NPASS Natural Product

Natural Product: NPC201014

Natural Product ID:	NPC201014
Common Name:	Venturamide A
IUPAC Name:
Synonyms:
Molecular Formula:	C21H24N6O4S2
Standard InCHIKey:	OJMSNONHTSXZKM-GPCCPHFNSA-N
Standard InCHI:	InChI=1S/C21H24N6O4S2/c1-8(2)14-21-25-12(7-33-21)16(28)22-9(3)19-27-15(11(5)31-19)18(30)23-10(4)20-24-13(6-32-20)17(29)26-14/h6-10,14H,1-5H3,(H,22,28)(H,23,30)(H,26,29)/t9-,10-,14-/m1/s1
Canonical SMILES:	CC([C@H]1N=C(O)c2csc(n2)[C@@H](C)N=C(O)c2nc([C@H](N=C(c3nc1sc3)O)C)oc2C)C
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
NPO31273	Oscillatoria sp.	Species	Oscillatoriaceae	Bacteria				PMID[17328572]

Biological Activity

Activity Type	# Activity
IC50	7

Activity Type	# Activity
Cell Line	3
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	8200	nM	17328572
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	14600	nM	17328572
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	20000	nM	17328572
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	86000	nM	17328572
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	13100	nM	17328572
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	8200	nM	18973386
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	13100	nM	18973386

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 NPC201014 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	225
0.1-0.2	13580
0.2-0.3	13958
0.3-0.4	2825
0.4-0.5	203
0.5-0.6	78
0.6-0.7	11
0.7-0.8	2
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC110129
0.9866	High Similarity	NPC222391
0.9796	High Similarity	NPC217981
0.9671	High Similarity	NPC34319
0.9542	High Similarity	NPC256912
0.8581	High Similarity	NPC50274
0.8428	Intermediate Similarity	NPC237219
0.7617	Intermediate Similarity	NPC235866
0.7124	Intermediate Similarity	NPC51692
0.6975	Remote Similarity	NPC103268
0.6943	Remote Similarity	NPC89592
0.6908	Remote Similarity	NPC214375
0.677	Remote Similarity	NPC74917
0.6728	Remote Similarity	NPC120917
0.671	Remote Similarity	NPC135558
0.6627	Remote Similarity	NPC475390
0.6582	Remote Similarity	NPC267605
0.6465	Remote Similarity	NPC315872
0.6304	Remote Similarity	NPC164006
0.6138	Remote Similarity	NPC132662
0.5943	Remote Similarity	NPC469801
0.5888	Remote Similarity	NPC49195
0.5817	Remote Similarity	NPC315061
0.58	Remote Similarity	NPC315411
0.5798	Remote Similarity	NPC475554
0.5753	Remote Similarity	NPC216720
0.5729	Remote Similarity	NPC134480
0.5722	Remote Similarity	NPC161242
0.5722	Remote Similarity	NPC210424
0.5722	Remote Similarity	NPC476080
0.5722	Remote Similarity	NPC475534
0.5707	Remote Similarity	NPC96016
0.5699	Remote Similarity	NPC473704
0.5692	Remote Similarity	NPC475330
0.5663	Remote Similarity	NPC263485
0.5663	Remote Similarity	NPC229160
0.5663	Remote Similarity	NPC174652
0.5663	Remote Similarity	NPC25316

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC201014 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	1596
0.2-0.3	4109
0.3-0.4	2914
0.4-0.5	382
0.5-0.6	20
0.6-0.7	2
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
0.6465	Remote Similarity	NPD6444	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD2623	Phase 1
0.5805	Remote Similarity	NPD7896	Approved

Structure

CID201014 OpenBabel06191715592D 33 36 0 0 1 0 0 0 0 0999 V2000 1.3706 2.8482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4183 2.8559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3634 -3.8348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8851 -2.3061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2676 -2.1846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7160 0.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4622 -0.7742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4739 2.3357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -3.3452 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0312 -1.8000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7483 -3.0825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3637 -0.7611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1676 0.7840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4695 1.3029 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1985 -3.8637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3793 -1.7948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2724 1.3011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1074 -3.3482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3951 -3.8623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0469 -0.7664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4394 0.7874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4842 -2.3119 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.1223 -2.3155 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.1519 -0.2497 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4553 -0.2459 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3635 0.7857 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3036 -3.3471 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2442 -2.2892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2763 2.2973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9646 -3.8559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8466 -3.0818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1557 -0.7595 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 8 1 0 0 0 0 2 8 1 0 0 0 0 5 11 1 0 0 0 0 6 13 2 0 0 0 0 6 32 1 0 0 0 0 7 12 2 0 0 0 0 7 33 1 0 0 0 0 9 3 1 1 0 0 0 9 19 1 0 0 0 0 9 22 1 0 0 0 0 10 4 1 1 0 0 0 10 20 1 0 0 0 0 10 23 1 0 0 0 0 11 15 2 0 0 0 0 11 31 1 0 0 0 0 12 16 1 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 24 1 0 0 0 0 14 8 1 1 0 0 0 14 21 1 0 0 0 0 14 26 1 0 0 0 0 15 18 1 0 0 0 0 15 27 1 0 0 0 0 16 22 2 3 0 0 0 16 28 1 0 0 0 0 17 26 2 3 0 0 0 17 29 1 0 0 0 0 18 23 2 3 0 0 0 18 30 1 0 0 0 0 19 27 2 0 0 0 0 19 31 1 0 0 0 0 20 24 2 0 0 0 0 20 32 1 0 0 0 0 21 25 2 0 0 0 0 21 33 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	11225555
ChEMBL	CHEMBL375099
ZINC

Physicochemical Properties

Molecular Weight:	488.13
ALogP:	1.4098
MLogP:	2.45
XLogP:	3.389
# Rotatable Bonds:	9
Polar Surface Area:	206.06
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	33

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