1.0 2010-04-08 22:07:00 UTC 2025-11-18 23:00:57 UTC FDB006127 Rotundifoline Rotundifoline is a member of the class of compounds known as indolizidines. Indolizidines are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen. Rotundifoline is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Rotundifoline can be found in mentha (mint) and spearmint, which makes rotundifoline a potential biomarker for the consumption of these food products. Mitrafoline C22H28N2O5 400.4681 400.199822016 methyl (2E)-2-[(6'R,7'S)-6'-ethyl-4-hydroxy-2-oxo-1,2,3',5',6',7',8',8'a-octahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate methyl (2E)-2-[(6'R,7'S)-6'-ethyl-4-hydroxy-2-oxo-3',5',6',7',8',8'a-hexahydro-1H,2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate CC[C@H]1CN2CCC3(C2C[C@@H]1\C(=C/OC)C(=O)OC)C(=O)NC1=C3C(O)=CC=C1 InChI=1S/C22H28N2O5/c1-4-13-11-24-9-8-22(19-16(23-21(22)27)6-5-7-17(19)25)18(24)10-14(13)15(12-28-2)20(26)29-3/h5-7,12-14,18,25H,4,8-11H2,1-3H3,(H,23,27)/b15-12+/t13-,14-,18?,22?/m0/s1 IXWWTVSMMIIIFZ-LWWKTLCYSA-N belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen. Indolizidines Organic compounds Organoheterocyclic compounds Indolizidines Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Amino acids and derivatives Aralkylamines Azacyclic compounds Carbonyl compounds Enoate esters Hydrocarbon derivatives Indolines Lactams Methyl esters Monocarboxylic acids and derivatives N-alkylpyrrolidines Organic oxides Organopnictogen compounds Piperidines Secondary carboxylic acid amides Trialkylamines Vinylogous esters 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alpha,beta-unsaturated carboxylic ester Amine Amino acid or derivatives Aralkylamine Aromatic heteropolycyclic compound Azacycle Benzenoid Carbonyl group Carboxamide group Carboxylic acid derivative Carboxylic acid ester Dihydroindole Enoate ester Hydrocarbon derivative Indole or derivatives Indolizidine Lactam Methyl ester Monocarboxylic acid or derivatives N-alkylpyrrolidine Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Piperidine Pyrrolidine Secondary carboxylic acid amide Tertiary aliphatic amine Tertiary amine Vinylogous ester logp 2.64 ALOGPS logs -2.98 ALOGPS solubility 4.23e-01 g/l ALOGPS logp 1.04 ChemAxon pka_strongest_acidic 8.84 ChemAxon pka_strongest_basic 10.25 ChemAxon iupac methyl (2E)-2-[(6'R,7'S)-6'-ethyl-4-hydroxy-2-oxo-1,2,3',5',6',7',8',8'a-octahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate ChemAxon average_mass 400.4681 ChemAxon mono_mass 400.199822016 ChemAxon smiles CC[C@H]1CN2CCC3(C2C[C@@H]1\C(=C/OC)C(=O)OC)C(=O)NC1=C3C(O)=CC=C1 ChemAxon formula C22H28N2O5 ChemAxon inchi InChI=1S/C22H28N2O5/c1-4-13-11-24-9-8-22(19-16(23-21(22)27)6-5-7-17(19)25)18(24)10-14(13)15(12-28-2)20(26)29-3/h5-7,12-14,18,25H,4,8-11H2,1-3H3,(H,23,27)/b15-12+/t13-,14-,18?,22?/m0/s1 ChemAxon inchikey IXWWTVSMMIIIFZ-LWWKTLCYSA-N ChemAxon polar_surface_area 88.1 ChemAxon refractivity 109.99 ChemAxon polarizability 42.39 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 51231 Specdb::MsMs 51232 Specdb::MsMs 51233 Specdb::MsMs 145890 Specdb::MsMs 145891 Specdb::MsMs 145892 Specdb::MsMs 3602525 Specdb::MsMs 3602526 Specdb::MsMs 3602527 Specdb::MsMs 3602528 Specdb::MsMs 3602529 Specdb::MsMs 3602530 Mentha Type 1 specific Mentha 21819 Spearmint Type 1 specific Mentha spicata 29719 796.75 796.75 796.75 mg/100 g