Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:57 UTC
Update Date2022-03-07 02:52:11 UTC
HMDB IDHMDB0029527
Secondary Accession Numbers
  • HMDB29527
Metabolite Identification
Common NameMelilotocarpan B
DescriptionMelilotocarpan B belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Thus, melilotocarpan b is considered to be a flavonoid. Based on a literature review very few articles have been published on Melilotocarpan B.
Structure
Data?1582753431
Synonyms
ValueSource
4,9-Dihydroxy-3-methoxypterocarpanHMDB
Chemical FormulaC16H14O5
Average Molecular Weight286.2794
Monoisotopic Molecular Weight286.084123558
IUPAC Name5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-6,14-diol
Traditional Namemelilotocarpan B
CAS Registry Number83013-83-6
SMILES
COC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(O)=C3)C1CO2
InChI Identifier
InChI=1S/C16H14O5/c1-19-12-5-4-10-15-11(7-20-16(10)14(12)18)9-3-2-8(17)6-13(9)21-15/h2-6,11,15,17-18H,7H2,1H3
InChI KeyQDFJNOVWEADTGJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassFuranoisoflavonoids
Direct ParentPterocarpans
Alternative Parents
Substituents
  • Isoflavanol
  • Pterocarpan
  • Isoflavan
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Coumaran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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 Point173 - 175.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.26 g/LALOGPS
logP2.63ALOGPS
logP2.21ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.03ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area68.15 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity75.04 m³·mol⁻¹ChemAxon
Polarizability29.21 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]+165.68831661259
DarkChem[M-H]-165.80731661259
DeepCCS[M+H]+170.48930932474
DeepCCS[M-H]-168.13130932474
DeepCCS[M-2H]-201.01730932474
DeepCCS[M+Na]+176.58230932474
AllCCS[M+H]+166.832859911
AllCCS[M+H-H2O]+163.132859911
AllCCS[M+NH4]+170.232859911
AllCCS[M+Na]+171.232859911
AllCCS[M-H]-170.232859911
AllCCS[M+Na-2H]-169.532859911
AllCCS[M+HCOO]-168.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Melilotocarpan BCOC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(O)=C3)C1CO23783.2Standard polar33892256
Melilotocarpan BCOC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(O)=C3)C1CO22571.1Standard non polar33892256
Melilotocarpan BCOC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(O)=C3)C1CO22801.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Melilotocarpan B,1TMS,isomer #1COC1=CC=C2C(=C1O[Si](C)(C)C)OCC1C3=CC=C(O)C=C3OC212683.3Semi standard non polar33892256
Melilotocarpan B,1TMS,isomer #2COC1=CC=C2C(=C1O)OCC1C3=CC=C(O[Si](C)(C)C)C=C3OC212738.2Semi standard non polar33892256
Melilotocarpan B,2TMS,isomer #1COC1=CC=C2C(=C1O[Si](C)(C)C)OCC1C3=CC=C(O[Si](C)(C)C)C=C3OC212705.1Semi standard non polar33892256
Melilotocarpan B,1TBDMS,isomer #1COC1=CC=C2C(=C1O[Si](C)(C)C(C)(C)C)OCC1C3=CC=C(O)C=C3OC212942.2Semi standard non polar33892256
Melilotocarpan B,1TBDMS,isomer #2COC1=CC=C2C(=C1O)OCC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OC213005.4Semi standard non polar33892256
Melilotocarpan B,2TBDMS,isomer #1COC1=CC=C2C(=C1O[Si](C)(C)C(C)(C)C)OCC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OC213190.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Melilotocarpan B GC-MS (Non-derivatized) - 70eV, Positivesplash10-059i-0490000000-339df8799be1aab5f4e42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Melilotocarpan B GC-MS (2 TMS) - 70eV, Positivesplash10-014i-5149700000-2f02118a036234eb69dd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Melilotocarpan B GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Melilotocarpan B 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 - Melilotocarpan B 10V, Positive-QTOFsplash10-000i-0590000000-2eedb9e50a93fccfd2702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Melilotocarpan B 20V, Positive-QTOFsplash10-000i-0790000000-c8ae12f7942777e4fec52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Melilotocarpan B 40V, Positive-QTOFsplash10-001i-9600000000-3f9ba7d7e74b17cbc5fa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Melilotocarpan B 10V, Negative-QTOFsplash10-000i-0090000000-0819975ba8e07288945d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Melilotocarpan B 20V, Negative-QTOFsplash10-000i-0090000000-7edbebc8d2d5199da1c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Melilotocarpan B 40V, Negative-QTOFsplash10-00ls-2930000000-608e1c9ced70e7592dac2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Melilotocarpan B 10V, Negative-QTOFsplash10-000i-0090000000-14912e1703be5edd027d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Melilotocarpan B 20V, Negative-QTOFsplash10-000i-0190000000-f5f231717c607b9c521e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Melilotocarpan B 40V, Negative-QTOFsplash10-03dr-3690000000-6eb54fe3322f6f14c04b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Melilotocarpan B 10V, Positive-QTOFsplash10-000i-0090000000-b239d41c6032c85540b22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Melilotocarpan B 20V, Positive-QTOFsplash10-000i-0490000000-589dcb73d78b023bbc5f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Melilotocarpan B 40V, Positive-QTOFsplash10-0002-1930000000-f7eaa74f742661eeab8d2021-09-24Wishart 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 IDFDB000667
KNApSAcK IDC00009997
Chemspider ID24843017
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44257459
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
Melilotocarpan B → 3,4,5-trihydroxy-6-({14-hydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-6-yl}oxy)oxane-2-carboxylic aciddetails
Melilotocarpan B → 3,4,5-trihydroxy-6-({6-hydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-14-yl}oxy)oxane-2-carboxylic aciddetails