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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:48 UTC
Update Date2022-03-07 02:52:36 UTC
HMDB IDHMDB0030587
Secondary Accession Numbers
  • HMDB30587
Metabolite Identification
Common NameSpinacetin
DescriptionSpinacetin belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, spinacetin is considered to be a flavonoid. Spinacetin has been detected, but not quantified in, a few different foods, such as german camomiles (Matricaria recutita), green vegetables, and spinaches (Spinacia oleracea). This could make spinacetin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Spinacetin.
Structure
Data?1563862008
Synonyms
ValueSource
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy-4H-1-benzopyran-4-oneHMDB
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy-4H-1-benzopyran-4-one, 9ciHMDB
4',5,7-Trihydroxy-3',6-dimethoxyflavonolHMDB
Quercetagetin 3',6-dimethyl etherHMDB
Chemical FormulaC17H14O8
Average Molecular Weight346.2883
Monoisotopic Molecular Weight346.068867424
IUPAC Name3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy-4H-chromen-4-one
Traditional Namespinacetin
CAS Registry Number3153-83-1
SMILES
COC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O1)C=C(O)C(OC)=C2O
InChI Identifier
InChI=1S/C17H14O8/c1-23-10-5-7(3-4-8(10)18)16-15(22)13(20)12-11(25-16)6-9(19)17(24-2)14(12)21/h3-6,18-19,21-22H,1-2H3
InChI KeyXWIDINOKCRFVHQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavonols
Alternative Parents
Substituents
  • 3-hydroxyflavone
  • 3p-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Chromone
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Phenol ether
  • Anisole
  • Methoxybenzene
  • Pyranone
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point235 - 236 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP1.97ALOGPS
logP2.14ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)6.96ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.68 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity87.81 m³·mol⁻¹ChemAxon
Polarizability33.52 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
DeepCCS[M+H]+180.74830932474
DeepCCS[M-H]-178.3930932474
DeepCCS[M-2H]-212.39530932474
DeepCCS[M+Na]+187.62330932474
AllCCS[M+H]+179.132859911
AllCCS[M+H-H2O]+175.832859911
AllCCS[M+NH4]+182.232859911
AllCCS[M+Na]+183.132859911
AllCCS[M-H]-178.832859911
AllCCS[M+Na-2H]-178.332859911
AllCCS[M+HCOO]-177.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SpinacetinCOC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O1)C=C(O)C(OC)=C2O5348.8Standard polar33892256
SpinacetinCOC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O1)C=C(O)C(OC)=C2O3256.2Standard non polar33892256
SpinacetinCOC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O1)C=C(O)C(OC)=C2O3213.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Spinacetin,1TMS,isomer #1COC1=CC(C2=C(O)C(=O)C3=C(O)C(OC)=C(O)C=C3O2)=CC=C1O[Si](C)(C)C3387.1Semi standard non polar33892256
Spinacetin,1TMS,isomer #2COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C(OC)=C(O)C=C3O2)=CC=C1O3365.5Semi standard non polar33892256
Spinacetin,1TMS,isomer #3COC1=CC(C2=C(O)C(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C)C=C3O2)=CC=C1O3396.6Semi standard non polar33892256
Spinacetin,1TMS,isomer #4COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O)C=C3O2)=CC=C1O3365.7Semi standard non polar33892256
Spinacetin,2TMS,isomer #1COC1=CC(C2=C(O)C(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C3311.3Semi standard non polar33892256
Spinacetin,2TMS,isomer #2COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O)C=C3O2)=CC=C1O[Si](C)(C)C3265.3Semi standard non polar33892256
Spinacetin,2TMS,isomer #3COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C(OC)=C(O)C=C3O2)=CC=C1O[Si](C)(C)C3277.1Semi standard non polar33892256
Spinacetin,2TMS,isomer #4COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C)C=C3O2)=CC=C1O3251.8Semi standard non polar33892256
Spinacetin,2TMS,isomer #5COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O)C=C3O2)=CC=C1O3231.2Semi standard non polar33892256
Spinacetin,2TMS,isomer #6COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O[Si](C)(C)C)C=C3O2)=CC=C1O3306.6Semi standard non polar33892256
Spinacetin,3TMS,isomer #1COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O[Si](C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C3185.1Semi standard non polar33892256
Spinacetin,3TMS,isomer #2COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C3187.1Semi standard non polar33892256
Spinacetin,3TMS,isomer #3COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O)C=C3O2)=CC=C1O[Si](C)(C)C3153.0Semi standard non polar33892256
Spinacetin,3TMS,isomer #4COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O[Si](C)(C)C)C=C3O2)=CC=C1O3190.9Semi standard non polar33892256
Spinacetin,4TMS,isomer #1COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O[Si](C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C3169.3Semi standard non polar33892256
Spinacetin,1TBDMS,isomer #1COC1=CC(C2=C(O)C(=O)C3=C(O)C(OC)=C(O)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3651.6Semi standard non polar33892256
Spinacetin,1TBDMS,isomer #2COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C(OC)=C(O)C=C3O2)=CC=C1O3607.2Semi standard non polar33892256
Spinacetin,1TBDMS,isomer #3COC1=CC(C2=C(O)C(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O3663.7Semi standard non polar33892256
Spinacetin,1TBDMS,isomer #4COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O)C=C3O2)=CC=C1O3626.5Semi standard non polar33892256
Spinacetin,2TBDMS,isomer #1COC1=CC(C2=C(O)C(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3821.8Semi standard non polar33892256
Spinacetin,2TBDMS,isomer #2COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3773.9Semi standard non polar33892256
Spinacetin,2TBDMS,isomer #3COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C(OC)=C(O)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3800.4Semi standard non polar33892256
Spinacetin,2TBDMS,isomer #4COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O3776.5Semi standard non polar33892256
Spinacetin,2TBDMS,isomer #5COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O)C=C3O2)=CC=C1O3736.3Semi standard non polar33892256
Spinacetin,2TBDMS,isomer #6COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O3805.9Semi standard non polar33892256
Spinacetin,3TBDMS,isomer #1COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3943.2Semi standard non polar33892256
Spinacetin,3TBDMS,isomer #2COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3954.7Semi standard non polar33892256
Spinacetin,3TBDMS,isomer #3COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C3873.2Semi standard non polar33892256
Spinacetin,3TBDMS,isomer #4COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O3905.1Semi standard non polar33892256
Spinacetin,4TBDMS,isomer #1COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C4012.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Spinacetin GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-0519000000-c25e35c11f659f3495412017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Spinacetin GC-MS (4 TMS) - 70eV, Positivesplash10-0300-2235279000-10c0fd00403347619b2c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Spinacetin 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 - Spinacetin 10V, Positive-QTOFsplash10-0002-0009000000-957ac4e433fc6b2751f92016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spinacetin 20V, Positive-QTOFsplash10-0002-0009000000-c5e43db3ff565826a4c52016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spinacetin 40V, Positive-QTOFsplash10-0v09-1942000000-410380ec6e1f5aa8fe812016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spinacetin 10V, Negative-QTOFsplash10-0002-0009000000-8b0f4a90bb9df4c8f6f62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spinacetin 20V, Negative-QTOFsplash10-0002-0129000000-82d2243f997d5f5cf90c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spinacetin 40V, Negative-QTOFsplash10-00di-5792000000-066b1710964e99631eb32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spinacetin 10V, Negative-QTOFsplash10-0002-0009000000-4173ab4cf400ed4c20372021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spinacetin 20V, Negative-QTOFsplash10-0002-0319000000-e23d4c458c94f7ee3d472021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spinacetin 40V, Negative-QTOFsplash10-01b9-1912000000-edd4ca9a2a915e71139b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spinacetin 10V, Positive-QTOFsplash10-0002-0009000000-24b80c82c41a998b9ea52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spinacetin 20V, Positive-QTOFsplash10-0002-0009000000-f2ca7ea72a8b60e044db2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spinacetin 40V, Positive-QTOFsplash10-00ls-1912000000-9df995d5cf27a949ebb42021-09-24Wishart LabView Spectrum
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 ID355
FooDB IDFDB002480
KNApSAcK IDC00004689
Chemspider ID4479178
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSpinacetin
METLIN IDNot Available
PubChem Compound5321435
PDB IDNot Available
ChEBI IDNot Available
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .