NP-MRD: Showing NP-Card for L-Malic acid 2-O-gallate (NP0073005)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 18:16:09 UTC

Updated at

2022-04-28 18:16:09 UTC

NP-MRD ID

NP0073005

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-Malic acid 2-O-gallate

Description

2-O-Galloyl-L-malic acid, also known as 2-O-galloyl-L-malate, belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid. L-Malic acid 2-O-gallate is found in Phyllanthus emblica . Based on a literature review very few articles have been published on 2-O-Galloyl-L-malic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
   -2.4255   -2.0973    0.2845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5040   -1.5509   -0.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6971   -2.1085    0.3312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4617   -0.3608   -0.9658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5851    0.7329   -0.3718 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2515    0.3281   -0.1681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1772    0.9441   -0.7996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4598    1.8947   -1.5729 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1937    0.5164   -0.5817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940    1.1853   -1.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4995    0.7980   -1.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    1.4369   -1.7157 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7868   -0.2413   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1247   -0.6079   -0.0191 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7980   -0.9058    0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0159   -1.9423    1.3396 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4637   -0.5212    0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1654    1.2214    0.9191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3316    1.6513    0.9465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3909    1.1845    2.0580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7997   -2.9691    0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -0.6792   -1.9306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4710    0.0602   -1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6271    1.5891   -1.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9886    1.9898   -1.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5025    1.2066   -1.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3860   -1.3480    0.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9052   -2.3092    1.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6679   -1.0241    0.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7094    1.9264    2.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  5 18  1  0
 18 20  1  0
 18 19  2  0
 17  9  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  6
 10 25  1  0
 12 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 20 30  1  0
M  END


  Mrv1652304282220162D          

 20 20  0  0  1  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   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
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  3 18  1  0  0  0  0
  2 19  1  0  0  0  0
  1 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073005

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O9/c12-5-1-4(2-6(13)9(5)16)11(19)20-7(10(17)18)3-8(14)15/h1-2,7,12-13,16H,3H2,(H,14,15)(H,17,18)/t7-/m0/s1

> <INCHI_KEY>
NSOJLVUORKKGRI-ZETCQYMHSA-N

> <FORMULA>
C11H10O9

> <MOLECULAR_WEIGHT>
286.192

> <EXACT_MASS>
286.032481902

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
24.637585076549176

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-(3,4,5-trihydroxybenzoyloxy)butanedioic acid

> <ALOGPS_LOGP>
1.21

> <JCHEM_LOGP>
0.47096245566666667

> <ALOGPS_LOGS>
-2.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.369869351321366

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.591824557347165

> <JCHEM_PKA_STRONGEST_BASIC>
-5.548976327796216

> <JCHEM_POLAR_SURFACE_AREA>
161.59

> <JCHEM_REFRACTIVITY>
60.639900000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-(3,4,5-trihydroxybenzoyloxy)butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    3                                                            
CONECT   19    2                                                            
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
2-O-Galloyl-L-malate	Generator

Chemical Formula

C₁₁H₁₀O₉

Average Mass

286.1920 Da

Monoisotopic Mass

286.03248 Da

IUPAC Name

(2S)-2-(3,4,5-trihydroxybenzoyloxy)butanedioic acid

Traditional Name

(2S)-2-(3,4,5-trihydroxybenzoyloxy)butanedioic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C[C@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C11H10O9/c12-5-1-4(2-6(13)9(5)16)11(19)20-7(10(17)18)3-8(14)15/h1-2,7,12-13,16H,3H2,(H,14,15)(H,17,18)/t7-/m0/s1

InChI Key

NSOJLVUORKKGRI-ZETCQYMHSA-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
Phyllanthus emblica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Galloyl esters

Alternative Parents

Substituents

Galloyl ester
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzenetriol
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Polyol
Carboxylic acid
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
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	1.21	ALOGPS
logP	0.47	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.59	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	161.59 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	60.64 m³·mol⁻¹	ChemAxon
Polarizability	24.64 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

62903768

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101010963

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for L-Malic acid 2-O-gallate (NP0073005)

MOL for NP0073005 (L-Malic acid 2-O-gallate)

3D MOL for NP0073005 (L-Malic acid 2-O-gallate)

3D SDF for NP0073005 (L-Malic acid 2-O-gallate)

3D-SDF for NP0073005 (L-Malic acid 2-O-gallate)

PDB for NP0073005 (L-Malic acid 2-O-gallate)

3D PDB for NP0073005 (L-Malic acid 2-O-gallate)

SMILES for NP0073005 (L-Malic acid 2-O-gallate)

INCHI for NP0073005 (L-Malic acid 2-O-gallate)

Structure for NP0073005 (L-Malic acid 2-O-gallate)

3D Structure for NP0073005 (L-Malic acid 2-O-gallate)