NP-MRD: Showing NP-Card for 2-O-Feruloyltartronic acid (NP0334914)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-10 23:03:16 UTC

Updated at

2024-09-10 23:03:17 UTC

NP-MRD ID

NP0334914

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-O-Feruloyltartronic acid

Description

2-O-Feruloyltartronic 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. 2-O-Feruloyltartronic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-O-Feruloyltartronic acid has been detected, but not quantified in, pulses. This could make 2-O-feruloyltartronic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061306492D          

 21 21  0  0  0  0            999 V2000
   -5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 C   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
   -0.7145    2.8875    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    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 O   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
    0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  7  2  1  0  0  0  0
  7  3  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  5  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 15 10  2  0  0  0  0
 16 12  2  0  0  0  0
 17 12  1  0  0  0  0
 18 13  2  0  0  0  0
 19 13  1  0  0  0  0
 20  1  1  0  0  0  0
 20  9  1  0  0  0  0
 21 10  1  0  0  0  0
 21 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334914

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O8/c1-20-9-6-7(2-4-8(9)14)3-5-10(15)21-11(12(16)17)13(18)19/h2-6,11,14H,1H3,(H,16,17)(H,18,19)/b5-3+

> <INCHI_KEY>
ZWXOJLRXYPVVQY-HWKANZROSA-N

> <FORMULA>
C13H12O8

> <MOLECULAR_WEIGHT>
296.2296

> <EXACT_MASS>
296.05321736

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
27.2849444462551

> <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}propanedioic acid

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.5263784016666664

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.606564270866936

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1576734702954035

> <JCHEM_PKA_STRONGEST_BASIC>
-4.889288345883923

> <JCHEM_POLAR_SURFACE_AREA>
130.35999999999999

> <JCHEM_REFRACTIVITY>
68.33780000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.23e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0     -10.669  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335  12.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  13.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668  10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.002  12.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -9.336  13.090   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667   3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   7.700   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -9.336  10.010   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    4    7                                                       
CONECT    3    5    7                                                       
CONECT    4    2    8                                                       
CONECT    5    3   10                                                       
CONECT    6    7    9                                                       
CONECT    7    2    3    6                                                  
CONECT    8    4    9   14                                                  
CONECT    9    6    8   20                                                  
CONECT   10    5   15   21                                                  
CONECT   11   12   13   21                                                  
CONECT   12   11   16   17                                                  
CONECT   13   11   18   19                                                  
CONECT   14    8                                                            
CONECT   15   10                                                            
CONECT   16   12                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19   13                                                            
CONECT   20    1    9                                                       
CONECT   21   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
2-O-Feruloyltartronate	Generator
2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propanedioate	Generator

Chemical Formula

C₁₃H₁₂O₈

Average Mass

296.2296 Da

Monoisotopic Mass

296.05322 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(\C=C\C(=O)OC(C(O)=O)C(O)=O)=C1

InChI Identifier

InChI=1S/C13H12O8/c1-20-9-6-7(2-4-8(9)14)3-5-10(15)21-11(12(16)17)13(18)19/h2-6,11,14H,1H3,(H,16,17)(H,18,19)/b5-3+

InChI Key

ZWXOJLRXYPVVQY-HWKANZROSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Monosaccharide
1,3-dicarbonyl compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
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	1.63	ALOGPS
logP	1.53	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	2.16	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	7	ChemAxon
Refractivity	68.34 m³·mol⁻¹	ChemAxon
Polarizability	27.28 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

HMDB0032957

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010943

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-O-Feruloyltartronic acid (NP0334914)

MOL for NP0334914 (2-O-Feruloyltartronic acid)

3D MOL for NP0334914 (2-O-Feruloyltartronic acid)

3D SDF for NP0334914 (2-O-Feruloyltartronic acid)

3D-SDF for NP0334914 (2-O-Feruloyltartronic acid)

PDB for NP0334914 (2-O-Feruloyltartronic acid)

3D PDB for NP0334914 (2-O-Feruloyltartronic acid)

SMILES for NP0334914 (2-O-Feruloyltartronic acid)

INCHI for NP0334914 (2-O-Feruloyltartronic acid)

Structure for NP0334914 (2-O-Feruloyltartronic acid)

3D Structure for NP0334914 (2-O-Feruloyltartronic acid)