Molecule

Apicidin

AlkaPlorer ID: AK030364

Synonym: None

IUPAC Name: (3S,6S,9S,12R)-3-[(2S)-butan-2-yl]-6-[(1-methoxyindol-3-yl)methyl]-9-(6-oxooctyl)-1,4,7,10-tetrazabicyclo[10.4.0]hexadecane-2,5,8,11-tetrone

Structure

SMILES: CCC(=O)CCCCC[C@@H]1N=C(O)[C@H]2CCCCN2C(=O)[C@H]([C@@H](C)CC)N=C(O)[C@H](CC2=CN(OC)C3=CC=CC=C23)N=C1O

InChI: InChI=1S/C34H49N5O6/c1-5-22(3)30-34(44)38-19-13-12-18-29(38)33(43)35-26(16-9-7-8-14-24(40)6-2)31(41)36-27(32(42)37-30)20-23-21-39(45-4)28-17-11-10-15-25(23)28/h10-11,15,17,21-22,26-27,29-30H,5-9,12-14,16,18-20H2,1-4H3,(H,35,43)(H,36,41)(H,37,42)/t22-,26-,27-,29+,30-/m0/s1

InChIKey: JWOGUUIOCYMBPV-GMFLJSBRSA-N

Reference

Apicidins: Novel cyclic tetrapeptides as coccidiostats and antimalarial agents from Fusarium pallidoroseum

PubChem CID: 6918328

CAS: 183506-66-3

LOTUS: LTS0023988

SuperNatural Ⅲ: SN0177211-06

NPASS: NPC117244

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Humicola fuscoatra	Humicola	Chaetomiaceae	Sordariales	Sordariomycetes	Ascomycota	Fungi	Eukaryota
Fusarium fujikuroi	Fusarium	Nectriaceae	Hypocreales	Sordariomycetes	Ascomycota	Fungi	Eukaryota

Properties Information

Molecule Weight: 623.7950000000003

TPSA？: 149.31

MolLogP？: 5.587900000000005

Number of H-Donors: 3

Number of H-Acceptors: 7

RingCount: 4

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Alcaligenes sp. (strain DSM 11172) (Bordetella sp. (strain FB188))	Histone deacetylase-like amidohydrolase	Ki	9200.0	nM	10.1016/j.bmcl.2009.04.102
Chlorocebus sabaeus	Vero C1008	AUC cytotoxicity	179.8	None	10.1038/s41586-020-2286-9
Chlorocebus sabaeus	Vero C1008	pCC50	11.15	None	10.1038/s41586-020-2286-9
Cryptosporidium parvum	Histone deacetylase	IC50	0.008	ug.mL-1	10.1021/jm0001976
Cryptosporidium parvum	Histone deacetylase	IC50	1.0	nM	10.1016/s0960-894x(00)00605-3
Cryptosporidium parvum	Histone deacetylase	IC50	1.0	nM	10.1021/jm0001976
Cryptosporidium parvum	Histone deacetylase	IC50	1.0	nM	10.1021/jm0303094
Cryptosporidium parvum	Histone deacetylase	Ki	8.0	nM	10.1016/s0960-894x(00)00605-3
Eimeria tenella	Eimeria tenella	MIC	0.094	ug.mL-1	10.1016/s0960-894x(00)00605-3
Homo sapiens	BXPC-3	GI	98.0	%	10.1016/j.bmcl.2008.03.047
Homo sapiens	Coagulation factor III	IC50	150.0	nM	10.1074/jbc.m703586200
Homo sapiens	Coagulation factor III	IC50	200.0	nM	10.1074/jbc.m703586200
Homo sapiens	Coagulation factor III	Inhibition	80.0	%	10.1074/jbc.m703586200
Homo sapiens	Coagulation factor III	Inhibition	85.0	%	10.1074/jbc.m703586200
Homo sapiens	HCT-116	GI50	1000.0	nM	10.1021/ml300162r
Homo sapiens	HEK293	GI50	11000.0	nM	10.1021/ml300081u
Homo sapiens	HeLa	AP50	78.0	ng ml-1	10.1021/jm0001976
Homo sapiens	HeLa	GI50	1400.0	nM	10.1021/ml300081u
Homo sapiens	HeLa	GI50	2000.0	nM	10.1021/ml300162r
Homo sapiens	HeLa	GI50	3000.0	nM	10.1021/jm900850t
Homo sapiens	HeLa	IC50	290.0	nM	10.1016/j.bmcl.2006.09.002
Homo sapiens	HeLa	IC50	290.0	nM	10.1016/j.bmcl.2008.09.003
Homo sapiens	HeLa	IC50	290.0	nM	10.1016/j.bmcl.2009.04.011
Homo sapiens	HeLa	IC50	290.0	nM	10.1021/jm800079s
Homo sapiens	HFF	Activity	nan	None	10.1021/np0700523
Homo sapiens	Histone deacetylase	Activity	nan	None	10.1021/jm900850t
Homo sapiens	Histone deacetylase	IC50	0.004	ug.mL-1	10.1021/jm0001976
Homo sapiens	Histone deacetylase	IC50	1.0	nM	10.1016/s0960-894x(00)00605-3
Homo sapiens	Histone deacetylase	IC50	1.0	nM	10.1021/jm0001976
Homo sapiens	Histone deacetylase	IC50	1.0	nM	10.1021/jm0303094
Homo sapiens	Histone deacetylase	IC50	8.0	nM	10.1016/j.bmcl.2008.04.007
Homo sapiens	Histone deacetylase	IC50	22.0	nM	10.1021/jm900850t
Homo sapiens	Histone deacetylase	IC50	22.0	nM	10.1021/ml300162r
Homo sapiens	Histone deacetylase	IC50	43.0	nM	10.1021/jm900850t
Homo sapiens	Histone deacetylase 1	IC50	0.7	nM	10.1016/j.bmc.2010.03.080
Homo sapiens	Histone deacetylase 1	IC50	11.0	nM	10.1021/ml300162r
Homo sapiens	Histone deacetylase 1	IC50	13.0	nM	10.1016/j.bmcl.2008.03.047
Homo sapiens	Histone deacetylase 1	IC50	22.0	nM	10.1016/j.bmcl.2017.06.027
Homo sapiens	Histone deacetylase 1	IC50	22.0	nM	10.1021/jm900850t
Homo sapiens	Histone deacetylase 1	IC50	22.0	nM	10.1021/ml200136e
Homo sapiens	Histone deacetylase 1	IC50	23.0	nM	10.1016/j.bmcl.2008.02.025
Homo sapiens	Histone deacetylase 1	IC50	44.0	nM	10.1016/j.bmcl.2006.09.002
Homo sapiens	Histone deacetylase 1	IC50	44.0	nM	10.1016/j.bmcl.2008.09.003
Homo sapiens	Histone deacetylase 1	IC50	44.0	nM	10.1016/j.bmcl.2009.04.011
Homo sapiens	Histone deacetylase 1	IC50	44.0	nM	10.1016/j.bmcl.2009.04.102
Homo sapiens	Histone deacetylase 1	IC50	44.0	nM	10.1021/jm800079s
Homo sapiens	Histone deacetylase 1	Inhibition	0.3	%	10.1016/j.bmcl.2008.03.047
Homo sapiens	Histone deacetylase 1	Ki	0.04	nM	10.1038/nchembio.313
Homo sapiens	Histone deacetylase 2	IC50	1.0	nM	10.1016/j.bmc.2010.03.080
Homo sapiens	Histone deacetylase 2	IC50	34.0	nM	10.1021/ml300162r
Homo sapiens	Histone deacetylase 2	IC50	35.0	nM	10.1016/j.bmcl.2017.06.027
Homo sapiens	Histone deacetylase 2	IC50	35.0	nM	10.1021/ml300081u
Homo sapiens	Histone deacetylase 2	Ki	0.12	nM	10.1038/nchembio.313
Homo sapiens	Histone deacetylase 3	Activity	nan	None	10.1073/pnas.0706487104
Homo sapiens	Histone deacetylase 3	IC50	0.6	nM	10.1016/j.bmc.2010.03.080
Homo sapiens	Histone deacetylase 3	IC50	2.5	nM	10.1073/pnas.0706487104
Homo sapiens	Histone deacetylase 3	IC50	9.7	nM	10.1016/j.bmcl.2008.02.025
Homo sapiens	Histone deacetylase 3	IC50	29.0	nM	10.1016/j.bmcl.2017.06.027
Homo sapiens	Histone deacetylase 3	IC50	29.0	nM	10.1021/jm900850t
Homo sapiens	Histone deacetylase 3	Ki	0.26	nM	10.1038/nchembio.313
Homo sapiens	Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	IC50	13.0	nM	10.1021/ml300162r
Homo sapiens	Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	IC50	15.8	nM	10.1016/j.bmcl.2008.04.007
Homo sapiens	Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	IC50	29.0	nM	10.1021/ml200136e
Homo sapiens	Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	Ki	1.5	nM	10.1016/j.bmcl.2008.04.007
Homo sapiens	Histone deacetylase 4	Activity	12.0	%	10.1016/j.bmcl.2008.02.025
Homo sapiens	Histone deacetylase 4	Activity	nan	None	10.1073/pnas.0706487104
Homo sapiens	Histone deacetylase 4	IC50	1.0	nM	10.1073/pnas.0706487104
Homo sapiens	Histone deacetylase 4	IC50	1.2	nM	10.1073/pnas.0706487104
Homo sapiens	Histone deacetylase 4	IC50	2.4	nM	10.1073/pnas.0706487104
Homo sapiens	Histone deacetylase 4	IC50	3600.0	nM	10.1016/j.bmcl.2008.02.025
Homo sapiens	Histone deacetylase 4	IC50	8700.0	nM	10.1016/j.bmcl.2008.02.025
Homo sapiens	Histone deacetylase 5	Activity	nan	None	10.1073/pnas.0706487104
Homo sapiens	Histone deacetylase 6	Activity	nan	None	10.1021/jm900850t
Homo sapiens	Histone deacetylase 6	IC50	665.1	nM	10.1016/j.bmcl.2008.04.007
Homo sapiens	Histone deacetylase 6	IC50	4300.0	nM	10.1016/j.bmcl.2008.02.025
Homo sapiens	Histone deacetylase 6	IC50	9600.0	nM	10.1016/j.bmc.2010.03.080
Homo sapiens	Histone deacetylase 6	IC50	10000.0	nM	10.1016/j.bmcl.2017.06.027
Homo sapiens	Histone deacetylase 6	IC50	10000.0	nM	10.1021/jm900850t
Homo sapiens	Histone deacetylase 6	IC50	10000.0	nM	10.1021/ml200136e
Homo sapiens	Histone deacetylase 6	IC50	10000.0	nM	10.1021/ml300162r
Homo sapiens	Histone deacetylase 6	Ki	123.4	nM	10.1016/j.bmcl.2008.04.007
Homo sapiens	Histone deacetylase 7	Activity	nan	None	10.1021/ml200136e
Homo sapiens	Histone deacetylase 7	Activity	nan	None	10.1073/pnas.0706487104
Homo sapiens	Histone deacetylase 8	IC50	300.0	nM	10.1016/j.bmc.2010.03.080
Homo sapiens	Histone deacetylase 8	IC50	750.0	nM	10.1021/ml300162r
Homo sapiens	Histone deacetylase 8	IC50	755.0	nM	10.1021/ml200136e
Homo sapiens	Histone deacetylase 8	IC50	760.0	nM	10.1016/j.bmcl.2017.06.027
Homo sapiens	Histone deacetylase 8	IC50	760.0	nM	10.1021/jm900850t
Homo sapiens	Histone deacetylase 8	Ki	49.0	nM	10.1038/nchembio.313
Homo sapiens	HL-60	GI50	280.0	nM	10.1021/ml300081u
Homo sapiens	Jurkat	GI50	830.0	nM	10.1021/ml300081u
Homo sapiens	Jurkat	GI50	4000.0	nM	10.1021/jm900850t
Homo sapiens	K562	GI50	900.0	nM	10.1021/jm900850t
Homo sapiens	K562	GI50	1500.0	nM	10.1021/ml300162r
Homo sapiens	MCF7	GI50	5000.0	nM	10.1021/ml300162r
Homo sapiens	MCF7	GI50	6800.0	nM	10.1021/ml300081u
Homo sapiens	MCF7	GI50	7000.0	nM	10.1021/jm900850t
Homo sapiens	Vitamin D receptor	Potency	31622.8	nM	None
Human immunodeficiency virus 1	Human immunodeficiency virus 1	Activity	100.0	%	10.1021/np400889x
Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	300.0	nM	10.1021/np400889x
Leishmania donovani	Leishmania donovani	ED50	nan	None	10.1016/s0960-894x(01)00049-x
Plasmodium falciparum	Histone deacetylase	IC50	1.0	nM	10.1021/jm801654y
Plasmodium falciparum	Plasmodium falciparum	Activity	nan	None	10.1128/aac.00439-08
Plasmodium falciparum	Plasmodium falciparum	ED50	0.22	mg ml-1	10.1016/s0960-894x(01)00049-x
Plasmodium falciparum	Plasmodium falciparum	IC50	0.058	ug.mL-1	10.1016/s0960-894x(00)00605-3
Plasmodium falciparum	Plasmodium falciparum	IC50	0.058	ug.mL-1	10.1021/jm0303094
Plasmodium falciparum	Plasmodium falciparum	IC50	33.0	nM	10.1021/jm801654y
Plasmodium falciparum	Plasmodium falciparum	IC50	200.0	nM	10.1021/acs.jnatprod.2c00719
Plasmodium falciparum	Plasmodium falciparum	IC50	200.0	nM	10.1021/np4006053
Plasmodium falciparum	Plasmodium falciparum	MIC	0.125	ug.mL-1	10.1128/aac.00439-08
Plasmodium falciparum	Plasmodium falciparum	MIC	190.0	nM	10.1021/acs.jnatprod.0c01370
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Activity	nan	None	10.1038/s41586-020-2286-9
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	AUC	379.9	None	10.1038/s41586-020-2286-9
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	IC50	999684595.59	nM	10.1038/s41586-020-2286-9
Toxoplasma gondii	Toxoplasma gondii	IC50	13.0	nM	10.1021/acs.jmedchem.6b01595
Trypanosoma brucei	Trypanosoma brucei	ED50	1.9	mg ml-1	10.1016/s0960-894x(01)00049-x
Trypanosoma cruzi	Trypanosoma cruzi	ED50	nan	None	10.1016/s0960-894x(01)00049-x
None	ADMET	AUC Ratio	0.4733	None	10.1038/s41586-020-2286-9
None	ADMET	ED50	0.2	mg ml-1	10.1016/s0960-894x(01)00049-x
None	Molecular identity unknown	Activity	nan	None	10.1016/j.bmcl.2011.07.053
None	Molecular identity unknown	Activity	nan	None	10.1021/ml200136e
None	NON-PROTEIN TARGET	AP50	89.0	ng ml-1	10.1016/s0960-894x(00)00605-3
None	NON-PROTEIN TARGET	ED50	0.28	uM	10.1021/np0700523
None	NON-PROTEIN TARGET	GI	nan	None	10.1021/np500387h
None	NON-PROTEIN TARGET	GI50	800.0	nM	10.1021/jm501399d
None	NON-PROTEIN TARGET	GI50	800.0	nM	10.1039/C4MD00252K
None	NON-PROTEIN TARGET	GI50	2500.0	nM	10.1021/jm900850t
None	NON-PROTEIN TARGET	GI50	2700.0	nM	10.1021/ml300162r
None	NON-PROTEIN TARGET	IC50	0.057	ug.mL-1	10.1021/jm0001976
None	NON-PROTEIN TARGET	Inhibition	nan	%	10.1039/C4MD00252K
None	Unchecked	FC	1.0	None	10.1016/j.bmcl.2017.06.027
None	Unchecked	FC	100.0	None	10.1021/ml200136e
None	Unchecked	FC	nan	None	10.1016/j.bmcl.2017.06.027
None	Unchecked	IC50	0.7	nM	10.1021/acs.jnatprod.2c00719
None	Unchecked	IC50	4.0	nM	10.1016/j.bmcl.2009.03.085
None	Unchecked	IC50	670.0	nM	10.1016/j.bmcl.2009.04.102
None	Unchecked	Ki	4.0	nM	10.1016/s0960-894x(00)00605-3
None	Unchecked	Potency	11220.2	nM	None