Molecule

(S)-coclaurine

AlkaPlorer ID: AK018226

Synonym: '', '(S)-1,2,3,4-Tetrahydro-1-(4-hydroxyphenyl)methyl-6-methoxy-7-isoquinolinol', 'SMR000156307', 'Sanjoinine K', 'Machiline', 'dl-Coclaurine', '1-(p-Hydroxybenzyl)-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline', 'MLS000574945', '(+)-Coclaurine', '(R)-Coclaurine', '(S)-Coclaurine', '(+)-R-Coclaurine', '6-Methoxy-7-hydroxy-(1R)-(4-hydroxyphenyl)methyl-1,2,3,4-tetrahydroisoquinoline', 'Coclaurine', '(R)-1,2,3,4-Tetrahydro-1-(4-hydroxyphenyl)methyl-6-methoxy-7-isoquinolinol', 'DL-Coclaurine', '(-)-Coclaurine', 'd-Coclaurine', '(R)-coclaurine'

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

Structure

SMILES: COC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O)C=C1)NCC2

InChI: InChI=1S/C17H19NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-5,9-10,15,18-20H,6-8H2,1H3/t15-/m0/s1

InChIKey: LVVKXRQZSRUVPY-HNNXBMFYSA-N

Reference

New Bisbenzylisoquinolines from Stephania pierrii

PubChem CID: 160487

CAS: 486-39-5

LOTUS: LTS0234039

NPASS: NPC277669

data_source: manually

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
Caulerpa taxifolia	Caulerpa	Caulerpaceae	Bryopsidales	Ulvophyceae	Chlorophyta	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
Aglaia odorata	Aglaia	Meliaceae	Sapindales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 285.3430000000001

TPSA？: 61.72

MolLogP？: 2.5359000000000007

Number of H-Donors: 3

Number of H-Acceptors: 4

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Rattus norvegicus	Dopamine transporter	IC50	14100.0	nM	10.1021/np50124a001
None	Unchecked	Ratio IC50	0.03	None	10.1021/np50124a001
None	Unchecked	Ratio IC50	0.35	None	10.1021/np50124a001

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT011650	COc1cc2c(cc1O)[C@@H](Cc1ccc(O)cc1)N(C)CC2.COc1cc2c(cc1O)[C@H](Cc1ccc(O)cc1)NCC2>>COc1cc2c(cc1O)[C@H](Cc1ccc(Oc3cc(C[C@@H]4c5cc(O)c(OC)cc5CCN4C)ccc3O)cc1)NCC2	R05210
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
AKRT011679	COc1cc2c(cc1O)[C@H](Cc1ccc(O)cc1)NCC2>>COc1cc2c(cc1O)[C@H](Cc1ccc(O)c(O)c1)NCC2	RXN-14879
AKRT011681	COc1cc2c(cc1O)[C@H](Cc1ccc(Oc3cc(C[C@@H]4c5cc(O)c(OC)cc5CCN4C)ccc3O)cc1)NCC2>>COc1cc2c(cc1O)[C@H](Cc1ccc(O)cc1)NCC2	MNXR149171
AKRT011697	COc1cc2c3c(c1O)C1(C=CC(=O)C=C1)C[C@H]3NCC2>>COc1cc2c(cc1O)[C@H](Cc1ccc(O)cc1)NCC2	MNXR184185
AKRT012666	C[33S].Oc1ccc(C[C@@H]2NCCc3cc(O)c(O)cc32)cc1>>COc1cc2c(cc1O)[C@H](Cc1ccc(O)cc1)NCC2	None
AKRT014746	C[SAH].Oc1ccc(CC2NCCc3cc(O)c(O)cc32)cc1>>COc1cc2c(cc1O)[C@H](Cc1ccc(O)cc1)NCC2	MNXR149141
AKRT014751	C[SAH].Oc1ccc(C[C@@H]2NCCc3cc(O)c(O)cc32)cc1>>COc1cc2c(cc1O)[C@H](Cc1ccc(O)cc1)NCC2	2.1.1.128-RXN