NP-MRD: Showing NP-Card for Hydroxycitric acid (NP0137512)

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Record Information

Version

2.0

Created at

2022-05-30 16:54:40 UTC

Updated at

2022-05-30 16:54:40 UTC

NP-MRD ID

NP0137512

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hydroxycitric acid

Description

Garcinia acid, also known as D-erythro-form or hydroxycitrate, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Garcinia acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Garcinia acid has been detected, but not quantified in, fruits and herbs and spices. Hydroxycitric acid is found in Garcinia atroviridis, Garcinia cowa and Garcinia oblongifolia. Hydroxycitric acid was first documented in 2010 (PMID: 20946014). This could make garcinia acid a potential biomarker for the consumption of these foods (PMID: 22530711).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061305462D          

 14 13  0  0  0  0            999 V2000
    2.2539    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   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
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  6  1  1  0  0  0  0
  6  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  2  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 11  4  1  0  0  0  0
 12  5  2  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137512

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O8/c7-2(8)1-6(14,5(12)13)3(9)4(10)11/h3,9,14H,1H2,(H,7,8)(H,10,11)(H,12,13)

> <INCHI_KEY>
ZMJBYMUCKBYSCP-UHFFFAOYSA-N

> <FORMULA>
C6H8O8

> <MOLECULAR_WEIGHT>
208.1229

> <EXACT_MASS>
208.021917232

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
16.080047328139727

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.48

> <JCHEM_LOGP>
-2.0378459126666666

> <ALOGPS_LOGS>
-0.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.292763735963212

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.902830181464747

> <JCHEM_PKA_STRONGEST_BASIC>
-4.402972071364544

> <JCHEM_POLAR_SURFACE_AREA>
152.35999999999999

> <JCHEM_REFRACTIVITY>
36.9621

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.97e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxycitric 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       4.207   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.207   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.874   3.850   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.541   3.850   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.874  -1.897   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.954   0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       5.954  -1.897   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.540  -1.540   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.206   0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    7    8                                                  
CONECT    3    4    6    9                                                  
CONECT    4    3   10   11                                                  
CONECT    5    6   12   13                                                  
CONECT    6    1    3    5   14                                             
CONECT    7    2                                                            
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    4                                                            
CONECT   12    5                                                            
CONECT   13    5                                                            
CONECT   14    6                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
(-)-Hydroxycitric acid	HMDB
(1S,2S)-1,2-Dihydroxypropane-1,2,3-tricarboxylic acid	HMDB
1,2-Dihydroxy-1,2,3-propanetricarboxylic acid, 8ci	HMDB
D-Erythro-form	HMDB
Hydroxycitrate	HMDB
Hydroxycitric acid	HMDB
Super citrimax hca 600SXS	HMDB
1,2-Dihydroxypropane-1,2,3-tricarboxylate	Generator
HAES CPD	MeSH
Hydroxycitric acid, trisodium salt, (erythro-(+-))-isomer	MeSH
Hydroxycitric acid, sodium salt	MeSH
Hydroxycitric acid, threo-(D)-isomer	MeSH
Hydroxycitric acid, threo-(L)-isomer	MeSH
(+)-Allohydroxycitric acid	MeSH
Allo-2-hydroxycitric acid	MeSH
Garcinia acid	MeSH
Hibiscus acid	MeSH
Hydroxycitric acid ethylenediamine salt	MeSH
Hydroxycitric acid, erythro-(D)-isomer	MeSH
Hydroxycitric acid, trisodium salt	MeSH

Chemical Formula

C₆H₈O₈

Average Mass

208.1229 Da

Monoisotopic Mass

208.02192 Da

IUPAC Name

1,2-dihydroxypropane-1,2,3-tricarboxylic acid

Traditional Name

hydroxycitric acid

CAS Registry Number

Not Available

SMILES

OC(C(O)=O)C(O)(CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C6H8O8/c7-2(8)1-6(14,5(12)13)3(9)4(10)11/h3,9,14H,1H2,(H,7,8)(H,10,11)(H,12,13)

InChI Key

ZMJBYMUCKBYSCP-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 atroviridis	LOTUS Database	35616633
Garcinia cowa	LOTUS Database	35616633
Garcinia oblongifolia	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
Beta-hydroxy acid
Monosaccharide
Hydroxy acid
Alpha-hydroxy acid
Tertiary alcohol
Secondary alcohol
1,2-diol
Carboxylic acid
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Alcohol
Organic oxide
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
logP	-1.5	ALOGPS
logP	-2	ChemAxon
logS	-0.02	ALOGPS
pKa (Strongest Acidic)	2.9	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	152.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	36.96 m³·mol⁻¹	ChemAxon
Polarizability	16.08 Å³	ChemAxon
Number of Rings	0	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

HMDB0031159

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003174

KNApSAcK ID

Not Available

Chemspider ID

110439

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

123908

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Stohs SJ, Lau FC, Kim D, Kim SU, Bagchi M, Bagchi D: Safety assessment of a calcium-potassium salt of (-)-hydroxycitric acid. Toxicol Mech Methods. 2010 Nov;20(9):515-25. doi: 10.3109/15376516.2010.521207. Epub 2010 Oct 14. [PubMed:20946014 ]
Marquez F, Babio N, Bullo M, Salas-Salvado J: Evaluation of the safety and efficacy of hydroxycitric acid or Garcinia cambogia extracts in humans. Crit Rev Food Sci Nutr. 2012;52(7):585-94. doi: 10.1080/10408398.2010.500551. [PubMed:22530711 ]

Showing NP-Card for Hydroxycitric acid (NP0137512)

MOL for NP0137512 (Hydroxycitric acid)

3D MOL for NP0137512 (Hydroxycitric acid)

3D SDF for NP0137512 (Hydroxycitric acid)

3D-SDF for NP0137512 (Hydroxycitric acid)

PDB for NP0137512 (Hydroxycitric acid)

3D PDB for NP0137512 (Hydroxycitric acid)

SMILES for NP0137512 (Hydroxycitric acid)

INCHI for NP0137512 (Hydroxycitric acid)

Structure for NP0137512 (Hydroxycitric acid)

3D Structure for NP0137512 (Hydroxycitric acid)