Momilactone B (CHEM030409)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:52:30 UTC
Update Date2016-11-09 01:19:04 UTC
Accession NumberCHEM030409
Identification
Common NameMomilactone B
ClassSmall Molecule
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.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3b,20-Epoxy-3a-hydroxy-7,15-pimaradien-19,6b-olideHMDB
Momilacton bHMDB
Momilactone bMeSH
Chemical FormulaC20H26O4
Average Molecular Mass330.418 g/mol
Monoisotopic Mass330.183 g/mol
CAS Registry Number51415-08-8
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
Traditional Name5-ethenyl-13-hydroxy-5,12-dimethyl-10,14-dioxapentacyclo[11.2.2.1¹,⁹.0²,⁷.0¹²,¹⁸]octadec-7-en-11-one
SMILESCC12C3C(OC1=O)C=C1CC(C)(CCC1C31CCC2(O)OC1)C=C
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014r-7594000000-262e9a486816a49966edSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000i-9204000000-01083810d31bad04f17aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0029000000-efd9dd6471fec372d203Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-5259000000-4d21f007a0c800a54780Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9441000000-d1bb689b6f85a17a1415Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-71a231edd4c086920a1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0019000000-dcaf394ed89d9e3d9fbaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00li-0590000000-28abb07c252c401a32acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-00a7d712e9bc4f24f659Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0095000000-c0ceddbd2548e575cfc3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001a-2960000000-51d1f38d076c94076b61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-f547833d1942b8c5fe90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0009000000-f547833d1942b8c5fe90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-1059000000-487b3e63f89e0fc52e7aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0036749
FooDB IDFDB015687
Phenol Explorer IDNot Available
KNApSAcK IDC00000260
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMomilactone B
Chemspider ID24785551
ChEBI IDNot Available
PubChem Compound ID73018629
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.