NP-MRD: Showing NP-Card for N-(4-Amino-1-carboxybutyl)glutamic acid (NP0084838)

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Record Information

Version

2.0

Created at

2022-04-29 05:28:14 UTC

Updated at

2022-04-29 05:28:15 UTC

NP-MRD ID

NP0084838

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-(4-Amino-1-carboxybutyl)glutamic acid

Description

Nopalinic acid, also known as nopalinate or ornaline, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Nopalinic acid is a very strong basic compound (based on its pKa). Outside of the human body, Nopalinic acid has been detected, but not quantified in, fats and oils. This could make nopalinic acid a potential biomarker for the consumption of these foods. N-(4-Amino-1-carboxybutyl)glutamic acid is found in Apis cerana and Helianthus annuus . N-(4-Amino-1-carboxybutyl)glutamic acid was first documented in 1978 (PMID: 16660462). A glutamic acid derivative in which one of the amino hydrogens of glutamic acid has been replaced by a 4-amino-1-carboxybutyl group (PMID: 16660518) (PMID: 476084).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 35  0  0  0  0  0  0  0  0999 V2000
    4.6056    1.1309   -0.9001 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1495    1.0991   -0.8339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6877   -0.1570   -0.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1516   -0.1261   -0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5990   -1.2844    0.6523 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7917   -1.3237    0.6978 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5726   -0.3651    1.3259 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7637    0.0154    0.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4781    0.6024   -0.8569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7700    0.8464   -1.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3622   -0.1711   -2.0357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3859    2.0623   -1.6907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9790    0.7291    2.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0883    0.6599    2.7354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5696    2.0065    2.1296 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1994   -2.6003    0.2842 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3446   -3.5538    0.0064 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4932   -2.9543    0.1974 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8820    2.1391   -0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9247    0.6130   -1.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8311    1.9596   -0.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486    1.1415   -1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0354   -1.0024   -0.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0834   -0.2371    0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8573    0.8600    0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9011   -0.1535   -1.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792   -1.1342    1.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2622   -1.8771   -0.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236   -0.9908    2.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3511   -0.9431    0.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4464    0.6324    1.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8630    1.5312   -0.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9065   -0.1074   -1.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2691    2.1805   -2.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4296    2.6223    1.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8624   -3.8503    0.5313 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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 10 11  2  0
  7 13  1  0
 13 15  1  0
 13 14  2  0
  5 16  1  0
 16 18  1  0
 16 17  2  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  1
  6 28  1  0
  7 29  1  1
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 12 34  1  0
 15 35  1  0
 18 36  1  0
M  END


  Mrv0541 05061304462D          

 18 17  0  0  0  0            999 V2000
    6.0473    0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0473   -0.1914    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
    3.1895   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618    1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -0.6039    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
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618    1.8711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -0.6039    0.0000 O   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
    4.6184    0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 16  9  1  0  0  0  0
 17 10  2  0  0  0  0
 18 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084838

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H18N2O6/c11-5-1-2-6(9(15)16)12-7(10(17)18)3-4-8(13)14/h6-7,12H,1-5,11H2,(H,13,14)(H,15,16)(H,17,18)

> <INCHI_KEY>
UXZAXFPFSQRZOZ-UHFFFAOYSA-N

> <FORMULA>
C10H18N2O6

> <MOLECULAR_WEIGHT>
262.2597

> <EXACT_MASS>
262.116486318

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
25.459325752250876

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4-amino-1-carboxybutyl)amino]pentanedioic acid

> <ALOGPS_LOGP>
-3.25

> <JCHEM_LOGP>
-6.1543292786205654

> <ALOGPS_LOGS>
-1.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.1915041763285137

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.582275579961246

> <JCHEM_PKA_STRONGEST_BASIC>
10.236679663561041

> <JCHEM_POLAR_SURFACE_AREA>
149.95

> <JCHEM_REFRACTIVITY>
59.352000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(4-amino-1-carboxybutyl)amino]pentanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      11.288   1.183   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.288  -0.357   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       5.954  -3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.622   1.953   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.955  -1.127   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.621  -3.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.621  -0.357   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.621  -4.977   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      12.622   3.493   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       9.955  -2.667   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       3.286  -3.437   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.620  -1.127   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       7.287  -1.127   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.621   1.183   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.287  -5.747   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.955  -5.747   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    6                                                       
CONECT    3    4    7                                                       
CONECT    4    3    8                                                       
CONECT    5    1   11                                                       
CONECT    6    2    9   12                                                  
CONECT    7    3   10   12                                                  
CONECT    8    4   13   14                                                  
CONECT    9    6   15   16                                                  
CONECT   10    7   17   18                                                  
CONECT   11    5                                                            
CONECT   12    6    7                                                       
CONECT   13    8                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   10                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
N2-(1,3-Dicarboxypropyl)ornithine	ChEBI
Nopalinate	Generator
N-(4-Amino-1-carboxybutyl)glutamic acid, 9ci	HMDB
Ornaline	HMDB
Nopalinic acid	ChEBI

Chemical Formula

C₁₀H₁₈N₂O₆

Average Mass

262.2597 Da

Monoisotopic Mass

262.11649 Da

IUPAC Name

2-[(4-amino-1-carboxybutyl)amino]pentanedioic acid

Traditional Name

2-[(4-amino-1-carboxybutyl)amino]pentanedioic acid

CAS Registry Number

Not Available

SMILES

NCCCC(NC(CCC(O)=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C10H18N2O6/c11-5-1-2-6(9(15)16)12-7(10(17)18)3-4-8(13)14/h6-7,12H,1-5,11H2,(H,13,14)(H,15,16)(H,17,18)

InChI Key

UXZAXFPFSQRZOZ-UHFFFAOYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Helianthus annuus L.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
Alpha-amino acid
Tricarboxylic acid or derivatives
Amino fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Secondary aliphatic amine
Secondary amine
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	-3.2	ALOGPS
logP	-6.2	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	2.58	ChemAxon
pKa (Strongest Basic)	10.24	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	149.95 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	59.35 m³·mol⁻¹	ChemAxon
Polarizability	25.46 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029437

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000542

KNApSAcK ID

Not Available

Chemspider ID

3672801

KEGG Compound ID

C01683

BioCyc ID

CPD-15816

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4474580

PDB ID

Not Available

ChEBI ID

133921

Good Scents ID

Not Available

References

General References

Kemp JD: In Vivo Synthesis of Crown Gall-specific Agrobacterium tumefaciens-directed Derivatives of Basic Amino Acids. Plant Physiol. 1978 Jul;62(1):26-30. doi: 10.1104/pp.62.1.26. [PubMed:16660462 ]
Sutton DW, Kemp JD, Hack E: Characterization of the enzyme responsible for nopaline and ornaline synthesis in sunflower crown gall tissues. Plant Physiol. 1978 Sep;62(3):363-7. doi: 10.1104/pp.62.3.363. [PubMed:16660518 ]
Kemp JD, Sutton DW, Hack E: Purification and characterization of the crown gall specific enzyme nopaline synthase. Biochemistry. 1979 Aug 21;18(17):3755-60. doi: 10.1021/bi00584a017. [PubMed:476084 ]

Showing NP-Card for N-(4-Amino-1-carboxybutyl)glutamic acid (NP0084838)

MOL for NP0084838 (N-(4-Amino-1-carboxybutyl)glutamic acid)

3D MOL for NP0084838 (N-(4-Amino-1-carboxybutyl)glutamic acid)

3D SDF for NP0084838 (N-(4-Amino-1-carboxybutyl)glutamic acid)

3D-SDF for NP0084838 (N-(4-Amino-1-carboxybutyl)glutamic acid)

PDB for NP0084838 (N-(4-Amino-1-carboxybutyl)glutamic acid)

3D PDB for NP0084838 (N-(4-Amino-1-carboxybutyl)glutamic acid)

SMILES for NP0084838 (N-(4-Amino-1-carboxybutyl)glutamic acid)

INCHI for NP0084838 (N-(4-Amino-1-carboxybutyl)glutamic acid)

Structure for NP0084838 (N-(4-Amino-1-carboxybutyl)glutamic acid)

3D Structure for NP0084838 (N-(4-Amino-1-carboxybutyl)glutamic acid)