NPASS Natural Product

Natural Product: NPC278902

Natural Product ID:	NPC278902
Common Name:	Herbamide B
IUPAC Name:	(2E,4E,7S)-8,8,8-trichloro-2,7-dimethyl-N-[(1S)-2-methyl-1-(1,3-thiazol-2-yl)propyl]octa-2,4-dienamide
Synonyms:
Molecular Formula:	C17H23Cl3N2OS
Standard InCHIKey:	SASMNYHOQIJNIJ-CBZHAUGTSA-N
Standard InCHI:	InChI=1S/C17H23Cl3N2OS/c1-11(2)14(16-21-9-10-24-16)22-15(23)12(3)7-5-6-8-13(4)17(18,19)20/h5-7,9-11,13-14H,8H2,1-4H3,(H,22,23)/b6-5+,12-7+/t13-,14-/m0/s1
Canonical SMILES:	C/C(=CC=CC[C@@H](C(Cl)(Cl)Cl)C)/C(=N[C@H](c1nccs1)C(C)C)O
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
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria				PMID[20030365]

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	10000	nM	18591268
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	10000	nM	17698630
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	5900	nM	2128517

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 NPC278902 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	216
0.1-0.2	14212
0.2-0.3	12980
0.3-0.4	3019
0.4-0.5	365
0.5-0.6	85
0.6-0.7	9
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7462	Intermediate Similarity	NPC145047
0.7462	Intermediate Similarity	NPC137705
0.7462	Intermediate Similarity	NPC86490
0.6781	Remote Similarity	NPC478251
0.6781	Remote Similarity	NPC478252
0.6761	Remote Similarity	NPC478254
0.6761	Remote Similarity	NPC478253
0.6726	Remote Similarity	NPC261708
0.6709	Remote Similarity	NPC475920
0.6014	Remote Similarity	NPC475568
0.6	Remote Similarity	NPC475604
0.6	Remote Similarity	NPC275393
0.5929	Remote Similarity	NPC214375
0.5845	Remote Similarity	NPC135558
0.5843	Remote Similarity	NPC473886
0.5806	Remote Similarity	NPC469801
0.5805	Remote Similarity	NPC161143
0.5796	Remote Similarity	NPC319751
0.5732	Remote Similarity	NPC315252
0.5724	Remote Similarity	NPC51692
0.5723	Remote Similarity	NPC473398
0.5687	Remote Similarity	NPC119481
0.5621	Remote Similarity	NPC474070
0.5616	Remote Similarity	NPC267605

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC278902 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1024
0.2-0.3	3811
0.3-0.4	3481
0.4-0.5	624
0.5-0.6	52
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
0.5668	Remote Similarity	NPD2299	Phase 1

Structure

NPC278902 OpenBabel07101718282D 24 24 0 0 1 0 0 0 0 0999 V2000 -2.9190 -1.0084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2248 -1.3685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9895 2.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2679 4.6026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8916 1.6681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6837 2.6463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1485 0.9990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4269 3.3154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9680 -0.6994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1974 1.3080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2189 4.2936 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7601 0.2788 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4543 0.6389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9621 4.9627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9402 5.1706 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -7.6312 4.2195 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -6.7542 5.9408 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5032 0.9479 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.6622 -0.3393 0.0000 O 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 12 2 0 0 0 0 8 13 1 0 0 0 0 9 10 2 0 0 0 0 9 21 1 0 0 0 0 10 24 1 0 0 0 0 12 15 1 0 0 0 0 13 4 1 1 0 0 0 13 17 1 0 0 0 0 14 11 1 6 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 22 2 3 0 0 0 15 23 1 0 0 0 0 16 21 2 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44627702
ChEMBL	CHEMBL1088458
ZINC

Physicochemical Properties

Molecular Weight:	408.06
ALogP:	4.1854
MLogP:	2.56
XLogP:	5.697
# Rotatable Bonds:	16
Polar Surface Area:	73.72
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	24

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