NP-MRD: Showing NP-Card for galop; malic acid (NP0152299)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 08:44:35 UTC

Updated at

2022-09-02 08:44:36 UTC

NP-MRD ID

NP0152299

Secondary Accession Numbers

None

Natural Product Identification

Common Name

galop; malic acid

Description

2-Hydroxybutanedioic acid; 3,4,5-trihydroxybenzoic acid belongs to the class of organic compounds known as gallic acids. These are organic compounds that contain a 3,4,5-trihydroxybenzoic acid moiety. galop; malic acid is found in Phyllanthus emblica. Based on a literature review very few articles have been published on 2-hydroxybutanedioic acid; 3,4,5-trihydroxybenzoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 32  0  0  0  0  0  0  0  0999 V2000
   -0.7634   -1.5282   -1.2018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3836   -0.6073   -0.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6390   -0.2880   -1.1185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8133    0.1341    0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5666   -0.2488    0.8872 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8587    0.6177    1.9796 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6325   -0.0092   -0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5515    0.8277    0.1013 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6911   -0.7053   -1.2770 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7953   -1.8491   -0.3625 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4410   -0.6728   -0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3932    0.2730    0.1595 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0562   -0.3053   -0.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6656    0.9849   -0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6748    1.2857   -0.0937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0757    2.6069    0.1421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6559    0.3528   -0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9685    0.7670   -0.4691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2380   -0.9348   -0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1664   -1.9025   -0.9463 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -1.2553   -0.5447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9137    0.6216   -1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7632    1.2482    0.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4603    0.0380    1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6164   -1.2849    1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8050    1.5245    1.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0147   -0.3400   -2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5946    0.5112    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714    1.7848    0.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3945    3.3159    0.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7411    0.1786   -0.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9369   -2.8650   -1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4172   -2.2760   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  5  7  1  0
  7  9  1  0
  7  8  2  0
 12 11  1  0
 11 10  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 21 13  1  0
  6 26  1  0
  5 25  1  1
  4 23  1  0
  4 24  1  0
  3 22  1  0
  9 27  1  0
 12 28  1  0
 14 29  1  0
 16 30  1  0
 18 31  1  0
 20 32  1  0
 21 33  1  0
M  END


  Mrv1652309022210442D          

 21 20  0  0  0  0            999 V2000
   -1.8259   -0.3208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1114    0.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1114    0.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3969   -0.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3175    0.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3175    0.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -0.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465    0.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -1.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3467    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0611    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7756    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0611    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7756    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7756   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4901   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0611   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0611   -1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3467   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6322   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3467    0.2063    0.0000 C   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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  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 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 13 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0152299

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O5.C4H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10;5-2(4(8)9)1-3(6)7/h1-2,8-10H,(H,11,12);2,5H,1H2,(H,6,7)(H,8,9)

> <INCHI_KEY>
XGSMBLOVTFFBMG-UHFFFAOYSA-N

> <FORMULA>
C11H12O10

> <MOLECULAR_WEIGHT>
304.207

> <EXACT_MASS>
304.043046586

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
14.757737029503335

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxybutanedioic acid; 3,4,5-trihydroxybenzoic acid

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
0.720132759

> <ALOGPS_LOGS>
-1.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.044962714429534

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9415641190048674

> <JCHEM_PKA_STRONGEST_BASIC>
-6.048647901640675

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
39.2569

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.94e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
galop; malic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0      -3.408  -0.599   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.075   0.171   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.075   1.711   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.741  -0.599   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.593   0.171   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.593   1.711   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.926  -0.599   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.260   0.171   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.926  -2.139   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       8.114   3.465   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.447   2.695   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.781   3.465   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.447   1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.781   0.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.781  -1.155   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.115  -1.925   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.447  -1.925   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.447  -3.465   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.114  -1.155   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.780  -1.925   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.114   0.385   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10   11                                                            
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   13                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxybutanedioate; 3,4,5-trihydroxybenzoate	Generator

Chemical Formula

C₁₁H₁₂O₁₀

Average Mass

304.2070 Da

Monoisotopic Mass

304.04305 Da

IUPAC Name

2-hydroxybutanedioic acid; 3,4,5-trihydroxybenzoic acid

Traditional Name

galop; malic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C7H6O5.C4H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10;5-2(4(8)9)1-3(6)7/h1-2,8-10H,(H,11,12);2,5H,1H2,(H,6,7)(H,8,9)

InChI Key

XGSMBLOVTFFBMG-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gallic acids. These are organic compounds that contain a 3,4,5-trihydroxybenzoic acid moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Gallic acids

Alternative Parents

Substituents

Gallic acid
Pyrogallol derivative
Benzoic acid
Benzenetriol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Short-chain hydroxy acid
Phenol
Beta-hydroxy acid
Fatty acid
Hydroxy acid
Dicarboxylic acid or derivatives
Alpha-hydroxy acid
Secondary alcohol
Polyol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Not Available

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	1.17	ALOGPS
logP	0.72	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.94	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	39.26 m³·mol⁻¹	ChemAxon
Polarizability	14.76 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

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

163189925

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for galop; malic acid (NP0152299)

MOL for NP0152299 (galop; malic acid)

3D MOL for NP0152299 (galop; malic acid)

3D SDF for NP0152299 (galop; malic acid)

3D-SDF for NP0152299 (galop; malic acid)

PDB for NP0152299 (galop; malic acid)

3D PDB for NP0152299 (galop; malic acid)

SMILES for NP0152299 (galop; malic acid)

INCHI for NP0152299 (galop; malic acid)

Structure for NP0152299 (galop; malic acid)

3D Structure for NP0152299 (galop; malic acid)