Molecule

5-Hydroxytryptamine; Nb-(4-Hydroxy-3-methoxy-Z-cinnamoyl)

AlkaPlorer ID: AK302131

Synonym: Nb-(Z)-Feruloylserotonin, cis-Moschamine

IUPAC Name: (E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide

Structure

SMILES: COC1=CC(/C=C/C(O)=NCCC2=CNC3=CC=C(O)C=C23)=CC=C1O

InChI: InChI=1S/C20H20N2O4/c1-26-19-10-13(2-6-18(19)24)3-7-20(25)21-9-8-14-12-22-17-5-4-15(23)11-16(14)17/h2-7,10-12,22-24H,8-9H2,1H3,(H,21,25)/b7-3+

InChIKey: WGHKJYWENWLOMY-XVNBXDOJSA-N

Reference

Dibenzylbutyrolactone lignans and indole alkaloids from the seeds of Centaurea nigra (Asteraceae)

PubChem CID: 5969616

CAS: 193224-24-7

LOTUS: LTS0064948

NPASS: NPC266931

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Centella asiatica	Centella	Apiaceae	Apiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Centaurea cyanus	Centaurea	Asteraceae	Asterales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 352.39000000000004

TPSA？: 98.07

MolLogP？: 3.800100000000002

Number of H-Donors: 4

Number of H-Acceptors: 4

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Agaricus bisporus	Tyrosinase	IC50	8000.0	nM	10.1016/j.bmcl.2011.02.028
Homo sapiens	Cyclooxygenase-1	Inhibition	2.7	%	10.1016/j.bmcl.2012.02.002
Homo sapiens	Cyclooxygenase-2	Inhibition	18.8	%	10.1016/j.bmcl.2012.02.002
Homo sapiens	Proto-oncogene c-JUN	Inhibition	nan	%	10.1016/j.bmcl.2017.10.035
Homo sapiens	Tyrosinase	Activity	48.0	%	10.1016/j.bmcl.2009.05.115
Mus musculus	B16	Activity	100.0	%	10.1016/j.bmcl.2009.05.115
Mus musculus	B16	Activity	nan	None	10.1016/j.bmcl.2009.05.115
Mus musculus	B16	IC50	23000.0	nM	10.1016/j.bmcl.2009.05.115
Mus musculus	MAP kinase p38	Inhibition	nan	%	10.1016/j.bmcl.2017.10.035
Mus musculus	Proto-oncogene c-Fos	Inhibition	nan	%	10.1016/j.bmcl.2017.10.035
Mus musculus	RAW264.7	Activity	nan	None	10.1016/j.bmcl.2017.10.035
Mus musculus	RAW264.7	IC50	14740.0	nM	10.1016/j.bmcl.2017.10.035
Mus musculus	RAW264.7	IC50	123140.0	nM	10.1016/j.bmcl.2017.10.035
Mus musculus	RAW264.7	Inhibition	25.1	%	10.1016/j.bmcl.2017.10.035
Mus musculus	RAW264.7	Inhibition	52.17	%	10.1016/j.bmcl.2017.10.035
Mus musculus	RAW264.7	Inhibition	nan	%	10.1016/j.bmcl.2017.10.035
Mus musculus	Transcription factor AP-1	Inhibition	nan	%	10.1016/j.bmcl.2017.10.035
Mus musculus	Tyrosinase	Activity	29.0	%	10.1016/j.bmcl.2009.05.115
Mus musculus	Tyrosinase	IC50	216000.0	nM	10.1016/j.bmcl.2009.05.115
Mus musculus	Tyrosine-protein kinase JAK1	Inhibition	nan	%	10.1016/j.bmcl.2017.10.035
Saccharomyces cerevisiae	Alpha-glucosidase MAL62	IC50	99800.0	nM	10.1007/s00044-011-9699-9
Saccharomyces cerevisiae	Alpha-glucosidase MAL62	Inhibition	nan	%	10.1007/s00044-011-9699-9
Saccharomyces cerevisiae	Alpha-glucosidase MAL62	Ki	129800.0	nM	10.1007/s00044-011-9699-9
None	NON-PROTEIN TARGET	IC50	81000.0	nM	10.1016/j.bmc.2014.10.011
None	Radical scavenging activity	EC50	22800.0	nM	10.1016/j.bmcl.2011.02.028
None	Unchecked	Inhibition	nan	%	10.1016/j.bmcl.2017.10.035

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT011507	COc1cc(/C=C/C(=O)[CoA])ccc1O.NCCc1c[nH]c2ccc(O)cc12>>COc1cc(/C=C/C(=O)NCCc2c[nH]c3ccc(O)cc23)ccc1O	RXN-8710