toxicity (c)	III	0.7908	79.08%
Estrogen receptor binding	-	0.9067	90.67%
Androgen receptor binding	-	0.7637	76.37%
Thyroid receptor binding	-	0.7016	70.16%
Glucocorticoid receptor binding	-	0.8612	86.12%
Aromatase binding	-	0.7641	76.41%
PPAR gamma	-	0.8054	80.54%
Honey bee toxicity	-	0.9461	94.61%
Biodegradation	+	0.6500	65.00%
Crustacea aquatic toxicity	+	0.8200	82.00%
Fish aquatic toxicity	+	0.6649	66.49%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	1887 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.56%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.68%	91.11%
CHEMBL4208	P20618	Proteasome component C5	84.33%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.11%	95.56%

Plants that contains it

• Croton lechleri
• Dendrobium chrysanthum
• Harungana madagascariensis
• Pulicaria laciniata
• Rosa chinensis
• Ticorea longiflora
• Zieria chevalieri

Cross-Links

• PubChem: 69301
• NPASS: NPC47422
• ChEMBL: CHEMBL1605492
• LOTUS: LTS0018568
• wikiData: Q104995716