1.0 2010-04-08 22:11:12 UTC 2019-11-26 03:09:49 UTC FDB014309 Monotropein Constituent of Liquidambar styraciflua (sweet gum) and Liquidambar orientalis (oriental sweet gum). Food flavouring agent. Stabiliser. Monotropein is found in bilberry. Monotropein (8CI) Monotropeine C16H22O11 390.3393 390.116211546 7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid 7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7aH-cyclopenta[c]pyran-4-carboxylic acid 5945-50-6 OCC1OC(OC2OC=C(C3C=CC(O)(CO)C23)C(O)=O)C(O)C(O)C1O InChI=1S/C16H22O11/c17-3-8-10(19)11(20)12(21)15(26-8)27-14-9-6(1-2-16(9,24)5-18)7(4-25-14)13(22)23/h1-2,4,6,8-12,14-15,17-21,24H,3,5H2,(H,22,23) HPWWQPXTUDMRBI-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 Carbonyl compounds Carboxylic acids Hexoses Hydrocarbon derivatives Iridoids and derivatives Monocarboxylic acids and derivatives O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Tertiary alcohols Vinylogous esters Acetal Alcohol Aliphatic heteropolycyclic compound Bicyclic monoterpenoid Carbonyl group Carboxylic acid Carboxylic acid derivative Glycosyl compound Hexose monosaccharide Hydrocarbon derivative Iridoid o-glycoside Iridoid-skeleton Monocarboxylic acid or derivatives Monosaccharide Monoterpenoid O-glycosyl compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol Tertiary alcohol Vinylogous ester logp -1.91 ALOGPS logs -0.89 ALOGPS solubility 5.02e+01 g/l ALOGPS melting_point Mp 175° dec. logp -3.3 ChemAxon pka_strongest_acidic 4.14 ChemAxon pka_strongest_basic -3 ChemAxon iupac 7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid ChemAxon average_mass 390.3393 ChemAxon mono_mass 390.116211546 ChemAxon smiles OCC1OC(OC2OC=C(C3C=CC(O)(CO)C23)C(O)=O)C(O)C(O)C1O ChemAxon formula C16H22O11 ChemAxon inchi InChI=1S/C16H22O11/c17-3-8-10(19)11(20)12(21)15(26-8)27-14-9-6(1-2-16(9,24)5-18)7(4-25-14)13(22)23/h1-2,4,6,8-12,14-15,17-21,24H,3,5H2,(H,22,23) ChemAxon inchikey HPWWQPXTUDMRBI-UHFFFAOYSA-N ChemAxon polar_surface_area 186.37 ChemAxon refractivity 85.02 ChemAxon polarizability 36.41 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 11 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 14295 Specdb::CMs 44446 Specdb::CMs 151723 Specdb::CMs 156321 Specdb::CMs 279859 Specdb::NmrOneD 132118 Specdb::NmrOneD 132119 Specdb::NmrOneD 132120 Specdb::NmrOneD 132121 Specdb::NmrOneD 132122 Specdb::NmrOneD 132123 Specdb::NmrOneD 132124 Specdb::NmrOneD 132125 Specdb::NmrOneD 132126 Specdb::NmrOneD 132127 Specdb::NmrOneD 132128 Specdb::NmrOneD 132129 Specdb::NmrOneD 132130 Specdb::NmrOneD 132131 Specdb::NmrOneD 132132 Specdb::NmrOneD 132133 Specdb::NmrOneD 132134 Specdb::NmrOneD 132135 Specdb::NmrOneD 132136 Specdb::NmrOneD 132137 Specdb::MsMs 8432 Specdb::MsMs 8433 Specdb::MsMs 8434 Specdb::MsMs 13097 Specdb::MsMs 13098 Specdb::MsMs 13099 Specdb::MsMs 15104 Specdb::MsMs 15105 Specdb::MsMs 15106 Specdb::MsMs 19769 Specdb::MsMs 19770 Specdb::MsMs 19771 Specdb::MsMs 2364202 Specdb::MsMs 2364203 Specdb::MsMs 2364204 Specdb::MsMs 2602250 Specdb::MsMs 2602251 Specdb::MsMs 2602252 HMDB35608 #<Reference:0x000055ce2efd3368> #<Reference:0x000055ce2efd3070> American cranberry Type 1 specific Vaccinium macrocarpon 13750 Bilberry Type 1 specific Vaccinium myrtillus 180763 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. 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.