Showing NP-Card for 2-amino-3-oxoadipic acid (NP0155371)

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Record Information
Version2.0
Created at2022-09-02 12:25:13 UTC
Updated at2022-09-02 12:25:13 UTC
NP-MRD IDNP0155371
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-amino-3-oxoadipic acid
Description2-Amino-3-oxoadipate 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). 2-amino-3-oxoadipic acid is found in Apis cerana. 2-Amino-3-oxoadipate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0155371 (2-amino-3-oxoadipic acid)

  Mrv0541 05091314152D          

 12 11  0  0  0  0            999 V2000
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  2  0  0  0  0
  9  4  2  0  0  0  0
 10  4  1  0  0  0  0
 11  6  2  0  0  0  0
 12  6  1  0  0  0  0
M  END
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3D MOL for NP0155371 (2-amino-3-oxoadipic acid)

     RDKit          3D

 21 20  0  0  0  0  0  0  0  0999 V2000
   -2.8044   -0.8316   -0.4586 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7674   -0.5032    0.5067 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0309    0.8509    1.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3142    1.3994    1.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1045    1.5675    0.5243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4244   -0.5673   -0.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3113   -0.8320   -1.2694 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7802   -0.3145    0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0544   -0.4590   -0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2359   -0.1943    0.7547 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6626   -1.0723    1.5443 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8920    1.0419    0.6952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4656   -0.6160   -1.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6645   -0.2457   -0.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8627   -1.2595    1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0324    1.8595   -0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8286   -1.0617    1.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7357    0.7072    1.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1178   -1.5177   -0.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0787    0.1861   -0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3962    1.8623    1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
  2  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 10 11  2  0
  1 13  1  0
  1 14  1  0
  2 15  1  1
  5 16  1  0
  8 17  1  0
  8 18  1  0
  9 19  1  0
  9 20  1  0
 12 21  1  0
M  END
Download

3D SDF for NP0155371 (2-amino-3-oxoadipic acid)

  Mrv0541 05091314152D          

 12 11  0  0  0  0            999 V2000
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  2  0  0  0  0
  9  4  2  0  0  0  0
 10  4  1  0  0  0  0
 11  6  2  0  0  0  0
 12  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0155371

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(C(O)=O)C(=O)CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H9NO5/c7-5(6(11)12)3(8)1-2-4(9)10/h5H,1-2,7H2,(H,9,10)(H,11,12)

> <INCHI_KEY>
HXWZRYKURKEOSO-UHFFFAOYSA-N

> <FORMULA>
C6H9NO5

> <MOLECULAR_WEIGHT>
175.1394

> <EXACT_MASS>
175.048072403

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
15.249955814161092

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-oxohexanedioic acid

> <ALOGPS_LOGP>
-3.24

> <JCHEM_LOGP>
-3.2964771232012993

> <ALOGPS_LOGS>
-1.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.0377694308078915

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5755246751057292

> <JCHEM_PKA_STRONGEST_BASIC>
7.240802299274756

> <JCHEM_POLAR_SURFACE_AREA>
117.69000000000001

> <JCHEM_REFRACTIVITY>
36.42790000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-oxoadipic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0155371 (2-amino-3-oxoadipic acid)

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PDB for NP0155371 (2-amino-3-oxoadipic acid)
HEADER    PROTEIN                                 09-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-MAY-13         0                                  
HETATM    1  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       8.621   4.977   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       7.287   1.127   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.953   2.667   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.286   4.977   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5    8                                                  
CONECT    4    2    9   10                                                  
CONECT    5    3    6    7                                                  
CONECT    6    5   11   12                                                  
CONECT    7    5                                                            
CONECT    8    3                                                            
CONECT    9    4                                                            
CONECT   10    4                                                            
CONECT   11    6                                                            
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0155371 (2-amino-3-oxoadipic acid)
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SMILES for NP0155371 (2-amino-3-oxoadipic acid)
NC(C(O)=O)C(=O)CCC(O)=O
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INCHI for NP0155371 (2-amino-3-oxoadipic acid)
InChI=1S/C6H9NO5/c7-5(6(11)12)3(8)1-2-4(9)10/h5H,1-2,7H2,(H,9,10)(H,11,12)
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View in JSmol
Synonyms
ValueSource
2-Amino-3-oxo-hexanedioic acidChEBI
2-Amino-3-oxohexanedioic acidChEBI
2-Amino-3-oxo-hexanedioateGenerator
2-Amino-3-oxohexanedioateGenerator
2-Amino-3-oxoadipic acidGenerator
2-amino-3-OxoadipateChEBI
Chemical FormulaC6H9NO5
Average Mass175.1394 Da
Monoisotopic Mass175.04807 Da
IUPAC Name2-amino-3-oxohexanedioic acid
Traditional Name2-amino-3-oxoadipic acid
CAS Registry NumberNot Available
SMILES
NC(C(O)=O)C(=O)CCC(O)=O
InChI Identifier
InChI=1S/C6H9NO5/c7-5(6(11)12)3(8)1-2-4(9)10/h5H,1-2,7H2,(H,9,10)(H,11,12)
InChI KeyHXWZRYKURKEOSO-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
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 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
    • 

  • Medium-chain keto acid
    • 

  • Gamma-keto acid
    • 

  • Amino fatty acid
    • 

  • Beta-keto acid
    • 

  • Beta-hydroxy ketone
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Keto acid
    • 

  • 1,3-dicarbonyl compound
    • 

  • Fatty acyl
    • 

  • Alpha-aminoketone
    • 

  • Amino acid
    • 

  • Ketone
    • 

  • Carboxylic acid
    • 

  • Organonitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organic oxide
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Organopnictogen compound
    • 

  • Organooxygen compound
    • 

  • Primary amine
    • 

  • Amine
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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-3.2ALOGPS
logP-3.3ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)1.58ChemAxon
pKa (Strongest Basic)7.24ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity36.43 m³·mol⁻¹ChemAxon
Polarizability15.25 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0060273  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05520  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440714  
PDB IDNot Available
ChEBI ID28095  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]