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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:01:27 UTC
Update Date2022-03-07 02:53:39 UTC
HMDB IDHMDB0033310
Secondary Accession Numbers
  • HMDB33310
Metabolite Identification
Common NameMoracin C
DescriptionMoracin C belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Moracin C has been detected, but not quantified in, fruits and mulberries (Morus). This could make moracin C a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Moracin C.
Structure
Data?1563862385
Synonyms
ValueSource
2-(3,5-Dihydroxy-4-prenylphenyl)-6-hydroxybenzofuranHMDB
5-(6-Hydroxy-2-benzofuranyl)-2-(3-methyl-2-butenyl)-1,3-benzenediol, 9ciHMDB
Moracin NMeSH
Moracin CMeSH
Chemical FormulaC19H18O4
Average Molecular Weight310.3438
Monoisotopic Molecular Weight310.120509064
IUPAC Name5-(6-hydroxy-1-benzofuran-2-yl)-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol
Traditional Name5-(6-hydroxy-1-benzofuran-2-yl)-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol
CAS Registry Number69120-06-5
SMILES
CC(C)=CCC1=C(O)C=C(C=C1O)C1=CC2=CC=C(O)C=C2O1
InChI Identifier
InChI=1S/C19H18O4/c1-11(2)3-6-15-16(21)7-13(8-17(15)22)18-9-12-4-5-14(20)10-19(12)23-18/h3-5,7-10,20-22H,6H2,1-2H3
InChI KeyZTGHWUWBQNCCOH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
Class2-arylbenzofuran flavonoids
Sub ClassNot Available
Direct Parent2-arylbenzofuran flavonoids
Alternative Parents
Substituents
  • 2-arylbenzofuran flavonoid
  • 4'-prenylated 2-arybenzofuran
  • 2-phenylbenzofuran
  • Phenylbenzofuran
  • Benzofuran
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point198 - 199 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.065 g/LALOGPS
logP4.07ALOGPS
logP4.52ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.5ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity90.1 m³·mol⁻¹ChemAxon
Polarizability34.89 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]+176.19531661259
DarkChem[M-H]-174.631661259
DeepCCS[M+H]+171.96630932474
DeepCCS[M-H]-169.60830932474
DeepCCS[M-2H]-202.49330932474
DeepCCS[M+Na]+178.05930932474
AllCCS[M+H]+175.832859911
AllCCS[M+H-H2O]+172.332859911
AllCCS[M+NH4]+179.132859911
AllCCS[M+Na]+180.132859911
AllCCS[M-H]-174.032859911
AllCCS[M+Na-2H]-173.432859911
AllCCS[M+HCOO]-172.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Moracin CCC(C)=CCC1=C(O)C=C(C=C1O)C1=CC2=CC=C(O)C=C2O14872.7Standard polar33892256
Moracin CCC(C)=CCC1=C(O)C=C(C=C1O)C1=CC2=CC=C(O)C=C2O12848.2Standard non polar33892256
Moracin CCC(C)=CCC1=C(O)C=C(C=C1O)C1=CC2=CC=C(O)C=C2O13139.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Moracin C,1TMS,isomer #1CC(C)=CCC1=C(O)C=C(C2=CC3=CC=C(O)C=C3O2)C=C1O[Si](C)(C)C3102.0Semi standard non polar33892256
Moracin C,1TMS,isomer #2CC(C)=CCC1=C(O)C=C(C2=CC3=CC=C(O[Si](C)(C)C)C=C3O2)C=C1O3156.6Semi standard non polar33892256
Moracin C,2TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=C(C2=CC3=CC=C(O)C=C3O2)C=C1O[Si](C)(C)C2987.7Semi standard non polar33892256
Moracin C,2TMS,isomer #2CC(C)=CCC1=C(O)C=C(C2=CC3=CC=C(O[Si](C)(C)C)C=C3O2)C=C1O[Si](C)(C)C3010.9Semi standard non polar33892256
Moracin C,3TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=C(C2=CC3=CC=C(O[Si](C)(C)C)C=C3O2)C=C1O[Si](C)(C)C2995.3Semi standard non polar33892256
Moracin C,1TBDMS,isomer #1CC(C)=CCC1=C(O)C=C(C2=CC3=CC=C(O)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C3410.1Semi standard non polar33892256
Moracin C,1TBDMS,isomer #2CC(C)=CCC1=C(O)C=C(C2=CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1O3437.4Semi standard non polar33892256
Moracin C,2TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(C2=CC3=CC=C(O)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C3534.9Semi standard non polar33892256
Moracin C,2TBDMS,isomer #2CC(C)=CCC1=C(O)C=C(C2=CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C3545.1Semi standard non polar33892256
Moracin C,3TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(C2=CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C3688.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Moracin C EI-B (Non-derivatized)splash10-08fr-0195000000-f50993107453383214aa2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Moracin C CI-B (Non-derivatized)splash10-08fr-0359000000-9f5599858c3313acc0a02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Moracin C EI-B (Non-derivatized)splash10-08fr-0195000000-f50993107453383214aa2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Moracin C CI-B (Non-derivatized)splash10-08fr-0359000000-9f5599858c3313acc0a02018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Moracin C GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-4391000000-4435ccef56eab39060992017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Moracin C GC-MS (3 TMS) - 70eV, Positivesplash10-03di-3100790000-52e4e8b2198fed137fc62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Moracin C GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Moracin C 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 - Moracin C 10V, Positive-QTOFsplash10-03di-0039000000-478e6b82be8424a570a82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moracin C 20V, Positive-QTOFsplash10-0900-4194000000-f08baf35c3dd0f59c3792016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moracin C 40V, Positive-QTOFsplash10-0ldi-9460000000-8b569b526ce509350ff32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moracin C 10V, Negative-QTOFsplash10-0a4i-0009000000-95ff2d0d171dc5ee25572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moracin C 20V, Negative-QTOFsplash10-0a4i-0039000000-475ae14c8c4b60e932d92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moracin C 40V, Negative-QTOFsplash10-0006-3490000000-157379c6ed73e09e6c872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moracin C 10V, Positive-QTOFsplash10-0a4i-0093000000-596da4dd1f763e92a8732021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moracin C 20V, Positive-QTOFsplash10-0a4i-0090000000-50f1c5af804e390722d52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moracin C 40V, Positive-QTOFsplash10-0fi0-0490000000-c6a78ac1b15432f920572021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moracin C 10V, Negative-QTOFsplash10-0a4i-0009000000-a5477ba8add3d375c0082021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moracin C 20V, Negative-QTOFsplash10-0a4i-0049000000-4bfcd65e12593d5263622021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moracin C 40V, Negative-QTOFsplash10-0a4j-1980000000-65f9c3f6a87ffaeba4112021-09-24Wishart 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 IDFDB011334
KNApSAcK IDC00036149
Chemspider ID136764
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound155248
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.. .

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
Moracin C → 6-({2-[3,5-dihydroxy-4-(3-methylbut-2-en-1-yl)phenyl]-1-benzofuran-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Moracin C → 3,4,5-trihydroxy-6-[3-hydroxy-5-(6-hydroxy-1-benzofuran-2-yl)-2-(3-methylbut-2-en-1-yl)phenoxy]oxane-2-carboxylic aciddetails