NP-MRD: Showing NP-Card for Feruloylmalic acid (NP0083998)

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Record Information

Version

2.0

Created at

2022-04-29 04:52:13 UTC

Updated at

2022-04-29 04:52:13 UTC

NP-MRD ID

NP0083998

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Feruloylmalic acid

Description

Feruloyl malate 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. Feruloylmalic acid is found in Raphanus sativus and Vicia faba . Feruloylmalic acid was first documented in 2006 (PMID: 17080307). Based on a literature review a small amount of articles have been published on feruloyl malate (PMID: 20829305) (PMID: 20705362) (PMID: 18046574).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
   -5.0912    1.8380    1.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3536    0.5678    0.7081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3386   -0.2505    0.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0083    0.1268    0.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9857   -0.6681   -0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6072   -0.2703   -0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1974    0.8677    0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2456    1.1495    0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7203    2.2164    0.8474 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1611    0.2318   -0.1169 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5629    0.5012   -0.1173 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3014   -0.5314    0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7428   -0.2536    0.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5888   -1.1366    1.1063 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2923    0.9624    0.3819 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9695    0.4905   -1.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0632    0.2576   -2.4101 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2778    0.7210   -1.9416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3597   -1.8983   -0.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6643   -2.3247   -0.7779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6483   -1.4845   -0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9990   -1.8390   -0.3460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3531    2.3975    0.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6827    1.6805    2.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0460    2.4019    1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7915    1.0878    0.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1420   -0.9773   -0.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551    1.5921    0.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7014    1.4991    0.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9161   -0.5835    1.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1619   -1.5260    0.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1296    1.7876    0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7502   -0.0836   -2.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5530   -2.5349   -1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9428   -3.2835   -1.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2493   -2.7315   -0.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 21  2  0
 21 22  1  0
 21 20  1  0
 20 19  2  0
 19  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 12  1  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
 11 16  1  0
 16 18  1  0
 16 17  2  0
  5  4  2  0
  4  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 22 36  1  0
 20 35  1  0
 19 34  1  0
  6 27  1  0
  7 28  1  0
 11 29  1  1
 12 30  1  0
 12 31  1  0
 15 32  1  0
 18 33  1  0
  4 26  1  0
M  END


  Mrv1652304292206522D          

 22 22  0  0  0  0            999 V2000
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   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
    0.0000    4.1250    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  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
    5.7158    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    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
  1  2  1  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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 11 21  2  0  0  0  0
  8 22  2  0  0  0  0
  3 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083998

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(\C=C\C(=O)OC(CC(O)=O)C(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O8/c1-21-10-6-8(2-4-9(10)15)3-5-13(18)22-11(14(19)20)7-12(16)17/h2-6,11,15H,7H2,1H3,(H,16,17)(H,19,20)/b5-3+

> <INCHI_KEY>
NZLXTWAEDURRNL-HWKANZROSA-N

> <FORMULA>
C14H14O8

> <MOLECULAR_WEIGHT>
310.258

> <EXACT_MASS>
310.068867411

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.15764375261208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.39

> <JCHEM_LOGP>
1.459012702666667

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.00435240177035

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.062899415986902

> <JCHEM_PKA_STRONGEST_BASIC>
-4.889059329492035

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
72.887

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.000   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   7.700   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002   3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.337   3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.003   0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   11                                                            
CONECT   22    8    3                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
Feruloyl malic acid	Generator

Chemical Formula

C₁₄H₁₄O₈

Average Mass

310.2580 Da

Monoisotopic Mass

310.06887 Da

IUPAC Name

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

Traditional Name

2-{[(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)OC(CC(O)=O)C(O)=O)=C1

InChI Identifier

InChI=1S/C14H14O8/c1-21-10-6-8(2-4-9(10)15)3-5-13(18)22-11(14(19)20)7-12(16)17/h2-6,11,15H,7H2,1H3,(H,16,17)(H,19,20)/b5-3+

InChI Key

NZLXTWAEDURRNL-HWKANZROSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Raphanus sativus	Plant	KNApSAcK
Vicia faba	Plant	KNApSAcK

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
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	1.39	ALOGPS
logP	1.46	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.06	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	72.89 m³·mol⁻¹	ChemAxon
Polarizability	29.16 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

C00053173

Chemspider ID

29814101

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71694479

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Thevenin J, Pollet B, Letarnec B, Saulnier L, Gissot L, Maia-Grondard A, Lapierre C, Jouanin L: The simultaneous repression of CCR and CAD, two enzymes of the lignin biosynthetic pathway, results in sterility and dwarfism in Arabidopsis thaliana. Mol Plant. 2011 Jan;4(1):70-82. doi: 10.1093/mp/ssq045. Epub 2010 Sep 9. [PubMed:20829305 ]
Simoh S, Linthorst HJ, Lefeber AW, Erkelens C, Kim HK, Choi YH, Verpoorte R: Metabolic changes of Brassica rapa transformed with a bacterial isochorismate synthase gene. J Plant Physiol. 2010 Dec 15;167(18):1525-32. doi: 10.1016/j.jplph.2010.06.022. Epub 2010 Aug 11. [PubMed:20705362 ]
Mir Derikvand M, Sierra JB, Ruel K, Pollet B, Do CT, Thevenin J, Buffard D, Jouanin L, Lapierre C: Redirection of the phenylpropanoid pathway to feruloyl malate in Arabidopsis mutants deficient for cinnamoyl-CoA reductase 1. Planta. 2008 Apr;227(5):943-56. doi: 10.1007/s00425-007-0669-x. Epub 2007 Nov 29. [PubMed:18046574 ]
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Showing NP-Card for Feruloylmalic acid (NP0083998)

MOL for NP0083998 (Feruloylmalic acid)

3D MOL for NP0083998 (Feruloylmalic acid)

3D SDF for NP0083998 (Feruloylmalic acid)

3D-SDF for NP0083998 (Feruloylmalic acid)

PDB for NP0083998 (Feruloylmalic acid)

3D PDB for NP0083998 (Feruloylmalic acid)

SMILES for NP0083998 (Feruloylmalic acid)

INCHI for NP0083998 (Feruloylmalic acid)

Structure for NP0083998 (Feruloylmalic acid)

3D Structure for NP0083998 (Feruloylmalic acid)