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Leinamycin

AlkaPlorer ID: AK018362

Synonym: 'Antibiotic DC 107', '(+)-Leinamycin', 'Not named', 'Leinamycin', 'DC 107'

IUPAC Name: (2R,4'R,6R,9E,11R,13E,15Z)-4',11-dihydroxy-2,4',9-trimethyl-1'-oxospiro[19-thia-3,20-diazabicyclo[15.2.1]icosa-1(20),9,13,15,17-pentaene-6,5'-dithiolane]-3',4,12-trione

Structure

SMILES: C/C1=C\[C@@H](O)C(=O)/C=C/C=C\C2=CSC(=N2)[C@@H](C)NC(=O)C[C@@]2(CC1)S(=O)SC(=O)[C@]2(C)O

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InChI: InChI=1S/C22H26N2O6S3/c1-13-8-9-22(21(3,29)20(28)32-33(22)30)11-18(27)23-14(2)19-24-15(12-31-19)6-4-5-7-16(25)17(26)10-13/h4-7,10,12,14,17,26,29H,8-9,11H2,1-3H3,(H,23,27)/b6-4-,7-5+,13-10+/t14-,17-,21+,22-,33?/m1/s1

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InChIKey: ZHTRILQJTPJGNK-FYBAATNNSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Streptomyces sp. Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria

Properties Information

Molecule Weight: 510.65900000000033

TPSA？: 133.65999999999997

MolLogP？: 2.3768000000000007

Number of H-Donors: 3

Number of H-Acceptors: 9

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Cricetulus griseus CHO-AA8 IC50 0.01 ug.mL-1 10.1016/j.bmc.2012.05.033
Cricetulus griseus CHO-AA8 Ratio 3.0 None 10.1016/j.bmc.2012.05.033
Homo sapiens 786-0 GI50 3.908 nM None
Homo sapiens A-375 EC50 4.69 nM 10.1016/j.bmcl.2015.05.078
Homo sapiens A498 GI50 10.0 nM None
Homo sapiens A549 GI50 120.5 nM None
Homo sapiens ACHN GI50 2.239 nM None
Homo sapiens BT-549 GI50 1.514 nM None
Homo sapiens CAKI-1 GI50 1.327 nM None
Homo sapiens CCRF-CEM GI50 1.047 nM None
Homo sapiens COLO 205 GI50 14.89 nM None
Homo sapiens DLD-1 GI50 20.89 nM None
Homo sapiens DMS-114 GI50 35.32 nM None
Homo sapiens DMS-273 GI50 13.52 nM None
Homo sapiens DU-145 GI50 6.792 nM None
Homo sapiens EKVX GI50 260.62 nM None
Homo sapiens HCC 2998 GI50 184.5 nM None
Homo sapiens HCT-116 GI50 1.738 nM None
Homo sapiens HCT-15 GI50 13.4 nM None
Homo sapiens HeLa IC50 11.0 nM 10.1016/s0960-894x(98)00133-4
Homo sapiens HeLa IC50 11.0 nM 10.1021/jm9900366
Homo sapiens HeLa IC50 27.0 nM 10.1016/j.bmcl.2007.11.092
Homo sapiens HL-60 GI50 0.7516 nM None
Homo sapiens HOP-18 GI50 30.06 nM None
Homo sapiens HOP-62 GI50 130.32 nM None
Homo sapiens HOP-92 GI50 2.28 nM None
Homo sapiens Hs-578T GI50 33.73 nM None
Homo sapiens HT-29 GI50 39.99 nM None
Homo sapiens IGROV-1 GI50 199.53 nM None
Homo sapiens K562 GI50 4.56 nM None
Homo sapiens KM12 GI50 81.28 nM None
Homo sapiens KM-20L2 GI50 88.1 nM None
Homo sapiens LOX IMVI GI50 11.59 nM None
Homo sapiens LXFL 529 GI50 13.87 nM None
Homo sapiens M14 GI50 6.918 nM None
Homo sapiens M19-MEL GI50 34.43 nM None
Homo sapiens Malme-3M GI50 6.561 nM None
Homo sapiens MCF7 EC50 42.4 nM 10.1016/j.bmcl.2015.05.078
Homo sapiens MCF7 GI50 0.4989 nM None
Homo sapiens MDA-MB-231 EC50 8.99 nM 10.1016/j.bmcl.2015.05.078
Homo sapiens MDA-MB-231 GI50 32.06 nM None
Homo sapiens MDA-MB-435 GI50 18.66 nM None
Homo sapiens MDA-N GI50 10.05 nM None
Homo sapiens MOLT-4 GI50 4.864 nM None
Homo sapiens NCI/ADR-RES GI50 13.68 nM None
Homo sapiens NCI-H226 GI50 205.59 nM None
Homo sapiens NCI-H23 GI50 5.943 nM None
Homo sapiens NCI-H322M GI50 123.88 nM None
Homo sapiens NCI-H460 GI50 9.863 nM None
Homo sapiens NCI-H522 GI50 1.879 nM None
Homo sapiens OVCAR-3 GI50 11.25 nM None
Homo sapiens OVCAR-4 GI50 21.73 nM None
Homo sapiens OVCAR-5 GI50 103.99 nM None
Homo sapiens OVCAR-8 GI50 17.42 nM None
Homo sapiens PC-3 GI50 12.79 nM None
Homo sapiens Raji EC50 6.29 nM 10.1016/j.bmcl.2015.05.078
Homo sapiens RPMI-8226 GI50 4.446 nM None
Homo sapiens RXF 393 GI50 12.68 nM None
Homo sapiens RXF 631 GI50 108.14 nM None
Homo sapiens SF-268 GI50 27.16 nM None
Homo sapiens SF-295 GI50 44.57 nM None
Homo sapiens SF-539 GI50 9.683 nM None
Homo sapiens SK-MEL-2 GI50 6.012 nM None
Homo sapiens SK-MEL-28 GI50 21.43 nM None
Homo sapiens SK-MEL-5 GI50 6.73 nM None
Homo sapiens SK-OV-3 GI50 138.04 nM None
Homo sapiens SN12C GI50 20.28 nM None
Homo sapiens SNB-19 GI50 283.79 nM None
Homo sapiens SNB-75 GI50 25.18 nM None
Homo sapiens SNB-78 GI50 10.0 nM None
Homo sapiens SR GI50 3.273 nM None
Homo sapiens SW-620 GI50 2.037 nM None
Homo sapiens T47D EC50 15.2 nM 10.1016/j.bmcl.2015.05.078
Homo sapiens T47D GI50 1.019 nM None
Homo sapiens TK-10 GI50 26.55 nM None
Homo sapiens U-251 GI50 45.39 nM None
Homo sapiens UACC-257 GI50 29.79 nM None
Homo sapiens UACC-62 GI50 12.42 nM None
Homo sapiens UO-31 GI50 30.76 nM None
Homo sapiens XF498 GI50 17.58 nM None
Mus musculus Mus musculus OD 2.0 mg kg-1 10.1021/jm9900366
Mus musculus Mus musculus T/C 0.49 None 10.1021/jm9900366
Mus musculus P388 ILSmax 57.0 % 10.1016/s0960-894x(98)00133-4
Mus musculus P388 Optimal dose 0.38 mg kg-1 10.1016/s0960-894x(98)00133-4
None ADMET T1/2 6.0 hr 10.1021/jm9900366
None NON-PROTEIN TARGET Activity nan None 10.1016/j.bmc.2012.05.033
None NON-PROTEIN TARGET EC50 52.3 nM 10.1016/j.bmcl.2015.05.078
None NON-PROTEIN TARGET IC50 0.002 ug.mL-1 10.1016/j.bmc.2012.05.033
None NON-PROTEIN TARGET IC50 0.003 ug.mL-1 10.1016/j.bmc.2012.05.033
None NON-PROTEIN TARGET IC50 0.015 ug.mL-1 10.1016/j.bmc.2012.05.033
None NON-PROTEIN TARGET IC50 0.04 ug.mL-1 10.1016/j.bmc.2012.05.033
None No relevant target T1/2 0.1733 hr 10.1016/j.bmcl.2012.04.003
None No relevant target T1/2 8.0 hr 10.1016/j.bmcl.2012.04.003
None No relevant target T1/2 16.1 hr 10.1016/j.bmcl.2012.04.003
None No relevant target T1/2 27.0 hr 10.1016/j.bmcl.2012.04.003
None Nucleic Acid Activity nan None 10.1016/j.bmc.2012.05.033

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT001439 C/C1=C\[C@@H](O)C(=O)/C=C/C=C\c2csc(n2)[C@@H](C)NC(=O)C[C@]2(CC1)[C@@H](C)C(=O)SS2=O>>C/C1=C\[C@@H](O)C(=O)/C=C/C=C\c2csc(n2)[C@@H](C)NC(=O)C[C@@]2(CC1)S(=O)SC(=O)[C@]2(C)O RXN-22918