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Showing NP-Card for (+)-(1s,2s)-coronamic acid (NP0161348)

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Record Information
Version2.0
Created at2022-09-02 19:29:56 UTC
Updated at2022-09-02 19:29:56 UTC
NP-MRD IDNP0161348
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-(1s,2s)-coronamic acid
Description(1S,2S)-1-amino-2-ethylcyclopropanecarboxylic acid, also known as 1-AEC, belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom. (+)-(1s,2s)-coronamic acid is found in Pseudomonas syringae. Based on a literature review very few articles have been published on (1S,2S)-1-amino-2-ethylcyclopropanecarboxylic acid.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0161348 ((+)-(1s,2s)-coronamic acid)


  Mrv1652309022221292D          

  9  9  0  0  1  0            999 V2000
    1.3651   -1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  1  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
    0.2382    0.8888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2350    1.5646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7114    1.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627    2.3123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5332    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
Download

3D MOL for NP0161348 ((+)-(1s,2s)-coronamic acid)

     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
    2.3433   -0.9591    0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3302    0.1023    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5277    0.4436   -0.2885 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2458   -0.6021   -0.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9089    0.6301   -0.3140 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4089    1.6095   -1.2828 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8046    0.2987    0.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1795    1.2311    1.5648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2538   -0.9781    1.0612 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1008   -1.1683    1.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8758   -0.5184   -0.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7796   -1.8251    0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8475    1.0285    1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7009   -0.2770    1.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1611    1.0782   -0.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3196   -0.6963   -2.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3171   -1.5589   -0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5586    2.5099   -0.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1503    1.2692   -1.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5196   -1.6177    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  1
  7  9  1  0
  7  8  2  0
  5  3  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  6
  4 16  1  0
  4 17  1  0
  6 18  1  0
  6 19  1  0
  9 20  1  0
M  END
Download

3D SDF for NP0161348 ((+)-(1s,2s)-coronamic acid)


  Mrv1652309022221292D          

  9  9  0  0  1  0            999 V2000
    1.3651   -1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  1  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
    0.2382    0.8888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2350    1.5646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7114    1.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627    2.3123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5332    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0161348

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1C[C@@]1(N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO2/c1-2-4-3-6(4,7)5(8)9/h4H,2-3,7H2,1H3,(H,8,9)/t4-,6-/m0/s1

> <INCHI_KEY>
RLHIWMRQDUCBDO-NJGYIYPDSA-N

> <FORMULA>
C6H11NO2

> <MOLECULAR_WEIGHT>
129.159

> <EXACT_MASS>
129.078978598

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
13.455455979296431

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S)-1-amino-2-ethylcyclopropane-1-carboxylic acid

> <ALOGPS_LOGP>
-2.05

> <JCHEM_LOGP>
-1.9062305417905483

> <ALOGPS_LOGS>
0.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4665870646143135

> <JCHEM_PKA_STRONGEST_BASIC>
9.397020308878133

> <JCHEM_POLAR_SURFACE_AREA>
63.32000000000001

> <JCHEM_REFRACTIVITY>
32.327000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-(1S,2S)-coronamic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0161348 ((+)-(1s,2s)-coronamic acid)

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PDB for NP0161348 ((+)-(1s,2s)-coronamic acid)
HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       2.548  -1.985   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.548  -0.445   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       0.445   1.659   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.439   2.921   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.328   2.921   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.677   4.316   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.862   2.786   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3    5                                                       
CONECT    5    4    3    6    7                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0161348 ((+)-(1s,2s)-coronamic acid)
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SMILES for NP0161348 ((+)-(1s,2s)-coronamic acid)
CC[C@H]1C[C@@]1(N)C(O)=O
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INCHI for NP0161348 ((+)-(1s,2s)-coronamic acid)
InChI=1S/C6H11NO2/c1-2-4-3-6(4,7)5(8)9/h4H,2-3,7H2,1H3,(H,8,9)/t4-,6-/m0/s1
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View in JSmol
Synonyms
ValueSource
(+)-(1S,2S)-Coronamic acidChEBI
(+)-(1S,2S)-CoronamateGenerator
(1S,2S)-1-Amino-2-ethylcyclopropanecarboxylateGenerator
1-Amino-2-ethylcyclopropane-1-carboxylic acid, 2H-labeledMeSH
1-Amino-2-ethylcyclopropane-1-carboxylic acid, (1R-cis)-isomerMeSH
1-Amino-2-ethylcyclopropane-1-carboxylic acid, (1R-trans)-isomerMeSH
1-Amino-2-ethylcyclopropane-1-carboxylic acid, (trans)-(+-)-isomerMeSH
1-Amino-2-ethylcyclopropane-1-carboxylic acid, (trans)-isomerMeSH
1-Amino-2-ethylcyclopropane-1-carboxylic acid, (1S-cis)-isomerMeSH
1-Amino-2-ethylcyclopropane-1-carboxylic acid, (1S-trans)-isomerMeSH
1-AECMeSH
1-Amino-2-ethylcyclopropane-1-carboxylic acidMeSH
1-Amino-2-ethylcyclopropane-1-carboxylic acid, (cis)-(+-)-isomerMeSH
Chemical FormulaC6H11NO2
Average Mass129.1590 Da
Monoisotopic Mass129.07898 Da
IUPAC Name(1S,2S)-1-amino-2-ethylcyclopropane-1-carboxylic acid
Traditional Name(+)-(1S,2S)-coronamic acid
CAS Registry NumberNot Available
SMILES
CC[C@H]1C[C@@]1(N)C(O)=O
InChI Identifier
InChI=1S/C6H11NO2/c1-2-4-3-6(4,7)5(8)9/h4H,2-3,7H2,1H3,(H,8,9)/t4-,6-/m0/s1
InChI KeyRLHIWMRQDUCBDO-NJGYIYPDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pseudomonas syringaeLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentD-alpha-amino acids  
Alternative Parents
Substituents
  • D-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
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary aliphatic amine
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • 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-2ALOGPS
logP-1.9ChemAxon
logS0.13ALOGPS
pKa (Strongest Acidic)2.47ChemAxon
pKa (Strongest Basic)9.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.33 m³·mol⁻¹ChemAxon
Polarizability13.46 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9117672  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10942445  
PDB IDNot Available
ChEBI ID18513  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]