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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:54:16 UTC
Update Date2019-07-23 06:15:12 UTC
HMDB IDHMDB0034109
Secondary Accession Numbers
  • HMDB34109
Metabolite Identification
Common NameFrenolicin B
DescriptionFrenolicin B, also known as am 3867I or UCF76 C, belongs to the class of organic compounds known as benzoisochromanequinones. These are benzo derivatives of isochromanequinones. Isochromanequinones are structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton. Frenolicin B is an extremely weak basic (essentially neutral) compound (based on its pKa). Antibiotic feed additive especies for poultry and pigs.
Structure
Data?1563862512
Synonyms
ValueSource
AM 3867IHMDB
Antibiotic am 3867IHMDB
Antibiotic ucf76 CHMDB
UCF76 CHMDB
Chemical FormulaC18H16O6
Average Molecular Weight328.316
Monoisotopic Molecular Weight328.094688244
IUPAC Name4-hydroxy-17-propyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione
Traditional Name4-hydroxy-17-propyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione
CAS Registry Number68930-68-7
SMILES
CCCC1OC2CC(=O)OC2C2=C1C(=O)C1=C(C=CC=C1O)C2=O
InChI Identifier
InChI=1S/C18H16O6/c1-2-4-10-14-15(18-11(23-10)7-12(20)24-18)16(21)8-5-3-6-9(19)13(8)17(14)22/h3,5-6,10-11,18-19H,2,4,7H2,1H3
InChI KeyAVCPRTNVVRPELB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzoisochromanequinones. These are benzo derivatives of isochromanequinones. Isochromanequinones are structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsochromanequinones
Sub ClassBenzoisochromanequinones
Direct ParentBenzoisochromanequinones
Alternative Parents
Substituents
  • Benzoisochromanequinone
  • Naphthopyranone
  • Naphthopyran
  • Naphthoquinone
  • Naphthalene
  • Furopyran
  • Aryl ketone
  • Quinone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Gamma butyrolactone
  • Benzenoid
  • Pyran
  • Tetrahydrofuran
  • Furan
  • Vinylogous acid
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point157 - 159 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.74 g/LALOGPS
logP2.69ALOGPS
logP2.42ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)9.41ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area89.9 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity83.39 m³·mol⁻¹ChemAxon
Polarizability33.17 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kbo-3191000000-2e243a2dcbb2c4eee0f7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-2009000000-463085069ef510ea2deeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1029000000-f6a29c2a003772ea1003Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00b9-1291000000-a09b96a34550e3a95139Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9020000000-f040d477e039995a01d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-b4b0a43a7ce371601471Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a7i-1092000000-06e10db3fdd1353b60b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06s6-9050000000-eee92b24bfc37b41d431Spectrum
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 IDFDB012376
KNApSAcK IDC00018203
Chemspider ID28587202
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13337184
PDB IDNot Available
ChEBI ID48201
Food Biomarker OntologyNot Available
VMH 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.. .