Cannabis Compound Database: Showing Compound Card for Dopamine (CDB005278)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (11)transporters (5) Show 33 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:27:10 UTC

Updated at

2020-12-07 19:11:53 UTC

CannabisDB ID

CDB005278

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Dopamine

Description

Dopamine, also known as 3-hydroxytyramine or deoxyepinephrine, belongs to the class of organic compounds known as catecholamines and derivatives. Catecholamines and derivatives are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution. Dopamine is a drug which is used for the correction of hemodynamic imbalances present in the shock syndrome due to myocardial infarction, trauma, endotoxic septicemia, open-heart surgery, renal failure, and chronic cardiac decompensation as in congestive failure. Dopamine is a very strong basic compound (based on its pKa). Dopamine exists in all living organisms, ranging from bacteria to humans. Within humans, dopamine participates in a number of enzymatic reactions. In particular, dopamine can be biosynthesized from tyramine; which is catalyzed by the enzyme tyrosinase. In addition, dopamine and ascorbic acid can be converted into norepinephrine and dehydroascorbic acid; which is mediated by the enzyme dopamine beta-hydroxylase. Catechol in which the hydrogen at position 4 is substituted by a 2-aminoethyl group. In humans, dopamine is involved in disulfiram action pathway. Outside of the human body, Dopamine is found, on average, in the highest concentration within a few different foods, such as swiss chards, oats, and red beetroots and in a lower concentration in green zucchinis, broccoli, and yellow bell peppers. Dopamine has also been detected, but not quantified in, several different foods, such as potato, banana, avocado, eggplants, and custard apples. This could make dopamine a potential biomarker for the consumption of these foods. Dopamine is a potentially toxic compound. Dopamine, with regard to humans, has been found to be associated with several diseases such as bacterial meningitis, eosinophilic esophagitis, cerebral infarction, and schizophrenia; dopamine has also been linked to the inborn metabolic disorder aromatic l-amino acid decarboxylase deficiency. Dopamine is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)ethylamine	ChEBI
3,4-Dihydroxyphenethylamine	ChEBI
3-Hydroxytyramine	ChEBI
4-(2-Aminoethyl)-1,2-benzenediol	ChEBI
4-(2-Aminoethyl)benzene-1,2-diol	ChEBI
4-(2-Aminoethyl)catechol	ChEBI
4-(2-Aminoethyl)pyrocatechol	ChEBI
Deoxyepinephrine	ChEBI
Dopamina	ChEBI
Dopaminum	ChEBI
Hydroxytyramin	ChEBI
Medopa	Kegg
3,4-Dihydroxyphenylethylamine	HMDB
4-(2-Aminoethyl)-pyrocatechol	HMDB
a-(3,4-Dihydroxyphenyl)-b-aminoethane	HMDB
alpha-(3,4-Dihydroxyphenyl)-beta-aminoethane	HMDB
Dopamin	HMDB
Dopastat	HMDB
Dophamine	HMDB
Dynatra	HMDB
Hydroxytyramine	HMDB
Intropin	HMDB
Oxytyramine	HMDB
Revivan	HMDB
3,4 Dihydroxyphenethylamine	HMDB
Hydrochloride, dopamine	HMDB
Dopamine hydrochloride	HMDB

Chemical Formula

C₈H₁₁NO₂

Average Molecular Weight

153.18

Monoisotopic Molecular Weight

153.079

IUPAC Name

4-(2-aminoethyl)benzene-1,2-diol

Traditional Name

dopamine

CAS Registry Number

50444-17-2

SMILES

NCCC1=CC(O)=C(O)C=C1

InChI Identifier

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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catecholamines and derivatives. Catecholamines and derivatives are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Catecholamines and derivatives

Alternative Parents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

catecholamine (CHEBI:18243 )
Biogenic amines (C03758 )
Tyramine derivatives (C03758 )
Dopamine (C03758 )

Ontology

Hypothyroidism

Disposition

Route of exposure:

Enteral:

Ingestion

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Indirect biological role:

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	128 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	535 mg/mL	Not Available
logP	-0.98	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-0.4	ALOGPS
logP	0.03	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	10.01	ChemAxon
pKa (Strongest Basic)	9.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	66.48 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	43.25 m³·mol⁻¹	ChemAxon
Polarizability	16.21 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00e9-8900000000-88acdc978fe4a64e0fc5	Spectrum
GC-MS	Dopamine, non-derivatized, GC-MS Spectrum	splash10-00di-1900000000-117a1a7207245f5377e7	Spectrum
GC-MS	Dopamine, 4 TMS, GC-MS Spectrum	splash10-00di-1900000000-8b7dcae82868308513da	Spectrum
GC-MS	Dopamine, non-derivatized, GC-MS Spectrum	splash10-00di-1900000000-117a1a7207245f5377e7	Spectrum
GC-MS	Dopamine, non-derivatized, GC-MS Spectrum	splash10-00di-1900000000-8b7dcae82868308513da	Spectrum
Predicted GC-MS	Dopamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-8900000000-752bc8c11fa321b8a7ac	Spectrum
Predicted GC-MS	Dopamine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0089-9280000000-c894c19dda88ac048dd4	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0uxu-4900000000-ff51177ebcb89b8c956c	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9200000000-a554eb700a06cecb8292	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014l-9000000000-db9813e1025f237a549b	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0900000000-27e0d71db6d14d79759c	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0uk9-0900000000-f1cf97c0d0dd509e229e	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-0900000000-aa09a2411e287abe74ed	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00di-1900000000-97c42b109cab2005373d	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-006x-9700000000-974bd18febffcceea2d6	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0f79-0900000000-099173d4201beca9e548	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-1900000000-9dc09f2661247c9d84b0	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0006-9300000000-8b85fa9aac1ffb4c2873	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0006-9000000000-9ea16d2057010279d433	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014l-9000000000-32ca2db8fe2b4729ab94	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0f79-0900000000-ff587935c79b4592ffcf	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-1900000000-8a35d8a2241bc18d6c50	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0006-9300000000-356a4b8f268863c7893e	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0006-9000000000-a88c1004f357858fbc6c	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014l-9000000000-271874005dcb90288512	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0udi-0900000000-cfa7e1cb9f02ffb4447d	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0900000000-4e409c6edda911de39fe	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1900000000-90aa0e0866454c2eacc7	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-1000-9400000000-210fd696305d8cf76164	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-ff95007680e484d3c57e	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1900000000-6dcfecebbd98220ef746	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kil-6900000000-f476cfd569c441bc84aa	Spectrum

NMR

Type	Description		View
1D NMR	1H NMR Spectrum		Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum		Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Tyrosine Metabolism
Catecholamine Biosynthesis
Aromatic L-Aminoacid Decarboxylase Deficiency		Not Available
Tyrosine hydroxylase deficiency		Not Available
Alkaptonuria		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Tyrosinase	TYR	11q14-q21	P14679	details
Amine oxidase [flavin-containing] B	MAOB	Xp11.23	P27338	details
Amine oxidase [flavin-containing] A	MAOA	Xp11.3	P21397	details
Dopamine beta-hydroxylase	DBH	9q34	P09172	details
Catechol O-methyltransferase	COMT	22q11.21	P21964	details
Aromatic-L-amino-acid decarboxylase	DDC	7p12.2	P20711	details
Amiloride-sensitive amine oxidase [copper-containing]	ABP1	7q36.1	P19801	details
Membrane primary amine oxidase	AOC3	17q21	Q16853	details
Retina-specific copper amine oxidase	AOC2	17q21	O75106	details
D(2) dopamine receptor	DRD2	11q23	P14416	details
D(4) dopamine receptor	DRD4	11p15.5	P21917	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Solute carrier family 22 member 5	SLC22A5	5q31	O76082	details
Sodium-dependent dopamine transporter	SLC6A3	5p15.3	Q01959	details
Solute carrier family 22 member 1	SLC22A1	6q26	O15245	details
Solute carrier family 22 member 2	SLC22A2	6q26	O15244	details
Solute carrier family 22 member 3	SLC22A3	6q25.3	O75751	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Dopamine beta-hydroxylase	DBH	9q34	P09172	details
Catechol O-methyltransferase	COMT	22q11.21	P21964	details
Amiloride-sensitive amine oxidase [copper-containing]	ABP1	7q36.1	P19801	details
Membrane primary amine oxidase	AOC3	17q21	Q16853	details
Retina-specific copper amine oxidase	AOC2	17q21	O75106	details
Cytochrome P450 2C9	CYP2C9	10q24	P11712	details
Cytochrome P450 2C19	CYP2C19	10q24	P33261	details
Cytochrome P450 2D6	CYP2D6	22q13.1	P10635	details
Cytochrome P450 1A2	CYP1A2	15q24.1	P05177	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Amiloride-sensitive amine oxidase [copper-containing]	ABP1	7q36.1	P19801	details
D(2) dopamine receptor	DRD2	11q23	P14416	details
D(4) dopamine receptor	DRD4	11p15.5	P21917	details
Neuron-specific vesicular protein calcyon	CALY	10q26.3	Q9NYX4	details
D(3) dopamine receptor	DRD3	3q13.3	P35462	details
D(1A) dopamine receptor	DRD1	5q35.1	P21728	details
D(1B) dopamine receptor	DRD5	4p16.1	P21918	details
Dopamine D4 receptor	dopamine D4 receptor		Q99586	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000073

DrugBank ID

DB00988

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

681

PDB ID

Not Available

ChEBI ID

18243

References

General References

Not Available

Only showing the first 10 proteins. There are 33 proteins in total.

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Enzymes

Enzyme Details

1. Tyrosinase

General function:: Involved in oxidoreductase activity
Specific function:: This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:: TYR
Uniprot ID:: P14679
Molecular weight:: 60392.69

Enzyme Details

2. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Enzyme Details

3. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

Enzyme Details

4. Dopamine beta-hydroxylase

General function:: Involved in monooxygenase activity
Specific function:: Conversion of dopamine to noradrenaline.
Gene Name:: DBH
Uniprot ID:: P09172
Molecular weight:: 69064.45

Enzyme Details

5. Catechol O-methyltransferase

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:: COMT
Uniprot ID:: P21964
Molecular weight:: 30036.77

Enzyme Details

6. Aromatic-L-amino-acid decarboxylase

General function:: Involved in carboxy-lyase activity
Specific function:: Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:: DDC
Uniprot ID:: P20711
Molecular weight:: 53893.755

Enzyme Details

7. Amiloride-sensitive amine oxidase [copper-containing]

General function:: Involved in copper ion binding
Specific function:: Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:: ABP1
Uniprot ID:: P19801
Molecular weight:: 85377.1

Enzyme Details

8. Membrane primary amine oxidase

General function:: Involved in copper ion binding
Specific function:: Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:: AOC3
Uniprot ID:: Q16853
Molecular weight:: 84621.27

Enzyme Details

9. Retina-specific copper amine oxidase

General function:: Involved in copper ion binding
Specific function:: Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:: AOC2
Uniprot ID:: O75106
Molecular weight:: 80515.11

Enzyme Details

10. D(2) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD2
Uniprot ID:: P14416
Molecular weight:: 50618.9

Transporters

Enzyme Details

1. Solute carrier family 22 member 5

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:: SLC22A5
Uniprot ID:: O76082
Molecular weight:: 62751.1

Enzyme Details

2. Sodium-dependent dopamine transporter

General function:: Involved in neurotransmitter:sodium symporter 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

Enzyme Details

3. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

Enzyme Details

4. Solute carrier family 22 member 2

General function:: Involved in ion transmembrane transporter activity
Specific function:: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:: SLC22A2
Uniprot ID:: O15244
Molecular weight:: 62564.0

Enzyme Details

5. Solute carrier family 22 member 3

General function:: Involved in transmembrane transport
Specific function:: Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:: SLC22A3
Uniprot ID:: O75751
Molecular weight:: 61279.5

Only showing the first 10 proteins. There are 33 proteins in total.

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Showing Compound Card for Dopamine (CDB005278)

Structure for CDB005278 (Dopamine)

Enzymes

Transporters