Dopamine
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Basic Info
| Common Name | Dopamine(F05332) |
| 2D Structure | |
| Description | One of the catecholamine neurotransmitters in the brain. It is derived from tyrosine and is the precursor to norepinephrine and epinephrine. Dopamine is a major transmitter in the extrapyramidal system of the brain, and important in regulating movement. A family of receptors (receptors, dopamine) mediate its action. [PubChem] |
| FRCD ID | F05332 |
| CAS Number | 51-61-6 |
| PubChem CID | 681 |
| Formula | C8H11NO2 |
| IUPAC Name | 4-(2-aminoethyl)benzene-1,2-diol |
| InChI Key | VYFYYTLLBUKUHU-UHFFFAOYSA-N |
| InChI | InChI=1S/C8H11NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2 |
| Canonical SMILES | C1=CC(=C(C=C1CCN)O)O |
| Isomeric SMILES | C1=CC(=C(C=C1CCN)O)O |
| Wikipedia | Dopamine |
| Synonyms |
dopamine
4-(2-Aminoethyl)benzene-1,2-diol
Hydroxytyramin
Oxytyramine
Dopamin
51-61-6
3-Hydroxytyramine
3,4-dihydroxyphenethylamine
intropin
Dopaminum
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Phenols |
| Subclass | Benzenediols |
| Intermediate Tree Nodes | Catechols |
| Direct Parent | Catecholamines and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Catecholamine - Phenethylamine - 2-arylethylamine - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Aralkylamine - Monocyclic benzene moiety - Amine - Hydrocarbon derivative - Primary amine - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Organic oxygen compound - Organic nitrogen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as catecholamines and derivatives. These are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 153.181 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 2 |
| Complexity | 119 |
| Monoisotopic Mass | 153.079 |
| Exact Mass | 153.079 |
| XLogP | -1 |
| Formal Charge | 0 |
| Heavy Atom Count | 11 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.8414 |
| Human Intestinal Absorption | HIA+ | 0.9547 |
| Caco-2 Permeability | Caco2- | 0.5479 |
| P-glycoprotein Substrate | Non-substrate | 0.5431 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9739 |
| Non-inhibitor | 0.9357 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7115 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4816 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8462 |
| CYP450 2D6 Substrate | Non-substrate | 0.6383 |
| CYP450 3A4 Substrate | Non-substrate | 0.6905 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9046 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9459 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9422 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9477 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9001 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8648 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7712 |
| Non-inhibitor | 0.5715 | |
| AMES Toxicity | AMES toxic | 0.9107 |
| Carcinogens | Non-carcinogens | 0.8642 |
| Fish Toxicity | Low FHMT | 0.7470 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.6401 |
| Honey Bee Toxicity | Low HBT | 0.5857 |
| Biodegradation | Ready biodegradable | 0.7449 |
| Acute Oral Toxicity | III | 0.4823 |
| Carcinogenicity (Three-class) | Non-required | 0.7240 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.7884 | LogS |
| Caco-2 Permeability | 0.6743 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.1415 | LD50, mol/kg |
| Fish Toxicity | 2.0005 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.6029 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Restorative effect of l-Dopa treatment against Ochratoxin A induced neurotoxicity. | Neurochem Int | 2018 Sep | 29627381 |
| Exposure to Far Infrared Ray Protects Methamphetamine-Induced BehavioralSensitization in Glutathione Peroxidase-1 Knockout Mice via AttenuatingMitochondrial Burdens and Dopamine D1 Receptor Activation. | Neurochem Res | 2018 May | 29687308 |
| Fluorometric determination of dopamine by using molybdenum disulfide quantumdots. | Mikrochim Acta | 2018 Mar 20 | 29594717 |
| Combined brain Fe, Cu, Zn and neurometabolite analysis - a new methodology forunraveling the efficacy of transcranial direct current stimulation (tDCS) inappetite control. | Metallomics | 2018 Mar 1 | 29384550 |
| Construction and Characterization of a Novel Sustained-Release Delivery Systemfor Hydrophobic Pesticides Using Biodegradable Polydopamine-Based Microcapsules. | J Agric Food Chem | 2018 Jun 27 | 29847115 |
| Functional coding variation in the presynaptic dopamine transporter associatedwith neuropsychiatric disorders drives enhanced motivation and context-dependent impulsivity in mice. | Behav Brain Res | 2018 Jan 30 | 28964912 |
| Mercuric resistant bacteria Aeromonas exhibits neurologic toxic effects on the developmental motor reflexes, and brain oxidative stress in mice offspring. | Microb Pathog | 2018 Jan | 29197524 |
| Evaluating oral flavorant effects on nicotine self-administration behavior andphasic dopamine signaling. | Neuropharmacology | 2018 Jan | 28943284 |
| Metabolomic analysis of the toxic effect of chronic exposure of cadmium on rat urine. | Environ Sci Pollut Res Int | 2018 Feb | 29168138 |
| Protracted motivational dopamine-related deficits following adolescence sugaroverconsumption. | Neuropharmacology | 2018 Feb | 29146502 |
| Zanthoxylum alatum abrogates lipopolysaccharide-induced depression-like behaviours in mice by modulating neuroinflammation and monoamine neurotransmitters in the hippocampus. | Pharm Biol | 2018 Dec | 29569964 |
| Food additives, food and the concept of 'food addiction': Is stimulation of thebrain reward circuit by food sufficient to trigger addiction? | Pathophysiology | 2018 Apr 12 | 29673924 |
| Brain Renin-Angiotensin System Blockade Attenuates Methamphetamine-InducedHyperlocomotion and Neurotoxicity. | Neurotherapeutics | 2018 Apr | 29464572 |
| Interaction between central GABAA receptor and dopaminergic system on food intakein neonatal chicks: role of D1 and GABAA receptors. | Int J Neurosci | 2018 Apr | 28948862 |
| The Impact of Environmental Mn Exposure on Insect Biology. | Front Genet | 2018 | 29545824 |
| Ethnopharmacology of Love. | Front Pharmacol | 2018 | 30026695 |
| Genetic elimination of dopamine vesicular stocks in the nigrostriatal pathwayreplicates Parkinson's disease motor symptoms without neuronal degeneration inadult mice. | Sci Rep | 2017 Sep 29 | 28963508 |
| The role of dopamine D2 receptors in the nucleus accumbens during taste-aversive learning and memory extinction after long-term sugar consumption. | Neuroscience | 2017 Sep 17 | 28716589 |
| Effects of chronic exposure to octamethylcyclotetrasiloxane anddecamethylcyclopentasiloxane in the aging female Fischer 344 rat. | Toxicol Lett | 2017 Oct 20 | 28842205 |
| Beyond drug-drug interactions: effects of transporter inhibition on endobiotics, nutrients and toxins. | Expert Opin Drug Metab Toxicol | 2017 Oct | 28847160 |
Targets
- General Function:
- Monoamine transmembrane transporter activity
- Specific Function:
- Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A3
- Uniprot ID:
- Q01959
- Molecular Weight:
- 68494.255 Da
References
- Ostadali MR, Ahangari G, Eslami MB, Razavi A, Zarrindast MR, Ahmadkhaniha HR, Boulhari J: The Detection of Dopamine Gene Receptors (DRD1-DRD5) Expression on Human Peripheral Blood Lymphocytes by Real Time PCR. Iran J Allergy Asthma Immunol. 2004 Dec;3(4):169-74. [17301410 ]
- General Function:
- Norepinephrine:sodium symporter activity
- Specific Function:
- Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A2
- Uniprot ID:
- P23975
- Molecular Weight:
- 69331.42 Da
References
- Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS: Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin. Synapse. 2001 Jan;39(1):32-41. [11071707 ]
- General Function:
- Potassium channel regulator activity
- Specific Function:
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name:
- DRD2
- Uniprot ID:
- P14416
- Molecular Weight:
- 50618.91 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
- General Function:
- G-protein coupled amine receptor activity
- Specific Function:
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation.
- Gene Name:
- DRD3
- Uniprot ID:
- P35462
- Molecular Weight:
- 44224.335 Da
References
- Ostadali MR, Ahangari G, Eslami MB, Razavi A, Zarrindast MR, Ahmadkhaniha HR, Boulhari J: The Detection of Dopamine Gene Receptors (DRD1-DRD5) Expression on Human Peripheral Blood Lymphocytes by Real Time PCR. Iran J Allergy Asthma Immunol. 2004 Dec;3(4):169-74. [17301410 ]
- General Function:
- Sh3 domain binding
- Specific Function:
- Dopamine receptor responsible for neuronal signaling in the mesolimbic system of the brain, an area of the brain that regulates emotion and complex behavior. Its activity is mediated by G proteins which inhibit adenylyl cyclase. Modulates the circadian rhythm of contrast sensitivity by regulating the rhythmic expression of NPAS2 in the retinal ganglion cells (By similarity).
- Gene Name:
- DRD4
- Uniprot ID:
- P21917
- Molecular Weight:
- 48359.86 Da
References
- Ostadali MR, Ahangari G, Eslami MB, Razavi A, Zarrindast MR, Ahmadkhaniha HR, Boulhari J: The Detection of Dopamine Gene Receptors (DRD1-DRD5) Expression on Human Peripheral Blood Lymphocytes by Real Time PCR. Iran J Allergy Asthma Immunol. 2004 Dec;3(4):169-74. [17301410 ]
- General Function:
- L-ascorbic acid binding
- Specific Function:
- Conversion of dopamine to noradrenaline.
- Gene Name:
- DBH
- Uniprot ID:
- P09172
- Molecular Weight:
- 69064.45 Da
References
- Goldman JM, Cooper RL, Murr AS: Reproductive functions and hypothalamic catecholamines in response to the soil fumigant metam sodium: adaptations to extended exposures. Neurotoxicol Teratol. 2007 May-Jun;29(3):368-76. Epub 2006 Dec 6. [17258889 ]
- General Function:
- G-protein coupled amine receptor activity
- Specific Function:
- Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
- Gene Name:
- DRD5
- Uniprot ID:
- P21918
- Molecular Weight:
- 52950.5 Da
References
- Ostadali MR, Ahangari G, Eslami MB, Razavi A, Zarrindast MR, Ahmadkhaniha HR, Boulhari J: The Detection of Dopamine Gene Receptors (DRD1-DRD5) Expression on Human Peripheral Blood Lymphocytes by Real Time PCR. Iran J Allergy Asthma Immunol. 2004 Dec;3(4):169-74. [17301410 ]
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various alkaloids and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase activity.
- Gene Name:
- HTR1F
- Uniprot ID:
- P30939
- Molecular Weight:
- 41708.505 Da
References
- Meltzer PC, McPhee M, Madras BK: Synthesis and biological activity of 2-carbomethoxy-3-catechol-8-azabicyclo[3.2.1]octanes. Bioorg Med Chem Lett. 2003 Nov 17;13(22):4133-7. [14592523 ]
- Uniprot ID:
- P21728; P21918
References
- Hubner H, Haubmann C, Utz W, Gmeiner P: Conjugated enynes as nonaromatic catechol bioisosteres: synthesis, binding experiments, and computational studies of novel dopamine receptor agonists recognizing preferentially the D(3) subtype. J Med Chem. 2000 Feb 24;43(4):756-62. [10691700 ]
- General Function:
- Serotonin:sodium symporter activity
- Specific Function:
- Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
- Gene Name:
- SLC6A4
- Uniprot ID:
- P31645
- Molecular Weight:
- 70324.165 Da
References
- Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS: Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin. Synapse. 2001 Jan;39(1):32-41. [11071707 ]
- General Function:
- Monoamine transmembrane transporter activity
- Specific Function:
- Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles. Requisite for vesicular amine storage prior to secretion via exocytosis.
- Gene Name:
- SLC18A2
- Uniprot ID:
- Q05940
- Molecular Weight:
- 55712.075 Da
References
- Gonzalez AM, Walther D, Pazos A, Uhl GR: Synaptic vesicular monoamine transporter expression: distribution and pharmacologic profile. Brain Res Mol Brain Res. 1994 Mar;22(1-4):219-26. [7912402 ]
- General Function:
- G-protein coupled amine receptor activity
- Specific Function:
- Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
- Gene Name:
- DRD1
- Uniprot ID:
- P21728
- Molecular Weight:
- 49292.765 Da
References
- Dolzan V, Plesnicar BK, Serretti A, Mandelli L, Zalar B, Koprivsek J, Breskvar K: Polymorphisms in dopamine receptor DRD1 and DRD2 genes and psychopathological and extrapyramidal symptoms in patients on long-term antipsychotic treatment. Am J Med Genet B Neuropsychiatr Genet. 2007 Sep 5;144B(6):809-15. [17455212 ]
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling inhibits adenylate cyclase activity and activates a phosphatidylinositol-calcium second messenger system that regulates the release of Ca(2+) ions from intracellular stores. Plays a role in the regulation of 5-hydroxytryptamine release and in the regulation of dopamine and 5-hydroxytryptamine metabolism. Plays a role in the regulation of dopamine and 5-hydroxytryptamine levels in the brain, and thereby affects neural activity, mood and behavior. Plays a role in the response to anxiogenic stimuli.
- Gene Name:
- HTR1A
- Uniprot ID:
- P08908
- Molecular Weight:
- 46106.335 Da
References
- Toll L, Berzetei-Gurske IP, Polgar WE, Brandt SR, Adapa ID, Rodriguez L, Schwartz RW, Haggart D, O'Brien A, White A, Kennedy JM, Craymer K, Farrington L, Auh JS: Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications. NIDA Res Monogr. 1998 Mar;178:440-66. [9686407 ]
- General Function:
- Serotonin receptor activity
- Specific Function:
- This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase.
- Gene Name:
- HTR7
- Uniprot ID:
- P34969
- Molecular Weight:
- 53554.43 Da
References
- Lovenberg TW, Baron BM, de Lecea L, Miller JD, Prosser RA, Rea MA, Foye PE, Racke M, Slone AL, Siegel BW, et al.: A novel adenylyl cyclase-activating serotonin receptor (5-HT7) implicated in the regulation of mammalian circadian rhythms. Neuron. 1993 Sep;11(3):449-58. [8398139 ]
- General Function:
- Protein tyrosine kinase activity
- Specific Function:
- Non-receptor tyrosine-protein kinase that plays a role in many biological processes including regulation of cell growth and survival, cell adhesion, integrin-mediated signaling, cytoskeletal remodeling, cell motility, immune response and axon guidance. Inactive FYN is phosphorylated on its C-terminal tail within the catalytic domain. Following activation by PKA, the protein subsequently associates with PTK2/FAK1, allowing PTK2/FAK1 phosphorylation, activation and targeting to focal adhesions. Involved in the regulation of cell adhesion and motility through phosphorylation of CTNNB1 (beta-catenin) and CTNND1 (delta-catenin). Regulates cytoskeletal remodeling by phosphorylating several proteins including the actin regulator WAS and the microtubule-associated proteins MAP2 and MAPT. Promotes cell survival by phosphorylating AGAP2/PIKE-A and preventing its apoptotic cleavage. Participates in signal transduction pathways that regulate the integrity of the glomerular slit diaphragm (an essential part of the glomerular filter of the kidney) by phosphorylating several slit diaphragm components including NPHS1, KIRREL and TRPC6. Plays a role in neural processes by phosphorylating DPYSL2, a multifunctional adapter protein within the central nervous system, ARHGAP32, a regulator for Rho family GTPases implicated in various neural functions, and SNCA, a small pre-synaptic protein. Participates in the downstream signaling pathways that lead to T-cell differentiation and proliferation following T-cell receptor (TCR) stimulation. Also participates in negative feedback regulation of TCR signaling through phosphorylation of PAG1, thereby promoting interaction between PAG1 and CSK and recruitment of CSK to lipid rafts. CSK maintains LCK and FYN in an inactive form. Promotes CD28-induced phosphorylation of VAV1.
- Gene Name:
- FYN
- Uniprot ID:
- P06241
- Molecular Weight:
- 60761.49 Da
References
- Liu T, Lin Y, Wen X, Jorissen RN, Gilson MK: BindingDB: a web-accessible database of experimentally determined protein-ligand binding affinities. Nucleic Acids Res. 2007 Jan;35(Database issue):D198-201. Epub 2006 Dec 1. [17145705 ]