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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:34:19 UTC
Update Date2022-03-07 02:55:17 UTC
HMDB IDHMDB0037334
Secondary Accession Numbers
  • HMDB37334
Metabolite Identification
Common NameMajoranin
DescriptionMajoranin, also known as mucroflavone b or thymonin, belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, majoranin is considered to be a flavonoid. Majoranin has been detected, but not quantified in, sweet marjorams (Origanum majorana). This could make majoranin a potential biomarker for the consumption of these foods. Majoranin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Majoranin.
Structure
Data?1563863013
Synonyms
ValueSource
5,6,4'-Trihydroxy-7,8,3'-trimethoxyflavoneChEBI
5,6-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7,8-dimethoxy-4H-1-benzopyran-4-oneChEBI
Mucroflavone bChEBI
ThymoninHMDB
MajoraninChEBI
Chemical FormulaC18H16O8
Average Molecular Weight360.3148
Monoisotopic Molecular Weight360.084517488
IUPAC Name5,6-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7,8-dimethoxy-4H-chromen-4-one
Traditional Namethymonin
CAS Registry Number76844-67-2
SMILES
COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C(O)=C(OC)C(OC)=C2O1
InChI Identifier
InChI=1S/C18H16O8/c1-23-12-6-8(4-5-9(12)19)11-7-10(20)13-14(21)15(22)17(24-2)18(25-3)16(13)26-11/h4-7,19,21-22H,1-3H3
InChI KeyBAIRXMVFPKLWSE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent8-O-methylated flavonoids
Alternative Parents
Substituents
  • 7-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • 3p-methoxyflavonoid-skeleton
  • Flavone
  • Hydroxyflavonoid
  • 6-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Chromone
  • Methoxyphenol
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Methoxybenzene
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point225 - 226 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility33.91 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.069 g/LALOGPS
logP2.69ALOGPS
logP2.23ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.92ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area114.68 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity92.3 m³·mol⁻¹ChemAxon
Polarizability35.48 ųChemAxon
Number of Rings3ChemAxon
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]+183.53331661259
DarkChem[M-H]-187.39931661259
DeepCCS[M+H]+179.66530932474
DeepCCS[M-H]-177.30730932474
DeepCCS[M-2H]-211.30430932474
DeepCCS[M+Na]+186.53230932474
AllCCS[M+H]+182.732859911
AllCCS[M+H-H2O]+179.432859911
AllCCS[M+NH4]+185.732859911
AllCCS[M+Na]+186.532859911
AllCCS[M-H]-184.332859911
AllCCS[M+Na-2H]-184.132859911
AllCCS[M+HCOO]-183.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MajoraninCOC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C(O)=C(OC)C(OC)=C2O15219.4Standard polar33892256
MajoraninCOC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C(O)=C(OC)C(OC)=C2O13462.2Standard non polar33892256
MajoraninCOC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C(O)=C(OC)C(OC)=C2O13381.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Majoranin,1TMS,isomer #1COC1=CC(C2=CC(=O)C3=C(O)C(O)=C(OC)C(OC)=C3O2)=CC=C1O[Si](C)(C)C3384.7Semi standard non polar33892256
Majoranin,1TMS,isomer #2COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C(O)=C(OC)C(OC)=C3O2)=CC=C1O3388.8Semi standard non polar33892256
Majoranin,1TMS,isomer #3COC1=CC(C2=CC(=O)C3=C(O)C(O[Si](C)(C)C)=C(OC)C(OC)=C3O2)=CC=C1O3397.2Semi standard non polar33892256
Majoranin,2TMS,isomer #1COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C(O)=C(OC)C(OC)=C3O2)=CC=C1O[Si](C)(C)C3296.5Semi standard non polar33892256
Majoranin,2TMS,isomer #2COC1=CC(C2=CC(=O)C3=C(O)C(O[Si](C)(C)C)=C(OC)C(OC)=C3O2)=CC=C1O[Si](C)(C)C3303.4Semi standard non polar33892256
Majoranin,2TMS,isomer #3COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(OC)C(OC)=C3O2)=CC=C1O3312.4Semi standard non polar33892256
Majoranin,3TMS,isomer #1COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(OC)C(OC)=C3O2)=CC=C1O[Si](C)(C)C3225.9Semi standard non polar33892256
Majoranin,1TBDMS,isomer #1COC1=CC(C2=CC(=O)C3=C(O)C(O)=C(OC)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3595.0Semi standard non polar33892256
Majoranin,1TBDMS,isomer #2COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(O)=C(OC)C(OC)=C3O2)=CC=C1O3596.4Semi standard non polar33892256
Majoranin,1TBDMS,isomer #3COC1=CC(C2=CC(=O)C3=C(O)C(O[Si](C)(C)C(C)(C)C)=C(OC)C(OC)=C3O2)=CC=C1O3607.8Semi standard non polar33892256
Majoranin,2TBDMS,isomer #1COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(O)=C(OC)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3763.2Semi standard non polar33892256
Majoranin,2TBDMS,isomer #2COC1=CC(C2=CC(=O)C3=C(O)C(O[Si](C)(C)C(C)(C)C)=C(OC)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3765.0Semi standard non polar33892256
Majoranin,2TBDMS,isomer #3COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(OC)C(OC)=C3O2)=CC=C1O3751.5Semi standard non polar33892256
Majoranin,3TBDMS,isomer #1COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(OC)C(OC)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3893.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Majoranin GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-0209000000-61cc202a25f50826efa12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Majoranin GC-MS (3 TMS) - 70eV, Positivesplash10-03fr-2021190000-95ebb1cee77eb3b76a4f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Majoranin 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 - Majoranin 10V, Positive-QTOFsplash10-03di-0009000000-02453d986be155ce351b2016-06-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Majoranin 20V, Positive-QTOFsplash10-03di-0019000000-469fa85eff4063be1a262016-06-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Majoranin 40V, Positive-QTOFsplash10-0wmi-1966000000-8109118f4352165e55682016-06-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Majoranin 10V, Negative-QTOFsplash10-0a4i-0009000000-0be46164b0dca2bed6382016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Majoranin 20V, Negative-QTOFsplash10-0a4l-0019000000-7575c59bb70be2a0af532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Majoranin 40V, Negative-QTOFsplash10-05uu-1293000000-211f2f2bb29d6acbe78b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Majoranin 10V, Negative-QTOFsplash10-0a4i-0009000000-1b2458f70b43c2827ff82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Majoranin 20V, Negative-QTOFsplash10-0aou-0009000000-4c3c8fe1d4a9cb77292d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Majoranin 10V, Positive-QTOFsplash10-03di-0009000000-ef0e36da9abfe27aa0762021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Majoranin 20V, Positive-QTOFsplash10-03di-0009000000-c383b2e8879413a775be2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Majoranin 40V, Positive-QTOFsplash10-014s-0339000000-565bc170653b834a0cdf2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB006350
KNApSAcK IDC00003931
Chemspider ID391021
KEGG Compound IDC10191
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442662
PDB IDNot Available
ChEBI ID9582
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1859931
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.. .