NP-MRD: Showing NP-Card for (2s)-2-[(1-hydroxyethylidene)amino]hexanedioic acid (NP0264794)

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Record Information

Version

2.0

Created at

2022-09-08 08:32:36 UTC

Updated at

2022-09-08 08:32:36 UTC

NP-MRD ID

NP0264794

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-[(1-hydroxyethylidene)amino]hexanedioic acid

Description

N-acetyl-L-2-aminoadipic acid, also known as N2-acetyl-L-aminoadipate, belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. N-acetyl-L-2-aminoadipic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2s)-2-[(1-hydroxyethylidene)amino]hexanedioic acid is found in Apis cerana and Trypanosoma brucei. Based on a literature review very few articles have been published on N-acetyl-L-2-aminoadipic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082210322D          

 14 13  0  0  1  0            999 V2000
    3.7125   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -3.5724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -2.8579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4750   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0264794

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H13NO5/c1-5(10)9-6(8(13)14)3-2-4-7(11)12/h6H,2-4H2,1H3,(H,9,10)(H,11,12)(H,13,14)/t6-/m0/s1

> <INCHI_KEY>
FTTGAAZKBNZDCZ-LURJTMIESA-N

> <FORMULA>
C8H13NO5

> <MOLECULAR_WEIGHT>
203.194

> <EXACT_MASS>
203.079372523

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.55577546592042

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-[(1-hydroxyethylidene)amino]hexanedioic acid

> <JCHEM_LOGP>
0.15115737533333315

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.3652478131026955

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.568435247888916

> <JCHEM_PKA_STRONGEST_BASIC>
1.2038030001667295

> <JCHEM_POLAR_SURFACE_AREA>
107.19000000000001

> <JCHEM_REFRACTIVITY>
45.854200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N2-acetyl-L-aminoadipate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       6.930  -9.336   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.160  -8.002   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.620  -8.002   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       6.930  -6.668   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.160  -5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.620  -5.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.850  -4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.310  -4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.930  -4.001   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.160  -2.667   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       8.470  -4.001   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    5   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
N2-Acetyl-L-aminoadipate	ChEBI
N2-Acetyl-L-aminoadipic acid	Generator
N-Acetyl-L-2-aminoadipate	Generator

Chemical Formula

C₈H₁₃NO₅

Average Mass

203.1940 Da

Monoisotopic Mass

203.07937 Da

IUPAC Name

(2S)-2-[(1-hydroxyethylidene)amino]hexanedioic acid

Traditional Name

N2-acetyl-L-aminoadipate

CAS Registry Number

Not Available

SMILES

CC(O)=N[C@@H](CCCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C8H13NO5/c1-5(10)9-6(8(13)14)3-2-4-7(11)12/h6H,2-4H2,1H3,(H,9,10)(H,11,12)(H,13,14)/t6-/m0/s1

InChI Key

FTTGAAZKBNZDCZ-LURJTMIESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Medium-chain fatty acid
Amino fatty acid
Dicarboxylic acid or derivatives
Fatty acid
Fatty acyl
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acyl-L-amino acid (CHEBI:31885 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.15	ChemAxon
pKa (Strongest Acidic)	3.57	ChemAxon
pKa (Strongest Basic)	1.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	107.19 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	45.85 m³·mol⁻¹	ChemAxon
Polarizability	19.56 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

392027

KEGG Compound ID

C12986

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443992

PDB ID

Not Available

ChEBI ID

31885

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-[(1-hydroxyethylidene)amino]hexanedioic acid (NP0264794)

MOL for NP0264794 ((2s)-2-[(1-hydroxyethylidene)amino]hexanedioic acid)

3D MOL for NP0264794 ((2s)-2-[(1-hydroxyethylidene)amino]hexanedioic acid)

3D SDF for NP0264794 ((2s)-2-[(1-hydroxyethylidene)amino]hexanedioic acid)

3D-SDF for NP0264794 ((2s)-2-[(1-hydroxyethylidene)amino]hexanedioic acid)

PDB for NP0264794 ((2s)-2-[(1-hydroxyethylidene)amino]hexanedioic acid)

3D PDB for NP0264794 ((2s)-2-[(1-hydroxyethylidene)amino]hexanedioic acid)

SMILES for NP0264794 ((2s)-2-[(1-hydroxyethylidene)amino]hexanedioic acid)

INCHI for NP0264794 ((2s)-2-[(1-hydroxyethylidene)amino]hexanedioic acid)

Structure for NP0264794 ((2s)-2-[(1-hydroxyethylidene)amino]hexanedioic acid)

3D Structure for NP0264794 ((2s)-2-[(1-hydroxyethylidene)amino]hexanedioic acid)