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Showing NP-Card for 4-formyl-2,3-dihydro-1h-azepine-2,7-dicarboxylic acid (NP0257602)

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Record Information
Version2.0
Created at2022-09-07 22:46:27 UTC
Updated at2022-09-07 22:46:27 UTC
NP-MRD IDNP0257602
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-formyl-2,3-dihydro-1h-azepine-2,7-dicarboxylic acid
Description4-Formyl-2,3-dihydro-1H-azepine-2,7-dicarboxylic acid 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). 4-formyl-2,3-dihydro-1h-azepine-2,7-dicarboxylic acid is found in Amanita muscaria and Hygrocybe conica. 4-Formyl-2,3-dihydro-1H-azepine-2,7-dicarboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0257602 (4-formyl-2,3-dihydro-1h-azepine-2,7-dicarboxylic acid)


  Mrv1533004241515482D          

 15 15  0  0  0  0            999 V2000
    0.1421    2.6007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    2.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5710    2.6007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    1.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5999    1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0703    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    1.0053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8746    0.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4358    0.6221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1178   -0.7710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878    0.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1489    0.6221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
Download

3D MOL for NP0257602 (4-formyl-2,3-dihydro-1h-azepine-2,7-dicarboxylic acid)

     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
   -2.8532    2.6656    0.0154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6335    2.7466    0.2782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7276    1.6435   -0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5434    1.8339    0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013    0.9307    0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5897   -0.3684   -0.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8448   -1.0869   -0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8825   -2.3396   -0.4045 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0236   -0.3627   -0.1195 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4376   -1.1957   -0.1730 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9112   -0.7981    0.1527 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8176   -1.9348   -0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3325   -3.0053   -0.5413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1873   -1.8902    0.1006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3116    0.4291   -0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500    3.6491    0.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7950    2.7873    0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6885    1.3801    0.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7261   -0.5907    0.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783   -2.1826   -0.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9067   -0.5641    1.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6211   -2.6087    0.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8433    0.3342   -1.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4152    0.5279   -0.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 12  1  0
 12 13  2  0
 12 11  1  0
 11 15  1  0
 15  3  1  0
  3  2  1  0
  2  1  2  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 10  1  0
  6  7  1  0
  7  9  1  0
  7  8  2  0
 10 11  1  0
 14 22  1  0
 11 21  1  1
 15 23  1  0
 15 24  1  0
  2 16  1  0
  4 17  1  0
  5 18  1  0
 10 20  1  0
  9 19  1  0
M  END
Download

3D SDF for NP0257602 (4-formyl-2,3-dihydro-1h-azepine-2,7-dicarboxylic acid)


  Mrv1533004241515482D          

 15 15  0  0  0  0            999 V2000
    0.1421    2.6007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    2.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5710    2.6007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    1.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5999    1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0703    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    1.0053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8746    0.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4358    0.6221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1178   -0.7710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878    0.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1489    0.6221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0257602

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1CC(C=O)=CC=C(N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO5/c11-4-5-1-2-6(8(12)13)10-7(3-5)9(14)15/h1-2,4,7,10H,3H2,(H,12,13)(H,14,15)

> <INCHI_KEY>
SRDYVCBFNUJKKW-UHFFFAOYSA-N

> <FORMULA>
C9H9NO5

> <MOLECULAR_WEIGHT>
211.173

> <EXACT_MASS>
211.048072394

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.186719943126814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-formyl-2,3-dihydro-1H-azepine-2,7-dicarboxylic acid

> <ALOGPS_LOGP>
0.42

> <JCHEM_LOGP>
-0.7836159066666666

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.171758680135236

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4166642262599733

> <JCHEM_PKA_STRONGEST_BASIC>
0.6240710065009694

> <JCHEM_POLAR_SURFACE_AREA>
103.70000000000002

> <JCHEM_REFRACTIVITY>
50.85510000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.56e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-formyl-2,3-dihydro-1H-azepine-2,7-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0257602 (4-formyl-2,3-dihydro-1h-azepine-2,7-dicarboxylic acid)

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PDB for NP0257602 (4-formyl-2,3-dihydro-1h-azepine-2,7-dicarboxylic acid)
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       0.265   4.855   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.599   4.085   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.933   4.855   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.599   2.545   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.986   1.876   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.329   0.375   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.369  -0.829   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.829  -0.829   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.131   0.375   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.211   1.876   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -1.633   0.032   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.680   1.161   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.087  -1.439   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.830   0.032   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.878   1.161   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    6   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

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3D PDB for NP0257602 (4-formyl-2,3-dihydro-1h-azepine-2,7-dicarboxylic acid)
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SMILES for NP0257602 (4-formyl-2,3-dihydro-1h-azepine-2,7-dicarboxylic acid)
OC(=O)C1CC(C=O)=CC=C(N1)C(O)=O
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INCHI for NP0257602 (4-formyl-2,3-dihydro-1h-azepine-2,7-dicarboxylic acid)
InChI=1S/C9H9NO5/c11-4-5-1-2-6(8(12)13)10-7(3-5)9(14)15/h1-2,4,7,10H,3H2,(H,12,13)(H,14,15)
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View in JSmol
Synonyms
ValueSource
4-Formyl-2,3-dihydro-1H-azepine-2,7-dicarboxylateGenerator
Chemical FormulaC9H9NO5
Average Mass211.1730 Da
Monoisotopic Mass211.04807 Da
IUPAC Name4-formyl-2,3-dihydro-1H-azepine-2,7-dicarboxylic acid
Traditional Name4-formyl-2,3-dihydro-1H-azepine-2,7-dicarboxylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1CC(C=O)=CC=C(N1)C(O)=O
InChI Identifier
InChI=1S/C9H9NO5/c11-4-5-1-2-6(8(12)13)10-7(3-5)9(14)15/h1-2,4,7,10H,3H2,(H,12,13)(H,14,15)
InChI KeySRDYVCBFNUJKKW-UHFFFAOYSA-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
Amanita muscariaLOTUS Database
Hygrocybe conicaLOTUS 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
    • 

  • Azepine
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Secondary aliphatic amine
    • 

  • Enamine
    • 

  • Organoheterocyclic compound
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organic oxide
    • 

  • Aldehyde
    • 

  • Carbonyl group
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Amine
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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
logP0.42ALOGPS
logP-0.78ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.42ChemAxon
pKa (Strongest Basic)0.62ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.7 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.86 m³·mol⁻¹ChemAxon
Polarizability19.19 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14803859  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]