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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-03-04 20:35:59 UTC

Update Date

2021-09-14 15:47:54 UTC

HMDB ID

HMDB0059808

Secondary Accession Numbers

HMDB59808

Metabolite Identification

Common Name

Acetyl citrate

Description

Acetyl citrate belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Based on a literature review a significant number of articles have been published on Acetyl citrate.

Structure

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


  Mrv1652305171806302D          

 16 15  0  0  0  0            999 V2000
   -1.6204   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059   -1.1270    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
    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
    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
    2.6664   -1.5395    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  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 11  1  0  0  0  0
 16 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059808

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O8/c1-4(9)16-6(12)3-8(15,7(13)14)2-5(10)11/h15H,2-3H2,1H3,(H,10,11)(H,13,14)

> <INCHI_KEY>
WWXUGNUFCNYMFK-UHFFFAOYSA-N

> <FORMULA>
C8H10O8

> <MOLECULAR_WEIGHT>
234.16

> <EXACT_MASS>
234.037567282

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.68608786453739

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[2-(acetyloxy)-2-oxoethyl]-2-hydroxybutanedioic acid

> <ALOGPS_LOGP>
-1.00

> <JCHEM_LOGP>
-1.4118611559999996

> <ALOGPS_LOGS>
-0.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.986992148720168

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.092890992370602

> <JCHEM_PKA_STRONGEST_BASIC>
-4.186234248793244

> <JCHEM_POLAR_SURFACE_AREA>
138.20000000000002

> <JCHEM_REFRACTIVITY>
45.062200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.23e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[2-(acetyloxy)-2-oxoethyl]-2-hydroxybutanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  C   UNK     0      -3.025  -4.414   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.691  -3.644   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.691  -2.104   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.357  -4.414   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.976  -3.644   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.310  -4.414   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.976  -2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.080  -2.667   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.977  -1.334   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.311  -0.564   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.310   1.334   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.977  -2.874   0.000  0.00  0.00           O+0
HETATM   16  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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   13                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11                                                            
CONECT   13    8   14   16                                                  
CONECT   14   13                                                            
CONECT   15   11                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Acetyl citric acid	Generator
2-[2-(Acetyloxy)-2-oxoethyl]-2-hydroxybutanedioate	HMDB

Chemical Formula

C₈H₁₀O₈

Average Molecular Weight

234.16

Monoisotopic Molecular Weight

234.037567282

IUPAC Name

2-[2-(acetyloxy)-2-oxoethyl]-2-hydroxybutanedioic acid

Traditional Name

2-[2-(acetyloxy)-2-oxoethyl]-2-hydroxybutanedioic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H10O8/c1-4(9)16-6(12)3-8(15,7(13)14)2-5(10)11/h15H,2-3H2,1H3,(H,10,11)(H,13,14)

InChI Key

WWXUGNUFCNYMFK-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Hydroxy acid
Alpha-hydroxy acid
Tertiary alcohol
Carboxylic acid anhydride
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 22624806)

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
Water Solubility	19.1 g/L	ALOGPS
logP	-1	ALOGPS
logP	-1.4	ChemAxon
logS	-0.51	ALOGPS
pKa (Strongest Acidic)	3.09	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	138.2 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	45.06 m³·mol⁻¹	ChemAxon
Polarizability	19.69 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
DarkChem	[M+H]+	152.557	31661259
DarkChem	[M-H]-	148.407	31661259
DeepCCS	[M+H]+	142.539	30932474
DeepCCS	[M-H]-	140.144	30932474
DeepCCS	[M-2H]-	174.419	30932474
DeepCCS	[M+Na]+	148.987	30932474
AllCCS	[M+H]+	149.4	32859911
AllCCS	[M+H-H2O]+	146.0	32859911
AllCCS	[M+NH4]+	152.6	32859911
AllCCS	[M+Na]+	153.5	32859911
AllCCS	[M-H]-	145.5	32859911
AllCCS	[M+Na-2H]-	146.1	32859911
AllCCS	[M+HCOO]-	146.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acetyl citrate	CC(=O)OC(=O)CC(O)(CC(O)=O)C(O)=O	3108.7	Standard polar	33892256
Acetyl citrate	CC(=O)OC(=O)CC(O)(CC(O)=O)C(O)=O	1420.2	Standard non polar	33892256
Acetyl citrate	CC(=O)OC(=O)CC(O)(CC(O)=O)C(O)=O	1831.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Acetyl citrate,1TMS,isomer #1	CC(=O)OC(=O)CC(CC(=O)O)(O[Si](C)(C)C)C(=O)O	1761.3	Semi standard non polar	33892256
Acetyl citrate,1TMS,isomer #2	CC(=O)OC(=O)CC(O)(CC(=O)O[Si](C)(C)C)C(=O)O	1724.1	Semi standard non polar	33892256
Acetyl citrate,1TMS,isomer #3	CC(=O)OC(=O)CC(O)(CC(=O)O)C(=O)O[Si](C)(C)C	1679.1	Semi standard non polar	33892256
Acetyl citrate,2TMS,isomer #1	CC(=O)OC(=O)CC(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O	1794.9	Semi standard non polar	33892256
Acetyl citrate,2TMS,isomer #2	CC(=O)OC(=O)CC(CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1784.8	Semi standard non polar	33892256
Acetyl citrate,2TMS,isomer #3	CC(=O)OC(=O)CC(O)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1768.4	Semi standard non polar	33892256
Acetyl citrate,3TMS,isomer #1	CC(=O)OC(=O)CC(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1876.8	Semi standard non polar	33892256
Acetyl citrate,1TBDMS,isomer #1	CC(=O)OC(=O)CC(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O	1987.8	Semi standard non polar	33892256
Acetyl citrate,1TBDMS,isomer #2	CC(=O)OC(=O)CC(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	1962.4	Semi standard non polar	33892256
Acetyl citrate,1TBDMS,isomer #3	CC(=O)OC(=O)CC(O)(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	1945.4	Semi standard non polar	33892256
Acetyl citrate,2TBDMS,isomer #1	CC(=O)OC(=O)CC(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O	2254.3	Semi standard non polar	33892256
Acetyl citrate,2TBDMS,isomer #2	CC(=O)OC(=O)CC(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2229.4	Semi standard non polar	33892256
Acetyl citrate,2TBDMS,isomer #3	CC(=O)OC(=O)CC(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2226.9	Semi standard non polar	33892256
Acetyl citrate,3TBDMS,isomer #1	CC(=O)OC(=O)CC(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2496.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Acetyl citrate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl citrate 10V, Positive-QTOF	splash10-0170-0920000000-7567fd17430dd029d731	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl citrate 20V, Positive-QTOF	splash10-0zi0-4900000000-ab3e4d09833ec463ae2b	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl citrate 40V, Positive-QTOF	splash10-0573-8900000000-21b4ccdf82a0a1826420	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl citrate 10V, Negative-QTOF	splash10-00el-4910000000-1b5e60837b715e3034cb	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl citrate 20V, Negative-QTOF	splash10-0a4i-8900000000-5c582058c2a59dd5d89d	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl citrate 40V, Negative-QTOF	splash10-0a4l-9300000000-4682f667d2f4c8234c7b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl citrate 10V, Positive-QTOF	splash10-016s-1950000000-bf4b16c0266f7990de25	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl citrate 20V, Positive-QTOF	splash10-052f-9200000000-579a650509f00d5c546d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl citrate 40V, Positive-QTOF	splash10-0006-9000000000-bc4d06b8b59a03b2af5c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl citrate 10V, Negative-QTOF	splash10-00b9-1900000000-fe52b213995f06cfddd5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl citrate 20V, Negative-QTOF	splash10-004i-3900000000-bd73bc8dd50d8227ac72	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyl citrate 40V, Negative-QTOF	splash10-0a4i-9000000000-200e9366e2e327119b75	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Not Available	22624806	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

67159455

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54454045

PDB ID

Not Available

ChEBI ID

89658

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 Acetyl citrate (HMDB0059808)

MOL for HMDB0059808 (Acetyl citrate)

3D MOL for HMDB0059808 (Acetyl citrate)

3D SDF for HMDB0059808 (Acetyl citrate)

3D-SDF for HMDB0059808 (Acetyl citrate)

PDB for HMDB0059808 (Acetyl citrate)

3D PDB for HMDB0059808 (Acetyl citrate)

SMILES for HMDB0059808 (Acetyl citrate)

INCHI for HMDB0059808 (Acetyl citrate)

Structure for HMDB0059808 (Acetyl citrate)

3D Structure for HMDB0059808 (Acetyl citrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra