CHEBI:18053 - 1-aminocyclopropanecarboxylic acid

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ChEBI Name 1-aminocyclopropanecarboxylic acid
ChEBI ID CHEBI:18053
Definition A non-proteinogenic α-amino acid consisting of cyclopropane having amino and carboxy substituents both at the 1-position.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:39590, CHEBI:19027, CHEBI:19028, CHEBI:609
Supplier Information ChemicalBook:CB1384824, eMolecules:502037, ZINC000001600920
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β-Endorphin (beta-endorphin) is an endogenous opioid neuropeptide and peptide hormone that is produced in certain neurons within the central nervous system and peripheral nervous system. It is one of three endorphins that are produced in humans, the others being α-endorphin and γ-endorphin. There are multiple forms of β-endorphins with the full sequence of Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr-Leu-Phe-Lys-Asn-Ala-Ile-Ile-Lys-Asn-Ala-Tyr-Lys-Lys-Gly-Glu (31 amino acids) denoted as β-endorphin(1-31) and variants truncated to the first 26 and 27 amino acids as β-endorphin(1-26) and β-endorphin(1-27). However, β-endorphin(1-31) is the only form that possess a potent analgesic effect and it is the primary form located in the anterior pituitary gland, and regions such as the hypothalamus, midbrain, and amygdala. The first 16 amino acids are identical to α-endorphin. β-Endorphin is considered to be a part of the endogenous opioid and endorphin classes of neuropeptides; all of the established endogenous opioid peptides contain the same N-terminal amino acid sequence, Tyr-Gly-Gly-Phe, followed by either -Met or -Leu. Function of β-endorphin has been known to be associated with hunger, thrill, pain, maternal care, sexual behavior, and reward cognition. In the broadest sense, β-endorphin is primarily utilized in the body to reduce stress and maintain homeostasis. In behavioral research, studies have shown that β-endorphin is released via volume transmission into the ventricular system in response to a variety of stimuli, and novel stimuli in particular.
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Formula C4H7NO2
Net Charge 0
Average Mass 101.10392
Monoisotopic Mass 101.04768
InChI InChI=1S/C4H7NO2/c5-4(1-2-4)3(6)7/h1-2,5H2,(H,6,7)
InChIKey PAJPWUMXBYXFCZ-UHFFFAOYSA-N
SMILES NC1(CC1)C(O)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): ethylene releasers

plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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ChEBI Ontology
Outgoing 1-aminocyclopropanecarboxylic acid (CHEBI:18053) has functional parent cyclopropanecarboxylic acid (CHEBI:23500)
1-aminocyclopropanecarboxylic acid (CHEBI:18053) has role ethylene releasers (CHEBI:24002)
1-aminocyclopropanecarboxylic acid (CHEBI:18053) has role plant metabolite (CHEBI:76924)
1-aminocyclopropanecarboxylic acid (CHEBI:18053) is a monocarboxylic acid (CHEBI:25384)
1-aminocyclopropanecarboxylic acid (CHEBI:18053) is a non-proteinogenic α-amino acid (CHEBI:83925)
1-aminocyclopropanecarboxylic acid (CHEBI:18053) is conjugate acid of 1-aminocyclopropanecarboxylate (CHEBI:30526)
1-aminocyclopropanecarboxylic acid (CHEBI:18053) is tautomer of 1-aminocyclopropanecarboxylic acid zwitterion (CHEBI:58360)
Incoming 1-malonylaminocyclopropanecarboxylic acid (CHEBI:21746) is a 1-aminocyclopropanecarboxylic acid (CHEBI:18053)
1-aminocyclopropanecarboxylate (CHEBI:30526) is conjugate base of 1-aminocyclopropanecarboxylic acid (CHEBI:18053)
1-aminocyclopropanecarboxylic acid zwitterion (CHEBI:58360) is tautomer of 1-aminocyclopropanecarboxylic acid (CHEBI:18053)
IUPAC Name
1-aminocyclopropane-1-carboxylic acid
Synonyms Sources
1-Aminocyclopropane-1-carboxylic acid KEGG COMPOUND
1-AMINOCYCLOPROPANECARBOXYLIC ACID PDBeChem
ACC ChemIDplus
Manual Xrefs Databases
1-Aminocyclopropane-1-carboxylic_acid Wikipedia
1AC PDBeChem
acc Alan Wood's Pesticides
C00007566 KNApSAcK
C01234 KEGG COMPOUND
CPD-68 MetaCyc
DB02085 DrugBank
HMDB0036458 HMDB
View more database links
Registry Numbers Types Sources
2076413 Reaxys Registry Number Reaxys
22059-21-8 CAS Registry Number KEGG COMPOUND
22059-21-8 CAS Registry Number ChemIDplus
362607 Gmelin Registry Number Gmelin
Citations Types Sources
24120532 PubMed citation Europe PMC
24495994 PubMed citation Europe PMC
Last Modified
26 March 2015