2-[[5-Hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
PubChem CID: 348157
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| Compound Synonyms | rhinanthin, NSC407293, Rhimantin, 2-[[5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol, 5-Hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl hexopyranoside, (2S,3R,4S,5S,6R)-2-[[(1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol, HMS3345J02, STL445434, AKOS037626766, LS-14438, DB-051492, NS00043461, .Beta.-D-Glucopyranoside, 1,4a,5, 7a-tetrahydro-5-hydroxy-7- {(hydroxymethyl)cyclopenta[c]pyran-1-yl,} {[1S-(1.alpha.,4a.alpha.,5.alpha.,7a.alpha)]-}, 2-[[5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol |
|---|---|
| Topological Polar Surface Area | 149.0 |
| Hydrogen Bond Donor Count | 6.0 |
| Inchi Key | RJWJHRPNHPHBRN-UHFFFAOYSA-N |
| Rotatable Bond Count | 4.0 |
| State | Solid |
| Synonyms | Aucubin, Aucuboside, Rhimantin, Rhinanthin |
| Heavy Atom Count | 24.0 |
| Compound Name | 2-[[5-Hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol |
| Kingdom | Organic compounds |
| Description | 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. |
| Exact Mass | 346.126 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 346.126 |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 507.0 |
| Hydrogen Bond Acceptor Count | 9.0 |
| Molecular Weight | 346.33 |
| Database Name | fooddb_chem_all;hmdb_chem_all;pubchem |
| Covalent Unit Count | 1.0 |
| Defined Atom Stereocenter Count | 0.0 |
| Iupac Name | 2-[[5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol |
| Total Atom Stereocenter Count | 9.0 |
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Total Bond Stereocenter Count | 0.0 |
| Class | Prenol lipids |
| 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 |
| Smiles | C1=COC(C2C1C(C=C2CO)O)OC3C(C(C(C(O3)CO)O)O)O |
| Xlogp | -3.0 |
| Superclass | Lipids and lipid-like molecules |
| Defined Bond Stereocenter Count | 0.0 |
| Subclass | Terpene glycosides |
| Taxonomy Direct Parent | Iridoid O-glycosides |
| Molecular Formula | C15H22O9 |
- 1. Outgoing r'ship
FOUND_INto/from Verbena Officinalis (Plant) Rel Props:Source_db:fooddb_chem_all