NP-MRD: Showing NP-Card for (2s)-2-{[(2e)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioic acid (NP0201672)

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Record Information

Version

2.0

Created at

2022-09-04 20:45:32 UTC

Updated at

2022-09-04 20:45:33 UTC

NP-MRD ID

NP0201672

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2e)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioic acid

Description

UNII-AJE3N72YTX belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. (2s)-2-{[(2e)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioic acid is found in Theobroma cacao. Based on a literature review very few articles have been published on UNII-AJE3N72YTX.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
   -5.6686    0.3318   -1.0084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1846   -0.6031   -0.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0756   -1.5855    0.1716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7519   -0.7312   -0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8888    0.4056   -0.4976 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5350    0.0812   -0.1750 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0065   -0.7290    0.6044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6100   -1.6342    1.4648 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4839   -0.7569    0.6436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1585    0.0619   -0.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6071    0.0760   -0.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2331    0.9806   -1.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5928    1.0430   -1.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3845    0.2342   -0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7801    0.3210   -0.3440 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7504   -0.6495    0.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3713   -0.7251    0.6394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2678    1.7186    0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3556    2.2593   -0.0938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3390    2.3551    0.9027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3319   -1.5453    1.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3915   -1.7057   -0.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6872   -0.8454    1.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9776    0.5091   -1.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3593   -1.7344    2.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0089   -1.4172    1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6076    0.7515   -0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150    1.6329   -1.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0813    1.7412   -1.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2429   -0.2812   -1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4023   -1.2791    1.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9451   -1.4416    1.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8338    3.1615    0.5901 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  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  5 18  1  0
 18 20  1  0
 18 19  2  0
 17 11  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  6
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 20 33  1  0
M  END


  Mrv1652309042222452D          

 20 20  0  0  1  0            999 V2000
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  7  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0201672

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H13NO6/c15-9-4-1-8(2-5-9)3-6-11(16)14-10(13(19)20)7-12(17)18/h1-6,10,15H,7H2,(H,14,16)(H,17,18)(H,19,20)/b6-3+/t10-/m0/s1

> <INCHI_KEY>
FKBRNPNAUOXZMQ-YVGDHZEHSA-N

> <FORMULA>
C13H13NO6

> <MOLECULAR_WEIGHT>
279.248

> <EXACT_MASS>
279.074287143

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.078581074963388

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-{[(2E)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioic acid

> <JCHEM_LOGP>
1.473794158

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.141850107441601

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5143560644938674

> <JCHEM_PKA_STRONGEST_BASIC>
1.0595508997135812

> <JCHEM_POLAR_SURFACE_AREA>
127.42

> <JCHEM_REFRACTIVITY>
68.89529999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2E)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.334  -5.390   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667  -9.240   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   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   11                                                       
CONECT   18    5   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₃NO₆

Average Mass

279.2480 Da

Monoisotopic Mass

279.07429 Da

IUPAC Name

(2S)-2-{[(2E)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioic acid

Traditional Name

(2S)-2-{[(2E)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C[C@H](N=C(O)\C=C\C1=CC=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C13H13NO6/c15-9-4-1-8(2-5-9)3-6-11(16)14-10(13(19)20)7-12(17)18/h1-6,10,15H,7H2,(H,14,16)(H,17,18)(H,19,20)/b6-3+/t10-/m0/s1

InChI Key

FKBRNPNAUOXZMQ-YVGDHZEHSA-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
Theobroma cacao	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic 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

Aspartic acid and derivatives

Alternative Parents

Substituents

Aspartic acid or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.47	ChemAxon
pKa (Strongest Acidic)	3.51	ChemAxon
pKa (Strongest Basic)	1.06	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	127.42 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	68.9 m³·mol⁻¹	ChemAxon
Polarizability	27.08 Å³	ChemAxon
Number of Rings	1	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

34989178

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68537088

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2e)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioic acid (NP0201672)

MOL for NP0201672 ((2s)-2-{[(2e)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioic acid)

3D MOL for NP0201672 ((2s)-2-{[(2e)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioic acid)

3D SDF for NP0201672 ((2s)-2-{[(2e)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioic acid)

3D-SDF for NP0201672 ((2s)-2-{[(2e)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioic acid)

PDB for NP0201672 ((2s)-2-{[(2e)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioic acid)

3D PDB for NP0201672 ((2s)-2-{[(2e)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioic acid)

SMILES for NP0201672 ((2s)-2-{[(2e)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioic acid)

INCHI for NP0201672 ((2s)-2-{[(2e)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioic acid)

Structure for NP0201672 ((2s)-2-{[(2e)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioic acid)

3D Structure for NP0201672 ((2s)-2-{[(2e)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}butanedioic acid)