NPASS Natural Product

Natural Product: NPC272166

Natural Product ID:	NPC272166
Common Name:	Gliotoxin
IUPAC Name:
Synonyms:	Gliotoxin
Molecular Formula:	C13H14N2O4S2
Standard InCHIKey:	FIVPIPIDMRVLAY-RBJBARPLSA-N
Standard InCHI:	InChI=1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13+/m0/s1
Canonical SMILES:	OC[C@@]12SS[C@@]3(N(C1=O)[C@@H]1[C@@H](O)C=CC=C1C3)C(=O)N2C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	BGC0000361 ;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	PMID[22148349]
NPO3593	Lagochilus inebrians	Species	Lamiaceae	Eukaryota	UNPD*
NPO9410	Saussurea macrota	Species	Asteraceae	Eukaryota	UNPD*
NPO1256	Boronia ledifolia	Species	Rutaceae	Eukaryota	UNPD*
NPO45	Sterculia parviflora	Species	Malvaceae	Eukaryota	UNPD*
NPO10070	Scorzonera latifolia	Species	Asteraceae	Eukaryota	UNPD*
NPO4038	Phelline comosa	Species	Phellinaceae	Eukaryota	UNPD*
NPO677	Parmelia abessinica	Species	Parmeliaceae	Eukaryota	UNPD*
NPO12137	Elysia tuca	Species	Placobranchidae	Eukaryota	UNPD*

Biological Activity

Activity Type	# Activity
EC50	1
ED50	9
IC50	22
LD50	1
MIC	15
Others	7
Potency	6

Activity Type	# Activity
Cell Line	7
Individual Protein	12
Organism	28
Others	11
Protein Complex	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1180	Protein Complex	Protein farnesyltransferase	Homo sapiens	IC50	=	1100	nM	9301658
NPT1180	Protein Complex	Protein farnesyltransferase	Homo sapiens	IC50	=	80000	nM	14552752
NPT1181	Protein Complex	Geranylgeranyl transferase type I	Homo sapiens	IC50	=	17000	nM	14552752
NPT4849	Cell Line	P815	Mus musculus	ED50	=	0.002	nM	10.1016/S0960-894X(97)10052-X
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	0.35	nM	10.1016/S0960-894X(97)10052-X
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	59	%	10.1016/S0960-894X(97)10052-X
NPT5109	Individual Protein	Creatine kinase M	Homo sapiens	Activity	=	32	%	10.1016/S0960-894X(97)10052-X
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	3100	nM	16124785
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	150	nM	16124785
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2450	nM	20303767
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	10	nM	20303767
NPT2	Others	Unspecified		IC50	>	50000	nM	20303767
NPT2	Others	Unspecified		IC50	=	500	nM	20303767
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	<	1000	nM	20303767
NPT561	Organism	Tetrahymena pyriformis	Tetrahymena pyriformis	EC50	=	380	nM	20303767
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3	nM	20303767
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	123	nM	20303767
NPT2	Others	Unspecified		IC50	=	93000	nM	20303767
NPT2	Others	Unspecified		Activity	=	300	nM	20303767
NPT5633	Individual Protein	Acetolactate synthase catalytic subunit, mitochondrial	Saccharomyces cerevisiae S288c	IC50	=	200	nM	20303767
NPT2	Others	Unspecified		IC50	=	10000	nM	20303767
NPT5634	Individual Protein	Mycothiol S-conjugate amidase	Mycobacterium tuberculosis	IC50	=	50000	nM	20303767
NPT2703	Organism	Rhizoctonia bataticola	Rhizoctonia bataticola	ED50	=	0.9	nM	20303767
NPT4304	Organism	Macrophomina phaseolina	Macrophomina phaseolina	ED50	=	5.4	nM	20303767
NPT2701	Organism	Pythium debaryanum	Pythium debaryanum	ED50	=	90.12	nM	20303767
NPT961	Organism	Pythium aphanidermatum	Pythium aphanidermatum	ED50	=	36.87	nM	20303767
NPT722	Organism	Athelia rolfsii	Athelia rolfsii	ED50	=	6.47	nM	20303767
NPT529	Organism	Rhizoctonia solani	Rhizoctonia solani	ED50	=	9.75	nM	20303767
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	3600	nM	20303767
NPT32	Organism	Mus musculus	Mus musculus	LD50	=	17.9	mg/kg	20303767
NPT2	Others	Unspecified		ED50	=	0.104	nM	20303767
NPT2	Others	Unspecified		Activity	=	30.7	nM	20303767
NPT2	Others	Unspecified		Activity	=	0.3	nM	20303767
NPT2	Others	Unspecified		IC50	=	9000	nM	20303767
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	0.5	ug/ml	18212113
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	8	ug/ml	18212113
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	2	ug/ml	18212113
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	16	ug/ml	18212113
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	0.06	ug/ml	18212113
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	0.125	ug/ml	18212113
NPT53	Individual Protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	2511.9	nM	PubChem BioAssay data set
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	22334.2	nM	PubChem BioAssay data set
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	44.7	nM	PubChem BioAssay data set
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency		3981.1	nM	PubChem BioAssay data set
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	4	ug/ml	21761939
NPT168	Cell Line	P388	Mus musculus	IC50	=	24	nM	22148349
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	IC50	=	6400	nM	22148349
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-11.27	%	23062825
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	10.3	%	23062825
NPT5635	Individual Protein	Histone-lysine N-methyltransferase SUV39H1	Homo sapiens	IC50	=	260	nM	22975593
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	IC50	=	530	nM	22975593
NPT2	Others	Unspecified		Potency		2511.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		1412.5	nM	PubChem BioAssay data set

Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC272166 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	60
0.1-0.2	442
0.2-0.3	7699
0.3-0.4	18540
0.4-0.5	3640
0.5-0.6	472
0.6-0.7	24
0.7-0.8	6
0.8-0.85	3
0.85-0.9	0
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9358	High Similarity	NPC66007
0.9189	High Similarity	NPC476155
0.9189	High Similarity	NPC17581
0.8362	Intermediate Similarity	NPC470300
0.825	Intermediate Similarity	NPC97580
0.8136	Intermediate Similarity	NPC470788
0.768	Intermediate Similarity	NPC247902
0.768	Intermediate Similarity	NPC262880
0.7364	Intermediate Similarity	NPC41162
0.7174	Intermediate Similarity	NPC276822
0.709	Intermediate Similarity	NPC82129
0.7083	Intermediate Similarity	NPC475342
0.678	Remote Similarity	NPC188785
0.664	Remote Similarity	NPC314550
0.6636	Remote Similarity	NPC475975
0.6528	Remote Similarity	NPC471680
0.6423	Remote Similarity	NPC120335
0.6393	Remote Similarity	NPC476877
0.6343	Remote Similarity	NPC36254
0.629	Remote Similarity	NPC476876
0.6271	Remote Similarity	NPC313265
0.6241	Remote Similarity	NPC315188
0.6231	Remote Similarity	NPC271115
0.6218	Remote Similarity	NPC469739
0.6202	Remote Similarity	NPC309731
0.6174	Remote Similarity	NPC324506
0.6159	Remote Similarity	NPC166169
0.6107	Remote Similarity	NPC288629
0.6071	Remote Similarity	NPC277341
0.6071	Remote Similarity	NPC226982
0.6058	Remote Similarity	NPC309525
0.6054	Remote Similarity	NPC470301
0.6047	Remote Similarity	NPC476875
0.6047	Remote Similarity	NPC469455
0.6043	Remote Similarity	NPC25327
0.6	Remote Similarity	NPC25025
0.5969	Remote Similarity	NPC251122
0.5968	Remote Similarity	NPC100810
0.5968	Remote Similarity	NPC144714
0.5959	Remote Similarity	NPC315210
0.5959	Remote Similarity	NPC315848
0.5952	Remote Similarity	NPC133420
0.594	Remote Similarity	NPC28542
0.5938	Remote Similarity	NPC207820
0.592	Remote Similarity	NPC473289
0.5882	Remote Similarity	NPC266910
0.5878	Remote Similarity	NPC475266
0.5878	Remote Similarity	NPC475278
0.5878	Remote Similarity	NPC309450
0.5878	Remote Similarity	NPC304299
0.5878	Remote Similarity	NPC247776
0.5859	Remote Similarity	NPC271562
0.5845	Remote Similarity	NPC469666
0.584	Remote Similarity	NPC77703
0.5839	Remote Similarity	NPC302169
0.5827	Remote Similarity	NPC474082
0.5827	Remote Similarity	NPC175726
0.5816	Remote Similarity	NPC8325
0.5814	Remote Similarity	NPC474099
0.5786	Remote Similarity	NPC476951
0.5781	Remote Similarity	NPC472856
0.5778	Remote Similarity	NPC471673
0.5765	Remote Similarity	NPC302235
0.5764	Remote Similarity	NPC313348
0.5764	Remote Similarity	NPC475987
0.5752	Remote Similarity	NPC471768
0.5726	Remote Similarity	NPC91036
0.5725	Remote Similarity	NPC273185
0.5724	Remote Similarity	NPC99864
0.5702	Remote Similarity	NPC209232
0.5693	Remote Similarity	NPC13351
0.5692	Remote Similarity	NPC476276
0.5669	Remote Similarity	NPC475149
0.5669	Remote Similarity	NPC471097
0.5667	Remote Similarity	NPC71866
0.5655	Remote Similarity	NPC120420
0.5652	Remote Similarity	NPC160688
0.5646	Remote Similarity	NPC248283
0.5643	Remote Similarity	NPC211848
0.5635	Remote Similarity	NPC475791
0.5635	Remote Similarity	NPC13175
0.5634	Remote Similarity	NPC220396
0.5625	Remote Similarity	NPC161644
0.5625	Remote Similarity	NPC473254
0.5621	Remote Similarity	NPC314358
0.5616	Remote Similarity	NPC473703
0.5616	Remote Similarity	NPC239252
0.5615	Remote Similarity	NPC176773
0.5608	Remote Similarity	NPC76785
0.5608	Remote Similarity	NPC474855
0.5608	Remote Similarity	NPC293377
0.5608	Remote Similarity	NPC9687
0.5608	Remote Similarity	NPC151706
0.5608	Remote Similarity	NPC474811
0.5608	Remote Similarity	NPC79465
0.5608	Remote Similarity	NPC260045
0.5608	Remote Similarity	NPC476102
0.5608	Remote Similarity	NPC475598
0.5608	Remote Similarity	NPC475318
0.5608	Remote Similarity	NPC118099
0.5608	Remote Similarity	NPC273907
0.5608	Remote Similarity	NPC474787
0.5608	Remote Similarity	NPC90194
0.5608	Remote Similarity	NPC49577

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC272166 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	72
0.1-0.2	242
0.2-0.3	2166
0.3-0.4	5020
0.4-0.5	1468
0.5-0.6	192
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1000	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD7333	Discontinued
0.5827	Remote Similarity	NPD8273	Phase 1
0.5809	Remote Similarity	NPD2645	Approved
0.5735	Remote Similarity	NPD3159	Discontinued
0.5725	Remote Similarity	NPD1806	Approved
0.5724	Remote Similarity	NPD8415	Approved
0.5714	Remote Similarity	NPD1376	Discontinued
0.5694	Remote Similarity	NPD5263	Approved
0.5685	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6073	Approved
0.5676	Remote Similarity	NPD8172	Phase 2
0.5676	Remote Similarity	NPD8173	Phase 2
0.5643	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4175	Approved
0.5625	Remote Similarity	NPD4177	Approved
0.5615	Remote Similarity	NPD2147	Approved
0.5608	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD3072	Approved
0.5603	Remote Similarity	NPD3071	Approved
0.5603	Remote Similarity	NPD3073	Approved

Structure

CID272166 OpenBabel06191716082D 21 24 0 0 1 0 0 0 0 0999 V2000 -1.6817 -1.9217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1185 -1.4279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2948 -1.9033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1187 -0.4763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 -1.9029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7750 -0.4751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4709 -1.4276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2952 -0.0006 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4711 -0.4760 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0008 -1.9026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0004 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8233 -1.4273 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8240 -0.4754 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8242 -1.4269 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8235 -0.4757 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1637 -1.3430 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2955 0.9856 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0010 -2.8889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 0.9863 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8237 -0.4759 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 3 1 0 0 0 0 2 4 2 0 0 0 0 3 7 2 0 0 0 0 4 8 1 0 0 0 0 5 7 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 6 16 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 1 0 0 0 9 7 1 6 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 14 1 0 0 0 0 10 18 2 0 0 0 0 11 15 1 0 0 0 0 11 19 2 0 0 0 0 12 15 1 0 0 0 0 12 20 1 6 0 0 0 13 11 1 1 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 20 21 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	6223
ChEMBL	CHEMBL331627
ZINC

Physicochemical Properties

Molecular Weight:	326.04
ALogP:	-0.1535
MLogP:	2.01
XLogP:	-2.142
# Rotatable Bonds:	4
Polar Surface Area:	131.68
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	21

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