NPASS Natural Product

Natural Product: NPC220396

Natural Product ID:	NPC220396
Common Name:	Epicoccin A
IUPAC Name:
Synonyms:
Molecular Formula:	C18H18N2O6S3
Standard InCHIKey:	VZUJNQMBOQHGKN-DXOBHMFTSA-N
Standard InCHI:	InChI=1S/C18H18N2O6S3/c21-7-1-9-13(23)11-5(7)3-17(27-9)15(25)20-12-6-4-18(20,16(26)19(11)17)29-28-10(14(12)24)2-8(6)22/h5-6,9-14,23-24H,1-4H2/t5-,6-,9+,10+,11-,12-,13-,14-,17+,18+/m0/s1
Canonical SMILES:	O=C1C[C@H]2S[C@@]34C[C@@H]1[C@@H]([C@H]2O)N3C(=O)[C@]12N(C4=O)[C@@H]3[C@@H](O)[C@H](SS1)CC(=O)[C@@H]3C2
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Collection Location	Collection Time	Reference
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	The fungus is isolated from the leaves of L. rhodostegia, collected in June 2007 at Nanning, Guangxi Province, China	2007-JUN	PMID[20550196]
NPO27974	Swertia leduci	Species	Gentianaceae	Eukaryota			UNPD*
NPO28310	Phacelocarpus labillardieri	Species	Phacelocarpaceae	Eukaryota			UNPD*
NPO28114	Peltophorum adnatum	Species	Fabaceae	Eukaryota			UNPD*
NPO28219	Euphorbia peplus	Species	Euphorbiaceae	Eukaryota			UNPD*
NPO28982	Calliandra confusa	Species	Fabaceae	Eukaryota			UNPD*
NPO28129	Reticulitermes virginicus	Species	Termitoidae	Eukaryota			UNPD*
NPO23882	Cremastosperma microcarpum	Species	Annonaceae	Eukaryota			UNPD*
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota			J. Nat. Prod.,2007,70: 1522-1525
NPO33508	Phoma sp. OUCMDZ-1847	Species	Didymellaceae	Eukaryota			PMID[24370114]
NPO23676	Fleroya rubrostipulata	Species	Rubiaceae	Eukaryota			UNPD*

Biological Activity

Activity Type	# Activity
MIC	2
Others	1

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	12	mm	17711348
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	>	100	ug/ml	25462220
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	>	100	ug/ml	25462220

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 NPC220396 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	119
0.1-0.2	2910
0.2-0.3	18601
0.3-0.4	8463
0.4-0.5	718
0.5-0.6	63
0.6-0.7	2
0.7-0.8	6
0.8-0.85	1
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9576	High Similarity	NPC211848
0.916	High Similarity	NPC266910
0.8983	High Similarity	NPC28542
0.8889	High Similarity	NPC309731
0.8657	High Similarity	NPC243412
0.8636	High Similarity	NPC469800
0.8217	Intermediate Similarity	NPC8325
0.7939	Intermediate Similarity	NPC25327
0.784	Intermediate Similarity	NPC271115
0.7101	Intermediate Similarity	NPC41162
0.7055	Intermediate Similarity	NPC276822
0.7007	Intermediate Similarity	NPC262880
0.7007	Intermediate Similarity	NPC247902
0.6154	Remote Similarity	NPC97580
0.6053	Remote Similarity	NPC88943
0.5968	Remote Similarity	NPC168017
0.5926	Remote Similarity	NPC475342
0.5897	Remote Similarity	NPC956
0.5873	Remote Similarity	NPC178632
0.5845	Remote Similarity	NPC17581
0.5845	Remote Similarity	NPC476155
0.5634	Remote Similarity	NPC272166
0.5625	Remote Similarity	NPC470300
0.562	Remote Similarity	NPC241394
0.5606	Remote Similarity	NPC47076
0.5606	Remote Similarity	NPC134504

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC220396 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	89
0.1-0.2	1122
0.2-0.3	5070
0.3-0.4	2498
0.4-0.5	335
0.5-0.6	47
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	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5952	Remote Similarity	NPD2682	Approved
0.5923	Remote Similarity	NPD3714	Approved
0.5923	Remote Similarity	NPD3713	Approved
0.5923	Remote Similarity	NPD3715	Approved
0.5897	Remote Similarity	NPD5193	Discontinued
0.5634	Remote Similarity	NPD1000	Clinical (unspecified phase)
0.562	Remote Similarity	NPD6920	Discontinued
0.5606	Remote Similarity	NPD1784	Approved

Structure

CID220396 OpenBabel06191716012D 29 35 0 0 1 0 0 0 0 0999 V2000 2.1186 -0.9739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1506 -0.7051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1193 -1.6470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3954 -0.0821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6877 -0.8645 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9639 -0.8645 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9295 -1.2971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1151 -0.8526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8656 -0.1384 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0212 -0.6258 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1193 -0.0821 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3954 -1.6470 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4789 0.1916 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9198 -1.2660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3619 -1.8317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3619 0.1026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1995 -1.3481 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5244 -0.3810 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1995 -0.3810 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5244 -1.3481 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9967 -2.2618 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7432 -1.5880 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4355 1.1577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5690 -2.2766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3619 -2.7988 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3619 1.0697 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7413 -0.8237 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.6402 -0.1014 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 7 1 0 0 0 0 2 8 1 0 0 0 0 5 3 1 1 0 0 0 5 7 1 0 0 0 0 5 11 1 0 0 0 0 6 4 1 6 0 0 0 6 8 1 0 0 0 0 6 12 1 0 0 0 0 7 21 2 0 0 0 0 8 22 2 0 0 0 0 9 1 1 6 0 0 0 9 13 1 0 0 0 0 9 27 1 0 0 0 0 10 2 1 1 0 0 0 10 14 1 0 0 0 0 10 28 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 1 0 0 0 12 14 1 0 0 0 0 12 20 1 6 0 0 0 13 23 1 6 0 0 0 14 24 1 1 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 15 25 2 0 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 16 26 2 0 0 0 0 17 3 1 6 0 0 0 17 19 1 0 0 0 0 17 27 1 0 0 0 0 18 4 1 1 0 0 0 18 20 1 0 0 0 0 18 29 1 0 0 0 0 28 29 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	23642606
ChEMBL	CHEMBL399159
ZINC

Physicochemical Properties

Molecular Weight:	454.03
ALogP:	-0.917
MLogP:	2.23
XLogP:	-3.367
# Rotatable Bonds:	2
Polar Surface Area:	191.12
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	29

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