NP-MRD: Showing NP-Card for (2s,3s)-trans-fertaric acid (NP0269264)

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Record Information

Version

2.0

Created at

2022-09-08 14:40:08 UTC

Updated at

2022-09-08 14:40:09 UTC

NP-MRD ID

NP0269264

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s)-trans-fertaric acid

Description

(2S,3S)-trans-fertaric 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. (2s,3s)-trans-fertaric acid is found in Vitis vinifera. A cinnamate ester obtained by formal condensation of the carboxy group of trans-ferulic acid with one of the hydroxy groups of D-tartaric acid (2S,3S)-trans-fertaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 37  0  0  0  0  0  0  0  0999 V2000
   -5.1712    1.8826   -0.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4486    0.7938   -0.0197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4119   -0.0152    0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0995    0.1886    0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0927   -0.6272    0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6877   -0.4114    0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2823    0.5477   -0.6318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1583    0.6716   -0.9476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5436    1.5951   -1.7023 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1028   -0.1926   -0.4429 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4634    0.0100   -0.8056 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0431   -1.1804   -1.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3561   -2.2527   -1.5462 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3306   -1.2388   -1.9316 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1420    0.3977    0.5183 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4361    1.5732    0.9128 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5678    0.6783    0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9712    1.8811    0.5381 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5438   -0.2460    0.1017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224   -1.6789    1.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7273   -1.8842    1.7310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7287   -1.0684    1.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0353   -1.3090    1.6542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1033    2.4537   -1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4044    2.5309   -0.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7580    1.5338   -1.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8903    1.0289   -0.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0413   -1.1078    0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9786    1.2390   -1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5490    0.8678   -1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5968   -0.5547   -2.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8808   -0.3656    1.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2657    1.5527    1.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6398   -1.1524    0.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6123   -2.3133    1.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9565   -2.7261    2.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8212   -0.7627    1.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 22  2  0
 22 23  1  0
 22 21  1  0
 21 20  2  0
 20  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 15  1  0
 15 16  1  0
 15 17  1  0
 17 19  1  0
 17 18  2  0
 11 12  1  0
 12 14  1  0
 12 13  2  0
  5  4  2  0
  4  3  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 23 37  1  0
 21 36  1  0
 20 35  1  0
  6 28  1  0
  7 29  1  0
 11 30  1  6
 15 32  1  1
 16 33  1  0
 19 34  1  0
 14 31  1  0
  4 27  1  0
M  END

641605
  Mrv0541 02271202072D          

 23 23  0  0  1  0            999 V2000
    5.2224    1.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.9347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.1722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.0154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.5847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.9347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.5847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.8405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.9347    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9370    2.3472    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5080    2.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  6  0  0  0
  1 16  1  0  0  0  0
 11  2  1  1  0  0  0
  3 12  1  0  0  0  0
  4 18  1  0  0  0  0
  4 23  1  0  0  0  0
  5 14  1  0  0  0  0
  6 12  2  0  0  0  0
  7 14  2  0  0  0  0
  8 21  1  0  0  0  0
  9 16  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13 17  1  0  0  0  0
 13 19  1  0  0  0  0
 15 18  1  0  0  0  0
 16 20  1  0  0  0  0
 17 20  2  0  0  0  0
 18 21  2  0  0  0  0
 19 22  2  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0269264

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(\C=C\C(=O)O[C@@H]([C@H](O)C(O)=O)C(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O9/c1-22-9-6-7(2-4-8(9)15)3-5-10(16)23-12(14(20)21)11(17)13(18)19/h2-6,11-12,15,17H,1H3,(H,18,19)(H,20,21)/b5-3+/t11-,12-/m0/s1

> <INCHI_KEY>
XIWXUSFCUBAMFH-SCBUBVSKSA-N

> <FORMULA>
C14H14O9

> <MOLECULAR_WEIGHT>
326.2556

> <EXACT_MASS>
326.063782046

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
29.91345962575531

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S)-2-hydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}butanedioic acid

> <ALOGPS_LOGP>
1.36

> <JCHEM_LOGP>
0.7438542420000003

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.47823248663642

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.951276504214371

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3456129955412335

> <JCHEM_POLAR_SURFACE_AREA>
150.58999999999997

> <JCHEM_REFRACTIVITY>
74.2252

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-2-hydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 641605                                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0       9.748   2.071   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      12.416   3.611   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.415   5.921   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.414  -5.629   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      12.416   6.691   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       7.081   3.611   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       9.748   6.691   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       7.081  -7.169   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       7.081   2.071   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.748   3.611   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.082   4.381   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415   4.381   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -2.549   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.082   5.921   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.747  -3.319   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415   1.301   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081  -1.009   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.747  -4.859   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415  -3.319   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415  -0.239   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.081  -5.629   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.415  -4.859   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080  -4.859   0.000  0.00  0.00           C+0
CONECT    1   10   16                                                       
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   18   23                                                       
CONECT    5   14                                                            
CONECT    6   12                                                            
CONECT    7   14                                                            
CONECT    8   21                                                            
CONECT    9   16                                                            
CONECT   10    1   11   12                                                  
CONECT   11    2   10   14                                                  
CONECT   12    3    6   10                                                  
CONECT   13   15   17   19                                                  
CONECT   14    5    7   11                                                  
CONECT   15   13   18                                                       
CONECT   16    1    9   20                                                  
CONECT   17   13   20                                                       
CONECT   18    4   15   21                                                  
CONECT   19   13   22                                                       
CONECT   20   16   17                                                       
CONECT   21    8   18   22                                                  
CONECT   22   19   21                                                       
CONECT   23    4                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Value	Source
(2S,3S)-trans-Fertarate	Generator

Chemical Formula

C₁₄H₁₄O₉

Average Mass

326.2556 Da

Monoisotopic Mass

326.06378 Da

IUPAC Name

(2S,3S)-2-hydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}butanedioic acid

Traditional Name

(2S,3S)-2-hydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}butanedioic acid

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(\C=C\C(=O)O[C@@H]([C@H](O)C(O)=O)C(O)=O)=C1

InChI Identifier

InChI=1S/C14H14O9/c1-22-9-6-7(2-4-8(9)15)3-5-10(16)23-12(14(20)21)11(17)13(18)19/h2-6,11-12,15,17H,1H3,(H,18,19)(H,20,21)/b5-3+/t11-,12-/m0/s1

InChI Key

XIWXUSFCUBAMFH-SCBUBVSKSA-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 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

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:76120 )
phenols (CHEBI:76120 )
cinnamate ester (CHEBI:76120 )
dicarboxylic acid (CHEBI:76120 )
tetraric acid derivative (CHEBI:76120 )

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	1.36	ALOGPS
logP	0.74	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	2.95	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.59 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	74.23 m³·mol⁻¹	ChemAxon
Polarizability	29.91 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

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

641605

PDB ID

Not Available

ChEBI ID

76120

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3s)-trans-fertaric acid (NP0269264)

MOL for NP0269264 ((2s,3s)-trans-fertaric acid)

3D MOL for NP0269264 ((2s,3s)-trans-fertaric acid)

3D SDF for NP0269264 ((2s,3s)-trans-fertaric acid)

3D-SDF for NP0269264 ((2s,3s)-trans-fertaric acid)

PDB for NP0269264 ((2s,3s)-trans-fertaric acid)

3D PDB for NP0269264 ((2s,3s)-trans-fertaric acid)

SMILES for NP0269264 ((2s,3s)-trans-fertaric acid)

INCHI for NP0269264 ((2s,3s)-trans-fertaric acid)

Structure for NP0269264 ((2s,3s)-trans-fertaric acid)

3D Structure for NP0269264 ((2s,3s)-trans-fertaric acid)