NP-MRD: Showing NP-Card for gamma-Aminobutyric acid-betaxanthin (NP0050171)

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Record Information

Version

2.0

Created at

2022-03-17 21:24:26 UTC

Updated at

2022-03-17 21:24:26 UTC

NP-MRD ID

NP0050171

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gamma-Aminobutyric acid-betaxanthin

Description

(2S,4E)-4-[(2Z)-2-[(3-carboxypropyl)imino]ethylidene]-1,2,3,4-tetrahydropyridine-2,6-dicarboxylic acid belongs to the class of organic compounds known as gamma amino acids and derivatives. gamma-Aminobutyric acid-betaxanthin is found in Beta vulgaris. These are amino acids having a (-NH2) group attached to the gamma carbon atom (2S,4E)-4-[(2Z)-2-[(3-carboxypropyl)imino]ethylidene]-1,2,3,4-tetrahydropyridine-2,6-dicarboxylic acid is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304022019553D          

 21 21  0  0  0  0            999 V2000
    4.0883    0.9143   -0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500   -0.4602   -0.8408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0398    0.3517    0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6314    0.7931   -0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6128    0.1484   -1.1213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8911    0.4089    1.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2008   -0.2585   -0.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3161    0.1751    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1863    0.6156    1.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5626    0.4222   -0.7051 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9677   -0.3817   -1.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7715    0.8534    3.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5011   -0.4737   -1.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9092    0.3604   -1.2088 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0063    0.6059    0.6400 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3177    0.1010   -2.3040 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9619   -0.8365   -0.3288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9848    1.0491    3.2977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8889    0.8452    4.2054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4966   -0.9237   -0.8058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3022   -0.8213   -2.7226 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  1  0  0  0  0
  2 11  1  0  0  0  0
  3  5  1  0  0  0  0
  3  8  2  0  0  0  0
  4 14  1  0  0  0  0
  5 14  2  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  9 12  1  0  0  0  0
  9 15  1  0  0  0  0
 10 13  1  6  0  0  0
 10 15  1  0  0  0  0
 11 16  2  0  0  0  0
 11 17  1  0  0  0  0
 12 18  2  0  0  0  0
 12 19  1  0  0  0  0
 13 20  2  0  0  0  0
 13 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050171

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CCC\N=C/C=C1\C[C@H](NC(=C1)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O6/c16-11(17)2-1-4-14-5-3-8-6-9(12(18)19)15-10(7-8)13(20)21/h3,5-6,10,15H,1-2,4,7H2,(H,16,17)(H,18,19)(H,20,21)/b8-3-,14-5-/t10-/m0/s1

> <INCHI_KEY>
ICGRVJRPJJYWPZ-FDLAANOMSA-N

> <FORMULA>
C13H16N2O6

> <MOLECULAR_WEIGHT>
296.279

> <EXACT_MASS>
296.100836243

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.62389488760626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4E)-4-[(2Z)-2-[(3-carboxypropyl)imino]ethylidene]-1,2,3,4-tetrahydropyridine-2,6-dicarboxylic acid

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
-3.6939148446629715

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.064153402590398

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.479978534177692

> <JCHEM_PKA_STRONGEST_BASIC>
10.344695455497568

> <JCHEM_POLAR_SURFACE_AREA>
136.29

> <JCHEM_REFRACTIVITY>
73.2728

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4E)-4-[(2Z)-2-[(3-carboxypropyl)imino]ethylidene]-2,3-dihydro-1H-pyridine-2,6-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  C   UNK     0       4.088   0.914  -0.390  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.550  -0.460  -0.841  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.040   0.352   0.129  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.631   0.793  -0.034  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.613   0.148  -1.121  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.891   0.409   1.644  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.201  -0.259  -0.761  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.316   0.175   0.325  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.186   0.616   1.797  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.563   0.422  -0.705  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.968  -0.382  -1.198  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.772   0.853   3.138  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.501  -0.474  -1.414  0.00  0.00           C+0
HETATM   14  N   UNK     0       1.909   0.360  -1.209  0.00  0.00           N+0
HETATM   15  N   UNK     0      -4.006   0.606   0.640  0.00  0.00           N+0
HETATM   16  O   UNK     0       6.318   0.101  -2.304  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.962  -0.837  -0.329  0.00  0.00           O+0
HETATM   18  O   UNK     0      -4.985   1.049   3.298  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.889   0.845   4.205  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.497  -0.924  -0.806  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.302  -0.821  -2.723  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1   11                                                       
CONECT    3    5    8                                                       
CONECT    4    1   14                                                       
CONECT    5    3   14                                                       
CONECT    6    8    9                                                       
CONECT    7    8   10                                                       
CONECT    8    3    6    7                                                  
CONECT    9    6   12   15                                                  
CONECT   10    7   13   15                                                  
CONECT   11    2   16   17                                                  
CONECT   12    9   18   19                                                  
CONECT   13   10   20   21                                                  
CONECT   14    4    5                                                       
CONECT   15    9   10                                                       
CONECT   16   11                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   13                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
(2S,4E)-4-[(2Z)-2-[(3-Carboxypropyl)imino]ethylidene]-1,2,3,4-tetrahydropyridine-2,6-dicarboxylate	Generator

Chemical Formula

C₁₃H₁₆N₂O₆

Average Mass

296.2790 Da

Monoisotopic Mass

296.10084 Da

IUPAC Name

(2S,4E)-4-[(2Z)-2-[(3-carboxypropyl)imino]ethylidene]-1,2,3,4-tetrahydropyridine-2,6-dicarboxylic acid

Traditional Name

(2S,4E)-4-[(2Z)-2-[(3-carboxypropyl)imino]ethylidene]-2,3-dihydro-1H-pyridine-2,6-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CCC\N=C/C=C1\C[C@H](NC(=C1)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C13H16N2O6/c16-11(17)2-1-4-14-5-3-8-6-9(12(18)19)15-10(7-8)13(20)21/h3,5-6,10,15H,1-2,4,7H2,(H,16,17)(H,18,19)(H,20,21)/b8-3-,14-5-/t10-/m0/s1

InChI Key

ICGRVJRPJJYWPZ-FDLAANOMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Beta vulgaris	LOTUS Database	35616633
Beta vulgaris ssp. cicla	FooDB	PHYTOHUB
Opuntia	FooDB	PHYTOHUB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma 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

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Tricarboxylic acid or derivatives
Tetrahydropyridine
Hydropyridine
Amino acid
Shiff base
Aldimine
Carboxylic acid
Secondary aliphatic amine
Enamine
Secondary amine
Azacycle
Organoheterocyclic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic oxide
Organopnictogen compound
Imine
Organonitrogen compound
Organooxygen compound
Amine
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	0.78	ALOGPS
logP	-3.7	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.48	ChemAxon
pKa (Strongest Basic)	10.34	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	136.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	73.27 m³·mol⁻¹	ChemAxon
Polarizability	29.62 Å³	ChemAxon
Number of Rings	1	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for gamma-Aminobutyric acid-betaxanthin (NP0050171)

MOL for NP0050171 (gamma-Aminobutyric acid-betaxanthin)

3D MOL for NP0050171 (gamma-Aminobutyric acid-betaxanthin)

3D SDF for NP0050171 (gamma-Aminobutyric acid-betaxanthin)

3D-SDF for NP0050171 (gamma-Aminobutyric acid-betaxanthin)

PDB for NP0050171 (gamma-Aminobutyric acid-betaxanthin)

3D PDB for NP0050171 (gamma-Aminobutyric acid-betaxanthin)

SMILES for NP0050171 (gamma-Aminobutyric acid-betaxanthin)

INCHI for NP0050171 (gamma-Aminobutyric acid-betaxanthin)

Structure for NP0050171 (gamma-Aminobutyric acid-betaxanthin)

3D Structure for NP0050171 (gamma-Aminobutyric acid-betaxanthin)