NPASS Compound

Structure

NPC304194 OpenBabel07101719152D 38 42 0 0 1 0 0 0 0 0999 V2000 4.7238 0.9455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1149 1.4683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1997 -3.4539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 4.3953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5144 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0260 0.6192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0407 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 2.9302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 2.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4666 -1.7669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1404 -2.3574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7684 0.7424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7717 -3.3518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3835 3.9070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4666 -0.1865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6918 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6918 0.9767 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9767 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5377 2.4419 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5377 -0.4884 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5377 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 1.4651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8459 -0.4884 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 2.5377 -1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3458 -4.1420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2294 4.3953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1690 -2.4595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3835 2.9302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 2 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 8 32 1 0 0 0 0 10 11 1 0 0 0 0 10 25 1 0 0 0 0 11 27 1 0 0 0 0 12 17 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 26 1 0 0 0 0 14 15 1 0 0 0 0 14 28 1 0 0 0 0 15 31 1 0 0 0 0 16 33 1 0 0 0 0 17 34 1 0 0 0 0 18 19 1 0 0 0 0 18 32 1 0 0 0 0 19 34 1 0 0 0 0 20 37 1 0 0 0 0 22 35 2 0 0 0 0 22 37 1 0 0 0 0 23 36 2 0 0 0 0 23 38 1 0 0 0 0 24 21 1 6 0 0 0 24 29 1 0 0 0 0 25 29 1 0 0 0 0 25 32 1 6 0 0 0 26 30 1 0 0 0 0 26 31 1 1 0 0 0 27 31 1 1 0 0 0 27 33 1 0 0 0 0 28 30 1 0 0 0 0 28 38 1 1 0 0 0 29 34 1 1 0 0 0 31 7 1 1 0 0 0 32 33 1 1 0 0 0 33 9 1 1 0 0 0 34 20 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	526.4
Volume:	581.089
LogP:	7.048
LogD:	5.657
LogS:	-6.343
# Rotatable Bonds:	6
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.274
Synthetic Accessibility Score:	4.823
Fsp3:	0.882
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.168
MDCK Permeability:	3.531113179633394e-05
Pgp-inhibitor:	0.51
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.918

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	87.52257537841797%
Volume Distribution (VD):	1.3
Pgp-substrate:	2.4517977237701416%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.133
CYP2C19-inhibitor:	0.072
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.159
CYP2C9-substrate:	0.168
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.421
CYP3A4-inhibitor:	0.714
CYP3A4-substrate:	0.616

ADMET: Excretion

Clearance (CL):	3.019
Half-life (T1/2):	0.159

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.244
Drug-inuced Liver Injury (DILI):	0.457
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.72
Skin Sensitization:	0.332
Carcinogencity:	0.007
Eye Corrosion:	0.396
Eye Irritation:	0.674
Respiratory Toxicity:	0.58

Download Data

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

Natural Product: NPC304194

Natural Product ID:	NPC304194
*Common Name:**	Betulin Diacetate
IUPAC Name:	[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetyloxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl acetate
Synonyms:	Betulin 3,28-Diacetate; Betulin Diacetate
Standard InCHIKey:	MIROITGPMGDCGI-MQXQNARFSA-N
Standard InCHI:	InChI=1S/C34H54O4/c1-21(2)24-12-17-34(20-37-22(3)35)19-18-32(8)25(29(24)34)10-11-27-31(7)15-14-28(38-23(4)36)30(5,6)26(31)13-16-33(27,32)9/h24-29H,1,10-20H2,2-9H3/t24-,25+,26-,27+,28-,29+,31-,32+,33+,34+/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)OC(=O)C)[C@@H]12)COC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL359080
PubChem CID:	236415
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO1145	Coussarea paniculata	Species	Rubiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[12662105]
NPO1145	Coussarea paniculata	Species	Rubiaceae	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	19
ED50	2
GI50	66
IC50	6
Others	5

Activity Type	# Activity
Cell Line	84
Individual Protein	1
NON-MOLECULAR	4
Organism	5
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	>	189800.0	nM	PMID[539071]
NPT759	Cell Line	H9	Homo sapiens	EC50	>	189800.0	nM	PMID[539071]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>=	20.0	ug.mL-1	PMID[539072]
NPT319	Cell Line	B16	Mus musculus	ED50	=	3.4	uM	PMID[539073]
NPT319	Cell Line	B16	Mus musculus	IC50	=	36800.0	nM	PMID[539073]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	1.4	ug.mL-1	PMID[539075]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	31550.05	nM	PMID[539076]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	574.12	nM	PMID[539076]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	33113.11	nM	PMID[539076]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	500.03	nM	PMID[539076]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	3006.08	nM	PMID[539076]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	2147.83	nM	PMID[539076]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	6208.69	nM	PMID[539076]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	5058.25	nM	PMID[539076]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	2233.57	nM	PMID[539076]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	2152.78	nM	PMID[539076]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	857.04	nM	PMID[539076]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	1032.76	nM	PMID[539076]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	2648.5	nM	PMID[539076]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	760.33	nM	PMID[539076]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	2118.36	nM	PMID[539076]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	1963.36	nM	PMID[539076]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	2535.13	nM	PMID[539076]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	651.63	nM	PMID[539076]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	38.46	nM	PMID[539076]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[539076]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.806	ug ml-1	PMID[539078]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[539078]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[539078]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[539078]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[539078]
NPT179	Cell Line	A2780	Homo sapiens	EC50	>	30000.0	nM	PMID[539080]
NPT81	Cell Line	A549	Homo sapiens	EC50	>	30000.0	nM	PMID[539080]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	>	30000.0	nM	PMID[539080]
NPT179	Cell Line	A2780	Homo sapiens	EC50	=	20300.0	nM	PMID[539081]
NPT139	Cell Line	HT-29	Homo sapiens	EC50	=	25700.0	nM	PMID[539081]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	>	30000.0	nM	PMID[539081]
NPT81	Cell Line	A549	Homo sapiens	EC50	=	21500.0	nM	PMID[539081]
NPT165	Cell Line	HeLa	Homo sapiens	EC50	>	30000.0	nM	PMID[539081]
NPT1083	Cell Line	A-375	Homo sapiens	EC50	>	30000.0	nM	PMID[539082]
NPT139	Cell Line	HT-29	Homo sapiens	EC50	>	30000.0	nM	PMID[539082]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	>	30000.0	nM	PMID[539082]
NPT179	Cell Line	A2780	Homo sapiens	EC50	>	30000.0	nM	PMID[539082]
NPT1216	Cell Line	FaDu	Homo sapiens	EC50	>	30000.0	nM	PMID[539082]
NPT886	Cell Line	NIH3T3	Mus musculus	EC50	>	30000.0	nM	PMID[539082]
NPT27	Others	Unspecified		TI	<	1.0	n.a.	PMID[539071]
NPT856	Organism	Semliki forest virus	Semliki forest virus	Activity	=	21.0	%	PMID[539074]
NPT27	Others	Unspecified		Activity	=	97.0	%	PMID[539074]
NPT856	Organism	Semliki forest virus	Semliki forest virus	IC50	=	9100.0	nM	PMID[539074]
NPT856	Organism	Semliki forest virus	Semliki forest virus	IC50	=	9120.11	nM	PMID[539074]
NPT27	Others	Unspecified		pTI	=	0.0	n.a.	PMID[539077]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	189670.59	nM	PMID[539077]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	>	10.0	ug.mL-1	PMID[539078]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	<	50.0	%	PMID[539079]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	30000.0	nM	PMID[539080]
NPT27	Others	Unspecified		EC50	>	30000.0	nM	PMID[539080]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	30000.0	nM	PMID[539081]

☑ 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 NPC304194 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	198
0.1-0.2	2106
0.2-0.3	9970
0.3-0.4	14299
0.4-0.5	5881
0.5-0.6	4262
0.6-0.7	4701
0.7-0.8	1155
0.8-0.85	91
0.85-0.9	25
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9865	High Similarity	NPC305835
0.961	High Similarity	NPC473742
0.9367	High Similarity	NPC98270
0.9359	High Similarity	NPC5280
0.9342	High Similarity	NPC47808
0.925	High Similarity	NPC168231
0.9241	High Similarity	NPC475509
0.9241	High Similarity	NPC239362
0.9079	High Similarity	NPC84868
0.9024	High Similarity	NPC4309
0.8974	High Similarity	NPC206735
0.8875	High Similarity	NPC139206
0.875	High Similarity	NPC286786
0.8706	High Similarity	NPC471901
0.8706	High Similarity	NPC160506
0.8675	High Similarity	NPC33768
0.8642	High Similarity	NPC132386
0.8625	High Similarity	NPC290495
0.8625	High Similarity	NPC195334
0.8605	High Similarity	NPC471902
0.8605	High Similarity	NPC287118
0.8605	High Similarity	NPC473690
0.8554	High Similarity	NPC2783
0.8554	High Similarity	NPC12774
0.8537	High Similarity	NPC299963
0.8519	High Similarity	NPC472504
0.8488	Intermediate Similarity	NPC475416
0.8452	Intermediate Similarity	NPC264005
0.8452	Intermediate Similarity	NPC269360
0.8434	Intermediate Similarity	NPC294438
0.8434	Intermediate Similarity	NPC264317
0.8415	Intermediate Similarity	NPC471037
0.8395	Intermediate Similarity	NPC108476
0.8391	Intermediate Similarity	NPC473678
0.8375	Intermediate Similarity	NPC153987
0.8375	Intermediate Similarity	NPC44083
0.8353	Intermediate Similarity	NPC16377
0.8353	Intermediate Similarity	NPC474719
0.8333	Intermediate Similarity	NPC104387
0.8333	Intermediate Similarity	NPC240235
0.8333	Intermediate Similarity	NPC178383
0.8333	Intermediate Similarity	NPC212879
0.8333	Intermediate Similarity	NPC474970
0.8333	Intermediate Similarity	NPC231256
0.8256	Intermediate Similarity	NPC213832
0.8256	Intermediate Similarity	NPC57954
0.8256	Intermediate Similarity	NPC220498
0.8256	Intermediate Similarity	NPC271974
0.8256	Intermediate Similarity	NPC247312
0.825	Intermediate Similarity	NPC63020
0.8235	Intermediate Similarity	NPC162107
0.8235	Intermediate Similarity	NPC478104
0.8235	Intermediate Similarity	NPC46912
0.8228	Intermediate Similarity	NPC278091
0.8228	Intermediate Similarity	NPC86305
0.8228	Intermediate Similarity	NPC93662
0.8228	Intermediate Similarity	NPC14112
0.8228	Intermediate Similarity	NPC78067
0.8214	Intermediate Similarity	NPC191965
0.8205	Intermediate Similarity	NPC192638
0.8205	Intermediate Similarity	NPC62657
0.8205	Intermediate Similarity	NPC25511
0.8182	Intermediate Similarity	NPC475061
0.8161	Intermediate Similarity	NPC10274
0.8161	Intermediate Similarity	NPC169933
0.8161	Intermediate Similarity	NPC471896
0.8148	Intermediate Similarity	NPC220379
0.814	Intermediate Similarity	NPC471900
0.814	Intermediate Similarity	NPC160304
0.8132	Intermediate Similarity	NPC474092
0.8125	Intermediate Similarity	NPC212241
0.8125	Intermediate Similarity	NPC248830
0.8125	Intermediate Similarity	NPC119355
0.8125	Intermediate Similarity	NPC202540
0.8118	Intermediate Similarity	NPC471042
0.8118	Intermediate Similarity	NPC10005
0.8118	Intermediate Similarity	NPC329943
0.8118	Intermediate Similarity	NPC84121
0.8118	Intermediate Similarity	NPC9892
0.8118	Intermediate Similarity	NPC137306
0.8118	Intermediate Similarity	NPC91525
0.8111	Intermediate Similarity	NPC304899
0.8111	Intermediate Similarity	NPC475178
0.8111	Intermediate Similarity	NPC253115
0.809	Intermediate Similarity	NPC303863
0.8068	Intermediate Similarity	NPC219516
0.8049	Intermediate Similarity	NPC261616
0.8046	Intermediate Similarity	NPC471043
0.8046	Intermediate Similarity	NPC474889
0.8046	Intermediate Similarity	NPC475049
0.8025	Intermediate Similarity	NPC42853
0.8025	Intermediate Similarity	NPC102708
0.8	Intermediate Similarity	NPC279974
0.8	Intermediate Similarity	NPC474013
0.8	Intermediate Similarity	NPC474971
0.7978	Intermediate Similarity	NPC291373
0.7978	Intermediate Similarity	NPC244356
0.7978	Intermediate Similarity	NPC224060
0.7978	Intermediate Similarity	NPC38232
0.7976	Intermediate Similarity	NPC472743
0.7976	Intermediate Similarity	NPC170862
0.7976	Intermediate Similarity	NPC475726
0.7975	Intermediate Similarity	NPC272359
0.7955	Intermediate Similarity	NPC219937
0.7955	Intermediate Similarity	NPC111585
0.7955	Intermediate Similarity	NPC120840
0.7955	Intermediate Similarity	NPC194485
0.7955	Intermediate Similarity	NPC113989
0.7955	Intermediate Similarity	NPC123252
0.7955	Intermediate Similarity	NPC53890
0.7955	Intermediate Similarity	NPC148414
0.7955	Intermediate Similarity	NPC175628
0.7952	Intermediate Similarity	NPC73515
0.7949	Intermediate Similarity	NPC111234
0.7931	Intermediate Similarity	NPC473879
0.7931	Intermediate Similarity	NPC470613
0.7931	Intermediate Similarity	NPC144069
0.7931	Intermediate Similarity	NPC224145
0.7931	Intermediate Similarity	NPC470612
0.7927	Intermediate Similarity	NPC80297
0.7927	Intermediate Similarity	NPC116119
0.7927	Intermediate Similarity	NPC49627
0.7927	Intermediate Similarity	NPC472742
0.7927	Intermediate Similarity	NPC475727
0.7927	Intermediate Similarity	NPC471475
0.7927	Intermediate Similarity	NPC49599
0.7912	Intermediate Similarity	NPC299654
0.7912	Intermediate Similarity	NPC327788
0.7907	Intermediate Similarity	NPC264127
0.7907	Intermediate Similarity	NPC286153
0.7901	Intermediate Similarity	NPC212453
0.7889	Intermediate Similarity	NPC277399
0.7882	Intermediate Similarity	NPC474482
0.7882	Intermediate Similarity	NPC475745
0.7882	Intermediate Similarity	NPC264665
0.7882	Intermediate Similarity	NPC74595
0.7875	Intermediate Similarity	NPC200243
0.7875	Intermediate Similarity	NPC230704
0.7875	Intermediate Similarity	NPC70982
0.7875	Intermediate Similarity	NPC185536
0.7875	Intermediate Similarity	NPC478105
0.7875	Intermediate Similarity	NPC3403
0.7867	Intermediate Similarity	NPC474768
0.7865	Intermediate Similarity	NPC285184
0.7865	Intermediate Similarity	NPC60755
0.7865	Intermediate Similarity	NPC470230
0.7865	Intermediate Similarity	NPC177641
0.7865	Intermediate Similarity	NPC470590
0.7865	Intermediate Similarity	NPC26888
0.7865	Intermediate Similarity	NPC77099
0.7865	Intermediate Similarity	NPC130840
0.7849	Intermediate Similarity	NPC208358
0.7848	Intermediate Similarity	NPC279241
0.7841	Intermediate Similarity	NPC30522
0.7831	Intermediate Similarity	NPC475679
0.7831	Intermediate Similarity	NPC170038
0.7831	Intermediate Similarity	NPC269791
0.7826	Intermediate Similarity	NPC469810
0.7821	Intermediate Similarity	NPC45296
0.7805	Intermediate Similarity	NPC301707
0.7802	Intermediate Similarity	NPC205173
0.7791	Intermediate Similarity	NPC201655
0.7791	Intermediate Similarity	NPC292553
0.7791	Intermediate Similarity	NPC164424
0.7778	Intermediate Similarity	NPC86368
0.7778	Intermediate Similarity	NPC26046
0.7778	Intermediate Similarity	NPC91573
0.7778	Intermediate Similarity	NPC294263
0.7778	Intermediate Similarity	NPC92489
0.7778	Intermediate Similarity	NPC163902
0.7766	Intermediate Similarity	NPC155974
0.7753	Intermediate Similarity	NPC474728
0.7753	Intermediate Similarity	NPC302280
0.775	Intermediate Similarity	NPC475517
0.775	Intermediate Similarity	NPC49168
0.775	Intermediate Similarity	NPC474524
0.775	Intermediate Similarity	NPC5046
0.775	Intermediate Similarity	NPC74639
0.775	Intermediate Similarity	NPC254509
0.775	Intermediate Similarity	NPC308440
0.775	Intermediate Similarity	NPC472503
0.775	Intermediate Similarity	NPC196358
0.775	Intermediate Similarity	NPC145552
0.7742	Intermediate Similarity	NPC119036
0.7742	Intermediate Similarity	NPC300179
0.7742	Intermediate Similarity	NPC472028
0.7742	Intermediate Similarity	NPC102426
0.7727	Intermediate Similarity	NPC97884
0.7727	Intermediate Similarity	NPC472220
0.7727	Intermediate Similarity	NPC474845
0.7727	Intermediate Similarity	NPC146937
0.7717	Intermediate Similarity	NPC276103
0.7717	Intermediate Similarity	NPC54248
0.7711	Intermediate Similarity	NPC192744
0.7711	Intermediate Similarity	NPC477287
0.7711	Intermediate Similarity	NPC118987
0.7701	Intermediate Similarity	NPC472505
0.7701	Intermediate Similarity	NPC472738
0.7701	Intermediate Similarity	NPC98236
0.7701	Intermediate Similarity	NPC269396

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 NPC304194 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	2393
0.2-0.3	4455
0.3-0.4	1449
0.4-0.5	289
0.5-0.6	187
0.6-0.7	170
0.7-0.8	29
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8706	High Similarity	NPD8035	Phase 2
0.8706	High Similarity	NPD8034	Phase 2
0.8434	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7748	Approved
0.7692	Intermediate Similarity	NPD7900	Approved
0.7692	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7525	Registered
0.7528	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7902	Approved
0.7444	Intermediate Similarity	NPD6051	Approved
0.7391	Intermediate Similarity	NPD6399	Phase 3
0.7368	Intermediate Similarity	NPD7638	Approved
0.7349	Intermediate Similarity	NPD6117	Approved
0.7333	Intermediate Similarity	NPD6672	Approved
0.7333	Intermediate Similarity	NPD5737	Approved
0.7303	Intermediate Similarity	NPD6409	Approved
0.7303	Intermediate Similarity	NPD7521	Approved
0.7303	Intermediate Similarity	NPD6684	Approved
0.7303	Intermediate Similarity	NPD7334	Approved
0.7303	Intermediate Similarity	NPD7146	Approved
0.7303	Intermediate Similarity	NPD5330	Approved
0.7294	Intermediate Similarity	NPD7645	Phase 2
0.7292	Intermediate Similarity	NPD7639	Approved
0.7292	Intermediate Similarity	NPD7640	Approved
0.7283	Intermediate Similarity	NPD7515	Phase 2
0.7262	Intermediate Similarity	NPD6116	Phase 1
0.7176	Intermediate Similarity	NPD6118	Approved
0.7176	Intermediate Similarity	NPD6115	Approved
0.7176	Intermediate Similarity	NPD6697	Approved
0.7176	Intermediate Similarity	NPD6114	Approved
0.7143	Intermediate Similarity	NPD6903	Approved
0.7108	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5777	Approved
0.7053	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6942	Approved
0.7024	Intermediate Similarity	NPD7339	Approved
0.6931	Remote Similarity	NPD6675	Approved
0.6931	Remote Similarity	NPD6402	Approved
0.6931	Remote Similarity	NPD7128	Approved
0.6931	Remote Similarity	NPD5739	Approved
0.6923	Remote Similarity	NPD6098	Approved
0.6889	Remote Similarity	NPD4786	Approved
0.6882	Remote Similarity	NPD6080	Approved
0.6882	Remote Similarity	NPD5328	Approved
0.6882	Remote Similarity	NPD6673	Approved
0.6882	Remote Similarity	NPD6904	Approved
0.6829	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7632	Discontinued
0.6796	Remote Similarity	NPD6881	Approved
0.6796	Remote Similarity	NPD7320	Approved
0.6796	Remote Similarity	NPD6899	Approved
0.6778	Remote Similarity	NPD4788	Approved
0.6765	Remote Similarity	NPD6008	Approved
0.6762	Remote Similarity	NPD8130	Phase 1
0.6744	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3618	Phase 1
0.6737	Remote Similarity	NPD6079	Approved
0.6735	Remote Similarity	NPD6084	Phase 2
0.6735	Remote Similarity	NPD6083	Phase 2
0.6731	Remote Similarity	NPD6372	Approved
0.6731	Remote Similarity	NPD6373	Approved
0.6703	Remote Similarity	NPD3668	Phase 3
0.6699	Remote Similarity	NPD5697	Approved
0.6699	Remote Similarity	NPD5701	Approved
0.6698	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7102	Approved
0.6636	Remote Similarity	NPD8133	Approved
0.6635	Remote Similarity	NPD6011	Approved
0.6604	Remote Similarity	NPD6847	Approved
0.6604	Remote Similarity	NPD6617	Approved
0.6604	Remote Similarity	NPD6869	Approved
0.6604	Remote Similarity	NPD6649	Approved
0.6604	Remote Similarity	NPD6650	Approved
0.6604	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6001	Approved
0.6596	Remote Similarity	NPD5208	Approved
0.6577	Remote Similarity	NPD8294	Approved
0.6577	Remote Similarity	NPD8377	Approved
0.6571	Remote Similarity	NPD6013	Approved
0.6571	Remote Similarity	NPD6012	Approved
0.6571	Remote Similarity	NPD6014	Approved
0.6562	Remote Similarity	NPD5693	Phase 1
0.6562	Remote Similarity	NPD6050	Approved
0.6545	Remote Similarity	NPD7328	Approved
0.6545	Remote Similarity	NPD7327	Approved
0.6542	Remote Similarity	NPD6882	Approved
0.6531	Remote Similarity	NPD5695	Phase 3
0.6518	Remote Similarity	NPD8033	Approved
0.6518	Remote Similarity	NPD8379	Approved
0.6518	Remote Similarity	NPD8296	Approved
0.6518	Remote Similarity	NPD8380	Approved
0.6518	Remote Similarity	NPD8335	Approved
0.6518	Remote Similarity	NPD8378	Approved
0.6512	Remote Similarity	NPD6926	Approved
0.6512	Remote Similarity	NPD6924	Approved
0.65	Remote Similarity	NPD5696	Approved
0.6495	Remote Similarity	NPD4202	Approved
0.6486	Remote Similarity	NPD7516	Approved
0.6484	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6081	Approved
0.6471	Remote Similarity	NPD4243	Approved
0.6465	Remote Similarity	NPD5221	Approved
0.6465	Remote Similarity	NPD5222	Approved
0.6465	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4697	Phase 3
0.6458	Remote Similarity	NPD5692	Phase 3
0.6455	Remote Similarity	NPD7115	Discovery
0.6444	Remote Similarity	NPD6928	Phase 2
0.6437	Remote Similarity	NPD3702	Approved
0.6429	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6695	Phase 3
0.64	Remote Similarity	NPD4755	Approved
0.64	Remote Similarity	NPD5173	Approved
0.6392	Remote Similarity	NPD7637	Suspended
0.6392	Remote Similarity	NPD5694	Approved
0.6364	Remote Similarity	NPD6933	Approved
0.6364	Remote Similarity	NPD6868	Approved
0.6353	Remote Similarity	NPD4787	Phase 1
0.6344	Remote Similarity	NPD3665	Phase 1
0.6344	Remote Similarity	NPD3666	Approved
0.6344	Remote Similarity	NPD3133	Approved
0.6344	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD4225	Approved
0.6333	Remote Similarity	NPD4195	Approved
0.6322	Remote Similarity	NPD4784	Approved
0.6322	Remote Similarity	NPD4785	Approved
0.6316	Remote Similarity	NPD7750	Discontinued
0.631	Remote Similarity	NPD5360	Phase 3
0.631	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5207	Approved
0.6279	Remote Similarity	NPD7151	Approved
0.6279	Remote Similarity	NPD7152	Approved
0.6279	Remote Similarity	NPD7150	Approved
0.6275	Remote Similarity	NPD5285	Approved
0.6275	Remote Similarity	NPD5286	Approved
0.6275	Remote Similarity	NPD4696	Approved
0.6275	Remote Similarity	NPD4700	Approved
0.6265	Remote Similarity	NPD4224	Phase 2
0.6264	Remote Similarity	NPD4748	Discontinued
0.6263	Remote Similarity	NPD5707	Approved
0.625	Remote Similarity	NPD6335	Approved
0.625	Remote Similarity	NPD3703	Phase 2
0.6235	Remote Similarity	NPD6922	Approved
0.6235	Remote Similarity	NPD6923	Approved
0.6216	Remote Similarity	NPD6274	Approved
0.6214	Remote Similarity	NPD5223	Approved
0.6195	Remote Similarity	NPD7101	Approved
0.6195	Remote Similarity	NPD7100	Approved
0.6186	Remote Similarity	NPD7736	Approved
0.6186	Remote Similarity	NPD4753	Phase 2
0.6182	Remote Similarity	NPD4632	Approved
0.6163	Remote Similarity	NPD7143	Approved
0.6163	Remote Similarity	NPD4244	Approved
0.6163	Remote Similarity	NPD4245	Approved
0.6163	Remote Similarity	NPD7144	Approved
0.6163	Remote Similarity	NPD4789	Approved
0.6161	Remote Similarity	NPD6317	Approved
0.6154	Remote Similarity	NPD5225	Approved
0.6154	Remote Similarity	NPD5226	Approved
0.6154	Remote Similarity	NPD5224	Approved
0.6154	Remote Similarity	NPD7507	Approved
0.6154	Remote Similarity	NPD6929	Approved
0.6154	Remote Similarity	NPD4633	Approved
0.6154	Remote Similarity	NPD5211	Phase 2
0.6146	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD7524	Approved
0.6139	Remote Similarity	NPD7732	Phase 3
0.6129	Remote Similarity	NPD4223	Phase 3
0.6129	Remote Similarity	NPD4221	Approved
0.6111	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6314	Approved
0.6106	Remote Similarity	NPD6313	Approved
0.6105	Remote Similarity	NPD1694	Approved
0.6105	Remote Similarity	NPD5329	Approved
0.6095	Remote Similarity	NPD5174	Approved
0.6095	Remote Similarity	NPD4754	Approved
0.6095	Remote Similarity	NPD6052	Approved
0.6095	Remote Similarity	NPD5175	Approved
0.6091	Remote Similarity	NPD8078	Approved
0.6091	Remote Similarity	NPD8077	Approved
0.6087	Remote Similarity	NPD6931	Approved
0.6087	Remote Similarity	NPD7503	Approved
0.6087	Remote Similarity	NPD6909	Approved
0.6087	Remote Similarity	NPD7509	Discontinued
0.6087	Remote Similarity	NPD6908	Approved
0.6087	Remote Similarity	NPD6930	Phase 2
0.6075	Remote Similarity	NPD6412	Phase 2
0.6067	Remote Similarity	NPD4190	Phase 3
0.6067	Remote Similarity	NPD5275	Approved
0.6061	Remote Similarity	NPD5281	Approved
0.6061	Remote Similarity	NPD6411	Approved
0.6061	Remote Similarity	NPD5284	Approved
0.6049	Remote Similarity	NPD1145	Discontinued

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