NP-MRD: Showing NP-Card for 2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic acid (NP0261029)

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Record Information

Version

2.0

Created at

2022-09-08 03:22:19 UTC

Updated at

2022-09-08 03:22:19 UTC

NP-MRD ID

NP0261029

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic acid

Description

Caffeoyltartronic acid belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. 2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic acid is found in Vigna radiata. 2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic acid was first documented in 2004 (PMID: 15089035). Based on a literature review very few articles have been published on caffeoyltartronic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.3866    1.2797    1.4485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4236    0.9898    0.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4146    1.8995    0.4794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3564   -0.3483    0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4690   -1.0674    0.4621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3466   -0.2198   -1.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4619    0.3816   -2.0535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3794   -0.7984   -2.1073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1238   -0.9870    0.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2519   -2.0334    1.2729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7890   -0.4500    0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2936   -1.0416    0.8244 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6457   -0.5500    0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7027   -1.2462    1.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0043   -0.8315    0.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3079    0.3201    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6278    0.7042    0.1030 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2668    1.0169   -0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5062    2.1726   -1.0295 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9515    0.5771   -0.1060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513    2.7358   -0.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2290   -1.9656    0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3507   -0.7643   -1.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6472    0.4502   -0.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1182   -1.9551    1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4806   -2.1525    1.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8523   -1.3581    1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9264    1.5173   -0.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4058    2.5588   -1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1910    1.1656   -0.5527 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
  4  6  1  0
  6  8  1  0
  6  7  2  0
  4  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 20 13  1  0
  3 21  1  0
  5 22  1  0
  8 23  1  0
 11 24  1  0
 12 25  1  0
 14 26  1  0
 15 27  1  0
 17 28  1  0
 19 29  1  0
 20 30  1  0
M  END


  Mrv1652309082205222D          

 20 20  0  0  0  0            999 V2000
   -1.4289    4.9500    0.0000 O   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
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    2.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.1414    0.0000 O   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
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
    0.7145   -0.4125    0.0000 C   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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 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
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 13 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0261029

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
YVUYIEJFBANVBK-DUXPYHPUSA-N

> <FORMULA>
C12H10O8

> <MOLECULAR_WEIGHT>
282.204

> <EXACT_MASS>
282.037567282

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
24.520866429275003

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic acid

> <JCHEM_LOGP>
0.8939707996666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.368745686711575

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0665293836718917

> <JCHEM_PKA_STRONGEST_BASIC>
-5.670173102185129

> <JCHEM_POLAR_SURFACE_AREA>
152.35999999999999

> <JCHEM_REFRACTIVITY>
64.45460000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic 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      -2.667   9.240   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.104   5.596   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.564   8.264   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.976   8.264   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.334   9.597   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -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       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   20  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    6    9                                             
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
Caffeoyltartronate	Generator

Chemical Formula

C₁₂H₁₀O₈

Average Mass

282.2040 Da

Monoisotopic Mass

282.03757 Da

IUPAC Name

2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic acid

Traditional Name

2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

YVUYIEJFBANVBK-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, 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
Vigna radiata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids and derivatives

Alternative Parents

Substituents

Hydroxycinnamic acid or derivatives
Medium-chain keto acid
Styrene
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
B'-hydroxy-alpha,beta-unsaturated-ketone
Phenol
Hydroxy fatty acid
Branched fatty acid
Beta-keto acid
Fatty acyl
Benzenoid
Unsaturated fatty acid
Keto acid
Hydroxy acid
Dicarboxylic acid or derivatives
Beta-hydroxy ketone
Monocyclic benzene moiety
Alpha-hydroxy acid
Acyloin
Alpha,beta-unsaturated ketone
Tertiary alcohol
Enone
Alpha-hydroxy ketone
Acryloyl-group
Ketone
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	0.89	ChemAxon
pKa (Strongest Acidic)	2.07	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	152.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	64.45 m³·mol⁻¹	ChemAxon
Polarizability	24.52 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

C00054038

Chemspider ID

65792640

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129660911

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Saleem M, Kim HJ, Jin C, Lee YS: Antioxidant caffeic acid derivatives from leaves of Parthenocissus tricuspidata. Arch Pharm Res. 2004 Mar;27(3):300-4. doi: 10.1007/BF02980064. [PubMed:15089035 ]
LOTUS database [Link]

Showing NP-Card for 2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic acid (NP0261029)

MOL for NP0261029 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic acid)

3D MOL for NP0261029 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic acid)

3D SDF for NP0261029 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic acid)

3D-SDF for NP0261029 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic acid)

PDB for NP0261029 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic acid)

3D PDB for NP0261029 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic acid)

SMILES for NP0261029 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic acid)

INCHI for NP0261029 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic acid)

Structure for NP0261029 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic acid)

3D Structure for NP0261029 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2-hydroxypropanedioic acid)