Deoxyepinephrine

Details

• Internal ID: 2d51b0f6-d7db-4a30-8a3a-03e9de7ea0c9
• Taxonomy: Benzenoids > Phenols > Benzenediols > Catechols > Catecholamines and derivatives
• IUPAC Name: 4-[2-(methylamino)ethyl]benzene-1,2-diol
• SMILES (Canonical): CNCCC1=CC(=C(C=C1)O)O
• SMILES (Isomeric): CNCCC1=CC(=C(C=C1)O)O
• InChI: InChI=1S/C9H13NO2/c1-10-5-4-7-2-3-8(11)9(12)6-7/h2-3,6,10-12H,4-5H2,1H3
• InChI Key: NGKZFDYBISXGGS-UHFFFAOYSA-N
• Popularity: 905 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): 52.50 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): 0.86
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• deoxyepinephrine
• 501-15-5
• N-Methyldopamine
• Desoxyepinephrine
• 4-[2-(methylamino)ethyl]benzene-1,2-diol
• Deoxyadrenaline
• Epyamine
• Epinin
• Deoxyephinephrine
• 4-(2-Methylaminoethyl)pyrocatechol
• UNII-R7339QLN1C
• 1,2-Benzenediol, 4-(2-(methylamino)ethyl)-
• R7339QLN1C
• N-2-(3,4-dihydroxyphenyl)ethylmethylamine
• 4-(2-Methylamino-ethyl)-benzene-1,2-diol
• EINECS 207-919-8
• 3,4-dihydroxy-N-methylphenethylamine
• N-methyl-3,4-dihydroxyphenethylamine
• 1-(3,4-dihydroxyphenyl)-2-methylaminoethane
• CHEBI:10554
• 1,2-Benzenediol, 4-[2-(methylamino)ethyl]-
• 4-(beta-Methylaminoethyl)catechol
• DTXSID10198205
• 4-[2-(Methylamino)ethyl]-1,2-benzenediol
• PYROCATECHOL, 4-(2-(METHYLAMINO)ETHYL)-
• EPININE (USP IMPURITY)
• EPININE [USP IMPURITY]
• Desoxyadrenaline
• 4-(2-(Methylamino)ethyl)-1,2-Benzenediol
• DEOXIEPINEPHRINE
• Lopac-D-5886
• Biomol-NT_000002
• Lopac0_000390
• SCHEMBL67772
• DEOXYEPINEPHRINE [MI]
• CHEMBL31088
• BPBio1_001125
• BDBM81489
• DEOXYEPINEPHRINE [WHO-DD]
• DTXCID00120696
• NSC_4382
• PDSP1_001130
• PDSP2_001114
• 4-[2-(Methylamino)ethyl]pyrocatechol
• AKOS006242434
• CCG-204484
• DB13917
• SDCCGSBI-0050377.P002
• CAS_62-32-8
• NCGC00015355-01
• NCGC00015355-02
• NCGC00015355-03
• NCGC00015355-04
• NCGC00162139-01
• NCGC00162139-02
• FT-0706551
• N-Methyl-2-(3,4-dihydroxyphenyl)ethylamine
• 4-[2-(Methylamino)ethyl]-1,2-benzenediol #
• C07453
• EN300-1869983
• Q5260066
• 1,2-Benzenediol, 4-[2-(methylamino)ethyl]-, hydrobromide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9884	98.84%
Caco-2	-	0.5764	57.64%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5827	58.27%
OATP2B1 inhibitior	-	0.8625	86.25%
OATP1B1 inhibitior	+	0.9499	94.99%
OATP1B3 inhibitior	+	0.9512	95.12%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.9808	98.08%
P-glycoprotein inhibitior	-	0.9823	98.23%
P-glycoprotein substrate	-	0.7730	77.30%
CYP3A4 substrate	-	0.6437	64.37%
CYP2C9 substrate	-	0.6168	61.68%
CYP2D6 substrate	+	0.5954	59.54%
CYP3A4 inhibition	-	0.9215	92.15%
CYP2C9 inhibition	-	0.9447	94.47%
CYP2C19 inhibition	-	0.9588	95.88%
CYP2D6 inhibition	-	0.9256	92.56%
CYP1A2 inhibition	-	0.8017	80.17%
CYP2C8 inhibition	-	0.7754	77.54%
CYP inhibitory promiscuity	-	0.9576	95.76%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7100	71.00%
Carcinogenicity (trinary)	Non-required	0.7792	77.92%
Eye corrosion	-	0.8478	84.78%
Eye irritation	-	0.6655	66.55%
Skin irritation	+	0.6526	65.26%
Skin corrosion	-	0.5000	50.00%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6611	66.11%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.5339	53.39%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6530	65.30%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.7875	78.75%
Acute Oral Toxicity (c)	III	0.4387	43.87%
Estrogen receptor binding	-	0.6071	60.71%
Androgen receptor binding	+	0.7404	74.04%
Thyroid receptor binding	-	0.6717	67.17%
Glucocorticoid receptor binding	-	0.6719	67.19%
Aromatase binding	-	0.7194	71.94%
PPAR gamma	-	0.8864	88.64%
Honey bee toxicity	-	0.9135	91.35%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	-	0.7485	74.85%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	5011.9 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	19952.6 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	3981.07 nM	AC50	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	1258.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	6309.6 nM; 6309.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	5623.4 nM	Potency	via CMAUP
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	2238.7 nM; 2238.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293256	P40225	Thrombopoietin	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.18%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.74%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	90.76%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.02%	96.09%
CHEMBL4208	P20618	Proteasome component C5	86.05%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	85.44%	94.73%
CHEMBL3492	P49721	Proteasome Macropain subunit	85.28%	90.24%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.53%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.81%	96.95%

Plants that contains it

• Brickellia cylindracea
• Calocephalus citreus
• Crotalaria medicaginea
• Cytisus scoparius
• Fritillaria stenanthera
• Genista pichisermolliana
• Kopsia teoi
• Monoon barnesii
• Pinalia floribunda
• Pinalia leucantha
• Rubus lambertianus
• Senegalia berlandieri
• Sidastrum burrerense
• Stevia ovata
• Striga asiatica
• Vachellia rigidula
• Yucca gloriosa var. tristis

Cross-Links

• PubChem: 4382
• NPASS: NPC85276
• ChEMBL: CHEMBL31088
• LOTUS: LTS0162750
• wikiData: Q5260066