NPASS Natural Product

Natural Product: NPC66365

Natural Product ID:	NPC66365
Common Name:	Lehualide C
IUPAC Name:	S-[(E)-12-(5,6-dimethoxy-3-methyl-4-oxopyran-2-yl)-10-methyldodec-10-enyl] ethanethioate
Synonyms:	Lehualide C
Molecular Formula:	C23H36O5S
Standard InCHIKey:	JETGOHMWHVGCPY-SAPNQHFASA-N
Standard InCHI:	InChI=1S/C23H36O5S/c1-17(13-11-9-7-6-8-10-12-16-29-19(3)24)14-15-20-18(2)21(25)22(26-4)23(27-5)28-20/h14H,6-13,15-16H2,1-5H3/b17-14+
Canonical SMILES:	COc1oc(C/C=C(/CCCCCCCCCSC(=O)C)C)c(c(=O)c1OC)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
NPO31509	Plakortis	Genus	Plakinidae	Eukaryota		Hawaiian		PMID[16180823]

Biological Activity

Activity Type	# Activity
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT140	Organism	Artemia	Artemia	LD50	=	15	ug/ml	24818517

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 NPC66365 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	79
0.1-0.2	1600
0.2-0.3	10370
0.3-0.4	13340
0.4-0.5	5028
0.5-0.6	432
0.6-0.7	34
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9254	High Similarity	NPC134593
0.7125	Intermediate Similarity	NPC47069
0.7	Intermediate Similarity	NPC224103
0.7	Intermediate Similarity	NPC261732
0.7	Intermediate Similarity	NPC299369
0.7	Intermediate Similarity	NPC200831
0.6842	Remote Similarity	NPC474619
0.6812	Remote Similarity	NPC317796
0.68	Remote Similarity	NPC98897
0.6711	Remote Similarity	NPC16119
0.6667	Remote Similarity	NPC474400
0.6667	Remote Similarity	NPC34622
0.6618	Remote Similarity	NPC22329
0.6582	Remote Similarity	NPC291062
0.6582	Remote Similarity	NPC94743
0.6538	Remote Similarity	NPC146376
0.6538	Remote Similarity	NPC134385
0.6538	Remote Similarity	NPC263382
0.6538	Remote Similarity	NPC125578
0.6533	Remote Similarity	NPC151728
0.6533	Remote Similarity	NPC57463
0.65	Remote Similarity	NPC474539
0.6471	Remote Similarity	NPC220191
0.6456	Remote Similarity	NPC262673
0.6429	Remote Similarity	NPC474805
0.641	Remote Similarity	NPC243272
0.6364	Remote Similarity	NPC7940
0.6351	Remote Similarity	NPC473494
0.6341	Remote Similarity	NPC264178
0.6338	Remote Similarity	NPC129710
0.625	Remote Similarity	NPC94488
0.625	Remote Similarity	NPC317548
0.6216	Remote Similarity	NPC139056
0.6145	Remote Similarity	NPC147438
0.6129	Remote Similarity	NPC108026
0.6118	Remote Similarity	NPC471225
0.6071	Remote Similarity	NPC315552
0.6026	Remote Similarity	NPC7029
0.6024	Remote Similarity	NPC316851
0.6	Remote Similarity	NPC26504
0.5897	Remote Similarity	NPC477830
0.5897	Remote Similarity	NPC143168
0.5897	Remote Similarity	NPC53109
0.5823	Remote Similarity	NPC477457
0.5823	Remote Similarity	NPC475618
0.5823	Remote Similarity	NPC477456
0.5802	Remote Similarity	NPC298249
0.5753	Remote Similarity	NPC168521
0.575	Remote Similarity	NPC471556
0.5747	Remote Similarity	NPC473536
0.5735	Remote Similarity	NPC106547
0.5714	Remote Similarity	NPC288281
0.5652	Remote Similarity	NPC191337
0.5652	Remote Similarity	NPC110396
0.5641	Remote Similarity	NPC79756
0.5632	Remote Similarity	NPC477708
0.5618	Remote Similarity	NPC471740
0.5616	Remote Similarity	NPC137396
0.5616	Remote Similarity	NPC477779
0.561	Remote Similarity	NPC203335
0.561	Remote Similarity	NPC251429

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC66365 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	102
0.1-0.2	2142
0.2-0.3	5161
0.3-0.4	1418
0.4-0.5	313
0.5-0.6	21
0.6-0.7	3
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
0.7	Intermediate Similarity	NPD8779	Phase 3
0.6711	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD4756	Discovery
0.6076	Remote Similarity	NPD3704	Approved
0.5897	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.587	Remote Similarity	NPD6422	Discontinued

Structure

NPC66365 OpenBabel07101718182D 29 29 0 0 0 0 0 0 0 0999 V2000 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 0.0000 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 0.8660 -11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 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 1.7321 -12.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -10.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 14 17 2 0 0 0 0 15 20 1 0 0 0 0 16 29 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 19 24 2 0 0 0 0 19 29 1 0 0 0 0 20 28 1 0 0 0 0 21 22 1 0 0 0 0 21 25 2 0 0 0 0 22 23 2 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	11604251
ChEMBL	CHEMBL463505
ZINC

Physicochemical Properties

Molecular Weight:	424.23
ALogP:	-0.5122
MLogP:	3.33
XLogP:	6.435
# Rotatable Bonds:	20
Polar Surface Area:	87.13
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	29

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