NP-MRD: Showing NP-Card for 2-hydroperoxypropane-1,2,3-tricarboxylic acid (NP0313686)

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Record Information

Version

2.0

Created at

2022-09-11 11:23:58 UTC

Updated at

2022-09-11 11:23:58 UTC

NP-MRD ID

NP0313686

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-hydroperoxypropane-1,2,3-tricarboxylic acid

Description

Alpha-hydroxycitric acid, also known as a-hydroxycitrate, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. 2-hydroperoxypropane-1,2,3-tricarboxylic acid is found in Garcinia cowa and Garcinia gummi-gutta. Based on a literature review very few articles have been published on alpha-hydroxycitric acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112213232D          

 14 13  0  0  0  0            999 V2000
    2.8875   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0313686

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OOC(CC(O)=O)(CC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O8/c7-3(8)1-6(14-13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

> <INCHI_KEY>
OIPKKHARWZNZEQ-UHFFFAOYSA-N

> <FORMULA>
C6H8O8

> <MOLECULAR_WEIGHT>
208.122

> <EXACT_MASS>
208.021917218

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.231204724631343

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroperoxypropane-1,2,3-tricarboxylic acid

> <JCHEM_LOGP>
-0.8733520746666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.564567423854896

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9028131994923996

> <JCHEM_PKA_STRONGEST_BASIC>
-4.256501618618574

> <JCHEM_POLAR_SURFACE_AREA>
141.35999999999999

> <JCHEM_REFRACTIVITY>
36.9741

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroperoxypropane-1,2,3-tricarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  O   UNK     0       5.390  -1.334   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.390  -4.001   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.976  -2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.976  -3.644   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.310  -4.414   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.357  -4.414   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.644  -0.564   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.644   0.976   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.310   1.334   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10   12                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11                                                       
CONECT   11   10                                                            
CONECT   12    5   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
a-Hydroxycitrate	Generator
a-Hydroxycitric acid	Generator
alpha-Hydroxycitrate	Generator
Α-hydroxycitrate	Generator
Α-hydroxycitric acid	Generator

Chemical Formula

C₆H₈O₈

Average Mass

208.1220 Da

Monoisotopic Mass

208.02192 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OOC(CC(O)=O)(CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C6H8O8/c7-3(8)1-6(14-13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

InChI Key

OIPKKHARWZNZEQ-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
Garcinia cowa	LOTUS Database	35616633
Garcinia gummi-gutta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Hydroperoxide
Alkyl hydroperoxide
Peroxol
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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

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

57473313

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-hydroperoxypropane-1,2,3-tricarboxylic acid (NP0313686)

MOL for NP0313686 (2-hydroperoxypropane-1,2,3-tricarboxylic acid)

3D MOL for NP0313686 (2-hydroperoxypropane-1,2,3-tricarboxylic acid)

3D SDF for NP0313686 (2-hydroperoxypropane-1,2,3-tricarboxylic acid)

3D-SDF for NP0313686 (2-hydroperoxypropane-1,2,3-tricarboxylic acid)

PDB for NP0313686 (2-hydroperoxypropane-1,2,3-tricarboxylic acid)

3D PDB for NP0313686 (2-hydroperoxypropane-1,2,3-tricarboxylic acid)

SMILES for NP0313686 (2-hydroperoxypropane-1,2,3-tricarboxylic acid)

INCHI for NP0313686 (2-hydroperoxypropane-1,2,3-tricarboxylic acid)

Structure for NP0313686 (2-hydroperoxypropane-1,2,3-tricarboxylic acid)

3D Structure for NP0313686 (2-hydroperoxypropane-1,2,3-tricarboxylic acid)