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Showing NP-Card for 1-Aminocyclopropane-1-carboxylate (NP0055017)

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Record Information
Version2.0
Created at2022-04-28 01:11:20 UTC
Updated at2022-04-28 01:11:21 UTC
NP-MRD IDNP0055017
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-Aminocyclopropane-1-carboxylate
Description1-Aminocyclopropanecarboxylic acid, also known as ACC or 1-amino-1-carboxycyclopropane, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 1-Aminocyclopropanecarboxylic acid is a very strong basic compound (based on its pKa). 1-Aminocyclopropanecarboxylic acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 1-Aminocyclopropanecarboxylic acid has been detected, but not quantified in, several different foods, such as prairie turnips, lupines, grass pea, towel gourds, and chestnuts. This could make 1-aminocyclopropanecarboxylic acid a potential biomarker for the consumption of these foods. 1-Aminocyclopropane-1-carboxylate is found in Arabidopsis thaliana and Trypanosoma brucei. 1-Aminocyclopropane-1-carboxylate was first documented in 2014 (PMID: 24120532). A non-proteinogenic alpha-amino acid consisting of cyclopropane having amino and carboxy substituents both at the 1-position (PMID: 24495994).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0055017 (1-Aminocyclopropane-1-carboxylate)


  Mrv0541 02231215572D          

  7  7  0  0  0  0            999 V2000
   -0.3938    1.4191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8701    1.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7269    2.2316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6454    1.1369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  END
Download

3D MOL for NP0055017 (1-Aminocyclopropane-1-carboxylate)

     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
   -0.0200   -1.0914    1.2381 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0293   -0.2475    0.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2409   -0.1488   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160   -1.2039   -1.2643 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540    0.9532   -0.7493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2621   -0.0702   -0.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8536    1.0091    0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7282   -1.8608    1.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8995   -1.3715    1.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3635    1.3678    0.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1861   -0.6271   -0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1755    0.2637   -1.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4165    1.9456   -0.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5024    1.0819    1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  6  1  0
  6  7  1  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
  7  2  1  0
  1  8  1  0
  1  9  1  0
  6 11  1  0
  6 12  1  0
  7 13  1  0
  7 14  1  0
  5 10  1  0
M  END
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3D SDF for NP0055017 (1-Aminocyclopropane-1-carboxylate)


  Mrv0541 02231215572D          

  7  7  0  0  0  0            999 V2000
   -0.3938    1.4191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8701    1.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7269    2.2316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6454    1.1369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0055017

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1(CC1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H7NO2/c5-4(1-2-4)3(6)7/h1-2,5H2,(H,6,7)

> <INCHI_KEY>
PAJPWUMXBYXFCZ-UHFFFAOYSA-N

> <FORMULA>
C4H7NO2

> <MOLECULAR_WEIGHT>
101.1039

> <EXACT_MASS>
101.047678473

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
9.602440017818388

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-aminocyclopropane-1-carboxylic acid

> <ALOGPS_LOGP>
-3.05

> <JCHEM_LOGP>
-2.716070759147052

> <ALOGPS_LOGS>
0.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.200941517399801

> <JCHEM_PKA_STRONGEST_BASIC>
9.353636601438382

> <JCHEM_POLAR_SURFACE_AREA>
63.32

> <JCHEM_REFRACTIVITY>
23.2544

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.37e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-aminocyclopropane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0055017 (1-Aminocyclopropane-1-carboxylate)

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PDB for NP0055017 (1-Aminocyclopropane-1-carboxylate)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      -0.735   2.649   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.445   1.659   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.215   0.325   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.325   0.325   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.624   2.649   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.357   4.166   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.071   2.122   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2    4                                                       
CONECT    4    3    2                                                       
CONECT    5    2    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END

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3D PDB for NP0055017 (1-Aminocyclopropane-1-carboxylate)
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SMILES for NP0055017 (1-Aminocyclopropane-1-carboxylate)
NC1(CC1)C(O)=O
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INCHI for NP0055017 (1-Aminocyclopropane-1-carboxylate)
InChI=1S/C4H7NO2/c5-4(1-2-4)3(6)7/h1-2,5H2,(H,6,7)
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View in JSmol
Synonyms
ValueSource
1-Aminocyclopropane-1-carboxylic acidChEBI
ACCChEBI
1-Aminocyclopropane-1-carboxylateGenerator
1-AminocyclopropanecarboxylateGenerator
1-Amino-1-carboxycyclopropaneHMDB
1-Amino-cyclopropanecarboxylic acidHMDB
1-Aminocyclopropane-1-1-carboxylic acidHMDB
1-Aminocyclopropanecarboxylic acid hydrochlorideHMDB
ACPCHMDB
alpha-Aminocyclopropane carboxylic acidHMDB
alpha-Aminocyclopropanecarboxylic acidHMDB
Aminocyclopropane carboxylic acidHMDB
1-Aminocyclopropane-1-carboxylic acid hydrochlorideHMDB
ACC acidHMDB
1-Aminocyclopropane-1-carboxylic acid, 14C-labeledHMDB
1-Aminocyclopropane carboxylic acidHMDB
Chemical FormulaC4H7NO2
Average Mass101.1039 Da
Monoisotopic Mass101.04768 Da
IUPAC Name1-aminocyclopropane-1-carboxylic acid
Traditional Name1-aminocyclopropane-1-carboxylic acid
CAS Registry NumberNot Available
SMILES
NC1(CC1)C(O)=O
InChI Identifier
InChI=1S/C4H7NO2/c5-4(1-2-4)3(6)7/h1-2,5H2,(H,6,7)
InChI KeyPAJPWUMXBYXFCZ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Arabidopsis thalianaPlant
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAlpha amino acids  
Alternative Parents
Substituents
  • Alpha-amino acid
    • 

  • 1-aminocyclopropane-1-carboxylic acid or derivatives
    • 

  • Cyclopropanecarboxylic acid
    • 

  • Cyclopropanecarboxylic acid or derivatives
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic nitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Primary amine
    • 

  • Primary aliphatic amine
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • Organic oxygen compound
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3ALOGPS
logP-2.7ChemAxon
logS0.64ALOGPS
pKa (Strongest Acidic)2.2ChemAxon
pKa (Strongest Basic)9.35ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity23.25 m³·mol⁻¹ChemAxon
Polarizability9.6 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036458  
DrugBank IDDB02085  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030242  
KNApSAcK IDC00007566  
Chemspider ID520  
KEGG Compound IDC01234  
BioCyc IDCPD-68  
BiGG IDNot Available
Wikipedia Link1-Aminocyclopropane-1-carboxylic_acid  
METLIN IDNot Available
PubChem Compound535  
PDB IDNot Available
ChEBI ID18053  
Good Scents IDNot Available
References
General References
  1. Silva PO, Medina EF, Barros RS, Ribeiro DM: Germination of salt-stressed seeds as related to the ethylene biosynthesis ability in three Stylosanthes species. J Plant Physiol. 2014 Jan 1;171(1):14-22. doi: 10.1016/j.jplph.2013.09.004. Epub  2013 Oct 11. [PubMed:24120532  ] 
  2. Shi Y, Wang BL, Shui DJ, Cao LL, Wang C, Yang T, Wang XY, Ye HX: Effect of 1-methylcyclopropene on shelf life, visual quality and nutritional quality of netted melon. Food Sci Technol Int. 2015 Apr;21(3):175-87. doi: 10.1177/1082013214520786. Epub  2014 Feb 4. [PubMed:24495994  ]