Molecule

Demethoxyfumitremorgin C

AlkaPlorer ID: AK017223

Synonym: None

IUPAC Name: (1S,12S,15S)-12-(2-methylprop-1-enyl)-10,13,19-triazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-3(11),4,6,8-tetraene-14,20-dione

Structure

SMILES: CC(C)=C[C@H]1C2=C(C[C@H]3C(=O)N4CCC[C@H]4C(=O)N31)C1=CC=CC=C1N2

InChI: InChI=1S/C21H23N3O2/c1-12(2)10-17-19-14(13-6-3-4-7-15(13)22-19)11-18-20(25)23-9-5-8-16(23)21(26)24(17)18/h3-4,6-7,10,16-18,22H,5,8-9,11H2,1-2H3/t16-,17-,18-/m0/s1

InChIKey: LQXCSIKDOISJTI-BZSNNMDCSA-N

Reference

Novel mammalian cell cycle inhibitors, spirotryprostatins A and B, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase

PubChem CID: 10337896

LOTUS: LTS0196039

NPASS: NPC161861

{

NPAtlas: NPA014999

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Aspergillus fumigatus	Aspergillus	Aspergillaceae	Eurotiales	Eurotiomycetes	Ascomycota	Fungi	Eukaryota
None	Aspergillus	Aspergillaceae	Eurotiales	Eurotiomycetes	Ascomycota	Fungi	Eukaryota
None	Aspergillus	Aspergillaceae	Eurotiales	Eurotiomycetes	Ascomycota	Fungi	Eukaryota

Properties Information

Molecule Weight: 349.434

TPSA？: 56.41

MolLogP？: 2.9331000000000014

Number of H-Donors: 1

Number of H-Acceptors: 2

RingCount: 5

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Homo sapiens	ATP-binding cassette sub-family G member 2	Inhibition	nan	%	10.1016/j.bmcl.2016.11.013
Homo sapiens	Breast carcinoma cell	IC50	37153.52	nM	10.1021/jm9905662
Homo sapiens	Breast carcinoma cell	IC50	100000.0	nM	10.1021/jm9905662
Homo sapiens	CNS cell	IC50	43651.58	nM	10.1021/jm9905662
Homo sapiens	CNS cell	IC50	100000.0	nM	10.1021/jm9905662
Homo sapiens	Colon cell	IC50	53703.18	nM	10.1021/jm9905662
Homo sapiens	Colon cell	IC50	95499.26	nM	10.1021/jm9905662
Homo sapiens	K562	IC50	41000.0	nM	10.1021/np800700e
Homo sapiens	KB	Activity	nan	None	10.1021/np800700e
Homo sapiens	MCF7	Activity	nan	None	10.1021/np800700e
Homo sapiens	Melanoma cell	IC50	47863.01	nM	10.1021/jm9905662
Homo sapiens	Melanoma cell	IC50	100000.0	nM	10.1021/jm9905662
Homo sapiens	Ovarian carcinoma cell	IC50	70794.58	nM	10.1021/jm9905662
Homo sapiens	Ovarian carcinoma cell	IC50	100000.0	nM	10.1021/jm9905662
Homo sapiens	Panel leukemia (Carcinoma cell lines)	IC50	34673.69	nM	10.1021/jm9905662
Homo sapiens	Panel leukemia (Carcinoma cell lines)	IC50	69183.1	nM	10.1021/jm9905662
Homo sapiens	Prostate cell	IC50	50118.72	nM	10.1021/jm9905662
Homo sapiens	Prostate cell	IC50	100000.0	nM	10.1021/jm9905662
Homo sapiens	Renal cell	IC50	24547.09	nM	10.1021/jm9905662
Homo sapiens	Renal cell	IC50	100000.0	nM	10.1021/jm9905662
Mus musculus	NSO	IC50	52480.75	nM	10.1021/jm9905662
Mus musculus	NSO	IC50	93325.43	nM	10.1021/jm9905662
Rattus norvegicus	3Y1 cell line	GI50	43651.58	nM	10.1021/jm9905662
Rattus norvegicus	3Y1 cell line	GI50	95499.26	nM	10.1021/jm9905662
Rattus norvegicus	3Y1 cell line	LC50	-4.0	None	10.1021/jm9905662
Rattus norvegicus	3Y1 cell line	TGI	-4.02	None	10.1021/jm9905662
Rattus norvegicus	3Y1 cell line	TGI	4.0	None	10.1021/jm9905662
Rattus norvegicus	PC-12	Activity	nan	None	10.1021/np800700e

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT005316	CC(C)=CCc1[nH]c2ccccc2c1C[C@@H]1NC(=O)[C@@H]2CCCN2C1=O>>CC(C)=C[C@H]1c2[nH]c3ccccc3c2C[C@H]2C(=O)N3CCC[C@H]3C(=O)N21	RXN-14416