Molecule

Largazole

AlkaPlorer ID: AK067734

Synonym: None

IUPAC Name: S-[(E)-4-[(5R,8S,11S)-5-methyl-6,9,13-trioxo-8-propan-2-yl-10-oxa-3,17-dithia-7,14,19,20-tetrazatricyclo[14.2.1.12,5]icosa-1(18),2(20),16(19)-trien-11-yl]but-3-enyl] octanethioate

Structure

SMILES: CCCCCCCC(=O)SCC/C=C/[C@@H]1CC(O)=NCC2=NC(=CS2)C2=N[C@@](C)(CS2)C(O)=N[C@@H](C(C)C)C(=O)O1

InChI: InChI=1S/C29H42N4O5S3/c1-5-6-7-8-9-13-24(35)39-14-11-10-12-20-15-22(34)30-16-23-31-21(17-40-23)26-33-29(4,18-41-26)28(37)32-25(19(2)3)27(36)38-20/h10,12,17,19-20,25H,5-9,11,13-16,18H2,1-4H3,(H,30,34)(H,32,37)/b12-10+/t20-,25+,29+/m1/s1

InChIKey: AXESYCSCGBQJBL-SZPBEECKSA-N

Reference

Coibamide A, a Potent Antiproliferative Cyclic Depsipeptide from the Panamanian Marine Cyanobacterium <i>Leptolyngbya</i> sp.

PubChem CID: 24757913

LOTUS: LTS0056793

NPASS: NPC469801

{

NPAtlas: NPA018921

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Caldora penicillata	Caldora	None	Oscillatoriales	Cyanophyceae	Cyanobacteriota	None	Bacteria
Hyrtios reticulatus	Hyrtios	Thorectidae	Dictyoceratida	Demospongiae	Porifera	Metazoa	Eukaryota
None	Symploca	Microcoleaceae	Oscillatoriales	Cyanophyceae	Cyanobacteriota	None	Bacteria

Properties Information

Molecule Weight: 622.8790000000001

TPSA？: 133.79999999999998

MolLogP？: 6.714900000000007

Number of H-Donors: 2

Number of H-Acceptors: 10

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Homo sapiens	A549	Activity	3.1	%	10.1021/ml400093y
Homo sapiens	A549	Activity	3.3	%	10.1021/ml400093y
Homo sapiens	A549	Activity	6.5	%	10.1021/ml400093y
Homo sapiens	A549	Activity	8.5	%	10.1021/ml400093y
Homo sapiens	A549	Activity	70.0	%	10.1021/ml400093y
Homo sapiens	A549	Activity	88.2	%	10.1021/ml400093y
Homo sapiens	A549	Activity	90.4	%	10.1021/ml400093y
Homo sapiens	A549	Activity	nan	None	10.1021/ml400093y
Homo sapiens	A549	GI	nan	None	10.1021/ml400093y
Homo sapiens	A549	GI50	1460.0	nM	10.1016/j.ejmech.2019.112016
Homo sapiens	A549	IC50	77.0	nM	10.1021/ml400093y
Homo sapiens	A549	IC50	460.0	nM	10.1016/j.ejmech.2019.111672
Homo sapiens	A549	Inhibition	nan	%	10.1021/ml400093y
Homo sapiens	Caco-2	EC50	14.45	nM	10.1021/acsmedchemlett.9b00643
Homo sapiens	Caco-2	EC50	758.58	nM	10.1021/acsmedchemlett.9b00643
Homo sapiens	Caco-2	EC50	10000000.0	nM	10.1021/acsmedchemlett.9b00643
Homo sapiens	DU-145	GI50	11.0	nM	10.1021/acs.jmedchem.5b01044
Homo sapiens	HCT-116	GI50	10.0	nM	10.1021/jm200432a
Homo sapiens	HCT-116	GI50	65.0	nM	10.1021/acs.jmedchem.6b01271
Homo sapiens	HCT-116	IC50	20.0	nM	10.1016/j.bmc.2017.03.071
Homo sapiens	HCT-116	IC50	44.0	nM	10.1016/j.ejmech.2019.111672
Homo sapiens	HCT-116	IC50	390.0	nM	10.1016/j.ejmech.2019.112016
Homo sapiens	HCT-116	Inhibition	nan	%	10.1021/ml500170r
Homo sapiens	HEK293	GI50	100000.0	nM	10.1016/j.ejmech.2019.112016
Homo sapiens	Histone deacetylase	INH	572.0	nM	10.1016/j.bmc.2011.02.024
Homo sapiens	Histone deacetylase	Inhibition	nan	%	10.1016/j.bmc.2011.02.024
Homo sapiens	Histone deacetylase	Inhibition	nan	%	10.1016/j.ejmech.2014.09.009
Homo sapiens	Histone deacetylase	Inhibition	nan	%	10.1021/acs.jmedchem.6b01271
Homo sapiens	Histone deacetylase	Inhibition	nan	%	10.1021/jm100244y
Homo sapiens	Histone deacetylase	Inhibition	nan	%	10.1021/ml500170r
Homo sapiens	Histone deacetylase 1	Activity	nan	None	10.1021/ml400093y
Homo sapiens	Histone deacetylase 1	IC50	10.09	nM	10.1016/j.bmc.2015.03.063
Homo sapiens	Histone deacetylase 1	IC50	11.4	nM	10.1016/j.bmc.2021.116510
Homo sapiens	Histone deacetylase 1	IC50	11.4	nM	10.1021/jm100244y
Homo sapiens	Histone deacetylase 1	IC50	13.7	nM	10.1021/ml400470s
Homo sapiens	Histone deacetylase 1	IC50	61.0	nM	10.1021/acs.jmedchem.6b01271
Homo sapiens	Histone deacetylase 1	IC50	69.8	nM	10.1021/acs.jmedchem.5b01044
Homo sapiens	Histone deacetylase 1	IC50	146.0	nM	10.1021/ml300371t
Homo sapiens	Histone deacetylase 1	IC50	228.0	nM	10.1016/j.ejmech.2019.111672
Homo sapiens	Histone deacetylase 1	IC50	230.0	nM	10.1016/j.bmcl.2013.06.012
Homo sapiens	Histone deacetylase 1	IC50	2330.0	nM	10.1021/acs.jmedchem.5b01632
Homo sapiens	Histone deacetylase 1	Inhibition	15.0	%	10.1016/j.ejmech.2014.09.009
Homo sapiens	Histone deacetylase 1	Inhibition	90.0	%	10.1016/j.ejmech.2014.09.009
Homo sapiens	Histone deacetylase 1	Inhibition	nan	%	10.1016/j.ejmech.2014.09.009
Homo sapiens	Histone deacetylase 1	Inhibition	nan	%	10.1016/j.ejmech.2019.111672
Homo sapiens	Histone deacetylase 1	Inhibition	nan	%	10.1021/jm100244y
Homo sapiens	Histone deacetylase 1	Inhibition	nan	%	10.1021/jm200432a
Homo sapiens	Histone deacetylase 1	Inhibition	nan	%	10.1021/ml400093y
Homo sapiens	Histone deacetylase 10	IC50	2210.0	nM	10.1021/acs.jmedchem.5b01044
Homo sapiens	Histone deacetylase 11	IC50	10000.0	nM	10.1021/acs.jmedchem.5b01044
Homo sapiens	Histone deacetylase 2	IC50	18.65	nM	10.1016/j.bmc.2015.03.063
Homo sapiens	Histone deacetylase 2	IC50	64.0	nM	10.1021/acs.jmedchem.6b01271
Homo sapiens	Histone deacetylase 2	IC50	900.0	nM	10.1016/j.bmcl.2013.06.012
Homo sapiens	Histone deacetylase 2	IC50	1010.0	nM	10.1021/acs.jmedchem.5b01044
Homo sapiens	Histone deacetylase 2	IC50	1520.0	nM	10.1016/j.ejmech.2019.111672
Homo sapiens	Histone deacetylase 2	IC50	1720.0	nM	10.1021/ml300371t
Homo sapiens	Histone deacetylase 2	Inhibition	nan	%	10.1016/j.ejmech.2019.111672
Homo sapiens	Histone deacetylase 3	IC50	9.09	nM	10.1016/j.bmc.2015.03.063
Homo sapiens	Histone deacetylase 3	IC50	50.0	nM	10.1021/acs.jmedchem.6b01271
Homo sapiens	Histone deacetylase 3	IC50	245.0	nM	10.1021/ml400470s
Homo sapiens	Histone deacetylase 3	IC50	604.0	nM	10.1021/ml300371t
Homo sapiens	Histone deacetylase 3	IC50	670.0	nM	10.1016/j.bmcl.2013.06.012
Homo sapiens	Histone deacetylase 3	IC50	859.0	nM	10.1021/acs.jmedchem.5b01044
Homo sapiens	Histone deacetylase 3	IC50	1360.0	nM	10.1021/acs.jmedchem.5b01632
Homo sapiens	Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	IC50	2002.0	nM	10.1016/j.ejmech.2019.111672
Homo sapiens	Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	Inhibition	nan	%	10.1016/j.ejmech.2019.111672
Homo sapiens	Histone deacetylase 4	IC50	3000.0	nM	10.1016/j.bmc.2021.116510
Homo sapiens	Histone deacetylase 4	IC50	3000.0	nM	10.1021/jm100244y
Homo sapiens	Histone deacetylase 4	IC50	10000.0	nM	10.1021/acs.jmedchem.5b01044
Homo sapiens	Histone deacetylase 4	Inhibition	nan	%	10.1021/jm100244y
Homo sapiens	Histone deacetylase 5	IC50	10000.0	nM	10.1021/acs.jmedchem.5b01044
Homo sapiens	Histone deacetylase 6	IC50	165.6	nM	10.1016/j.bmc.2015.03.063
Homo sapiens	Histone deacetylase 6	IC50	340.0	nM	10.1016/j.bmcl.2013.06.012
Homo sapiens	Histone deacetylase 6	IC50	1400.0	nM	10.1021/acs.jmedchem.6b01271
Homo sapiens	Histone deacetylase 6	IC50	1850.0	nM	10.1021/acs.jmedchem.5b01044
Homo sapiens	Histone deacetylase 6	IC50	5000.0	nM	10.1016/j.ejmech.2019.111672
Homo sapiens	Histone deacetylase 6	IC50	9290.0	nM	10.1021/acs.jmedchem.5b01632
Homo sapiens	Histone deacetylase 6	IC50	11500.0	nM	10.1021/ml400470s
Homo sapiens	Histone deacetylase 6	Inhibition	50.0	%	10.1016/j.ejmech.2014.09.009
Homo sapiens	Histone deacetylase 6	Inhibition	50.0	%	10.1021/jm200432a
Homo sapiens	Histone deacetylase 6	Inhibition	75.0	%	10.1016/j.ejmech.2014.09.009
Homo sapiens	Histone deacetylase 6	Inhibition	nan	%	10.1016/j.ejmech.2014.09.009
Homo sapiens	Histone deacetylase 6	Inhibition	nan	%	10.1016/j.ejmech.2019.111672
Homo sapiens	Histone deacetylase 6	Inhibition	nan	%	10.1021/jm200432a
Homo sapiens	Histone deacetylase 7	IC50	10000.0	nM	10.1021/acs.jmedchem.5b01044
Homo sapiens	Histone deacetylase 8	IC50	120.0	nM	10.1016/j.ejmech.2019.111672
Homo sapiens	Histone deacetylase 8	IC50	1068.0	nM	10.1016/j.bmc.2015.03.063
Homo sapiens	Histone deacetylase 8	IC50	10000.0	nM	10.1021/acs.jmedchem.5b01044
Homo sapiens	Histone deacetylase 8	IC50	30000.0	nM	10.1021/acs.jmedchem.5b01632
Homo sapiens	Histone deacetylase 8	Inhibition	nan	%	10.1016/j.ejmech.2019.111672
Homo sapiens	Histone deacetylase 9	IC50	8330.0	nM	10.1021/ml300371t
Homo sapiens	Histone deacetylase 9	IC50	10000.0	nM	10.1021/acs.jmedchem.5b01044
Homo sapiens	HT-29	Activity	55.0	%	10.1021/np500931q
Homo sapiens	HT-29	Activity	80.0	%	10.1021/np500931q
Homo sapiens	IMR-32	EC50	12.3	nM	10.1021/acsmedchemlett.9b00643
Homo sapiens	IMR-32	EC50	30.2	nM	10.1021/acsmedchemlett.9b00643
Homo sapiens	IMR-32	EC50	34.67	nM	10.1021/acsmedchemlett.9b00643
Homo sapiens	MCF7	GI	5.0	nM	10.1016/j.bmc.2011.02.024
Homo sapiens	MDA-MB-231	IC50	1.6	nM	10.1016/j.bmc.2017.03.071
Homo sapiens	MDA-MB-231	IC50	4750.0	nM	10.1016/j.ejmech.2019.111672
Homo sapiens	NB-4	Activity	5.0	%	10.1021/jm100244y
Homo sapiens	NB-4	Activity	nan	None	10.1021/jm100244y
Homo sapiens	NCI-H1975	IC50	83.0	nM	10.1021/ml400093y
Homo sapiens	NCI-H460	Activity	5.3	%	10.1021/ml400093y
Homo sapiens	NCI-H460	Activity	10.4	%	10.1021/ml400093y
Homo sapiens	NCI-H460	Activity	10.6	%	10.1021/ml400093y
Homo sapiens	NCI-H460	Activity	10.8	%	10.1021/ml400093y
Homo sapiens	NCI-H460	Activity	78.8	%	10.1021/ml400093y
Homo sapiens	NCI-H460	Activity	84.1	%	10.1021/ml400093y
Homo sapiens	NCI-H460	GI	nan	None	10.1021/ml400093y
Homo sapiens	NCI-H460	IC50	120.0	nM	10.1021/ml400093y
Homo sapiens	NCI-H460	Inhibition	nan	%	10.1021/ml400093y
Homo sapiens	Panel NCI-60 (60 carcinoma cell lines)	GI	60.0	%	10.1021/acs.jmedchem.6b01271
Homo sapiens	Retinoblastoma-associated protein	Activity	nan	None	10.1021/ml400093y
Homo sapiens	SK-OV-3	IC50	250.0	nM	10.1016/j.ejmech.2019.111672
Homo sapiens	SUMO-activating enzyme subunit 1	IC50	450000.0	nM	10.1021/jm301420b
Homo sapiens	Transcription factor E2F1	Activity	nan	None	10.1021/ml400093y
Homo sapiens	Transcription factor E2F1	Inhibition	nan	%	10.1021/ml400093y
Homo sapiens	Tubulin	Inhibition	nan	%	10.1021/jm100244y
Homo sapiens	U2OS	EC50	331.13	nM	10.1021/acsmedchemlett.9b00643
Homo sapiens	U2OS	EC50	371.54	nM	10.1021/acsmedchemlett.9b00643
Homo sapiens	U2OS	EC50	20417.38	nM	10.1021/acsmedchemlett.9b00643
Homo sapiens	U-937	GI50	16.8	nM	10.1021/acs.jmedchem.5b01044
Homo sapiens	Ubiquitin-like modifier-activating enzyme 1	IC50	29000.0	nM	10.1016/j.bmc.2012.05.044
Mus musculus	C2C12	Activity	nan	None	10.1021/ml1002794
Mus musculus	C2C12	FC	3.0	None	10.1021/ml1002794
Mus musculus	Liver	T1/2	0.08333	hr	10.1016/j.bmc.2011.02.024
Mus musculus	Mus musculus	Activity	nan	None	10.1021/ml1002794
Mus musculus	Runt-related transcription factor 2	FC	29.0	None	10.1021/ml1002794
Mus musculus	Serum	Drug metabolism	nan	None	10.1021/ml500170r
Schistosoma mansoni	Histone deacetylase 8	IC50	30000.0	nM	10.1016/j.bmc.2017.02.020
Schistosoma mansoni	Histone deacetylase 8	Inhibition	4.0	%	10.1016/j.bmc.2017.02.020
None	ADMET	Drug metabolism	nan	None	10.1021/ml500170r
None	ADMET	GI50	39.7	nM	10.1021/acs.jmedchem.5b01044
None	ADMET	GI50	82.5	nM	10.1021/acs.jmedchem.5b01044
None	ADMET	IC50	10000.0	nM	10.1021/ml400093y
None	ADMET	RatioGI50	0.28	None	10.1021/acs.jmedchem.5b01044
None	ADMET	Tmax	4.0	hr	10.1021/ml500170r
None	NON-PROTEIN TARGET	Emax	67.0	%	10.1021/acs.jnatprod.6b00203
None	NON-PROTEIN TARGET	Emax	70.0	%	10.1021/acs.jnatprod.6b00203
None	NON-PROTEIN TARGET	GI50	16.2	nM	10.1021/acs.jmedchem.5b01044
None	NON-PROTEIN TARGET	IC50	3.7	nM	10.1021/acs.jnatprod.6b00203
None	NON-PROTEIN TARGET	IC50	6.41	nM	10.1021/acs.jnatprod.6b00203
None	NON-PROTEIN TARGET	IC50	18.0	nM	10.1021/acs.jnatprod.6b00203
None	NON-PROTEIN TARGET	IC50	23.93	nM	10.1016/j.bmc.2015.03.063
None	NON-PROTEIN TARGET	IC50	24.0	nM	10.1016/j.bmc.2015.03.063
None	NON-PROTEIN TARGET	IC50	24.77	nM	10.1016/j.bmc.2015.03.063
None	NON-PROTEIN TARGET	IC50	25.0	nM	10.1016/j.bmc.2015.03.063
None	NON-PROTEIN TARGET	IC50	140.0	nM	10.1021/ml400093y
None	NON-PROTEIN TARGET	IC50	190.0	nM	10.1021/ml400093y
None	NON-PROTEIN TARGET	IC50	420.0	nM	10.1021/ml400093y
None	NON-PROTEIN TARGET	IC50	520.0	nM	10.1021/ml400093y
None	NON-PROTEIN TARGET	IC50	570.0	nM	10.1021/ml400093y
None	Unchecked	Activity	nan	None	10.1021/ml1002794
None	Unchecked	IC50	29000.0	nM	10.1021/jm301420b
None	Unchecked	Inhibition	nan	%	10.1016/j.bmc.2017.03.071
None	Unchecked	Inhibition	nan	%	10.1021/ml1002794
None	Unchecked	Ratio IC50	0.0	None	10.1016/j.ejmech.2016.12.032
None	Unchecked	Ratio IC50	0.02	None	10.1021/ml300371t
None	Unchecked	Ratio IC50	2.0	None	10.1016/j.ejmech.2016.12.032
None	Unchecked	Ratio IC50	3.0	None	10.1016/j.ejmech.2016.12.032
None	Unchecked	Ratio IC50	4.0	None	10.1016/j.ejmech.2016.12.032
None	Unchecked	Ratio IC50	7.0	None	10.1016/j.ejmech.2016.12.032
None	Unchecked	Ratio IC50	13.0	None	10.1016/j.ejmech.2016.12.032
None	Unchecked	Ratio IC50	22.0	None	10.1016/j.ejmech.2016.12.032
None	Unchecked	Ratio IC50	22.0	None	10.1021/acs.jmedchem.6b01271
None	Unchecked	Ratio IC50	nan	None	10.1016/j.ejmech.2019.111672