Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C4H7NO2 |
| Molecular Weight | 101.1039 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1(CC1)C(O)=O
InChI
InChIKey=PAJPWUMXBYXFCZ-UHFFFAOYSA-N
InChI=1S/C4H7NO2/c5-4(1-2-4)3(6)7/h1-2,5H2,(H,6,7)
1-aminocyclopropanecarboxylic acid (ACPC) is a non-proteinogenic alpha-amino acid consisting of cyclopropane having amino and carboxy substituents both at the 1-position. It has a role as a plant metabolite and a member of ethylene releasers. ACPC is produced endogenously in the tomato and other higher plants as a product of the action of 1-aminocyclopropane-1-carboxylic acid synthase in the biosynthesis of ethylene. It is a monocarboxylic acid and a non-proteinogenic alpha-amino acid. It derives from a cyclopropanecarboxylic acid. ACPC is a partial agonist at the strychnine-insensitive glycine recognition site on the N-methyl-D-aspartate (NMDA) receptor complex in the mammalian central nervous system with preclinical activity in animal models of neuroprotection and psychiatric illnesses. Half-maximal activation by ACPC as a glycine-site agonist was 0.7 to 0.9 microM. Half-maximal inhibition by ACPC was dependent on NMDA concentration. Peak responses to a >100 microM ACPC pulse in the presence of 1 microM glutamate were similar to those of glycine but decayed to a steady-state amplitude below that of glycine. The removal of ACPC initially caused an increase in inward current followed by a subsequent decrease to baseline levels. This suggests that relief of low-affinity antagonism occurs before high-affinity agonist dissociation. ACPC is shown to block convulsions and death produced by NMDA exposure, significantly reducing seizure induction and cell death of NMDA-treated hippocampal neurons.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Reaction intermediate structures of 1-aminocyclopropane-1-carboxylate deaminase: insight into PLP-dependent cyclopropane ring-opening reaction. | 2003-10-17 |
|
| Transformation of Azospirillum brasilense Cd with an ACC deaminase gene from enterobacter cloacae UW4 fused to the Tet r gene promoter improves its fitness and plant growth promoting ability. | 2003-07 |
|
| Carbon dioxide action on ethylene biosynthesis of preclimacteric and climacteric pear fruit. | 2003-06 |
|
| Rapid identification of 1-aminocyclopropane-1-carboxylate (ACC) synthase genotypes in cultivars of Japanese pear (Pyrus pyrifolia Nakai) using CAPS markers. | 2003-05 |
|
| Arabidopsis sulfurtransferases: investigation of their function during senescence and in cyanide detoxification. | 2003-05 |
|
| Asymmetric expression of a poplar ACC oxidase controls ethylene production during gravitational induction of tension wood. | 2003-05 |
|
| Novel broccoli 1-aminocyclopropane-1-carboxylate oxidase gene (Bo-ACO3) associated with the late stage of postharvest floret senescence. | 2003-04-23 |
|
| Comprehensive chemical derivatization for gas chromatography-mass spectrometry-based multi-targeted profiling of the major phytohormones. | 2003-04-18 |
|
| Extraction and quantitative analysis of 1-aminocyclopropane-1-carboxylic acid in plant tissue by gas chromatography coupled to mass spectrometry. | 2003-04-18 |
|
| Role of the Arabidopsis glucose sensor HXK1 in nutrient, light, and hormonal signaling. | 2003-04-11 |
|
| Structure of 1-aminocyclopropane-1-carboxylate synthase in complex with an amino-oxy analogue of the substrate: implications for substrate binding. | 2003-04-11 |
|
| A MAPK pathway mediates ethylene signaling in plants. | 2003-03-17 |
|
| Regulation of root elongation under phosphorus stress involves changes in ethylene responsiveness. | 2003-03 |
|
| The Arabidopsis mutant alh1 illustrates a cross talk between ethylene and auxin. | 2003-03 |
|
| Reaction of 1-amino-2-methylenecyclopropane-1-carboxylate with 1-aminocyclopropane-1-carboxylate deaminase: analysis and mechanistic implications. | 2003-02-25 |
|
| [Cloning and sequencing of ACC oxidase gene from sugarcane]. | 2003-01 |
|
| In vitro germination of Striga hermonthica and Striga aspera seeds by 1-aminocyclopropane-1-carboxylic acid. | 2003-01 |
|
| Isolation and characterization of the ACC synthase genes from lettuce (Lactuca sativa L.), and the involvement in low pH-induced root hair initiation. | 2003-01 |
|
| De-submergence-induced ethylene production in Rumex palustris: regulation and ecophysiological significance. | 2003-01 |
|
| Ethylene biosynthesis in detached young persimmon fruit is initiated in calyx and modulated by water loss from the fruit. | 2003-01 |
|
| Prevalence of 1-aminocyclopropane-1-carboxylate deaminase in Rhizobium spp. | 2003 |
|
| Characterizing the stress/defense transcriptome of Arabidopsis. | 2003 |
|
| Apple 1-aminocyclopropane-1-carboxylate synthase in complex with the inhibitor L-aminoethoxyvinylglycine. Evidence for a ketimine intermediate. | 2002-12-20 |
|
| Ethylene synthesis regulated by biphasic induction of 1-aminocyclopropane-1-carboxylic acid synthase and 1-aminocyclopropane-1-carboxylic acid oxidase genes is required for hydrogen peroxide accumulation and cell death in ozone-exposed tomato. | 2002-12 |
|
| Spatio-temporal expression of patatin-like lipid acyl hydrolases and accumulation of jasmonates in elicitor-treated tobacco leaves are not affected by endogenous levels of salicylic acid. | 2002-12 |
|
| Isolation and characterization of a potato cDNA corresponding to a 1-aminocyclopropane-1-carboxylate (ACC) oxidase gene differentially activated by stress. | 2002-12 |
|
| First intermolecular cyclopropanation of Fischer dialkylaminocarbene complexes. Synthesis of 1-aminocyclopropanecarboxylic acid derivatives. | 2002-11-28 |
|
| Strategies used by rhizobia to lower plant ethylene levels and increase nodulation. | 2002-11 |
|
| Selective blockade of drug-induced place preference conditioning by ACPC, a functional NDMA-receptor antagonist. | 2002-11 |
|
| Dynamic 1-aminocyclopropane-1-carboxylate-synthase and -oxidase transcript accumulation patterns during pollen tube growth in tobacco styles. | 2002-11 |
|
| Molecular characterization and expression analysis of 1-aminocyclopropane-1-carboxylate oxidase homologs from potato under abiotic and biotic stresses. | 2002-10 |
|
| On the mechanism of selectivity of the corn herbicide BAS 662H: a combination of the novel auxin transport inhibitor diflufenzopyr and the auxin herbicide dicamba. | 2002-10 |
|
| An Arabidopsis mutant defective in jasmonate response is allelic to the auxin-signaling mutant axr1. | 2002-10 |
|
| The KNAT2 homeodomain protein interacts with ethylene and cytokinin signaling. | 2002-10 |
|
| Ethylene biosynthesis and action in tomato: a model for climacteric fruit ripening. | 2002-10 |
|
| The novel symbiotic phenotype of enhanced-nodulating mutant of Lotus japonicus: astray mutant is an early nodulating mutant with wider nodulation zone. | 2002-08 |
|
| Loss-of-function mutations in the ethylene receptor ETR1 cause enhanced sensitivity and exaggerated response to ethylene in Arabidopsis. | 2002-08 |
|
| Ethylene perception generates gravicompetence in gravi-incompetent leaves of rye seedlings. | 2002-08 |
|
| The influence of inverted repeats on the production of small antisense RNAs involved in gene silencing. | 2002-07 |
|
| Spatial expression and characterization of a putative ethylene receptor protein NTHK1 in tobacco. | 2002-07 |
|
| The gravitropic setpoint angle of dark-grown rye seedlings and the role of ethylene. | 2002-07 |
|
| Oxygen control of ethylene biosynthesis during seed development in Arabidopsis thaliana (L.) Heynh. | 2002-06 |
|
| SOS4, a pyridoxal kinase gene, is required for root hair development in Arabidopsis. | 2002-06 |
|
| Formation of transfer cells and H(+)-ATPase expression in tomato roots under P and Fe deficiency. | 2002-06 |
|
| The effect of competitive and non-competitive NMDA receptor antagonists, ACPC and MK-801 on NPY and CRF-like immunoreactivity in the rat brain amygdala. | 2002-05-29 |
|
| Subcellular localization of 1-aminocyclopropane-1-carboxylic acid oxidase in apple fruit. | 2002-05 |
|
| Antisense expression of carnation cDNA encoding ACC synthase or ACC oxidase enhances polyamine content and abiotic stress tolerance in transgenic tobacco plants. | 2002-04-30 |
|
| Herbivore-induced volatiles induce the emission of ethylene in neighboring lima bean plants. | 2002-01 |
|
| Characterization of Arabidopsis enhanced disease susceptibility mutants that are affected in systemically induced resistance. | 2002-01 |
|
| Structure, catalytic activity and evolutionary relationships of 1-aminocyclopropane-1-carboxylate synthase, the key enzyme of ethylene synthesis in higher plants. | 2002 |
Patents
Sample Use Guides
Male SHRSP rats were divided into two groups: a control group and an ACPC group administered ACPC at 50 mg/kg per day for 4 weeks by peritoneal injection.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Curator's Comment: In the present experiments, cultured rat spinal cord neurons were used to further examine the effects of acute and sustained ACPC exposures on N-methyl-D-aspartate (NMDA)-induced neurotoxicity. Cell damage was quantitatively assessed using a tetrazolium salt colorimetric assay.
With coincubation, 1 mM ACPC significantly reduced the neuronal cell damage caused by 30 min exposure to 25 or 50 uM concentrations of NMDA, but, in contrast to other competitive and non-competitive NMDA receptor antagonists (D-(-)-2-amino-5-phosphonovaleric acid (APV), dizocilpine maleate (MK-801) and 7-chlorokynurenic acid (7-CK)), it failed to alter the cell injury induced by 100 uM NMDA. The protective effect of ACPC was competitively abolished by coaddition of glycine, verifying that it was mediated through glycine binding sites. Sustained 20 h exposure to 1 mM ACPC (which was removed 30 min before addition of 25 uM NMDA) also caused cells to be significantly less responsive to the neurotoxic effects of NMDA.
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
DTXSID9039577
Created by
admin on Mon Mar 31 18:55:59 GMT 2025 , Edited by admin on Mon Mar 31 18:55:59 GMT 2025
|
PRIMARY | |||
|
535
Created by
admin on Mon Mar 31 18:55:59 GMT 2025 , Edited by admin on Mon Mar 31 18:55:59 GMT 2025
|
PRIMARY | |||
|
40547
Created by
admin on Mon Mar 31 18:55:59 GMT 2025 , Edited by admin on Mon Mar 31 18:55:59 GMT 2025
|
PRIMARY | |||
|
58360
Created by
admin on Mon Mar 31 18:55:59 GMT 2025 , Edited by admin on Mon Mar 31 18:55:59 GMT 2025
|
PRIMARY | |||
|
1-Aminocyclopropane-1-carboxylic acid
Created by
admin on Mon Mar 31 18:55:59 GMT 2025 , Edited by admin on Mon Mar 31 18:55:59 GMT 2025
|
PRIMARY | |||
|
DB02085
Created by
admin on Mon Mar 31 18:55:59 GMT 2025 , Edited by admin on Mon Mar 31 18:55:59 GMT 2025
|
PRIMARY | |||
|
18053
Created by
admin on Mon Mar 31 18:55:59 GMT 2025 , Edited by admin on Mon Mar 31 18:55:59 GMT 2025
|
PRIMARY | |||
|
C023863
Created by
admin on Mon Mar 31 18:55:59 GMT 2025 , Edited by admin on Mon Mar 31 18:55:59 GMT 2025
|
PRIMARY | |||
|
22059-21-8
Created by
admin on Mon Mar 31 18:55:59 GMT 2025 , Edited by admin on Mon Mar 31 18:55:59 GMT 2025
|
PRIMARY | |||
|
98430
Created by
admin on Mon Mar 31 18:55:59 GMT 2025 , Edited by admin on Mon Mar 31 18:55:59 GMT 2025
|
PRIMARY | |||
|
30526
Created by
admin on Mon Mar 31 18:55:59 GMT 2025 , Edited by admin on Mon Mar 31 18:55:59 GMT 2025
|
PRIMARY | |||
|
3K9EJ633GL
Created by
admin on Mon Mar 31 18:55:59 GMT 2025 , Edited by admin on Mon Mar 31 18:55:59 GMT 2025
|
PRIMARY | |||
|
ACC
Created by
admin on Mon Mar 31 18:55:59 GMT 2025 , Edited by admin on Mon Mar 31 18:55:59 GMT 2025
|
PRIMARY |
SUBSTANCE RECORD
