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name Structure Reference Source Properties Activities Metabolism

4-(2-Aminoethyl)phenol; N-(3,4-Dihydroxy-Z-cinnamoyl) 

AlkaPlorer ID: AK285426

Synonym: N-cis-Caffeoyltyramine 

IUPAC Name: (E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide

Structure

SMILES: OC(/C=C/C1=CC=C(O)C(O)=C1)=NCCC1=CC=C(O)C=C1

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InChI: InChI=1S/C17H17NO4/c19-14-5-1-12(2-6-14)9-10-18-17(22)8-4-13-3-7-15(20)16(21)11-13/h1-8,11,19-21H,9-10H2,(H,18,22)/b8-4+

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InChIKey: VSHUQLRHTJOKTA-XBXARRHUSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Crinum asiaticum Crinum Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Xylaria cubensis Xylaria Xylariaceae Xylariales Sordariomycetes Ascomycota Fungi Eukaryota
Bitis gabonica Bitis Viperidae Squamata Lepidosauria Chordata Metazoa Eukaryota
Mimusops caffra Mimusops Sapotaceae Ericales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Sesbania bispinosa Sesbania Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Crotalaria crispata Crotalaria Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Limonium sinense Limonium Plumbaginaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Oophaga pumilio Oophaga Dendrobatidae Anura Amphibia Chordata Metazoa Eukaryota
Atriplex parvifolia Atriplex Chenopodiaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Miliusa cuneata Miliusa Annonaceae Magnoliales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Strophanthus kombe Strophanthus Apocynaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Hesperocyparis arizonica Hesperocyparis Cupressaceae Cupressales Pinopsida Streptophyta Viridiplantae Eukaryota
Lespedeza bicolor Lespedeza Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Sorbaria sorbifolia Sorbaria Rosaceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Artemisia klotzchiana Artemisia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Nerine bowdenii Nerine Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lycium barbarum Lycium Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cotula cinerea Cotula Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Daphniphyllum paxianum Daphniphyllum Daphniphyllaceae Saxifragales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Angelica lucida Angelica Apiaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Artemisia juncea Artemisia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Penicillium herquei Penicillium Aspergillaceae Eurotiales Eurotiomycetes Ascomycota Fungi Eukaryota
Viburnum lantana Viburnum Adoxaceae Dipsacales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lycium chinense Lycium Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Veronica arvensis Veronica Plantaginaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 299.326

TPSA？: 93.28

MolLogP？: 3.0158000000000014

Number of H-Donors: 4

Number of H-Acceptors: 4

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Chlorocebus sabaeus Vero IC50 47800.0 nM 10.1021/acs.jnatprod.5b01054
Homo sapiens Beta-glucosidase Inhibition nan % 10.1016/j.ejmech.2016.02.044
Homo sapiens KB IC50 47800.0 nM 10.1021/acs.jnatprod.5b01054
Homo sapiens Tyrosinase Activity 30.0 % 10.1016/j.bmcl.2009.05.115
Homo sapiens Tyrosinase Inhibition 100.0 % 10.1016/j.bmcl.2006.01.022
Mus musculus B16 Activity 84.0 % 10.1016/j.bmcl.2009.05.115
Mus musculus B16 Activity nan None 10.1016/j.bmcl.2009.05.115
Mus musculus B16 IC50 nan None 10.1016/j.bmcl.2009.05.115
Mus musculus N2a Activity nan None 10.1021/acs.jnatprod.1c00435
Mus musculus Tyrosinase Activity 15.0 % 10.1016/j.bmcl.2009.05.115
Mus musculus Tyrosinase IC50 nan None 10.1016/j.bmcl.2009.05.115
Plasmodium falciparum Plasmodium falciparum IC50 23800.0 nM 10.1021/acs.jnatprod.5b01054
Plasmodium falciparum Plasmodium falciparum IC50 47800.0 nM 10.1021/acs.jnatprod.5b01054
Rattus norvegicus Rattus norvegicus Activity nan None 10.1016/j.bmcl.2006.01.022
None ADMET Retention_time 24.08 min 10.1021/acs.jnatprod.1c00435
None NON-PROTEIN TARGET IC50 44100.0 nM 10.1021/np300655y
None Radical scavenging activity Activity 40.0 % 10.1016/j.bmcl.2006.01.022
None Radical scavenging activity IC50 47600.0 nM 10.1021/np300655y
None Unchecked IC50 1860.0 nM 10.1016/j.ejmech.2016.02.044
None Unchecked Inhibition nan % 10.1016/j.ejmech.2016.02.044
None Unchecked Ki 1770.0 nM 10.1016/j.ejmech.2016.02.044

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT018406 NCCc1ccc(O)cc1.O=C([32S])/C=C/c1ccc(O)c(O)c1>>O=C(/C=C/c1ccc(O)c(O)c1)NCCc1ccc(O)cc1 None
AKRT023416 O=C([CoA])/C=C/c1ccc(O)c(O)c1.NCCc1ccc(O)cc1>>O=C(/C=C/c1ccc(O)c(O)c1)NCCc1ccc(O)cc1 enzymemap_28450