NP-MRD: Showing NP-Card for 2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid (NP0306693)

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Record Information

Version

2.0

Created at

2022-09-10 23:20:01 UTC

Updated at

2022-09-10 23:20:01 UTC

NP-MRD ID

NP0306693

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid

Description

Methyl citrate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. 2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid is found in Opuntia ficus-indica. 2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid was first documented in 2021 (PMID: 34560108). Based on a literature review a small amount of articles have been published on methyl citrate (PMID: 35944020) (PMID: 35903162) (PMID: 35718051).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112201202D          

 14 13  0  0  0  0            999 V2000
   -0.9059   -1.9520    0.0000 C   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
    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
    0.5230   -1.1270    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
    1.6500   -1.4289    0.0000 O   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
    2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -1.5395    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  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306693

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H10O7/c1-14-5(10)3-7(13,6(11)12)2-4(8)9/h13H,2-3H2,1H3,(H,8,9)(H,11,12)

> <INCHI_KEY>
YUTUUOJFXIMELV-UHFFFAOYSA-N

> <FORMULA>
C7H10O7

> <MOLECULAR_WEIGHT>
206.15

> <EXACT_MASS>
206.042652662

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.531320542442216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid

> <JCHEM_LOGP>
-1.1767933959999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.105480776124731

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.195052809198466

> <JCHEM_PKA_STRONGEST_BASIC>
-4.185849991248765

> <JCHEM_POLAR_SURFACE_AREA>
121.13

> <JCHEM_REFRACTIVITY>
40.39300000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic 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  C   UNK     0      -1.691  -3.644   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.357  -4.414   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.976  -3.644   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.310  -4.414   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.976  -2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.080  -2.667   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.977  -1.334   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.311  -0.564   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.977  -2.874   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                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8   12                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    6   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
Methyl citric acid	Generator

Chemical Formula

C₇H₁₀O₇

Average Mass

206.1500 Da

Monoisotopic Mass

206.04265 Da

IUPAC Name

2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid

Traditional Name

2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid

CAS Registry Number

Not Available

SMILES

COC(=O)CC(O)(CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C7H10O7/c1-14-5(10)3-7(13,6(11)12)2-4(8)9/h13H,2-3H2,1H3,(H,8,9)(H,11,12)

InChI Key

YUTUUOJFXIMELV-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
Opuntia ficus-indica	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
Fatty acid ester
Fatty acid methyl ester
Alpha-hydroxy acid
Hydroxy acid
Fatty acyl
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	-1.2	ChemAxon
pKa (Strongest Acidic)	3.2	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	40.39 m³·mol⁻¹	ChemAxon
Polarizability	17.53 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00040564

Chemspider ID

335421

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

378532

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nikitushkin V, Shleeva M, Loginov D, Dycka F F, Sterba J, Kaprelyants A: Shotgun proteomic profiling of dormant, 'non-culturable' Mycobacterium tuberculosis. PLoS One. 2022 Aug 9;17(8):e0269847. doi: 10.1371/journal.pone.0269847. eCollection 2022. [PubMed:35944020 ]
Xu B, Zhang L, Chen Q, Wang Y, Peng Y, Tang H: Case Report: A Case of Late-Onset Combined Methylmalonic Acidemia and Hyperhomocysteinemia Induced by a Vegetarian Diet. Front Pediatr. 2022 Jul 12;10:896177. doi: 10.3389/fped.2022.896177. eCollection 2022. [PubMed:35903162 ]
Liu Z, Peng Y, Zhao L, Li X: MFE40-the active fraction of Mume Fructus alcohol extract-alleviates Crohn's disease and its complications. J Ethnopharmacol. 2022 Oct 5;296:115465. doi: 10.1016/j.jep.2022.115465. Epub 2022 Jun 17. [PubMed:35718051 ]
Bashir A, Sun Y, Yu X, Sun X, Li L: Nematicidal effects of 2-methyl-aconitate isomerase from the phytopathogen Pseudomonas syringae MB03 on the model nematode Caenorhabditis elegans. J Invertebr Pathol. 2021 Oct;185:107669. doi: 10.1016/j.jip.2021.107669. Epub 2021 Sep 22. [PubMed:34560108 ]
LOTUS database [Link]

Showing NP-Card for 2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid (NP0306693)

MOL for NP0306693 (2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid)

3D MOL for NP0306693 (2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid)

3D SDF for NP0306693 (2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid)

3D-SDF for NP0306693 (2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid)

PDB for NP0306693 (2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid)

3D PDB for NP0306693 (2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid)

SMILES for NP0306693 (2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid)

INCHI for NP0306693 (2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid)

Structure for NP0306693 (2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid)

3D Structure for NP0306693 (2-hydroxy-2-(2-methoxy-2-oxoethyl)butanedioic acid)