NP-MRD: Showing NP-Card for (2r,3r)-2-hydroxy-3-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid (NP0307853)

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Record Information

Version

2.0

Created at

2022-09-11 01:16:25 UTC

Updated at

2022-09-11 01:16:25 UTC

NP-MRD ID

NP0307853

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r)-2-hydroxy-3-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

Description

Cis-coutaric acid, also known as cis-coutarate, belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. (2r,3r)-2-hydroxy-3-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid is found in Vitis cordifolia and Vitis vinifera. Based on a literature review very few articles have been published on cis-coutaric acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
   -0.2197   -0.4285    0.4792 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2998    0.2098   -0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2498    1.2058   -1.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4438    1.6684   -1.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4869    1.3486   -0.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4609    0.9893    0.9678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6104    0.5920    1.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8482    0.5363    1.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9926    0.1322    1.7145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8946    0.9052   -0.2937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7671    1.2939   -0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6831   -0.1510   -0.6113 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2744   -1.1220    0.2190 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9112   -2.2013   -0.5931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8439   -2.1131   -1.8460 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5603   -3.2740   -0.0079 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4040   -0.4676    1.0068 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9685   -1.4711    1.8239 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4770   -0.0227    0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6360   -0.5047    0.0867 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2078    0.9719   -0.8592 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4450    1.6155   -2.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6972    2.4561   -2.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5317    1.0919    1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5440    0.3046    2.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2637   -0.8557    1.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8784    0.8685   -0.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8852    1.5709   -1.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5701   -1.5359    0.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115   -4.0127    0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0733    0.3891    1.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7741   -1.8514    1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6343    1.8617   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 13  1  0
 13 12  1  0
 12  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  2  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
 17 19  1  0
 19 21  1  0
 19 20  2  0
 11  5  1  0
 18 32  1  0
 17 31  1  1
 13 29  1  1
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 16 30  1  0
 21 33  1  0
M  END


  Mrv1652309112203162D          

 21 21  0  0  1  0            999 V2000
    2.1434   -2.0625    0.0000 O   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
    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
    3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 O   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
  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  2  0  0  0  0
  5 11  1  0  0  0  0
  2 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0307853

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O8/c14-8-4-1-7(2-5-8)3-6-9(15)21-11(13(19)20)10(16)12(17)18/h1-6,10-11,14,16H,(H,17,18)(H,19,20)/b6-3-/t10-,11-/m1/s1

> <INCHI_KEY>
INYJZRKTYXTZHP-KQLCGWBMSA-N

> <FORMULA>
C13H12O8

> <MOLECULAR_WEIGHT>
296.231

> <EXACT_MASS>
296.053217346

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.784695976689235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2-hydroxy-3-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

> <JCHEM_LOGP>
0.9015255076666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.630014618327389

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.151380429466035

> <JCHEM_PKA_STRONGEST_BASIC>
-4.345612995541209

> <JCHEM_POLAR_SURFACE_AREA>
141.35999999999999

> <JCHEM_REFRACTIVITY>
67.762

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-hydroxy-3-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002   3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.669  -1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    2   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
cis-Coutarate	Generator

Chemical Formula

C₁₃H₁₂O₈

Average Mass

296.2310 Da

Monoisotopic Mass

296.05322 Da

IUPAC Name

(2R,3R)-2-hydroxy-3-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

Traditional Name

(2R,3R)-2-hydroxy-3-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H12O8/c14-8-4-1-7(2-5-8)3-6-9(15)21-11(13(19)20)10(16)12(17)18/h1-6,10-11,14,16H,(H,17,18)(H,19,20)/b6-3-/t10-,11-/m1/s1

InChI Key

INYJZRKTYXTZHP-KQLCGWBMSA-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 cordifolia	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

Coumaric acid ester
Coumaric acid or derivatives
Cinnamic acid ester
Tricarboxylic acid or derivatives
Styrene
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Phenol
Sugar acid
Beta-hydroxy acid
Hydroxy acid
Monocyclic benzene moiety
Alpha-hydroxy acid
Monosaccharide
Fatty acyl
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen 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	0.9	ChemAxon
pKa (Strongest Acidic)	3.15	ChemAxon
pKa (Strongest Basic)	-4.3	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	7	ChemAxon
Refractivity	67.76 m³·mol⁻¹	ChemAxon
Polarizability	25.78 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

103883481

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102445591

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r)-2-hydroxy-3-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid (NP0307853)

MOL for NP0307853 ((2r,3r)-2-hydroxy-3-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid)

3D MOL for NP0307853 ((2r,3r)-2-hydroxy-3-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid)

3D SDF for NP0307853 ((2r,3r)-2-hydroxy-3-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid)

3D-SDF for NP0307853 ((2r,3r)-2-hydroxy-3-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid)

PDB for NP0307853 ((2r,3r)-2-hydroxy-3-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid)

3D PDB for NP0307853 ((2r,3r)-2-hydroxy-3-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid)

SMILES for NP0307853 ((2r,3r)-2-hydroxy-3-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid)

INCHI for NP0307853 ((2r,3r)-2-hydroxy-3-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid)

Structure for NP0307853 ((2r,3r)-2-hydroxy-3-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid)

3D Structure for NP0307853 ((2r,3r)-2-hydroxy-3-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid)