Molecule

Reticuline

AlkaPlorer ID: AK005848

Synonym: None

IUPAC Name: (1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol

Structure

SMILES: COC1=CC=C(C[C@H]2C3=CC(O)=C(OC)C=C3CCN2C)C=C1O

InChI: InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1

InChIKey: BHLYRWXGMIUIHG-HNNXBMFYSA-N

Reference

Anti-Platelet Aggregation Alkaloids and Lignans from <i>Hernandia nymphaeifolia</i>

PubChem CID: 439653

CAS: 485-19-8

LOTUS: LTS0181650

SuperNatural Ⅲ: SN0025618-02

NPASS: NPC476571

data_source: manually

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Crotalaria pallida	Crotalaria	Fabaceae	Fabales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Cercidiphyllum japonicum	Cercidiphyllum	Cercidiphyllaceae	Saxifragales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Lindera aggregata	Lindera	Lauraceae	Laurales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Stephania pierrei	Stephania	Menispermaceae	Ranunculales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Papaver somniferum	Papaver	Papaveraceae	Ranunculales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Fontinalis antipyretica	Fontinalis	Fontinalaceae	Hypnales	Bryopsida	Streptophyta	Viridiplantae	Eukaryota
Annona reticulata	Annona	Annonaceae	Magnoliales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Tinospora capillipes	Tinospora	Menispermaceae	Ranunculales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Paratinospora sagittata	Paratinospora	Menispermaceae	Ranunculales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Diplocarpon mali	Diplocarpon	Drepanopezizaceae	Helotiales	Leotiomycetes	Ascomycota	Fungi	Eukaryota
Cinnamomum camphora	Cinnamomum	Lauraceae	Laurales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Corydalis incisa	Corydalis	Papaveraceae	Ranunculales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Annona glabra	Annona	Annonaceae	Magnoliales	Magnoliopsida	Streptophyta	Viridiplantae	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
Corydalis ternata	Corydalis	Papaveraceae	Ranunculales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Hypserpa nitida	Hypserpa	Menispermaceae	Ranunculales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Thalictrum foliolosum	Thalictrum	Ranunculaceae	Ranunculales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Aloe microstigma	Aloe	Asphodelaceae	Asparagales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Caulerpa taxifolia	Caulerpa	Caulerpaceae	Bryopsidales	Ulvophyceae	Chlorophyta	Viridiplantae	Eukaryota
Tripterygium forrestii	Tripterygium	Celastraceae	Celastrales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Evolvulus nummularius	Evolvulus	Convolvulaceae	Solanales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Lactarius subumbonatus	Lactarius	Russulaceae	Russulales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota
Pleurocybella porrigens	Pleurocybella	Phyllotopsidaceae	Agaricales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota
None	Nectandra	Lauraceae	Laurales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Annona squamosa	Annona	Annonaceae	Magnoliales	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: 329.3960000000001

TPSA？: 62.16

MolLogP？: 2.8867000000000016

Number of H-Donors: 2

Number of H-Acceptors: 5

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Electrophorus electricus	Acetylcholinesterase	IC50	301010.0	nM	10.1016/j.bmc.2016.07.043
Electrophorus electricus	Acetylcholinesterase	IC50	nan	None	10.1007/s00044-008-9122-3
Electrophorus electricus	Acetylcholinesterase	Inhibition	52.96	%	10.1016/j.bmc.2016.07.043
Electrophorus electricus	Acetylcholinesterase	Inhibition	57.2	%	10.1007/s00044-008-9122-3
Electrophorus electricus	Acetylcholinesterase	Inhibition	nan	%	10.1007/s00044-008-9122-3
Equus caballus	Cholinesterase	IC50	65040.0	nM	10.1016/j.bmc.2016.07.043
Equus caballus	Cholinesterase	Inhibition	84.07	%	10.1016/j.bmc.2016.07.043
Equus caballus	Cholinesterase	Inhibition	nan	%	10.1007/s00044-008-9122-3
Hepatitis B virus	Hepatitis B virus	IC50	2143000.0	nM	10.1016/j.bmcl.2007.08.027
Hepatitis B virus	Hepatitis B virus	IC50	2994000.0	nM	10.1016/j.bmcl.2007.08.027
Homo sapiens	A549	IC50	30000.0	nM	10.1016/j.bmcl.2010.06.035
Homo sapiens	HCT-15	IC50	29440.0	nM	10.1016/j.bmcl.2010.06.035
Homo sapiens	SK-MEL-2	IC50	30000.0	nM	10.1016/j.bmcl.2010.06.035
Homo sapiens	SK-OV-3	IC50	30000.0	nM	10.1016/j.bmcl.2010.06.035
Hoplobatrachus tigerinus	Hoplobatrachus tigerinus	Activity	nan	None	10.1021/np50004a007
Mus musculus	Mus musculus	Activity	23.7	min	10.1021/np50004a007
Mus musculus	Mus musculus	Activity	56.2	min	10.1021/np50004a007
Mus musculus	Mus musculus	Activity	nan	None	10.1021/np50004a007
Mus musculus	Mus musculus	LD50	56.0	mg.kg-1	10.1021/np50004a007
Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	32.0	ug.mL-1	10.1021/np500538c
Plasmodium falciparum	Plasmodium falciparum	ED50	4050.0	ng/ml	10.1021/np50099a005
Plasmodium falciparum	Plasmodium falciparum	ED50	4470.0	ng/ml	10.1021/np50099a005
Plasmodium falciparum	Plasmodium falciparum	IC50	3.65	ug.mL-1	10.1021/np960195h
Plasmodium falciparum	Plasmodium falciparum	IC50	5.8	ug.mL-1	10.1021/np960195h
Rattus norvegicus	Aorta	Activity	100.0	%	10.1021/np960354x
Rattus norvegicus	Aorta	Activity	109.3	%	10.1021/np960354x
Rattus norvegicus	Aorta	Activity	110.5	%	10.1021/np960354x
Rattus norvegicus	Rattus norvegicus	Activity	0.36	degrees C	10.1021/np50004a007
Rattus norvegicus	Rattus norvegicus	Activity	0.69	degrees C	10.1021/np50004a007
Rattus norvegicus	Rattus norvegicus	Activity	1.1	degrees C	10.1021/np50004a007
Rattus norvegicus	Rattus norvegicus	Activity	7.8	s	10.1021/np50004a007
Rattus norvegicus	Rattus norvegicus	Activity	11.9	s	10.1021/np50004a007
Rattus norvegicus	Rattus norvegicus	Activity	60.0	%	10.1021/np50004a007
None	NON-PROTEIN TARGET	CC50	1909000.0	nM	10.1016/j.bmcl.2007.08.027
None	Platelet	Activity	39.2	%	10.1021/np960354x
None	Platelet	Activity	58.7	%	10.1021/np960354x
None	Platelet	Activity	84.2	%	10.1021/np960354x
None	Platelet	Activity	85.9	%	10.1021/np960354x
None	Unchecked	Ratio CC50/IC50	1.0	None	10.1016/j.bmcl.2007.08.027
None	Unchecked	Ratio IC50	0.22	None	10.1016/j.bmc.2016.07.043
None	Unchecked	Ratio IC50	4.63	None	10.1016/j.bmc.2016.07.043

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT011671	COc1cc2c(cc1O)[C@H](Cc1ccc(O)c(O)c1)N(C)CC2.C[33S]>>COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O	None
AKRT011672	COc1cc2c(cc1O)[C@H](Cc1ccc(O)c(O)c1)N(C)CC2.C[SAH]>>COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O	2.1.1.116-RXN
AKRT011794	COc1ccc(C[C@@H]2NCCc3cc(OC)c(O)cc32)cc1O.C[SAH]>>COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O	R05211
AKRT011813	COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O.C[33S]>>COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CC[N+]2(C)C)cc1O	None
AKRT011814	COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O.C[33S]>>COc1ccc(C[C@H]2c3cc(OC)c(OC)cc3CCN2C)cc1O	None
AKRT011815	COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O.C[SAH]>>COc1cc2c(cc1O)[C@H](Cc1ccc(OC)c(OC)c1)N(C)CC2	59532
AKRT011816	COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O.C[SAH]>>COc1ccc(CC2c3cc(OC)c(OC)cc3CCN2C)cc1O	R08787
AKRT011817	COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O.C[SAH]>>COc1ccc(C[C@@H]2c3cc(OC)c(OC)cc3CCN2C)cc1O	MNXR173590
AKRT011818	COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O.C[SAH]>>COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CC[N+]2(C)C)cc1O	RXN-18426
AKRT011819	COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O.C[SAH]>>COc1ccc(C[C@H]2c3cc(OC)c(OC)cc3CCN2C)cc1O	RXN-8700
AKRT011820	COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O>>COc1cc2c(cc1O)C[C@H]1c3c(cc(OC)c(O)c3-2)CCN1C	R08460
AKRT011821	COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O>>COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(O)c3CN1CC2	RETICULINE-OXIDASE-RXN
AKRT011822	COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O>>COc1cc2c(cc1O)[C@H](Cc1ccc(O)c(O)c1)N(C)CC2	enzymemap_25788
AKRT011823	COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O>>COc1cc2c(cc1O)[C@H](Cc1ccc(O)c(O)c1)N(C)CC2.C[33S]	None
AKRT011824	COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O>>COc1ccc(CC2=[N+](C)CCc3cc(OC)c(O)cc32)cc1O	RXN-8142
AKRT011825	COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O>>COc1ccc2c(c1O)-c1c(O)c(OC)cc3c1[C@H](C2)N(C)CC3	RXN-9314
AKRT014592	C[SAH].C[SAH].C[SAH].Oc1ccc(C[C@@H]2NCCc3cc(O)c(O)cc32)cc1O>>COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O	RXN-9981