NPASS Natural Product

Natural Product: NPC134593

Natural Product ID:	NPC134593
Common Name:	Lehualide D
IUPAC Name:	2,3-dimethoxy-5-methyl-6-[(E)-3-methyl-12-sulfanyldodec-2-enyl]pyran-4-one
Synonyms:	Lehualide D
Molecular Formula:	C21H34O4S
Standard InCHIKey:	DHJSSVXNRTUOIN-DTQAZKPQSA-N
Standard InCHI:	InChI=1S/C21H34O4S/c1-16(12-10-8-6-5-7-9-11-15-26)13-14-18-17(2)19(22)20(23-3)21(24-4)25-18/h13,26H,5-12,14-15H2,1-4H3/b16-13+
Canonical SMILES:	SCCCCCCCCC/C(=C/Cc1oc(OC)c(c(=O)c1C)OC)/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
GI50	2
LD50	1

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT140	Organism	Artemia	Artemia	LD50	=	15	ug/ml	19691309
NPT2	Others	Unspecified		GI50	=	730	nM	19785389
NPT111	Cell Line	K562	Homo sapiens	GI50	=	230	nM	19785389

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 NPC134593 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	77
0.1-0.2	1470
0.2-0.3	9168
0.3-0.4	13601
0.4-0.5	5817
0.5-0.6	708
0.6-0.7	41
0.7-0.8	6
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	NPC66365
0.7313	Intermediate Similarity	NPC200831
0.7313	Intermediate Similarity	NPC224103
0.7313	Intermediate Similarity	NPC299369
0.7123	Intermediate Similarity	NPC474619
0.7121	Intermediate Similarity	NPC317796
0.7083	Intermediate Similarity	NPC98897
0.6986	Remote Similarity	NPC16119
0.6944	Remote Similarity	NPC474400
0.6944	Remote Similarity	NPC34622
0.6923	Remote Similarity	NPC22329
0.6842	Remote Similarity	NPC291062
0.6842	Remote Similarity	NPC94743
0.6806	Remote Similarity	NPC57463
0.6806	Remote Similarity	NPC151728
0.68	Remote Similarity	NPC263382
0.68	Remote Similarity	NPC134385
0.68	Remote Similarity	NPC125578
0.68	Remote Similarity	NPC146376
0.6769	Remote Similarity	NPC220191
0.6753	Remote Similarity	NPC474539
0.6716	Remote Similarity	NPC474805
0.6711	Remote Similarity	NPC262673
0.6667	Remote Similarity	NPC243272
0.6625	Remote Similarity	NPC261732
0.6622	Remote Similarity	NPC7940
0.662	Remote Similarity	NPC473494
0.6618	Remote Similarity	NPC129710
0.6582	Remote Similarity	NPC264178
0.6543	Remote Similarity	NPC47069
0.6494	Remote Similarity	NPC94488
0.6479	Remote Similarity	NPC139056
0.6375	Remote Similarity	NPC147438
0.6341	Remote Similarity	NPC471225
0.6333	Remote Similarity	NPC108026
0.6296	Remote Similarity	NPC315552
0.6267	Remote Similarity	NPC7029
0.625	Remote Similarity	NPC316851
0.622	Remote Similarity	NPC26504
0.6133	Remote Similarity	NPC53109
0.6133	Remote Similarity	NPC477830
0.6133	Remote Similarity	NPC143168
0.6053	Remote Similarity	NPC475618
0.6053	Remote Similarity	NPC477457
0.6053	Remote Similarity	NPC477456
0.6026	Remote Similarity	NPC298249
0.6	Remote Similarity	NPC168521
0.6	Remote Similarity	NPC106547
0.5974	Remote Similarity	NPC471556
0.5952	Remote Similarity	NPC473536
0.5909	Remote Similarity	NPC191337
0.5909	Remote Similarity	NPC110396
0.5909	Remote Similarity	NPC288281
0.5867	Remote Similarity	NPC79756
0.5857	Remote Similarity	NPC137396
0.5833	Remote Similarity	NPC477708
0.5823	Remote Similarity	NPC203335
0.5823	Remote Similarity	NPC251429
0.5821	Remote Similarity	NPC8610
0.5821	Remote Similarity	NPC262558
0.5814	Remote Similarity	NPC471740
0.5811	Remote Similarity	NPC320421
0.5797	Remote Similarity	NPC288381
0.5797	Remote Similarity	NPC20934
0.5778	Remote Similarity	NPC67081
0.5778	Remote Similarity	NPC471223
0.5778	Remote Similarity	NPC77971
0.5765	Remote Similarity	NPC283087
0.5758	Remote Similarity	NPC477686
0.5753	Remote Similarity	NPC221763
0.5714	Remote Similarity	NPC477458
0.5714	Remote Similarity	NPC291712
0.5714	Remote Similarity	NPC477707
0.5699	Remote Similarity	NPC50070
0.5699	Remote Similarity	NPC142159
0.5699	Remote Similarity	NPC95364
0.5694	Remote Similarity	NPC478120
0.5684	Remote Similarity	NPC248193
0.5684	Remote Similarity	NPC189651
0.5684	Remote Similarity	NPC475098
0.5682	Remote Similarity	NPC475833
0.5682	Remote Similarity	NPC286229
0.5682	Remote Similarity	NPC99308
0.5682	Remote Similarity	NPC280367
0.5682	Remote Similarity	NPC474085
0.5676	Remote Similarity	NPC283502
0.5658	Remote Similarity	NPC143857
0.5658	Remote Similarity	NPC229252
0.5652	Remote Similarity	NPC471739
0.5647	Remote Similarity	NPC16279
0.5647	Remote Similarity	NPC205615
0.5647	Remote Similarity	NPC256640
0.5625	Remote Similarity	NPC473213
0.5618	Remote Similarity	NPC10080
0.5618	Remote Similarity	NPC123908
0.5616	Remote Similarity	NPC317548
0.561	Remote Similarity	NPC477455
0.561	Remote Similarity	NPC469660
0.561	Remote Similarity	NPC315285
0.5606	Remote Similarity	NPC301972
0.5604	Remote Similarity	NPC263997
0.5604	Remote Similarity	NPC471060
0.5604	Remote Similarity	NPC8518
0.5604	Remote Similarity	NPC241512
0.5604	Remote Similarity	NPC6185
0.5604	Remote Similarity	NPC132228
0.5604	Remote Similarity	NPC281172

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC134593 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	94
0.1-0.2	2107
0.2-0.3	5227
0.3-0.4	1355
0.4-0.5	341
0.5-0.6	32
0.6-0.7	4
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
0.7313	Intermediate Similarity	NPD8779	Phase 3
0.6986	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4756	Discovery
0.6316	Remote Similarity	NPD3704	Approved
0.6133	Remote Similarity	NPD2664	Clinical (unspecified phase)

Structure

NPC134593 OpenBabel07101719162D 26 26 0 0 0 0 0 0 0 0999 V2000 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -5.0000 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 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 1.0000 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 -0.0000 1.0000 0.0000 C 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 0.8660 2.5000 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 9.5263 -4.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 6 1 0 0 0 0 5 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 15 1 0 0 0 0 12 16 1 0 0 0 0 13 14 1 0 0 0 0 13 16 2 0 0 0 0 14 18 1 0 0 0 0 15 26 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 22 2 0 0 0 0 20 21 2 0 0 0 0 20 23 1 0 0 0 0 21 24 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	11596094
ChEMBL	CHEMBL463506
ZINC

Physicochemical Properties

Molecular Weight:	382.22
ALogP:	-0.4782
MLogP:	3.22
XLogP:	6.681
# Rotatable Bonds:	18
Polar Surface Area:	83.56
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	26

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