NP-MRD: Showing NP-Card for (2s,3r)-trans-caftaric acid (NP0238577)

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Record Information

Version

2.0

Created at

2022-09-06 21:59:49 UTC

Updated at

2022-09-06 21:59:49 UTC

NP-MRD ID

NP0238577

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r)-trans-caftaric acid

Description

(2S,3R)-trans-caftaric acid, also known as trans-caftarate or (2S,3R)-trans-caffeoyl tartarate, 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 (2S,3R)-trans-caftaric acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2s,3r)-trans-caftaric acid is found in Vitis aestivalis and Vitis vinifera. Based on a literature review very few articles have been published on (2S,3R)-trans-caftaric acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
   -1.7559    1.4675   -1.9536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1655    0.9446   -0.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2601    0.6757   -1.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9689    0.1289   -0.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4074   -0.1581   -0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814    0.1145   -1.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5286   -0.1644   -1.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1253   -0.7367   -0.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4775   -1.0381   -0.2810 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3905   -1.0329    0.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0209   -1.6200    1.9540 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0457   -0.7429    0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8610    0.6381    0.1517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2330    0.9081    0.2371 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5198    1.7862    1.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5814    2.1689    2.1243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8184    2.1816    1.6702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0454   -0.3560    0.4248 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3836    0.0299    0.4962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8674   -1.2797   -0.7191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8390   -1.5969   -1.4441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6357   -1.8250   -1.0319 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7820    0.9292   -2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4179   -0.1170    0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7429    0.5610   -2.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1302    0.0643   -2.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0173   -0.8231   -1.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0017   -1.8097    1.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4638   -0.9707    1.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5970    1.3721   -0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2105    2.9411    1.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7894   -0.8556    1.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6406    0.4901   -0.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0182   -2.2751   -0.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 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  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
 18 20  1  0
 20 22  1  0
 20 21  2  0
 12  5  1  0
 19 33  1  0
 18 32  1  1
 14 30  1  6
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 17 31  1  0
 22 34  1  0
M  END


  Mrv1652309062223592D          

 22 22  0  0  1  0            999 V2000
    1.4289   -3.3000    0.0000 O   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
    0.0000   -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
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    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 O   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
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   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
    3.5724   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    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
  3  4  2  0  0  0  0
  4  5  1  0  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
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0238577

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2+/t10-,11+/m1/s1

> <INCHI_KEY>
SWGKAHCIOQPKFW-BOCAPUTCSA-N

> <FORMULA>
C13H12O9

> <MOLECULAR_WEIGHT>
312.23

> <EXACT_MASS>
312.048131966

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.753410738499014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
0.5979601859999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.484001795143949

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9580286110976193

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3456129955412335

> <JCHEM_POLAR_SURFACE_AREA>
161.59

> <JCHEM_REFRACTIVITY>
69.74289999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0       2.667  -6.160   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.336  -3.850   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002  -6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    2   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R)-trans-Caffeoyl tartaric acid	ChEBI
trans-Caftaric acid	ChEBI
(2S,3R)-trans-Caffeoyl tartarate	Generator
trans-Caftarate	Generator
(2S,3R)-trans-Caftarate	Generator

Chemical Formula

C₁₃H₁₂O₉

Average Mass

312.2300 Da

Monoisotopic Mass

312.04813 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2+/t10-,11+/m1/s1

InChI Key

SWGKAHCIOQPKFW-BOCAPUTCSA-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
Vitis aestivalis	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633

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

Cinnamic acid ester
Coumaric acid or derivatives
Tricarboxylic acid or derivatives
Styrene
Catechol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Sugar acid
Fatty acid ester
Phenol
Beta-hydroxy acid
Fatty acyl
Benzenoid
Hydroxy acid
Alpha-hydroxy acid
Monosaccharide
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

catechols (CHEBI:76075 )
cinnamate ester (CHEBI:76075 )
dicarboxylic acid (CHEBI:76075 )
tetraric acid derivative (CHEBI:76075 )

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	0.6	ChemAxon
pKa (Strongest Acidic)	2.96	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	161.59 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	69.74 m³·mol⁻¹	ChemAxon
Polarizability	27.75 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

C00057128

Chemspider ID

30785778

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13887348

PDB ID

Not Available

ChEBI ID

76075

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r)-trans-caftaric acid (NP0238577)

MOL for NP0238577 ((2s,3r)-trans-caftaric acid)

3D MOL for NP0238577 ((2s,3r)-trans-caftaric acid)

3D SDF for NP0238577 ((2s,3r)-trans-caftaric acid)

3D-SDF for NP0238577 ((2s,3r)-trans-caftaric acid)

PDB for NP0238577 ((2s,3r)-trans-caftaric acid)

3D PDB for NP0238577 ((2s,3r)-trans-caftaric acid)

SMILES for NP0238577 ((2s,3r)-trans-caftaric acid)

INCHI for NP0238577 ((2s,3r)-trans-caftaric acid)

Structure for NP0238577 ((2s,3r)-trans-caftaric acid)

3D Structure for NP0238577 ((2s,3r)-trans-caftaric acid)