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Showing metabocard for Maleic Anhydride (HMDB0254311)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 13:32:37 UTC
Update Date2022-11-23 22:29:16 UTC
HMDB IDHMDB0254311
Secondary Accession NumbersNone
Metabolite Identification
Common NameMaleic Anhydride
Descriptionmaleic anhydride, also known as MA or 2,5-furandione, belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. Based on a literature review a significant number of articles have been published on maleic anhydride. This compound has been identified in human blood as reported by (PMID: 31557052 ). Maleic anhydride is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Maleic 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 HMDB0254311 (Maleic Anhydride)


  Mrv1572004191601122D          

  7  7  0  0  0  0            999 V2000
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    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
    0.5678    1.1143    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
    0.5678    1.9393    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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
M  END
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3D MOL for HMDB0254311 (Maleic Anhydride)

HMDB0254311
     RDKit          3D
MALEIC ANHYDRIDE
  9  9  0  0  0  0  0  0  0  0999 V2000
    2.3560   -0.9686   -0.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1346   -0.6184   -0.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6451    0.7526   -0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6742    0.7372    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1220   -0.6477    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3171   -1.0243    0.0345 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0123   -1.4426    0.0074 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2787    1.6112   -0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3134    1.6006    0.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  2  1  0
  3  8  1  0
  4  9  1  0
M  END
Download

3D SDF for HMDB0254311 (Maleic Anhydride)


  Mrv1572004191601122D          

  7  7  0  0  0  0            999 V2000
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    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
    0.5678    1.1143    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
    0.5678    1.9393    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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254311

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1OC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C4H2O3/c5-3-1-2-4(6)7-3/h1-2H

> <INCHI_KEY>
FPYJFEHAWHCUMM-UHFFFAOYSA-N

> <FORMULA>
C4H2O3

> <MOLECULAR_WEIGHT>
98.057

> <EXACT_MASS>
98.000393924

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
7.601050931430145

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5-dihydrofuran-2,5-dione

> <ALOGPS_LOGP>
0.02

> <JCHEM_LOGP>
0.5599243456666666

> <ALOGPS_LOGS>
0.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.766159836707996

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
21.401600000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
maleic anhydride

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0254311 (Maleic Anhydride)

HMDB0254311
     RDKit          3D
MALEIC ANHYDRIDE
  9  9  0  0  0  0  0  0  0  0999 V2000
    2.3560   -0.9686   -0.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1346   -0.6184   -0.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6451    0.7526   -0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6742    0.7372    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1220   -0.6477    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3171   -1.0243    0.0345 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0123   -1.4426    0.0074 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2787    1.6112   -0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3134    1.6006    0.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  2  1  0
  3  8  1  0
  4  9  1  0
M  END
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PDB for HMDB0254311 (Maleic Anhydride)

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.306   1.175   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  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5    7                                                  
CONECT    4    2    6    7                                                  
CONECT    5    3                                                            
CONECT    6    4                                                            
CONECT    7    3    4                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END
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3D PDB for HMDB0254311 (Maleic Anhydride)

COMPND    HMDB0254311
HETATM    1  O1  UNL     1       2.356  -0.969  -0.025  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.135  -0.618  -0.011  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.645   0.753  -0.012  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.674   0.737   0.005  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.122  -0.648   0.018  1.00  0.00           C  
HETATM    6  O2  UNL     1      -2.317  -1.024   0.035  1.00  0.00           O  
HETATM    7  O3  UNL     1       0.012  -1.443   0.007  1.00  0.00           O  
HETATM    8  H1  UNL     1       1.279   1.611  -0.024  1.00  0.00           H  
HETATM    9  H2  UNL     1      -1.313   1.601   0.008  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    7
CONECT    3    4    4    8
CONECT    4    5    9
CONECT    5    6    6    7
END
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SMILES for HMDB0254311 (Maleic Anhydride)

O=C1OC(=O)C=C1
Download

INCHI for HMDB0254311 (Maleic Anhydride)

InChI=1S/C4H2O3/c5-3-1-2-4(6)7-3/h1-2H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2,5-FurandioneChEBI
cis-Butenedioic anhydrideChEBI
Dihydro-2,5-dioxofuranChEBI
MAChEBI
Maleic acid anhydrideChEBI
Toxilic anhydrideChEBI
Maleate anhydrideGenerator
2,5 FurandionesMeSH
2,5-FurandionesMeSH
Anhydride, maleicMeSH
Anhydrides, maleicMeSH
Maleic anhydrideMeSH
Maleic anhydridesMeSH
Chemical FormulaC4H2O3
Average Molecular Weight98.057
Monoisotopic Molecular Weight98.000393924
IUPAC Name2,5-dihydrofuran-2,5-dione
Traditional Namemaleic anhydride
CAS Registry NumberNot Available
SMILES
O=C1OC(=O)C=C1
InChI Identifier
InChI=1S/C4H2O3/c5-3-1-2-4(6)7-3/h1-2H
InChI KeyFPYJFEHAWHCUMM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentButenolides
Alternative Parents
Substituents
  • Dicarboxylic acid or derivatives
  • 2-furanone
  • Carboxylic acid anhydride
  • Oxacycle
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
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
logP0.02ALOGPS
logP0.56ChemAxon
logS0.12ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity21.4 m³·mol⁻¹ChemAxon
Polarizability7.6 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]+118.28330932474
DeepCCS[M-H]-115.32430932474
DeepCCS[M-2H]-152.01530932474
DeepCCS[M+Na]+126.82630932474
AllCCS[M+H]+120.132859911
AllCCS[M+H-H2O]+115.132859911
AllCCS[M+NH4]+124.932859911
AllCCS[M+Na]+126.332859911
AllCCS[M-H]-115.232859911
AllCCS[M+Na-2H]-118.232859911
AllCCS[M+HCOO]-121.532859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 202210.5088 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.25 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1206.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid426.1 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid132.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid304.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid126.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid342.6 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid484.0 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)619.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid733.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid230.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1010.3 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid287.6 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid323.1 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate705.6 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA305.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water251.6 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MALEIC ANHYDRIDEO=C1OC(=O)C=C11335.1Standard polar33892256
MALEIC ANHYDRIDEO=C1OC(=O)C=C1817.9Standard non polar33892256
MALEIC ANHYDRIDEO=C1OC(=O)C=C1898.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Maleic Anhydride GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fba-9000000000-076b3df6610ba137eb2e2021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Maleic Anhydride GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleic Anhydride 10V, Positive-QTOFsplash10-0002-9000000000-5f6845ace508aeaa87d62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleic Anhydride 20V, Positive-QTOFsplash10-0002-9000000000-cf7ac51b61d4c8e9cbc72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleic Anhydride 40V, Positive-QTOFsplash10-0a4i-9000000000-ede838acdc33a7a4b6132016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleic Anhydride 10V, Negative-QTOFsplash10-0002-9000000000-cc8e285ae469d64c11b22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleic Anhydride 20V, Negative-QTOFsplash10-0f6t-9000000000-62adcf1aa8a542f568142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleic Anhydride 40V, Negative-QTOFsplash10-0udi-9000000000-53b4cefef5376dc76cb02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleic Anhydride 10V, Negative-QTOFsplash10-0f6t-9000000000-87c59362a17d1ea2f9572021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleic Anhydride 20V, Negative-QTOFsplash10-0f6t-9000000000-ce3a4cd3672b1e603c242021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleic Anhydride 40V, Negative-QTOFsplash10-0udi-9000000000-b0461a540698308bc1db2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleic Anhydride 10V, Positive-QTOFsplash10-006t-9000000000-ecbf5c459973ee6337212021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleic Anhydride 20V, Positive-QTOFsplash10-0udi-9000000000-1ffa1bf7e22e198f93742021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleic Anhydride 40V, Positive-QTOFsplash10-0udl-9000000000-aabfe4f454de332b76882021-10-12Wishart 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 ID7635
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMaleic_anhydride
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID474859
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1256271
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 ]