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Homoharringtonine

AlkaPlorer ID: AK002931

Synonym: '(-)-Homoharringtonine'

IUPAC Name: 1-O-[(2S,3S,6R)-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.02,6.06,10.015,19]icosa-1(20),4,13,15(19)-tetraen-3-yl] 4-O-methyl (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate

Structure

SMILES: COC(=O)C[C@](O)(CCCC(C)(C)O)C(=O)O[C@@H]1C(OC)=C[C@]23CCCN2CCC2=CC4=C(C=C2[C@H]13)OCO4

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InChI: InChI=1S/C29H39NO9/c1-27(2,33)8-5-10-29(34,16-23(31)36-4)26(32)39-25-22(35-3)15-28-9-6-11-30(28)12-7-18-13-20-21(38-17-37-20)14-19(18)24(25)28/h13-15,24-25,33-34H,5-12,16-17H2,1-4H3/t24-,25-,28+,29-/m1/s1

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InChIKey: HYFHYPWGAURHIV-JFIAXGOJSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Casearia graveolens Casearia Salicaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 545.6290000000004

TPSA？: 123.99000000000002

MolLogP？: 2.5807

Number of H-Donors: 2

Number of H-Acceptors: 10

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Acinetobacter baumannii Acinetobacter baumannii Inhibition 6.01 % 10.6019/CHEMBL4513141
Agrobacterium tumefaciens Agrobacterium tumefaciens Inhibition -79.0 % 10.1021/np50024a005
Agrobacterium tumefaciens Agrobacterium tumefaciens Inhibition -72.0 % 10.1021/np50024a005
Agrobacterium tumefaciens Agrobacterium tumefaciens Inhibition -64.0 % 10.1021/np50024a005
Agrobacterium tumefaciens Agrobacterium tumefaciens Inhibition nan % 10.1021/np50024a005
Candida albicans Candida albicans Inhibition 3.16 % 10.6019/CHEMBL4513141
Cryptococcus neoformans Cryptococcus neoformans Inhibition 1.94 % 10.6019/CHEMBL4513141
Escherichia coli Escherichia coli Inhibition 7.87 % 10.6019/CHEMBL4513141
Homo sapiens 786-0 GI50 893.31 nM None
Homo sapiens A204 IC50 4.0 nM 10.1016/j.ejmech.2022.114731
Homo sapiens A498 GI50 39.54 nM None
Homo sapiens A549 Activity nan None 10.1016/j.bmcl.2019.06.049
Homo sapiens A549 GI50 67.76 nM None
Homo sapiens A549 IC50 30.0 nM 10.1016/j.bmcl.2008.08.050
Homo sapiens A549 IC50 31.6 nM 10.1021/acs.jnatprod.9b00515
Homo sapiens Acetylcholinesterase AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens ACHN GI50 616.6 nM None
Homo sapiens Adenosine A1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-1a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Androgen Receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens BJ EC50 4.88 nM None
Homo sapiens BT-549 GI50 3597.49 nM None
Homo sapiens Caco-2 CC50 1720.0 nM 10.21203/rs.3.rs-23951/v1
Homo sapiens CAKI-1 GI50 202.77 nM None
Homo sapiens CCRF-CEM GI50 21.53 nM None
Homo sapiens COLO 205 GI50 218.27 nM None
Homo sapiens Cyclooxygenase-1 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cyclooxygenase-1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens DLD-1 GI50 23.12 nM None
Homo sapiens DMS-114 GI50 4.699 nM None
Homo sapiens DMS-273 GI50 6.792 nM None
Homo sapiens Dopamine D1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens DU-145 GI50 741.31 nM None
Homo sapiens EKVX GI50 132.74 nM None
Homo sapiens Estrogen receptor alpha AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens HCC 2998 GI50 58.34 nM None
Homo sapiens HCT-116 GI50 110.41 nM None
Homo sapiens HCT-116 IC50 13.0 nM 10.1016/j.ejmech.2022.114731
Homo sapiens HCT-15 GI50 217.27 nM None
Homo sapiens HeLa IC50 400.0 nM 10.1021/acs.jnatprod.0c01354
Homo sapiens HeLa IC50 1700.0 nM 10.1021/acs.jnatprod.1c00888
Homo sapiens HeLa Inhibition 50.0 % 10.1021/acs.jmedchem.7b00315
Homo sapiens HepG2 IC50 34.5 nM 10.1021/acs.jnatprod.9b00515
Homo sapiens HepG2 IC50 relative 200.0 nM 10.6019/EOS300108
Homo sapiens HERG AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histone deacetylase 6 Inhibition -2.3 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 28.94 % 10.6019/CHEMBL4808148
Homo sapiens HL-60 GI50 32.51 nM None
Homo sapiens HL-60 IC50 13.0 nM 10.1016/j.ejmech.2022.114731
Homo sapiens HL-60 IC50 21.8 nM 10.1021/acs.jnatprod.1c00888
Homo sapiens HL-60 IC50 22.0 nM 10.1021/acs.jnatprod.7b00541
Homo sapiens HL-60 Ratio IC50 125.0 None 10.1039/C0MD00241K
Homo sapiens HOP-18 GI50 59.98 nM None
Homo sapiens HOP-62 GI50 59.7 nM None
Homo sapiens HOP-92 GI50 86.9 nM None
Homo sapiens Hs-578T GI50 1066.6 nM None
Homo sapiens HT-29 GI50 115.08 nM None
Homo sapiens Huh-7 IC50 40.0 nM 10.1016/j.ejmech.2022.114731
Homo sapiens IGROV-1 GI50 128.82 nM None
Homo sapiens K562 GI50 39.72 nM None
Homo sapiens K562 IC50 0.04389 ug.mL-1 10.1016/j.ejmech.2022.114442
Homo sapiens K562 IC50 14.0 nM 10.1016/j.ejmech.2022.114731
Homo sapiens KB ED50 3.9 ug ml-1 10.1021/np50022a010
Homo sapiens KB IC50 4.0 nM 10.1016/j.bmcl.2008.08.050
Homo sapiens KM12 GI50 142.23 nM None
Homo sapiens KM-20L2 GI50 19.19 nM None
Homo sapiens L02 IC50 64.0 nM 10.1016/j.ejmech.2022.114731
Homo sapiens LOX IMVI GI50 44.36 nM None
Homo sapiens M14 GI50 1205.04 nM None
Homo sapiens M19-MEL GI50 19.36 nM None
Homo sapiens Malme-3M GI50 56.75 nM None
Homo sapiens MCF7 GI50 14.96 nM None
Homo sapiens MCF7 IC50 0.87 nM 10.1021/acs.jmedchem.7b00315
Homo sapiens MDA-MB-231 GI50 1698.24 nM None
Homo sapiens MDA-MB-435 GI50 4456.56 nM None
Homo sapiens MDA-MB-453 IC50 21.0 nM 10.1016/j.ejmech.2022.114731
Homo sapiens MDA-N GI50 2415.46 nM None
Homo sapiens MOLT-4 GI50 12.33 nM None
Homo sapiens MOLT-4 IC50 7.0 nM 10.1016/j.ejmech.2022.114731
Homo sapiens Monoamine oxidase A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Mu opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens MV4-11 IC50 5.0 nM 10.1016/j.ejmech.2022.114731
Homo sapiens NCI/ADR-RES GI50 3872.58 nM None
Homo sapiens NCI-H1299 IC50 22.0 nM 10.1016/j.ejmech.2022.114731
Homo sapiens NCI-H1975 IC50 22.0 nM 10.1016/j.ejmech.2022.114731
Homo sapiens NCI-H226 GI50 89.95 nM None
Homo sapiens NCI-H23 GI50 52.84 nM None
Homo sapiens NCI-H322M GI50 909.91 nM None
Homo sapiens NCI-H460 GI50 13.0 nM None
Homo sapiens NCI-H522 GI50 39.63 nM None
Homo sapiens NCI-H716 IC50 65.0 nM 10.1016/j.ejmech.2022.114731
Homo sapiens Norepinephrine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens OCI-Ly3 IC50 5.0 nM 10.1016/j.ejmech.2022.114731
Homo sapiens OVCAR-3 GI50 212.32 nM None
Homo sapiens OVCAR-4 GI50 341.98 nM None
Homo sapiens OVCAR-5 GI50 494.31 nM None
Homo sapiens OVCAR-8 GI50 146.22 nM None
Homo sapiens Panel NCI-60 (60 carcinoma cell lines) GI50 4.4 nM 10.1021/jm049838d
Homo sapiens PC-3 GI50 3013.01 nM None
Homo sapiens Phosphodiesterase 3A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 4A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Progesterone receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens RPMI-8226 GI50 38.82 nM None
Homo sapiens RXF 393 GI50 106.66 nM None
Homo sapiens Serotonin 1a (5-HT1a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2b (5-HT2b) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens SF-268 GI50 148.59 nM None
Homo sapiens SF-295 GI50 151.71 nM None
Homo sapiens SF-539 GI50 55.98 nM None
Homo sapiens SK-MEL-2 GI50 258.82 nM None
Homo sapiens SK-MEL-28 GI50 111.43 nM None
Homo sapiens SK-MEL-5 GI50 117.49 nM None
Homo sapiens SK-OV-3 GI50 122.18 nM None
Homo sapiens SN12C GI50 120.78 nM None
Homo sapiens SN12K1 GI50 11.46 nM None
Homo sapiens SNB-19 GI50 70.63 nM None
Homo sapiens SNB-75 GI50 102.09 nM None
Homo sapiens SNB-78 GI50 68.23 nM None
Homo sapiens SR GI50 32.66 nM None
Homo sapiens SW-620 GI50 68.23 nM None
Homo sapiens T47D GI50 382.82 nM None
Homo sapiens Thrombin AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Thromboxane A2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens TK-10 GI50 3741.11 nM None
Homo sapiens U-251 GI50 57.15 nM None
Homo sapiens U-937 IC50 12.0 nM 10.1016/j.ejmech.2022.114731
Homo sapiens UACC-257 GI50 179.47 nM None
Homo sapiens UACC-62 GI50 112.98 nM None
Homo sapiens UO-31 GI50 545.76 nM None
Homo sapiens XF498 GI50 9.141 nM None
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 reverse transcriptase IC50 200.0 ug.mL-1 10.1021/np50073a012
Klebsiella pneumoniae Klebsiella pneumoniae Inhibition 9.21 % 10.6019/CHEMBL4513141
Mus musculus 4T1 IC50 60.0 nM 10.1016/j.ejmech.2022.114731
Mus musculus BaF3 IC50 81.0 nM 10.1016/j.ejmech.2022.114731
Mus musculus L1210 T/C 123.0 % 10.1021/np8006217
Mus musculus P388 GI50 3.882 nM None
Mus musculus P388 IC50 0.017 ug.mL-1 10.1016/0960-894X(96)00302-2
Mus musculus P388 T/C 238.0 % 10.1021/np50024a005
Mus musculus P388 T/C 244.0 % 10.1021/np8006217
Mus musculus P388/ADR GI50 246.6 nM None
Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition 11.81 % 10.6019/CHEMBL4513141
Rattus norvegicus GABA receptor alpha-1 subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 6.843 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 20.63 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 EC50 60.0 nM 10.1021/acs.jmedchem.0c01746
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 EC50 2100.0 nM 10.1016/j.bmc.2020.115757
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.04224 None 10.1101/2020.04.21.054387
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 4710.0 nM 10.21203/rs.3.rs-23951/v1
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
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.67 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.37 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 102.02 % 10.21203/rs.3.rs-23951/v1
Staphylococcus aureus Staphylococcus aureus Inhibition 10.39 % 10.6019/CHEMBL4513141
None ADMET Selectivity index 0.0 None 10.21203/rs.3.rs-23951/v1
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx900326k
None NON-PROTEIN TARGET Hepatotoxicity (acute) 0.0 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (animal toxicity known) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (benign tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (granulomatous hepatitis) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (mechanism) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 3.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 15.0 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (time to onset) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET IC50 20.0 nM 10.1039/C0MD00241K
None NON-PROTEIN TARGET IC50 510.0 nM 10.1016/j.bmcl.2008.08.050
None Unchecked Activity nan None 10.1016/j.bmcl.2019.06.049
None Unchecked EC50 100.0 nM None
None Unchecked Hepatotoxicity (acute) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (association with vascular disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (choleostasis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (chronic liver disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cirrhosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (comment) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cytolytic) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (malignant tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (severe hepatitis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (steatosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (successful reintroduction) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked IC50 18.28 nM 10.1016/j.bmcl.2019.06.049
None Unchecked IC50 1000000.0 nM 10.1021/jm00007a003
None Unchecked IC50 3000000.0 nM 10.1021/jm00007a003
None Unchecked Inhibition nan % 10.1016/j.bmcl.2019.06.049
None Unchecked Kd 16970.0 nM 10.1016/j.bmcl.2019.06.049

Metabolism Information