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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:42:49 UTC
Update Date2019-07-23 06:21:28 UTC
HMDB IDHMDB0036557
Secondary Accession Numbers
  • HMDB36557
Metabolite Identification
Common NameMS 3
DescriptionMS 3, also known as amsacrine or glyo-i, belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). MS 3 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, MS 3 has been detected, but not quantified in, mushrooms. This could make MS 3 a potential biomarker for the consumption of these foods.
Structure
Data?1563862888
Synonyms
ValueSource
2,4-Dihydroxy-6-methylbenzoic acid 3-hydroxy-4,5-bis(hydroxymethyl)-2-(3-methyl-2-butenyl)phenyl ester, 9ciHMDB
3-Hydroxy-4,5-bis(hydroxymethyl)-2-prenylphenyl 2,4-dihydroxy-6-methylbenzoateHMDB
4'-(9-Acridinylamino)-3'-methoxymethanesulfonanilideHMDB
AmsacrineHMDB
Glyo-IHMDB
Glyoxalase IHMDB
Lactoylglutathione lyaseHMDB
MamsaHMDB
MS-3 (GLYOXALASE inhibitor)HMDB
3-Hydroxy-4,5-bis(hydroxymethyl)-2-(3-methylbut-2-en-1-yl)phenyl 2,4-dihydroxy-6-methylbenzoic acidGenerator
Lyase, lactoyl glutathioneMeSH
MethylglyoxalaseMeSH
Glutathione lyase, lactoylMeSH
Lactoyl glutathione lyaseMeSH
Lyase, lactoylglutathioneMeSH
Chemical FormulaC21H24O7
Average Molecular Weight388.4111
Monoisotopic Molecular Weight388.152203122
IUPAC Name3-hydroxy-4,5-bis(hydroxymethyl)-2-(3-methylbut-2-en-1-yl)phenyl 2,4-dihydroxy-6-methylbenzoate
Traditional Name3-hydroxy-4,5-bis(hydroxymethyl)-2-(3-methylbut-2-en-1-yl)phenyl 2,4-dihydroxy-6-methylbenzoate
CAS Registry Number58265-74-0
SMILES
CC(C)=CCC1=C(OC(=O)C2=C(O)C=C(O)C=C2C)C=C(CO)C(CO)=C1O
InChI Identifier
InChI=1S/C21H24O7/c1-11(2)4-5-15-18(7-13(9-22)16(10-23)20(15)26)28-21(27)19-12(3)6-14(24)8-17(19)25/h4,6-8,22-26H,5,9-10H2,1-3H3
InChI KeyWTZUCTQSBSDSRG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDepsides and depsidones
Sub ClassNot Available
Direct ParentDepsides and depsidones
Alternative Parents
Substituents
  • Depside backbone
  • P-hydroxybenzoic acid ester
  • O-hydroxybenzoic acid ester
  • Dihydroxybenzoic acid
  • Phenol ester
  • Salicylic acid or derivatives
  • Benzoate ester
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Resorcinol
  • Benzyl alcohol
  • M-cresol
  • Benzoyl
  • Toluene
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Primary alcohol
  • Aromatic alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point92 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP2.2ALOGPS
logP4.08ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)8.51ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.45 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity106.72 m³·mol⁻¹ChemAxon
Polarizability41.23 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-1913000000-7dbb522743f945b53401Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-03di-2120019000-b958031070c63f456812Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0119000000-2cab3e19bfd6403a4753Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-1439000000-a792d62d46e40adb97b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-3922000000-8d81ad326fa48a94c79eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0119000000-6ca22e61e4c8865ed330Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05tr-0519000000-74ec77f4076a0ca04344Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-2931000000-36a6aedcad4470ca69fcSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB015460
KNApSAcK IDNot Available
Chemspider ID90762
KEGG Compound IDC01553
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMS3
METLIN IDNot Available
PubChem Compound100450
PDB IDNot Available
ChEBI ID49496
Food Biomarker OntologyNot Available
VMH 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.. .