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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:10 UTC
Update Date2022-03-07 02:52:38 UTC
HMDB IDHMDB0030650
Secondary Accession Numbers
  • HMDB30650
Metabolite Identification
Common Name8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one
Description8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one, also known as 6-butyryl-8,9-dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-4-propylfuro[2,3-H]coumarin or mammea b/ac cyclo F, belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. Based on a literature review very few articles have been published on 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one.
Structure
Data?1563862017
Synonyms
ValueSource
6-Butyryl-8,9-dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-4-propylfuro[2,3-H]coumarinHMDB
Mammea b/ac cyclo FHMDB
Chemical FormulaC21H26O6
Average Molecular Weight374.4275
Monoisotopic Molecular Weight374.172938564
IUPAC Name6-butanoyl-5-hydroxy-8-(2-hydroxypropan-2-yl)-4-propyl-2H,8H,9H-furo[2,3-h]chromen-2-one
Traditional Name6-butanoyl-5-hydroxy-8-(2-hydroxypropan-2-yl)-4-propyl-8H,9H-furo[2,3-h]chromen-2-one
CAS Registry Number38537-82-5
SMILES
CCCC(=O)C1=C2OC(CC2=C2OC(=O)C=C(CCC)C2=C1O)C(C)(C)O
InChI Identifier
InChI=1S/C21H26O6/c1-5-7-11-9-15(23)27-19-12-10-14(21(3,4)25)26-20(12)17(13(22)8-6-2)18(24)16(11)19/h9,14,24-25H,5-8,10H2,1-4H3
InChI KeyAHRWRZGWPYCGMI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentAngular furanocoumarins
Alternative Parents
Substituents
  • Angular furanocoumarin
  • Butyrophenone
  • Benzopyran
  • 1-benzopyran
  • Coumaran
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Tertiary alcohol
  • Ketone
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • 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 Point75 - 81 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10.61 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.039 g/LALOGPS
logP3.39ALOGPS
logP3.97ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)8.56ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity101.44 m³·mol⁻¹ChemAxon
Polarizability40.58 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]+189.07631661259
DarkChem[M-H]-190.21931661259
DeepCCS[M+H]+191.20430932474
DeepCCS[M-H]-188.59430932474
DeepCCS[M-2H]-223.13830932474
DeepCCS[M+Na]+198.36630932474
AllCCS[M+H]+188.832859911
AllCCS[M+H-H2O]+186.132859911
AllCCS[M+NH4]+191.332859911
AllCCS[M+Na]+192.032859911
AllCCS[M-H]-195.032859911
AllCCS[M+Na-2H]-195.532859911
AllCCS[M+HCOO]-196.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-oneCCCC(=O)C1=C2OC(CC2=C2OC(=O)C=C(CCC)C2=C1O)C(C)(C)O3514.5Standard polar33892256
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-oneCCCC(=O)C1=C2OC(CC2=C2OC(=O)C=C(CCC)C2=C1O)C(C)(C)O2952.8Standard non polar33892256
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-oneCCCC(=O)C1=C2OC(CC2=C2OC(=O)C=C(CCC)C2=C1O)C(C)(C)O3056.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one,1TMS,isomer #1CCCC(=O)C1=C2OC(C(C)(C)O)CC2=C2OC(=O)C=C(CCC)C2=C1O[Si](C)(C)C2866.1Semi standard non polar33892256
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one,1TMS,isomer #2CCCC(=O)C1=C2OC(C(C)(C)O[Si](C)(C)C)CC2=C2OC(=O)C=C(CCC)C2=C1O2882.5Semi standard non polar33892256
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one,2TMS,isomer #1CCCC(=O)C1=C2OC(C(C)(C)O[Si](C)(C)C)CC2=C2OC(=O)C=C(CCC)C2=C1O[Si](C)(C)C2897.3Semi standard non polar33892256
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one,1TBDMS,isomer #1CCCC(=O)C1=C2OC(C(C)(C)O)CC2=C2OC(=O)C=C(CCC)C2=C1O[Si](C)(C)C(C)(C)C3097.3Semi standard non polar33892256
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one,1TBDMS,isomer #2CCCC(=O)C1=C2OC(C(C)(C)O[Si](C)(C)C(C)(C)C)CC2=C2OC(=O)C=C(CCC)C2=C1O3115.3Semi standard non polar33892256
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one,2TBDMS,isomer #1CCCC(=O)C1=C2OC(C(C)(C)O[Si](C)(C)C(C)(C)C)CC2=C2OC(=O)C=C(CCC)C2=C1O[Si](C)(C)C(C)(C)C3349.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-8129000000-158a31cf9cb6156bf3c52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one GC-MS (2 TMS) - 70eV, Positivesplash10-0fhi-9520440000-a833c314fa7befb3aa682017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 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 - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 10V, Positive-QTOFsplash10-056r-0009000000-c5fecb41eb0bbf48c45b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 20V, Positive-QTOFsplash10-08j0-2019000000-9194746b460d77b08b272016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 40V, Positive-QTOFsplash10-0a5c-2090000000-f6ea5249f7ad49b4908e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 10V, Negative-QTOFsplash10-00di-0009000000-b4cc5aa0b35ae4c7e1cd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 20V, Negative-QTOFsplash10-0l6r-2039000000-4261801f1cb0a2abdc012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 40V, Negative-QTOFsplash10-0600-4193000000-5d9c7ce1a9eab8248bee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 10V, Negative-QTOFsplash10-00di-0009000000-4c8686ce268f4e78c86b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 20V, Negative-QTOFsplash10-00di-0019000000-d7d8208b2cd92108b5772021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 40V, Negative-QTOFsplash10-000g-7191000000-0eb2fa6e1a61b25687552021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 10V, Positive-QTOFsplash10-004i-0009000000-4c15654bc7c3dc74190a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 20V, Positive-QTOFsplash10-004i-0019000000-fa11b42da471006430c42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one 40V, Positive-QTOFsplash10-03kl-2093000000-3275356c6f610a8b7cc92021-09-25Wishart 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 IDFDB002556
KNApSAcK IDC00046116
Chemspider ID23333299
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44546135
PDB IDNot Available
ChEBI ID554198
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1821771
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
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(1-oxobutyl)-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one → 6-{[6-butanoyl-8-(2-hydroxypropan-2-yl)-2-oxo-4-propyl-2H,8H,9H-furo[2,3-h]chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails