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Disermolide

AlkaPlorer ID: AK013318

Synonym: None

IUPAC Name: [(3Z,5S,6S,7S,8R,9S,11Z,13S,14S,15S,16Z,18S)-8,14,18-trihydroxy-19-[(2S,3R,4S,5R)-4-hydroxy-3,5-dimethyl-6-oxooxan-2-yl]-5,7,9,11,13,15-hexamethylnonadeca-1,3,11,16-tetraen-6-yl] carbamate

Structure

SMILES: C=C/C=C\[C@H](C)[C@H](OC(=N)O)[C@@H](C)[C@H](O)[C@@H](C)C/C(C)=C\[C@H](C)[C@@H](O)[C@@H](C)/C=C\[C@@H](O)C[C@@H]1OC(=O)[C@H](C)[C@@H](O)[C@H]1C

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InChI: InChI=1S/C33H55NO8/c1-10-11-12-20(4)31(42-33(34)40)24(8)29(37)22(6)16-18(2)15-21(5)28(36)19(3)13-14-26(35)17-27-23(7)30(38)25(9)32(39)41-27/h10-15,19-31,35-38H,1,16-17H2,2-9H3,(H2,34,40)/b12-11-,14-13-,18-15-/t19-,20-,21-,22-,23-,24-,25+,26+,27-,28-,29+,30-,31-/m0/s1

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InChIKey: AADVCYNFEREWOS-OBRABYBLSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Discodermia sp. Discodermia Theonellidae Tetractinellida Demospongiae Porifera Metazoa Eukaryota

Properties Information

Molecule Weight: 593.8020000000002

TPSA？: 160.53

MolLogP？: 4.710970000000005

Number of H-Donors: 6

Number of H-Acceptors: 8

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Chlorocebus sabaeus Vero IC50 30000.0 nM 10.1021/np030493w
Homo sapiens 1A9 GI50 1.7 nM 10.1021/jm061385k
Homo sapiens 1A9/ptx-10 GI50 6.2 nM 10.1021/jm061385k
Homo sapiens 1A9/ptx-22 GI50 7.0 nM 10.1021/jm061385k
Homo sapiens 2008 GI50 1.5 nM 10.1021/jm0204136
Homo sapiens 2008 GI50 2.7 nM 10.1021/jm051030l
Homo sapiens A2780 Concentration 0.51 uM 10.1016/j.bmcl.2005.03.018
Homo sapiens A549 Activity 14.0 % 10.1021/jm0204136
Homo sapiens A549 Activity nan None 10.1021/acs.jnatprod.8b00111
Homo sapiens A549 GI50 22.0 nM 10.1016/j.bmcl.2005.12.066
Homo sapiens A549 GI50 30.0 nM 10.1016/j.bmcl.2005.12.066
Homo sapiens A549 IC50 1.8 nM 10.1016/j.bmc.2020.115792
Homo sapiens A549 IC50 9.34 nM 10.1021/jm200692n
Homo sapiens A549 IC50 13.5 nM 10.1021/np020219m
Homo sapiens A549 IC50 13.5 nM 10.1021/np0203234
Homo sapiens A549 IC50 15.0 nM 10.1021/np030493w
Homo sapiens A549 IC50 22.0 nM 10.1016/j.bmcl.2005.05.068
Homo sapiens ASPC1 IC50 98.0 nM 10.1016/j.bmcl.2007.02.031
Homo sapiens ASPC1 IC50 98.0 nM 10.1016/j.bmcl.2008.09.109
Homo sapiens ASPC1 IC50 98.0 nM 10.1021/np070547s
Homo sapiens BT-20 Activity nan None 10.1021/acs.jnatprod.8b00111
Homo sapiens BT-549 Activity nan None 10.1021/acs.jnatprod.8b00111
Homo sapiens CCRF-CEM GI50 16.0 nM 10.1016/j.bmcl.2005.12.066
Homo sapiens CCRF-CEM GI50 52.0 nM 10.1016/j.bmcl.2005.12.066
Homo sapiens CCRF-CEM GI50 92.0 nM 10.1016/j.bmcl.2005.12.066
Homo sapiens CCRF-CEM GI50 158.0 nM 10.1016/j.bmcl.2005.12.066
Homo sapiens DLD-1 IC50 29.0 nM 10.1016/j.bmcl.2007.02.031
Homo sapiens DLD-1 IC50 29.0 nM 10.1016/j.bmcl.2008.09.109
Homo sapiens DLD-1 IC50 29.0 nM 10.1021/np070547s
Homo sapiens HCC1143 Activity nan None 10.1021/acs.jnatprod.8b00111
Homo sapiens HeLa Activity 65.0 None 10.1021/jm061385k
Homo sapiens HEY Activity 10.0 % 10.1021/acs.jnatprod.8b00111
Homo sapiens HEY Activity nan None 10.1021/acs.jnatprod.8b00111
Homo sapiens Hs-578T Activity 15.0 % 10.1021/acs.jnatprod.8b00111
Homo sapiens Hs-578T Activity nan None 10.1021/acs.jnatprod.8b00111
Homo sapiens HT-29 GI50 28.0 nM 10.1021/jm051030l
Homo sapiens Liver microsomes Stability nan % 10.1021/np900245k
Homo sapiens MCF7 Activity nan None 10.1021/acs.jnatprod.8b00111
Homo sapiens MCF7 GI50 28.0 nM 10.1016/j.bmcl.2005.12.066
Homo sapiens MCF7 IC50 2.4 nM 10.1021/np030493w
Homo sapiens MCF7 IC50 7.98 nM 10.1021/jm200692n
Homo sapiens MCF7 IC50 28.0 nM 10.1016/j.bmcl.2005.05.068
Homo sapiens MDA-MB-157 Activity nan None 10.1021/acs.jnatprod.8b00111
Homo sapiens MDA-MB-231 GI50 40.0 nM 10.1021/jm051030l
Homo sapiens MDA-MB-468 Activity nan None 10.1021/acs.jnatprod.8b00111
Homo sapiens NCI/ADR-RES GI50 240.0 nM 10.1016/j.bmcl.2005.12.066
Homo sapiens NCI/ADR-RES IC50 160.0 nM 10.1016/j.bmcl.2008.09.109
Homo sapiens PANC-1 IC50 49.0 nM 10.1021/np030493w
Homo sapiens PANC-1 IC50 59.0 nM 10.1016/j.bmcl.2007.02.031
Homo sapiens PANC-1 IC50 59.0 nM 10.1016/j.bmcl.2008.09.109
Homo sapiens PANC-1 IC50 59.0 nM 10.1021/np070547s
Homo sapiens PC-3 GI50 3.0 nM 10.1021/jm0204136
Homo sapiens PC-3 GI50 52.0 nM 10.1021/jm051030l
Homo sapiens SK-OV-3 IC50 6.1 nM 10.1016/j.bmc.2020.115792
Homo sapiens SK-OV-3 IC50 21.0 nM 10.1016/j.bmcl.2005.05.068
Mus musculus Brain AUC 66.51 ng.hr.mL-1 10.1021/ml400233e
Mus musculus L1210 GI50 9.2 nM 10.1021/jm051030l
Mus musculus P388 IC50 0.5 ug.mL-1 10.1016/j.bmc.2020.115792
Mus musculus P388 IC50 33.0 nM 10.1021/np030493w
Mus musculus P388 IC50 35.0 nM 10.1021/np000423e
Mus musculus P388 IC50 35.0 nM 10.1021/np020219m
Mus musculus P388 IC50 35.0 nM 10.1021/np0203234
Mus musculus P388 IC50 35.0 nM 10.1021/np070547s
Mus musculus Plasma AUC 260.68 ng.hr.mL-1 10.1021/ml400233e
None ADMET IC50 10.0 nM 10.1016/j.bmcl.2005.03.018
None ADMET IC50 100.0 nM 10.1016/j.bmcl.2005.03.018
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx900326k
None NCI IC50 160.0 nM 10.1016/j.bmcl.2007.02.031
None NON-PROTEIN TARGET GI50 2.6 nM 10.1021/jm0204136
None NON-PROTEIN TARGET IC50 17.0 nM 10.1021/np030493w
None NON-PROTEIN TARGET IC50 160.0 nM 10.1021/np070547s
None Unchecked Activity 27.0 % 10.1038/nchembio853
None Unchecked Activity 31.0 % 10.1038/nchembio853
None Unchecked Activity 32.0 % 10.1021/jm0204136
None Unchecked Activity 59.3 % 10.1021/acs.jnatprod.8b00111
None Unchecked Activity 76.0 % 10.1021/jm061385k
None Unchecked Activity nan None 10.1021/jm200692n
None Unchecked Activity nan None 10.1021/ml400233e
None Unchecked FC 4.0 None 10.1016/j.ejmech.2017.06.047
None Unchecked IC50 580.0 nM 10.1016/j.ejmech.2017.06.047
None Unchecked Inhibition 148.0 % 10.1021/jm061385k
None Unchecked Kd 0.18 nM 10.1038/nchembio853

Metabolism Information