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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:52:59 UTC
Update Date2023-02-21 17:22:51 UTC
HMDB IDHMDB0032963
Secondary Accession Numbers
  • HMDB32963
Metabolite Identification
Common NameZeanic acid
DescriptionZeanic acid, also known as zeanate, belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions. Zeanic acid has been detected, but not quantified in, breakfast cereal and cereals and cereal products. This could make zeanic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Zeanic acid.
Structure
Data?1677000171
Synonyms
ValueSource
ZeanateGenerator
1,2-dihydro-8-Hydroxy-2-oxo-4-quinolinecarboxylic acidHMDB
2,8-Dihydroxycinchoninic acidHMDB
8-Hydroxy-2(1H)-quinolinone-4-carboxylic acidHMDB
2,8-Dihydroxyquinoline-4-carboxylateGenerator
Chemical FormulaC10H7NO4
Average Molecular Weight205.1669
Monoisotopic Molecular Weight205.037507717
IUPAC Name8-hydroxy-2-oxo-1,2-dihydroquinoline-4-carboxylic acid
Traditional Name8-hydroxy-2-oxo-1H-quinoline-4-carboxylic acid
CAS Registry Number30536-55-1
SMILES
OC(=O)C1=CC(=O)NC2=C1C=CC=C2O
InChI Identifier
InChI=1S/C10H7NO4/c12-7-3-1-2-5-6(10(14)15)4-8(13)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)
InChI KeyDVEVPRIOUKVFAM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinoline carboxylic acids
Direct ParentQuinoline carboxylic acids
Alternative Parents
Substituents
  • Quinoline-4-carboxylic acid
  • Dihydroquinolone
  • Hydroxyquinoline
  • 8-hydroxyquinoline
  • Dihydroquinoline
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyridinone
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Lactam
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point340 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.15 g/LALOGPS
logP1.58ALOGPS
logP0.78ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity53.26 m³·mol⁻¹ChemAxon
Polarizability18.84 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+144.04931661259
DarkChem[M-H]-144.50631661259
DeepCCS[M+H]+135.49730932474
DeepCCS[M-H]-133.10130932474
DeepCCS[M-2H]-167.87530932474
DeepCCS[M+Na]+142.33730932474
AllCCS[M+H]+142.732859911
AllCCS[M+H-H2O]+138.432859911
AllCCS[M+NH4]+146.732859911
AllCCS[M+Na]+147.932859911
AllCCS[M-H]-139.832859911
AllCCS[M+Na-2H]-139.732859911
AllCCS[M+HCOO]-139.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Zeanic acidOC(=O)C1=CC(=O)NC2=C1C=CC=C2O3444.7Standard polar33892256
Zeanic acidOC(=O)C1=CC(=O)NC2=C1C=CC=C2O1762.4Standard non polar33892256
Zeanic acidOC(=O)C1=CC(=O)NC2=C1C=CC=C2O2200.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Zeanic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(=O)[NH]C2=C(O)C=CC=C122179.8Semi standard non polar33892256
Zeanic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC=CC2=C1[NH]C(=O)C=C2C(=O)O2197.1Semi standard non polar33892256
Zeanic acid,1TMS,isomer #3C[Si](C)(C)N1C(=O)C=C(C(=O)O)C2=CC=CC(O)=C212238.0Semi standard non polar33892256
Zeanic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(=O)[NH]C2=C(O[Si](C)(C)C)C=CC=C122182.5Semi standard non polar33892256
Zeanic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC(=O)N([Si](C)(C)C)C2=C(O)C=CC=C122240.6Semi standard non polar33892256
Zeanic acid,2TMS,isomer #3C[Si](C)(C)OC1=CC=CC2=C1N([Si](C)(C)C)C(=O)C=C2C(=O)O2295.7Semi standard non polar33892256
Zeanic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(=O)N([Si](C)(C)C)C2=C(O[Si](C)(C)C)C=CC=C122306.3Semi standard non polar33892256
Zeanic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(=O)N([Si](C)(C)C)C2=C(O[Si](C)(C)C)C=CC=C122328.3Standard non polar33892256
Zeanic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)[NH]C2=C(O)C=CC=C122431.3Semi standard non polar33892256
Zeanic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1[NH]C(=O)C=C2C(=O)O2425.5Semi standard non polar33892256
Zeanic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)C=C(C(=O)O)C2=CC=CC(O)=C212453.7Semi standard non polar33892256
Zeanic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)[NH]C2=C(O[Si](C)(C)C(C)(C)C)C=CC=C122678.0Semi standard non polar33892256
Zeanic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)N([Si](C)(C)C(C)(C)C)C2=C(O)C=CC=C122684.1Semi standard non polar33892256
Zeanic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1N([Si](C)(C)C(C)(C)C)C(=O)C=C2C(=O)O2754.6Semi standard non polar33892256
Zeanic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)N([Si](C)(C)C(C)(C)C)C2=C(O[Si](C)(C)C(C)(C)C)C=CC=C122935.0Semi standard non polar33892256
Zeanic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(=O)N([Si](C)(C)C(C)(C)C)C2=C(O[Si](C)(C)C(C)(C)C)C=CC=C122913.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Zeanic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bvi-0910000000-a4a471b793200915eaf82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zeanic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0259-4092000000-ffa0d06c6207788478fd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zeanic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zeanic acid 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 - Zeanic acid 10V, Positive-QTOFsplash10-0a4i-0690000000-a6ff7c3810f8b288b3552016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zeanic acid 20V, Positive-QTOFsplash10-03dr-0920000000-bd37d73040f60e46b1a22016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zeanic acid 40V, Positive-QTOFsplash10-03di-0900000000-41535c65e309643e1d342016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zeanic acid 10V, Negative-QTOFsplash10-0udi-0490000000-9878ecee970924f385f82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zeanic acid 20V, Negative-QTOFsplash10-0ik9-0940000000-28b8b02462afcf6267672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zeanic acid 40V, Negative-QTOFsplash10-01q9-2900000000-0a6b548068bfeb78aa292016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zeanic acid 10V, Positive-QTOFsplash10-052r-0980000000-8e535c27b033b9f60b6b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zeanic acid 20V, Positive-QTOFsplash10-0bti-0970000000-c1e165752a1b59a886a62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zeanic acid 40V, Positive-QTOFsplash10-01q9-0900000000-e3430ac531b100a1dd7a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zeanic acid 10V, Negative-QTOFsplash10-03di-0940000000-1e67d24e4b09c4626d382021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zeanic acid 20V, Negative-QTOFsplash10-03di-0900000000-c64eb4629fec3a98aeab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zeanic acid 40V, Negative-QTOFsplash10-053r-1900000000-7b6f58aca4afd4ca82352021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010949
KNApSAcK IDC00048629
Chemspider ID27286995
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13988328
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .