Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:51:12 UTC
Update Date2022-03-07 02:55:25 UTC
HMDB IDHMDB0037600
Secondary Accession Numbers
  • HMDB37600
Metabolite Identification
Common NameXanthomicrol
DescriptionXanthomicrol 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, xanthomicrol is considered to be a flavonoid. Xanthomicrol is found, on average, in the highest concentration within sweet basils (Ocimum basilicum). Xanthomicrol has also been detected, but not quantified in, several different foods, such as citrus, herbs and spices, peppermints (Mentha X piperita), and winter savories (Satureja montana). This could make xanthomicrol a potential biomarker for the consumption of these foods. Xanthomicrol 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 Xanthomicrol.
Structure
Data?1563863058
Synonyms
ValueSource
4',5-Dihydroxy-6,7,8-trimethoxyflavoneChEBI
5-Hydroxy-2-(4-hydroxyphenyl)-6,7,8-trimethoxy-4H-1-benzopyran-4-oneHMDB
Chemical FormulaC18H16O7
Average Molecular Weight344.3154
Monoisotopic Molecular Weight344.089602866
IUPAC Name5-hydroxy-2-(4-hydroxyphenyl)-6,7,8-trimethoxy-4H-chromen-4-one
Traditional Namexanthomicrol
CAS Registry Number16545-23-6
SMILES
COC1=C(OC)C(OC)=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C18H16O7/c1-22-16-14(21)13-11(20)8-12(9-4-6-10(19)7-5-9)25-15(13)17(23-2)18(16)24-3/h4-8,19,21H,1-3H3
InChI KeySAMBWAJRKKEEOR-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
  • 6-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • 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 Point227 - 230 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility159.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP2.89ALOGPS
logP2.54ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)8.67ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area94.45 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity90.32 m³·mol⁻¹ChemAxon
Polarizability34.64 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]+180.41831661259
DarkChem[M-H]-181.9731661259
DeepCCS[M+H]+182.7530932474
DeepCCS[M-H]-180.3430932474
DeepCCS[M-2H]-214.68430932474
DeepCCS[M+Na]+190.22330932474
AllCCS[M+H]+179.732859911
AllCCS[M+H-H2O]+176.432859911
AllCCS[M+NH4]+182.832859911
AllCCS[M+Na]+183.732859911
AllCCS[M-H]-181.732859911
AllCCS[M+Na-2H]-181.432859911
AllCCS[M+HCOO]-181.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
XanthomicrolCOC1=C(OC)C(OC)=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C14818.1Standard polar33892256
XanthomicrolCOC1=C(OC)C(OC)=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C13229.9Standard non polar33892256
XanthomicrolCOC1=C(OC)C(OC)=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C13252.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Xanthomicrol,1TMS,isomer #1COC1=C(OC)C(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1OC3164.5Semi standard non polar33892256
Xanthomicrol,1TMS,isomer #2COC1=C(OC)C(O)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C)C=C3)OC2=C1OC3228.7Semi standard non polar33892256
Xanthomicrol,2TMS,isomer #1COC1=C(OC)C(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C)C=C3)OC2=C1OC3203.9Semi standard non polar33892256
Xanthomicrol,1TBDMS,isomer #1COC1=C(OC)C(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1OC3412.2Semi standard non polar33892256
Xanthomicrol,1TBDMS,isomer #2COC1=C(OC)C(O)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)OC2=C1OC3434.8Semi standard non polar33892256
Xanthomicrol,2TBDMS,isomer #1COC1=C(OC)C(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)OC2=C1OC3644.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Xanthomicrol GC-MS (Non-derivatized) - 70eV, Positivesplash10-02vi-0119000000-0c0e3709b7f79d4ca2062017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthomicrol GC-MS (2 TMS) - 70eV, Positivesplash10-00di-1111900000-21e3d411a6a5821413b02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthomicrol 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 - Xanthomicrol 10V, Negative-QTOFsplash10-0006-0009000000-7123f771ed6080c1a1852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthomicrol 20V, Negative-QTOFsplash10-0006-0019000000-7d461a8e7316b5241de22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthomicrol 40V, Negative-QTOFsplash10-05r4-1491000000-f7bf40ad7c31df0b7fea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthomicrol 10V, Negative-QTOFsplash10-0006-0009000000-72fbd0eb75bc9ea05c552021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthomicrol 20V, Negative-QTOFsplash10-0f96-0009000000-a822a609c08dacb282e42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthomicrol 10V, Positive-QTOFsplash10-0002-0009000000-444df5d8e4a6a98b29e22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthomicrol 20V, Positive-QTOFsplash10-0002-0009000000-17bd95784ea2af1d207b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthomicrol 40V, Positive-QTOFsplash10-00mk-2393000000-dde4b83302a1581e76352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthomicrol 10V, Positive-QTOFsplash10-0002-0009000000-5dc8eb0c39637af070862021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthomicrol 20V, Positive-QTOFsplash10-0002-0009000000-5dc6fda56294b4fda1a72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthomicrol 40V, Positive-QTOFsplash10-0uk9-0249000000-6e1101312f640edf15332021-09-24Wishart 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 IDFDB016712
KNApSAcK IDC00003879
Chemspider ID65965
KEGG Compound IDC14476
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73207
PDB IDNot Available
ChEBI ID35047
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1862661
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Abbaszadeh H, Ebrahimi SA, Akhavan MM: Antiangiogenic activity of xanthomicrol and calycopterin, two polymethoxylated hydroxyflavones in both in vitro and ex vivo models. Phytother Res. 2014 Nov;28(11):1661-70. doi: 10.1002/ptr.5179. Epub 2014 Jun 3. [PubMed:24895220 ]