NPASS Compound

Structure

NPC474316 OpenBabel07101719142D 24 25 0 0 1 0 0 0 0 0999 V2000 3.0567 -1.9836 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 4.4709 1.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5050 1.1037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7355 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4368 -0.8282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7297 -1.5353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 -0.0517 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 5.1780 0.1378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8320 -0.7588 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 3.7638 -1.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5050 -0.3105 0.0000 C 0 0 3 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 0 0 0 0 0 0 0 0 0 0 4.2121 0.3966 0.0000 C 0 0 0 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 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 22 1 0 0 0 0 7 8 1 0 0 0 0 7 11 1 0 0 0 0 8 14 1 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 15 2 1 1 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 15 1 6 0 0 0 17 23 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 20 5 1 1 0 0 0 20 24 1 0 0 0 0 23 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.25
Volume:	367.251
LogP:	4.731
LogD:	4.074
LogS:	-5.597
# Rotatable Bonds:	6
TPSA:	44.76
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.409
Synthetic Accessibility Score:	4.522
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.694
MDCK Permeability:	2.2260999685386196e-05
Pgp-inhibitor:	0.314
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.044

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.425
Plasma Protein Binding (PPB):	70.89403533935547%
Volume Distribution (VD):	1.581
Pgp-substrate:	26.972209930419922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.098
CYP1A2-substrate:	0.688
CYP2C19-inhibitor:	0.367
CYP2C19-substrate:	0.933
CYP2C9-inhibitor:	0.358
CYP2C9-substrate:	0.633
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.692
CYP3A4-substrate:	0.368

ADMET: Excretion

Clearance (CL):	4.993
Half-life (T1/2):	0.09

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.513
Drug-inuced Liver Injury (DILI):	0.691
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.085
Carcinogencity:	0.072
Eye Corrosion:	0.012
Eye Irritation:	0.071
Respiratory Toxicity:	0.897

Download Data

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

Natural Product: NPC474316

Natural Product ID:	NPC474316
*Common Name:**	Nuapapuin B
IUPAC Name:	methyl (2R)-2-[(3R,6R)-6-[2-(2,2-dimethyl-6-methylidenecyclohexyl)ethyl]-6-methyldioxan-3-yl]propanoate
Synonyms:	(+)-Nuapapuin B Methyl Ester
Standard InCHIKey:	MYBJZJMUOIRKIX-CYXPSIDGSA-N
Standard InCHI:	InChI=1S/C20H34O4/c1-14-8-7-11-19(3,4)16(14)9-12-20(5)13-10-17(23-24-20)15(2)18(21)22-6/h15-17H,1,7-13H2,2-6H3/t15-,16?,17-,20-/m1/s1
SMILES:	COC(=O)[C@@H]([C@H]1CC[C@@](OO1)(C)CCC1C(=C)CCCC1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465146
PubChem CID:	10783228
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO4211	Negombata corticata	Species	Latrunculiidae	Eukaryota	n.a.	formosan	n.a.	PMID[20718475]
NPO40711	Diacarnus cf. spinopoculum	Strain	Podospongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9514009]
NPO4211	Negombata corticata	Species	Latrunculiidae	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	68
IC50	5
Others	5

Activity Type	# Activity
Cell Line	70
NON-MOLECULAR	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	1600.0	nM	PMID[454627]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	>	5000.0	nM	PMID[454627]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	640.0	nM	PMID[454627]
NPT386	Cell Line	KM12	Homo sapiens	GI50	=	400.0	nM	PMID[454627]
NPT401	Cell Line	786-0	Homo sapiens	GI50	=	270.0	nM	PMID[454627]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	=	4950.0	nM	PMID[454627]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	=	1270.0	nM	PMID[454628]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	1600.0	nM	PMID[454628]
NPT111	Cell Line	K562	Homo sapiens	GI50	=	6380.0	nM	PMID[454628]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	=	7040.0	nM	PMID[454628]
NPT385	Cell Line	SR	Homo sapiens	GI50	=	2170.0	nM	PMID[454628]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	640.0	nM	PMID[454628]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	=	7900.0	nM	PMID[454628]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	=	710.0	nM	PMID[454628]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	=	760.0	nM	PMID[454628]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	=	6170.0	nM	PMID[454628]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	=	3540.0	nM	PMID[454628]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	=	6900.0	nM	PMID[454628]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	910.0	nM	PMID[454628]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	=	3050.0	nM	PMID[454628]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	=	4540.0	nM	PMID[454628]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	=	3680.0	nM	PMID[454628]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	=	8140.0	nM	PMID[454628]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	=	13100.0	nM	PMID[454628]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	380.0	nM	PMID[454628]
NPT386	Cell Line	KM12	Homo sapiens	GI50	=	400.0	nM	PMID[454628]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	=	7530.0	nM	PMID[454628]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	3190.0	nM	PMID[454628]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	=	4420.0	nM	PMID[454628]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	=	6250.0	nM	PMID[454628]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	=	5470.0	nM	PMID[454628]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	=	2670.0	nM	PMID[454628]
NPT380	Cell Line	U-251	Homo sapiens	GI50	=	2910.0	nM	PMID[454628]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	=	470.0	nM	PMID[454628]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	=	21000.0	nM	PMID[454628]
NPT387	Cell Line	M14	Homo sapiens	GI50	=	6430.0	nM	PMID[454628]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	=	8280.0	nM	PMID[454628]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	=	20600.0	nM	PMID[454628]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	=	3940.0	nM	PMID[454628]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	=	16300.0	nM	PMID[454628]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	=	4130.0	nM	PMID[454628]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	=	500.0	nM	PMID[454628]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	=	21800.0	nM	PMID[454628]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	=	4010.0	nM	PMID[454628]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	=	4760.0	nM	PMID[454628]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	=	5760.0	nM	PMID[454628]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	=	4400.0	nM	PMID[454628]
NPT401	Cell Line	786-0	Homo sapiens	GI50	=	270.0	nM	PMID[454628]
NPT376	Cell Line	A498	Homo sapiens	GI50	=	4920.0	nM	PMID[454628]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	=	480.0	nM	PMID[454628]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	=	320.0	nM	PMID[454628]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	=	2620.0	nM	PMID[454628]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	=	3730.0	nM	PMID[454628]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	=	4210.0	nM	PMID[454628]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	=	520.0	nM	PMID[454628]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	3630.0	nM	PMID[454628]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	3670.0	nM	PMID[454628]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	18400.0	nM	PMID[454628]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	757000.0	nM	PMID[454628]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	=	4340.0	nM	PMID[454628]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	=	3540.0	nM	PMID[454628]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	=	4950.0	nM	PMID[454628]
NPT396	Cell Line	T47D	Homo sapiens	GI50	=	2940.0	nM	PMID[454628]
NPT137	Cell Line	L1210	Mus musculus	Activity	=	180.0	Zone units	PMID[454628]
NPT730	Cell Line	MC-38	Mus musculus	Activity	=	300.0	Zone units	PMID[454628]
NPT168	Cell Line	P388	Mus musculus	Activity	=	180.0	Zone units	PMID[454628]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	3500.0	nM	PMID[454629]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	38500.0	nM	PMID[454629]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	2900.0	nM	PMID[454629]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5380.0	nM	PMID[454629]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	500.0	nM	PMID[454627]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	470.0	nM	PMID[454627]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	4040.0	nM	PMID[454628]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	4600.0	nM	PMID[454628]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	100.0	Zone units	PMID[454628]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	200.0	Zone units	PMID[454628]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	23700.0	nM	PMID[454629]
NPT2	Others	Unspecified		GI50	=	5670	nM	PubChem BioAssay data set

☑ 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 NPC474316 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	203
0.1-0.2	1721
0.2-0.3	6863
0.3-0.4	15602
0.4-0.5	6881
0.5-0.6	7416
0.6-0.7	3650
0.7-0.8	315
0.8-0.85	19
0.85-0.9	17
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475744
1.0	High Similarity	NPC476985
0.9459	High Similarity	NPC274522
0.9459	High Similarity	NPC476265
0.9452	High Similarity	NPC470905
0.9452	High Similarity	NPC476986
0.9211	High Similarity	NPC475395
0.9211	High Similarity	NPC476984
0.9079	High Similarity	NPC476988
0.9054	High Similarity	NPC469867
0.8961	High Similarity	NPC474605
0.8961	High Similarity	NPC476292
0.8919	High Similarity	NPC59602
0.8919	High Similarity	NPC152754
0.8919	High Similarity	NPC476987
0.88	High Similarity	NPC476325
0.88	High Similarity	NPC476264
0.875	High Similarity	NPC476104
0.8625	High Similarity	NPC471344
0.859	High Similarity	NPC14044
0.859	High Similarity	NPC117960
0.859	High Similarity	NPC172309
0.8571	High Similarity	NPC254996
0.8571	High Similarity	NPC268502
0.8519	High Similarity	NPC262085
0.85	High Similarity	NPC475193
0.85	High Similarity	NPC120158
0.8434	Intermediate Similarity	NPC469866
0.8434	Intermediate Similarity	NPC471342
0.84	Intermediate Similarity	NPC330016
0.8375	Intermediate Similarity	NPC476100
0.8375	Intermediate Similarity	NPC476983
0.8333	Intermediate Similarity	NPC308545
0.8333	Intermediate Similarity	NPC82488
0.8312	Intermediate Similarity	NPC122847
0.8267	Intermediate Similarity	NPC167145
0.8182	Intermediate Similarity	NPC474447
0.8125	Intermediate Similarity	NPC475951
0.8072	Intermediate Similarity	NPC475181
0.8072	Intermediate Similarity	NPC476982
0.8056	Intermediate Similarity	NPC306805
0.8056	Intermediate Similarity	NPC215987
0.8049	Intermediate Similarity	NPC471343
0.8	Intermediate Similarity	NPC472021
0.7949	Intermediate Similarity	NPC469514
0.7949	Intermediate Similarity	NPC239127
0.7857	Intermediate Similarity	NPC472020
0.7857	Intermediate Similarity	NPC472019
0.7857	Intermediate Similarity	NPC226602
0.7848	Intermediate Similarity	NPC474433
0.7838	Intermediate Similarity	NPC469868
0.7821	Intermediate Similarity	NPC255060
0.7792	Intermediate Similarity	NPC238425
0.7792	Intermediate Similarity	NPC474543
0.7792	Intermediate Similarity	NPC472018
0.7791	Intermediate Similarity	NPC253618
0.7791	Intermediate Similarity	NPC77001
0.7778	Intermediate Similarity	NPC170038
0.7765	Intermediate Similarity	NPC134197
0.7763	Intermediate Similarity	NPC91369
0.775	Intermediate Similarity	NPC321514
0.775	Intermediate Similarity	NPC121200
0.7733	Intermediate Similarity	NPC36616
0.7733	Intermediate Similarity	NPC290445
0.7692	Intermediate Similarity	NPC474551
0.7683	Intermediate Similarity	NPC79277
0.7683	Intermediate Similarity	NPC327002
0.7683	Intermediate Similarity	NPC475481
0.7674	Intermediate Similarity	NPC255176
0.7662	Intermediate Similarity	NPC72343
0.7654	Intermediate Similarity	NPC28319
0.7654	Intermediate Similarity	NPC118987
0.7625	Intermediate Similarity	NPC281296
0.7619	Intermediate Similarity	NPC469407
0.7614	Intermediate Similarity	NPC476934
0.7595	Intermediate Similarity	NPC474419
0.7564	Intermediate Similarity	NPC279241
0.7534	Intermediate Similarity	NPC474552
0.7532	Intermediate Similarity	NPC69462
0.75	Intermediate Similarity	NPC471037
0.75	Intermediate Similarity	NPC476601
0.75	Intermediate Similarity	NPC170862
0.75	Intermediate Similarity	NPC266119
0.75	Intermediate Similarity	NPC92489
0.7471	Intermediate Similarity	NPC211162
0.7471	Intermediate Similarity	NPC56413
0.7471	Intermediate Similarity	NPC183374
0.7468	Intermediate Similarity	NPC166797
0.7468	Intermediate Similarity	NPC46610
0.7468	Intermediate Similarity	NPC18819
0.7442	Intermediate Similarity	NPC73038
0.7439	Intermediate Similarity	NPC192999
0.7439	Intermediate Similarity	NPC476438
0.7439	Intermediate Similarity	NPC471475
0.7439	Intermediate Similarity	NPC327674
0.7416	Intermediate Similarity	NPC36491
0.7416	Intermediate Similarity	NPC471901
0.7412	Intermediate Similarity	NPC100391
0.7407	Intermediate Similarity	NPC238227
0.7403	Intermediate Similarity	NPC107130
0.7391	Intermediate Similarity	NPC253586
0.7386	Intermediate Similarity	NPC471043
0.7386	Intermediate Similarity	NPC57954
0.7386	Intermediate Similarity	NPC213832
0.7386	Intermediate Similarity	NPC474679
0.7381	Intermediate Similarity	NPC123880
0.7381	Intermediate Similarity	NPC476935
0.7381	Intermediate Similarity	NPC471159
0.7375	Intermediate Similarity	NPC199445
0.7375	Intermediate Similarity	NPC60718
0.7363	Intermediate Similarity	NPC205173
0.7363	Intermediate Similarity	NPC217329
0.7349	Intermediate Similarity	NPC469920
0.7333	Intermediate Similarity	NPC199543
0.7333	Intermediate Similarity	NPC476330
0.7333	Intermediate Similarity	NPC473690
0.7333	Intermediate Similarity	NPC287118
0.7333	Intermediate Similarity	NPC471902
0.7326	Intermediate Similarity	NPC98270
0.7326	Intermediate Similarity	NPC329738
0.7326	Intermediate Similarity	NPC201655
0.7326	Intermediate Similarity	NPC76333
0.7317	Intermediate Similarity	NPC269543
0.7317	Intermediate Similarity	NPC4827
0.7317	Intermediate Similarity	NPC247783
0.7317	Intermediate Similarity	NPC63020
0.7317	Intermediate Similarity	NPC35574
0.7312	Intermediate Similarity	NPC474793
0.7308	Intermediate Similarity	NPC472017
0.7294	Intermediate Similarity	NPC475989
0.7294	Intermediate Similarity	NPC243347
0.7294	Intermediate Similarity	NPC69469
0.7294	Intermediate Similarity	NPC477373
0.7284	Intermediate Similarity	NPC899
0.7283	Intermediate Similarity	NPC132824
0.7273	Intermediate Similarity	NPC48824
0.7273	Intermediate Similarity	NPC146937
0.7273	Intermediate Similarity	NPC254572
0.7273	Intermediate Similarity	NPC229407
0.7273	Intermediate Similarity	NPC80335
0.7273	Intermediate Similarity	NPC250687
0.7273	Intermediate Similarity	NPC471900
0.7262	Intermediate Similarity	NPC223330
0.7262	Intermediate Similarity	NPC232625
0.7262	Intermediate Similarity	NPC476101
0.7262	Intermediate Similarity	NPC209318
0.7262	Intermediate Similarity	NPC14203
0.7262	Intermediate Similarity	NPC229584
0.7253	Intermediate Similarity	NPC471078
0.7253	Intermediate Similarity	NPC473435
0.7253	Intermediate Similarity	NPC469982
0.7253	Intermediate Similarity	NPC473280
0.7253	Intermediate Similarity	NPC78580
0.7253	Intermediate Similarity	NPC473431
0.7253	Intermediate Similarity	NPC184006
0.7253	Intermediate Similarity	NPC23621
0.725	Intermediate Similarity	NPC306928
0.7241	Intermediate Similarity	NPC80590
0.7241	Intermediate Similarity	NPC472505
0.7241	Intermediate Similarity	NPC475753
0.7241	Intermediate Similarity	NPC475007
0.7241	Intermediate Similarity	NPC322159
0.7241	Intermediate Similarity	NPC324063
0.7241	Intermediate Similarity	NPC471042
0.7241	Intermediate Similarity	NPC185638
0.7234	Intermediate Similarity	NPC108371
0.7229	Intermediate Similarity	NPC113363
0.7229	Intermediate Similarity	NPC263951
0.7222	Intermediate Similarity	NPC228784
0.7222	Intermediate Similarity	NPC471588
0.7222	Intermediate Similarity	NPC288833
0.7222	Intermediate Similarity	NPC966
0.7222	Intermediate Similarity	NPC324341
0.7222	Intermediate Similarity	NPC282616
0.7222	Intermediate Similarity	NPC6255
0.7222	Intermediate Similarity	NPC475416
0.7222	Intermediate Similarity	NPC470230
0.7222	Intermediate Similarity	NPC155120
0.7215	Intermediate Similarity	NPC40327
0.7209	Intermediate Similarity	NPC263974
0.7209	Intermediate Similarity	NPC475509
0.7195	Intermediate Similarity	NPC66105
0.7195	Intermediate Similarity	NPC472300
0.7191	Intermediate Similarity	NPC24772
0.7191	Intermediate Similarity	NPC474570
0.7191	Intermediate Similarity	NPC116146
0.7191	Intermediate Similarity	NPC474700
0.7191	Intermediate Similarity	NPC269267
0.7191	Intermediate Similarity	NPC97577
0.7176	Intermediate Similarity	NPC240302
0.7174	Intermediate Similarity	NPC210214
0.7174	Intermediate Similarity	NPC322188
0.7174	Intermediate Similarity	NPC23241
0.7174	Intermediate Similarity	NPC195715
0.716	Intermediate Similarity	NPC471491
0.716	Intermediate Similarity	NPC475861
0.7159	Intermediate Similarity	NPC173089
0.7159	Intermediate Similarity	NPC46912
0.7159	Intermediate Similarity	NPC162107
0.7159	Intermediate Similarity	NPC158141

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 NPC474316 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	2260
0.2-0.3	3972
0.3-0.4	1816
0.4-0.5	471
0.5-0.6	294
0.6-0.7	127
0.7-0.8	8
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
0.7416	Intermediate Similarity	NPD6411	Approved
0.7191	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6101	Approved
0.7045	Intermediate Similarity	NPD7521	Approved
0.7045	Intermediate Similarity	NPD7334	Approved
0.7045	Intermediate Similarity	NPD6684	Approved
0.7045	Intermediate Similarity	NPD5330	Approved
0.7045	Intermediate Similarity	NPD6409	Approved
0.7045	Intermediate Similarity	NPD7146	Approved
0.7033	Intermediate Similarity	NPD8035	Phase 2
0.7033	Intermediate Similarity	NPD8034	Phase 2
0.6977	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6399	Phase 3
0.6932	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6903	Approved
0.6889	Remote Similarity	NPD6672	Approved
0.6889	Remote Similarity	NPD5737	Approved
0.6889	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7900	Approved
0.6882	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5779	Approved
0.6774	Remote Similarity	NPD5778	Approved
0.6702	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD7515	Phase 2
0.6632	Remote Similarity	NPD5695	Phase 3
0.663	Remote Similarity	NPD6673	Approved
0.663	Remote Similarity	NPD6080	Approved
0.663	Remote Similarity	NPD6904	Approved
0.6593	Remote Similarity	NPD3573	Approved
0.6585	Remote Similarity	NPD5777	Approved
0.6569	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD8039	Approved
0.6535	Remote Similarity	NPD6402	Approved
0.6535	Remote Similarity	NPD5739	Approved
0.6535	Remote Similarity	NPD7128	Approved
0.6535	Remote Similarity	NPD6675	Approved
0.6526	Remote Similarity	NPD5282	Discontinued
0.6517	Remote Similarity	NPD4788	Approved
0.6489	Remote Similarity	NPD7637	Suspended
0.6489	Remote Similarity	NPD6050	Approved
0.6458	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD3668	Phase 3
0.6444	Remote Similarity	NPD4786	Approved
0.6429	Remote Similarity	NPD5696	Approved
0.642	Remote Similarity	NPD229	Approved
0.6408	Remote Similarity	NPD6686	Approved
0.6408	Remote Similarity	NPD6899	Approved
0.6408	Remote Similarity	NPD7320	Approved
0.6408	Remote Similarity	NPD6881	Approved
0.6404	Remote Similarity	NPD3667	Approved
0.6404	Remote Similarity	NPD6435	Approved
0.6395	Remote Similarity	NPD6116	Phase 1
0.6383	Remote Similarity	NPD5692	Phase 3
0.6374	Remote Similarity	NPD1694	Approved
0.6364	Remote Similarity	NPD5368	Approved
0.6353	Remote Similarity	NPD3702	Approved
0.6346	Remote Similarity	NPD6372	Approved
0.6346	Remote Similarity	NPD6373	Approved
0.6344	Remote Similarity	NPD5208	Approved
0.6322	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5281	Approved
0.6316	Remote Similarity	NPD5694	Approved
0.6316	Remote Similarity	NPD5284	Approved
0.6316	Remote Similarity	NPD5693	Phase 1
0.6311	Remote Similarity	NPD5697	Approved
0.6311	Remote Similarity	NPD5701	Approved
0.6304	Remote Similarity	NPD6422	Discontinued
0.6289	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7290	Approved
0.6286	Remote Similarity	NPD6883	Approved
0.6286	Remote Similarity	NPD7102	Approved
0.6279	Remote Similarity	NPD6117	Approved
0.6277	Remote Similarity	NPD4753	Phase 2
0.6277	Remote Similarity	NPD6051	Approved
0.6264	Remote Similarity	NPD3133	Approved
0.6264	Remote Similarity	NPD3666	Approved
0.6264	Remote Similarity	NPD3665	Phase 1
0.6263	Remote Similarity	NPD4225	Approved
0.6262	Remote Similarity	NPD8133	Approved
0.6235	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6617	Approved
0.6226	Remote Similarity	NPD6650	Approved
0.6226	Remote Similarity	NPD8130	Phase 1
0.6226	Remote Similarity	NPD6649	Approved
0.6226	Remote Similarity	NPD6869	Approved
0.6226	Remote Similarity	NPD6847	Approved
0.6222	Remote Similarity	NPD4269	Approved
0.6222	Remote Similarity	NPD4270	Approved
0.6216	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6008	Approved
0.6211	Remote Similarity	NPD6698	Approved
0.6211	Remote Similarity	NPD5785	Approved
0.6211	Remote Similarity	NPD5207	Approved
0.6211	Remote Similarity	NPD46	Approved
0.619	Remote Similarity	NPD6014	Approved
0.619	Remote Similarity	NPD6012	Approved
0.619	Remote Similarity	NPD6013	Approved
0.618	Remote Similarity	NPD4822	Approved
0.618	Remote Similarity	NPD4695	Discontinued
0.618	Remote Similarity	NPD4819	Approved
0.618	Remote Similarity	NPD4821	Approved
0.618	Remote Similarity	NPD4820	Approved
0.6168	Remote Similarity	NPD8297	Approved
0.6168	Remote Similarity	NPD6882	Approved
0.6162	Remote Similarity	NPD4755	Approved
0.6154	Remote Similarity	NPD5362	Discontinued
0.6154	Remote Similarity	NPD7154	Phase 3
0.6154	Remote Similarity	NPD6412	Phase 2
0.6146	Remote Similarity	NPD7983	Approved
0.6136	Remote Similarity	NPD6697	Approved
0.6136	Remote Similarity	NPD6115	Approved
0.6136	Remote Similarity	NPD6118	Approved
0.6136	Remote Similarity	NPD6114	Approved
0.6129	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5786	Approved
0.6129	Remote Similarity	NPD3618	Phase 1
0.6129	Remote Similarity	NPD5279	Phase 3
0.6105	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5328	Approved
0.61	Remote Similarity	NPD7638	Approved
0.6095	Remote Similarity	NPD6011	Approved
0.6091	Remote Similarity	NPD7115	Discovery
0.6087	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4202	Approved
0.6075	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7839	Suspended
0.6061	Remote Similarity	NPD7732	Phase 3
0.6061	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD6926	Approved
0.6047	Remote Similarity	NPD6924	Approved
0.6044	Remote Similarity	NPD4221	Approved
0.6044	Remote Similarity	NPD4223	Phase 3
0.6044	Remote Similarity	NPD5209	Approved
0.604	Remote Similarity	NPD4700	Approved
0.604	Remote Similarity	NPD5286	Approved
0.604	Remote Similarity	NPD7639	Approved
0.604	Remote Similarity	NPD4696	Approved
0.604	Remote Similarity	NPD5285	Approved
0.604	Remote Similarity	NPD7640	Approved
0.6038	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD5329	Approved
0.6022	Remote Similarity	NPD5363	Approved
0.602	Remote Similarity	NPD6001	Approved
0.6	Remote Similarity	NPD7525	Registered
0.6	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4252	Approved
0.6	Remote Similarity	NPD6081	Approved
0.5981	Remote Similarity	NPD6371	Approved
0.5979	Remote Similarity	NPD6079	Approved
0.5978	Remote Similarity	NPD6695	Phase 3
0.5976	Remote Similarity	NPD4224	Phase 2
0.596	Remote Similarity	NPD5654	Approved
0.596	Remote Similarity	NPD4629	Approved
0.596	Remote Similarity	NPD5210	Approved
0.5955	Remote Similarity	NPD4802	Phase 2
0.5955	Remote Similarity	NPD4271	Approved
0.5955	Remote Similarity	NPD4238	Approved
0.5955	Remote Similarity	NPD4268	Approved
0.5952	Remote Similarity	NPD3726	Approved
0.5952	Remote Similarity	NPD3725	Approved
0.5946	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD1695	Approved
0.5934	Remote Similarity	NPD1780	Approved
0.5934	Remote Similarity	NPD1779	Approved
0.5929	Remote Similarity	NPD6319	Approved
0.5922	Remote Similarity	NPD5211	Phase 2
0.5922	Remote Similarity	NPD5226	Approved
0.5922	Remote Similarity	NPD5224	Approved
0.5922	Remote Similarity	NPD5225	Approved
0.5922	Remote Similarity	NPD4633	Approved
0.5914	Remote Similarity	NPD4197	Approved
0.5913	Remote Similarity	NPD8328	Phase 3
0.5909	Remote Similarity	NPD6933	Approved
0.5889	Remote Similarity	NPD7645	Phase 2
0.5888	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4244	Approved
0.5882	Remote Similarity	NPD4245	Approved
0.5877	Remote Similarity	NPD6921	Approved
0.5865	Remote Similarity	NPD5174	Approved
0.5865	Remote Similarity	NPD6052	Approved
0.5865	Remote Similarity	NPD5175	Approved
0.5862	Remote Similarity	NPD7492	Approved
0.5856	Remote Similarity	NPD6274	Approved
0.5854	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD7341	Phase 2
0.5849	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5959	Approved
0.5841	Remote Similarity	NPD7100	Approved
0.5841	Remote Similarity	NPD7101	Approved
0.5833	Remote Similarity	NPD4634	Approved
0.5833	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5223	Approved
0.5824	Remote Similarity	NPD7509	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