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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:00 UTC
Update Date2022-03-07 02:52:37 UTC
HMDB IDHMDB0030620
Secondary Accession Numbers
  • HMDB30620
Metabolite Identification
Common NameMorusinol
DescriptionMorusinol, also known as oxyhydromorusin, belongs to the class of organic compounds known as 3-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3-position. Thus, morusinol is considered to be a flavonoid. Based on a literature review very few articles have been published on Morusinol.
Structure
Data?1563862013
Synonyms
ValueSource
OxyhydromorusinKegg
2-(2,4-Dihydroxyphenyl)-5-hydroxy-3-(3-hydroxy-3-methylbutyl)-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-oneHMDB
2-(2,4-Dihydroxyphenyl)-5-hydroxy-3-(3-hydroxy-3-methylbutyl)-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one, 9ciHMDB
OxydihydromorusinHMDB
Chemical FormulaC25H26O7
Average Molecular Weight438.4697
Monoisotopic Molecular Weight438.167853186
IUPAC Name2-(2,4-dihydroxyphenyl)-5-hydroxy-3-(3-hydroxy-3-methylbutyl)-8,8-dimethyl-4H,8H-pyrano[2,3-h]chromen-4-one
Traditional Nameoxydihydromorusin
CAS Registry Number62949-93-3
SMILES
CC(C)(O)CCC1=C(OC2=C(C(O)=CC3=C2C=CC(C)(C)O3)C1=O)C1=C(O)C=C(O)C=C1
InChI Identifier
InChI=1S/C25H26O7/c1-24(2,30)9-7-16-21(29)20-18(28)12-19-15(8-10-25(3,4)32-19)23(20)31-22(16)14-6-5-13(26)11-17(14)27/h5-6,8,10-12,26-28,30H,7,9H2,1-4H3
InChI KeyAFOKZNPZDXHDHD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct Parent3-prenylated flavones
Alternative Parents
Substituents
  • 3-prenylated flavone
  • Pyranoflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Hydroxyflavonoid
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Phenol
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Tertiary alcohol
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • 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 Point215 - 216 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.49 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0083 g/LALOGPS
logP4.19ALOGPS
logP4.15ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)8.05ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity121.85 m³·mol⁻¹ChemAxon
Polarizability46.71 ųChemAxon
Number of Rings4ChemAxon
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]+201.85831661259
DarkChem[M-H]-198.77331661259
DeepCCS[M+H]+206.55330932474
DeepCCS[M-H]-204.15830932474
DeepCCS[M-2H]-237.04130932474
DeepCCS[M+Na]+212.46630932474
AllCCS[M+H]+204.732859911
AllCCS[M+H-H2O]+202.232859911
AllCCS[M+NH4]+207.032859911
AllCCS[M+Na]+207.732859911
AllCCS[M-H]-210.032859911
AllCCS[M+Na-2H]-210.532859911
AllCCS[M+HCOO]-211.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MorusinolCC(C)(O)CCC1=C(OC2=C(C(O)=CC3=C2C=CC(C)(C)O3)C1=O)C1=C(O)C=C(O)C=C15073.8Standard polar33892256
MorusinolCC(C)(O)CCC1=C(OC2=C(C(O)=CC3=C2C=CC(C)(C)O3)C1=O)C1=C(O)C=C(O)C=C13634.3Standard non polar33892256
MorusinolCC(C)(O)CCC1=C(OC2=C(C(O)=CC3=C2C=CC(C)(C)O3)C1=O)C1=C(O)C=C(O)C=C13912.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Morusinol,1TMS,isomer #1CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O)C=C2O)=C(CCC(C)(C)O[Si](C)(C)C)C3=O)O13691.5Semi standard non polar33892256
Morusinol,1TMS,isomer #2CC(C)(O)CCC1=C(C2=CC=C(O)C=C2O)OC2=C3C=CC(C)(C)OC3=CC(O[Si](C)(C)C)=C2C1=O3593.2Semi standard non polar33892256
Morusinol,1TMS,isomer #3CC(C)(O)CCC1=C(C2=CC=C(O)C=C2O[Si](C)(C)C)OC2=C3C=CC(C)(C)OC3=CC(O)=C2C1=O3558.6Semi standard non polar33892256
Morusinol,1TMS,isomer #4CC(C)(O)CCC1=C(C2=CC=C(O[Si](C)(C)C)C=C2O)OC2=C3C=CC(C)(C)OC3=CC(O)=C2C1=O3582.1Semi standard non polar33892256
Morusinol,2TMS,isomer #1CC1(C)C=CC2=C(C=C(O[Si](C)(C)C)C3=C2OC(C2=CC=C(O)C=C2O)=C(CCC(C)(C)O[Si](C)(C)C)C3=O)O13574.8Semi standard non polar33892256
Morusinol,2TMS,isomer #2CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O[Si](C)(C)C)C=C2O)=C(CCC(C)(C)O[Si](C)(C)C)C3=O)O13563.6Semi standard non polar33892256
Morusinol,2TMS,isomer #3CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O)C=C2O[Si](C)(C)C)=C(CCC(C)(C)O[Si](C)(C)C)C3=O)O13543.3Semi standard non polar33892256
Morusinol,2TMS,isomer #4CC(C)(O)CCC1=C(C2=CC=C(O[Si](C)(C)C)C=C2O)OC2=C3C=CC(C)(C)OC3=CC(O[Si](C)(C)C)=C2C1=O3489.8Semi standard non polar33892256
Morusinol,2TMS,isomer #5CC(C)(O)CCC1=C(C2=CC=C(O)C=C2O[Si](C)(C)C)OC2=C3C=CC(C)(C)OC3=CC(O[Si](C)(C)C)=C2C1=O3463.7Semi standard non polar33892256
Morusinol,2TMS,isomer #6CC(C)(O)CCC1=C(C2=CC=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)OC2=C3C=CC(C)(C)OC3=CC(O)=C2C1=O3469.1Semi standard non polar33892256
Morusinol,3TMS,isomer #1CC1(C)C=CC2=C(C=C(O[Si](C)(C)C)C3=C2OC(C2=CC=C(O[Si](C)(C)C)C=C2O)=C(CCC(C)(C)O[Si](C)(C)C)C3=O)O13491.1Semi standard non polar33892256
Morusinol,3TMS,isomer #2CC1(C)C=CC2=C(C=C(O[Si](C)(C)C)C3=C2OC(C2=CC=C(O)C=C2O[Si](C)(C)C)=C(CCC(C)(C)O[Si](C)(C)C)C3=O)O13462.3Semi standard non polar33892256
Morusinol,3TMS,isomer #3CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)=C(CCC(C)(C)O[Si](C)(C)C)C3=O)O13472.1Semi standard non polar33892256
Morusinol,3TMS,isomer #4CC(C)(O)CCC1=C(C2=CC=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)OC2=C3C=CC(C)(C)OC3=CC(O[Si](C)(C)C)=C2C1=O3420.0Semi standard non polar33892256
Morusinol,4TMS,isomer #1CC1(C)C=CC2=C(C=C(O[Si](C)(C)C)C3=C2OC(C2=CC=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)=C(CCC(C)(C)O[Si](C)(C)C)C3=O)O13483.2Semi standard non polar33892256
Morusinol,1TBDMS,isomer #1CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O)C=C2O)=C(CCC(C)(C)O[Si](C)(C)C(C)(C)C)C3=O)O13965.5Semi standard non polar33892256
Morusinol,1TBDMS,isomer #2CC(C)(O)CCC1=C(C2=CC=C(O)C=C2O)OC2=C3C=CC(C)(C)OC3=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O3839.8Semi standard non polar33892256
Morusinol,1TBDMS,isomer #3CC(C)(O)CCC1=C(C2=CC=C(O)C=C2O[Si](C)(C)C(C)(C)C)OC2=C3C=CC(C)(C)OC3=CC(O)=C2C1=O3809.1Semi standard non polar33892256
Morusinol,1TBDMS,isomer #4CC(C)(O)CCC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O)OC2=C3C=CC(C)(C)OC3=CC(O)=C2C1=O3836.1Semi standard non polar33892256
Morusinol,2TBDMS,isomer #1CC1(C)C=CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2OC(C2=CC=C(O)C=C2O)=C(CCC(C)(C)O[Si](C)(C)C(C)(C)C)C3=O)O14057.9Semi standard non polar33892256
Morusinol,2TBDMS,isomer #2CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O)=C(CCC(C)(C)O[Si](C)(C)C(C)(C)C)C3=O)O14078.9Semi standard non polar33892256
Morusinol,2TBDMS,isomer #3CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O)C=C2O[Si](C)(C)C(C)(C)C)=C(CCC(C)(C)O[Si](C)(C)C(C)(C)C)C3=O)O14038.5Semi standard non polar33892256
Morusinol,2TBDMS,isomer #4CC(C)(O)CCC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O)OC2=C3C=CC(C)(C)OC3=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O3948.5Semi standard non polar33892256
Morusinol,2TBDMS,isomer #5CC(C)(O)CCC1=C(C2=CC=C(O)C=C2O[Si](C)(C)C(C)(C)C)OC2=C3C=CC(C)(C)OC3=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O3904.3Semi standard non polar33892256
Morusinol,2TBDMS,isomer #6CC(C)(O)CCC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)OC2=C3C=CC(C)(C)OC3=CC(O)=C2C1=O3929.3Semi standard non polar33892256
Morusinol,3TBDMS,isomer #1CC1(C)C=CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2OC(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O)=C(CCC(C)(C)O[Si](C)(C)C(C)(C)C)C3=O)O14146.1Semi standard non polar33892256
Morusinol,3TBDMS,isomer #2CC1(C)C=CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2OC(C2=CC=C(O)C=C2O[Si](C)(C)C(C)(C)C)=C(CCC(C)(C)O[Si](C)(C)C(C)(C)C)C3=O)O14093.6Semi standard non polar33892256
Morusinol,3TBDMS,isomer #3CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)=C(CCC(C)(C)O[Si](C)(C)C(C)(C)C)C3=O)O14145.1Semi standard non polar33892256
Morusinol,3TBDMS,isomer #4CC(C)(O)CCC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)OC2=C3C=CC(C)(C)OC3=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O4033.9Semi standard non polar33892256
Morusinol,4TBDMS,isomer #1CC1(C)C=CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2OC(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)=C(CCC(C)(C)O[Si](C)(C)C(C)(C)C)C3=O)O14275.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Morusinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-9014800000-aedd5a44524f344097b22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Morusinol GC-MS (3 TMS) - 70eV, Positivesplash10-001c-3200049000-786e629c1d14b93f2e692017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Morusinol 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 - Morusinol 10V, Positive-QTOFsplash10-00di-0003900000-ba7a9d315739acc3a5562016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Morusinol 20V, Positive-QTOFsplash10-01b9-2009500000-35b2bcadb4bd76f3274f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Morusinol 40V, Positive-QTOFsplash10-014i-3049000000-f9a6fdf1c8706ed57e2b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Morusinol 10V, Negative-QTOFsplash10-000i-0001900000-517c33b6c97babb249862016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Morusinol 20V, Negative-QTOFsplash10-00kr-0005900000-bddab33210b64129faaf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Morusinol 40V, Negative-QTOFsplash10-0pb9-2629100000-59a684f0d2653b654d962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Morusinol 10V, Positive-QTOFsplash10-000i-0000900000-b5f2afccea7aeee35d792021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Morusinol 20V, Positive-QTOFsplash10-000i-0000900000-b5f2afccea7aeee35d792021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Morusinol 40V, Positive-QTOFsplash10-01bi-0090400000-e087627855ec79e516162021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Morusinol 10V, Negative-QTOFsplash10-000i-0000900000-c34e42b820ea6128d4112021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Morusinol 20V, Negative-QTOFsplash10-000i-0000900000-c34e42b820ea6128d4112021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Morusinol 40V, Negative-QTOFsplash10-03y0-0190100000-483e620f5238451bf6c12021-09-23Wishart 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 IDFDB002518
KNApSAcK IDC00004059
Chemspider ID4587696
KEGG Compound IDC17868
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5481968
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1821481
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.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Morusinol → 3,4,5-trihydroxy-6-{3-hydroxy-4-[5-hydroxy-3-(3-hydroxy-3-methylbutyl)-8,8-dimethyl-4-oxo-4H,8H-pyrano[2,3-f]chromen-2-yl]phenoxy}oxane-2-carboxylic aciddetails
Morusinol → 3,4,5-trihydroxy-6-{5-hydroxy-2-[5-hydroxy-3-(3-hydroxy-3-methylbutyl)-8,8-dimethyl-4-oxo-4H,8H-pyrano[2,3-f]chromen-2-yl]phenoxy}oxane-2-carboxylic aciddetails
Morusinol → 6-{[2-(2,4-dihydroxyphenyl)-3-(3-hydroxy-3-methylbutyl)-8,8-dimethyl-4-oxo-4H,8H-pyrano[2,3-f]chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails