NPASS Natural Product

Natural Product: NPC116231

Natural Product ID:	NPC116231
Common Name:	Antidesmone
IUPAC Name:	(5S)-3-methoxy-2-methyl-5-octyl-1,5,6,7-tetrahydroquinoline-4,8-dione
Synonyms:
Molecular Formula:	C19H29NO3
Standard InCHIKey:	SJWGGIJOUKBIPF-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C19H29NO3/c1-4-5-6-7-8-9-10-14-11-12-15(21)17-16(14)18(22)19(23-3)13(2)20-17/h14H,4-12H2,1-3H3,(H,20,22)/t14-/m0/s1
Canonical SMILES:	CCCCCCCC[C@H]1CCC(=O)c2c1c(=O)c(c([nH]2)C)OC
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
NPO22669	Waltheria indica	Species	Malvaceae	Eukaryota	roots			PMID[25314007]

Biological Activity

Activity Type	# Activity
IC50	5
MIC	10
Others	1

Activity Type	# Activity
Cell Line	2
Organism	12
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	23.4	ug/ml	PubChem BioAssay data set
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	14300	nM	25768703
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	170	nM	10543879
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	=	16	ug/ml	21714538
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	32	ug/ml	9873597
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	184300	nM	22341572
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	>	32	ug/ml	10217734
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	16	ug/ml	17536856
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	32	ug/ml	PubChem BioAssay data set
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	>	100000	nM	26331426
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	32	ug/ml	24974343
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	=	4	ug/ml	23268606
NPT2	Others	Unspecified		MIC	>	32	ug/ml	23268606
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	32	ug/ml	19456120
NPT186	Organism	Candida tropicalis	Candida tropicalis	MIC	>	32	ug/ml	9599274
NPT2	Others	Unspecified		Ratio IC50	=	1084.3		19029328

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 NPC116231 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	56
0.1-0.2	528
0.2-0.3	5329
0.3-0.4	16998
0.4-0.5	6824
0.5-0.6	1088
0.6-0.7	61
0.7-0.8	2
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9756	High Similarity	NPC472161
0.8837	High Similarity	NPC472136
0.8696	High Similarity	NPC472162
0.7917	Intermediate Similarity	NPC472167
0.7917	Intermediate Similarity	NPC472166
0.699	Remote Similarity	NPC34193
0.6786	Remote Similarity	NPC472164
0.6739	Remote Similarity	NPC23778
0.6636	Remote Similarity	NPC87919
0.663	Remote Similarity	NPC283087
0.6606	Remote Similarity	NPC24596
0.66	Remote Similarity	NPC236322
0.6574	Remote Similarity	NPC185929
0.6526	Remote Similarity	NPC474085
0.6486	Remote Similarity	NPC72688
0.646	Remote Similarity	NPC5485
0.6429	Remote Similarity	NPC475614
0.6395	Remote Similarity	NPC34622
0.6395	Remote Similarity	NPC474400
0.6392	Remote Similarity	NPC8091
0.6348	Remote Similarity	NPC7905
0.6348	Remote Similarity	NPC315652
0.6322	Remote Similarity	NPC98897
0.6316	Remote Similarity	NPC475681
0.6293	Remote Similarity	NPC27413
0.6293	Remote Similarity	NPC59751
0.6293	Remote Similarity	NPC271621
0.6279	Remote Similarity	NPC57463
0.6279	Remote Similarity	NPC151728
0.6263	Remote Similarity	NPC133652
0.6263	Remote Similarity	NPC6185
0.6263	Remote Similarity	NPC241512
0.6263	Remote Similarity	NPC8518
0.6263	Remote Similarity	NPC132228
0.6263	Remote Similarity	NPC263997
0.6261	Remote Similarity	NPC176336
0.625	Remote Similarity	NPC16119
0.6239	Remote Similarity	NPC296361
0.6238	Remote Similarity	NPC318578
0.6216	Remote Similarity	NPC176773
0.618	Remote Similarity	NPC243272
0.618	Remote Similarity	NPC474619
0.6179	Remote Similarity	NPC472165
0.617	Remote Similarity	NPC92080
0.616	Remote Similarity	NPC315011
0.6147	Remote Similarity	NPC251884
0.6134	Remote Similarity	NPC473808
0.6134	Remote Similarity	NPC315110
0.6117	Remote Similarity	NPC223093
0.6111	Remote Similarity	NPC263382
0.6111	Remote Similarity	NPC134385
0.6111	Remote Similarity	NPC125578
0.6111	Remote Similarity	NPC146376
0.61	Remote Similarity	NPC90287
0.6087	Remote Similarity	NPC474539
0.6083	Remote Similarity	NPC315915
0.6064	Remote Similarity	NPC175079
0.6061	Remote Similarity	NPC471595
0.6044	Remote Similarity	NPC94488
0.6044	Remote Similarity	NPC262673
0.6042	Remote Similarity	NPC30321
0.604	Remote Similarity	NPC203795
0.6036	Remote Similarity	NPC9436
0.602	Remote Similarity	NPC312419
0.602	Remote Similarity	NPC478262
0.6	Remote Similarity	NPC26504
0.5978	Remote Similarity	NPC94743
0.5978	Remote Similarity	NPC291062
0.5978	Remote Similarity	NPC173321
0.5962	Remote Similarity	NPC475823
0.5962	Remote Similarity	NPC474209
0.5957	Remote Similarity	NPC264178
0.5957	Remote Similarity	NPC147438
0.5941	Remote Similarity	NPC474680
0.5941	Remote Similarity	NPC76283
0.5941	Remote Similarity	NPC478245
0.5941	Remote Similarity	NPC2640
0.593	Remote Similarity	NPC473494
0.5922	Remote Similarity	NPC53454
0.5918	Remote Similarity	NPC108955
0.5905	Remote Similarity	NPC166110
0.5893	Remote Similarity	NPC133420
0.5882	Remote Similarity	NPC322672
0.5876	Remote Similarity	NPC469996
0.5876	Remote Similarity	NPC478247
0.5876	Remote Similarity	NPC478246
0.5876	Remote Similarity	NPC476808
0.5865	Remote Similarity	NPC280833
0.5859	Remote Similarity	NPC474353
0.5859	Remote Similarity	NPC225515
0.5859	Remote Similarity	NPC99308
0.5859	Remote Similarity	NPC55869
0.5849	Remote Similarity	NPC248193
0.584	Remote Similarity	NPC473249
0.5825	Remote Similarity	NPC473525
0.5816	Remote Similarity	NPC192329
0.5816	Remote Similarity	NPC476177
0.58	Remote Similarity	NPC103486
0.5784	Remote Similarity	NPC319913
0.5778	Remote Similarity	NPC61473
0.5773	Remote Similarity	NPC472300
0.5769	Remote Similarity	NPC478261
0.5769	Remote Similarity	NPC475001
0.5769	Remote Similarity	NPC478260
0.5769	Remote Similarity	NPC478259
0.5769	Remote Similarity	NPC307298
0.5769	Remote Similarity	NPC185059
0.5758	Remote Similarity	NPC18955
0.5755	Remote Similarity	NPC248913
0.5743	Remote Similarity	NPC288281
0.5743	Remote Similarity	NPC105803
0.5741	Remote Similarity	NPC31021
0.5739	Remote Similarity	NPC220730
0.5738	Remote Similarity	NPC13351
0.5738	Remote Similarity	NPC139867
0.573	Remote Similarity	NPC477830
0.573	Remote Similarity	NPC143168
0.573	Remote Similarity	NPC53109
0.5714	Remote Similarity	NPC58200
0.5714	Remote Similarity	NPC473955
0.5714	Remote Similarity	NPC142159
0.5714	Remote Similarity	NPC95364
0.5702	Remote Similarity	NPC233256
0.5702	Remote Similarity	NPC195841
0.57	Remote Similarity	NPC149237
0.57	Remote Similarity	NPC475833
0.5686	Remote Similarity	NPC60951
0.5686	Remote Similarity	NPC474359
0.5673	Remote Similarity	NPC220930
0.5673	Remote Similarity	NPC272039
0.567	Remote Similarity	NPC40353
0.567	Remote Similarity	NPC110725
0.567	Remote Similarity	NPC470525
0.5667	Remote Similarity	NPC7029
0.566	Remote Similarity	NPC478258
0.566	Remote Similarity	NPC113393
0.566	Remote Similarity	NPC478257
0.5657	Remote Similarity	NPC276647
0.5657	Remote Similarity	NPC27817
0.5657	Remote Similarity	NPC268502
0.5657	Remote Similarity	NPC622
0.5657	Remote Similarity	NPC254996
0.5648	Remote Similarity	NPC212812
0.5644	Remote Similarity	NPC321289
0.5644	Remote Similarity	NPC327969
0.5644	Remote Similarity	NPC473810
0.5631	Remote Similarity	NPC32037
0.5631	Remote Similarity	NPC470177
0.5625	Remote Similarity	NPC470299
0.5625	Remote Similarity	NPC77703
0.5625	Remote Similarity	NPC119326
0.562	Remote Similarity	NPC316325
0.5614	Remote Similarity	NPC472616
0.5607	Remote Similarity	NPC193396
0.5607	Remote Similarity	NPC470036
0.5607	Remote Similarity	NPC26865
0.5607	Remote Similarity	NPC174167
0.5607	Remote Similarity	NPC32944
0.5603	Remote Similarity	NPC470535
0.56	Remote Similarity	NPC474956
0.56	Remote Similarity	NPC2482
0.56	Remote Similarity	NPC250632
0.56	Remote Similarity	NPC304795

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC116231 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	74
0.1-0.2	456
0.2-0.3	3280
0.3-0.4	4310
0.4-0.5	919
0.5-0.6	114
0.6-0.7	8
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
0.6696	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3704	Approved
0.616	Remote Similarity	NPD2101	Approved
0.6134	Remote Similarity	NPD7196	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD7623	Phase 3
0.6033	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4695	Discontinued
0.59	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD3617	Approved
0.5862	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.584	Remote Similarity	NPD7746	Phase 1
0.584	Remote Similarity	NPD7747	Phase 1
0.5778	Remote Similarity	NPD7341	Phase 2
0.5738	Remote Similarity	NPD1689	Approved
0.573	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD2132	Phase 3
0.562	Remote Similarity	NPD7500	Approved
0.5619	Remote Similarity	NPD5737	Approved
0.5619	Remote Similarity	NPD6672	Approved
0.5612	Remote Similarity	NPD4756	Discovery

Structure

NPC116231 OpenBabel07101718182D 23 24 0 0 1 0 0 0 0 0999 V2000 -0.8660 -6.5000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0000 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 -0.8660 -3.5000 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 -2.0000 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 -0.5000 0.0000 C 0 0 1 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 0.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 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 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 13 1 0 0 0 0 3 23 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 10 1 1 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 21 2 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	6426678
ChEMBL	CHEMBL3342756
ZINC

Physicochemical Properties

Molecular Weight:	319.21
ALogP:	-2.5975
MLogP:	3.11
XLogP:	5.704
# Rotatable Bonds:	11
Polar Surface Area:	55.4
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	23

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General Info & Identifiers & Properties
Structure MOL file
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Biological Activities
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