Dopamine

Details

• Internal ID: 4b43347f-3590-4847-84dc-e4b98f300db7
• Taxonomy: Benzenoids > Phenols > Benzenediols > Catechols > Catecholamines and derivatives
• IUPAC Name: 4-(2-aminoethyl)benzene-1,2-diol
• SMILES (Canonical): C1=CC(=C(C=C1CCN)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1CCN)O)O
• InChI: InChI=1S/C8H11NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2
• InChI Key: VYFYYTLLBUKUHU-UHFFFAOYSA-N
• Popularity: 218,525 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₁NO₂
• Molecular Weight: 153.18 g/mol
• Exact Mass: 153.078978594 g/mol
• Topological Polar Surface Area (TPSA): 66.50 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): 0.60
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 4-(2-Aminoethyl)benzene-1,2-diol
• 51-61-6
• 3-Hydroxytyramine
• Oxytyramine
• Hydroxytyramin
• Dopamin
• 3,4-dihydroxyphenethylamine
• hydroxytyramine
• intropin
• 4-(2-Aminoethyl)catechol
• 2-(3,4-dihydroxyphenyl)ethylamine
• Dopaminum
• Dophamine
• 4-(2-Aminoethyl)pyrocatechol
• Dopamina
• 3,4-Dihydroxyphenylethylamine
• 4-(2-Aminoethyl)-1,2-benzenediol
• L-DOPAMINE
• ASL 279
• Revimine
• Pyrocatechol, 4-(2-aminoethyl)-
• 1,2-Benzenediol, 4-(2-aminoethyl)-
• Dopaminum [INN-Latin]
• Dopamina [INN-Spanish]
• Dobutamine a
• A-dopamine
• Dopamine [INN:BAN]
• 3-Hydroxtyramine
• KW-3-060
• alpha-(3,4-Dihydroxyphenyl)-beta-aminoethane
• (3H)-Dopamine
• Sinemet
• 4-(2-aminoethyl)-pyrocatechol
• NSC 173182
• HSDB 3068
• UNII-VTD58H1Z2X
• EINECS 200-110-0
• VTD58H1Z2X
• Dopamine (INN)
• NSC-173182
• a-(3,4-Dihydroxyphenyl)-b-aminoethane
• Medopa (TN)
• DTXSID6022420
• CHEBI:18243
• 4-(2-Aminoethyl)-1,2-bezenediol
• Intropin [*hydrochloride*]
• DTXCID602420
• 50444-17-2
• Dopamine (USAN)(*hydrochloride*)
• IP 498
• LDP
• NCGC00015519-05
• 1,2-Benzenediol, 4-(2-aminoethyl)-, labeled with tritium
• Pyrocatechol, 4-(2-aminoethyl)- (8CI)
• DOPAMINE [INN]
• 2-(3,4-dihydroxyphenyl)ethylazanium
• .alpha.-(3,4-Dihydroxyphenyl)-.beta.-aminoethane
• 153C5321-5FEE-4B0B-8925-F388F0EEEBD1
• Pyrocatechol, 4-(2-aminoethyl)-, hydrochloride
• C(CN)c1ccc(O)c(O)c1
• 62-31-7 (HYDROCHLORIDE)
• CAS-51-61-6
• NSC169105
• 1,2-Benzenediol, 4-(2-aminoethyl)- (9CI)
• 4-(2-Aminoethyl)-1,2-benzenediol hydrochloride
• NORADRENALINE TARTRATE IMPURITY C (EP IMPURITY)
• NORADRENALINE TARTRATE IMPURITY C [EP IMPURITY]
• 3,4 Dihydroxyphenethylamine
• dopamin-
• DOBUTAMINE HYDROCHLORIDESPECIFIED IMPURITY A (EP IMPURITY)
• DOBUTAMINE HYDROCHLORIDESPECIFIED IMPURITY A [EP IMPURITY]
• SR-01000075366
• 2-benzenediol
• .beta.-(3,4-Dihydroxyphenyl)ethylamine hydrochloride
• m-Hydroxytyramine-
• Intropin (Salt/Mix)
• Spectrum_001012
• DOPAMINE [HSDB]
• DOPAMINE [MI]
• CHEMBL59
• DOPAMINE [VANDF]
• Spectrum2_001023
• Spectrum3_000406
• Spectrum4_000525
• Spectrum5_000945
• Lopac-H-8502
• Biomol-NT_000001
• bmse000909
• bmse000933
• D0T7OW
• DOPAMINE [WHO-DD]
• 3 4-Dihydroxyphenethylamine
• SCHEMBL8505
• 1, 4-(2-aminoethyl)-
• Lopac0_000586
• Oprea1_088821
• BSPBio_001932
• GTPL940
• KBioGR_001129
• KBioGR_002388
• KBioGR_002484
• KBioSS_001492
• KBioSS_002393
• KBioSS_002491
• 3 4-Dihydroxyphenylethylamine
• cid_65340
• BIDD:ER0506
• DivK1c_000780
• SPECTRUM1505155
• SPBio_001205
• BPBio1_001123
• BDBM55121
• KBio1_000780
• KBio2_001492
• KBio2_002388
• KBio2_002484
• KBio2_004060
• KBio2_004956
• KBio2_005052
• KBio2_006628
• KBio2_007524
• KBio2_007620
• KBio3_001152
• KBio3_002867
• KBio3_002962
• cMAP_000036
• cMAP_000065
• NINDS_000780
• HMS3743I03
• 2-(3 4-Dihydroxyphenyl)ethylamine
• AMY40803
• BCP34189
• Tox21_110167
• 2-(3, 4-Dihydroxyphenyl)ethylamine
• 2-(3,4-dihydroxyphenyl) ethylamine
• 4-(2-Aminoethyl)-1 2-benzenediol
• BBL013043
• LS-159
• MFCD00130258
• NSC173182
• STK301601
• 3,4-DihydroxyphenylA currencythylamin
• 1,2-benzenediol, 4-(2-aminoetil)-
• 2-(34-Dihydroxyphenyl)-1-ethanamine
• AKOS003790978
• Tox21_110167_1
• CCG-204675
• DB00988
• FS-5341
• Pirocatecol, 4-(2-aminoetil)-(8CI)
• Pyrocatechol 4-(2-aminoethyl)-(8CI)
• SDCCGSBI-0050568.P005
• 2-(3,4-Dihydroxyphenyl)-1-ethanamine
• 4-(2-Amino-ethyl)-benzene-1,2-diol
• 4-(2-Aminoethyl)-1,2-benzenediol #
• IDI1_000780
• UPCMLD0ENAT5885989:001
• NCGC00015519-01
• NCGC00015519-02
• NCGC00015519-03
• NCGC00015519-04
• NCGC00015519-07
• NCGC00015519-08
• NCGC00015519-09
• NCGC00015519-10
• NCGC00015519-11
• NCGC00015519-25
• NCGC00096050-01
• NCGC00096050-02
• NCGC00096050-03
• NCGC00096050-04
• NCGC00096050-05
• Pyrocatechol, 4-(2-aminoethyl)-(8CI)
• BP-23276
• 4-(2-aminoethyl)pyrocatechol;hydrochloride
• SBI-0050568.P004
• FT-0698513
• 1,2-Benzenediol, 4-(2-aminoethyl)-(9CI)
• alpha-(3 4-Dihydroxyphenyl)-beta-aminoethane
• EN300-35022
• 2-(4-Hydroxy-5-oxylatophenyl)-1-ethanaminium
• C03758
• D07870
• F21485
• .Alfa. (3,4-dihidroxifenil)-.Beta.-aminoetane
• 4-(2-azanylethyl)benzene-1,2-diol;hydrochloride
• AB00053463-12
• AB00053463_13
• AB00053463_14
• L000232
• Q170304
• SR-01000075366-7
• DOBUTAMINE HYDROCHLORIDE IMPURITY A [EP IMPURITY]
• Oseltamivir-d3;Hydroxytyramin;4-(2-Aminoethyl)benzene-1,2-diol
• 86389-83-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9890	98.90%
Caco-2	+	0.6320	63.20%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4816	48.16%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9736	97.36%
OATP1B3 inhibitior	+	0.9573	95.73%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.9731	97.31%
P-glycoprotein inhibitior	-	0.9883	98.83%
P-glycoprotein substrate	-	0.9468	94.68%
CYP3A4 substrate	-	0.7778	77.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.5494	54.94%
CYP3A4 inhibition	-	0.9001	90.01%
CYP2C9 inhibition	-	0.9459	94.59%
CYP2C19 inhibition	-	0.9477	94.77%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.7091	70.91%
CYP inhibitory promiscuity	-	0.8648	86.48%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.6100	61.00%
Carcinogenicity (trinary)	Non-required	0.7240	72.40%
Eye corrosion	+	0.5311	53.11%
Eye irritation	+	0.7370	73.70%
Skin irritation	+	0.6976	69.76%
Skin corrosion	+	0.5819	58.19%
Ames mutagenesis	+	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6271	62.71%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	+	0.6769	67.69%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.5974	59.74%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.8688	86.88%
Acute Oral Toxicity (c)	III	0.4823	48.23%
Estrogen receptor binding	-	0.5506	55.06%
Androgen receptor binding	+	0.6016	60.16%
Thyroid receptor binding	-	0.7148	71.48%
Glucocorticoid receptor binding	-	0.5609	56.09%
Aromatase binding	-	0.7961	79.61%
PPAR gamma	-	0.6517	65.17%
Honey bee toxicity	-	0.9310	93.10%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	-	0.8979	89.79%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	35481.3 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	6309.6 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	0.0316 nM; 1778.3 nM; 0.0316 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED
CHEMBL4096	P04637	Cellular tumor antigen p53	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	31622.8 nM	Potency	via CMAUP
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	28183.8 nM	Potency	via CMAUP
CHEMBL2056	P21728	Dopamine D1 receptor	192 nM; 130 nM; 20 nM; 124 nM; 12000 nM; 12000 nM; 4470 nM	Ki; Ki; EC50; Ki; Ki; Ki; Ki	PMID: 1973733; PMID: 7658429; via Super-PRED; PMID: 19454369; PMID: 23727194; PMID: 22846798; PMID: 23134120
CHEMBL217	P14416	Dopamine D2 receptor	0.67 nM; 8.00E-06 nM	EC50; IC50	via Super-PRED; PMID: 3156993
CHEMBL234	P35462	Dopamine D3 receptor	5.8 nM; 8.53 nM; 8.53 nM; 8.53 nM; 8.53 nM; 4.76 nM; 4.76 nM; 2.7 nM; 9.3 nM; 9.333 nM; 10.6 nM; 8.57 nM; 7.64 nM; 5.34 nM; 6.1 nM	EC50; EC50; EC50; EC50; EC50; EC50; EC50; EC50; EC50; EC50; EC50; EC50; EC50; EC50; EC50	PMID: 23275802; PMID: 18072730; PMID: 18410082; PMID: 19427222; PMID: 20038106; PMID: 20146482; PMID: 20605099; PMID: 27035329; PMID: 24831693; PMID: 24831693; PMID: 24471976; PMID: 22642365; PMID: 23623679; PMID: 26555041; PMID: 23134120
CHEMBL219	P21917	Dopamine D4 receptor	1.2 nM; 62 nM; 57 nM; 97 nM; 1.2 nM; 6.2 nM; 8.9 nM	Ki; Ki; Ki; Ki; Ki; Ki; Ki	PMID: 10691700; PMID: 10691700; PMID: 10691700; PMID: 10691700; via Super-PRED; PMID: 18834111; PMID: 23428965
CHEMBL1850	P21918	Dopamine D5 receptor	2 nM; 2440 nM	EC50; Ki	via Super-PRED; PMID: 15801855
CHEMBL238	Q01959	Dopamine transporter	460 nM; 460 nM	IC50; IC50	via Super-PRED; PMID: 14592523
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	15848.9 nM; 31622.8 nM; 501.2 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	10000 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	3000 nM	IC50	DOI: 10.1039/C1MD00199J
CHEMBL4040	P28482	MAP kinase ERK2	28183.8 nM	Potency	via CMAUP
CHEMBL1945	P48039	Melatonin receptor 1A	7100 nM	Ki	DOI: 10.1016/S0960-894X(97)00444-7
CHEMBL1946	P49286	Melatonin receptor 1B	9100 nM	Ki	DOI: 10.1016/S0960-894X(97)00444-7
CHEMBL1293224	P10636	Microtubule-associated protein tau	1584.9 nM; 5011.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL222	P23975	Norepinephrine transporter	6.63 nM; 6.63 nM	IC50; IC50	PMID: 14592523; via Super-PRED
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	26121.6 nM; 23280.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293256	P40225	Thrombopoietin	3162.3 nM; 3162.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	1258.9 nM; 446.7 nM; 446.7 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.69%	91.11%
CHEMBL3492	P49721	Proteasome Macropain subunit	94.19%	90.24%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.04%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.29%	96.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.13%	94.45%
CHEMBL3194	P02766	Transthyretin	85.04%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.77%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.39%	99.15%
CHEMBL4581	P52732	Kinesin-like protein 1	82.59%	93.18%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	82.48%	94.01%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.94%	86.33%

Plants that contains it

• Aristolochia gigantea
• Austrocylindropuntia cylindrica
• Clematis parviloba
• Crataegus monogyna
• Cylindropuntia imbricata
• Delphinium pentagynum
• Erythrina crista-galli
• Gnetum montanum
• Lyallia kerguelensis
• Macleaya cordata
• Mirabilis alipes
• Mucuna pruriens
• Musa × paradisiaca
• Papaver bracteatum
• Papaver somniferum
• Portulaca grandiflora
• Portulaca oleracea
• Romneya coulteri
• Senegalia berlandieri
• Solanum tuberosum
• Vachellia rigidula
• Xylopia parviflora
• Zantedeschia aethiopica

Cross-Links

• PubChem: 681
• NPASS: NPC146422
• ChEMBL: CHEMBL59
• LOTUS: LTS0029901
• wikiData: Q170304