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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:46:32 UTC
Update Date2022-03-07 02:53:10 UTC
HMDB IDHMDB0031922
Secondary Accession Numbers
  • HMDB31922
Metabolite Identification
Common Name1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone
Description1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, 1-(2,4-dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone is considered to be a flavonoid. 1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone has been detected, but not quantified in, breadfruits (Artocarpus altilis) and fruits. This could make 1-(2,4-dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone.
Structure
Data?1563862191
Synonyms
ValueSource
4,2',4'-Trihydroxy-6''-methyl-6''-(4-methyl-3-pentenyl)pyrano[2'',3'':3,2]dihydrochalconeHMDB
Chemical FormulaC25H28O5
Average Molecular Weight408.4868
Monoisotopic Molecular Weight408.193674006
IUPAC Name1-(2,4-dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-2H-chromen-5-yl]propan-1-one
Traditional Name1-(2,4-dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)chromen-5-yl]propan-1-one
CAS Registry Number116207-29-5
SMILES
CC(C)=CCCC1(C)OC2=C(O)C=CC(CCC(=O)C3=C(O)C=C(O)C=C3)=C2C=C1
InChI Identifier
InChI=1S/C25H28O5/c1-16(2)5-4-13-25(3)14-12-19-17(7-11-22(28)24(19)30-25)6-10-21(27)20-9-8-18(26)15-23(20)29/h5,7-9,11-12,14-15,26,28-29H,4,6,10,13H2,1-3H3
InChI KeyNZEMOONSVTXJCP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct Parent2'-Hydroxy-dihydrochalcones
Alternative Parents
Substituents
  • 2'-hydroxy-dihydrochalcone
  • Alkyl-phenylketone
  • Butyrophenone
  • Benzopyran
  • 1-benzopyran
  • Phenylketone
  • Benzoyl
  • Aryl alkyl ketone
  • Aryl ketone
  • Resorcinol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0028 g/LALOGPS
logP4.73ALOGPS
logP6.19ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)7.88ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity119.85 m³·mol⁻¹ChemAxon
Polarizability45.52 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+201.49731661259
DarkChem[M-H]-195.86431661259
DeepCCS[M+H]+204.57230932474
DeepCCS[M-H]-202.21430932474
DeepCCS[M-2H]-236.08230932474
DeepCCS[M+Na]+211.3130932474
AllCCS[M+H]+206.032859911
AllCCS[M+H-H2O]+203.332859911
AllCCS[M+NH4]+208.632859911
AllCCS[M+Na]+209.332859911
AllCCS[M-H]-199.532859911
AllCCS[M+Na-2H]-200.032859911
AllCCS[M+HCOO]-200.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanoneCC(C)=CCCC1(C)OC2=C(O)C=CC(CCC(=O)C3=C(O)C=C(O)C=C3)=C2C=C14574.2Standard polar33892256
1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanoneCC(C)=CCCC1(C)OC2=C(O)C=CC(CCC(=O)C3=C(O)C=C(O)C=C3)=C2C=C13237.3Standard non polar33892256
1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanoneCC(C)=CCCC1(C)OC2=C(O)C=CC(CCC(=O)C3=C(O)C=C(O)C=C3)=C2C=C13532.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone,1TMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(CCC(=O)C3=CC=C(O)C=C3O)C=CC(O[Si](C)(C)C)=C2O13352.3Semi standard non polar33892256
1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone,1TMS,isomer #2CC(C)=CCCC1(C)C=CC2=C(CCC(=O)C3=CC=C(O)C=C3O[Si](C)(C)C)C=CC(O)=C2O13371.3Semi standard non polar33892256
1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone,1TMS,isomer #3CC(C)=CCCC1(C)C=CC2=C(CCC(=O)C3=CC=C(O[Si](C)(C)C)C=C3O)C=CC(O)=C2O13341.0Semi standard non polar33892256
1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone,2TMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(CCC(=O)C3=CC=C(O[Si](C)(C)C)C=C3O)C=CC(O[Si](C)(C)C)=C2O13267.5Semi standard non polar33892256
1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone,2TMS,isomer #2CC(C)=CCCC1(C)C=CC2=C(CCC(=O)C3=CC=C(O)C=C3O[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C2O13285.4Semi standard non polar33892256
1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone,2TMS,isomer #3CC(C)=CCCC1(C)C=CC2=C(CCC(=O)C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C=CC(O)=C2O13272.1Semi standard non polar33892256
1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone,3TMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(CCC(=O)C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C2O13259.9Semi standard non polar33892256
1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone,1TBDMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(CCC(=O)C3=CC=C(O)C=C3O)C=CC(O[Si](C)(C)C(C)(C)C)=C2O13592.5Semi standard non polar33892256
1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone,1TBDMS,isomer #2CC(C)=CCCC1(C)C=CC2=C(CCC(=O)C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)C=CC(O)=C2O13609.3Semi standard non polar33892256
1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone,1TBDMS,isomer #3CC(C)=CCCC1(C)C=CC2=C(CCC(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O)C=CC(O)=C2O13589.2Semi standard non polar33892256
1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone,2TBDMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(CCC(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O)C=CC(O[Si](C)(C)C(C)(C)C)=C2O13739.4Semi standard non polar33892256
1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone,2TBDMS,isomer #2CC(C)=CCCC1(C)C=CC2=C(CCC(=O)C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C2O13734.6Semi standard non polar33892256
1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone,2TBDMS,isomer #3CC(C)=CCCC1(C)C=CC2=C(CCC(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C=CC(O)=C2O13740.5Semi standard non polar33892256
1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone,3TBDMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(CCC(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C2O13911.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-7945000000-7c94f556497d9151e5142017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone GC-MS (3 TMS) - 70eV, Positivesplash10-053r-5072039000-ff1bffa8e870e6fb44162017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone 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 - 1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone 10V, Positive-QTOFsplash10-0a4i-1455900000-6d6788851bbf554d49c52016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone 20V, Positive-QTOFsplash10-000i-2950000000-5355f93232930302968a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone 40V, Positive-QTOFsplash10-00kr-5900000000-999302830c915dc449472016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone 10V, Negative-QTOFsplash10-0a4i-0111900000-bc305110dd2ee20e6a9e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone 20V, Negative-QTOFsplash10-0a4i-0866900000-7d72d0eecd0d8baee5152016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone 40V, Negative-QTOFsplash10-0a4i-1930000000-0044a6a750511a1de8862016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone 10V, Positive-QTOFsplash10-0a4i-0106900000-b28606f74f4282b1d5e52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone 20V, Positive-QTOFsplash10-05n0-1947200000-5fa44b5d921251a0c1ea2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone 40V, Positive-QTOFsplash10-000i-4932000000-3d28beb3049b09de5aef2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone 10V, Negative-QTOFsplash10-0a4i-0000900000-4232e56e7795651b99e42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone 20V, Negative-QTOFsplash10-0a4i-0402900000-a2c65807ae8f54eaaa642021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,4-Dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone 40V, Negative-QTOFsplash10-0a4l-5947000000-e8a99cce1c85d1a21a962021-09-22Wishart 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 IDFDB008610
KNApSAcK IDC00008019
Chemspider ID10272269
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21637213
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.. .