NPASS Natural Product

Natural Product: NPC470788

Natural Product ID:	NPC470788
Common Name:	Bisdethiobis(Methylthio)Gliotoxin
IUPAC Name:	(3R,6aR,7S,10bR)-7-hydroxy-3-(hydroxymethyl)-2-methyl-3,10b-bis(methylsulfanyl)-6a,7-dihydro-6H-pyrazino[2,1-a]isoindole-1,4-dione
Synonyms:
Molecular Formula:	C15H20N2O4S2
Standard InCHIKey:	DPYAQFVXNBCLEG-YZENIEGJSA-N
Standard InCHI:	InChI=1S/C15H20N2O4S2/c1-16-13(21)15(23-3)10-5-4-6-11(19)9(10)7-17(15)12(20)14(16,8-18)22-2/h4-6,9,11,18-19H,7-8H2,1-3H3/t9-,11-,14+,15+/m0/s1
Canonical SMILES:	OC[C@@]1(SC)C(=O)N2C[C@H]3C(=CC=C[C@@H]3O)[C@]2(C(=O)N1C)SC
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
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	stem bark of Melia azedarach			PMID[22409377]

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	33.5	ug/ml	23398362

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 NPC470788 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	443
0.2-0.3	6527
0.3-0.4	19260
0.4-0.5	3994
0.5-0.6	566
0.6-0.7	31
0.7-0.8	3
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.887	High Similarity	NPC17581
0.887	High Similarity	NPC476155
0.8136	Intermediate Similarity	NPC272166
0.8083	Intermediate Similarity	NPC470300
0.8067	Intermediate Similarity	NPC66007
0.7984	Intermediate Similarity	NPC97580
0.7538	Intermediate Similarity	NPC41162
0.7483	Intermediate Similarity	NPC475342
0.696	Remote Similarity	NPC314550
0.6917	Remote Similarity	NPC262880
0.6917	Remote Similarity	NPC247902
0.6833	Remote Similarity	NPC188785
0.6736	Remote Similarity	NPC276822
0.669	Remote Similarity	NPC471680
0.6493	Remote Similarity	NPC302169
0.6404	Remote Similarity	NPC475975
0.6357	Remote Similarity	NPC59249
0.6357	Remote Similarity	NPC120335
0.632	Remote Similarity	NPC476877
0.6296	Remote Similarity	NPC315188
0.6281	Remote Similarity	NPC469739
0.622	Remote Similarity	NPC476876
0.6214	Remote Similarity	NPC8325
0.6159	Remote Similarity	NPC36254
0.6154	Remote Similarity	NPC251122
0.6119	Remote Similarity	NPC28542
0.6107	Remote Similarity	NPC469455
0.6102	Remote Similarity	NPC324506
0.609	Remote Similarity	NPC474984
0.6069	Remote Similarity	NPC82129
0.6066	Remote Similarity	NPC313265
0.6061	Remote Similarity	NPC474995
0.6016	Remote Similarity	NPC40663
0.6014	Remote Similarity	NPC315848
0.6014	Remote Similarity	NPC315210
0.6	Remote Similarity	NPC277341
0.6	Remote Similarity	NPC226982
0.6	Remote Similarity	NPC302235
0.6	Remote Similarity	NPC309525
0.5985	Remote Similarity	NPC476875
0.5957	Remote Similarity	NPC476951
0.5952	Remote Similarity	NPC474985
0.5926	Remote Similarity	NPC288629
0.5926	Remote Similarity	NPC271115
0.5923	Remote Similarity	NPC271562
0.5906	Remote Similarity	NPC77703
0.5897	Remote Similarity	NPC314050
0.5897	Remote Similarity	NPC315809
0.5891	Remote Similarity	NPC133420
0.5878	Remote Similarity	NPC474099
0.5878	Remote Similarity	NPC207820
0.5859	Remote Similarity	NPC471097
0.5859	Remote Similarity	NPC475149
0.5846	Remote Similarity	NPC471259
0.5816	Remote Similarity	NPC211848
0.5793	Remote Similarity	NPC469666
0.5781	Remote Similarity	NPC100810
0.5781	Remote Similarity	NPC144714
0.5775	Remote Similarity	NPC474082
0.5775	Remote Similarity	NPC175726
0.5772	Remote Similarity	NPC90194
0.5772	Remote Similarity	NPC79465
0.5772	Remote Similarity	NPC293377
0.5772	Remote Similarity	NPC260045
0.5772	Remote Similarity	NPC475318
0.5772	Remote Similarity	NPC118099
0.5772	Remote Similarity	NPC9687
0.5772	Remote Similarity	NPC474787
0.5772	Remote Similarity	NPC476102
0.5772	Remote Similarity	NPC273907
0.5772	Remote Similarity	NPC49577
0.5772	Remote Similarity	NPC475598
0.5772	Remote Similarity	NPC76785
0.5772	Remote Similarity	NPC151706
0.5772	Remote Similarity	NPC474855
0.5772	Remote Similarity	NPC474811
0.5769	Remote Similarity	NPC283783
0.5764	Remote Similarity	NPC470539
0.5758	Remote Similarity	NPC476276
0.5755	Remote Similarity	NPC477140
0.5755	Remote Similarity	NPC477143
0.5736	Remote Similarity	NPC474244
0.5736	Remote Similarity	NPC473289
0.5735	Remote Similarity	NPC50694
0.5725	Remote Similarity	NPC476952
0.5714	Remote Similarity	NPC160688
0.5703	Remote Similarity	NPC475791
0.5703	Remote Similarity	NPC13175
0.5695	Remote Similarity	NPC89489
0.5693	Remote Similarity	NPC296043
0.5692	Remote Similarity	NPC279833
0.5692	Remote Similarity	NPC80439
0.5692	Remote Similarity	NPC471260
0.5692	Remote Similarity	NPC173690
0.5682	Remote Similarity	NPC176773
0.5677	Remote Similarity	NPC314358
0.5676	Remote Similarity	NPC99864
0.5674	Remote Similarity	NPC273185
0.5672	Remote Similarity	NPC473232
0.566	Remote Similarity	NPC473341
0.5658	Remote Similarity	NPC469800
0.5658	Remote Similarity	NPC239762
0.5658	Remote Similarity	NPC163392
0.5655	Remote Similarity	NPC25327
0.5652	Remote Similarity	NPC329216
0.5652	Remote Similarity	NPC201968
0.5649	Remote Similarity	NPC64168
0.5646	Remote Similarity	NPC300315
0.5638	Remote Similarity	NPC287401
0.5636	Remote Similarity	NPC328270
0.5625	Remote Similarity	NPC475758
0.5621	Remote Similarity	NPC304299
0.5621	Remote Similarity	NPC309450
0.5621	Remote Similarity	NPC247776
0.5621	Remote Similarity	NPC475266
0.5621	Remote Similarity	NPC475278
0.562	Remote Similarity	NPC103391
0.562	Remote Similarity	NPC472536
0.5615	Remote Similarity	NPC471258
0.5613	Remote Similarity	NPC243412
0.5613	Remote Similarity	NPC316008
0.5613	Remote Similarity	NPC313867
0.5612	Remote Similarity	NPC471673
0.5612	Remote Similarity	NPC201889
0.5612	Remote Similarity	NPC106791
0.5608	Remote Similarity	NPC120420
0.5606	Remote Similarity	NPC476328
0.5606	Remote Similarity	NPC472856

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470788 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	78
0.1-0.2	230
0.2-0.3	1954
0.3-0.4	5112
0.4-0.5	1522
0.5-0.6	256
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8136	Intermediate Similarity	NPD1000	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2645	Approved
0.6493	Remote Similarity	NPD1806	Approved
0.6391	Remote Similarity	NPD3159	Discontinued
0.6316	Remote Similarity	NPD1773	Discontinued
0.6232	Remote Similarity	NPD3677	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD2147	Approved
0.6131	Remote Similarity	NPD1748	Approved
0.6	Remote Similarity	NPD2148	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD805	Approved
0.5985	Remote Similarity	NPD806	Approved
0.5969	Remote Similarity	NPD777	Phase 3
0.5878	Remote Similarity	NPD5767	Discontinued
0.5846	Remote Similarity	NPD7333	Discontinued
0.5839	Remote Similarity	NPD2099	Approved
0.5821	Remote Similarity	NPD2090	Approved
0.5817	Remote Similarity	NPD5265	Approved
0.5817	Remote Similarity	NPD5264	Approved
0.58	Remote Similarity	NPD4126	Approved
0.5778	Remote Similarity	NPD1376	Discontinued
0.5775	Remote Similarity	NPD8273	Phase 1
0.5733	Remote Similarity	NPD5004	Approved
0.5733	Remote Similarity	NPD8173	Phase 2
0.5733	Remote Similarity	NPD8172	Phase 2
0.5724	Remote Similarity	NPD7751	Phase 1
0.5683	Remote Similarity	NPD1713	Approved
0.5676	Remote Similarity	NPD8415	Approved
0.5655	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.5646	Remote Similarity	NPD4125	Approved
0.5638	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD3561	Clinical (unspecified phase)

Structure

NPC470788 OpenBabel07101719512D 23 25 0 0 1 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 2.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3523 2.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 2.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9401 1.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5334 0.6045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1211 -0.2045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 1.9135 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 5 1 0 0 0 0 4 6 2 0 0 0 0 5 10 2 0 0 0 0 6 11 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 7 1 1 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 15 1 0 0 0 0 11 19 1 6 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 12 20 2 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 13 21 2 0 0 0 0 14 8 1 6 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	76325969
ChEMBL	CHEMBL2229126
ZINC

Physicochemical Properties

Molecular Weight:	356.09
ALogP:	-0.2554
MLogP:	2.23
XLogP:	-1.153
# Rotatable Bonds:	8
Polar Surface Area:	131.68
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	23

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