NPASS Natural Product

Natural Product: NPC247902

Natural Product ID:	NPC247902
Common Name:	Epicorazine A
IUPAC Name:
Synonyms:	Epicorazine A
Molecular Formula:	C18H16N2O6S2
Standard InCHIKey:	RCODXLGTKJXDNC-UORGKRBOSA-N
Standard InCHI:	InChI=1S/C18H16N2O6S2/c21-9-1-3-11(23)13-7(9)5-17-15(25)20-14-8(10(22)2-4-12(14)24)6-18(20,28-27-17)16(26)19(13)17/h1-4,7-8,11-14,23-24H,5-6H2/t7-,8-,11+,12+,13+,14+,17-,18-/m1/s1
Canonical SMILES:	O[C@H]1C=CC(=O)[C@@H]2[C@@H]1N1C(=O)[C@]34SS[C@]1(C2)C(=O)N4[C@H]1[C@H](C3)C(=O)C=C[C@@H]1O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO18857	Pteronia eenii	Species	Asteraceae	Eukaryota	UNPD*
NPO9838	Eucalyptus maideni	Species	Myrtaceae	Eukaryota	UNPD*
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	UNPD*
NPO20485	Cussonia arborea	Species	Araliaceae	Eukaryota	UNPD*
NPO13404	Plantago subulata	Species	Plantaginaceae	Eukaryota	UNPD*
NPO21490	Hypoxylon fragiforme	Species	Xylariaceae	Eukaryota	UNPD*
NPO21558	Ormosia sumatrana	Species	Fabaceae	Eukaryota	UNPD*
NPO21431	Rapanea laetevirens	Species	Primulaceae	Eukaryota	UNPD*
NPO24508	Aspergillus brunneus	Species	Aspergillaceae	Eukaryota	UNPD*
NPO19907	Helicobasidium mompa	Species	Helicobasidiaceae	Eukaryota	UNPD*
NPO18114	Cyclamen repandum	Species	Primulaceae	Eukaryota	UNPD*
NPO19990	Axinyssa isabela	Species	Halichondriidae	Eukaryota	UNPD*
NPO19031	Thymus marschallianus	Species	Lamiaceae	Eukaryota	UNPD*
NPO21238	Berberis tabiensis	Species	Berberidaceae	Eukaryota	UNPD*
NPO18460	Trema dielsiana	Species	Cannabaceae	Eukaryota	UNPD*
NPO4994	Pachysandra procumbens	Species	Buxaceae	Eukaryota	UNPD*
NPO20747	Stictocardia campanulata	Species	Convolvulaceae	Eukaryota	UNPD*
NPO17541	Andryala pinnatifida	Species	Asteraceae	Eukaryota	UNPD*
NPO19796	Azolla filiculoides	Species	Azollaceae	Eukaryota	UNPD*
NPO33508	Phoma sp. OUCMDZ-1847	Species	Didymellaceae	Eukaryota	PMID[24370114]
NPO20276	Burasaia madagascariensis	Species	Menispermaceae	Eukaryota	UNPD*
NPO21301	Stereum hirsutum	Species	Stereaceae	Eukaryota	UNPD*

Biological Activity

Activity Type	# Activity
IC50	5
MIC	2
Others	1

Activity Type	# Activity
Cell Line	5
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32	ug/ml	22288374
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MIC	=	0.5	ug/ml	22288374
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Ratio	=	8		22288374
NPT3140	Cell Line	MGC-803	Homo sapiens	IC50	=	2700	nM	24370114
NPT111	Cell Line	K562	Homo sapiens	IC50	=	1500	nM	24370114
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2300	nM	24370114
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	330	nM	24370114
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	50	nM	24370114

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 NPC247902 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	82
0.1-0.2	593
0.2-0.3	7491
0.3-0.4	17269
0.4-0.5	4983
0.5-0.6	428
0.6-0.7	29
0.7-0.8	11
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC262880
0.9262	High Similarity	NPC41162
0.8647	High Similarity	NPC276822
0.7742	Intermediate Similarity	NPC309731
0.768	Intermediate Similarity	NPC272166
0.7424	Intermediate Similarity	NPC97580
0.7328	Intermediate Similarity	NPC266910
0.7248	Intermediate Similarity	NPC475342
0.7231	Intermediate Similarity	NPC470300
0.7231	Intermediate Similarity	NPC17581
0.7231	Intermediate Similarity	NPC476155
0.7209	Intermediate Similarity	NPC66007
0.7154	Intermediate Similarity	NPC28542
0.7007	Intermediate Similarity	NPC220396
0.6957	Remote Similarity	NPC25327
0.6917	Remote Similarity	NPC470788
0.6818	Remote Similarity	NPC271115
0.6788	Remote Similarity	NPC211848
0.6783	Remote Similarity	NPC82129
0.6619	Remote Similarity	NPC309525
0.6596	Remote Similarity	NPC8325
0.6591	Remote Similarity	NPC314550
0.6538	Remote Similarity	NPC207820
0.6528	Remote Similarity	NPC313348
0.6528	Remote Similarity	NPC475987
0.6457	Remote Similarity	NPC100810
0.6457	Remote Similarity	NPC144714
0.6449	Remote Similarity	NPC315188
0.6444	Remote Similarity	NPC288629
0.6443	Remote Similarity	NPC469800
0.6417	Remote Similarity	NPC324506
0.6309	Remote Similarity	NPC473955
0.6276	Remote Similarity	NPC120335
0.626	Remote Similarity	NPC472856
0.6259	Remote Similarity	NPC13351
0.622	Remote Similarity	NPC91036
0.6212	Remote Similarity	NPC271562
0.6202	Remote Similarity	NPC188785
0.6169	Remote Similarity	NPC243412
0.6084	Remote Similarity	NPC36254
0.6053	Remote Similarity	NPC315210
0.6053	Remote Similarity	NPC315848
0.6033	Remote Similarity	NPC475975
0.5987	Remote Similarity	NPC25025
0.5985	Remote Similarity	NPC476877
0.5962	Remote Similarity	NPC471680
0.5952	Remote Similarity	NPC145707
0.5946	Remote Similarity	NPC161644
0.5926	Remote Similarity	NPC476276
0.5896	Remote Similarity	NPC476876
0.5887	Remote Similarity	NPC471109
0.5871	Remote Similarity	NPC475266
0.5871	Remote Similarity	NPC475278
0.5871	Remote Similarity	NPC309450
0.5871	Remote Similarity	NPC304299
0.5871	Remote Similarity	NPC247776
0.5833	Remote Similarity	NPC77703
0.5821	Remote Similarity	NPC133420
0.5779	Remote Similarity	NPC88943
0.5778	Remote Similarity	NPC476328
0.5775	Remote Similarity	NPC474006
0.5775	Remote Similarity	NPC471673
0.5752	Remote Similarity	NPC45813
0.5736	Remote Similarity	NPC313265
0.5705	Remote Similarity	NPC97861
0.5705	Remote Similarity	NPC470539
0.5694	Remote Similarity	NPC139867
0.5693	Remote Similarity	NPC474099
0.5692	Remote Similarity	NPC469739
0.5683	Remote Similarity	NPC469455
0.5683	Remote Similarity	NPC476875
0.568	Remote Similarity	NPC322672
0.5676	Remote Similarity	NPC475610
0.5676	Remote Similarity	NPC476951
0.5674	Remote Similarity	NPC472536
0.5674	Remote Similarity	NPC103391
0.5669	Remote Similarity	NPC71866
0.5664	Remote Similarity	NPC174463
0.5664	Remote Similarity	NPC235625
0.5663	Remote Similarity	NPC327517
0.5663	Remote Similarity	NPC322372
0.5663	Remote Similarity	NPC319334
0.5656	Remote Similarity	NPC226982
0.5656	Remote Similarity	NPC277341
0.5655	Remote Similarity	NPC160688
0.5652	Remote Similarity	NPC274895
0.5635	Remote Similarity	NPC473525
0.5635	Remote Similarity	NPC168017
0.5633	Remote Similarity	NPC956
0.563	Remote Similarity	NPC265094
0.5625	Remote Similarity	NPC471261
0.5625	Remote Similarity	NPC47230
0.5625	Remote Similarity	NPC17143
0.5621	Remote Similarity	NPC473703
0.5621	Remote Similarity	NPC239252
0.562	Remote Similarity	NPC176773
0.5612	Remote Similarity	NPC251122
0.5612	Remote Similarity	NPC473232
0.5606	Remote Similarity	NPC476344
0.56	Remote Similarity	NPC76283
0.56	Remote Similarity	NPC319913

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC247902 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	88
0.1-0.2	312
0.2-0.3	2674
0.3-0.4	4585
0.4-0.5	1390
0.5-0.6	110
0.6-0.7	1
0.7-0.8	1
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
0.768	Intermediate Similarity	NPD1000	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD2645	Approved
0.5957	Remote Similarity	NPD2132	Phase 3
0.5957	Remote Similarity	NPD3159	Discontinued
0.5931	Remote Similarity	NPD3677	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD1806	Approved
0.5816	Remote Similarity	NPD961	Discontinued
0.5705	Remote Similarity	NPD6077	Discontinued
0.5694	Remote Similarity	NPD1689	Approved
0.5664	Remote Similarity	NPD1773	Discontinued
0.5633	Remote Similarity	NPD5193	Discontinued
0.5613	Remote Similarity	NPD5767	Discontinued
0.5603	Remote Similarity	NPD1376	Discontinued

Structure

CID247902 OpenBabel06191716052D 28 33 0 0 1 0 0 0 0 0999 V2000 3.2286 -2.1068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1396 0.7252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2286 -1.1051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1396 -0.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5407 -2.4164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4518 1.0348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4935 -2.1068 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4045 0.7252 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3610 -2.6077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2720 1.2261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3610 -0.6042 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2720 -0.7774 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4935 -1.1051 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4045 -0.2765 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0443 -1.5013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1333 0.1196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0481 -1.6060 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8630 0.2243 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5407 -0.7955 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4518 -0.5861 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3610 -3.6095 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2720 2.2278 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3610 0.3975 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2720 -1.7792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6331 -2.3117 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7221 0.9300 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3627 -0.8146 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 3 2 0 0 0 0 1 9 1 0 0 0 0 2 4 2 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 7 5 1 1 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 6 1 1 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 21 2 0 0 0 0 10 22 2 0 0 0 0 11 13 1 0 0 0 0 11 23 1 1 0 0 0 12 14 1 0 0 0 0 12 24 1 1 0 0 0 13 19 1 6 0 0 0 14 20 1 6 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 5 1 6 0 0 0 17 19 1 0 0 0 0 17 27 1 0 0 0 0 18 6 1 6 0 0 0 18 20 1 0 0 0 0 18 28 1 0 0 0 0 27 28 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	57383998
ChEMBL	CHEMBL2024572
ZINC

Physicochemical Properties

Molecular Weight:	420.04
ALogP:	-0.7542
MLogP:	2.34
XLogP:	-2.856
# Rotatable Bonds:	2
Polar Surface Area:	165.82
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	28

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