NP-MRD: Showing NP-Card for Feruloyltartaric acid (NP0049352)

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Record Information

Version

2.0

Created at

2022-03-17 21:11:07 UTC

Updated at

2022-03-17 21:11:07 UTC

NP-MRD ID

NP0049352

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Feruloyltartaric acid

Description

Feruloyltartaric acid is found in Posidonia oceanica , Syringodium filiforme and Vitis vinifera.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241216122D          

 23 23  0  0  0  0            999 V2000
    1.9065    3.2495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920    2.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775    3.2495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514    1.5995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2369    2.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2369    2.8370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920    2.0120    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4775    1.5995    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4775    0.7745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514   -4.1755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514   -3.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6659   -2.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6659   -2.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514   -1.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2369   -2.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2369   -2.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775   -3.3505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920   -2.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514   -0.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2369   -0.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2369    0.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514    0.7745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9065    1.5995    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
  2  7  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 21  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 16  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
  7 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0049352

> <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-/m1/s1

> <INCHI_KEY>
XIWXUSFCUBAMFH-WEPHUFDCSA-N

> <FORMULA>
C14H14O9

> <MOLECULAR_WEIGHT>
326.2556

> <EXACT_MASS>
326.063782046

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
29.889335399205578

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-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>
150.59

> <JCHEM_REFRACTIVITY>
74.22519999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.39e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       3.559   6.066   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.225   5.296   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.891   6.066   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.776   2.986   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.442   3.756   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.442   5.296   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.225   3.756   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.891   2.986   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.891   1.446   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.776  -7.794   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.776  -6.254   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.110  -5.484   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.110  -3.944   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.776  -3.174   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.442  -3.944   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.442  -5.484   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.891  -6.254   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.225  -5.484   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.776  -1.634   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.442  -0.864   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.442   0.676   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.776   1.446   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.559   2.986   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2                                                            
CONECT    4    5                                                            
CONECT    5    4    6    8                                                  
CONECT    6    5                                                            
CONECT    7    2    8   23                                                  
CONECT    8    5    7    9                                                  
CONECT    9    8   21                                                       
CONECT   10   11                                                            
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   11   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   14   20                                                       
CONECT   20   19   21                                                       
CONECT   21    9   20   22                                                  
CONECT   22   21                                                            
CONECT   23    7                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Value	Source
trans-Fertaric acid	ChEBI
trans-Fertarate	Generator
Feruloyltartarate	Generator

Chemical Formula

C₁₄H₁₄O₉

Average Mass

326.2556 Da

Monoisotopic Mass

326.06378 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

1044-65-1

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-/m1/s1

InChI Key

XIWXUSFCUBAMFH-WEPHUFDCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Posidonia oceanica	Plant	KNApSAcK
Syringodium filiforme	Plant	KNApSAcK
Vitis vinifera	LOTUS Database	35616633
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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:76116 )
phenols (CHEBI:76116 )
cinnamate ester (CHEBI:76116 )
dicarboxylic acid (CHEBI:76116 )
tetraric acid derivative (CHEBI:76116 )

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	29.89 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

FDB018773

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

72551457

PDB ID

Not Available

ChEBI ID

76116

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Feruloyltartaric acid (NP0049352)

MOL for NP0049352 (Feruloyltartaric acid)

3D MOL for NP0049352 (Feruloyltartaric acid)

3D SDF for NP0049352 (Feruloyltartaric acid)

3D-SDF for NP0049352 (Feruloyltartaric acid)

PDB for NP0049352 (Feruloyltartaric acid)

3D PDB for NP0049352 (Feruloyltartaric acid)

SMILES for NP0049352 (Feruloyltartaric acid)

INCHI for NP0049352 (Feruloyltartaric acid)

Structure for NP0049352 (Feruloyltartaric acid)

3D Structure for NP0049352 (Feruloyltartaric acid)