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Scoulerine

AlkaPlorer ID: AK001287

Synonym: None

IUPAC Name: (13aS)-3,10-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,9-diol

Structure

SMILES: COC1=C(O)C=C2C(=C1)CCN1CC3=C(O)C(OC)=CC=C3C[C@@H]21

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InChI: InChI=1S/C19H21NO4/c1-23-17-4-3-11-7-15-13-9-16(21)18(24-2)8-12(13)5-6-20(15)10-14(11)19(17)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1

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InChIKey: KNWVMRVOBAFFMH-HNNXBMFYSA-N

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Properties Information

Molecule Weight: 327.38

TPSA？: 62.16000000000001

MolLogP？: 2.770500000000001

Number of H-Donors: 2

Number of H-Acceptors: 5

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens A549 IC50 26320.0 nM 10.1021/acs.jnatprod.1c00429
Homo sapiens Apoptotic protease-activating factor 1 IC50 16300.0 nM None
Homo sapiens Apoptotic protease-activating factor 1 IC50 100000.0 nM None
Homo sapiens Ataxin-2 Potency 44668.4 nM None
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 12589.3 nM None
Homo sapiens DNA dC->dU-editing enzyme APOBEC-3F Potency 11155.6 nM None
Homo sapiens DNA dC->dU-editing enzyme APOBEC-3F Potency 12516.8 nM None
Homo sapiens DNA dC->dU-editing enzyme APOBEC-3G Potency 11220.2 nM None
Homo sapiens DNA dC->dU-editing enzyme APOBEC-3G Potency 12516.8 nM None
Homo sapiens DNA polymerase eta Potency 89125.1 nM None
Homo sapiens DNA polymerase iota Potency 10000.0 nM None
Homo sapiens Dopamine D1 receptor Inhibition 99.1 % 10.1016/j.bmc.2012.12.016
Homo sapiens Dopamine D1 receptor Ki 22.0 nM 10.1016/j.bmc.2012.12.016
Homo sapiens Dopamine D2 receptor Inhibition 93.4 % 10.1016/j.bmc.2012.12.016
Homo sapiens Dopamine D2 receptor Ki 214.0 nM 10.1016/j.bmc.2012.12.016
Homo sapiens Flap endonuclease 1 Potency 4466.8 nM None
Homo sapiens Geminin Potency 4610.9 nM None
Homo sapiens Geminin Potency 20596.2 nM None
Homo sapiens GES1 IC50 95300.0 nM 10.1016/j.bmc.2022.116705
Homo sapiens Glucagon-like peptide 1 receptor Potency 10000.0 nM None
Homo sapiens HeLa IC50 6737.0 nM 10.1021/acs.jnatprod.1c00429
Homo sapiens HGC-27 IC50 6100.0 nM 10.1016/j.bmc.2022.116705
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 14125.4 nM None
Homo sapiens Isocitrate dehydrogenase [NADP] cytoplasmic Potency 2592.9 nM None
Homo sapiens Isocitrate dehydrogenase [NADP] cytoplasmic Potency 50118.7 nM None
Homo sapiens Lethal(3)malignant brain tumor-like protein 1 Potency 15848.9 nM None
Homo sapiens MDA-MB-231 IC50 7324.0 nM 10.1021/acs.jnatprod.1c00429
Homo sapiens MGC-803 IC50 12600.0 nM 10.1016/j.bmc.2022.116705
Homo sapiens NCI-H23 IC50 2541.0 nM 10.1021/acs.jnatprod.1c00429
Homo sapiens NCI-H460 Activity nan None 10.1021/acs.jnatprod.1c00429
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 29092.9 nM None
Homo sapiens Serine/threonine-protein kinase Aurora-A Inhibition nan % 10.1021/acs.jnatprod.1c00429
Homo sapiens Serine/threonine-protein kinase Aurora-B Inhibition nan % 10.1021/acs.jnatprod.1c00429
Homo sapiens Serotonin 1a (5-HT1a) receptor Inhibition 14.2 % 10.1016/j.bmc.2012.12.016
Homo sapiens Serotonin 1a (5-HT1a) receptor Ki nan None 10.1016/j.bmc.2012.12.016
Homo sapiens Serotonin 2a (5-HT2a) receptor Inhibition 20.9 % 10.1016/j.bmc.2012.12.016
Homo sapiens Serotonin 2a (5-HT2a) receptor Ki nan None 10.1016/j.bmc.2012.12.016
Homo sapiens SW480 IC50 4237.0 nM 10.1021/acs.jnatprod.1c00429
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 4109.5 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 4610.9 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 2 IC50 128332.0 nM None
Homo sapiens Ubiquitin carboxyl-terminal hydrolase 1 Potency 14125.4 nM None
Plasmodium falciparum Plasmodium falciparum Potency 6573.3 nM None
Plasmodium falciparum Plasmodium falciparum Potency 11689.1 nM None
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
None Unchecked Activity nan None 10.1021/acs.jnatprod.1c00429
None Unchecked EC50 3545.0 nM 10.1021/acs.jnatprod.1c00429
None Unchecked EC50 3595.0 nM 10.1021/acs.jnatprod.1c00429
None Unchecked IC50 4065.0 nM 10.1021/acs.jnatprod.1c00429
None Unchecked IC50 4300.0 nM None
None Unchecked IC50 4622.0 nM 10.1021/acs.jnatprod.1c00429
None Unchecked IC50 5484.0 nM 10.1021/acs.jnatprod.1c00429
None Unchecked IC50 6811.0 nM 10.1021/acs.jnatprod.1c00429
None Unchecked IC50 7493.0 nM None
None Unchecked IC50 12497.0 nM None
None Unchecked Potency 2511.9 nM None
None Unchecked Potency 2592.9 nM None
None Unchecked Potency 4466.8 nM None
None Unchecked Potency 10322.5 nM None
None Unchecked Potency 11220.2 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT011654 COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(O)c3CN1CC2.C[33S]>>COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(OC)c3CN1CC2 None
AKRT011655 COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(O)c3CN1CC2.C[SAH]>>COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(O)c3C[N+]1(C)CC2 enzymemap_26918
AKRT011656 COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(O)c3CN1CC2.C[SAH]>>COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(OC)c3CN1CC2 2.1.1.117-RXN
AKRT011657 COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(O)c3CN1CC2.C[SAH]>>COc1cc2c(cc1OC)[C@@H]1Cc3ccc(OC)c(O)c3CN1CC2 RXN-19238
AKRT011658 COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(O)c3CN1CC2>>C=O enzymemap_10824
AKRT011659 COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(O)c3CN1CC2>>COc1cc2c(cc1O)-c1cc3ccc(OC)c(O)c3c[n+]1CC2 RXN-10888
AKRT011660 COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(O)c3CN1CC2>>COc1cc2c(cc1O)[C@@H]1Cc3ccc4c(c3CN1CC2)OCO4 1.14.21.2-RXN
AKRT011661 COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(O)c3CN1CC2>>COc1ccc2c(c1O)CN1CCc3cc(O)c(O)cc3[C@@H]1C2 enzymemap_10824
AKRT011662 COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(O)c3CN1CC2>>COc1ccc2c(c1O)CN1CCc3cc4c(cc3[C@@H]1C2)OCO4 RXN-15538
AKRT011821 COc1ccc(C[C@H]2c3cc(O)c(OC)cc3CCN2C)cc1O>>COc1cc2c(cc1O)[C@@H]1Cc3ccc(OC)c(O)c3CN1CC2 RETICULINE-OXIDASE-RXN