NP-MRD: Showing NP-Card for trans-p-Coumaroyltartaric acid (NP0048028)

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Record Information

Version

2.0

Created at

2022-03-17 20:49:55 UTC

Updated at

2022-03-17 20:49:55 UTC

NP-MRD ID

NP0048028

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trans-p-Coumaroyltartaric acid

Description

Mono-trans-p-coumaroylmesotartaric acid belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. Mono-trans-p-coumaroylmesotartaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Mono-trans-p-coumaroylmesotartaric acid has been detected, but not quantified in, a few different foods, such as alcoholic beverages, common grapes, and fruits. This could make mono-trans-p-coumaroylmesotartaric acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 12021209562D          

 22 22  0  0  0  0            999 V2000
    1.3220   -1.7299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0365   -1.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7510   -1.7299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7510    0.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7510   -0.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0365   -0.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3220   -0.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655   -0.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6076   -0.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6076   -1.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069   -0.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8214   -0.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5358   -0.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503   -0.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9648   -0.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9648    0.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503    1.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5358    0.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6793    1.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    1.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    1.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1799    0.7451    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  6  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 18  2  0  0  0  0
  4 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048028

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O8/c15-9-4-1-8(2-5-9)3-6-12(19)22-13(14(20)21)10(16)7-11(17)18/h1-6,10,13,15-16H,7H2,(H,17,18)(H,20,21)/b6-3+

> <INCHI_KEY>
WZHTXSWUIFRTCQ-ZZXKWVIFSA-N

> <FORMULA>
C14H14O8

> <MOLECULAR_WEIGHT>
310.2562

> <EXACT_MASS>
310.068867424

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
28.78326003693723

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.33

> <JCHEM_LOGP>
0.9863490263333331

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.908822132819263

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1492507779418455

> <JCHEM_PKA_STRONGEST_BASIC>
-3.389980557134713

> <JCHEM_POLAR_SURFACE_AREA>
141.36

> <JCHEM_REFRACTIVITY>
72.38629999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.79e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-DEC-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-DEC-12         0                                  
HETATM    1  O   UNK     0       2.468  -3.229   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.801  -2.459   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.135  -3.229   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.135   1.391   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.135  -0.149   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.801  -0.919   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.468  -0.149   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       6.469  -0.919   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.134  -0.919   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.134  -2.459   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.200  -0.149   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.533  -0.919   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.867  -0.149   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.201  -0.919   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.534  -0.149   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.534   1.391   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.201   2.161   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.867   1.391   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.868   2.161   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.469   2.161   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.469   3.701   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.802   1.391   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2                                                            
CONECT    4    5   20                                                       
CONECT    5    4    6    8                                                  
CONECT    6    2    5    7                                                  
CONECT    7    6    9                                                       
CONECT    8    5                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   13   17                                                       
CONECT   19   16                                                            
CONECT   20    4   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
mono-trans-p-Coumaroylmesotartarate	Generator
3-Hydroxy-2-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}pentanedioate	Generator
trans-p-Coumaroyltartarate	Generator

Chemical Formula

C₁₄H₁₄O₈

Average Mass

310.2562 Da

Monoisotopic Mass

310.06887 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

27174-06-7

SMILES

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

InChI Identifier

InChI=1S/C14H14O8/c15-9-4-1-8(2-5-9)3-6-12(19)22-13(14(20)21)10(16)7-11(17)18/h1-6,10,13,15-16H,7H2,(H,17,18)(H,20,21)/b6-3+

InChI Key

WZHTXSWUIFRTCQ-ZZXKWVIFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Cinnamic acid ester
Coumaric acid or derivatives
Tricarboxylic acid or derivatives
Styrene
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Phenol
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Monosaccharide
Hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Carbonyl group
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	1.33	ALOGPS
logP	0.99	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.15	ChemAxon
pKa (Strongest Basic)	-3.4	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	8	ChemAxon
Refractivity	72.39 m³·mol⁻¹	ChemAxon
Polarizability	28.78 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

HMDB0029783

DrugBank ID

Not Available

Phenol Explorer Compound ID

470

FoodDB ID

FDB013138

KNApSAcK ID

Not Available

Chemspider ID

8284110

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10108584

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for trans-p-Coumaroyltartaric acid (NP0048028)

MOL for NP0048028 (trans-p-Coumaroyltartaric acid)

3D MOL for NP0048028 (trans-p-Coumaroyltartaric acid)

3D SDF for NP0048028 (trans-p-Coumaroyltartaric acid)

3D-SDF for NP0048028 (trans-p-Coumaroyltartaric acid)

PDB for NP0048028 (trans-p-Coumaroyltartaric acid)

3D PDB for NP0048028 (trans-p-Coumaroyltartaric acid)

SMILES for NP0048028 (trans-p-Coumaroyltartaric acid)

INCHI for NP0048028 (trans-p-Coumaroyltartaric acid)

Structure for NP0048028 (trans-p-Coumaroyltartaric acid)

3D Structure for NP0048028 (trans-p-Coumaroyltartaric acid)