CHEBI:22660 - aspartic acid

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ChEBI Name aspartic acid
ChEBI ID CHEBI:22660
Definition An α-amino acid that consists of succinic acid bearing a single α-amino substituent
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB6705020, eMolecules:518145, eMolecules:883971, ZINC000006661227
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l-DOPA, also known as l-3,4-dihydroxyphenylalanine and used medically as levodopa, is made and used as part of the normal biology of some plants and animals, including humans. Humans, as well as a portion of the other animals that utilize l-DOPA, make it via biosynthesis from the amino acid l-tyrosine. l-DOPA is the precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), which are collectively known as catecholamines. Furthermore, l-DOPA itself mediates neurotrophic factor release by the brain and CNS. In some plant families (of the order Caryophyllales), l-DOPA is the central precursor of a biosynthetic pathway that produces a class of pigments called betalains. l-DOPA can be manufactured and in its pure form is sold as a drug with the INNTooltip International Nonproprietary Name levodopa. Trade names include Sinemet, Pharmacopa, Atamet, and Stalevo. As a drug, it is used in the treatment of Parkinson's disease and dopamine-responsive dystonia, as well as restless leg syndrome. l-DOPA has a counterpart with opposite chirality, d-DOPA. As is true for many molecules, the human body produces only one of these isomers (the l-DOPA form). The enantiomeric purity of l-DOPA may be analyzed by determination of the optical rotation or by chiral thin-layer chromatography.
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Formula C4H7NO4
Net Charge 0
Average Mass 133.10272
Monoisotopic Mass 133.03751
InChI InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)
InChIKey CKLJMWTZIZZHCS-UHFFFAOYSA-N
SMILES NC(CC(O)=O)C(O)=O
Metabolite of Species Details
Daphnia magna (NCBI:txid35525) See: Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): fundamental metabolite
Any metabolite produced by all living cells.
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ChEBI Ontology
Outgoing aspartic acid (CHEBI:22660) has part carboxymethyl group (CHEBI:41402)
aspartic acid (CHEBI:22660) has role fundamental metabolite (CHEBI:78675)
aspartic acid (CHEBI:22660) is a α-amino acid (CHEBI:33704)
aspartic acid (CHEBI:22660) is a C4-dicarboxylic acid (CHEBI:66873)
aspartic acid (CHEBI:22660) is a polar amino acid (CHEBI:26167)
aspartic acid (CHEBI:22660) is conjugate acid of aspartate (CHEBI:132943)
aspartic acid (CHEBI:22660) is conjugate acid of aspartate(1−) (CHEBI:35391)
Incoming α-Asp-Leu (CHEBI:68596) has functional parent aspartic acid (CHEBI:22660)
β-Asp-Ile (CHEBI:68601) has functional parent aspartic acid (CHEBI:22660)
β-Asp-Leu (CHEBI:68600) has functional parent aspartic acid (CHEBI:22660)
D-aspartic acid (CHEBI:17364) is a aspartic acid (CHEBI:22660)
L-aspartic acid (CHEBI:17053) is a aspartic acid (CHEBI:22660)
aspartic acid-1,4-13C2 (CHEBI:176633) is a aspartic acid (CHEBI:22660)
aspartate (CHEBI:132943) is conjugate base of aspartic acid (CHEBI:22660)
aspartate(1−) (CHEBI:35391) is conjugate base of aspartic acid (CHEBI:22660)
α-aspartyl group (CHEBI:22445) is substituent group from aspartic acid (CHEBI:22660)
β-aspartyl group (CHEBI:22832) is substituent group from aspartic acid (CHEBI:22660)
aspartic acid residue (CHEBI:32470) is substituent group from aspartic acid (CHEBI:22660)
asparto group (CHEBI:22662) is substituent group from aspartic acid (CHEBI:22660)
aspartoyl group (CHEBI:22663) is substituent group from aspartic acid (CHEBI:22660)
IUPAC Name
aspartic acid
Synonyms Sources
(+-)-Aspartic acid ChemIDplus
(R,S)-Aspartic acid ChemIDplus
2-aminobutanedioic acid IUPAC
Asp ChEBI
Aspartic acid KEGG COMPOUND
D ChEBI
DL-Aminosuccinic acid ChemIDplus
DL-Asparagic acid ChemIDplus
Manual Xrefs Databases
Aspartic_acid Wikipedia
C16433 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
185140 Gmelin Registry Number Gmelin
617-45-8 CAS Registry Number NIST Chemistry WebBook
617-45-8 CAS Registry Number ChemIDplus
774618 Reaxys Registry Number Reaxys
Citation Type Source
22264337 PubMed citation Europe PMC
Last Modified
28 June 2021