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Showing NP-Card for (1r,6s)-6-amino-5-oxocyclohex-2-ene-1-carboxylic acid (NP0217137)

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Record Information
Version2.0
Created at2022-09-05 17:22:48 UTC
Updated at2022-09-05 17:22:48 UTC
NP-MRD IDNP0217137
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,6s)-6-amino-5-oxocyclohex-2-ene-1-carboxylic acid
Description(1R,6S)-6-amino-5-oxocyclohex-2-ene-1-carboxylic acid belongs to the class of organic compounds known as beta amino acids and derivatives. (1r,6s)-6-amino-5-oxocyclohex-2-ene-1-carboxylic acid is found in Apis cerana. These are amino acids having a (-NH2) group attached to the beta carbon atom (1R,6S)-6-amino-5-oxocyclohex-2-ene-1-carboxylic acid is a very strong basic compound (based on its pKa).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0217137 ((1r,6s)-6-amino-5-oxocyclohex-2-ene-1-carboxylic acid)


  Mrv1652307102019192D          

 12 12  0  0  1  0            999 V2000
   -1.0723   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0723   -1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3578   -1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3566   -1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3566   -0.2058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3578    0.2066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3578    1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0822    1.4499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3467    1.4383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822    0.2131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822   -1.4499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0743    0.6202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  6  0  0  0
  4 11  2  0  0  0  0
  6 12  1  6  0  0  0
M  END
Download

3D MOL for NP0217137 ((1r,6s)-6-amino-5-oxocyclohex-2-ene-1-carboxylic acid)

     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
    0.8038    2.0308    0.7220 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1646    1.0220   -0.0742 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3007    1.0373    0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866    1.8730    0.9949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1842   -0.0067   -0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5220   -1.3131   -0.4379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2341   -1.4391   -0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6594   -0.3462    0.2691 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0433   -0.5780   -0.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5632    0.2899   -0.9989 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7798   -1.6812    0.0771 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6568    2.4341    0.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1484    2.8383    0.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2346    1.2270   -1.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5777    0.3229   -1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0772   -0.1437    0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0984   -2.1642   -0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2609   -2.4248   -0.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7278   -0.3954    1.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7381   -2.5829   -0.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  1  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
  2  8  1  0
  8 19  1  1
  7 18  1  0
  6 17  1  0
  5 15  1  0
  5 16  1  0
  2 14  1  6
  1 12  1  0
  1 13  1  0
 11 20  1  0
M  END
Download

3D SDF for NP0217137 ((1r,6s)-6-amino-5-oxocyclohex-2-ene-1-carboxylic acid)


  Mrv1652307102019192D          

 12 12  0  0  1  0            999 V2000
   -1.0723   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0723   -1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3578   -1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3566   -1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3566   -0.2058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3578    0.2066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3578    1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0822    1.4499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3467    1.4383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822    0.2131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822   -1.4499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0743    0.6202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  6  0  0  0
  4 11  2  0  0  0  0
  6 12  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0217137

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H9NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-2,4,6H,3,8H2,(H,10,11)/t4-,6+/m1/s1

> <INCHI_KEY>
AQGCSVBPRRQXIN-XINAWCOVSA-N

> <FORMULA>
C7H9NO3

> <MOLECULAR_WEIGHT>
155.153

> <EXACT_MASS>
155.058243154

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.58513708045384

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,6S)-6-amino-5-oxocyclohex-2-ene-1-carboxylic acid

> <ALOGPS_LOGP>
-2.26

> <JCHEM_LOGP>
-2.735875483571226

> <ALOGPS_LOGS>
-0.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.95968036915022

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5450179256183683

> <JCHEM_PKA_STRONGEST_BASIC>
8.215280262136949

> <JCHEM_POLAR_SURFACE_AREA>
80.38999999999999

> <JCHEM_REFRACTIVITY>
38.5996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.67e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,6S)-6-amino-5-oxocyclohex-2-ene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0217137 ((1r,6s)-6-amino-5-oxocyclohex-2-ene-1-carboxylic acid)

Download
PDB for NP0217137 ((1r,6s)-6-amino-5-oxocyclohex-2-ene-1-carboxylic acid)
HEADER    PROTEIN                                 10-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JUL-20         0                                  
HETATM    1  C   UNK     0      -2.002  -0.384   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.002  -1.924   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.668  -2.694   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.666  -1.924   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.666  -0.384   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.668   0.386   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.668   1.926   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.020   2.706   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.647   2.685   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       2.020   0.398   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       2.020  -2.706   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0      -2.005   1.158   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7   12                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5                                                            
CONECT   11    4                                                            
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0217137 ((1r,6s)-6-amino-5-oxocyclohex-2-ene-1-carboxylic acid)
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SMILES for NP0217137 ((1r,6s)-6-amino-5-oxocyclohex-2-ene-1-carboxylic acid)
[H][C@]1(C=CCC(=O)[C@H]1N)C(O)=O
Download
INCHI for NP0217137 ((1r,6s)-6-amino-5-oxocyclohex-2-ene-1-carboxylic acid)
InChI=1S/C7H9NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-2,4,6H,3,8H2,(H,10,11)/t4-,6+/m1/s1
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View in JSmol
Synonyms
ValueSource
(1R,6S)-6-Amino-5-oxocyclohex-2-ene-1-carboxylateGenerator
Chemical FormulaC7H9NO3
Average Mass155.1530 Da
Monoisotopic Mass155.05824 Da
IUPAC Name(1R,6S)-6-amino-5-oxocyclohex-2-ene-1-carboxylic acid
Traditional Name(1R,6S)-6-amino-5-oxocyclohex-2-ene-1-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H][C@]1(C=CCC(=O)[C@H]1N)C(O)=O
InChI Identifier
InChI=1S/C7H9NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-2,4,6H,3,8H2,(H,10,11)/t4-,6+/m1/s1
InChI KeyAQGCSVBPRRQXIN-XINAWCOVSA-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
Apis ceranaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentBeta amino acids and derivatives  
Alternative Parents
Substituents
  • Beta amino acid or derivatives
    • 

  • Cyclohexenone
    • 

  • Ketone
    • 

  • Cyclic ketone
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organopnictogen compound
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • Primary aliphatic amine
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
  • 6-amino-5-oxocyclohex-2-ene-1-carboxylic acid (CHEBI:60857  )
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-2.3ALOGPS
logP-2.7ChemAxon
logS-0.21ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)8.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.6 m³·mol⁻¹ChemAxon
Polarizability14.59 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 ID26332026  
KEGG Compound IDC19831  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound49852389  
PDB IDNot Available
ChEBI ID60857  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]