4-(2-Aminoethyl)-2-methoxyphenol

Details

• Internal ID: 96a453dd-e077-468f-b530-3dd0dd20d360
• Taxonomy: Benzenoids > Phenols > Methoxyphenols
• IUPAC Name: 4-(2-aminoethyl)-2-methoxyphenol
• SMILES (Canonical): COC1=C(C=CC(=C1)CCN)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)CCN)O
• InChI: InChI=1S/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3
• InChI Key: DIVQKHQLANKJQO-UHFFFAOYSA-N
• Popularity: 1,529 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₃NO₂
• Molecular Weight: 167.20 g/mol
• Exact Mass: 167.094628657 g/mol
• Topological Polar Surface Area (TPSA): 55.50 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.90
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 554-52-9
• 3-Methoxytyramine
• 4-(2-Amino-ethyl)-2-methoxy-phenol
• 3-O-methyldopamine
• 3-Methoxy-4-hydroxyphenethylamine
• Methoxytyramine
• Phenol, 4-(2-aminoethyl)-2-methoxy-
• 3-Methoxy-4-hydroxyphenylethyl amine
• Tyramine, 3-methoxy-
• 4-(2-aminoethyl)-2-methoxy-Phenol
• 5-(2-aminoethyl)guaiacol
• JCH2767EDP
• CHEBI:1582
• 4-hydroxy-3-methoxyphenethylamine
• 4-hydroxy-3-methoxyphenylethylamine
• 3-MT
• 4-(2-Amino-ethyl)-2-methoxy-phenol CONTROLLED DRUG CLASS A SCHEDULE 1
• 3-MT . HCl;3-O-Methyldopamine . HCl
• UNII-JCH2767EDP
• HOMOVANILLINAMINE
• HOMOVANILLYLAMINE
• Lopac-M-4251
• 3-Methoxytyramine . HCl
• bmse000929
• bmse000958
• EC 611-267-3
• Lopac0_000796
• SCHEMBL68386
• 3-METHOXY-P-TYRAMINE
• GTPL6642
• MT-3
• CHEMBL1160785
• BDBM85380
• AMY5037
• DTXSID40862189
• cid_11957621
• MFCD00060621
• 4-(2-Aminoethyl)-2-methoxyphenol #
• AKOS000161280
• AC-6711
• CCG-204880
• FS-6018
• GUAIACOL, 4-(2-AMINOETHYL)-
• HY-103638A
• 2-(4-hydroxy-3-methoxyphenyl)ethylamine
• NCGC00015674-01
• NCGC00015674-02
• NCGC00015674-03
• NCGC00162257-01
• NCGC00162257-02
• DOPAMINE IMPURITY B [EP IMPURITY]
• PD046228
• 2-(4-hydroxy-3-methoxyphenyl)-ethylamine
• 2-METHOXY-4-(2-AMINOETHYL)PHENOL
• CAS_1477-68-5
• 2-(4-hydroxy-3-methoxy-phenyl)-ethylamine
• HYDROXY-3-METHOXYPHENETHYLAMINE, 4-
• A8025
• CS-0028515
• FT-0711461
• 4-HYDROXY-3-METHOXY-2-PHENETHYLAMINE
• EN300-66666
• C05587
• 4-HYDROXY-3-METHOXY-.BETA.-PHENETHYLAMINE
• A870191
• L000765
• A1-42513
• Q-102400
• Q4634167
• DOPAMINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]
• 0F899116-F44F-422B-B36A-7F12600FCCBD
• 4-(2-Aminoethyl)-2-methoxyphenol;4-(2-AMINO-ETHYL)-2-METHOXY-PHENOL

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9960	99.60%
Caco-2	+	0.8617	86.17%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6122	61.22%
OATP2B1 inhibitior	-	0.8681	86.81%
OATP1B1 inhibitior	+	0.9499	94.99%
OATP1B3 inhibitior	+	0.9555	95.55%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.9458	94.58%
P-glycoprotein inhibitior	-	0.9867	98.67%
P-glycoprotein substrate	-	0.7944	79.44%
CYP3A4 substrate	-	0.6520	65.20%
CYP2C9 substrate	-	0.8220	82.20%
CYP2D6 substrate	+	0.6598	65.98%
CYP3A4 inhibition	-	0.8308	83.08%
CYP2C9 inhibition	-	0.9472	94.72%
CYP2C19 inhibition	-	0.9148	91.48%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.8360	83.60%
CYP2C8 inhibition	+	0.8526	85.26%
CYP inhibitory promiscuity	-	0.8473	84.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7000	70.00%
Carcinogenicity (trinary)	Non-required	0.6887	68.87%
Eye corrosion	+	0.8761	87.61%
Eye irritation	+	0.7417	74.17%
Skin irritation	+	0.7799	77.99%
Skin corrosion	+	0.5814	58.14%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5624	56.24%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.5915	59.15%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.8557	85.57%
Acute Oral Toxicity (c)	III	0.5246	52.46%
Estrogen receptor binding	-	0.5080	50.80%
Androgen receptor binding	-	0.7199	71.99%
Thyroid receptor binding	-	0.7809	78.09%
Glucocorticoid receptor binding	-	0.7504	75.04%
Aromatase binding	-	0.8277	82.77%
PPAR gamma	-	0.7367	73.67%
Honey bee toxicity	-	0.9586	95.86%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.6251	62.51%
Fish aquatic toxicity	-	0.9559	95.59%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	125.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.13%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.59%	96.09%
CHEMBL3492	P49721	Proteasome Macropain subunit	93.81%	90.24%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.40%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.86%	86.33%
CHEMBL1255126	O15151	Protein Mdm4	90.65%	90.20%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.33%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.69%	94.00%
CHEMBL4581	P52732	Kinesin-like protein 1	85.14%	93.18%
CHEMBL2581	P07339	Cathepsin D	84.63%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.97%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.74%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.61%	95.56%
CHEMBL2535	P11166	Glucose transporter	83.42%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.43%	89.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.96%	92.94%
CHEMBL4208	P20618	Proteasome component C5	80.58%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.58%	99.15%
CHEMBL3194	P02766	Transthyretin	80.55%	90.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.30%	95.50%

Plants that contains it

• Austrocylindropuntia cylindrica
• Backebergia militaris
• Cylindropuntia imbricata
• Lyallia kerguelensis
• Senegalia berlandieri
• Vachellia rigidula

Cross-Links

• PubChem: 1669
• LOTUS: LTS0248517
• wikiData: Q4634167