NP-MRD: Showing NP-Card for 2-O-Caffeoyltartronic acid (NP0084565)

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Record Information

Version

2.0

Created at

2022-04-29 05:16:05 UTC

Updated at

2022-04-29 05:16:05 UTC

NP-MRD ID

NP0084565

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-O-Caffeoyltartronic acid

Description

2-O-Caffeoyltartronic acid belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. 2-O-Caffeoyltartronic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-O-Caffeoyltartronic acid has been detected, but not quantified in, pulses. 2-O-Caffeoyltartronic acid is found in Chondrilla juncea and Vigna radiata . This could make 2-O-caffeoyltartronic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
    1.7213   -1.4420    2.1617 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3892   -0.7023    1.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0215   -0.6077    0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4591    0.1448   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8574    0.2346   -0.4780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2294    1.0564   -1.5372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5509    1.1511   -1.8764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5644    0.4730   -1.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9009    0.5891   -1.5943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1882   -0.3416   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1577   -1.0511    0.5200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8453   -0.4500    0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3919   -0.0158    0.5469 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7470   -0.0881    0.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3117    1.2162    1.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5121    1.3705    1.6123 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4758    2.3229    1.3164 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5509   -0.6770   -0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0200   -1.0443   -1.3450 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9241   -0.8382   -0.1559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7162   -1.1864    1.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2949    0.7140   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5235    1.6309   -2.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8616    1.7881   -2.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1592    1.1816   -2.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9407   -1.6511    1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6456   -1.1069    1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8509   -0.7864    1.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1168    2.6573    0.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3151   -1.6853    0.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14 13  1  0
 13  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 12  2  0
 12 10  1  0
 10 11  1  0
 10  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
 14 18  1  0
 18 20  1  0
 18 19  2  0
  6  5  1  0
 17 29  1  0
 14 28  1  0
  3 21  1  0
  4 22  1  0
 12 27  1  0
 11 26  1  0
  9 25  1  0
  7 24  1  0
  6 23  1  0
 20 30  1  0
M  END


  Mrv0541 05061312122D          

 20 20  0  0  0  0            999 V2000
   -2.8579    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    7.0125    0.0000 C   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
   -3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    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
   -0.7145    2.8875    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
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  4  1  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 16 11  2  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
 20  9  1  0  0  0  0
 20 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084565

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C(OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O8/c13-7-3-1-6(5-8(7)14)2-4-9(15)20-10(11(16)17)12(18)19/h1-5,10,13-14H,(H,16,17)(H,18,19)/b4-2+

> <INCHI_KEY>
URLZWXXTZHVFBD-DUXPYHPUSA-N

> <FORMULA>
C12H10O8

> <MOLECULAR_WEIGHT>
282.203

> <EXACT_MASS>
282.037567296

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
25.259354883767745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanedioic acid

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.3804843456666664

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.6184149728261605

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.161884543460566

> <JCHEM_PKA_STRONGEST_BASIC>
-6.2837637522027885

> <JCHEM_POLAR_SURFACE_AREA>
141.35999999999999

> <JCHEM_REFRACTIVITY>
63.85550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanedioic 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      -5.335  12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  13.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002  12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -9.336  13.090   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -9.336  10.010   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667   3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   7.700   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1    3    6                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    9                                                       
CONECT    5    6    8                                                       
CONECT    6    1    2    5                                                  
CONECT    7    3    8   13                                                  
CONECT    8    5    7   14                                                  
CONECT    9    4   15   20                                                  
CONECT   10   11   12   20                                                  
CONECT   11   10   16   17                                                  
CONECT   12   10   18   19                                                  
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16   11                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   12                                                            
CONECT   20    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
2-O-Caffeoyltartronate	Generator
2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanedioate	Generator

Chemical Formula

C₁₂H₁₀O₈

Average Mass

282.2030 Da

Monoisotopic Mass

282.03757 Da

IUPAC Name

2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanedioic acid

Traditional Name

2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanedioic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C(OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C12H10O8/c13-7-3-1-6(5-8(7)14)2-4-9(15)20-10(11(16)17)12(18)19/h1-5,10,13-14H,(H,16,17)(H,18,19)/b4-2+

InChI Key

URLZWXXTZHVFBD-DUXPYHPUSA-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
Chondrilla juncea	LOTUS Database	35616633
Vigna radiata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Tricarboxylic acid or derivatives
Catechol
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
1-hydroxy-4-unsubstituted benzenoid
Fatty acyl
Benzenoid
1,3-dicarbonyl compound
Monocyclic benzene moiety
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
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	1.87	ALOGPS
logP	1.38	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	2.16	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	141.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	63.86 m³·mol⁻¹	ChemAxon
Polarizability	25.26 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

HMDB0040869

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020699

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

131752962

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-O-Caffeoyltartronic acid (NP0084565)

MOL for NP0084565 (2-O-Caffeoyltartronic acid)

3D MOL for NP0084565 (2-O-Caffeoyltartronic acid)

3D SDF for NP0084565 (2-O-Caffeoyltartronic acid)

3D-SDF for NP0084565 (2-O-Caffeoyltartronic acid)

PDB for NP0084565 (2-O-Caffeoyltartronic acid)

3D PDB for NP0084565 (2-O-Caffeoyltartronic acid)

SMILES for NP0084565 (2-O-Caffeoyltartronic acid)

INCHI for NP0084565 (2-O-Caffeoyltartronic acid)

Structure for NP0084565 (2-O-Caffeoyltartronic acid)

3D Structure for NP0084565 (2-O-Caffeoyltartronic acid)