NPASS Compound

Structure

NPC260474 OpenBabel07101719242D 23 25 0 0 1 0 0 0 0 0999 V2000 3.4641 -0.0000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -1.7321 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0000 -3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 14 2 0 0 0 0 7 19 1 0 0 0 0 8 9 2 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 20 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 1 0 0 0 16 18 1 0 0 0 0 17 22 2 0 0 0 0 18 23 2 0 0 0 0 19 20 1 1 0 0 0 19 21 1 0 0 0 0 20 3 1 1 0 0 0 21 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.21
Volume:	350.501
LogP:	4.04
LogD:	3.766
LogS:	-4.916
# Rotatable Bonds:	2
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.541
Synthetic Accessibility Score:	4.25
Fsp3:	0.619
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.618
MDCK Permeability:	2.3404090825351886e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	97.1021957397461%
Volume Distribution (VD):	2.467
Pgp-substrate:	4.114358901977539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.802
CYP1A2-substrate:	0.502
CYP2C19-inhibitor:	0.725
CYP2C19-substrate:	0.85
CYP2C9-inhibitor:	0.502
CYP2C9-substrate:	0.088
CYP2D6-inhibitor:	0.782
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.846
CYP3A4-substrate:	0.403

ADMET: Excretion

Clearance (CL):	8.87
Half-life (T1/2):	0.407

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.639
Drug-inuced Liver Injury (DILI):	0.181
AMES Toxicity:	0.1
Rat Oral Acute Toxicity:	0.555
Maximum Recommended Daily Dose:	0.878
Skin Sensitization:	0.968
Carcinogencity:	0.797
Eye Corrosion:	0.916
Eye Irritation:	0.892
Respiratory Toxicity:	0.977

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC260474

Natural Product ID:	NPC260474
*Common Name:**	Avarone
IUPAC Name:	2-[[(1R,2S,4aS,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl]cyclohexa-2,5-diene-1,4-dione
Synonyms:	Avarone; Avrone
Standard InCHIKey:	VPRHEJGLNUDEEH-LWILDLIXSA-N
Standard InCHI:	InChI=1S/C21H28O2/c1-14-6-5-7-19-20(14,3)11-10-15(2)21(19,4)13-16-12-17(22)8-9-18(16)23/h6,8-9,12,15,19H,5,7,10-11,13H2,1-4H3/t15-,19+,20+,21+/m0/s1
SMILES:	CC1=CCC[C@@H]2[C@]1(C)CC[C@H](C)[C@@]2(C)CC1=CC(=O)C=CC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464645
PubChem CID:	72186
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002802] Prenylquinones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO5563	Dysidea avara	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jo00050a043]
NPO26203	Dysidea villosa	Species	Dysideidae	Eukaryota	n.a.	Hainan, China	n.a.	PMID[19091557]
NPO5563	Dysidea avara	Species	Dysideidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[24547794]
NPO5563	Dysidea avara	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2778453]
NPO5563	Dysidea avara	Species	Dysideidae	Eukaryota	n.a.	Bay of Naples, Italy	n.a.	PMID[7714539]
NPO26203	Dysidea villosa	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	23
MIC	16
Others	27

Activity Type	# Activity
Cell Line	36
CELL-LINE	2
Individual Protein	1
NON-MOLECULAR	3
Organism	21
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	3200.0	nM	PMID[568961]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	6400.0	nM	PMID[568961]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	6400.0	nM	PMID[568961]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	6400.0	nM	PMID[568961]
NPT168	Cell Line	P388	Mus musculus	IC50	=	3100.0	nM	PMID[568962]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	6000.0	nM	PMID[568962]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	6000.0	nM	PMID[568962]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	6000.0	nM	PMID[568962]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	MIC	=	1.0	ug	PMID[568966]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	4900.0	nM	PMID[568967]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	26800.0	nM	PMID[568967]
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	4800.0	nM	PMID[568967]
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	4500.0	nM	PMID[568967]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	30030.0	nM	PMID[568968]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	18120.0	nM	PMID[568968]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	17080.0	nM	PMID[568968]
NPT2488	Cell Line	MDA-MB-453	Homo sapiens	IC50	=	16710.0	nM	PMID[568968]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	200000.0	nM	PMID[568968]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	24000.0	nM	PMID[568969]
NPT941	Cell Line	HaCaT	Homo sapiens	IC30	=	16.0	uM	PMID[568969]
NPT941	Cell Line	HaCaT	Homo sapiens	IC50	=	37000.0	nM	PMID[568969]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC30	=	36.0	uM	PMID[568969]
NPT397	Cell Line	NCI-H460	Homo sapiens	Selectivity ratio	<=	1.5	n.a.	PMID[568969]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	74.0	%	PMID[568969]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	3.4	%	PMID[568969]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	16.3	%	PMID[568969]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	6.3	%	PMID[568969]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	65.8	%	PMID[568969]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	2.6	%	PMID[568969]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	22.7	%	PMID[568969]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	8.9	%	PMID[568969]
NPT941	Cell Line	HaCaT	Homo sapiens	Activity	=	78.3	%	PMID[568969]
NPT941	Cell Line	HaCaT	Homo sapiens	Activity	=	2.5	%	PMID[568969]
NPT941	Cell Line	HaCaT	Homo sapiens	Activity	=	10.1	%	PMID[568969]
NPT941	Cell Line	HaCaT	Homo sapiens	Activity	=	9.1	%	PMID[568969]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	84000.0	nM	PMID[568969]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC30	=	10.0	uM	PMID[568969]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	63.0	%	PMID[568963]
NPT140	Organism	Artemia	Artemia	LC50	=	0.14	ppm	PMID[568963]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.56	ug.mL-1	PMID[568963]
NPT140	Organism	Artemia	Artemia	LC50	=	0.14	ppm	PMID[568964]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	63.0	%	PMID[568964]
NPT22	Organism	Bacillus subtilis subsp. spizizenii	Bacillus subtilis subsp. spizizenii	MIC	=	10.0	ug.mL-1	PMID[568966]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	1.0	ug.mL-1	PMID[568966]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	0.14	ppm	PMID[568966]
NPT1	Others	Radical scavenging activity		IC50	=	32100.0	nM	PMID[568966]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	23900.0	nM	PMID[568967]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.25	ug.mL-1	PMID[568967]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	25.0	ug.mL-1	PMID[568967]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	0.14	ppm	PMID[568967]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	40330.0	nM	PMID[568968]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	40060.0	nM	PMID[568968]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	=	20030.0	nM	PMID[568968]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	80130.0	nM	PMID[568968]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	2000380.0	nM	PMID[568968]
NPT3888	Organism	Micrococcus flavus	Micrococcus flavus	MIC	=	20030.0	nM	PMID[568968]
NPT1824	Organism	Clostridium sporogenes	Clostridium sporogenes	MIC	=	20030.0	nM	PMID[568968]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	440960.0	nM	PMID[568968]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	27560.0	nM	PMID[568968]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	=	55120.0	nM	PMID[568968]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	13780.0	nM	PMID[568968]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	170.0	ppm	PMID[568968]
NPT27	Others	Unspecified		Selectivity ratio	<=	1.5	n.a.	PMID[568969]
NPT20972	CELL-LINE	SU.86.86	Homo sapiens	Activity	>	20.0	%	PMID[568970]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC260474 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	237
0.1-0.2	1930
0.2-0.3	10638
0.3-0.4	15117
0.4-0.5	8109
0.5-0.6	4609
0.6-0.7	1618
0.7-0.8	348
0.8-0.85	66
0.85-0.9	21
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC188292
0.9688	High Similarity	NPC87141
0.9524	High Similarity	NPC251118
0.9385	High Similarity	NPC310992
0.9254	High Similarity	NPC54123
0.9242	High Similarity	NPC256846
0.9206	High Similarity	NPC288253
0.9118	High Similarity	NPC470045
0.9118	High Similarity	NPC470044
0.9104	High Similarity	NPC251929
0.9104	High Similarity	NPC265782
0.9104	High Similarity	NPC2634
0.9062	High Similarity	NPC469662
0.9	High Similarity	NPC1254
0.8955	High Similarity	NPC139397
0.8906	High Similarity	NPC197238
0.8906	High Similarity	NPC202118
0.8889	High Similarity	NPC127582
0.8841	High Similarity	NPC251705
0.8841	High Similarity	NPC303613
0.8841	High Similarity	NPC474228
0.8824	High Similarity	NPC260040
0.8824	High Similarity	NPC307176
0.8806	High Similarity	NPC155198
0.8769	High Similarity	NPC285371
0.8769	High Similarity	NPC475124
0.8732	High Similarity	NPC69408
0.873	High Similarity	NPC472304
0.873	High Similarity	NPC276764
0.8714	High Similarity	NPC309852
0.8696	High Similarity	NPC190035
0.8696	High Similarity	NPC234707
0.8696	High Similarity	NPC305501
0.8696	High Similarity	NPC115023
0.8696	High Similarity	NPC5701
0.8696	High Similarity	NPC225467
0.8592	High Similarity	NPC476346
0.8592	High Similarity	NPC293803
0.8592	High Similarity	NPC473171
0.8571	High Similarity	NPC27610
0.8571	High Similarity	NPC56905
0.8571	High Similarity	NPC311852
0.8551	High Similarity	NPC159577
0.8551	High Similarity	NPC282593
0.8551	High Similarity	NPC35734
0.8507	High Similarity	NPC323005
0.8493	Intermediate Similarity	NPC189485
0.8485	Intermediate Similarity	NPC212210
0.8462	Intermediate Similarity	NPC60565
0.8451	Intermediate Similarity	NPC474797
0.8451	Intermediate Similarity	NPC255021
0.8451	Intermediate Similarity	NPC474796
0.8451	Intermediate Similarity	NPC219232
0.8451	Intermediate Similarity	NPC329866
0.8451	Intermediate Similarity	NPC128346
0.8429	Intermediate Similarity	NPC474562
0.8429	Intermediate Similarity	NPC181204
0.8413	Intermediate Similarity	NPC115385
0.8406	Intermediate Similarity	NPC286814
0.8406	Intermediate Similarity	NPC182815
0.84	Intermediate Similarity	NPC475833
0.8382	Intermediate Similarity	NPC290350
0.8382	Intermediate Similarity	NPC4370
0.8378	Intermediate Similarity	NPC170793
0.8378	Intermediate Similarity	NPC27817
0.8378	Intermediate Similarity	NPC90965
0.8333	Intermediate Similarity	NPC255650
0.831	Intermediate Similarity	NPC130016
0.831	Intermediate Similarity	NPC180015
0.831	Intermediate Similarity	NPC109576
0.831	Intermediate Similarity	NPC56747
0.8281	Intermediate Similarity	NPC60772
0.8267	Intermediate Similarity	NPC108955
0.8267	Intermediate Similarity	NPC474509
0.8267	Intermediate Similarity	NPC476809
0.8261	Intermediate Similarity	NPC82477
0.8261	Intermediate Similarity	NPC39157
0.8261	Intermediate Similarity	NPC142754
0.8261	Intermediate Similarity	NPC296697
0.8261	Intermediate Similarity	NPC20610
0.8243	Intermediate Similarity	NPC115515
0.8235	Intermediate Similarity	NPC92327
0.8219	Intermediate Similarity	NPC469796
0.8219	Intermediate Similarity	NPC469793
0.8209	Intermediate Similarity	NPC4638
0.8209	Intermediate Similarity	NPC6697
0.8194	Intermediate Similarity	NPC211641
0.8182	Intermediate Similarity	NPC213152
0.8169	Intermediate Similarity	NPC223187
0.8169	Intermediate Similarity	NPC470078
0.8158	Intermediate Similarity	NPC99308
0.8158	Intermediate Similarity	NPC474085
0.8158	Intermediate Similarity	NPC55869
0.8158	Intermediate Similarity	NPC116797
0.8116	Intermediate Similarity	NPC475523
0.8116	Intermediate Similarity	NPC193770
0.8116	Intermediate Similarity	NPC176107
0.8116	Intermediate Similarity	NPC220210
0.8116	Intermediate Similarity	NPC20181
0.8108	Intermediate Similarity	NPC472300
0.8095	Intermediate Similarity	NPC200258
0.8088	Intermediate Similarity	NPC470329
0.8082	Intermediate Similarity	NPC65650
0.806	Intermediate Similarity	NPC165695
0.8056	Intermediate Similarity	NPC474488
0.8052	Intermediate Similarity	NPC142253
0.8052	Intermediate Similarity	NPC3511
0.8028	Intermediate Similarity	NPC40574
0.8026	Intermediate Similarity	NPC26139
0.8	Intermediate Similarity	NPC170799
0.8	Intermediate Similarity	NPC74410
0.8	Intermediate Similarity	NPC471409
0.8	Intermediate Similarity	NPC308108
0.8	Intermediate Similarity	NPC469996
0.8	Intermediate Similarity	NPC275494
0.7975	Intermediate Similarity	NPC474537
0.7973	Intermediate Similarity	NPC180886
0.7973	Intermediate Similarity	NPC110725
0.7971	Intermediate Similarity	NPC176171
0.7945	Intermediate Similarity	NPC20025
0.7937	Intermediate Similarity	NPC5626
0.7922	Intermediate Similarity	NPC225515
0.7922	Intermediate Similarity	NPC278459
0.7917	Intermediate Similarity	NPC21944
0.7917	Intermediate Similarity	NPC133253
0.7895	Intermediate Similarity	NPC472490
0.7895	Intermediate Similarity	NPC476177
0.7879	Intermediate Similarity	NPC259261
0.7867	Intermediate Similarity	NPC165711
0.7848	Intermediate Similarity	NPC87552
0.7846	Intermediate Similarity	NPC192427
0.7821	Intermediate Similarity	NPC238991
0.7821	Intermediate Similarity	NPC302661
0.7821	Intermediate Similarity	NPC472239
0.7821	Intermediate Similarity	NPC103486
0.7821	Intermediate Similarity	NPC472867
0.7794	Intermediate Similarity	NPC32285
0.7792	Intermediate Similarity	NPC2482
0.7792	Intermediate Similarity	NPC472478
0.7792	Intermediate Similarity	NPC469637
0.7792	Intermediate Similarity	NPC287063
0.7778	Intermediate Similarity	NPC14002
0.7778	Intermediate Similarity	NPC214770
0.7778	Intermediate Similarity	NPC246722
0.7778	Intermediate Similarity	NPC477856
0.7778	Intermediate Similarity	NPC151045
0.7778	Intermediate Similarity	NPC23117
0.7778	Intermediate Similarity	NPC268564
0.7763	Intermediate Similarity	NPC82635
0.7763	Intermediate Similarity	NPC470052
0.7761	Intermediate Similarity	NPC25853
0.775	Intermediate Similarity	NPC29447
0.775	Intermediate Similarity	NPC8518
0.775	Intermediate Similarity	NPC133652
0.775	Intermediate Similarity	NPC263997
0.775	Intermediate Similarity	NPC132228
0.775	Intermediate Similarity	NPC8571
0.775	Intermediate Similarity	NPC476426
0.775	Intermediate Similarity	NPC33663
0.7733	Intermediate Similarity	NPC40353
0.7733	Intermediate Similarity	NPC92080
0.7733	Intermediate Similarity	NPC474463
0.7733	Intermediate Similarity	NPC470525
0.7733	Intermediate Similarity	NPC19907
0.7727	Intermediate Similarity	NPC266295
0.7727	Intermediate Similarity	NPC30215
0.7727	Intermediate Similarity	NPC94991
0.7722	Intermediate Similarity	NPC118423
0.7722	Intermediate Similarity	NPC41539
0.7722	Intermediate Similarity	NPC53733
0.7722	Intermediate Similarity	NPC49019
0.7703	Intermediate Similarity	NPC251970
0.7703	Intermediate Similarity	NPC476046
0.7703	Intermediate Similarity	NPC241854
0.7692	Intermediate Similarity	NPC473217
0.7692	Intermediate Similarity	NPC149237
0.7692	Intermediate Similarity	NPC121984
0.7692	Intermediate Similarity	NPC470034
0.7692	Intermediate Similarity	NPC475863
0.7692	Intermediate Similarity	NPC471898
0.7681	Intermediate Similarity	NPC52449
0.7681	Intermediate Similarity	NPC169275
0.7654	Intermediate Similarity	NPC222613
0.7654	Intermediate Similarity	NPC118648
0.7654	Intermediate Similarity	NPC475022
0.7647	Intermediate Similarity	NPC97322
0.7647	Intermediate Similarity	NPC475795
0.7639	Intermediate Similarity	NPC477857
0.7632	Intermediate Similarity	NPC91665
0.7632	Intermediate Similarity	NPC257666
0.7632	Intermediate Similarity	NPC266193
0.7632	Intermediate Similarity	NPC97377
0.7625	Intermediate Similarity	NPC473246
0.7612	Intermediate Similarity	NPC96551
0.7612	Intermediate Similarity	NPC285594
0.76	Intermediate Similarity	NPC279666
0.76	Intermediate Similarity	NPC192540
0.7595	Intermediate Similarity	NPC469805
0.7595	Intermediate Similarity	NPC193347
0.7595	Intermediate Similarity	NPC469799

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC260474 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	2138
0.2-0.3	4333
0.3-0.4	1765
0.4-0.5	370
0.5-0.6	200
0.6-0.7	96
0.7-0.8	21
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9104	High Similarity	NPD4691	Approved
0.8986	High Similarity	NPD4058	Approved
0.8986	High Similarity	NPD4687	Approved
0.8955	High Similarity	NPD4137	Phase 3
0.8824	High Similarity	NPD4747	Approved
0.8714	High Similarity	NPD5733	Approved
0.8696	High Similarity	NPD5276	Approved
0.8261	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD287	Approved
0.7922	Intermediate Similarity	NPD8028	Phase 2
0.7875	Intermediate Similarity	NPD5690	Phase 2
0.7792	Intermediate Similarity	NPD4695	Discontinued
0.7595	Intermediate Similarity	NPD4221	Approved
0.7595	Intermediate Similarity	NPD4223	Phase 3
0.7561	Intermediate Similarity	NPD3573	Approved
0.7439	Intermediate Similarity	NPD4519	Discontinued
0.7439	Intermediate Similarity	NPD4694	Approved
0.7439	Intermediate Similarity	NPD5280	Approved
0.7439	Intermediate Similarity	NPD4623	Approved
0.7407	Intermediate Similarity	NPD3665	Phase 1
0.7407	Intermediate Similarity	NPD3133	Approved
0.7407	Intermediate Similarity	NPD4197	Approved
0.7407	Intermediate Similarity	NPD3666	Approved
0.7317	Intermediate Similarity	NPD5329	Approved
0.7308	Intermediate Similarity	NPD3617	Approved
0.7294	Intermediate Similarity	NPD5207	Approved
0.7229	Intermediate Similarity	NPD4690	Approved
0.7229	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5279	Phase 3
0.7229	Intermediate Similarity	NPD7334	Approved
0.7229	Intermediate Similarity	NPD7146	Approved
0.7229	Intermediate Similarity	NPD5330	Approved
0.7229	Intermediate Similarity	NPD6409	Approved
0.7229	Intermediate Similarity	NPD3618	Phase 1
0.7229	Intermediate Similarity	NPD5205	Approved
0.7229	Intermediate Similarity	NPD4138	Approved
0.7229	Intermediate Similarity	NPD4688	Approved
0.7229	Intermediate Similarity	NPD4689	Approved
0.7229	Intermediate Similarity	NPD7521	Approved
0.7229	Intermediate Similarity	NPD4693	Phase 3
0.7229	Intermediate Similarity	NPD6684	Approved
0.7215	Intermediate Similarity	NPD4195	Approved
0.7209	Intermediate Similarity	NPD5284	Approved
0.7209	Intermediate Similarity	NPD6079	Approved
0.7209	Intermediate Similarity	NPD5694	Approved
0.7209	Intermediate Similarity	NPD5281	Approved
0.716	Intermediate Similarity	NPD3667	Approved
0.7093	Intermediate Similarity	NPD5692	Phase 3
0.7059	Intermediate Similarity	NPD6672	Approved
0.7059	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6903	Approved
0.7059	Intermediate Similarity	NPD5208	Approved
0.7059	Intermediate Similarity	NPD5737	Approved
0.7011	Intermediate Similarity	NPD6050	Approved
0.6988	Remote Similarity	NPD4786	Approved
0.6988	Remote Similarity	NPD3668	Phase 3
0.6977	Remote Similarity	NPD4753	Phase 2
0.6977	Remote Similarity	NPD6904	Approved
0.6977	Remote Similarity	NPD6080	Approved
0.6977	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5328	Approved
0.6977	Remote Similarity	NPD6673	Approved
0.6966	Remote Similarity	NPD5210	Approved
0.6966	Remote Similarity	NPD4629	Approved
0.6897	Remote Similarity	NPD4096	Approved
0.6889	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5222	Approved
0.6889	Remote Similarity	NPD5221	Approved
0.686	Remote Similarity	NPD4518	Approved
0.6829	Remote Similarity	NPD4139	Approved
0.6829	Remote Similarity	NPD4692	Approved
0.6824	Remote Similarity	NPD6098	Approved
0.6818	Remote Similarity	NPD7515	Phase 2
0.6818	Remote Similarity	NPD5693	Phase 1
0.6813	Remote Similarity	NPD3495	Discontinued
0.6813	Remote Similarity	NPD5173	Approved
0.6778	Remote Similarity	NPD5695	Phase 3
0.6757	Remote Similarity	NPD7331	Phase 2
0.6747	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5133	Approved
0.6742	Remote Similarity	NPD4202	Approved
0.6707	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD1694	Approved
0.6703	Remote Similarity	NPD7614	Phase 1
0.6703	Remote Similarity	NPD7732	Phase 3
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7748	Approved
0.6596	Remote Similarity	NPD5223	Approved
0.6593	Remote Similarity	NPD5654	Approved
0.6593	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7631	Approved
0.6526	Remote Similarity	NPD5091	Approved
0.6526	Remote Similarity	NPD5224	Approved
0.6526	Remote Similarity	NPD5225	Approved
0.6526	Remote Similarity	NPD4633	Approved
0.6526	Remote Similarity	NPD5226	Approved
0.6526	Remote Similarity	NPD5211	Phase 2
0.6522	Remote Similarity	NPD4697	Phase 3
0.6471	Remote Similarity	NPD4788	Approved
0.6458	Remote Similarity	NPD5174	Approved
0.6458	Remote Similarity	NPD5175	Approved
0.6452	Remote Similarity	NPD5959	Approved
0.6452	Remote Similarity	NPD7902	Approved
0.6452	Remote Similarity	NPD6084	Phase 2
0.6452	Remote Similarity	NPD4755	Approved
0.6452	Remote Similarity	NPD6083	Phase 2
0.6444	Remote Similarity	NPD7609	Phase 3
0.6438	Remote Similarity	NPD4191	Approved
0.6438	Remote Similarity	NPD4194	Approved
0.6438	Remote Similarity	NPD4193	Approved
0.6438	Remote Similarity	NPD4192	Approved
0.64	Remote Similarity	NPD7341	Phase 2
0.6392	Remote Similarity	NPD5141	Approved
0.6383	Remote Similarity	NPD5696	Approved
0.6374	Remote Similarity	NPD6399	Phase 3
0.6316	Remote Similarity	NPD4700	Approved
0.6316	Remote Similarity	NPD6404	Discontinued
0.6316	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6614	Approved
0.6263	Remote Similarity	NPD5697	Approved
0.6224	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5168	Approved
0.62	Remote Similarity	NPD4729	Approved
0.62	Remote Similarity	NPD6011	Approved
0.62	Remote Similarity	NPD4730	Approved
0.62	Remote Similarity	NPD6881	Approved
0.62	Remote Similarity	NPD6899	Approved
0.619	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.618	Remote Similarity	NPD650	Approved
0.6173	Remote Similarity	NPD4784	Approved
0.6173	Remote Similarity	NPD4785	Approved
0.6139	Remote Similarity	NPD6012	Approved
0.6139	Remote Similarity	NPD6014	Approved
0.6139	Remote Similarity	NPD6013	Approved
0.6133	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD4243	Approved
0.6122	Remote Similarity	NPD6052	Approved
0.6122	Remote Similarity	NPD4754	Approved
0.6119	Remote Similarity	NPD8262	Approved
0.6098	Remote Similarity	NPD8039	Approved
0.6087	Remote Similarity	NPD6411	Approved
0.6078	Remote Similarity	NPD5250	Approved
0.6078	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5249	Phase 3
0.6078	Remote Similarity	NPD5248	Approved
0.6078	Remote Similarity	NPD4634	Approved
0.6078	Remote Similarity	NPD7290	Approved
0.6078	Remote Similarity	NPD7102	Approved
0.6078	Remote Similarity	NPD5135	Approved
0.6078	Remote Similarity	NPD5169	Approved
0.6078	Remote Similarity	NPD5251	Approved
0.6078	Remote Similarity	NPD6883	Approved
0.6078	Remote Similarity	NPD5247	Approved
0.6056	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5128	Approved
0.6024	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5215	Approved
0.6019	Remote Similarity	NPD5216	Approved
0.6019	Remote Similarity	NPD6650	Approved
0.6019	Remote Similarity	NPD5127	Approved
0.6019	Remote Similarity	NPD6869	Approved
0.6019	Remote Similarity	NPD8130	Phase 1
0.6019	Remote Similarity	NPD6847	Approved
0.6019	Remote Similarity	NPD6649	Approved
0.6019	Remote Similarity	NPD5217	Approved
0.6019	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD4767	Approved
0.5962	Remote Similarity	NPD6882	Approved
0.5962	Remote Similarity	NPD8297	Approved
0.5957	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD1696	Phase 3
0.5941	Remote Similarity	NPD5701	Approved
0.5941	Remote Similarity	NPD6412	Phase 2
0.5905	Remote Similarity	NPD4632	Approved
0.5904	Remote Similarity	NPD8264	Approved
0.5904	Remote Similarity	NPD5275	Approved
0.5904	Remote Similarity	NPD7339	Approved
0.5904	Remote Similarity	NPD6942	Approved
0.5904	Remote Similarity	NPD4190	Phase 3
0.5882	Remote Similarity	NPD7320	Approved
0.5882	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD5290	Discontinued
0.587	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.587	Remote Similarity	NPD6101	Approved
0.5849	Remote Similarity	NPD5167	Approved
0.5844	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD6373	Approved
0.5825	Remote Similarity	NPD6372	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data