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Showing metabocard for cis-Aconitic anhydride (HMDB0250284)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 07:17:15 UTC
Update Date2021-09-26 23:01:39 UTC
HMDB IDHMDB0250284
Secondary Accession NumbersNone
Metabolite Identification
Common Namecis-Aconitic anhydride
Description2-(2,5-dioxo-2,5-dihydrofuran-3-yl)acetic 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-(2,5-dioxo-2,5-dihydrofuran-3-yl)acetic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Cis-aconitic anhydride is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically cis-Aconitic anhydride is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0250284 (cis-Aconitic anhydride)


  Mrv1652309112109172D          

 11 11  0  0  0  0            999 V2000
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145   -2.2438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3091   -1.6626    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  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
M  END
Download

3D MOL for HMDB0250284 (cis-Aconitic anhydride)

HMDB0250284
     RDKit          3D
cis-Aconitic anhydride
 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.2536   -0.8486    1.0154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9446   -0.0516    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5202    1.1857    0.0283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9336   -0.4436   -0.8695 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3946   -0.2732   -0.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3404    0.5144   -0.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4823    0.4143    0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5527    1.0506    0.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1362   -0.4957    1.2313 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8472   -0.9490    0.9814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1862   -1.7766    1.6451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5203    1.8068    0.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0703   -1.4984   -1.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9956    0.2156   -1.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2986    1.1493   -1.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10  5  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  6 15  1  0
M  END
Download

3D SDF for HMDB0250284 (cis-Aconitic anhydride)


  Mrv1652309112109172D          

 11 11  0  0  0  0            999 V2000
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145   -2.2438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3091   -1.6626    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  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
M  END
> <DATABASE_ID>
HMDB0250284

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CC1=CC(=O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H4O5/c7-4(8)1-3-2-5(9)11-6(3)10/h2H,1H2,(H,7,8)

> <INCHI_KEY>
GVJRTUUUJYMTNQ-UHFFFAOYSA-N

> <FORMULA>
C6H4O5

> <MOLECULAR_WEIGHT>
156.093

> <EXACT_MASS>
156.005873229

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
12.520955522634688

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(2,5-dioxo-2,5-dihydrofuran-3-yl)acetic acid

> <ALOGPS_LOGP>
0.34

> <JCHEM_LOGP>
0.07980173500000007

> <ALOGPS_LOGS>
-0.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4763562274383117

> <JCHEM_PKA_STRONGEST_BASIC>
-6.815901632762225

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
32.0251

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.01e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2,5-dioxofuran-3-yl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0250284 (cis-Aconitic anhydride)

HMDB0250284
     RDKit          3D
cis-Aconitic anhydride
 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.2536   -0.8486    1.0154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9446   -0.0516    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5202    1.1857    0.0283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9336   -0.4436   -0.8695 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3946   -0.2732   -0.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3404    0.5144   -0.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4823    0.4143    0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5527    1.0506    0.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1362   -0.4957    1.2313 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8472   -0.9490    0.9814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1862   -1.7766    1.6451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5203    1.8068    0.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0703   -1.4984   -1.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9956    0.2156   -1.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2986    1.1493   -1.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10  5  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  6 15  1  0
M  END
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PDB for HMDB0250284 (cis-Aconitic anhydride)

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.109  -2.943   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.014  -4.188   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.577  -3.104   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    2    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0250284 (cis-Aconitic anhydride)

COMPND    HMDB0250284
HETATM    1  O1  UNL     1      -2.254  -0.849   1.015  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.945  -0.052   0.120  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.520   1.186   0.028  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.934  -0.444  -0.869  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.395  -0.273  -0.217  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.340   0.514  -0.640  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.482   0.414   0.249  1.00  0.00           C  
HETATM    8  O3  UNL     1       3.553   1.051   0.111  1.00  0.00           O  
HETATM    9  O4  UNL     1       2.136  -0.496   1.231  1.00  0.00           O  
HETATM   10  C6  UNL     1       0.847  -0.949   0.981  1.00  0.00           C  
HETATM   11  O5  UNL     1       0.186  -1.777   1.645  1.00  0.00           O  
HETATM   12  H1  UNL     1      -2.520   1.807   0.824  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.070  -1.498  -1.186  1.00  0.00           H  
HETATM   14  H3  UNL     1      -0.996   0.216  -1.781  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.299   1.149  -1.513  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5   13   14
CONECT    5    6    6   10
CONECT    6    7   15
CONECT    7    8    8    9
CONECT    9   10
CONECT   10   11   11
END
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SMILES for HMDB0250284 (cis-Aconitic anhydride)

OC(=O)CC1=CC(=O)OC1=O
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INCHI for HMDB0250284 (cis-Aconitic anhydride)

InChI=1S/C6H4O5/c7-4(8)1-3-2-5(9)11-6(3)10/h2H,1H2,(H,7,8)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-(2,5-Dioxo-2,5-dihydrofuran-3-yl)acetateGenerator
Aconitic anhydrideMeSH
Chemical FormulaC6H4O5
Average Molecular Weight156.093
Monoisotopic Molecular Weight156.005873229
IUPAC Name2-(2,5-dioxo-2,5-dihydrofuran-3-yl)acetic acid
Traditional Name(2,5-dioxofuran-3-yl)acetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CC1=CC(=O)OC1=O
InChI Identifier
InChI=1S/C6H4O5/c7-4(8)1-3-2-5(9)11-6(3)10/h2H,1H2,(H,7,8)
InChI KeyGVJRTUUUJYMTNQ-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • 2-furanone
  • Dihydrofuran
  • Carboxylic acid anhydride
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological location
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP0.34ALOGPS
logP0.08ChemAxon
logS-0.59ALOGPS
pKa (Strongest Acidic)3.48ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.03 m³·mol⁻¹ChemAxon
Polarizability12.52 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+122.09730932474
DeepCCS[M-H]-118.26230932474
DeepCCS[M-2H]-155.36930932474
DeepCCS[M+Na]+130.76630932474
AllCCS[M+H]+132.332859911
AllCCS[M+H-H2O]+127.832859911
AllCCS[M+NH4]+136.432859911
AllCCS[M+Na]+137.632859911
AllCCS[M-H]-126.432859911
AllCCS[M+Na-2H]-127.632859911
AllCCS[M+HCOO]-129.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
cis-Aconitic anhydrideOC(=O)CC1=CC(=O)OC1=O2612.8Standard polar33892256
cis-Aconitic anhydrideOC(=O)CC1=CC(=O)OC1=O1364.1Standard non polar33892256
cis-Aconitic anhydrideOC(=O)CC1=CC(=O)OC1=O1395.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - cis-Aconitic anhydride GC-MS (Non-derivatized) - 70eV, Positivesplash10-08gi-9700000000-98819132cac40948ea802021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-Aconitic anhydride GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-Aconitic anhydride GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-Aconitic anhydride GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Aconitic anhydride 10V, Positive-QTOFsplash10-03dr-1900000000-e9fcf38bae32057fb4e72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Aconitic anhydride 20V, Positive-QTOFsplash10-03xr-9800000000-19f4188feb125f2fc3512021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Aconitic anhydride 40V, Positive-QTOFsplash10-014v-9000000000-3035751de25aa89cf1632021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Aconitic anhydride 10V, Negative-QTOFsplash10-03di-0900000000-fb8d24398e2c2b4c8c772021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Aconitic anhydride 20V, Negative-QTOFsplash10-03di-1900000000-164cae01aead7649fd772021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Aconitic anhydride 40V, Negative-QTOFsplash10-014l-9000000000-a279383c783dbefdb04a2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID58668
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]