NPASS Compound

Structure

NPC243893 OpenBabel07101719512D 43 50 0 0 1 0 0 0 0 0999 V2000 -3.8124 -4.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0899 -4.6940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1193 -3.1994 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 -3.1080 -6.0952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0034 -5.1007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9854 -3.6994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3272 -2.2213 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6581 -1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3218 -2.1168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 2 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 -0.8660 -0.5000 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 -4.0215 -6.5020 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8218 -1.2507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7285 -3.0303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 4 36 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 24 2 0 0 0 0 9 24 1 0 0 0 0 10 13 1 0 0 0 0 10 25 2 0 0 0 0 11 15 1 0 0 0 0 11 28 1 0 0 0 0 12 14 2 0 0 0 0 12 30 1 0 0 0 0 13 34 1 0 0 0 0 14 37 1 0 0 0 0 16 23 2 0 0 0 0 17 25 1 0 0 0 0 17 29 1 0 0 0 0 18 26 1 0 0 0 0 19 31 1 0 0 0 0 19 32 1 0 0 0 0 20 23 1 0 0 0 0 20 39 1 0 0 0 0 21 37 1 0 0 0 0 21 38 1 0 0 0 0 22 35 1 0 0 0 0 22 42 1 0 0 0 0 25 35 1 0 0 0 0 26 16 1 6 0 0 0 26 43 1 0 0 0 0 27 18 1 6 0 0 0 27 28 1 0 0 0 0 27 33 1 0 0 0 0 28 37 1 1 0 0 0 29 24 1 6 0 0 0 29 42 1 0 0 0 0 30 34 1 1 0 0 0 30 36 1 0 0 0 0 31 34 1 1 0 0 0 31 35 1 0 0 0 0 32 36 1 6 0 0 0 32 40 1 0 0 0 0 33 41 2 0 0 0 0 33 43 1 0 0 0 0 34 2 1 1 0 0 0 35 3 1 6 0 0 0 36 38 1 6 0 0 0 37 38 1 6 0 0 0 38 15 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.35
Volume:	622.848
LogP:	4.868
LogD:	3.693
LogS:	-5.393
# Rotatable Bonds:	4
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.304
Synthetic Accessibility Score:	5.831
Fsp3:	0.658
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.105
MDCK Permeability:	1.5861754945944995e-05
Pgp-inhibitor:	0.492
Pgp-substrate:	0.508
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.887
30% Bioavailability (F30%):	0.867

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.632
Plasma Protein Binding (PPB):	93.1792984008789%
Volume Distribution (VD):	1.494
Pgp-substrate:	3.80732798576355%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.185
CYP2C19-inhibitor:	0.265
CYP2C19-substrate:	0.7
CYP2C9-inhibitor:	0.525
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.903
CYP3A4-substrate:	0.708

ADMET: Excretion

Clearance (CL):	6.66
Half-life (T1/2):	0.127

ADMET: Toxicity

hERG Blockers:	0.476
Human Hepatotoxicity (H-HT):	0.789
Drug-inuced Liver Injury (DILI):	0.095
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.908
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.676
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC243893

Natural Product ID:	NPC243893
*Common Name:**	Dichapetalin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LRJFCTOUXFAGON-NNLSLSRSSA-N
Standard InCHI:	InChI=1S/C38H48O5/c1-23(20-39)16-26-18-27(33(41)43-26)28-11-15-38-21-37(28,38)14-12-30-34(2)13-10-25-17-29(24-8-6-5-7-9-24)42-22-35(25,3)31(34)19-32(40)36(30,38)4/h5-10,12,14,16,26-32,39-40H,11,13,15,17-22H2,1-4H3/b23-16+/t26-,27-,28-,29-,30+,31+,32+,34+,35-,36-,37+,38+/m0/s1
SMILES:	C/C(=C[C@H]1C[C@@H]([C@@H]2CC[C@@]34C[C@]24C=C[C@@H]2[C@@]4(C)CC=C5C[C@@H](c6ccccc6)OC[C@]5(C)[C@@H]4C[C@H]([C@@]32C)O)C(=O)O1)/CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453157
PubChem CID:	5469156
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
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	stem bark	Philippines	n.a.	PMID[16562829]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24597894]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	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	11
GI50	60
IC50	7
Others	8

Activity Type	# Activity
Cell Line	81
CELL-LINE	1
Individual Protein	1
NON-MOLECULAR	1
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	EC90	<	0.0001	ug ml-1	PMID[506615]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	4.1	ug ml-1	PMID[506616]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	6.1	ug ml-1	PMID[506616]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	3.6	ug ml-1	PMID[506616]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	11.6	ug ml-1	PMID[506616]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[506616]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	7.0	ug ml-1	PMID[506616]
NPT2345	Cell Line	SW626	Homo sapiens	ED50	=	0.2	ug ml-1	PMID[506616]
NPT136	Cell Line	SK-N-SH	Homo sapiens	ED50	=	6.9	ug ml-1	PMID[506616]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	2.1	ug ml-1	PMID[506616]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	=	5.5	ug ml-1	PMID[506616]
NPT137	Cell Line	L1210	Mus musculus	EC90	<	0.0001	ug ml-1	PMID[506616]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	1914.26	nM	PMID[506617]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	1710.02	nM	PMID[506617]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	3334.26	nM	PMID[506617]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	1185.77	nM	PMID[506617]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	2483.13	nM	PMID[506617]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	1196.74	nM	PMID[506617]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	1954.34	nM	PMID[506617]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	10209.39	nM	PMID[506617]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	5081.59	nM	PMID[506617]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	285.76	nM	PMID[506617]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	3564.51	nM	PMID[506617]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	436.52	nM	PMID[506617]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	553.35	nM	PMID[506617]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	3515.6	nM	PMID[506617]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	1588.55	nM	PMID[506617]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	3076.1	nM	PMID[506617]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	10185.91	nM	PMID[506617]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	1037.53	nM	PMID[506617]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	9817.48	nM	PMID[506617]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	4909.08	nM	PMID[506617]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	5345.64	nM	PMID[506617]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	11803.21	nM	PMID[506617]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	10.0	nM	PMID[506617]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	2837.92	nM	PMID[506617]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	2716.44	nM	PMID[506617]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	2884.03	nM	PMID[506617]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	2449.06	nM	PMID[506617]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	2773.32	nM	PMID[506617]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	8279.42	nM	PMID[506617]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	623.73	nM	PMID[506617]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	3033.89	nM	PMID[506617]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	1517.05	nM	PMID[506617]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	3775.72	nM	PMID[506617]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	31405.09	nM	PMID[506617]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	5997.91	nM	PMID[506617]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	2786.12	nM	PMID[506617]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	3548.13	nM	PMID[506617]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	4375.22	nM	PMID[506617]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	1142.88	nM	PMID[506617]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	6745.28	nM	PMID[506617]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	2642.41	nM	PMID[506617]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	1506.61	nM	PMID[506617]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	1782.38	nM	PMID[506617]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	36812.9	nM	PMID[506617]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	721.11	nM	PMID[506617]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	2837.92	nM	PMID[506617]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	9015.71	nM	PMID[506617]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	2477.42	nM	PMID[506617]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	2084.49	nM	PMID[506617]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	2917.43	nM	PMID[506617]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	1342.76	nM	PMID[506617]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	4375.22	nM	PMID[506617]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	10864.26	nM	PMID[506617]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	1958.84	nM	PMID[506617]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	1037.53	nM	PMID[506617]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	14927.94	nM	PMID[506617]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	3741.11	nM	PMID[506617]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	2009.09	nM	PMID[506617]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	77803.66	nM	PMID[506617]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	2009.09	nM	PMID[506617]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	20.0	nM	PMID[506618]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Inhibition	=	28.6	%	PMID[506618]
NPT113	Cell Line	RAW264.7	Mus musculus	Ratio IC50	=	20.0	n.a.	PMID[506618]
NPT2345	Cell Line	SW626	Homo sapiens	IC50	=	340.0	nM	PMID[506619]
NPT137	Cell Line	L1210	Mus musculus	EC90	<	0.17	nM	PMID[506619]
NPT393	Cell Line	HCT-116	Homo sapiens	EC50	=	250.0	nM	PMID[506619]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	11000.0	nM	PMID[506619]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	3000.0	nM	PMID[506619]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	9600.0	nM	PMID[506619]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	12000.0	nM	PMID[506619]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[506616]
NPT2779	Organism	Spodoptera exigua	Spodoptera exigua	EC50	=	3.1	microg/cm2	PMID[506618]
NPT1272	Organism	Panagrellus redivivus	Panagrellus redivivus	mortality	=	15.3	%	PMID[506618]
NPT610	Others	Molecular identity unknown		IZ	=	12.8	mm	PMID[506618]
NPT529	Organism	Rhizoctonia solani	Rhizoctonia solani	IZ	=	10.5	mm	PMID[506618]
NPT2	Others	Unspecified		IC50	=	7000.0	nM	PMID[506619]
NPT23813	CELL-LINE	WM 266-4	Homo sapiens	EC50	=	17000.0	nM	PMID[506619]

☑ 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 NPC243893 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	288
0.1-0.2	1128
0.2-0.3	2240
0.3-0.4	4632
0.4-0.5	9039
0.5-0.6	19269
0.6-0.7	5181
0.7-0.8	891
0.8-0.85	19
0.85-0.9	6
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9846	High Similarity	NPC262324
0.9697	High Similarity	NPC79921
0.9542	High Similarity	NPC471864
0.9149	High Similarity	NPC253591
0.8889	High Similarity	NPC261659
0.8811	High Similarity	NPC475561
0.8811	High Similarity	NPC475417
0.8643	High Similarity	NPC471862
0.8613	High Similarity	NPC203486
0.8529	High Similarity	NPC470278
0.8478	Intermediate Similarity	NPC48929
0.8451	Intermediate Similarity	NPC471856
0.8377	Intermediate Similarity	NPC471861
0.8298	Intermediate Similarity	NPC475373
0.8296	Intermediate Similarity	NPC470816
0.8261	Intermediate Similarity	NPC72915
0.8255	Intermediate Similarity	NPC472657
0.8255	Intermediate Similarity	NPC472658
0.8235	Intermediate Similarity	NPC5486
0.8235	Intermediate Similarity	NPC253681
0.8227	Intermediate Similarity	NPC472374
0.8227	Intermediate Similarity	NPC472372
0.8148	Intermediate Similarity	NPC307139
0.8129	Intermediate Similarity	NPC471858
0.8121	Intermediate Similarity	NPC279442
0.8102	Intermediate Similarity	NPC169913
0.8085	Intermediate Similarity	NPC126516
0.8085	Intermediate Similarity	NPC329913
0.8077	Intermediate Similarity	NPC471850
0.8074	Intermediate Similarity	NPC273336
0.8074	Intermediate Similarity	NPC182333
0.8067	Intermediate Similarity	NPC472548
0.8058	Intermediate Similarity	NPC475138
0.8058	Intermediate Similarity	NPC472388
0.8056	Intermediate Similarity	NPC234548
0.8056	Intermediate Similarity	NPC248287
0.8042	Intermediate Similarity	NPC39549
0.8029	Intermediate Similarity	NPC275576
0.8028	Intermediate Similarity	NPC477893
0.8015	Intermediate Similarity	NPC77691
0.8014	Intermediate Similarity	NPC131966
0.8014	Intermediate Similarity	NPC191387
0.8	Intermediate Similarity	NPC224491
0.7987	Intermediate Similarity	NPC471860
0.7987	Intermediate Similarity	NPC471859
0.7986	Intermediate Similarity	NPC225103
0.7973	Intermediate Similarity	NPC473602
0.7972	Intermediate Similarity	NPC472551
0.7972	Intermediate Similarity	NPC472545
0.7971	Intermediate Similarity	NPC473220
0.7971	Intermediate Similarity	NPC470753
0.7961	Intermediate Similarity	NPC472549
0.7959	Intermediate Similarity	NPC475122
0.7947	Intermediate Similarity	NPC477905
0.7945	Intermediate Similarity	NPC140021
0.7933	Intermediate Similarity	NPC125033
0.7931	Intermediate Similarity	NPC183270
0.7931	Intermediate Similarity	NPC472547
0.7931	Intermediate Similarity	NPC477904
0.7931	Intermediate Similarity	NPC100913
0.7931	Intermediate Similarity	NPC473440
0.7931	Intermediate Similarity	NPC90614
0.7931	Intermediate Similarity	NPC275592
0.7929	Intermediate Similarity	NPC473443
0.7929	Intermediate Similarity	NPC147561
0.7929	Intermediate Similarity	NPC49272
0.7922	Intermediate Similarity	NPC476784
0.7919	Intermediate Similarity	NPC132652
0.7917	Intermediate Similarity	NPC249817
0.7905	Intermediate Similarity	NPC472572
0.7905	Intermediate Similarity	NPC473088
0.7905	Intermediate Similarity	NPC70403
0.7905	Intermediate Similarity	NPC470159
0.7905	Intermediate Similarity	NPC174982
0.7905	Intermediate Similarity	NPC472568
0.7905	Intermediate Similarity	NPC184817
0.7905	Intermediate Similarity	NPC472575
0.7905	Intermediate Similarity	NPC200471
0.7905	Intermediate Similarity	NPC177940
0.7905	Intermediate Similarity	NPC471104
0.7905	Intermediate Similarity	NPC158663
0.7905	Intermediate Similarity	NPC171525
0.7905	Intermediate Similarity	NPC472556
0.7905	Intermediate Similarity	NPC470157
0.7905	Intermediate Similarity	NPC476973
0.7905	Intermediate Similarity	NPC472571
0.7905	Intermediate Similarity	NPC469349
0.7905	Intermediate Similarity	NPC96903
0.7905	Intermediate Similarity	NPC29704
0.7902	Intermediate Similarity	NPC473216
0.7902	Intermediate Similarity	NPC473399
0.7902	Intermediate Similarity	NPC477896
0.7899	Intermediate Similarity	NPC470765
0.7891	Intermediate Similarity	NPC91703
0.7891	Intermediate Similarity	NPC477894
0.7891	Intermediate Similarity	NPC163087
0.7887	Intermediate Similarity	NPC472656
0.7877	Intermediate Similarity	NPC27377
0.7877	Intermediate Similarity	NPC87448
0.7877	Intermediate Similarity	NPC472576
0.7877	Intermediate Similarity	NPC16912
0.7877	Intermediate Similarity	NPC97947
0.7877	Intermediate Similarity	NPC41481
0.7877	Intermediate Similarity	NPC291599
0.7877	Intermediate Similarity	NPC118080
0.7868	Intermediate Similarity	NPC369
0.7868	Intermediate Similarity	NPC293831
0.7867	Intermediate Similarity	NPC92293
0.7867	Intermediate Similarity	NPC266265
0.7867	Intermediate Similarity	NPC270590
0.7867	Intermediate Similarity	NPC301556
0.7867	Intermediate Similarity	NPC471101
0.7862	Intermediate Similarity	NPC475482
0.7862	Intermediate Similarity	NPC198621
0.7862	Intermediate Similarity	NPC216940
0.7862	Intermediate Similarity	NPC22676
0.7852	Intermediate Similarity	NPC478263
0.7852	Intermediate Similarity	NPC474935
0.7852	Intermediate Similarity	NPC133389
0.7852	Intermediate Similarity	NPC234337
0.7852	Intermediate Similarity	NPC240115
0.7852	Intermediate Similarity	NPC183339
0.7847	Intermediate Similarity	NPC477874
0.7847	Intermediate Similarity	NPC173569
0.7842	Intermediate Similarity	NPC190849
0.7842	Intermediate Similarity	NPC171007
0.7838	Intermediate Similarity	NPC470152
0.7838	Intermediate Similarity	NPC476974
0.7838	Intermediate Similarity	NPC475759
0.7838	Intermediate Similarity	NPC472569
0.7838	Intermediate Similarity	NPC57628
0.7838	Intermediate Similarity	NPC472573
0.7838	Intermediate Similarity	NPC188865
0.7838	Intermediate Similarity	NPC163719
0.7838	Intermediate Similarity	NPC472570
0.7838	Intermediate Similarity	NPC241951
0.7838	Intermediate Similarity	NPC25768
0.7838	Intermediate Similarity	NPC11685
0.7838	Intermediate Similarity	NPC95810
0.7838	Intermediate Similarity	NPC95265
0.7838	Intermediate Similarity	NPC70716
0.7838	Intermediate Similarity	NPC125106
0.7834	Intermediate Similarity	NPC478073
0.7832	Intermediate Similarity	NPC310662
0.7829	Intermediate Similarity	NPC233581
0.7829	Intermediate Similarity	NPC469647
0.7829	Intermediate Similarity	NPC22571
0.7829	Intermediate Similarity	NPC138641
0.7829	Intermediate Similarity	NPC283875
0.7829	Intermediate Similarity	NPC469648
0.7829	Intermediate Similarity	NPC145649
0.7823	Intermediate Similarity	NPC472546
0.7823	Intermediate Similarity	NPC63737
0.7823	Intermediate Similarity	NPC192658
0.7823	Intermediate Similarity	NPC183540
0.7823	Intermediate Similarity	NPC475135
0.7823	Intermediate Similarity	NPC34012
0.7823	Intermediate Similarity	NPC172311
0.782	Intermediate Similarity	NPC470820
0.7817	Intermediate Similarity	NPC471880
0.7817	Intermediate Similarity	NPC80599
0.7817	Intermediate Similarity	NPC472394
0.7815	Intermediate Similarity	NPC325032
0.7815	Intermediate Similarity	NPC477483
0.7808	Intermediate Similarity	NPC475400
0.7808	Intermediate Similarity	NPC97667
0.7808	Intermediate Similarity	NPC171207
0.7808	Intermediate Similarity	NPC87934
0.7808	Intermediate Similarity	NPC162613
0.78	Intermediate Similarity	NPC281717
0.7792	Intermediate Similarity	NPC475548
0.7792	Intermediate Similarity	NPC475638
0.7792	Intermediate Similarity	NPC290683
0.7792	Intermediate Similarity	NPC154675
0.7786	Intermediate Similarity	NPC230331
0.7785	Intermediate Similarity	NPC478264
0.7785	Intermediate Similarity	NPC477207
0.7778	Intermediate Similarity	NPC11266
0.7778	Intermediate Similarity	NPC471135
0.777	Intermediate Similarity	NPC95449
0.777	Intermediate Similarity	NPC477468
0.7763	Intermediate Similarity	NPC470153
0.7763	Intermediate Similarity	NPC472398
0.7761	Intermediate Similarity	NPC45794
0.7756	Intermediate Similarity	NPC326328
0.7756	Intermediate Similarity	NPC323356
0.7756	Intermediate Similarity	NPC471138
0.7756	Intermediate Similarity	NPC309991
0.7755	Intermediate Similarity	NPC325078
0.7754	Intermediate Similarity	NPC470815
0.7754	Intermediate Similarity	NPC12881
0.7754	Intermediate Similarity	NPC472373
0.7754	Intermediate Similarity	NPC469742
0.7754	Intermediate Similarity	NPC140118
0.7748	Intermediate Similarity	NPC476975
0.7748	Intermediate Similarity	NPC473215
0.7748	Intermediate Similarity	NPC472937
0.7748	Intermediate Similarity	NPC472936
0.7748	Intermediate Similarity	NPC472938
0.7744	Intermediate Similarity	NPC475244

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 NPC243893 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	736
0.2-0.3	1449
0.3-0.4	2909
0.4-0.5	2331
0.5-0.6	1260
0.6-0.7	210
0.7-0.8	14
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7836	Intermediate Similarity	NPD7741	Discontinued
0.7785	Intermediate Similarity	NPD7236	Approved
0.7569	Intermediate Similarity	NPD6663	Approved
0.7532	Intermediate Similarity	NPD7239	Suspended
0.7439	Intermediate Similarity	NPD7799	Discontinued
0.7413	Intermediate Similarity	NPD5736	Approved
0.7407	Intermediate Similarity	NPD2629	Approved
0.7343	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8166	Discontinued
0.7286	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD6858	Approved
0.7259	Intermediate Similarity	NPD7094	Approved
0.7239	Intermediate Similarity	NPD8127	Discontinued
0.7222	Intermediate Similarity	NPD6085	Phase 2
0.7222	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6002	Phase 3
0.7219	Intermediate Similarity	NPD6004	Phase 3
0.7219	Intermediate Similarity	NPD6005	Phase 3
0.72	Intermediate Similarity	NPD7305	Phase 1
0.7101	Intermediate Similarity	NPD4198	Discontinued
0.7099	Intermediate Similarity	NPD7058	Phase 2
0.7099	Intermediate Similarity	NPD7057	Phase 3
0.7095	Intermediate Similarity	NPD7961	Discontinued
0.7095	Intermediate Similarity	NPD8032	Phase 2
0.7092	Intermediate Similarity	NPD5126	Approved
0.7092	Intermediate Similarity	NPD2932	Approved
0.7092	Intermediate Similarity	NPD5125	Phase 3
0.7075	Intermediate Similarity	NPD7008	Discontinued
0.707	Intermediate Similarity	NPD6273	Approved
0.7047	Intermediate Similarity	NPD4140	Approved
0.7044	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7228	Approved
0.6994	Remote Similarity	NPD4966	Approved
0.6994	Remote Similarity	NPD4965	Approved
0.6994	Remote Similarity	NPD4967	Phase 2
0.6993	Remote Similarity	NPD5762	Approved
0.6993	Remote Similarity	NPD5763	Approved
0.6985	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7714	Approved
0.698	Remote Similarity	NPD7715	Approved
0.6972	Remote Similarity	NPD3019	Approved
0.6972	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6010	Discontinued
0.694	Remote Similarity	NPD6685	Approved
0.6914	Remote Similarity	NPD37	Approved
0.6913	Remote Similarity	NPD3764	Approved
0.6894	Remote Similarity	NPD7028	Phase 2
0.6887	Remote Similarity	NPD6355	Discontinued
0.6882	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5761	Phase 2
0.6871	Remote Similarity	NPD5760	Phase 2
0.6859	Remote Similarity	NPD4628	Phase 3
0.6838	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6234	Discontinued
0.68	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5951	Approved
0.6779	Remote Similarity	NPD7055	Discontinued
0.6776	Remote Similarity	NPD5735	Approved
0.6774	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7240	Approved
0.6761	Remote Similarity	NPD8434	Phase 2
0.6761	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7033	Discontinued
0.6752	Remote Similarity	NPD4110	Phase 3
0.6752	Remote Similarity	NPD7003	Approved
0.6752	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD8407	Phase 2
0.6741	Remote Similarity	NPD5048	Discontinued
0.6736	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7199	Phase 2
0.6716	Remote Similarity	NPD5765	Approved
0.6716	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6647	Phase 2
0.6714	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD3091	Approved
0.671	Remote Similarity	NPD6099	Approved
0.671	Remote Similarity	NPD6100	Approved
0.671	Remote Similarity	NPD7137	Phase 2
0.669	Remote Similarity	NPD3023	Approved
0.669	Remote Similarity	NPD3026	Approved
0.6688	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD5909	Discontinued
0.6667	Remote Similarity	NPD8455	Phase 2
0.6667	Remote Similarity	NPD8368	Discontinued
0.6667	Remote Similarity	NPD6764	Approved
0.6667	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD3024	Approved
0.6667	Remote Similarity	NPD6765	Approved
0.6644	Remote Similarity	NPD3092	Approved
0.6643	Remote Similarity	NPD7610	Discontinued
0.6626	Remote Similarity	NPD7458	Discontinued
0.6626	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6353	Approved
0.6622	Remote Similarity	NPD1283	Approved
0.6621	Remote Similarity	NPD3095	Discontinued
0.662	Remote Similarity	NPD7115	Discovery
0.6617	Remote Similarity	NPD7640	Approved
0.6617	Remote Similarity	NPD7639	Approved
0.6604	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.66	Remote Similarity	NPD2861	Phase 2
0.6599	Remote Similarity	NPD1608	Approved
0.6594	Remote Similarity	NPD2182	Approved
0.6592	Remote Similarity	NPD8360	Approved
0.6592	Remote Similarity	NPD8361	Approved
0.6579	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD3094	Phase 2
0.6571	Remote Similarity	NPD6912	Phase 3
0.6571	Remote Similarity	NPD7685	Pre-registration
0.6566	Remote Similarity	NPD7819	Suspended
0.6554	Remote Similarity	NPD5327	Phase 3
0.6552	Remote Similarity	NPD5585	Approved
0.655	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD4766	Approved
0.6541	Remote Similarity	NPD7638	Approved
0.6533	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD5647	Approved
0.6522	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6784	Approved
0.6517	Remote Similarity	NPD6785	Approved
0.6516	Remote Similarity	NPD6653	Approved
0.651	Remote Similarity	NPD8651	Approved
0.6509	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD1778	Approved
0.65	Remote Similarity	NPD8435	Approved
0.6497	Remote Similarity	NPD8312	Approved
0.6497	Remote Similarity	NPD8313	Approved
0.6494	Remote Similarity	NPD2979	Phase 3
0.6491	Remote Similarity	NPD7229	Phase 3
0.6483	Remote Similarity	NPD7009	Phase 2
0.6481	Remote Similarity	NPD2533	Approved
0.6481	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD2532	Approved
0.6481	Remote Similarity	NPD2534	Approved
0.6478	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6798	Discontinued
0.6467	Remote Similarity	NPD2797	Approved
0.6467	Remote Similarity	NPD8485	Approved
0.6458	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD2346	Discontinued
0.6452	Remote Similarity	NPD5124	Phase 1
0.6452	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD1693	Approved
0.6438	Remote Similarity	NPD3750	Approved
0.6429	Remote Similarity	NPD2067	Discontinued
0.6429	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD4624	Approved
0.6419	Remote Similarity	NPD4806	Approved
0.6419	Remote Similarity	NPD6287	Discontinued
0.6419	Remote Similarity	NPD4807	Approved
0.6419	Remote Similarity	NPD1281	Approved
0.6418	Remote Similarity	NPD9495	Approved
0.6412	Remote Similarity	NPD1088	Approved
0.6409	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD7095	Approved
0.64	Remote Similarity	NPD5844	Phase 1
0.6398	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5305	Approved
0.6395	Remote Similarity	NPD5306	Approved
0.6395	Remote Similarity	NPD7315	Approved
0.6395	Remote Similarity	NPD17	Approved
0.6392	Remote Similarity	NPD2438	Suspended
0.6391	Remote Similarity	NPD7768	Phase 2
0.6391	Remote Similarity	NPD1989	Approved
0.6387	Remote Similarity	NPD3620	Phase 2
0.6387	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4060	Phase 1
0.6382	Remote Similarity	NPD3664	Approved
0.6382	Remote Similarity	NPD3663	Approved
0.6382	Remote Similarity	NPD3661	Approved
0.6382	Remote Similarity	NPD3662	Phase 3
0.6382	Remote Similarity	NPD7084	Phase 3
0.637	Remote Similarity	NPD9545	Approved
0.637	Remote Similarity	NPD7798	Approved
0.637	Remote Similarity	NPD2066	Phase 3
0.6369	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3268	Approved
0.6364	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6362	Approved
0.6358	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD7266	Discontinued
0.635	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7680	Approved
0.6349	Remote Similarity	NPD7497	Discontinued
0.6346	Remote Similarity	NPD4685	Phase 3
0.6346	Remote Similarity	NPD4686	Approved
0.6346	Remote Similarity	NPD4684	Phase 3

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