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Showing Compound Momilactone B (FDB015687)

Record Information
Version1.0
Creation date2010-04-08 22:11:59 UTC
Update date2019-11-26 03:12:02 UTC
Primary IDFDB015687
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMomilactone B
DescriptionConstituent of Oryza sativa (rice) Momilactone B is an allelopathic agent produced from the roots of rice (Oryza sativa L.) (100 mg from 200 kg dry rice husk). It has been shown to be produced in high concentrations by the roots of rice seedlings. The production of momilactone B has also been induced in response to infection by blast fungus (Pyricularia oryzae) or irradiated with UV light. More recently is has been shown to be a potential chemotherapeutic agent against human colon cancer.; The second step is the cyclization of syn-CDP to 9?-pimara-7,15-diene. This step is initiated by the elimination of the diphosphate group, a type A cyclization. The genes encoding for the type A cyclase were found by Otomo et al. in 2004. It is suggested that OsKS4, located on chromosome 4 (14.3cM) is one of the genes responsible for phytoalexin biosynthesis. After UV-radiation, OsKS4 mRNA levels rise drastically in response to the attack. Momilactone B is found in cereals and cereal products and rice.
CAS Number51415-08-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.045 g/LALOGPS
logP2.6ALOGPS
logP2.81ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)11.42ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity89.64 m³·mol⁻¹ChemAxon
Polarizability35.79 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H26O4
IUPAC name5-ethenyl-13-hydroxy-5,12-dimethyl-10,14-dioxapentacyclo[11.2.2.1¹,⁹.0²,⁷.0¹²,¹⁸]octadec-7-en-11-one
InChI IdentifierInChI=1S/C20H26O4/c1-4-17(2)6-5-13-12(10-17)9-14-15-18(3,16(21)24-14)20(22)8-7-19(13,15)11-23-20/h4,9,13-15,22H,1,5-8,10-11H2,2-3H3
InChI KeySONPFFIKLYCKOY-UHFFFAOYSA-N
Isomeric SMILESCC12C3C(OC1=O)C=C1CC(C)(CCC1C31CCC2(O)OC1)C=C
Average Molecular Weight330.418
Monoisotopic Molecular Weight330.18310932
Classification
Description Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNot Available
Direct ParentNaphthopyrans
Alternative Parents
Substituents
  • Naphthopyran
  • Naphthofuran
  • Naphthalene
  • Furopyran
  • Gamma butyrolactone
  • Oxane
  • Pyran
  • Furan
  • Cyclic alcohol
  • Tetrahydrofuran
  • Lactone
  • Hemiacetal
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSMomilactone B, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014r-7594000000-262e9a486816a49966edSpectrum
Predicted GC-MSMomilactone B, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-9204000000-01083810d31bad04f17aSpectrum
Predicted GC-MSMomilactone B, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0029000000-efd9dd6471fec372d2032016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-5259000000-4d21f007a0c800a547802016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9441000000-d1bb689b6f85a17a14152016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-71a231edd4c086920a1c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0019000000-dcaf394ed89d9e3d9fba2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00li-0590000000-28abb07c252c401a32ac2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-00a7d712e9bc4f24f6592021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0095000000-c0ceddbd2548e575cfc32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001a-2960000000-51d1f38d076c94076b612021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-f547833d1942b8c5fe902021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0009000000-f547833d1942b8c5fe902021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-1059000000-487b3e63f89e0fc52e7a2021-09-22View Spectrum
NMRNot Available
ChemSpider ID24785551
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID3084979
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36749
CRC / DFC (Dictionary of Food Compounds) IDKGF14-Z:KGF14-Z
EAFUS IDNot Available
Dr. Duke IDMOMILACTONE-B
BIGG IDNot Available
KNApSAcK IDC00000260
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMomilactone_B
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Breakfast cerealExpected but not quantifiedNot AvailableDFC CODES
Rice0.10000 - 0.10000 mg/100 g0.10000 mg/100 gDUKE, KNAPSACK
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Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.