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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:59:24 UTC
Update Date2017-10-23 19:15:48 UTC
HMDB IDHMDB0060787
Secondary Accession Numbers
  • HMDB60787
Metabolite Identification
Common Name6-Methoxy-2-naphthylacetic acid
Description6-Methoxy-2-naphthylacetic acid is a metabolite of nabumetone. Nabumetone is a non-steroidal anti-inflammatory drug (NSAID), the only 1-naphthaleneacetic acid derivative. Nabumetone has been developed by Beecham. It is available under numerous brand names, such as Relafen, Relifex and Gambaran. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC39H37NO12
Average Molecular Weight711.7106
Monoisotopic Molecular Weight711.231575653
IUPAC Name2-[(2S,4S)-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl]-2-oxoethyl 2-(naphthalen-1-yl)acetate
Traditional Name2-[(2S,4S)-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]-2-oxoethyl 2-(naphthalen-1-yl)acetate
CAS Registry NumberNot Available
SMILES
COC1=CC=CC2=C1C(=O)C1=C(C(O)=C3C[C@](O)(C[C@H](OC4CC(N)C(O)C(C)O4)C3=C1O)C(=O)COC(=O)CC1=CC=CC3=CC=CC=C13)C2=O
InChI Identifier
InChI=1S/C39H37NO12/c1-18-34(43)24(40)14-29(51-18)52-26-16-39(48,27(41)17-50-28(42)13-20-9-5-8-19-7-3-4-10-21(19)20)15-23-31(26)38(47)33-32(36(23)45)35(44)22-11-6-12-25(49-2)30(22)37(33)46/h3-12,18,24,26,29,34,43,45,47-48H,13-17,40H2,1-2H3/t18?,24?,26-,29?,34?,39-/m0/s1
InChI KeyGYCQOHQXGJAWAC-XFZKEZEPSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassAnthracyclines
Direct ParentAnthracyclines
Alternative Parents
Substituents
  • Anthracycline
  • Anthracyclinone-skeleton
  • Aminoglycoside core
  • Tetracenequinone
  • 9,10-anthraquinone
  • 1,4-anthraquinone
  • Anthracene
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Tetralin
  • Aryl ketone
  • Anisole
  • Amino saccharide
  • Alkyl aryl ether
  • Alpha-acyloxy ketone
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Vinylogous acid
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Ketone
  • Organoheterocyclic compound
  • Ether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • Oxacycle
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Primary aliphatic amine
  • Organonitrogen compound
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.018 g/LALOGPS
logP2.95ALOGPS
logP4.18ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.53ChemAxon
pKa (Strongest Basic)8.94ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area212.14 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity184.92 m³·mol⁻¹ChemAxon
Polarizability73.9 ųChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-4900200000-9d7949be4a71ca079fb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02u3-0602194300-a1d03a1222aa72394718View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015a-0904171000-43793ae7cbc3a354be20View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-3906011000-f70870016b3535f63bc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-029i-0900031200-30f6ee120a88e645fe01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0901010000-1590cf5fe3d4bac188dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-0901000000-de625c9bcbff1ac9e825View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00764
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      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
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available