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Rocaglamide

AlkaPlorer ID: AK006305

Synonym: None

IUPAC Name: (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide

Structure

SMILES: COC1=CC=C([C@@]23OC4=CC(OC)=CC(OC)=C4[C@]2(O)[C@H](O)[C@H](C(=O)N(C)C)[C@H]3C2=CC=CC=C2)C=C1

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InChI: InChI=1S/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1

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InChIKey: DAPAQENNNINUPW-IDAMAFBJSA-N

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Properties Information

Molecule Weight: 505.5670000000002

TPSA？: 97.69

MolLogP？: 3.050600000000001

Number of H-Donors: 2

Number of H-Acceptors: 7

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Alternaria citri Alternaria citri EC50 200.0 ug.mL-1 10.1021/jf990509h
Alternaria citri Alternaria citri EC90 200.0 ug ml-1 10.1021/jf990509h
Alternaria citri Alternaria citri MIC 200.0 ug.mL-1 10.1021/jf990509h
Fusarium avenaceum Fusarium avenaceum EC50 8.0 ug.mL-1 10.1021/jf990509h
Fusarium avenaceum Fusarium avenaceum EC90 66.0 ug ml-1 10.1021/jf990509h
Fusarium avenaceum Fusarium avenaceum MIC 200.0 ug.mL-1 10.1021/jf990509h
Hepacivirus hominis Hepatitis C virus EC50 4.0 nM 10.1016/j.ejmech.2020.112653
Homo sapiens 786-0 GI50 9.528 nM None
Homo sapiens A498 GI50 7.907 nM None
Homo sapiens A549 GI50 3.532 nM None
Homo sapiens A549 IC50 0.006 ug.mL-1 10.1021/np970163+
Homo sapiens ACHN GI50 3.436 nM None
Homo sapiens Alpha-synuclein Potency 10000.0 nM None
Homo sapiens Ataxin-2 Potency 39810.7 nM None
Homo sapiens BT-549 GI50 58.34 nM None
Homo sapiens CAKI-1 GI50 29.24 nM None
Homo sapiens CCRF-CEM GI50 3.664 nM None
Homo sapiens COLO 205 GI50 6.471 nM None
Homo sapiens DU-145 GI50 8.091 nM None
Homo sapiens EKVX GI50 20.32 nM None
Homo sapiens Eukaryotic initiation factor 4A-I IC50 4.7 nM 10.1021/acs.jmedchem.0c00182
Homo sapiens Eukaryotic initiation factor 4A-I IC50 47.0 nM 10.1021/acs.jmedchem.0c00182
Homo sapiens Eukaryotic initiation factor 4A-I IC50 135.0 nM 10.1021/acs.jmedchem.0c00182
Homo sapiens Eukaryotic initiation factor 4A-I IC50 231.0 nM 10.1021/acs.jmedchem.0c00182
Homo sapiens Eukaryotic initiation factor 4A-I Kd 156.0 nM 10.1021/acs.jmedchem.0c00182
Homo sapiens Geminin Potency 3662.6 nM None
Homo sapiens Geminin Potency 7307.8 nM None
Homo sapiens Glycoprotein hormones alpha chain Potency 2511.9 nM None
Homo sapiens HCC 2998 GI50 2.891 nM None
Homo sapiens HCT-116 GI50 3.162 nM None
Homo sapiens HCT-15 GI50 17.58 nM None
Homo sapiens HCT-8 IC50 0.007 ug.mL-1 10.1021/np970163+
Homo sapiens HEK293 Potency 125.9 nM None
Homo sapiens HeLa IC50 100.0 nM 10.1021/acs.jmedchem.0c01746
Homo sapiens HL-60 GI50 3.828 nM None
Homo sapiens HOP-62 GI50 9.727 nM None
Homo sapiens HOP-92 GI50 13.77 nM None
Homo sapiens Hs-578T GI50 8.75 nM None
Homo sapiens HT-29 ED50 0.005 uM 10.1021/np3007588
Homo sapiens HT-29 GI50 2.244 nM None
Homo sapiens IGROV-1 GI50 6.124 nM None
Homo sapiens Isocitrate dehydrogenase [NADP] cytoplasmic Potency 6.5 nM None
Homo sapiens K562 GI50 2.366 nM None
Homo sapiens KB IC50 0.006 ug.mL-1 10.1021/np970163+
Homo sapiens KM12 GI50 2.944 nM None
Homo sapiens LOX IMVI GI50 1.914 nM None
Homo sapiens M14 GI50 3.266 nM None
Homo sapiens Malme-3M GI50 4.285 nM None
Homo sapiens MCF7 GI50 2.924 nM None
Homo sapiens MDA-MB-231 GI50 7.762 nM None
Homo sapiens MDA-MB-231 IC50 20.0 nM 10.1021/acs.jmedchem.0c00182
Homo sapiens MDA-MB-435 GI50 3.597 nM None
Homo sapiens MDA-N GI50 3.548 nM None
Homo sapiens MOLT-4 GI50 1.919 nM None
Homo sapiens NCI/ADR-RES GI50 30.55 nM None
Homo sapiens NCI-H226 GI50 11.27 nM None
Homo sapiens NCI-H23 GI50 8.851 nM None
Homo sapiens NCI-H322M GI50 9.727 nM None
Homo sapiens NCI-H460 GI50 2.704 nM None
Homo sapiens NCI-H522 GI50 10.4 nM None
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 14.6 nM None
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 20.6 nM None
Homo sapiens Nuclear factor NF-kappa-B p105 subunit ED50 2.0 uM 10.1021/np9001724
Homo sapiens Nuclear factor NF-kappa-B p105 subunit IC50 75.0 nM 10.1021/np1002065
Homo sapiens Nuclear factor NF-kappa-B p105 subunit IC50 2000.0 nM 10.1021/np900517h
Homo sapiens Nuclear factor NF-kappa-B p65 subunit ED50 0.08 uM 10.1021/np3007588
Homo sapiens Nuclear factor NF-kappa-B p65 subunit IC50 70.0 nM 10.1016/j.bmc.2018.07.025
Homo sapiens Nuclear factor NF-kappa-B p65 subunit IC50 75.0 nM 10.1021/np200051j
Homo sapiens Nuclear factor NF-kappa-B p65 subunit IC50 75.0 nM 10.1021/np200062x
Homo sapiens Nuclear factor NF-kappa-B p65 subunit IC50 80.0 nM 10.1021/np900517h
Homo sapiens Nuclear factor NF-kappa-B p65 subunit IC50 120.0 nM 10.1021/acs.jnatprod.9b00140
Homo sapiens Nuclear factor NF-kappa-B p65 subunit IC50 4000.0 nM 10.1021/np1002065
Homo sapiens OVCAR-3 GI50 55.98 nM None
Homo sapiens OVCAR-4 GI50 20.65 nM None
Homo sapiens OVCAR-5 GI50 9.908 nM None
Homo sapiens OVCAR-8 GI50 10.91 nM None
Homo sapiens PC-3 GI50 8.356 nM None
Homo sapiens RPMI-7951 IC50 0.002 ug.mL-1 10.1021/np970163+
Homo sapiens RPMI-8226 GI50 5.546 nM None
Homo sapiens RXF 393 GI50 20.56 nM None
Homo sapiens SF-268 GI50 8.492 nM None
Homo sapiens SF-295 GI50 4.498 nM None
Homo sapiens SF-539 GI50 1.69 nM None
Homo sapiens SK-MEL-2 GI50 19.68 nM None
Homo sapiens SK-MEL-28 GI50 6.887 nM None
Homo sapiens SK-MEL-5 GI50 3.013 nM None
Homo sapiens SK-OV-3 GI50 5.754 nM None
Homo sapiens SN12C GI50 8.147 nM None
Homo sapiens SNB-19 GI50 267.3 nM None
Homo sapiens SNB-75 GI50 9.354 nM None
Homo sapiens SR GI50 1.622 nM None
Homo sapiens SW-620 GI50 2.992 nM None
Homo sapiens T47D GI50 2.188 nM None
Homo sapiens TAR DNA-binding protein 43 Potency 31622.8 nM None
Homo sapiens TE-671 IC50 0.006 ug.mL-1 10.1021/np970163+
Homo sapiens TK-10 GI50 14.55 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 7.3 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 9.2 nM None
Homo sapiens U-251 GI50 6.053 nM None
Homo sapiens UACC-257 GI50 18.37 nM None
Homo sapiens UACC-62 GI50 6.761 nM None
Homo sapiens UO-31 GI50 15.85 nM None
Mus musculus Eukaryotic initiation factor 4A-I Activity nan None 10.1016/j.bmcl.2015.12.045
Mus musculus Eukaryotic initiation factor 4A-II Activity nan None 10.1016/j.bmcl.2015.12.045
Mus musculus P388 IC50 0.005 ug.mL-1 10.1021/np970163+
Mus musculus P388 T/C 156.0 % 10.1021/np970163+
Pyricularia grisea Pyricularia grisea EC50 0.9 ug.mL-1 10.1021/jf990509h
Pyricularia grisea Pyricularia grisea EC90 35.0 ug ml-1 10.1021/jf990509h
Pyricularia grisea Pyricularia grisea MIC 25.0 ug.mL-1 10.1021/jf990509h
None ADMET ED50 50.0 uM 10.1021/np3007588
None NON-PROTEIN TARGET Activity 77.6 % 10.1021/np970163+
None NON-PROTEIN TARGET Activity 83.8 % 10.1021/np970163+
None NON-PROTEIN TARGET Activity 85.5 % 10.1021/np970163+
None NON-PROTEIN TARGET Activity 90.5 % 10.1021/np970163+
None NON-PROTEIN TARGET IC50 3900.0 nM 10.1021/acs.jnatprod.5b01079
None Unchecked AC50 260.0 nM None
None Unchecked AC50 889.0 nM None
None Unchecked IC50 2000.0 nM 10.1016/j.bmcl.2006.09.084
None Unchecked IC50 2600.0 nM 10.1021/acs.jnatprod.5b01079
None Unchecked Potency 0.1 nM None
None Unchecked Potency 51.7 nM None
None Unchecked Potency 58.0 nM None
None Unchecked Potency 112.2 nM None
None Unchecked Potency 163.6 nM None
None Unchecked Potency 6309.6 nM None
None Unchecked Potency 100000.0 nM None

Metabolism Information