Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:57:26 UTC
Update Date2023-02-21 17:29:56 UTC
HMDB IDHMDB0060374
Secondary Accession Numbers
  • HMDB60374
Metabolite Identification
Common Name3-Methoxyanthranilate
Description3-Methoxyanthranilate belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. 3-Methoxyanthranilate is a strong basic compound (based on its pKa). 3-Methoxyanthranilate exists in all living organisms, ranging from bacteria to humans. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
Structure
Data?1677000596
Synonyms
ValueSource
3-Methoxyanthranilic acidKegg
3-MethoxyanthranilateGenerator
Chemical FormulaC8H9NO3
Average Molecular Weight167.162
Monoisotopic Molecular Weight167.058243159
IUPAC Name2-amino-3-methoxybenzoic acid
Traditional Name2-amino-3-methoxybenzoic acid
CAS Registry NumberNot Available
SMILES
COC1=CC=CC(C(O)=O)=C1N
InChI Identifier
InChI=1S/C8H9NO3/c1-12-6-4-2-3-5(7(6)9)8(10)11/h2-4H,9H2,1H3,(H,10,11)
InChI KeySXOPCLUOUFQBJV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentM-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • M-methoxybenzoic acid or derivatives
  • Aminobenzoic acid or derivatives
  • Aminobenzoic acid
  • Benzoic acid
  • Methoxyaniline
  • Aminophenyl ether
  • Anisole
  • Methoxybenzene
  • Aniline or substituted anilines
  • Phenol ether
  • Benzoyl
  • Phenoxy compound
  • Alkyl aryl ether
  • Vinylogous amide
  • Amino acid
  • Amino acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
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
Water Solubility4.56 g/LALOGPS
logP0.77ALOGPS
logP1.29ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.9ChemAxon
pKa (Strongest Basic)4.78ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area72.55 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.48 m³·mol⁻¹ChemAxon
Polarizability16.18 ųChemAxon
Number of Rings1ChemAxon
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]+136.13331661259
DarkChem[M-H]-135.48831661259
DeepCCS[M+H]+136.46530932474
DeepCCS[M-H]-134.01130932474
DeepCCS[M-2H]-170.26330932474
DeepCCS[M+Na]+145.43430932474
AllCCS[M+H]+136.532859911
AllCCS[M+H-H2O]+132.132859911
AllCCS[M+NH4]+140.532859911
AllCCS[M+Na]+141.732859911
AllCCS[M-H]-132.732859911
AllCCS[M+Na-2H]-133.832859911
AllCCS[M+HCOO]-135.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-MethoxyanthranilateCOC1=CC=CC(C(O)=O)=C1N2756.3Standard polar33892256
3-MethoxyanthranilateCOC1=CC=CC(C(O)=O)=C1N1627.4Standard non polar33892256
3-MethoxyanthranilateCOC1=CC=CC(C(O)=O)=C1N1650.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Methoxyanthranilate,1TMS,isomer #1COC1=CC=CC(C(=O)O[Si](C)(C)C)=C1N1688.4Semi standard non polar33892256
3-Methoxyanthranilate,1TMS,isomer #2COC1=CC=CC(C(=O)O)=C1N[Si](C)(C)C1795.9Semi standard non polar33892256
3-Methoxyanthranilate,2TMS,isomer #1COC1=CC=CC(C(=O)O[Si](C)(C)C)=C1N[Si](C)(C)C1800.1Semi standard non polar33892256
3-Methoxyanthranilate,2TMS,isomer #1COC1=CC=CC(C(=O)O[Si](C)(C)C)=C1N[Si](C)(C)C1810.3Standard non polar33892256
3-Methoxyanthranilate,2TMS,isomer #1COC1=CC=CC(C(=O)O[Si](C)(C)C)=C1N[Si](C)(C)C2085.8Standard polar33892256
3-Methoxyanthranilate,2TMS,isomer #2COC1=CC=CC(C(=O)O)=C1N([Si](C)(C)C)[Si](C)(C)C1822.1Semi standard non polar33892256
3-Methoxyanthranilate,2TMS,isomer #2COC1=CC=CC(C(=O)O)=C1N([Si](C)(C)C)[Si](C)(C)C1902.9Standard non polar33892256
3-Methoxyanthranilate,2TMS,isomer #2COC1=CC=CC(C(=O)O)=C1N([Si](C)(C)C)[Si](C)(C)C2093.5Standard polar33892256
3-Methoxyanthranilate,3TMS,isomer #1COC1=CC=CC(C(=O)O[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C1855.9Semi standard non polar33892256
3-Methoxyanthranilate,3TMS,isomer #1COC1=CC=CC(C(=O)O[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C1894.2Standard non polar33892256
3-Methoxyanthranilate,3TMS,isomer #1COC1=CC=CC(C(=O)O[Si](C)(C)C)=C1N([Si](C)(C)C)[Si](C)(C)C1953.9Standard polar33892256
3-Methoxyanthranilate,1TBDMS,isomer #1COC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1N1955.0Semi standard non polar33892256
3-Methoxyanthranilate,1TBDMS,isomer #2COC1=CC=CC(C(=O)O)=C1N[Si](C)(C)C(C)(C)C2031.3Semi standard non polar33892256
3-Methoxyanthranilate,2TBDMS,isomer #1COC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1N[Si](C)(C)C(C)(C)C2273.1Semi standard non polar33892256
3-Methoxyanthranilate,2TBDMS,isomer #1COC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1N[Si](C)(C)C(C)(C)C2240.3Standard non polar33892256
3-Methoxyanthranilate,2TBDMS,isomer #1COC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1N[Si](C)(C)C(C)(C)C2345.8Standard polar33892256
3-Methoxyanthranilate,2TBDMS,isomer #2COC1=CC=CC(C(=O)O)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2305.3Semi standard non polar33892256
3-Methoxyanthranilate,2TBDMS,isomer #2COC1=CC=CC(C(=O)O)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2300.2Standard non polar33892256
3-Methoxyanthranilate,2TBDMS,isomer #2COC1=CC=CC(C(=O)O)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2300.4Standard polar33892256
3-Methoxyanthranilate,3TBDMS,isomer #1COC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2534.7Semi standard non polar33892256
3-Methoxyanthranilate,3TBDMS,isomer #1COC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2471.7Standard non polar33892256
3-Methoxyanthranilate,3TBDMS,isomer #1COC1=CC=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2337.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Methoxyanthranilate GC-MS (2 TMS)splash10-0035-3930000000-3333f2b5836d47d347a12014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Methoxyanthranilate GC-EI-TOF (Non-derivatized)splash10-0002-0970000000-864c46f5aa84823c21242017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Methoxyanthranilate GC-EI-TOF (Non-derivatized)splash10-00di-1920000000-4de2b678dbb54370c9072017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Methoxyanthranilate GC-MS (Non-derivatized)splash10-0035-3930000000-3333f2b5836d47d347a12017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxyanthranilate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xr-2900000000-1bad15fb72f82f97d24e2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxyanthranilate GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9630000000-01aef289201ca2ba41672017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxyanthranilate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxyanthranilate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methoxyanthranilate 35V, Positive-QTOFsplash10-0udi-6900000000-8c4d2871ab7330d9ba942021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methoxyanthranilate 35V, Negative-QTOFsplash10-0a4i-0900000000-005b2f2b5a37a65855062021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxyanthranilate 10V, Positive-QTOFsplash10-0uxr-0900000000-09a1fea779751275fc182017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxyanthranilate 20V, Positive-QTOFsplash10-0uk9-0900000000-0a5d93d01afc04f9ef7e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxyanthranilate 40V, Positive-QTOFsplash10-0kor-9500000000-4e090d1386d9bea20a212017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxyanthranilate 10V, Negative-QTOFsplash10-00xr-0900000000-4f22b013ccfbf7aa6a812017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxyanthranilate 20V, Negative-QTOFsplash10-05fr-1900000000-bfffb27d7244351128662017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxyanthranilate 40V, Negative-QTOFsplash10-0a4i-5900000000-e3b9913b1e4873a5cb112017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxyanthranilate 10V, Positive-QTOFsplash10-0udi-0900000000-a63a3b7a842abb237db02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxyanthranilate 20V, Positive-QTOFsplash10-0udi-0900000000-21c8556267c02694cdcd2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxyanthranilate 40V, Positive-QTOFsplash10-0ukc-9300000000-814ffcd5bca10e836d842021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxyanthranilate 10V, Negative-QTOFsplash10-00xr-0900000000-7c4296663dab84d8c5e92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxyanthranilate 20V, Negative-QTOFsplash10-0a4i-0900000000-629eab2ac1befdf6d4862021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxyanthranilate 40V, Negative-QTOFsplash10-0a4i-5900000000-1f3849bbc1cf0bf2f6482021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart 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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05831
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound255720
PDB IDNot Available
ChEBI ID27440
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. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Not Available
Specific function:
N5-glutamine methyltransferase responsible for the methylation of the GGQ triplet of the mitochondrial translation release factor MTRF1L.
Gene Name:
HEMK1
Uniprot ID:
Q9Y5R4
Molecular weight:
Not Available
Reactions
3-Hydroxyanthranilic acid + S-Adenosylmethionine → 3-Methoxyanthranilate + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL2B
Uniprot ID:
Q6P1Q9
Molecular weight:
Not Available
Reactions
3-Hydroxyanthranilic acid + S-Adenosylmethionine → 3-Methoxyanthranilate + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL6
Uniprot ID:
Q8TCB7
Molecular weight:
Not Available
Reactions
3-Hydroxyanthranilic acid + S-Adenosylmethionine → 3-Methoxyanthranilate + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Methyltransferase that may act on DNA.
Gene Name:
WBSCR22
Uniprot ID:
O43709
Molecular weight:
Not Available
Reactions
3-Hydroxyanthranilic acid + S-Adenosylmethionine → 3-Methoxyanthranilate + S-Adenosylhomocysteinedetails