Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:23:13 UTC
Update Date2022-03-07 02:55:37 UTC
HMDB IDHMDB0038102
Secondary Accession Numbers
  • HMDB38102
Metabolite Identification
Common Name(R)-Hispaglabridin A
Description(R)-Hispaglabridin A belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton (R)-Hispaglabridin A has been detected, but not quantified in, several different foods, such as green tea, herbal tea, black tea, herbs and spices, and red tea. This could make (R)-hispaglabridin a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (R)-Hispaglabridin A.
Structure
Data?1563863140
Synonyms
ValueSource
Hispaglabridin aHMDB
Chemical FormulaC25H28O4
Average Molecular Weight392.4874
Monoisotopic Molecular Weight392.198759384
IUPAC Name4-{12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8,13-tetraen-5-yl}-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol
Traditional Name4-{12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8,13-tetraen-5-yl}-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol
CAS Registry Number68978-03-0
SMILES
CC(C)=CCC1=C(O)C=CC(C2COC3=C(C2)C=CC2=C3C=CC(C)(C)O2)=C1O
InChI Identifier
InChI=1S/C25H28O4/c1-15(2)5-7-19-21(26)9-8-18(23(19)27)17-13-16-6-10-22-20(24(16)28-14-17)11-12-25(3,4)29-22/h5-6,8-12,17,26-27H,7,13-14H2,1-4H3
InChI KeyHZHXMXSXYQCAIG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassPyranoisoflavonoids
Direct ParentPyranoisoflavonoids
Alternative Parents
Substituents
  • Pyranoisoflavonoid
  • Hydroxyisoflavonoid
  • Isoflavanol
  • Isoflavan
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 Point132 - 133 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0035 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0011 g/LALOGPS
logP5.18ALOGPS
logP5.82ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)9.32ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity117.6 m³·mol⁻¹ChemAxon
Polarizability44.22 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+197.82631661259
DarkChem[M-H]-192.50231661259
DeepCCS[M+H]+194.72830932474
DeepCCS[M-H]-192.3730932474
DeepCCS[M-2H]-226.29630932474
DeepCCS[M+Na]+201.52430932474
AllCCS[M+H]+200.532859911
AllCCS[M+H-H2O]+197.632859911
AllCCS[M+NH4]+203.132859911
AllCCS[M+Na]+203.932859911
AllCCS[M-H]-199.632859911
AllCCS[M+Na-2H]-199.732859911
AllCCS[M+HCOO]-200.132859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.8.82 minutes32390414
Predicted by Siyang on May 30, 202217.0164 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.21 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid28.4 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid3028.3 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid330.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid229.8 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid173.3 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid168.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid866.6 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid766.2 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)86.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1623.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid685.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1328.3 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid573.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid473.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate268.4 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA290.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water8.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-Hispaglabridin ACC(C)=CCC1=C(O)C=CC(C2COC3=C(C2)C=CC2=C3C=CC(C)(C)O2)=C1O4177.6Standard polar33892256
(R)-Hispaglabridin ACC(C)=CCC1=C(O)C=CC(C2COC3=C(C2)C=CC2=C3C=CC(C)(C)O2)=C1O3163.7Standard non polar33892256
(R)-Hispaglabridin ACC(C)=CCC1=C(O)C=CC(C2COC3=C(C2)C=CC2=C3C=CC(C)(C)O2)=C1O3461.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-Hispaglabridin A,1TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=CC(C2COC3=C(C=CC4=C3C=CC(C)(C)O4)C2)=C1O3181.2Semi standard non polar33892256
(R)-Hispaglabridin A,1TMS,isomer #2CC(C)=CCC1=C(O)C=CC(C2COC3=C(C=CC4=C3C=CC(C)(C)O4)C2)=C1O[Si](C)(C)C3155.6Semi standard non polar33892256
(R)-Hispaglabridin A,2TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=CC(C2COC3=C(C=CC4=C3C=CC(C)(C)O4)C2)=C1O[Si](C)(C)C3102.5Semi standard non polar33892256
(R)-Hispaglabridin A,1TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2COC3=C(C=CC4=C3C=CC(C)(C)O4)C2)=C1O3426.5Semi standard non polar33892256
(R)-Hispaglabridin A,1TBDMS,isomer #2CC(C)=CCC1=C(O)C=CC(C2COC3=C(C=CC4=C3C=CC(C)(C)O4)C2)=C1O[Si](C)(C)C(C)(C)C3395.8Semi standard non polar33892256
(R)-Hispaglabridin A,2TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2COC3=C(C=CC4=C3C=CC(C)(C)O4)C2)=C1O[Si](C)(C)C(C)(C)C3522.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Hispaglabridin A GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-2219000000-a4e3325ed2f7f79ad8fa2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Hispaglabridin A GC-MS (2 TMS) - 70eV, Positivesplash10-00di-3005590000-0b5230e41e8ae2ab2a752017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Hispaglabridin A 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 - (R)-Hispaglabridin A 10V, Positive-QTOFsplash10-000l-1709000000-0ed3e15b4b24770f77762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 20V, Positive-QTOFsplash10-000i-2938000000-6676cb29bd9423cc9e182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 40V, Positive-QTOFsplash10-00ks-3920000000-04df62888c77ab7fa9a42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 10V, Negative-QTOFsplash10-0006-0219000000-087de2f429549d436dbb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 20V, Negative-QTOFsplash10-00p3-0958000000-593fa8e9856ddf15519a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 40V, Negative-QTOFsplash10-0kl9-0922000000-72064c560c7b5d72e5642016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 10V, Positive-QTOFsplash10-000i-0029000000-1a83a6b9dedc8868beaa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 20V, Positive-QTOFsplash10-000i-0219000000-c9561e8f3fea2f732c5a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 40V, Positive-QTOFsplash10-0550-2987000000-13f9084eeec9d0f1abb82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 10V, Negative-QTOFsplash10-0006-0009000000-fc8307e58aa68e585da32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 20V, Negative-QTOFsplash10-0006-0009000000-0c85109cd9f3a11f33c02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 40V, Negative-QTOFsplash10-052r-1915000000-1b6b30c7b8401382cf932021-09-22Wishart 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 IDFDB017324
KNApSAcK IDC00002534
Chemspider ID3682060
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4484221
PDB IDNot Available
ChEBI ID175139
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1865781
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.. .