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(R)-N-methylcoclaurine

AlkaPlorer ID: AK019871

Synonym: '(R)-N-Methylcoclaurine', '(S)-N-methylcoclaurine', 'N-Methylcoclaurine', '(R)-1,2,3,4-Tetrahydro-1-(4-hydroxyphenyl)methyl-6-methoxy-2-methyl-7-isoquinolinol', '(S)-1,2,3,4-Tetrahydro-1-(4-hydroxyphenyl)methyl-6-methoxy-2-methyl-7-isoquinolinol', '(-)-N-Methylcoclaurine', '(+)-N-Methylcoclaurine', '(S)-1,2,3,4-tetrahydro-1-(4-hydroxyphenyl)methyl-6-methoxy-2-methyl-7-isoquinolinol', '(R)-1,2,3,4-tetrahydro-1-(4-hydroxyphenyl)methyl-6-methoxy-2-methyl-7-isoquinolinol', '(R)-N-methylcoclaurine', '(+)-(S)-N-Methylcoclaurine', '(S)-N-Methylcoclaurine'

IUPAC Name: (1S)-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-2-ium-7-ol

Structure

SMILES: COC1=C(O)C=C2C(=C1)CC[NH+](C)[C@H]2CC1=CC=C(O)C=C1

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InChI: InChI=1S/C18H21NO3/c1-19-8-7-13-10-18(22-2)17(21)11-15(13)16(19)9-12-3-5-14(20)6-4-12/h3-6,10-11,16,20-21H,7-9H2,1-2H3/p+1/t16-/m0/s1

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InChIKey: BOKVLBSSPUTWLV-INIZCTEOSA-O

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Cercidiphyllum japonicum Cercidiphyllum Cercidiphyllaceae Saxifragales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Nelumbo nucifera Nelumbo Nelumbonaceae Proteales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Diplocarpon mali Diplocarpon Drepanopezizaceae Helotiales Leotiomycetes Ascomycota Fungi Eukaryota
Rhizopogon roseolus Rhizopogon Rhizopogonaceae Boletales Agaricomycetes Basidiomycota Fungi Eukaryota
Solanum lasiocarpum Solanum Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Erythrina mildbraedii Erythrina Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Mus musculus Mus Muridae Rodentia Mammalia Chordata Metazoa Eukaryota
Caulerpa taxifolia Caulerpa Caulerpaceae Bryopsidales Ulvophyceae Chlorophyta Viridiplantae Eukaryota
None Nectandra Lauraceae Laurales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Magnolia obovata Magnolia Magnoliaceae Magnoliales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Meiothermus ruber Meiothermus Thermaceae Thermales Deinococci Deinococcota None Bacteria
Phoenix dactylifera Phoenix Arecaceae Arecales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Sophora tetraptera Sophora Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Magnolia officinalis Magnolia Magnoliaceae Magnoliales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aglaia odorata Aglaia Meliaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 300.378

TPSA？: 54.13

MolLogP？: 1.4609999999999996

Number of H-Donors: 3

Number of H-Acceptors: 3

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Plasmodium falciparum Plasmodium falciparum IC50 2.73 ug.mL-1 10.1021/np960195h
Plasmodium falciparum Plasmodium falciparum IC50 3.81 ug.mL-1 10.1021/np960195h

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT011649 COc1cc2c(cc1O)[C@@H](Cc1ccc(O)cc1)N(C)CC2.COc1cc2c(cc1O)[C@H](Cc1ccc(O)cc1)N(C)CC2>>COc1cc2c(cc1O)[C@H](Cc1ccc(Oc3cc(C[C@@H]4c5cc(O)c(OC)cc5CCN4C)ccc3O)cc1)N(C)CC2 R04694
AKRT011676 COc1cc2c(cc1O)[C@H](Cc1ccc(O)cc1)N(C)CC2>>COc1cc2c(cc1O)[C@H](Cc1ccc(O)c(O)c1)N(C)CC2 1.14.13.71-RXN
AKRT011677 COc1cc2c(cc1O)[C@H](Cc1ccc(O)cc1)NCC2.C[33S]>>COc1cc2c(cc1O)[C@H](Cc1ccc(O)cc1)N(C)CC2 None
AKRT011678 COc1cc2c(cc1O)[C@H](Cc1ccc(O)cc1)NCC2.C[SAH]>>COc1cc2c(cc1O)[C@H](Cc1ccc(O)cc1)N(C)CC2 2.1.1.140-RXN