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4-(2-Aminoethyl)phenol; N-(4-Hydroxy-Z-cinnamoyl) 

AlkaPlorer ID: AK285432

Synonym: N-p-cis-Coumaroyltyramine 

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

Structure

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

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InChI: InChI=1S/C17H17NO3/c19-15-6-1-13(2-7-15)5-10-17(21)18-12-11-14-3-8-16(20)9-4-14/h1-10,19-20H,11-12H2,(H,18,21)/b10-5+

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InChIKey: RXGUTQNKCXHALN-BJMVGYQFSA-N

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Reference

An azaanthracene alkaloid from Polyalthia suberosa

PubChem CID: 5372945

CAS: 111129-11-4

LOTUS: LTS0067822

SuperNatural Ⅲ: SN0337741-02

NPASS: NPC24101

data_source: manually

Source

Species Genus Family Order Class Phylum Kingdom Domain
Phlomis crinita Phlomis Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Sarcophyton flexuosum Sarcophyton Alcyoniidae Malacalcyonacea Anthozoa Cnidaria Metazoa Eukaryota
Glycosmis pseudoracemosa Glycosmis Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ophiopogon japonicus Ophiopogon Asparagaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Meconopsis horridula Meconopsis Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Solanum lasiocarpum Solanum Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Anemarrhena asphodeloides Anemarrhena Asparagaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cota tinctoria Cota Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Atraphaxis frutescens Atraphaxis Polygonaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aspergillus microcysticus Aspergillus Aspergillaceae Eurotiales Eurotiomycetes Ascomycota Fungi Eukaryota
Juniperus horizontalis Juniperus Cupressaceae Cupressales Pinopsida Streptophyta Viridiplantae Eukaryota
Rhododendron mucronulatum Rhododendron Ericaceae Ericales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Viburnum lantana Viburnum Adoxaceae Dipsacales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Asimina triloba Asimina Annonaceae Magnoliales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Creosphaeria sassafras Creosphaeria Xylariaceae Xylariales Sordariomycetes Ascomycota Fungi Eukaryota
Juniperus scopulorum Juniperus Cupressaceae Cupressales Pinopsida Streptophyta Viridiplantae Eukaryota
Balanophora japonica Balanophora Balanophoraceae Santalales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Emericellopsis minima Emericellopsis None Hypocreales Sordariomycetes Ascomycota Fungi Eukaryota
Salmonella enterica Salmonella Enterobacteriaceae Enterobacterales Gammaproteobacteria Pseudomonadota None Bacteria
Costasiella ocellifera Costasiella Costasiellidae None Gastropoda Mollusca Metazoa Eukaryota
Lycium chinense Lycium Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Euonymus fortunei Euonymus Celastraceae Celastrales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Hesperocyparis arizonica Hesperocyparis Cupressaceae Cupressales Pinopsida Streptophyta Viridiplantae Eukaryota
Clerodendrum trichotomum Clerodendrum Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Hygrophorus eburneus Hygrophorus Hygrophoraceae Agaricales Agaricomycetes Basidiomycota Fungi Eukaryota
Pellacalyx axillaris Pellacalyx Rhizophoraceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Oryza sativa Oryza Poaceae Poales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Humulus japonicus Humulus Cannabaceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aristolochia manshuriensis Aristolochia Aristolochiaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Morella pensylvanica Morella Myricaceae Fagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Eucalyptus albens Eucalyptus Myrtaceae Myrtales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Piper kadsura Piper Piperaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Crinum asiaticum Crinum Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Senecio congestus Senecio Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Inula grantioides Inula Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lycium barbarum Lycium Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Gaillardia powellii Gaillardia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Artemisia juncea Artemisia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Miliusa cuneata Miliusa Annonaceae Magnoliales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Boschniakia rossica Boschniakia Orobanchaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Plectranthus caninus Plectranthus Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Plectosphaerella cucumerina Plectosphaerella Plectosphaerellaceae Glomerellales Sordariomycetes Ascomycota Fungi Eukaryota
Capsicum annuum Capsicum Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Corynanthe pachyceras Corynanthe Rubiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Melampodium leucanthum Melampodium Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Crotalaria crispata Crotalaria Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Tribulus terrestris Tribulus Zygophyllaceae Zygophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lupinus cosentinii Lupinus Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cannabis sativa Cannabis Cannabaceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Alexandrium excavatum Alexandrium Pyrocystaceae Gonyaulacales Dinophyceae None None Eukaryota
Dasymaschalon dasymaschalum Dasymaschalon Annonaceae Magnoliales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Crotalaria stolzii Crotalaria Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Coffea liberica Coffea Rubiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Tinospora baenzigeri Tinospora Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Stellaria media Stellaria Caryophyllaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Renealmia alpinia Renealmia Zingiberaceae Zingiberales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Atriplex parvifolia Atriplex Chenopodiaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Bursera kerberi Bursera Burseraceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Strychnos spinosa Strychnos Loganiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
None Erycibe Convolvulaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
None Erycibe Convolvulaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Rauvolfia salicifolia Rauvolfia Apocynaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Beesia calthifolia Beesia Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Annona cherimola Annona Annonaceae Magnoliales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Curcuma aeruginosa Curcuma Zingiberaceae Zingiberales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cynoglossum amabile Cynoglossum Boraginaceae Boraginales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Arcangelisia gusanlung Arcangelisia Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Sideritis dasygnaphala Sideritis Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Alchornea cordifolia Alchornea Euphorbiaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Streptomyces parvisporogenes Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria
Euploca racemosa Euploca Heliotropiaceae Boraginales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Tephroseris kirilowii Tephroseris Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Solanum violaceum Solanum Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lathyrus tingitanus Lathyrus Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Botrychium ternatum Botrychium Ophioglossaceae Ophioglossales Polypodiopsida Streptophyta Viridiplantae Eukaryota
Clinacanthus nutans Clinacanthus Acanthaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Nelumbo nucifera Nelumbo Nelumbonaceae Proteales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Solanum melongena Solanum Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Piper brachystachyum Piper Piperaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Alstonia angustiloba Alstonia Apocynaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Streptomyces melanogenes Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria
Tetradium glabrifolium Tetradium Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Senecio provincialis Senecio Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Micromonospora echinospora Micromonospora Micromonosporaceae Micromonosporales Actinomycetes Actinomycetota None Bacteria

Properties Information

Molecule Weight: 283.327

TPSA？: 73.05

MolLogP？: 3.310200000000002

Number of H-Donors: 3

Number of H-Acceptors: 3

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Agaricus bisporus Tyrosinase IC50 1000000.0 nM 10.1021/np100900k
Agaricus bisporus Tyrosinase Inhibition nan % 10.1007/s00044-012-0419-x
Agaricus bisporus Tyrosinase Inhibition nan % 10.1016/j.bmc.2017.12.011
Artemia Artemia LC50 6.7 ug.mL-1 10.1021/np50081a011
Chlorocebus sabaeus Vero IC50 47800.0 nM 10.1021/acs.jnatprod.5b01054
Homo sapiens 786-0 GI50 12502.59 nM None
Homo sapiens A498 GI50 12502.59 nM None
Homo sapiens A549 ED50 3.24 ug ml-1 10.1021/np50081a011
Homo sapiens A549 GI50 4064.43 nM None
Homo sapiens A549 IC50 15.21 ug.mL-1 10.1021/np200877u
Homo sapiens ACHN GI50 3491.4 nM None
Homo sapiens Beta-glucosidase Inhibition nan % 10.1016/j.ejmech.2016.02.044
Homo sapiens BT-549 GI50 7533.56 nM None
Homo sapiens Ca9-22 IC50 12.28 ug.mL-1 10.1021/np200877u
Homo sapiens CAKI-1 GI50 10185.91 nM None
Homo sapiens CCRF-CEM GI50 2985.38 nM None
Homo sapiens COLO 205 GI50 12502.59 nM None
Homo sapiens DU-145 GI50 11994.99 nM None
Homo sapiens EKVX GI50 3047.89 nM None
Homo sapiens HCT-116 GI50 12502.59 nM None
Homo sapiens HCT-15 GI50 12502.59 nM None
Homo sapiens HepG2 IC50 9.57 ug.mL-1 10.1021/np200877u
Homo sapiens HepG2 Inhibition 39.0 % 10.1021/acs.jnatprod.8b00483
Homo sapiens HL-60 GI50 3580.96 nM None
Homo sapiens HOP-62 GI50 12502.59 nM None
Homo sapiens HOP-92 GI50 5140.44 nM None
Homo sapiens Hs-578T GI50 12502.59 nM None
Homo sapiens HT-29 ED50 6.74 10'-1 ug/ml 10.1021/np50081a011
Homo sapiens HT-29 GI50 12502.59 nM None
Homo sapiens IGROV-1 GI50 8298.51 nM None
Homo sapiens K562 GI50 5597.58 nM None
Homo sapiens KB IC50 47800.0 nM 10.1021/acs.jnatprod.5b01054
Homo sapiens KM12 GI50 12502.59 nM None
Homo sapiens LOX IMVI GI50 12502.59 nM None
Homo sapiens M14 GI50 12502.59 nM None
Homo sapiens Malme-3M GI50 12502.59 nM None
Homo sapiens MCF7 ED50 7.16 10'-1 ug/ml 10.1021/np50081a011
Homo sapiens MCF7 GI50 12502.59 nM None
Homo sapiens MCF7 IC50 20.0 ug.mL-1 10.1021/np200877u
Homo sapiens MDA-MB-231 GI50 12502.59 nM None
Homo sapiens MDA-MB-231 IC50 20.0 ug.mL-1 10.1021/np200877u
Homo sapiens MDA-MB-435 GI50 12502.59 nM None
Homo sapiens MDA-N GI50 12502.59 nM None
Homo sapiens NCI/ADR-RES GI50 3622.43 nM None
Homo sapiens NCI-H226 GI50 12502.59 nM None
Homo sapiens NCI-H23 GI50 7161.43 nM None
Homo sapiens NCI-H322M GI50 10209.39 nM None
Homo sapiens NCI-H460 GI50 11194.38 nM None
Homo sapiens NCI-H522 GI50 3380.65 nM None
Homo sapiens OVCAR-3 GI50 8933.05 nM None
Homo sapiens OVCAR-4 GI50 8629.79 nM None
Homo sapiens OVCAR-5 GI50 12502.59 nM None
Homo sapiens OVCAR-8 GI50 12502.59 nM None
Homo sapiens PC-3 GI50 8570.38 nM None
Homo sapiens RPMI-8226 GI50 6950.24 nM None
Homo sapiens RXF 393 GI50 12502.59 nM None
Homo sapiens SF-268 GI50 9571.94 nM None
Homo sapiens SF-295 GI50 8128.31 nM None
Homo sapiens SF-539 GI50 3133.29 nM None
Homo sapiens SK-MEL-2 GI50 12502.59 nM None
Homo sapiens SK-MEL-28 GI50 12502.59 nM None
Homo sapiens SK-MEL-5 GI50 12502.59 nM None
Homo sapiens SN12C GI50 5000.35 nM None
Homo sapiens SNB-19 GI50 12502.59 nM None
Homo sapiens SR GI50 4017.91 nM None
Homo sapiens SW-620 GI50 12502.59 nM None
Homo sapiens T47D GI50 12502.59 nM None
Homo sapiens TK-10 GI50 3723.92 nM None
Homo sapiens U-251 GI50 12502.59 nM None
Homo sapiens UACC-257 GI50 12502.59 nM None
Homo sapiens UACC-62 GI50 7413.1 nM None
Homo sapiens UO-31 GI50 11091.75 nM None
Mus musculus 3T3-L1 Activity nan None 10.1016/j.bmcl.2013.04.013
Mus musculus B16-F10 Activity nan None 10.1021/np100900k
Mus musculus BV-2 Activity nan None 10.1021/acs.jnatprod.1c00055
Mus musculus BV-2 IC50 2200.0 nM 10.1021/acs.jnatprod.1c00055
Mus musculus N2a Activity nan None 10.1021/acs.jnatprod.1c00435
Paracoccus sp. Paracoccus sp. EC50 300000.0 nM 10.1016/j.bmcl.2017.11.039
Plasmodium falciparum Plasmodium falciparum IC50 47800.0 nM 10.1021/acs.jnatprod.5b01054
Pseudoalteromonas lipolytica Pseudoalteromonas lipolytica EC50 300000.0 nM 10.1016/j.bmcl.2017.11.039
Pseudoalteromonas ulvae Pseudoalteromonas ulvae EC50 75500.0 nM 10.1016/j.bmcl.2017.11.039
Rattus norvegicus Glutamate NMDA receptor; Grin1/Grin2a IC50 100000.0 nM 10.1021/jm990199u
Rattus norvegicus Glutamate NMDA receptor; Grin1/Grin2b IC50 21000.0 nM 10.1021/jm990199u
Rattus norvegicus Glutamate NMDA receptor; Grin1/Grin2c IC50 100000.0 nM 10.1021/jm990199u
Sus scrofa Pancreatic triacylglycerol lipase Inhibition nan % 10.1016/j.bmcl.2013.04.013
None ADMET Activity nan None 10.1021/np200877u
None ADMET Retention_time 27.32 min 10.1021/acs.jnatprod.1c00435
None NON-PROTEIN TARGET Activity nan None 10.1021/np900593q
None NON-PROTEIN TARGET IC50 11.23 ug.mL-1 10.1021/np200877u
None NON-PROTEIN TARGET IC50 8400.0 nM 10.1021/np0505521
None NON-PROTEIN TARGET IC50 52600.0 nM 10.1021/np300655y
None NON-PROTEIN TARGET Inhibition -0.17 % 10.1021/np200877u
None NON-PROTEIN TARGET Inhibition 23.24 % 10.1021/np200877u
None No relevant target IC50 200000.0 nM 10.1021/acs.jnatprod.6b00720
None Radical scavenging activity IC50 63500.0 nM 10.1021/np300655y
None Unchecked IC50 420.0 nM 10.1016/j.ejmech.2016.02.044
None Unchecked IC50 4500.0 nM 10.1021/acs.jnatprod.9b00506
None Unchecked IC50 21000.0 nM 10.1016/s0960-894x(97)10215-3
None Unchecked IC50 92400.0 nM 10.1021/acs.jnatprod.6b00720
None Unchecked IC50 200000.0 nM 10.1016/s0960-894x(97)10215-3
None Unchecked IC50 300000.0 nM 10.1016/s0960-894x(97)10215-3
None Unchecked IC50 5000000.0 nM 10.1021/acs.jnatprod.6b00720
None Unchecked Inhibition nan % 10.1016/j.ejmech.2016.02.044
None Unchecked Inhibition nan % 10.1021/acs.jnatprod.0c00564
None Unchecked Ki 350.0 nM 10.1016/j.ejmech.2016.02.044
None Unchecked Ratio 1.029 None 10.1016/j.ejmech.2016.02.044
None Unchecked Ratio 1.034 None 10.1016/j.ejmech.2016.02.044
None Unchecked Ratio 1.037 None 10.1016/j.ejmech.2016.02.044
None Unchecked Ratio 1.053 None 10.1016/j.ejmech.2016.02.044

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT018407 NCCc1ccc(O)cc1.O=C([32S])/C=C/c1ccc(O)cc1>>O=C(/C=C/c1ccc(O)cc1)NCCc1ccc(O)cc1 None
AKRT018409 NCCc1ccc(O)cc1.O=C([CoA])/C=C/c1ccc(O)cc1>>O=C(/C=C/c1ccc(O)cc1)NCCc1ccc(O)cc1 RXN-8715
AKRT023426 O=C([CoA])/C=C/c1ccc(O)cc1.NCCc1ccc(O)cc1>>O=C(/C=C/c1ccc(O)cc1)NCCc1ccc(O)cc1 enzymemap_28449