NPASS Compound

Structure

CID235539 OpenBabel06191716032D 35 39 0 0 1 0 0 0 0 0999 V2000 4.1956 -0.4188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8732 3.9974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1503 0.0237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3142 1.0509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0252 0.5705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3435 0.0635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7211 2.5287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1773 3.0183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3982 0.8945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8732 3.0183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2558 0.4220 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0252 2.5287 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7211 1.5496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3294 2.5287 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2348 1.1267 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7872 1.5103 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2820 -0.0339 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8732 1.0601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8317 2.1814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1773 1.0601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4830 1.5248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3351 1.0425 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0252 1.5496 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3294 1.5496 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9737 0.1023 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5690 1.0601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0357 -0.9815 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8732 0.0809 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7401 2.5469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4746 2.5039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8174 1.8946 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8523 -0.3298 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 0.3348 2.6346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6393 1.0280 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 10 1 0 0 0 0 6 22 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 33 1 0 0 0 0 10 12 1 0 0 0 0 11 3 1 1 0 0 0 11 15 1 0 0 0 0 11 17 1 0 0 0 0 12 23 1 6 0 0 0 13 18 1 0 0 0 0 13 26 2 0 0 0 0 14 24 1 1 0 0 0 14 34 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 1 0 0 0 16 19 1 0 0 0 0 16 35 1 6 0 0 0 17 25 1 1 0 0 0 17 27 1 0 0 0 0 18 23 1 6 0 0 0 18 28 1 0 0 0 0 19 29 2 0 0 0 0 19 34 1 0 0 0 0 20 23 1 6 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 30 2 0 0 0 0 21 35 1 0 0 0 0 22 4 1 6 0 0 0 22 31 1 0 0 0 0 23 5 1 6 0 0 0 24 9 1 6 0 0 0 25 32 1 6 0 0 0 25 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.22
Volume:	475.53
LogP:	1.528
LogD:	0.852
LogS:	-4.049
# Rotatable Bonds:	4
TPSA:	156.66
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.364
Synthetic Accessibility Score:	6.743
Fsp3:	0.84
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.383
MDCK Permeability:	7.320521399378777e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.347
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.052
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.51
Plasma Protein Binding (PPB):	39.00489807128906%
Volume Distribution (VD):	0.508
Pgp-substrate:	46.816104888916016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.967
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.495
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.375
CYP3A4-substrate:	0.253

ADMET: Excretion

Clearance (CL):	2.722
Half-life (T1/2):	0.167

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.372
Drug-inuced Liver Injury (DILI):	0.756
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.308
Maximum Recommended Daily Dose:	0.093
Skin Sensitization:	0.183
Carcinogencity:	0.097
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.67

Download Data

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

Natural Product: NPC235539

Natural Product ID:	NPC235539
*Common Name:**	Glaucarubinone
IUPAC Name:	n.a.
Synonyms:	NSC-14975
Standard InCHIKey:	WRBGCYVAJRRQKP-STDAJNJZSA-N
Standard InCHI:	InChI=1S/C25H34O10/c1-6-22(4,31)21(30)35-16-15-11(3)17(27)25(32)20-23(5)12(10(2)7-13(26)18(23)28)8-14(34-19(16)29)24(15,20)9-33-25/h7,11-12,14-18,20,27-28,31-32H,6,8-9H2,1-5H3/t11-,12+,14-,15-,16-,17-,18-,20-,22+,23-,24+,25+/m1/s1
SMILES:	CC[C@@](C(=O)O[C@H]1C(=O)O[C@H]2[C@]34[C@@H]1[C@@H](C)[C@@H](O)[C@@]([C@@H]4[C@@]1([C@@H](C2)C(=CC(=O)[C@H]1O)C)C)(OC3)O)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458347
PubChem CID:	441796
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO32507	odyendyea gabonensis	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20738103]
NPO4432	0thospondias staudtii	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21733691]
NPO6324	Soulamea tomentosa	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264678]
NPO30695	Allanthus excelsa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4432	0thospondias staudtii	Species	Simaroubaceae	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
EC50	3
ED50	4
GI50	75
IC50	5
Others	5

Activity Type	# Activity
Cell Line	82
Individual Protein	3
NON-MOLECULAR	4
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	500.0	nM	PMID[512757]
NPT116	Cell Line	HL-60	Homo sapiens	EC50	=	1800.0	nM	PMID[512757]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	1000.0	nM	PMID[512757]
NPT116	Cell Line	HL-60	Homo sapiens	Ratio IC50	=	2.1	n.a.	PMID[512757]
NPT168	Cell Line	P388	Mus musculus	T/C	=	231.0	%	PMID[512758]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	270.0	nM	PMID[512760]
NPT90	Cell Line	DU-145	Homo sapiens	ED50	=	0.47	uM	PMID[512762]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.88	uM	PMID[512762]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.44	uM	PMID[512762]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	424.62	nM	PMID[512764]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	157.76	nM	PMID[512764]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	292.42	nM	PMID[512764]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	79.62	nM	PMID[512764]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	377.57	nM	PMID[512764]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	48.98	nM	PMID[512764]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	50.0	nM	PMID[512764]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	824.14	nM	PMID[512764]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	44.16	nM	PMID[512764]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	50.0	nM	PMID[512764]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	50.0	nM	PMID[512764]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	50.0	nM	PMID[512764]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	319.89	nM	PMID[512764]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	98.17	nM	PMID[512764]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	50.0	nM	PMID[512764]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	79.43	nM	PMID[512764]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	2269.86	nM	PMID[512764]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	50.0	nM	PMID[512764]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	75.34	nM	PMID[512764]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	657.66	nM	PMID[512764]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	50.0	nM	PMID[512764]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	946.24	nM	PMID[512764]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	93.33	nM	PMID[512764]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	45.29	nM	PMID[512764]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	389.94	nM	PMID[512764]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	50.0	nM	PMID[512764]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	74.99	nM	PMID[512764]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	60.39	nM	PMID[512764]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	50.0	nM	PMID[512764]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	106.91	nM	PMID[512764]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	2123.24	nM	PMID[512764]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	54.2	nM	PMID[512764]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	54.83	nM	PMID[512764]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	320.63	nM	PMID[512764]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	35.4	nM	PMID[512764]
NPT168	Cell Line	P388	Mus musculus	GI50	n.a.	67.61	nM	PMID[512764]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	229.09	nM	PMID[512764]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	62.52	nM	PMID[512764]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	171.0	nM	PMID[512764]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	67.92	nM	PMID[512764]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	1213.39	nM	PMID[512764]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	58.48	nM	PMID[512764]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	88.51	nM	PMID[512764]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	50.0	nM	PMID[512764]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	66.07	nM	PMID[512764]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	54.45	nM	PMID[512764]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	458.14	nM	PMID[512764]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	198.61	nM	PMID[512764]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	1016.25	nM	PMID[512764]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	11.09	nM	PMID[512764]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	50.0	nM	PMID[512764]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	176.2	nM	PMID[512764]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	91.2	nM	PMID[512764]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	51.05	nM	PMID[512764]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	207.01	nM	PMID[512764]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	115.61	nM	PMID[512764]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	1396.37	nM	PMID[512764]
NPT552	Cell Line	P388/ADR	Mus musculus	GI50	n.a.	663.74	nM	PMID[512764]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	50.0	nM	PMID[512764]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	167.11	nM	PMID[512764]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	145.88	nM	PMID[512764]
NPT577	Cell Line	RXF 631	Homo sapiens	GI50	n.a.	543.25	nM	PMID[512764]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	67.45	nM	PMID[512764]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	66.83	nM	PMID[512764]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	50.47	nM	PMID[512764]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	50.0	nM	PMID[512764]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	238.78	nM	PMID[512764]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	113.24	nM	PMID[512764]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	50.0	nM	PMID[512764]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	50.0	nM	PMID[512764]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	814.7	nM	PMID[512764]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	252.93	nM	PMID[512764]
NPT738	Cell Line	SN12K1	Homo sapiens	GI50	n.a.	50.0	nM	PMID[512764]
NPT27	Others	Unspecified		Selectivity ratio	=	285.0	n.a.	PMID[512759]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	1800.0	nM	PMID[512760]
NPT2	Others	Unspecified		INH	=	0.29	uM	PMID[512760]
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	IC50	=	40.0	nM	PMID[512760]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	21000.0	nM	PMID[512761]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	<	25.0	%	PMID[512760]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.24	uM	PMID[512762]
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	EC50	=	130.0	nM	PMID[512763]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	0.168	ug.mL-1	PMID[512765]
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	EC50	=	1490.0	nM	PMID[512766]

☑ 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 NPC235539 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	246
0.1-0.2	1406
0.2-0.3	4423
0.3-0.4	8026
0.4-0.5	11894
0.5-0.6	6954
0.6-0.7	5321
0.7-0.8	3710
0.8-0.85	577
0.85-0.9	78
0.9-0.95	40
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC134869
1.0	High Similarity	NPC152199
0.9906	High Similarity	NPC18547
0.9906	High Similarity	NPC474906
0.9815	High Similarity	NPC297179
0.9717	High Similarity	NPC11252
0.9717	High Similarity	NPC289312
0.963	High Similarity	NPC40632
0.963	High Similarity	NPC251236
0.963	High Similarity	NPC328374
0.963	High Similarity	NPC96312
0.9623	High Similarity	NPC201992
0.9537	High Similarity	NPC473798
0.9459	High Similarity	NPC107338
0.9459	High Similarity	NPC109607
0.9455	High Similarity	NPC204552
0.9455	High Similarity	NPC188667
0.945	High Similarity	NPC474046
0.945	High Similarity	NPC470628
0.945	High Similarity	NPC259306
0.9444	High Similarity	NPC49451
0.9444	High Similarity	NPC51978
0.9369	High Similarity	NPC476529
0.9369	High Similarity	NPC475775
0.9358	High Similarity	NPC470919
0.9358	High Similarity	NPC469877
0.934	High Similarity	NPC293850
0.9298	High Similarity	NPC470922
0.9286	High Similarity	NPC112038
0.9279	High Similarity	NPC17772
0.9204	High Similarity	NPC102822
0.9204	High Similarity	NPC477046
0.9196	High Similarity	NPC469488
0.9189	High Similarity	NPC309433
0.9189	High Similarity	NPC470854
0.9189	High Similarity	NPC474654
0.9189	High Similarity	NPC287343
0.9189	High Similarity	NPC97908
0.9189	High Similarity	NPC122033
0.9174	High Similarity	NPC302146
0.9174	High Similarity	NPC474516
0.9099	High Similarity	NPC474734
0.9091	High Similarity	NPC7921
0.9091	High Similarity	NPC208998
0.9065	High Similarity	NPC3316
0.9065	High Similarity	NPC144854
0.9027	High Similarity	NPC470777
0.9018	High Similarity	NPC473968
0.9018	High Similarity	NPC473590
0.8981	High Similarity	NPC154608
0.8981	High Similarity	NPC192813
0.8981	High Similarity	NPC277017
0.8929	High Similarity	NPC16081
0.8929	High Similarity	NPC173686
0.8909	High Similarity	NPC171888
0.8909	High Similarity	NPC146945
0.8899	High Similarity	NPC472534
0.8899	High Similarity	NPC143706
0.8879	High Similarity	NPC227397
0.8879	High Similarity	NPC265557
0.8879	High Similarity	NPC91693
0.8879	High Similarity	NPC18945
0.8879	High Similarity	NPC67251
0.8879	High Similarity	NPC105926
0.8839	High Similarity	NPC45218
0.8839	High Similarity	NPC323821
0.8839	High Similarity	NPC268238
0.8839	High Similarity	NPC143268
0.8803	High Similarity	NPC24651
0.8803	High Similarity	NPC476729
0.8796	High Similarity	NPC102352
0.8793	High Similarity	NPC312833
0.8772	High Similarity	NPC251310
0.8772	High Similarity	NPC470776
0.8761	High Similarity	NPC207217
0.875	High Similarity	NPC255017
0.875	High Similarity	NPC194100
0.8739	High Similarity	NPC188291
0.8729	High Similarity	NPC285091
0.8727	High Similarity	NPC27814
0.8707	High Similarity	NPC275675
0.8707	High Similarity	NPC470779
0.8696	High Similarity	NPC473920
0.8696	High Similarity	NPC127530
0.8684	High Similarity	NPC470775
0.8684	High Similarity	NPC176513
0.8679	High Similarity	NPC472972
0.8678	High Similarity	NPC100390
0.8678	High Similarity	NPC254614
0.8673	High Similarity	NPC102088
0.8673	High Similarity	NPC243354
0.8661	High Similarity	NPC90769
0.8649	High Similarity	NPC474567
0.8649	High Similarity	NPC210005
0.8632	High Similarity	NPC471965
0.8624	High Similarity	NPC181357
0.8621	High Similarity	NPC471406
0.8584	High Similarity	NPC194273
0.8584	High Similarity	NPC293038
0.8584	High Similarity	NPC62696
0.8583	High Similarity	NPC295220
0.8583	High Similarity	NPC475636
0.8571	High Similarity	NPC471243
0.8571	High Similarity	NPC87662
0.8559	High Similarity	NPC262199
0.8559	High Similarity	NPC141350
0.8559	High Similarity	NPC202666
0.8559	High Similarity	NPC471964
0.8559	High Similarity	NPC478066
0.8559	High Similarity	NPC14617
0.8559	High Similarity	NPC471961
0.8547	High Similarity	NPC75417
0.8545	High Similarity	NPC293512
0.8534	High Similarity	NPC122971
0.8534	High Similarity	NPC319570
0.8534	High Similarity	NPC473401
0.8534	High Similarity	NPC279143
0.8532	High Similarity	NPC475036
0.8532	High Similarity	NPC65523
0.8525	High Similarity	NPC471855
0.8525	High Similarity	NPC102316
0.8512	High Similarity	NPC54614
0.8512	High Similarity	NPC309096
0.8509	High Similarity	NPC475633
0.85	High Similarity	NPC470780
0.8496	Intermediate Similarity	NPC472002
0.8496	Intermediate Similarity	NPC130427
0.8496	Intermediate Similarity	NPC471967
0.8496	Intermediate Similarity	NPC280782
0.8487	Intermediate Similarity	NPC247315
0.8487	Intermediate Similarity	NPC471962
0.8487	Intermediate Similarity	NPC177820
0.8487	Intermediate Similarity	NPC473255
0.8487	Intermediate Similarity	NPC471963
0.8487	Intermediate Similarity	NPC30188
0.8487	Intermediate Similarity	NPC470477
0.848	Intermediate Similarity	NPC596
0.8475	Intermediate Similarity	NPC249848
0.8475	Intermediate Similarity	NPC222688
0.8475	Intermediate Similarity	NPC40775
0.8475	Intermediate Similarity	NPC235438
0.8475	Intermediate Similarity	NPC107966
0.8468	Intermediate Similarity	NPC258323
0.8468	Intermediate Similarity	NPC262813
0.8468	Intermediate Similarity	NPC94942
0.8468	Intermediate Similarity	NPC473288
0.8468	Intermediate Similarity	NPC272576
0.8455	Intermediate Similarity	NPC478151
0.8448	Intermediate Similarity	NPC286347
0.8443	Intermediate Similarity	NPC134914
0.8443	Intermediate Similarity	NPC172374
0.8443	Intermediate Similarity	NPC264566
0.8443	Intermediate Similarity	NPC478064
0.8443	Intermediate Similarity	NPC478065
0.8443	Intermediate Similarity	NPC173435
0.8443	Intermediate Similarity	NPC301639
0.8443	Intermediate Similarity	NPC475167
0.8443	Intermediate Similarity	NPC475377
0.8443	Intermediate Similarity	NPC476074
0.8443	Intermediate Similarity	NPC329993
0.8443	Intermediate Similarity	NPC45346
0.8443	Intermediate Similarity	NPC262796
0.844	Intermediate Similarity	NPC275583
0.844	Intermediate Similarity	NPC474575
0.8435	Intermediate Similarity	NPC179626
0.8421	Intermediate Similarity	NPC320118
0.8421	Intermediate Similarity	NPC198539
0.8421	Intermediate Similarity	NPC271138
0.8421	Intermediate Similarity	NPC269315
0.8421	Intermediate Similarity	NPC178981
0.8417	Intermediate Similarity	NPC181066
0.8417	Intermediate Similarity	NPC174367
0.8417	Intermediate Similarity	NPC225049
0.8417	Intermediate Similarity	NPC469947
0.8417	Intermediate Similarity	NPC47113
0.8407	Intermediate Similarity	NPC263827
0.8407	Intermediate Similarity	NPC285410
0.8407	Intermediate Similarity	NPC250481
0.8403	Intermediate Similarity	NPC281148
0.8403	Intermediate Similarity	NPC30735
0.8403	Intermediate Similarity	NPC235405
0.84	Intermediate Similarity	NPC141215
0.84	Intermediate Similarity	NPC190065
0.84	Intermediate Similarity	NPC251998
0.84	Intermediate Similarity	NPC471089
0.8393	Intermediate Similarity	NPC218853
0.8393	Intermediate Similarity	NPC41405
0.8393	Intermediate Similarity	NPC474242
0.8393	Intermediate Similarity	NPC310546
0.839	Intermediate Similarity	NPC202051
0.8378	Intermediate Similarity	NPC230541
0.8376	Intermediate Similarity	NPC35405
0.8376	Intermediate Similarity	NPC39211
0.8376	Intermediate Similarity	NPC469945
0.8376	Intermediate Similarity	NPC11551
0.8376	Intermediate Similarity	NPC208381
0.8376	Intermediate Similarity	NPC473884
0.8376	Intermediate Similarity	NPC6377
0.8376	Intermediate Similarity	NPC192791
0.8376	Intermediate Similarity	NPC157868

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 NPC235539 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	1663
0.2-0.3	3840
0.3-0.4	2172
0.4-0.5	706
0.5-0.6	279
0.6-0.7	137
0.7-0.8	113
0.8-0.85	32
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8559	High Similarity	NPD8328	Phase 3
0.8333	Intermediate Similarity	NPD6882	Approved
0.8333	Intermediate Similarity	NPD8297	Approved
0.8333	Intermediate Similarity	NPD7492	Approved
0.8305	Intermediate Similarity	NPD6054	Approved
0.8305	Intermediate Similarity	NPD6319	Approved
0.8305	Intermediate Similarity	NPD6059	Approved
0.8288	Intermediate Similarity	NPD6675	Approved
0.8288	Intermediate Similarity	NPD7128	Approved
0.8288	Intermediate Similarity	NPD6402	Approved
0.8288	Intermediate Similarity	NPD5739	Approved
0.8279	Intermediate Similarity	NPD7736	Approved
0.8264	Intermediate Similarity	NPD6616	Approved
0.823	Intermediate Similarity	NPD6373	Approved
0.823	Intermediate Similarity	NPD6372	Approved
0.8205	Intermediate Similarity	NPD6009	Approved
0.8205	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8197	Intermediate Similarity	NPD7078	Approved
0.8197	Intermediate Similarity	NPD8293	Discontinued
0.8167	Intermediate Similarity	NPD6370	Approved
0.8142	Intermediate Similarity	NPD6881	Approved
0.8142	Intermediate Similarity	NPD7320	Approved
0.8142	Intermediate Similarity	NPD6899	Approved
0.8103	Intermediate Similarity	NPD4632	Approved
0.8087	Intermediate Similarity	NPD6649	Approved
0.8087	Intermediate Similarity	NPD6650	Approved
0.8083	Intermediate Similarity	NPD6016	Approved
0.8083	Intermediate Similarity	NPD6015	Approved
0.807	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8053	Intermediate Similarity	NPD6412	Phase 2
0.8053	Intermediate Similarity	NPD5697	Approved
0.8053	Intermediate Similarity	NPD5701	Approved
0.8017	Intermediate Similarity	NPD5988	Approved
0.8	Intermediate Similarity	NPD7102	Approved
0.8	Intermediate Similarity	NPD7290	Approved
0.8	Intermediate Similarity	NPD6883	Approved
0.7967	Intermediate Similarity	NPD7507	Approved
0.7931	Intermediate Similarity	NPD6617	Approved
0.7931	Intermediate Similarity	NPD6847	Approved
0.7931	Intermediate Similarity	NPD6869	Approved
0.7931	Intermediate Similarity	NPD8130	Phase 1
0.7913	Intermediate Similarity	NPD6014	Approved
0.7913	Intermediate Similarity	NPD6012	Approved
0.7913	Intermediate Similarity	NPD6013	Approved
0.7826	Intermediate Similarity	NPD6686	Approved
0.7826	Intermediate Similarity	NPD6011	Approved
0.7826	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7604	Phase 2
0.7787	Intermediate Similarity	NPD5983	Phase 2
0.7778	Intermediate Similarity	NPD7319	Approved
0.7778	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD6033	Approved
0.768	Intermediate Similarity	NPD6336	Discontinued
0.7658	Intermediate Similarity	NPD4755	Approved
0.7658	Intermediate Similarity	NPD6084	Phase 2
0.7658	Intermediate Similarity	NPD6083	Phase 2
0.7652	Intermediate Similarity	NPD6008	Approved
0.7607	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7748	Approved
0.7542	Intermediate Similarity	NPD4634	Approved
0.7523	Intermediate Similarity	NPD7515	Phase 2
0.7522	Intermediate Similarity	NPD5286	Approved
0.7522	Intermediate Similarity	NPD4700	Approved
0.7522	Intermediate Similarity	NPD4696	Approved
0.7522	Intermediate Similarity	NPD5285	Approved
0.7521	Intermediate Similarity	NPD6274	Approved
0.75	Intermediate Similarity	NPD7902	Approved
0.748	Intermediate Similarity	NPD7101	Approved
0.748	Intermediate Similarity	NPD7100	Approved
0.748	Intermediate Similarity	NPD7516	Approved
0.7459	Intermediate Similarity	NPD7115	Discovery
0.7398	Intermediate Similarity	NPD7327	Approved
0.7398	Intermediate Similarity	NPD7328	Approved
0.7398	Intermediate Similarity	NPD6335	Approved
0.7395	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4633	Approved
0.7391	Intermediate Similarity	NPD5224	Approved
0.7391	Intermediate Similarity	NPD5226	Approved
0.7391	Intermediate Similarity	NPD5225	Approved
0.7391	Intermediate Similarity	NPD5211	Phase 2
0.736	Intermediate Similarity	NPD8515	Approved
0.736	Intermediate Similarity	NPD6908	Approved
0.736	Intermediate Similarity	NPD8033	Approved
0.736	Intermediate Similarity	NPD8513	Phase 3
0.736	Intermediate Similarity	NPD8517	Approved
0.736	Intermediate Similarity	NPD8516	Approved
0.736	Intermediate Similarity	NPD6909	Approved
0.7355	Intermediate Similarity	NPD8133	Approved
0.735	Intermediate Similarity	NPD4767	Approved
0.735	Intermediate Similarity	NPD4768	Approved
0.7339	Intermediate Similarity	NPD5328	Approved
0.7328	Intermediate Similarity	NPD5174	Approved
0.7328	Intermediate Similarity	NPD5175	Approved
0.7321	Intermediate Similarity	NPD5695	Phase 3
0.7317	Intermediate Similarity	NPD6317	Approved
0.7315	Intermediate Similarity	NPD3573	Approved
0.7304	Intermediate Similarity	NPD5223	Approved
0.7297	Intermediate Similarity	NPD6399	Phase 3
0.7281	Intermediate Similarity	NPD7638	Approved
0.7281	Intermediate Similarity	NPD5696	Approved
0.728	Intermediate Similarity	NPD8377	Approved
0.728	Intermediate Similarity	NPD8294	Approved
0.7265	Intermediate Similarity	NPD5141	Approved
0.7258	Intermediate Similarity	NPD6313	Approved
0.7258	Intermediate Similarity	NPD6314	Approved
0.7257	Intermediate Similarity	NPD5222	Approved
0.7257	Intermediate Similarity	NPD4697	Phase 3
0.7257	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5221	Approved
0.7248	Intermediate Similarity	NPD6672	Approved
0.7248	Intermediate Similarity	NPD5737	Approved
0.7236	Intermediate Similarity	NPD6868	Approved
0.7232	Intermediate Similarity	NPD7900	Approved
0.7232	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD4730	Approved
0.7227	Intermediate Similarity	NPD4729	Approved
0.7222	Intermediate Similarity	NPD8379	Approved
0.7222	Intermediate Similarity	NPD8378	Approved
0.7222	Intermediate Similarity	NPD8296	Approved
0.7222	Intermediate Similarity	NPD6921	Approved
0.7222	Intermediate Similarity	NPD8380	Approved
0.7222	Intermediate Similarity	NPD8335	Approved
0.7222	Intermediate Similarity	NPD7503	Approved
0.7217	Intermediate Similarity	NPD7639	Approved
0.7217	Intermediate Similarity	NPD7640	Approved
0.7207	Intermediate Similarity	NPD6079	Approved
0.7193	Intermediate Similarity	NPD5173	Approved
0.719	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4754	Approved
0.7143	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD4225	Approved
0.7109	Intermediate Similarity	NPD6067	Discontinued
0.7107	Intermediate Similarity	NPD5247	Approved
0.7107	Intermediate Similarity	NPD5251	Approved
0.7107	Intermediate Similarity	NPD5248	Approved
0.7107	Intermediate Similarity	NPD5249	Phase 3
0.7107	Intermediate Similarity	NPD5250	Approved
0.7087	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5128	Approved
0.7064	Intermediate Similarity	NPD3618	Phase 1
0.7054	Intermediate Similarity	NPD6411	Approved
0.7027	Intermediate Similarity	NPD6673	Approved
0.7027	Intermediate Similarity	NPD4753	Phase 2
0.7027	Intermediate Similarity	NPD6080	Approved
0.7027	Intermediate Similarity	NPD6904	Approved
0.6991	Remote Similarity	NPD4202	Approved
0.6964	Remote Similarity	NPD6698	Approved
0.6964	Remote Similarity	NPD46	Approved
0.6947	Remote Similarity	NPD8074	Phase 3
0.6937	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5282	Discontinued
0.6917	Remote Similarity	NPD5956	Approved
0.6911	Remote Similarity	NPD5215	Approved
0.6911	Remote Similarity	NPD5216	Approved
0.6911	Remote Similarity	NPD5217	Approved
0.6909	Remote Similarity	NPD6684	Approved
0.6909	Remote Similarity	NPD7146	Approved
0.6909	Remote Similarity	NPD7334	Approved
0.6909	Remote Similarity	NPD6409	Approved
0.6909	Remote Similarity	NPD7521	Approved
0.6909	Remote Similarity	NPD5330	Approved
0.6881	Remote Similarity	NPD4786	Approved
0.6875	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6101	Approved
0.687	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7260	Phase 2
0.6855	Remote Similarity	NPD6053	Discontinued
0.6852	Remote Similarity	NPD3667	Approved
0.6833	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5169	Approved
0.6829	Remote Similarity	NPD5135	Approved
0.6786	Remote Similarity	NPD6903	Approved
0.6774	Remote Similarity	NPD5127	Approved
0.6757	Remote Similarity	NPD6098	Approved
0.6754	Remote Similarity	NPD8035	Phase 2
0.6754	Remote Similarity	NPD6050	Approved
0.6754	Remote Similarity	NPD8034	Phase 2
0.6754	Remote Similarity	NPD5693	Phase 1
0.6727	Remote Similarity	NPD3665	Phase 1
0.6727	Remote Similarity	NPD3666	Approved
0.6727	Remote Similarity	NPD3133	Approved
0.6724	Remote Similarity	NPD5210	Approved
0.6724	Remote Similarity	NPD4629	Approved
0.6723	Remote Similarity	NPD5344	Discontinued
0.6721	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5779	Approved
0.6696	Remote Similarity	NPD5778	Approved
0.6691	Remote Similarity	NPD6845	Suspended
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD5692	Phase 3
0.6667	Remote Similarity	NPD5168	Approved
0.6641	Remote Similarity	NPD8080	Discontinued
0.6614	Remote Similarity	NPD5167	Approved
0.6609	Remote Similarity	NPD5694	Approved
0.6609	Remote Similarity	NPD7983	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