1.0 2011-09-21 00:36:34 UTC 2015-07-21 06:57:55 UTC FDB023899 Pseudoecgonine Pseudoecgonine is a metabolic byproduct of cocaine. Cocaine is extensively metabolized in the liver, with only about 1% excreted unchanged in the urine. The metabolism is dominated by hydrolytic ester cleavage, so the eliminated metabolites consist mostly of benzoylecgonine, the major metabolite, and in lesser amounts ecgonine methyl ester and ecgonine. Pseudoecgonine is a steroisomer of ecgonine and may be conjugated to CoA to form Pseudoecgonyl-CoA through the action of gut microlfora (PMID: 8572717). [HMDB] (+)-Pseudoecgonine (2S,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate (2S,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid d-Pseudoecgonine d-psi-Ecgonine delta-Pseudoecgonine delta-psi-Ecgonine Pseudo-ecgonine Pseudoecgonine C9H15NO3 185.2203 185.105193351 (2S,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid pseudoecgonine CN1C2CCC1[C@@H]([C@@H](O)C2)C(O)=O InChI=1S/C9H15NO3/c1-10-5-2-3-6(10)8(9(12)13)7(11)4-5/h5-8,11H,2-4H2,1H3,(H,12,13)/t5?,6?,7-,8-/m0/s1 PHMBVCPLDPDESM-GHNGIAPOSA-N belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane. Tropane alkaloids Organic compounds Alkaloids and derivatives Tropane alkaloids Aliphatic heteropolycyclic compounds Amino acids Azacyclic compounds Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives N-alkylpyrrolidines Organic oxides Organopnictogen compounds Piperidinecarboxylic acids Secondary alcohols Trialkylamines Alcohol Aliphatic heteropolycyclic compound Amine Amino acid Amino acid or derivatives Azacycle Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Hydrocarbon derivative Hydroxy acid Monocarboxylic acid or derivatives N-alkylpyrrolidine Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Piperidine Piperidinecarboxylic acid Pyrrolidine Secondary alcohol Tertiary aliphatic amine Tertiary amine Tropane alkaloid Tropane alkaloids tropane alkaloid Solid logp -0.69 ALOGPS logs 0.75 ALOGPS solubility 1.05e+03 g/l ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 3.48 ChemAxon pka_strongest_basic 9.69 ChemAxon iupac (2S,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid ChemAxon average_mass 185.2203 ChemAxon mono_mass 185.105193351 ChemAxon smiles CN1C2CCC1[C@@H]([C@@H](O)C2)C(O)=O ChemAxon formula C9H15NO3 ChemAxon inchi InChI=1S/C9H15NO3/c1-10-5-2-3-6(10)8(9(12)13)7(11)4-5/h5-8,11H,2-4H2,1H3,(H,12,13)/t5?,6?,7-,8-/m0/s1 ChemAxon inchikey PHMBVCPLDPDESM-GHNGIAPOSA-N ChemAxon polar_surface_area 60.77 ChemAxon refractivity 46.57 ChemAxon polarizability 18.96 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 22203 Specdb::CMs 39006 Specdb::CMs 163438 Specdb::MsMs 315286 Specdb::MsMs 315287 Specdb::MsMs 315288 Specdb::MsMs 361225 Specdb::MsMs 361226 Specdb::MsMs 361227 Specdb::MsMs 2288388 Specdb::MsMs 2288389 Specdb::MsMs 2288390 Specdb::MsMs 2647437 Specdb::MsMs 2647438 Specdb::MsMs 2647439 Specdb::NmrOneD 68212 Specdb::NmrOneD 68213 Specdb::NmrOneD 68214 Specdb::NmrOneD 68215 Specdb::NmrOneD 68216 Specdb::NmrOneD 68217 Specdb::NmrOneD 68218 Specdb::NmrOneD 68219 Specdb::NmrOneD 68220 Specdb::NmrOneD 68221 Specdb::NmrOneD 68222 Specdb::NmrOneD 68223 Specdb::NmrOneD 68224 Specdb::NmrOneD 68225 Specdb::NmrOneD 68226 Specdb::NmrOneD 68227 Specdb::NmrOneD 68228 Specdb::NmrOneD 68229 Specdb::NmrOneD 68230 Specdb::NmrOneD 68231 HMDB06348 #<Reference:0x000055ce32ab16b0>