1.0 2010-04-08 22:04:59 UTC 2025-11-18 22:31:43 UTC FDB001505 Lycopsamine Lycopsamine, also known as indicine or 9-viridiflorylretronecine, belongs to alkaloids and derivatives class of compounds. Those are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic propertiesand is also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Lycopsamine is soluble (in water) and a very weakly acidic compound (based on its pKa). Lycopsamine can be found in borage, which makes lycopsamine a potential biomarker for the consumption of this food product. 9-Viridiflorylretronecine C15H25NO5 299.3627 299.173272915 [(1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate lycopsamine 10285-07-1 [H][C@@](C)(O)[C@@](O)(C(C)C)C(=O)OCC1=CCN2CC[C@@]([H])(O)[C@@]12[H] InChI=1S/C15H25NO5/c1-9(2)15(20,10(3)17)14(19)21-8-11-4-6-16-7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3/t10-,12+,13+,15-/m0/s1 SFVVQRJOGUKCEG-ZGFBFQLVSA-N belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Alkaloids and derivatives Organic compounds Alkaloids and derivatives Aliphatic heteropolycyclic compounds Amino acids and derivatives Azacyclic compounds Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acid esters Fatty acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives N-alkylpyrrolidines Organic oxides Organopnictogen compounds Pyrrolines Pyrrolizines Secondary alcohols Tertiary alcohols Trialkylamines Alcohol Aliphatic heteropolycyclic compound Alkaloid or derivatives Amine Amino acid or derivatives Azacycle Beta-hydroxy acid Carbonyl group Carboxylic acid derivative Carboxylic acid ester Fatty acid ester Fatty acyl 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 Pyrrolidine Pyrroline Pyrrolizine Secondary alcohol Tertiary alcohol Tertiary aliphatic amine Tertiary amine Pyrrolizidine alkaloids pyrrolizines logp 0.41 ALOGPS logs -0.77 ALOGPS solubility 5.08e+01 g/l ALOGPS logp -0.29 ChemAxon pka_strongest_acidic 11.34 ChemAxon pka_strongest_basic 7.82 ChemAxon iupac [(1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate ChemAxon average_mass 299.3627 ChemAxon mono_mass 299.173272915 ChemAxon smiles [H][C@@](C)(O)[C@@](O)(C(C)C)C(=O)OCC1=CCN2CC[C@@]([H])(O)[C@@]12[H] ChemAxon formula C15H25NO5 ChemAxon inchi InChI=1S/C15H25NO5/c1-9(2)15(20,10(3)17)14(19)21-8-11-4-6-16-7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3/t10-,12+,13+,15-/m0/s1 ChemAxon inchikey SFVVQRJOGUKCEG-ZGFBFQLVSA-N ChemAxon polar_surface_area 90.23 ChemAxon refractivity 77.94 ChemAxon polarizability 31.75 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 94701 Specdb::MsMs 94702 Specdb::MsMs 94703 Specdb::MsMs 158784 Specdb::MsMs 158785 Specdb::MsMs 158786 Specdb::MsMs 3597616 Specdb::MsMs 3597617 Specdb::MsMs 3597618 Specdb::MsMs 3597619 Specdb::MsMs 3597620 Specdb::MsMs 3597621 Borage Type 1 specific Borago officinalis 13363 Hepatotoxic 984 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.