NP-MRD: Showing NP-Card for (2s,4z)-4-{2-[(carboxymethyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid (NP0272614)

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Record Information

Version

2.0

Created at

2022-09-08 19:17:44 UTC

Updated at

2022-09-08 19:17:44 UTC

NP-MRD ID

NP0272614

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,4z)-4-{2-[(carboxymethyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid

Description

Portulacaxanthin III belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. (2s,4z)-4-{2-[(carboxymethyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid is found in Portulaca grandiflora. (2s,4z)-4-{2-[(carboxymethyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid was first documented in 2020 (PMID: 32666336). Based on a literature review very few articles have been published on Portulacaxanthin III.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
    3.7097    0.8339    1.4336 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0906    1.2602    0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5556    2.5577    0.1747 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407    0.3680   -0.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5194   -0.9317   -0.5010 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519   -1.1286   -0.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2931   -0.0462   -0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0090   -0.2021   -0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5287   -1.5028    0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6669   -1.4893    0.7515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2362   -2.7557    1.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6829   -3.8507    0.8725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4281   -2.7918    1.8775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3000   -0.2514    1.0756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1739    0.8852    0.2129 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3282    0.8765   -0.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2028   -0.0276   -0.7043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4779    1.8672   -1.7122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8821    0.9740   -0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9445    3.3363   -0.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0776    0.1996   -1.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4772    0.8288   -1.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9423   -2.1137   -0.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6647    0.9345   -0.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0044   -2.3821   -0.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3398   -2.7371    2.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8479   -0.2405    1.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2878    1.8257    0.8014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8315    2.7812   -1.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0601    1.0347   -1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3060    1.8880   -0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8 19  1  0
 19 15  1  0
 15 14  1  0
 14 10  1  0
 10  9  2  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
 15 16  1  0
 16 18  1  0
 16 17  2  0
  9  8  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
 19 30  1  0
 19 31  1  0
 15 28  1  1
 14 27  1  0
  9 25  1  0
 13 26  1  0
 18 29  1  0
M  END


  Mrv1652309082221172D          

 19 19  0  0  1  0            999 V2000
    2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
  8 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0272614

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2O6/c14-9(15)5-12-2-1-6-3-7(10(16)17)13-8(4-6)11(18)19/h1-3,8,13H,4-5H2,(H,14,15)(H,16,17)(H,18,19)/b6-1+,12-2?/t8-/m0/s1

> <INCHI_KEY>
ZZZQMKRQWYRKFG-SDYYGWODSA-N

> <FORMULA>
C11H12N2O6

> <MOLECULAR_WEIGHT>
268.225

> <EXACT_MASS>
268.069536114

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
25.459039433235578

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-3.987645979694391

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.4043758776459603

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.564733035529665

> <JCHEM_PKA_STRONGEST_BASIC>
9.039636370932119

> <JCHEM_POLAR_SURFACE_AREA>
136.29

> <JCHEM_REFRACTIVITY>
63.81840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

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

> <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  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.667   6.160   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   15    8                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₂N₂O₆

Average Mass

268.2250 Da

Monoisotopic Mass

268.06954 Da

IUPAC Name

(2S,4Z)-4-{2-[(carboxymethyl)imino]ethylidene}-1,2,3,4-tetrahydropyridine-2,6-dicarboxylic acid

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC(=O)CN=C\C=C1\C[C@H](NC(=C1)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C11H12N2O6/c14-9(15)5-12-2-1-6-3-7(10(16)17)13-8(4-6)11(18)19/h1-3,8,13H,4-5H2,(H,14,15)(H,16,17)(H,18,19)/b6-1+,12-2?/t8-/m0/s1

InChI Key

ZZZQMKRQWYRKFG-SDYYGWODSA-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
Portulaca grandiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are 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

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Tricarboxylic acid or derivatives
Tetrahydropyridine
Hydropyridine
Amino acid
Shiff base
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Enamine
Secondary aliphatic amine
Carboxylic acid
Aldimine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
Amine
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	-4	ChemAxon
pKa (Strongest Acidic)	1.56	ChemAxon
pKa (Strongest Basic)	9.04	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	5	ChemAxon
Refractivity	63.82 m³·mol⁻¹	ChemAxon
Polarizability	25.46 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

C00001605

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

135809744

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mosquera N, Cejudo-Bastante MJ, Heredia FJ, Hurtado N: Identification of New Betalains in Separated Betacyanin and Betaxanthin Fractions from Ulluco (Ullucus tuberosus Caldas) by HPLC-DAD-ESI-MS. Plant Foods Hum Nutr. 2020 Sep;75(3):434-440. doi: 10.1007/s11130-020-00837-9. [PubMed:32666336 ]
LOTUS database [Link]

Showing NP-Card for (2s,4z)-4-{2-[(carboxymethyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid (NP0272614)

MOL for NP0272614 ((2s,4z)-4-{2-[(carboxymethyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid)

3D MOL for NP0272614 ((2s,4z)-4-{2-[(carboxymethyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid)

3D SDF for NP0272614 ((2s,4z)-4-{2-[(carboxymethyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid)

3D-SDF for NP0272614 ((2s,4z)-4-{2-[(carboxymethyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid)

PDB for NP0272614 ((2s,4z)-4-{2-[(carboxymethyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid)

3D PDB for NP0272614 ((2s,4z)-4-{2-[(carboxymethyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid)

SMILES for NP0272614 ((2s,4z)-4-{2-[(carboxymethyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid)

INCHI for NP0272614 ((2s,4z)-4-{2-[(carboxymethyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid)

Structure for NP0272614 ((2s,4z)-4-{2-[(carboxymethyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid)

3D Structure for NP0272614 ((2s,4z)-4-{2-[(carboxymethyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid)