NPASS Natural Product

Natural Product: NPC66007

Natural Product ID:	NPC66007
Common Name:	Gliotoxin G
IUPAC Name:
Synonyms:	Gliotoxin G
Molecular Formula:	C13H14N2O4S4
Standard InCHIKey:	TZBWGHOEGGDHNR-RBJBARPLSA-N
Standard InCHI:	InChI=1S/C13H14N2O4S4/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-23-22-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13+/m0/s1
Canonical SMILES:	OC[C@@]12SSSS[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:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota				PMID[22148349]

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	IC50	=	2100	nM	10.1039/C3MD20353K
NPT168	Cell Line	P388	Mus musculus	IC50	=	20	nM	10.1021/np50010a008

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 NPC66007 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	471
0.2-0.3	9632
0.3-0.4	17235
0.4-0.5	3053
0.5-0.6	408
0.6-0.7	20
0.7-0.8	4
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	NPC272166
0.9107	High Similarity	NPC476155
0.9107	High Similarity	NPC17581
0.8291	Intermediate Similarity	NPC470300
0.8182	Intermediate Similarity	NPC97580
0.8067	Intermediate Similarity	NPC470788
0.7209	Intermediate Similarity	NPC262880
0.7209	Intermediate Similarity	NPC247902
0.7176	Intermediate Similarity	NPC41162
0.7034	Intermediate Similarity	NPC475342
0.6761	Remote Similarity	NPC276822
0.6723	Remote Similarity	NPC188785
0.6667	Remote Similarity	NPC82129
0.6587	Remote Similarity	NPC314550
0.6577	Remote Similarity	NPC475975
0.6377	Remote Similarity	NPC120335
0.637	Remote Similarity	NPC471680
0.6341	Remote Similarity	NPC476877
0.6296	Remote Similarity	NPC36254
0.624	Remote Similarity	NPC476876
0.6218	Remote Similarity	NPC313265
0.6194	Remote Similarity	NPC315188
0.6183	Remote Similarity	NPC288629
0.6167	Remote Similarity	NPC469739
0.6121	Remote Similarity	NPC324506
0.6018	Remote Similarity	NPC277341
0.6018	Remote Similarity	NPC226982
0.6014	Remote Similarity	NPC309525
0.6	Remote Similarity	NPC469455
0.6	Remote Similarity	NPC476875
0.5923	Remote Similarity	NPC251122
0.5891	Remote Similarity	NPC207820
0.5873	Remote Similarity	NPC473289
0.585	Remote Similarity	NPC25025
0.5833	Remote Similarity	NPC166169
0.5821	Remote Similarity	NPC271115
0.5814	Remote Similarity	NPC271562
0.5804	Remote Similarity	NPC469666
0.5797	Remote Similarity	NPC302169
0.5794	Remote Similarity	NPC77703
0.5789	Remote Similarity	NPC309731
0.5786	Remote Similarity	NPC474082
0.5786	Remote Similarity	NPC175726
0.5781	Remote Similarity	NPC133420
0.5778	Remote Similarity	NPC28542
0.5769	Remote Similarity	NPC474099
0.5745	Remote Similarity	NPC476951
0.5735	Remote Similarity	NPC471673
0.5733	Remote Similarity	NPC309450
0.5733	Remote Similarity	NPC247776
0.5733	Remote Similarity	NPC475266
0.5733	Remote Similarity	NPC304299
0.5733	Remote Similarity	NPC475278
0.5731	Remote Similarity	NPC302235
0.5705	Remote Similarity	NPC315210
0.5705	Remote Similarity	NPC315848
0.5702	Remote Similarity	NPC471768
0.5695	Remote Similarity	NPC470301
0.5683	Remote Similarity	NPC273185
0.5664	Remote Similarity	NPC25327
0.5664	Remote Similarity	NPC8325
0.5652	Remote Similarity	NPC209232
0.5649	Remote Similarity	NPC476276
0.5629	Remote Similarity	NPC71866
0.5625	Remote Similarity	NPC475149
0.5625	Remote Similarity	NPC471097
0.5612	Remote Similarity	NPC266910
0.5612	Remote Similarity	NPC160688
0.5608	Remote Similarity	NPC248283

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC66007 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	253
0.2-0.3	2458
0.3-0.4	4948
0.4-0.5	1257
0.5-0.6	172
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9358	High Similarity	NPD1000	Clinical (unspecified phase)
0.5786	Remote Similarity	NPD8273	Phase 1
0.5766	Remote Similarity	NPD2645	Approved
0.5736	Remote Similarity	NPD7333	Discontinued
0.5693	Remote Similarity	NPD3159	Discontinued
0.5683	Remote Similarity	NPD1806	Approved
0.5672	Remote Similarity	NPD1376	Discontinued
0.5655	Remote Similarity	NPD5263	Approved
0.5638	Remote Similarity	NPD8172	Phase 2
0.5638	Remote Similarity	NPD6073	Approved
0.5638	Remote Similarity	NPD8173	Phase 2
0.5603	Remote Similarity	NPD4706	Clinical (unspecified phase)

Structure

NPC66007 OpenBabel07101718232D 23 26 0 0 1 0 0 0 0 0999 V2000 -0.5286 -0.4059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1381 1.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2720 1.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1381 0.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4549 1.5258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3233 -2.0733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4060 1.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2720 -0.2833 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4060 0.2167 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8726 0.6122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0482 -1.0058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8672 0.7167 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0537 -1.1104 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4659 -0.3013 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4549 -0.0923 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6241 -2.7883 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2720 -1.2833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2849 1.4212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6360 -1.8148 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1104 1.0537 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.2969 -0.7734 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.3370 0.7568 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 6 16 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 6 0 0 0 9 7 1 1 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 13 1 0 0 0 0 11 15 1 0 0 0 0 11 19 2 0 0 0 0 12 5 1 6 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 6 1 6 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 23 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	3007092
ChEMBL	CHEMBL1950962
ZINC

Physicochemical Properties

Molecular Weight:	389.98
ALogP:	1.0277
MLogP:	1.79
XLogP:	-1.632
# Rotatable Bonds:	4
Polar Surface Area:	182.28
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	23

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs