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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 11:10:15 UTC

Update Date

2021-09-24 11:10:15 UTC

HMDB ID

HMDB0304619

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1,5-Dimethyl citrate

Description

2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Based on a literature review very few articles have been published on 2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1652309272007352D          

 15 14  0  0  0  0            999 V2000
 2500.0020 2500.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7169 2500.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4318 2500.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1468 2500.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.8617 2500.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4318 2499.5882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2871 2500.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5722 2500.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8552 2500.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.1382 2500.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5722 2499.5882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0020 2499.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7169 2499.1744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2871 2499.1744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0020 2501.2387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  2  0  0  0  0
  4  5  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  2  0  0  0  0
  9 10  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  1 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0304619

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H12O7/c1-14-5(9)3-8(13,7(11)12)4-6(10)15-2/h13H,3-4H2,1-2H3,(H,11,12)

> <INCHI_KEY>
XLYPVOJLUJUWKA-UHFFFAOYSA-N

> <FORMULA>
C8H12O7

> <MOLECULAR_WEIGHT>
220.177

> <EXACT_MASS>
220.058302726

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.55718543871535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid

> <ALOGPS_LOGP>
-0.68

> <JCHEM_LOGP>
-1.03089934

> <ALOGPS_LOGS>
-0.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.347594523707244

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3240097428133266

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1860065322612074

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
45.1621

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.56e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    4666.6704667.439   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4668.0054668.208   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    4669.3394667.439   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    4670.6744668.208   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    4672.0094667.439   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    4669.3394665.898   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    4665.3364668.208   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    4664.0014667.439   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    4662.6634668.208   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    4661.3254667.435   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    4664.0014665.898   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    4666.6704665.898   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    4668.0054665.126   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    4665.3364665.126   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    4666.6704668.979   0.000  0.00  0.00           O+0
CONECT    1    2    7   12   15                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8                                                            
CONECT   12    1   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    1                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0304619
HETATM    1  C1  UNL     1      -3.586   1.796   0.295  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.441   0.981   0.143  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.566   1.244  -0.886  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.787   2.197  -1.677  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.336   0.451  -1.135  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.159  -0.663  -0.143  1.00  0.00           C  
HETATM    7  O3  UNL     1      -0.069  -0.194   1.156  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.125  -1.392  -0.509  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.314  -0.540  -0.470  1.00  0.00           C  
HETATM   10  O4  UNL     1       2.603   0.216  -1.425  1.00  0.00           O  
HETATM   11  O5  UNL     1       3.151  -0.551   0.629  1.00  0.00           O  
HETATM   12  C7  UNL     1       4.296   0.281   0.647  1.00  0.00           C  
HETATM   13  C8  UNL     1      -1.255  -1.660  -0.206  1.00  0.00           C  
HETATM   14  O6  UNL     1      -1.558  -2.253  -1.287  1.00  0.00           O  
HETATM   15  O7  UNL     1      -2.013  -2.001   0.909  1.00  0.00           O  
HETATM   16  H1  UNL     1      -4.325   1.356   0.990  1.00  0.00           H  
HETATM   17  H2  UNL     1      -4.027   2.083  -0.680  1.00  0.00           H  
HETATM   18  H3  UNL     1      -3.231   2.745   0.762  1.00  0.00           H  
HETATM   19  H4  UNL     1      -0.393   0.035  -2.143  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.516   1.157  -0.982  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.350  -0.936   1.754  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.235  -2.316   0.124  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.033  -1.792  -1.556  1.00  0.00           H  
HETATM   24  H9  UNL     1       5.172  -0.261   0.295  1.00  0.00           H  
HETATM   25  H10 UNL     1       4.146   1.173  -0.021  1.00  0.00           H  
HETATM   26  H11 UNL     1       4.514   0.658   1.664  1.00  0.00           H  
HETATM   27  H12 UNL     1      -3.009  -1.815   0.942  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   19   20
CONECT    6    7    8   13
CONECT    7   21
CONECT    8    9   22   23
CONECT    9   10   10   11
CONECT   11   12
CONECT   12   24   25   26
CONECT   13   14   14   15
CONECT   15   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoate	Generator
1,5-Dimethyl citric acid	Generator
sym-Dimethyl citrate	PhytoBank
alpha,alpha'-Dimethyl citrate	PhytoBank
α,α'-Dimethyl citrate	PhytoBank
α,α’-Dimethyl citrate	PhytoBank
2-Hydroxy-1,2,3-propanetricarboxylic acid-1,3-dimethylester	PhytoBank
2-Hydroxy-1,2,3-propanetricarboxylic acid 1,3-dimethyl ester	PhytoBank

Chemical Formula

C₈H₁₂O₇

Average Molecular Weight

220.177

Monoisotopic Molecular Weight

220.058302726

IUPAC Name

2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid

Traditional Name

2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H12O7/c1-14-5(9)3-8(13,7(11)12)4-6(10)15-2/h13H,3-4H2,1-2H3,(H,11,12)

InChI Key

XLYPVOJLUJUWKA-UHFFFAOYSA-N

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

Ontology

Not Available

Exogenous (HMDB: HMDB0304619)

Food

Fruit

Tropical fruit

Mundu (FooDB: FOOD00897)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.68	ALOGPS
logP	-1	ChemAxon
logS	-0.15	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	45.16 m³·mol⁻¹	ChemAxon
Polarizability	19.56 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	148.526	32859911
AllCCS	[M+H-H2O]+	145.014	32859911
AllCCS	[M+Na]+	152.725	32859911
AllCCS	[M+NH4]+	151.787	32859911
AllCCS	[M-H]-	145.125	32859911
AllCCS	[M+Na-2H]-	146.079	32859911
AllCCS	[M+HCOO]-	147.209	32859911
DeepCCS	[M+H]+	141.905	30932474
DeepCCS	[M-H]-	139.086	30932474
DeepCCS	[M-2H]-	175.318	30932474
DeepCCS	[M+Na]+	150.857	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dimethyl citrate 10V, Positive-QTOF	splash10-0fms-0930000000-243177cbaa847381c688	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dimethyl citrate 20V, Positive-QTOF	splash10-00fr-9810000000-35622dc254d894e4710f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dimethyl citrate 40V, Positive-QTOF	splash10-0q4l-6900000000-57f691182be3f5835a31	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dimethyl citrate 10V, Negative-QTOF	splash10-016s-0920000000-ab70836ad1c46318de65	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dimethyl citrate 20V, Negative-QTOF	splash10-0104-2900000000-0e57b791a10481a6204c	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dimethyl citrate 40V, Negative-QTOF	splash10-0006-9700000000-6ceafbee7a146b71d63e	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dimethyl citrate 10V, Positive-QTOF	splash10-00dr-0970000000-790d38073d51d698ec46	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dimethyl citrate 20V, Positive-QTOF	splash10-0fna-7920000000-80fc0bd90acd55eed131	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dimethyl citrate 40V, Positive-QTOF	splash10-0a4i-9000000000-88493d461cc1202781ac	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dimethyl citrate 10V, Negative-QTOF	splash10-0171-0910000000-6e7bec151771ff3c6b73	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dimethyl citrate 20V, Negative-QTOF	splash10-014r-2900000000-5de46111bcde1085d178	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dimethyl citrate 40V, Negative-QTOF	splash10-0006-9100000000-ae7da29235230e055dc0	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB093570

KNApSAcK ID

Not Available

Chemspider ID

10466767

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12566214

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 1,5-Dimethyl citrate (HMDB0304619)

MOL for HMDB0304619 (1,5-Dimethyl citrate)

3D MOL for HMDB0304619 (1,5-Dimethyl citrate)

3D SDF for HMDB0304619 (1,5-Dimethyl citrate)

3D-SDF for HMDB0304619 (1,5-Dimethyl citrate)

PDB for HMDB0304619 (1,5-Dimethyl citrate)

3D PDB for HMDB0304619 (1,5-Dimethyl citrate)

SMILES for HMDB0304619 (1,5-Dimethyl citrate)

INCHI for HMDB0304619 (1,5-Dimethyl citrate)

Structure for HMDB0304619 (1,5-Dimethyl citrate)

3D Structure for HMDB0304619 (1,5-Dimethyl citrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra