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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:18 UTC
Update Date2022-03-07 02:52:38 UTC
HMDB IDHMDB0030666
Secondary Accession Numbers
  • HMDB30666
Metabolite Identification
Common NameChalepin acetate
DescriptionChalepin acetate, also known as rutamarin, belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. Based on a literature review very few articles have been published on Chalepin acetate.
Structure
Data?1563862020
Synonyms
ValueSource
Chalepin acetic acidGenerator
RutamarinHMDB
2-[6-(2-Methylbut-3-en-2-yl)-7-oxo-2H,3H,7H-furo[3,2-g]chromen-2-yl]propan-2-yl acetic acidHMDB
Chemical FormulaC21H24O5
Average Molecular Weight356.4123
Monoisotopic Molecular Weight356.162373878
IUPAC Name2-[6-(2-methylbut-3-en-2-yl)-7-oxo-2H,3H,7H-furo[3,2-g]chromen-2-yl]propan-2-yl acetate
Traditional Name2-[6-(2-methylbut-3-en-2-yl)-7-oxo-2H,3H-furo[3,2-g]chromen-2-yl]propan-2-yl acetate
CAS Registry Number14882-94-1
SMILES
CC(=O)OC(C)(C)C1CC2=CC3=C(OC(=O)C(=C3)C(C)(C)C=C)C=C2O1
InChI Identifier
InChI=1S/C21H24O5/c1-7-20(3,4)15-9-13-8-14-10-18(21(5,6)26-12(2)22)24-16(14)11-17(13)25-19(15)23/h7-9,11,18H,1,10H2,2-6H3
InChI KeyAWMHMGFGCLBSAY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentPsoralens
Alternative Parents
Substituents
  • Psoralen
  • Benzopyran
  • 1-benzopyran
  • Coumaran
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Lactone
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point107 - 108 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.24 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0042 g/LALOGPS
logP4.73ALOGPS
logP3.74ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area61.83 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity98.12 m³·mol⁻¹ChemAxon
Polarizability39.12 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]+183.10131661259
DarkChem[M-H]-183.54731661259
DeepCCS[M+H]+184.04530932474
DeepCCS[M-H]-181.68730932474
DeepCCS[M-2H]-215.64330932474
DeepCCS[M+Na]+190.87130932474
AllCCS[M+H]+185.932859911
AllCCS[M+H-H2O]+182.932859911
AllCCS[M+NH4]+188.632859911
AllCCS[M+Na]+189.432859911
AllCCS[M-H]-192.332859911
AllCCS[M+Na-2H]-192.432859911
AllCCS[M+HCOO]-192.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Chalepin acetateCC(=O)OC(C)(C)C1CC2=CC3=C(OC(=O)C(=C3)C(C)(C)C=C)C=C2O13244.0Standard polar33892256
Chalepin acetateCC(=O)OC(C)(C)C1CC2=CC3=C(OC(=O)C(=C3)C(C)(C)C=C)C=C2O12526.4Standard non polar33892256
Chalepin acetateCC(=O)OC(C)(C)C1CC2=CC3=C(OC(=O)C(=C3)C(C)(C)C=C)C=C2O12617.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chalepin acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-8094000000-728ba4b61073c46448c72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chalepin acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chalepin acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalepin acetate , positive-QTOFsplash10-0a4m-0491000000-44662a0b30502e4bdad62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalepin acetate 40V, Negative-QTOFsplash10-05ot-6894000000-815fbb7191e68caef2242021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalepin acetate 10V, Negative-QTOFsplash10-06r2-5895000000-be5bffc8f3b2d7325bc62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalepin acetate 20V, Positive-QTOFsplash10-0a4i-0093000000-b61aeaebc51216ddc88f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalepin acetate 10V, Positive-QTOFsplash10-0a4i-0019000000-9f0f6e3ac712c791babc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalepin acetate 40V, Positive-QTOFsplash10-0707-0490000000-c6da86bdb1165b6c432b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chalepin acetate 20V, Negative-QTOFsplash10-0bta-5894000000-193d0355e577071049692021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalepin acetate 10V, Positive-QTOFsplash10-0aos-3089000000-cdb6d4ac3e148551d4ed2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalepin acetate 20V, Positive-QTOFsplash10-014j-8093000000-75c90650ced00d4c6b2d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalepin acetate 40V, Positive-QTOFsplash10-014l-9270000000-6a5c2789f584fc59dccf2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalepin acetate 10V, Negative-QTOFsplash10-0a4i-4029000000-b39c6150d86cfaad15ab2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalepin acetate 20V, Negative-QTOFsplash10-0a4i-9075000000-97d74242bc9a4a65f0dd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalepin acetate 40V, Negative-QTOFsplash10-0a4i-9020000000-e724b2f3d11c6e4d54d72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalepin acetate 10V, Negative-QTOFsplash10-0a4i-9030000000-8cee70b1bdde2cb4c4522021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalepin acetate 20V, Negative-QTOFsplash10-0a4i-9020000000-a39ccb8c51c14bd716222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalepin acetate 40V, Negative-QTOFsplash10-056u-6091000000-7bb7056a6eb5943403f22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalepin acetate 10V, Positive-QTOFsplash10-0a4j-0069000000-6bb341aab5505dcd8f4b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalepin acetate 20V, Positive-QTOFsplash10-0100-0090000000-fb38e83da2e1923b65d02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chalepin acetate 40V, Positive-QTOFsplash10-00pi-2091000000-24cd0444f8fc2682c8422021-09-22Wishart 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 IDFDB002578
KNApSAcK IDC00002495
Chemspider ID25094
KEGG Compound IDC09308
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound26948
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1821891
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:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
Chalepin acetate → 2-(2-hydroxypropan-2-yl)-6-(2-methylbut-3-en-2-yl)-2H,3H,7H-furo[3,2-g]chromen-7-onedetails