1.0 2010-04-08 22:11:51 UTC 2019-11-26 03:11:37 UTC FDB015466 Aucubin Aucubin is a monoterpenoid based compound. Aucubin, like all iridoids, has a cyclopentan-[C]-pyran skeleton. Iridoids can consist of ten, nine, or rarely eight carbons in which C11 is more frequently missing than C10. Aucubin has 10 carbons with the C11 carbon missing. The stereochemical configurations at C5 and C9 lead to cis fused rings, which are common to all iridoids containing carbocylclic- or seco-skeleton in non-rearranged form. Oxidative cleavage at C7-C8 bond affords secoiridoids. The last steps in the biosynthesis of iridoids usually consist of O-glycosylation and O-alkylation. Aucubin, a glycoside iridoid, has an O-linked glucose moiety.; Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Irioids decrease the growth rates of many generalist herbivores. Aucubin is found in the leaves of Aucuba japonica (Cornaceae), Eucommia ulmoides (Eucommiaceae), and Plantago asiatic (Plantaginaceae), etc, plants used in traditional Chinese and folk medicine. Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally.; Geranyl pyrophosphate is the precursor for iridoids. Geranyl phosphate is generated through the mevalonate pathway or the methylerythritol phosphate pathway. The initial steps of the pathway involve the fusion of three molecules of acetyl-CoA to produce the C6 compound 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA). HMG-CoA is then reduced in two steps by the enzyme HMG-CoA reductase. The resulting mevalonate is then sequentially phosphorylated by two separate kinases, mevalonate kinase and phosphomevalonate kinase, to form 5-pyrophosphomevalonate. Phosphosphomevalonate decarboxylase through a concerted decarboxylation reaction affords isopentenyl pyrophosphate (IPP). IPP is the basic C5 building block that is added to prenyl phosphate cosubstrates to form longer chains. IPP is isomerized to the allylic ester dimethylallyl pyrophosphate (DMAPP) by IPP isomerase. Through a multistep process, including the dephosphorylation DMAPP, IPP and DMAPP are combinded to from the C10 compound geranyl pyrophosphate (GPP). Geranyl pyrophosphate is a major branch point for terpenoid synthesis.; The cyclizaton reaction to form the iridoid pyrane ring may result from one of two routes: route 1 - a hydride nucleophillic attack on C1 will lead to 1-O-carbonyl atom attack on C3, yielding the lactone ring; route 2 - loss of proton from carbon 4 leads to the formation of a double bond C3-C4; consequently the 3-0-carbonyl atom will attach to C1. Aucubin Aucuboside Rhimantin Rhinanthin C15H22O9 346.3298 346.126382302 2-{[5-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol aucubin 479-98-1 OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C(O)C1O InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2 RJWJHRPNHPHBRN-UHFFFAOYSA-N belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. Iridoid O-glycosides Organic compounds Lipids and lipid-like molecules Prenol lipids Terpene glycosides Aliphatic heteropolycyclic compounds Acetals Bicyclic monoterpenoids Hexoses Hydrocarbon derivatives Iridoids and derivatives O-glycosyl compounds Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Acetal Alcohol Aliphatic heteropolycyclic compound Bicyclic monoterpenoid Glycosyl compound Hexose monosaccharide Hydrocarbon derivative Iridoid o-glycoside Iridoid-skeleton Monosaccharide Monoterpenoid O-glycosyl compound Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol logp -2.14 ALOGPS logs -0.84 ALOGPS solubility 5.00e+01 g/l ALOGPS melting_point Mp 181° logp -3.2 ChemAxon pka_strongest_acidic 12.2 ChemAxon pka_strongest_basic -2.7 ChemAxon iupac 2-{[5-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol ChemAxon average_mass 346.3298 ChemAxon mono_mass 346.126382302 ChemAxon smiles OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C(O)C1O ChemAxon formula C15H22O9 ChemAxon inchi InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2 ChemAxon inchikey RJWJHRPNHPHBRN-UHFFFAOYSA-N ChemAxon polar_surface_area 149.07 ChemAxon refractivity 79.18 ChemAxon polarizability 33.65 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 9 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 14972 Specdb::CMs 44905 Specdb::CMs 158883 Specdb::MsMs 7538 Specdb::MsMs 7539 Specdb::MsMs 7540 Specdb::MsMs 14210 Specdb::MsMs 14211 Specdb::MsMs 14212 Specdb::MsMs 2831824 Specdb::MsMs 2831825 Specdb::MsMs 2831826 Specdb::MsMs 2849770 Specdb::MsMs 2849771 Specdb::MsMs 2849772 Specdb::NmrOneD 136470 Specdb::NmrOneD 136471 Specdb::NmrOneD 136472 Specdb::NmrOneD 136473 Specdb::NmrOneD 136474 Specdb::NmrOneD 136475 Specdb::NmrOneD 136476 Specdb::NmrOneD 136477 Specdb::NmrOneD 136478 Specdb::NmrOneD 136479 Specdb::NmrOneD 136480 Specdb::NmrOneD 136481 Specdb::NmrOneD 136482 Specdb::NmrOneD 136483 Specdb::NmrOneD 136484 Specdb::NmrOneD 136485 Specdb::NmrOneD 136486 Specdb::NmrOneD 136487 Specdb::NmrOneD 136488 Specdb::NmrOneD 136489 HMDB36562 #<Reference:0x000055ce323d5eb8> #<Reference:0x000055ce323d5d00> Common verbena Type 1 specific Verbena officinalis 79772 Anti bacterial 145 A substance that kills or slows the growth of bacteria. Anti leukemic 393 A substance that inhibits or prevents the proliferation of neoplasms. Anti prolactin 546 Anti-edemic 248 Anti-inflammatory 370 A substance that reduces or suppresses inflammation. Anti-oxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. Anti-staphylococcic 627 A substance that kills or slows the growth of bacteria. Antidote 236 Any protective agent counteracting or neutralizing the action of poisons. Candidicide 756 Cathartic 784 Any substance that accelerates defecation. Compare with laxatives, which are substances that ease defecation (usually by softening faeces). A substance can be both a laxative and a cathartic. Collagenic 824 Diuretic 883 An agent that promotes the excretion of urine through its effects on kidney function. Hepatoprotective 981 Any compound that is able to prevent damage to the liver. Lactagogue 1062 Laxative 1065 An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic. Paralytic 1196 Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. RNA inhibitor 1298 A substance that diminishes the rate of a chemical reaction. Uricosuric 1396