ChemFOnt: Showing chemical card for N-Acetyldopamine (CFc000022768)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:15:13 UTC

Chemfont ID

CFc000022768

Molecule Identification

Common Name

N-Acetyldopamine

Definition

N-Acetyldopamine also known as NADA is an acetylated form of dopamine. It is an endogenously produced derivative or metabolite of dopamine. It belongs to the family of 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. While NADA has been found in the human liver, kidney, and urine, it is unclear what its role is in mammal physiology (PMID: 16179545 ). NADA exists in both free and conjugated (glucuronide) forms. Conjugated NADA accounts for about 90% of the total excretion of NADA. Urinary excretion of total N-acetyldopamine averages 0.485 micromoles/day in healthy humans (PMID: 6513727 ). The concentration of NADA is thirteen times higher in children with neuroblastoma than in normal subjects (PMID: 1321164 ). NADA is known to be a sepiapterin reductase inhibitor (PMID: 16179545 ). N-acetyldopamine has been shown to inhibit lipopolysaccharide-induced lipid peroxidation in rat brains (PMID: 16179545 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-Acetyl-dopamine	ChEBI
NADA	ChEBI
NSC 314644	ChEBI
N-(2-(3,4-Dihydroxyphenyl)ethyl)acetamide (acd/name 4.0)	HMDB
N-(3,4-Dihydroxyphenethyl)-acetamide	HMDB
{N-[2-(3,} 4-dihydroxyphenyl)ethyl]-acetamide	HMDB
N-Acetyldopamine hydrobromide	HMDB

Chemical Formula

C₁₀H₁₃NO₃

Average Molecular Weight

195.2151

Monoisotopic Molecular Weight

195.089543287

IUPAC Name

N-[2-(3,4-dihydroxyphenyl)ethyl]ethanimidic acid

Traditional Name

N-[2-(3,4-dihydroxyphenyl)ethyl]ethanimidic acid

CAS Registry Number

2494-12-4

SMILES

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

InChI Identifier

InChI=1S/C10H13NO3/c1-7(12)11-5-4-8-2-3-9(13)10(14)6-8/h2-3,6,13-14H,4-5H2,1H3,(H,11,12)

InChI Key

OFSAJYZMIPNPHE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0041943)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.62 g/L	ALOGPS
logP	1.12	ALOGPS
logP	0.98	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	6.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.05 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	53.21 m³·mol⁻¹	ChemAxon
Polarizability	20.52 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0041943

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB111680

KNApSAcK ID

C00033243

Chemspider ID

90825

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100526

PDB ID

Not Available

ChEBI ID

125678

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for N-Acetyldopamine (CFc000022768)

MOL for CFc000022768 (N-Acetyldopamine)

3D MOL for CFc000022768 (N-Acetyldopamine)

3D SDF for CFc000022768 (N-Acetyldopamine)

3D-SDF for CFc000022768 (N-Acetyldopamine)

PDB for CFc000022768 (N-Acetyldopamine)

3D PDB for CFc000022768 (N-Acetyldopamine)

SMILES for CFc000022768 (N-Acetyldopamine)

INCHI for CFc000022768 (N-Acetyldopamine)

Structure for CFc000022768 (N-Acetyldopamine)

3D Structure for CFc000022768 (N-Acetyldopamine)