Molecule

Fumitremorgin

AlkaPlorer ID: AK001550

Synonym: None

IUPAC Name: (1S,12S,15S)-7-methoxy-12-(2-methylprop-1-enyl)-10,13,19-triazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-3(11),4(9),5,7-tetraene-14,20-dione

Structure

SMILES: COC1=CC=C2C3=C(NC2=C1)[C@H](C=C(C)C)N1C(=O)[C@@H]2CCCN2C(=O)[C@@H]1C3

InChI: InChI=1S/C22H25N3O3/c1-12(2)9-18-20-15(14-7-6-13(28-3)10-16(14)23-20)11-19-21(26)24-8-4-5-17(24)22(27)25(18)19/h6-7,9-10,17-19,23H,4-5,8,11H2,1-3H3/t17-,18-,19-/m0/s1

InChIKey: DBEYVIGIPJSTOR-FHWLQOOXSA-N

Reference

Metabolites from <i>Aspergillus fumigatus</i>, an Endophytic Fungus Associated with <i>Melia azedarach</i>, and Their Antifungal, Antifeedant, and Toxic Activities

PubChem CID: 403923

CAS: 118974-02-0

LOTUS: LTS0166430

NPASS: NPC305984

{

NPAtlas: NPA020440

data_source: manually

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Aspergillus fumigatus	Aspergillus	Aspergillaceae	Eurotiales	Eurotiomycetes	Ascomycota	Fungi	Eukaryota
None	Colon	Leiodidae	Coleoptera	Insecta	Arthropoda	Metazoa	Eukaryota

Properties Information

Molecule Weight: 379.4600000000002

TPSA？: 65.64

MolLogP？: 2.9417000000000018

Number of H-Donors: 1

Number of H-Acceptors: 3

RingCount: 5

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	0.14	%	10.6019/CHEMBL4296183
Alternaria alternata	Alternaria alternata	MIC	12.5	ug.mL-1	10.1021/jf300146n
Alternaria solani	Alternaria solani	MIC	25.0	ug.mL-1	10.1021/jf300146n
Artemia salina	Artemia salina	LC50	40.5	ug.mL-1	10.1021/jf300146n
Botrytis cinerea	Botrytis cinerea	MIC	12.5	ug.mL-1	10.1021/jf300146n
Candida albicans	Candida albicans	Inhibition	1.52	%	10.6019/CHEMBL4296183
Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	MIC	12.5	ug.mL-1	10.1021/jf300146n
Cryptococcus neoformans	Cryptococcus neoformans	Inhibition	-5.88	%	10.6019/CHEMBL4296183
Escherichia coli	Escherichia coli	Inhibition	5.9	%	10.6019/CHEMBL4296183
Fusarium graminearum	Fusarium graminearum	MIC	12.5	ug.mL-1	10.1021/jf300146n
Fusarium oxysporum f. sp. niveum	Fusarium oxysporum f. sp. niveum	MIC	25.0	ug.mL-1	10.1021/jf300146n
Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	MIC	50.0	ug.mL-1	10.1021/jf300146n
Fusarium solani	Fusarium solani	MIC	50.0	ug.mL-1	10.1021/jf300146n
Homo sapiens	786-0	GI50	47973.34	nM	None
Homo sapiens	A498	GI50	100000.0	nM	None
Homo sapiens	A549	GI50	100000.0	nM	None
Homo sapiens	ACHN	GI50	55975.76	nM	None
Homo sapiens	ATP-binding cassette sub-family G member 2	Activity	274.5	%	10.1016/j.bmc.2007.10.006
Homo sapiens	ATP-binding cassette sub-family G member 2	Activity	nan	None	10.1002/ijc.11484
Homo sapiens	ATP-binding cassette sub-family G member 2	Activity	nan	None	10.1038/nrd3028
Homo sapiens	ATP-binding cassette sub-family G member 2	Activity	nan	None	10.1124/mol.64.3.610
Homo sapiens	ATP-binding cassette sub-family G member 2	Activity	nan	None	10.1124/mol.65.5.1208
Homo sapiens	ATP-binding cassette sub-family G member 2	Activity	nan	None	None
Homo sapiens	ATP-binding cassette sub-family G member 2	EC50	1000.0	nM	10.1021/acs.jmedchem.9b00963
Homo sapiens	ATP-binding cassette sub-family G member 2	Fluorescence intensity	315.0	a.u.	10.1021/jm050705h
Homo sapiens	ATP-binding cassette sub-family G member 2	IC50	321.0	nM	10.1016/j.bmcl.2017.09.009
Homo sapiens	ATP-binding cassette sub-family G member 2	IC50	451.0	nM	10.1016/j.bmcl.2017.09.009
Homo sapiens	ATP-binding cassette sub-family G member 2	IC50	470.0	nM	10.1016/j.ejmech.2022.114346
Homo sapiens	ATP-binding cassette sub-family G member 2	IC50	612.0	nM	10.1016/j.bmcl.2017.09.009
Homo sapiens	ATP-binding cassette sub-family G member 2	IC50	730.0	nM	10.1016/j.ejmech.2015.12.010
Homo sapiens	ATP-binding cassette sub-family G member 2	IC50	731.0	nM	10.1021/acsmedchemlett.8b00289
Homo sapiens	ATP-binding cassette sub-family G member 2	IC50	731.0	nM	10.1021/ml4000832
Homo sapiens	ATP-binding cassette sub-family G member 2	IC50	800.0	nM	10.1021/np100797y
Homo sapiens	ATP-binding cassette sub-family G member 2	IC50	960.0	nM	10.1016/j.bmcl.2016.09.076
Homo sapiens	ATP-binding cassette sub-family G member 2	IC50	1483.0	nM	10.1016/j.ejmech.2020.112133
Homo sapiens	ATP-binding cassette sub-family G member 2	IC50	11000.0	nM	10.1021/jm8013822
Homo sapiens	ATP-binding cassette sub-family G member 2	Imax	100.0	%	10.1021/ml4000832
Homo sapiens	ATP-binding cassette sub-family G member 2	Inhibition	100.0	%	10.1021/jm8013822
Homo sapiens	ATP-binding cassette sub-family G member 2	Inhibition	nan	%	10.1016/j.bmcl.2016.11.013
Homo sapiens	ATP-binding cassette sub-family G member 2	Ki	1300.0	nM	10.1006/bbrc.2001.5130
Homo sapiens	ATP-binding cassette sub-family G member 2	Ratio	1.9	None	10.1016/j.bmc.2010.06.004
Homo sapiens	ATP-binding cassette sub-family G member 2	Ratio	6.0	None	10.1016/j.bmc.2010.06.004
Homo sapiens	ATP-binding cassette sub-family G member 2	Ratio IC50	0.83	None	10.1016/j.bmcl.2011.08.070
Homo sapiens	ATP-binding cassette sub-family G member 2	Ratio IC50	1.03	None	10.1016/j.bmcl.2011.08.070
Homo sapiens	BT-549	GI50	100000.0	nM	None
Homo sapiens	CAKI-1	GI50	100000.0	nM	None
Homo sapiens	Canalicular multispecific organic anion transporter 1	Activity	nan	None	10.1021/jm8013822
Homo sapiens	Canalicular multispecific organic anion transporter 1	Ratio	nan	None	10.1016/j.bmc.2010.06.004
Homo sapiens	CCRF-CEM	GI50	100000.0	nM	None
Homo sapiens	COLO 205	GI50	100000.0	nM	None
Homo sapiens	DU-145	GI50	100000.0	nM	None
Homo sapiens	EKVX	GI50	100000.0	nM	None
Homo sapiens	HCC 2998	GI50	37153.52	nM	None
Homo sapiens	HCT-116	Activity	60.0	%	10.1021/jm050705h
Homo sapiens	HCT-116	GI50	100000.0	nM	None
Homo sapiens	HCT-15	GI50	100000.0	nM	None
Homo sapiens	HL-60	GI50	100000.0	nM	None
Homo sapiens	HOP-62	GI50	46989.41	nM	None
Homo sapiens	HOP-92	GI50	38725.76	nM	None
Homo sapiens	Hs-578T	GI50	50933.09	nM	None
Homo sapiens	HT-29	GI50	100000.0	nM	None
Homo sapiens	IGROV-1	GI50	100000.0	nM	None
Homo sapiens	K562	GI50	100000.0	nM	None
Homo sapiens	K562	IC50	41000.0	nM	10.1021/np800700e
Homo sapiens	KB	Activity	nan	None	10.1021/np800700e
Homo sapiens	KM12	GI50	100000.0	nM	None
Homo sapiens	LOX IMVI	GI50	100000.0	nM	None
Homo sapiens	M14	GI50	100000.0	nM	None
Homo sapiens	Malme-3M	GI50	78342.96	nM	None
Homo sapiens	MCF7	Activity	0.81	%	10.1021/np200866z
Homo sapiens	MCF7	Activity	nan	None	10.1021/np800700e
Homo sapiens	MCF7	GI50	100000.0	nM	None
Homo sapiens	MDA-MB-231	GI50	70794.58	nM	None
Homo sapiens	MDA-MB-435	GI50	100000.0	nM	None
Homo sapiens	MOLT-4	GI50	100000.0	nM	None
Homo sapiens	Multidrug resistance-associated protein 1	IC50	nan	None	10.1016/j.ejmech.2015.12.010
Homo sapiens	Multidrug resistance-associated protein 1	Inhibition	10.0	%	10.1016/j.ejmech.2020.112133
Homo sapiens	Multidrug resistance-associated protein 1	Ratio	nan	None	10.1016/j.bmc.2010.06.004
Homo sapiens	NCI/ADR-RES	GI50	100000.0	nM	None
Homo sapiens	NCI-H226	GI50	100000.0	nM	None
Homo sapiens	NCI-H23	GI50	100000.0	nM	None
Homo sapiens	NCI-H322M	GI50	100000.0	nM	None
Homo sapiens	NCI-H460	GI50	100000.0	nM	None
Homo sapiens	NCI-H460	IC50	148.0	nM	10.1016/j.bmcl.2017.09.009
Homo sapiens	NCI-H460	IC50	168.0	nM	10.1016/j.bmcl.2017.09.009
Homo sapiens	NCI-H460	IC50	186.0	nM	10.1016/j.bmcl.2017.09.009
Homo sapiens	NCI-H522	GI50	100000.0	nM	None
Homo sapiens	OVCAR-3	GI50	100000.0	nM	None
Homo sapiens	OVCAR-4	GI50	100000.0	nM	None
Homo sapiens	OVCAR-5	GI50	100000.0	nM	None
Homo sapiens	OVCAR-8	GI50	64416.93	nM	None
Homo sapiens	PC-3	GI50	100000.0	nM	None
Homo sapiens	P-glycoprotein 1	Activity	nan	None	10.1007/s00280-003-0745-2
Homo sapiens	P-glycoprotein 1	EC50	412.0	nM	10.1016/j.ejmech.2020.112133
Homo sapiens	P-glycoprotein 1	Emax	-20.0	%	10.1016/j.ejmech.2020.112133
Homo sapiens	P-glycoprotein 1	IC50	1808.0	nM	10.1016/j.ejmech.2020.112133
Homo sapiens	P-glycoprotein 1	IC50	nan	None	10.1016/j.ejmech.2015.12.010
Homo sapiens	P-glycoprotein 1	IC50	nan	None	10.1016/j.ejmech.2020.112133
Homo sapiens	P-glycoprotein 1	IC50	nan	None	10.1021/ml4000832
Homo sapiens	P-glycoprotein 1	Inhibition	0.8	%	10.1021/jm8013822
Homo sapiens	P-glycoprotein 1	Inhibition	22.0	%	10.1021/jm8013822
Homo sapiens	RPMI-8226	GI50	100000.0	nM	None
Homo sapiens	RXF 393	GI50	38106.58	nM	None
Homo sapiens	SF-268	GI50	43954.16	nM	None
Homo sapiens	SF-295	GI50	51286.14	nM	None
Homo sapiens	SF-539	GI50	29580.12	nM	None
Homo sapiens	SK-MEL-2	GI50	100000.0	nM	None
Homo sapiens	SK-MEL-28	GI50	22181.96	nM	None
Homo sapiens	SK-OV-3	GI50	29580.12	nM	None
Homo sapiens	SN12C	GI50	100000.0	nM	None
Homo sapiens	SNB-19	GI50	100000.0	nM	None
Homo sapiens	SNB-75	GI50	21677.04	nM	None
Homo sapiens	SR	GI50	100000.0	nM	None
Homo sapiens	SW-620	GI50	100000.0	nM	None
Homo sapiens	T47D	GI50	100000.0	nM	None
Homo sapiens	TK-10	GI50	29107.17	nM	None
Homo sapiens	U-251	GI50	73113.91	nM	None
Homo sapiens	UACC-257	GI50	100000.0	nM	None
Homo sapiens	UACC-62	GI50	87498.38	nM	None
Homo sapiens	UO-31	GI50	100000.0	nM	None
Klebsiella pneumoniae	Klebsiella pneumoniae	Inhibition	-0.45	%	10.6019/CHEMBL4296183
Mythimna separata	Mythimna separata	AFI	15.0	%	10.1021/jf300146n
Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	5.98	%	10.6019/CHEMBL4296183
Rattus norvegicus	PC-12	Activity	nan	None	10.1021/np800700e
Saccharomyces cerevisiae	Saccharomyces cerevisiae	IZ	0.0	mm	10.1016/j.ejmech.2010.07.050
Staphylococcus aureus	Staphylococcus aureus	Inhibition	-0.07	%	10.6019/CHEMBL4296183
None	NON-PROTEIN TARGET	IC50	0.82	nM	10.1021/acs.jnatprod.6b00597
None	Unchecked	Activity	100.0	%	10.1016/j.ejmech.2019.05.027
None	Unchecked	Activity	nan	None	10.1016/j.ejmech.2010.07.050
None	Unchecked	IC50	5.42	nM	10.1021/acs.jnatprod.6b00597
None	Unchecked	Ratio	7.0	None	10.1021/acs.jnatprod.6b00597
None	Unchecked	Ratio	nan	None	10.1016/j.bmc.2010.06.004
None	Unchecked	Ratio IC50	1.49	None	10.1016/j.bmcl.2017.09.009
None	Unchecked	Ratio IC50	2.1	None	10.1016/j.bmcl.2017.09.009
None	Unchecked	Ratio IC50	2.85	None	10.1016/j.bmcl.2017.09.009

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT011864	COc1ccc2c(C[C@@H]3NC(=O)[C@@H]4CCCN4C3=O)c(CC=C(C)C)[nH]c2c1>>COc1ccc2c3c([nH]c2c1)[C@H](C=C(C)C)N1C(=O)[C@@H]2CCCN2C(=O)[C@@H]1C3	RXN-14415
AKRT011905	COc1ccc2c3c([nH]c2c1)[C@H](C=C(C)C)N1C(=O)[C@@H]2CCCN2C(=O)[C@@H]1C3>>COc1ccc2c3c([nH]c2c1)[C@H](C=C(C)C)N1C(=O)[C@@H]2CCCN2C(=O)[C@]1(O)[C@H]3O	RXN-14414