Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:32:39 UTC
Update Date2022-03-07 02:53:51 UTC
HMDB IDHMDB0033782
Secondary Accession Numbers
  • HMDB33782
Metabolite Identification
Common NameBergamottin
DescriptionBergamottin is found in citrus. Bergamottin is a constituent of bergamot oil. Also from lemon oil and oils of other Citrus species and carrot (Daucus carota) Bergamottin is a natural furanocoumarin found principally in grapefruit juice. It is also found in the oil of bergamot, from which it was first isolated and from which its name is derived. To a lesser extent, bergamottin is also present in the essential oils of other citrus fruits. Along with the chemically related compound 6 ,7 -dihydroxybergamottin, it is believed to be responsible for the grapefruit juice effect in which the consumption of the juice affects the metabolism of a variety of pharmaceutical drugs
Structure
Data?1563862459
Synonyms
ValueSource
4-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one, 9ciHMDB
5-GeranoxypsoralenHMDB
5-GeranyloxypsoralenHMDB
BergamotinHMDB
BergamotineHMDB
BergaptinHMDB
Bergaptol geranyl etherHMDB
Chemical FormulaC21H22O4
Average Molecular Weight338.403
Monoisotopic Molecular Weight338.151809188
IUPAC Name4-{[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one
Traditional Name4-{[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]oxy}furo[3,2-g]chromen-7-one
CAS Registry Number7380-40-7
SMILES
CC(C)=CCC\C(C)=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O2
InChI Identifier
InChI=1S/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-16-7-8-20(22)25-19(16)13-18-17(21)10-12-23-18/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9-
InChI KeyDBMJZOMNXBSRED-DHDCSXOGSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • Linear furanocoumarin
  • Furanocoumarin
  • Psoralen
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Monoterpenoid
  • Aromatic monoterpenoid
  • Benzofuran
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point59 - 61 °CNot Available
Boiling Point503.00 to 504.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.034 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.382 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP5.3ALOGPS
logP4.81ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area48.67 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity99.77 m³·mol⁻¹ChemAxon
Polarizability37.47 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+180.77331661259
DarkChem[M-H]-179.0431661259
DeepCCS[M+H]+182.58430932474
DeepCCS[M-H]-180.22630932474
DeepCCS[M-2H]-213.56830932474
DeepCCS[M+Na]+188.84830932474
AllCCS[M+H]+182.032859911
AllCCS[M+H-H2O]+179.032859911
AllCCS[M+NH4]+184.832859911
AllCCS[M+Na]+185.632859911
AllCCS[M-H]-185.732859911
AllCCS[M+Na-2H]-185.032859911
AllCCS[M+HCOO]-184.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BergamottinCC(C)=CCC\C(C)=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O23648.3Standard polar33892256
BergamottinCC(C)=CCC\C(C)=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O22816.9Standard non polar33892256
BergamottinCC(C)=CCC\C(C)=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O22911.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bergamottin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gi0-9563000000-1489fb332877b94837152017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bergamottin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bergamottin 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 - Bergamottin 10V, Positive-QTOFsplash10-000i-1449000000-f1cb80e88623323efd782017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergamottin 20V, Positive-QTOFsplash10-00kr-7974000000-8dc8885c8ce63b6b8f052017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergamottin 40V, Positive-QTOFsplash10-0uxr-9420000000-d4a732b567f78ee66d362017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergamottin 10V, Negative-QTOFsplash10-000i-0059000000-6c5381fc4c44ea7b815b2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergamottin 20V, Negative-QTOFsplash10-0udi-0392000000-aef5d498f581369a14952017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergamottin 40V, Negative-QTOFsplash10-0a4i-0910000000-f3479b11ac7337bdd5d42017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergamottin 10V, Positive-QTOFsplash10-0udi-0090000000-2e5a86e101fa40f235c92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergamottin 20V, Positive-QTOFsplash10-0udi-1090000000-f45a823c8a5c19aa49142021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergamottin 40V, Positive-QTOFsplash10-0fb9-6960000000-6c6cb6ea0377f6b535b72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergamottin 10V, Negative-QTOFsplash10-000i-0019000000-3816dc9471dd695014e52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergamottin 20V, Negative-QTOFsplash10-000i-1897000000-825739cf6e0dc17d5b812021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergamottin 40V, Negative-QTOFsplash10-0zfr-2980000000-b70406757f87828a48a02021-09-22Wishart 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 IDFDB011939
KNApSAcK IDC00047753
Chemspider ID5584831
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBergamottin
METLIN IDNot Available
PubChem Compound7251175
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1012211
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hwang YP, Yun HJ, Choi JH, Kang KW, Jeong HG: Suppression of phorbol-12-myristate-13-acetate-induced tumor cell invasion by bergamottin via the inhibition of protein kinase Cdelta/p38 mitogen-activated protein kinase and JNK/nuclear factor-kappaB-dependent matrix metalloproteinase-9 expression. Mol Nutr Food Res. 2010 Jul;54(7):977-90. doi: 10.1002/mnfr.200900283. [PubMed:19943262 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .