1.0 2010-04-08 22:11:59 UTC 2019-11-26 03:12:02 UTC FDB015687 Momilactone B Constituent 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. 3b,20-Epoxy-3a-hydroxy-7,15-pimaradien-19,6b-olide Momilacton b C20H26O4 330.418 330.18310932 5-ethenyl-13-hydroxy-5,12-dimethyl-10,14-dioxapentacyclo[11.2.2.1¹,⁹.0²,⁷.0¹²,¹⁸]octadec-7-en-11-one 5-ethenyl-13-hydroxy-5,12-dimethyl-10,14-dioxapentacyclo[11.2.2.1¹,⁹.0²,⁷.0¹²,¹⁸]octadec-7-en-11-one 51415-08-8 CC12C3C(OC1=O)C=C1CC(C)(CCC1C31CCC2(O)OC1)C=C InChI=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 SONPFFIKLYCKOY-UHFFFAOYSA-N 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. Naphthopyrans Organic compounds Organoheterocyclic compounds Naphthopyrans Aliphatic heteropolycyclic compounds Carbonyl compounds Carboxylic acid esters Cyclic alcohols and derivatives Furans Furopyrans Gamma butyrolactones Hemiacetals Hydrocarbon derivatives Monocarboxylic acids and derivatives Naphthalenes Naphthofurans Organic oxides Oxacyclic compounds Oxanes Pyrans Tetrahydrofurans Aliphatic heteropolycyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cyclic alcohol Furan Furopyran Gamma butyrolactone Hemiacetal Hydrocarbon derivative Lactone Monocarboxylic acid or derivatives Naphthalene Naphthofuran Naphthopyran Organic oxide Organic oxygen compound Organooxygen compound Oxacycle Oxane Pyran Tetrahydrofuran logp 2.60 ALOGPS logs -3.86 ALOGPS solubility 4.51e-02 g/l ALOGPS melting_point Mp 242° dec. logp 2.81 ChemAxon pka_strongest_acidic 11.42 ChemAxon pka_strongest_basic -4.3 ChemAxon iupac 5-ethenyl-13-hydroxy-5,12-dimethyl-10,14-dioxapentacyclo[11.2.2.1¹,⁹.0²,⁷.0¹²,¹⁸]octadec-7-en-11-one ChemAxon average_mass 330.418 ChemAxon mono_mass 330.18310932 ChemAxon smiles CC12C3C(OC1=O)C=C1CC(C)(CCC1C31CCC2(O)OC1)C=C ChemAxon formula C20H26O4 ChemAxon inchi InChI=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 ChemAxon inchikey SONPFFIKLYCKOY-UHFFFAOYSA-N ChemAxon polar_surface_area 55.76 ChemAxon refractivity 89.64 ChemAxon polarizability 35.79 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 24978 Specdb::CMs 45013 Specdb::CMs 161081 Specdb::MsMs 57207 Specdb::MsMs 57208 Specdb::MsMs 57209 Specdb::MsMs 112815 Specdb::MsMs 112816 Specdb::MsMs 112817 Specdb::MsMs 2417332 Specdb::MsMs 2417333 Specdb::MsMs 2417334 Specdb::MsMs 2549251 Specdb::MsMs 2549252 Specdb::MsMs 2549253 HMDB36749 #<Reference:0x000055ce3024e498> Breakfast cereal Type 2 specific Cereals and cereal products Unknown generic Rice Type 1 specific Oryza sativa 4530 0.1 0.1 0.1 mg/100 g