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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:47:59 UTC
Update Date2022-03-07 02:53:57 UTC
HMDB IDHMDB0034025
Secondary Accession Numbers
  • HMDB34025
Metabolite Identification
Common NameCristacarpin
DescriptionCristacarpin 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, cristacarpin is considered to be a flavonoid. Based on a literature review a significant number of articles have been published on Cristacarpin.
Structure
Data?1563862497
Synonyms
ValueSource
3,6a-Dihydroxy-9-methoxy-10-prenylpterocarpanHMDB
Erythrabyssin IHMDB
Chemical FormulaC21H22O5
Average Molecular Weight354.3964
Monoisotopic Molecular Weight354.146723814
IUPAC Name14-methoxy-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,10-diol
Traditional Name14-methoxy-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,10-diol
CAS Registry Number74515-47-2
SMILES
COC1=C(CC=C(C)C)C2=C(C=C1)C1(O)COC3=C(C=CC(O)=C3)C1O2
InChI Identifier
InChI=1S/C21H22O5/c1-12(2)4-6-14-17(24-3)9-8-16-19(14)26-20-15-7-5-13(22)10-18(15)25-11-21(16,20)23/h4-5,7-10,20,22-23H,6,11H2,1-3H3
InChI KeyZHPYEBFYLDGZKF-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
  • Pterocarpan
  • Isoflavanol
  • Isoflavan
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Coumaran
  • Benzofuran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
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 Solubility0.044 g/LALOGPS
logP3.19ALOGPS
logP3.58ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)9.41ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area68.15 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity98.39 m³·mol⁻¹ChemAxon
Polarizability38.25 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]+183.20631661259
DarkChem[M-H]-183.33731661259
DeepCCS[M+H]+188.54930932474
DeepCCS[M-H]-186.19130932474
DeepCCS[M-2H]-220.12230932474
DeepCCS[M+Na]+195.63830932474
AllCCS[M+H]+186.532859911
AllCCS[M+H-H2O]+183.432859911
AllCCS[M+NH4]+189.432859911
AllCCS[M+Na]+190.232859911
AllCCS[M-H]-190.432859911
AllCCS[M+Na-2H]-190.132859911
AllCCS[M+HCOO]-190.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CristacarpinCOC1=C(CC=C(C)C)C2=C(C=C1)C1(O)COC3=C(C=CC(O)=C3)C1O24068.8Standard polar33892256
CristacarpinCOC1=C(CC=C(C)C)C2=C(C=C1)C1(O)COC3=C(C=CC(O)=C3)C1O22892.2Standard non polar33892256
CristacarpinCOC1=C(CC=C(C)C)C2=C(C=C1)C1(O)COC3=C(C=CC(O)=C3)C1O23112.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cristacarpin,1TMS,isomer #1COC1=CC=C2C(=C1CC=C(C)C)OC1C3=CC=C(O)C=C3OCC21O[Si](C)(C)C2928.3Semi standard non polar33892256
Cristacarpin,1TMS,isomer #2COC1=CC=C2C(=C1CC=C(C)C)OC1C3=CC=C(O[Si](C)(C)C)C=C3OCC21O2995.6Semi standard non polar33892256
Cristacarpin,2TMS,isomer #1COC1=CC=C2C(=C1CC=C(C)C)OC1C3=CC=C(O[Si](C)(C)C)C=C3OCC21O[Si](C)(C)C2959.8Semi standard non polar33892256
Cristacarpin,1TBDMS,isomer #1COC1=CC=C2C(=C1CC=C(C)C)OC1C3=CC=C(O)C=C3OCC21O[Si](C)(C)C(C)(C)C3165.8Semi standard non polar33892256
Cristacarpin,1TBDMS,isomer #2COC1=CC=C2C(=C1CC=C(C)C)OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OCC21O3213.8Semi standard non polar33892256
Cristacarpin,2TBDMS,isomer #1COC1=CC=C2C(=C1CC=C(C)C)OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OCC21O[Si](C)(C)C(C)(C)C3400.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cristacarpin GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-2719000000-8204135af40c2a67f3632017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cristacarpin GC-MS (2 TMS) - 70eV, Positivesplash10-003r-2110900000-217ac92673d79ce2face2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cristacarpin 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 - Cristacarpin 10V, Positive-QTOFsplash10-0a4l-0809000000-1f20865deee1b7e9153d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cristacarpin 20V, Positive-QTOFsplash10-0avj-4349000000-9c34c1a8cc9673260ecb2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cristacarpin 40V, Positive-QTOFsplash10-084i-4900000000-ef53acc4d8643ed883d02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cristacarpin 10V, Negative-QTOFsplash10-0udi-0009000000-dbe043a3172b38e4db9a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cristacarpin 20V, Negative-QTOFsplash10-0udi-0019000000-59cde98f51d505202b872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cristacarpin 40V, Negative-QTOFsplash10-0a4i-3933000000-01ad04fb7f953c6bdbef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cristacarpin 10V, Positive-QTOFsplash10-0a4j-0079000000-0f9b3b267b029f9963382021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cristacarpin 20V, Positive-QTOFsplash10-0002-0092000000-5a8c7ec5d650142992fe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cristacarpin 40V, Positive-QTOFsplash10-0wnd-6967000000-8b791612f4ed906e84532021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cristacarpin 10V, Negative-QTOFsplash10-0udi-0009000000-76b5b50d40f0609ef17e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cristacarpin 20V, Negative-QTOFsplash10-0udi-0009000000-51190ce90ba56e3e567e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cristacarpin 40V, Negative-QTOFsplash10-0udi-0259000000-7f5cb8a933ef580e77542021-09-23Wishart 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 IDNot Available
KNApSAcK IDC00002515
Chemspider ID112441
KEGG Compound IDC10206
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound126540
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.. .