NPASS Compound

Structure

CID201048 OpenBabel06191715592D 22 23 0 0 1 0 0 0 0 0999 V2000 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 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 -0.0000 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 15 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 16 18 1 0 0 0 0 16 19 1 6 0 0 0 17 19 1 6 0 0 0 17 20 1 0 0 0 0 19 4 1 6 0 0 0 20 5 1 6 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.27
Volume:	352.307
LogP:	4.513
LogD:	4.056
LogS:	-4.825
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.739
Synthetic Accessibility Score:	4.105
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.483
MDCK Permeability:	1.8504881154512987e-05
Pgp-inhibitor:	0.448
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.901
30% Bioavailability (F30%):	0.536

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.434
Plasma Protein Binding (PPB):	91.68599700927734%
Volume Distribution (VD):	1.729
Pgp-substrate:	8.09913158416748%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.272
CYP2C19-inhibitor:	0.09
CYP2C19-substrate:	0.845
CYP2C9-inhibitor:	0.177
CYP2C9-substrate:	0.674
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.358
CYP3A4-inhibitor:	0.211
CYP3A4-substrate:	0.215

ADMET: Excretion

Clearance (CL):	6.78
Half-life (T1/2):	0.392

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.256
Skin Sensitization:	0.946
Carcinogencity:	0.035
Eye Corrosion:	0.733
Eye Irritation:	0.899
Respiratory Toxicity:	0.819

Download Data

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

Natural Product: NPC201048

Natural Product ID:	NPC201048
*Common Name:**	(1R,2R,4As,8As)-1-[(E)-5-Hydroxy-3-Methylpent-3-Enyl]-2,5,5,8A-Tetramethyl-3,4,4A,6,7,8-Hexahydro-1H-Naphthalen-2-Ol
IUPAC Name:	(1R,2R,4aS,8aS)-1-[(E)-5-hydroxy-3-methylpent-3-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
Synonyms:	8Alpha,15-Dihydroxy-13Elabdene
Standard InCHIKey:	LEOHDQKUMQKLMP-NUKBDRAPSA-N
Standard InCHI:	InChI=1S/C20H36O2/c1-15(10-14-21)7-8-17-19(4)12-6-11-18(2,3)16(19)9-13-20(17,5)22/h10,16-17,21-22H,6-9,11-14H2,1-5H3/b15-10+/t16-,17+,19-,20+/m0/s1
SMILES:	C/C(=CCO)/CC[C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2CC[C@@]1(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1644112
PubChem CID:	5471228
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO8355	Zaluzania triloba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4020(01)97900-1]
NPO9285	Eupatorium kiirunense	Species	Asteraceae	Eukaryota	n.a.	Taiwan	n.a.	PMID[15921421]
NPO9285	Eupatorium kiirunense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921421]
NPO20847	Pandaros acanthifolium	Species	Clathriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20614907]
NPO23499	Carpesium faberi	Species	Asteraceae	Eukaryota	whole plant	Changshou County, Chongqing, China	2008-Aug	PMID[21109433]
NPO20847	Pandaros acanthifolium	Species	Clathriidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[23245401]
NPO7052	Physalis nicandroides	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25634541]
NPO40306	Psiadia arguta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30943031]
NPO7052	Physalis nicandroides	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31429569]
NPO10978	Annona senegalensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623038]
NPO10649	Guatteria ouregou	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8676127]
NPO10978	Annona senegalensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882434]
NPO2788	Virola surinamensis	Species	Myristicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO2788	Virola surinamensis	Species	Myristicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2788	Virola surinamensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO2788	Virola surinamensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2788	Virola surinamensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO20847	Pandaros acanthifolium	Species	Clathriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23499	Carpesium faberi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10006	Paraburkholderia caryophylli	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8355	Zaluzania triloba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9285	Eupatorium kiirunense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11226	Arenaria venezuelana	Species	Scolopacidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7052	Physalis nicandroides	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO785	Nephroma parile	Species	Nephromataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3855	Randia nilotica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11096	Earina autumnalis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO285	Homeria glauca	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2788	Virola surinamensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21883	Veronica undulata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10649	Guatteria ouregou	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19675	Eptatretus burgeri	Species	Myxinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10978	Annona senegalensis	Species	Annonaceae	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
GI50	59
IC50	3
Others	4

Activity Type	# Activity
Cell Line	60
Individual Protein	1
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	18.6	ug.mL-1	PMID[481427]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	17498.47	nM	PMID[481428]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	18749.95	nM	PMID[481428]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	34197.94	nM	PMID[481428]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	20464.45	nM	PMID[481428]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	23442.29	nM	PMID[481428]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	16710.91	nM	PMID[481428]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	17988.71	nM	PMID[481428]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	20511.62	nM	PMID[481428]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	17906.06	nM	PMID[481428]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	18071.74	nM	PMID[481428]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	19678.86	nM	PMID[481428]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	16982.44	nM	PMID[481428]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	16519.62	nM	PMID[481428]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	13899.53	nM	PMID[481428]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	51760.68	nM	PMID[481428]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	17100.15	nM	PMID[481428]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	17258.38	nM	PMID[481428]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	16180.8	nM	PMID[481428]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	23120.65	nM	PMID[481428]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	17258.38	nM	PMID[481428]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	21281.39	nM	PMID[481428]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	14321.88	nM	PMID[481428]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	17458.22	nM	PMID[481428]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	22698.65	nM	PMID[481428]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	19230.92	nM	PMID[481428]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	16710.91	nM	PMID[481428]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	23442.29	nM	PMID[481428]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	82413.81	nM	PMID[481428]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	17218.69	nM	PMID[481428]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	17298.16	nM	PMID[481428]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	16069.41	nM	PMID[481428]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	18281.0	nM	PMID[481428]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	17579.24	nM	PMID[481428]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	16032.45	nM	PMID[481428]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	29648.31	nM	PMID[481428]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	17701.09	nM	PMID[481428]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	17338.04	nM	PMID[481428]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	22029.26	nM	PMID[481428]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	17660.38	nM	PMID[481428]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	24774.22	nM	PMID[481428]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	16405.9	nM	PMID[481428]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	17100.15	nM	PMID[481428]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	21281.39	nM	PMID[481428]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	17258.38	nM	PMID[481428]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	18238.96	nM	PMID[481428]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	28641.78	nM	PMID[481428]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	14060.48	nM	PMID[481428]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	17579.24	nM	PMID[481428]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	18281.0	nM	PMID[481428]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	17021.59	nM	PMID[481428]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	20370.42	nM	PMID[481428]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	24043.63	nM	PMID[481428]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	19453.6	nM	PMID[481428]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	20417.38	nM	PMID[481428]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	21330.45	nM	PMID[481428]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	18492.69	nM	PMID[481428]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	22335.72	nM	PMID[481428]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	17579.24	nM	PMID[481428]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	17701.09	nM	PMID[481428]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Activity	=	6.7	%	PMID[481431]
NPT32	Organism	Mus musculus	Mus musculus	Ratio IC50	=	2.0	n.a.	PMID[481429]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	670.0	nM	PMID[481429]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	64.32	%	PMID[481429]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	36600.0	nM	PMID[481430]
NPT2	Others	Unspecified		Activity	=	1.1	%	PMID[481431]

☑ 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 NPC201048 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	174
0.1-0.2	1415
0.2-0.3	5667
0.3-0.4	15713
0.4-0.5	8980
0.5-0.6	6123
0.6-0.7	3296
0.7-0.8	1040
0.8-0.85	215
0.85-0.9	56
0.9-0.95	13
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476366
0.9714	High Similarity	NPC470749
0.9577	High Similarity	NPC470711
0.9577	High Similarity	NPC470758
0.9571	High Similarity	NPC32832
0.942	High Similarity	NPC167706
0.9167	High Similarity	NPC265588
0.9155	High Similarity	NPC306727
0.9118	High Similarity	NPC69649
0.9118	High Similarity	NPC68703
0.9041	High Similarity	NPC91594
0.9	High Similarity	NPC34834
0.8947	High Similarity	NPC2524
0.8947	High Similarity	NPC218616
0.8947	High Similarity	NPC296701
0.8947	High Similarity	NPC155521
0.8933	High Similarity	NPC295131
0.8919	High Similarity	NPC11908
0.8873	High Similarity	NPC23954
0.8857	High Similarity	NPC9942
0.8824	High Similarity	NPC258595
0.8816	High Similarity	NPC249423
0.8816	High Similarity	NPC476646
0.88	High Similarity	NPC30986
0.88	High Similarity	NPC209430
0.875	High Similarity	NPC182717
0.875	High Similarity	NPC220939
0.875	High Similarity	NPC265485
0.8714	High Similarity	NPC96484
0.8714	High Similarity	NPC94192
0.8701	High Similarity	NPC87489
0.8701	High Similarity	NPC49964
0.8696	High Similarity	NPC476406
0.8684	High Similarity	NPC281880
0.8684	High Similarity	NPC96362
0.8667	High Similarity	NPC476314
0.8667	High Similarity	NPC167891
0.8667	High Similarity	NPC285761
0.8667	High Similarity	NPC83351
0.8649	High Similarity	NPC253190
0.863	High Similarity	NPC243342
0.863	High Similarity	NPC91858
0.863	High Similarity	NPC477138
0.863	High Similarity	NPC100334
0.8611	High Similarity	NPC164022
0.8611	High Similarity	NPC471272
0.8611	High Similarity	NPC477792
0.8592	High Similarity	NPC476431
0.859	High Similarity	NPC476927
0.859	High Similarity	NPC82623
0.8571	High Similarity	NPC159148
0.8571	High Similarity	NPC264245
0.8553	High Similarity	NPC273410
0.8553	High Similarity	NPC143182
0.8553	High Similarity	NPC28862
0.8553	High Similarity	NPC80530
0.8553	High Similarity	NPC47982
0.8553	High Similarity	NPC84694
0.8553	High Similarity	NPC81306
0.8553	High Similarity	NPC109546
0.8553	High Similarity	NPC291379
0.8533	High Similarity	NPC471798
0.8533	High Similarity	NPC472805
0.8533	High Similarity	NPC101475
0.8533	High Similarity	NPC157996
0.8533	High Similarity	NPC34177
0.8533	High Similarity	NPC90979
0.8533	High Similarity	NPC40394
0.8533	High Similarity	NPC132542
0.8514	High Similarity	NPC291503
0.8514	High Similarity	NPC66566
0.8514	High Similarity	NPC477923
0.85	High Similarity	NPC6391
0.85	High Similarity	NPC261266
0.85	High Similarity	NPC475069
0.85	High Similarity	NPC175145
0.8493	Intermediate Similarity	NPC471799
0.8493	Intermediate Similarity	NPC474743
0.8493	Intermediate Similarity	NPC68443
0.8481	Intermediate Similarity	NPC231310
0.8481	Intermediate Similarity	NPC205845
0.8481	Intermediate Similarity	NPC470077
0.8481	Intermediate Similarity	NPC474047
0.8472	Intermediate Similarity	NPC92801
0.8462	Intermediate Similarity	NPC101462
0.8462	Intermediate Similarity	NPC202389
0.8462	Intermediate Similarity	NPC470049
0.8462	Intermediate Similarity	NPC304285
0.8451	Intermediate Similarity	NPC245795
0.8451	Intermediate Similarity	NPC208999
0.8451	Intermediate Similarity	NPC471238
0.8451	Intermediate Similarity	NPC276616
0.8451	Intermediate Similarity	NPC2648
0.8442	Intermediate Similarity	NPC164840
0.8442	Intermediate Similarity	NPC241290
0.8442	Intermediate Similarity	NPC209944
0.8442	Intermediate Similarity	NPC322313
0.8442	Intermediate Similarity	NPC236237
0.8442	Intermediate Similarity	NPC234193
0.8442	Intermediate Similarity	NPC13554
0.8442	Intermediate Similarity	NPC102253
0.8429	Intermediate Similarity	NPC279434
0.8421	Intermediate Similarity	NPC99168
0.8421	Intermediate Similarity	NPC6978
0.8421	Intermediate Similarity	NPC138621
0.8421	Intermediate Similarity	NPC253807
0.8421	Intermediate Similarity	NPC300499
0.8421	Intermediate Similarity	NPC230295
0.8421	Intermediate Similarity	NPC474216
0.8421	Intermediate Similarity	NPC470396
0.8421	Intermediate Similarity	NPC158662
0.8421	Intermediate Similarity	NPC167037
0.8421	Intermediate Similarity	NPC196753
0.8421	Intermediate Similarity	NPC98386
0.8421	Intermediate Similarity	NPC474989
0.8421	Intermediate Similarity	NPC22955
0.8421	Intermediate Similarity	NPC244385
0.8406	Intermediate Similarity	NPC101128
0.8406	Intermediate Similarity	NPC225415
0.8406	Intermediate Similarity	NPC68656
0.84	Intermediate Similarity	NPC237460
0.84	Intermediate Similarity	NPC27765
0.84	Intermediate Similarity	NPC290598
0.84	Intermediate Similarity	NPC244488
0.84	Intermediate Similarity	NPC122418
0.84	Intermediate Similarity	NPC189883
0.84	Intermediate Similarity	NPC30590
0.84	Intermediate Similarity	NPC106432
0.84	Intermediate Similarity	NPC120098
0.84	Intermediate Similarity	NPC247325
0.84	Intermediate Similarity	NPC265328
0.8395	Intermediate Similarity	NPC476948
0.8378	Intermediate Similarity	NPC471797
0.8378	Intermediate Similarity	NPC476736
0.8378	Intermediate Similarity	NPC469534
0.8378	Intermediate Similarity	NPC469593
0.8378	Intermediate Similarity	NPC469533
0.8375	Intermediate Similarity	NPC318390
0.8375	Intermediate Similarity	NPC470360
0.8375	Intermediate Similarity	NPC274448
0.8356	Intermediate Similarity	NPC242001
0.8356	Intermediate Similarity	NPC471271
0.8356	Intermediate Similarity	NPC110799
0.8356	Intermediate Similarity	NPC471268
0.8354	Intermediate Similarity	NPC470558
0.8354	Intermediate Similarity	NPC317458
0.8354	Intermediate Similarity	NPC474634
0.8354	Intermediate Similarity	NPC134481
0.8354	Intermediate Similarity	NPC475789
0.8333	Intermediate Similarity	NPC471560
0.8333	Intermediate Similarity	NPC209620
0.8333	Intermediate Similarity	NPC210323
0.8333	Intermediate Similarity	NPC23852
0.8333	Intermediate Similarity	NPC47761
0.8333	Intermediate Similarity	NPC474248
0.8312	Intermediate Similarity	NPC472463
0.8312	Intermediate Similarity	NPC1319
0.8312	Intermediate Similarity	NPC53744
0.831	Intermediate Similarity	NPC101307
0.831	Intermediate Similarity	NPC139207
0.831	Intermediate Similarity	NPC253303
0.831	Intermediate Similarity	NPC185874
0.831	Intermediate Similarity	NPC117607
0.831	Intermediate Similarity	NPC114651
0.831	Intermediate Similarity	NPC88454
0.831	Intermediate Similarity	NPC171225
0.831	Intermediate Similarity	NPC269077
0.831	Intermediate Similarity	NPC197805
0.8293	Intermediate Similarity	NPC133588
0.8289	Intermediate Similarity	NPC214570
0.8289	Intermediate Similarity	NPC155986
0.8289	Intermediate Similarity	NPC318495
0.8289	Intermediate Similarity	NPC130136
0.8289	Intermediate Similarity	NPC474826
0.8289	Intermediate Similarity	NPC477427
0.8289	Intermediate Similarity	NPC477425
0.8289	Intermediate Similarity	NPC477426
0.8289	Intermediate Similarity	NPC198968
0.8289	Intermediate Similarity	NPC477924
0.8286	Intermediate Similarity	NPC64123
0.8272	Intermediate Similarity	NPC299068
0.8267	Intermediate Similarity	NPC138374
0.8267	Intermediate Similarity	NPC144075
0.8267	Intermediate Similarity	NPC141071
0.8267	Intermediate Similarity	NPC471723
0.8267	Intermediate Similarity	NPC257347
0.8267	Intermediate Similarity	NPC185536
0.8267	Intermediate Similarity	NPC34700
0.8267	Intermediate Similarity	NPC133580
0.8261	Intermediate Similarity	NPC81615
0.825	Intermediate Similarity	NPC185568
0.825	Intermediate Similarity	NPC15534
0.825	Intermediate Similarity	NPC306951
0.825	Intermediate Similarity	NPC238485
0.8243	Intermediate Similarity	NPC130665
0.8235	Intermediate Similarity	NPC240506
0.8228	Intermediate Similarity	NPC30166
0.8228	Intermediate Similarity	NPC471408
0.8228	Intermediate Similarity	NPC50964
0.8228	Intermediate Similarity	NPC189972

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 NPC201048 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	1751
0.2-0.3	4050
0.3-0.4	2235
0.4-0.5	554
0.5-0.6	225
0.6-0.7	136
0.7-0.8	42
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8442	Intermediate Similarity	NPD7525	Registered
0.8312	Intermediate Similarity	NPD7645	Phase 2
0.8026	Intermediate Similarity	NPD6942	Approved
0.8026	Intermediate Similarity	NPD7339	Approved
0.8026	Intermediate Similarity	NPD8264	Approved
0.7922	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6926	Approved
0.7895	Intermediate Similarity	NPD6924	Approved
0.775	Intermediate Similarity	NPD6930	Phase 2
0.775	Intermediate Similarity	NPD6931	Approved
0.7738	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6933	Approved
0.7632	Intermediate Similarity	NPD4243	Approved
0.7625	Intermediate Similarity	NPD6929	Approved
0.7606	Intermediate Similarity	NPD368	Approved
0.7531	Intermediate Similarity	NPD7332	Phase 2
0.7531	Intermediate Similarity	NPD7514	Phase 3
0.7531	Intermediate Similarity	NPD7509	Discontinued
0.747	Intermediate Similarity	NPD6695	Phase 3
0.7436	Intermediate Similarity	NPD4785	Approved
0.7436	Intermediate Similarity	NPD4784	Approved
0.7412	Intermediate Similarity	NPD3618	Phase 1
0.7403	Intermediate Similarity	NPD7150	Approved
0.7403	Intermediate Similarity	NPD7151	Approved
0.7403	Intermediate Similarity	NPD7152	Approved
0.7381	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4786	Approved
0.7375	Intermediate Similarity	NPD5776	Phase 2
0.7375	Intermediate Similarity	NPD6925	Approved
0.7368	Intermediate Similarity	NPD6923	Approved
0.7368	Intermediate Similarity	NPD6922	Approved
0.7356	Intermediate Similarity	NPD5328	Approved
0.7349	Intermediate Similarity	NPD3667	Approved
0.7294	Intermediate Similarity	NPD6893	Approved
0.7284	Intermediate Similarity	NPD7145	Approved
0.7273	Intermediate Similarity	NPD7143	Approved
0.7273	Intermediate Similarity	NPD7144	Approved
0.7246	Intermediate Similarity	NPD342	Phase 1
0.7229	Intermediate Similarity	NPD6902	Approved
0.7229	Intermediate Similarity	NPD6898	Phase 1
0.7204	Intermediate Similarity	NPD7640	Approved
0.7204	Intermediate Similarity	NPD7639	Approved
0.7191	Intermediate Similarity	NPD6079	Approved
0.7191	Intermediate Similarity	NPD7515	Phase 2
0.716	Intermediate Similarity	NPD6932	Approved
0.7126	Intermediate Similarity	NPD7750	Discontinued
0.7126	Intermediate Similarity	NPD7524	Approved
0.7125	Intermediate Similarity	NPD5275	Approved
0.7125	Intermediate Similarity	NPD4190	Phase 3
0.7111	Intermediate Similarity	NPD4202	Approved
0.7108	Intermediate Similarity	NPD4748	Discontinued
0.7097	Intermediate Similarity	NPD7638	Approved
0.7011	Intermediate Similarity	NPD4519	Discontinued
0.7011	Intermediate Similarity	NPD4623	Approved
0.6988	Remote Similarity	NPD4195	Approved
0.6988	Remote Similarity	NPD6683	Phase 2
0.6977	Remote Similarity	NPD3666	Approved
0.6977	Remote Similarity	NPD3133	Approved
0.6977	Remote Similarity	NPD3665	Phase 1
0.6915	Remote Similarity	NPD4225	Approved
0.6897	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5211	Phase 2
0.6848	Remote Similarity	NPD7748	Approved
0.6813	Remote Similarity	NPD7087	Discontinued
0.6809	Remote Similarity	NPD4755	Approved
0.6778	Remote Similarity	NPD4753	Phase 2
0.6744	Remote Similarity	NPD4221	Approved
0.6744	Remote Similarity	NPD4223	Phase 3
0.6735	Remote Similarity	NPD5141	Approved
0.6709	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1696	Phase 3
0.6705	Remote Similarity	NPD5329	Approved
0.6702	Remote Similarity	NPD4697	Phase 3
0.6702	Remote Similarity	NPD5222	Approved
0.6702	Remote Similarity	NPD5221	Approved
0.6702	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD4219	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6632	Remote Similarity	NPD7902	Approved
0.6632	Remote Similarity	NPD5173	Approved
0.6629	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5223	Approved
0.6593	Remote Similarity	NPD6051	Approved
0.6591	Remote Similarity	NPD4197	Approved
0.6591	Remote Similarity	NPD3668	Phase 3
0.6562	Remote Similarity	NPD5290	Discontinued
0.6559	Remote Similarity	NPD6399	Phase 3
0.6531	Remote Similarity	NPD5224	Approved
0.6531	Remote Similarity	NPD5226	Approved
0.6531	Remote Similarity	NPD5225	Approved
0.6531	Remote Similarity	NPD7632	Discontinued
0.6531	Remote Similarity	NPD4633	Approved
0.6512	Remote Similarity	NPD4695	Discontinued
0.65	Remote Similarity	NPD6402	Approved
0.65	Remote Similarity	NPD7128	Approved
0.65	Remote Similarity	NPD6675	Approved
0.65	Remote Similarity	NPD5739	Approved
0.6465	Remote Similarity	NPD5175	Approved
0.6465	Remote Similarity	NPD4754	Approved
0.6465	Remote Similarity	NPD5174	Approved
0.6463	Remote Similarity	NPD4732	Discontinued
0.6458	Remote Similarity	NPD6084	Phase 2
0.6458	Remote Similarity	NPD6083	Phase 2
0.6452	Remote Similarity	NPD7637	Suspended
0.6444	Remote Similarity	NPD4693	Phase 3
0.6444	Remote Similarity	NPD4689	Approved
0.6444	Remote Similarity	NPD5205	Approved
0.6444	Remote Similarity	NPD4688	Approved
0.6444	Remote Similarity	NPD4138	Approved
0.6444	Remote Similarity	NPD4690	Approved
0.6444	Remote Similarity	NPD5279	Phase 3
0.6429	Remote Similarity	NPD4159	Approved
0.6421	Remote Similarity	NPD4629	Approved
0.6421	Remote Similarity	NPD5210	Approved
0.642	Remote Similarity	NPD4787	Phase 1
0.6374	Remote Similarity	NPD3573	Approved
0.6373	Remote Similarity	NPD7320	Approved
0.6373	Remote Similarity	NPD6899	Approved
0.6373	Remote Similarity	NPD6881	Approved
0.6364	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD7115	Discovery
0.6344	Remote Similarity	NPD7136	Phase 2
0.6337	Remote Similarity	NPD4768	Approved
0.6337	Remote Similarity	NPD4767	Approved
0.6316	Remote Similarity	NPD7900	Approved
0.6316	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6372	Approved
0.6311	Remote Similarity	NPD6373	Approved
0.6304	Remote Similarity	NPD4722	Approved
0.6304	Remote Similarity	NPD4723	Approved
0.6279	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3617	Approved
0.6277	Remote Similarity	NPD8034	Phase 2
0.6277	Remote Similarity	NPD8035	Phase 2
0.6275	Remote Similarity	NPD5697	Approved
0.6275	Remote Similarity	NPD5701	Approved
0.6264	Remote Similarity	NPD7146	Approved
0.6264	Remote Similarity	NPD5330	Approved
0.6264	Remote Similarity	NPD7521	Approved
0.6264	Remote Similarity	NPD4694	Approved
0.6264	Remote Similarity	NPD7334	Approved
0.6264	Remote Similarity	NPD6409	Approved
0.6264	Remote Similarity	NPD6684	Approved
0.6264	Remote Similarity	NPD5280	Approved
0.6264	Remote Similarity	NPD5690	Phase 2
0.6263	Remote Similarity	NPD5344	Discontinued
0.625	Remote Similarity	NPD7102	Approved
0.625	Remote Similarity	NPD7290	Approved
0.625	Remote Similarity	NPD6883	Approved
0.6214	Remote Similarity	NPD5128	Approved
0.6214	Remote Similarity	NPD4730	Approved
0.6214	Remote Similarity	NPD6011	Approved
0.6214	Remote Similarity	NPD4729	Approved
0.6211	Remote Similarity	NPD5778	Approved
0.6211	Remote Similarity	NPD5779	Approved
0.619	Remote Similarity	NPD6650	Approved
0.619	Remote Similarity	NPD8130	Phase 1
0.619	Remote Similarity	NPD6847	Approved
0.619	Remote Similarity	NPD6869	Approved
0.619	Remote Similarity	NPD6649	Approved
0.619	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6617	Approved
0.6176	Remote Similarity	NPD4265	Approved
0.6154	Remote Similarity	NPD6012	Approved
0.6154	Remote Similarity	NPD6013	Approved
0.6154	Remote Similarity	NPD6014	Approved
0.6147	Remote Similarity	NPD7328	Approved
0.6147	Remote Similarity	NPD7327	Approved
0.6145	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4822	Approved
0.6136	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4820	Approved
0.6136	Remote Similarity	NPD4819	Approved
0.6136	Remote Similarity	NPD4821	Approved
0.6132	Remote Similarity	NPD8297	Approved
0.6132	Remote Similarity	NPD6882	Approved
0.6129	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6903	Approved
0.6129	Remote Similarity	NPD6672	Approved
0.6129	Remote Similarity	NPD5737	Approved
0.6105	Remote Similarity	NPD6411	Approved
0.6098	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4634	Approved
0.6095	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5169	Approved
0.6095	Remote Similarity	NPD5248	Approved
0.6095	Remote Similarity	NPD5135	Approved
0.6095	Remote Similarity	NPD5249	Phase 3
0.6095	Remote Similarity	NPD5247	Approved
0.6095	Remote Similarity	NPD5250	Approved
0.6095	Remote Similarity	NPD5251	Approved
0.6091	Remote Similarity	NPD7516	Approved
0.6087	Remote Similarity	NPD384	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