NPASS Compound

Structure

NPC100257 OpenBabel07101719152D 25 29 0 0 1 0 0 0 0 0999 V2000 4.1886 1.0087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0340 -2.1637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3086 0.1777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9697 2.0780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2525 -0.2607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2888 -1.3221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3527 -0.7695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2077 -0.0218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9178 -0.9714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2137 0.8315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7113 1.3520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6195 0.6997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2376 0.6997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6707 -0.9528 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9285 -0.2514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4319 -0.5762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0174 -1.1650 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3104 0.1179 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9285 -0.2514 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4285 1.2874 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6814 -0.2327 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5163 -1.0604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4318 -0.5612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9709 2.1276 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 13 2 0 0 0 0 3 18 1 0 0 0 0 4 24 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 17 1 0 0 0 0 8 21 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 17 1 6 0 0 0 14 21 1 0 0 0 0 15 19 1 0 0 0 0 15 22 2 0 0 0 0 16 17 1 0 0 0 0 16 23 2 0 0 0 0 16 25 1 0 0 0 0 17 2 1 6 0 0 0 18 19 1 1 0 0 0 19 9 1 6 0 0 0 20 24 1 6 0 0 0 21 18 1 6 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.2
Volume:	356.241
LogP:	2.066
LogD:	1.68
LogS:	-4.803
# Rotatable Bonds:	1
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.539
Synthetic Accessibility Score:	6.383
Fsp3:	0.81
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.015
MDCK Permeability:	2.6837698896997608e-05
Pgp-inhibitor:	0.129
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.111

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.099
Plasma Protein Binding (PPB):	83.54828643798828%
Volume Distribution (VD):	0.803
Pgp-substrate:	16.03146743774414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.98
CYP2C19-inhibitor:	0.119
CYP2C19-substrate:	0.872
CYP2C9-inhibitor:	0.124
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.903
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	6.088
Half-life (T1/2):	0.104

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.535
Drug-inuced Liver Injury (DILI):	0.127
AMES Toxicity:	0.124
Rat Oral Acute Toxicity:	0.887
Maximum Recommended Daily Dose:	0.859
Skin Sensitization:	0.12
Carcinogencity:	0.879
Eye Corrosion:	0.013
Eye Irritation:	0.021
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC100257

Natural Product ID:	NPC100257
*Common Name:**	UCXBBKCPRLOQQA-HQHFYQKISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UCXBBKCPRLOQQA-HQHFYQKISA-N
Standard InCHI:	InChI=1S/C21H28O4/c1-13-15(22)19-9-6-14-17(2)7-5-8-21(14,25-16(17)23)18(19,3)10-11-20(13,12-19)24-4/h14H,1,5-12H2,2-4H3/t14-,17-,18+,19+,20+,21+/m1/s1
SMILES:	C=C1C(=O)[C@]23CC[C@@H]4[C@@]5(C)CCC[C@]4([C@@]3(C)CC[C@@]1(C2)OC)OC5=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465475
PubChem CID:	10315488
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO26247	Parinari capensis	Species	Chrysobalanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12127529]
NPO26247	Parinari capensis	Species	Chrysobalanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO26247	Parinari capensis	Species	Chrysobalanaceae	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
IC50	12
Others	20

Activity Type	# Activity
Cell Line	22
NON-MOLECULAR	2
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1851	Cell Line	Col2	Homo sapiens	IC50	=	3800.0	nM	PMID[568185]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	6400.0	nM	PMID[568185]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	1200.0	nM	PMID[568185]
NPT1034	Cell Line	Lu1	Homo sapiens	IC50	=	2000.0	nM	PMID[568185]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	900.0	nM	PMID[568185]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	1200.0	nM	PMID[568185]
NPT168	Cell Line	P388	Mus musculus	IC50	=	300.0	nM	PMID[568185]
NPT2345	Cell Line	SW626	Homo sapiens	IC50	=	600.0	nM	PMID[568185]
NPT1034	Cell Line	Lu1	Homo sapiens	Inhibition	=	0.0	%	PMID[568185]
NPT2345	Cell Line	SW626	Homo sapiens	Inhibition	=	0.0	%	PMID[568185]
NPT858	Cell Line	LNCaP	Homo sapiens	Inhibition	=	50.6	%	PMID[568185]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	Inhibition	=	15.5	%	PMID[568185]
NPT91	Cell Line	KB	Homo sapiens	Inhibition	=	21.6	%	PMID[568185]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	34.4	%	PMID[568185]
NPT168	Cell Line	P388	Mus musculus	Inhibition	=	0.0	%	PMID[568185]
NPT2345	Cell Line	SW626	Homo sapiens	Inhibition	=	16.3	%	PMID[568185]
NPT858	Cell Line	LNCaP	Homo sapiens	Inhibition	=	0.0	%	PMID[568185]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	Inhibition	=	11.1	%	PMID[568185]
NPT91	Cell Line	KB	Homo sapiens	Inhibition	=	5.7	%	PMID[568185]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	0.0	%	PMID[568185]
NPT2	Others	Unspecified		IC50	=	0.67	ug.mL-1	PMID[568184]
NPT27	Others	Unspecified		IC50	=	1.13	ug.mL-1	PMID[568184]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3500.0	nM	PMID[568185]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5200.0	nM	PMID[568185]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.74	g	PMID[568185]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.03	g	PMID[568185]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.85	g	PMID[568185]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	7.9	%	PMID[568185]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	7.6	%	PMID[568185]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	6.6	%	PMID[568185]

☑ 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 NPC100257 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	286
0.1-0.2	2109
0.2-0.3	6728
0.3-0.4	13753
0.4-0.5	7196
0.5-0.6	7021
0.6-0.7	4775
0.7-0.8	775
0.8-0.85	47
0.85-0.9	3
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC224410
0.9231	High Similarity	NPC197158
0.9231	High Similarity	NPC471624
0.8681	High Similarity	NPC471043
0.8523	High Similarity	NPC476458
0.8523	High Similarity	NPC258153
0.8495	Intermediate Similarity	NPC470230
0.8462	Intermediate Similarity	NPC175293
0.8316	Intermediate Similarity	NPC475118
0.8316	Intermediate Similarity	NPC47853
0.8229	Intermediate Similarity	NPC470229
0.8229	Intermediate Similarity	NPC470232
0.8191	Intermediate Similarity	NPC475776
0.8163	Intermediate Similarity	NPC471038
0.8163	Intermediate Similarity	NPC16911
0.8163	Intermediate Similarity	NPC469986
0.8163	Intermediate Similarity	NPC78427
0.8144	Intermediate Similarity	NPC329910
0.8125	Intermediate Similarity	NPC470386
0.8125	Intermediate Similarity	NPC470385
0.8081	Intermediate Similarity	NPC267921
0.8081	Intermediate Similarity	NPC287676
0.8081	Intermediate Similarity	NPC108371
0.8061	Intermediate Similarity	NPC253586
0.8061	Intermediate Similarity	NPC96839
0.8041	Intermediate Similarity	NPC280877
0.8039	Intermediate Similarity	NPC295366
0.8021	Intermediate Similarity	NPC475700
0.8021	Intermediate Similarity	NPC199543
0.802	Intermediate Similarity	NPC221421
0.8	Intermediate Similarity	NPC289148
0.8	Intermediate Similarity	NPC163963
0.8	Intermediate Similarity	NPC46848
0.8	Intermediate Similarity	NPC52899
0.7959	Intermediate Similarity	NPC473964
0.7959	Intermediate Similarity	NPC200054
0.7959	Intermediate Similarity	NPC29410
0.7959	Intermediate Similarity	NPC470387
0.7957	Intermediate Similarity	NPC471042
0.7925	Intermediate Similarity	NPC476964
0.7921	Intermediate Similarity	NPC304832
0.7921	Intermediate Similarity	NPC214946
0.7921	Intermediate Similarity	NPC88203
0.7921	Intermediate Similarity	NPC76866
0.7921	Intermediate Similarity	NPC148628
0.7921	Intermediate Similarity	NPC246736
0.7921	Intermediate Similarity	NPC275990
0.7921	Intermediate Similarity	NPC286519
0.7921	Intermediate Similarity	NPC170615
0.7917	Intermediate Similarity	NPC250753
0.7917	Intermediate Similarity	NPC476934
0.7917	Intermediate Similarity	NPC198242
0.7917	Intermediate Similarity	NPC211403
0.7912	Intermediate Similarity	NPC226988
0.79	Intermediate Similarity	NPC470388
0.7895	Intermediate Similarity	NPC116620
0.7879	Intermediate Similarity	NPC474921
0.7879	Intermediate Similarity	NPC473963
0.7879	Intermediate Similarity	NPC469810
0.7857	Intermediate Similarity	NPC98639
0.7857	Intermediate Similarity	NPC217329
0.7857	Intermediate Similarity	NPC259042
0.7857	Intermediate Similarity	NPC157686
0.7857	Intermediate Similarity	NPC210214
0.7843	Intermediate Similarity	NPC87927
0.7843	Intermediate Similarity	NPC139347
0.7843	Intermediate Similarity	NPC216114
0.7843	Intermediate Similarity	NPC277074
0.7843	Intermediate Similarity	NPC122811
0.7843	Intermediate Similarity	NPC99510
0.7843	Intermediate Similarity	NPC209298
0.7826	Intermediate Similarity	NPC170862
0.7822	Intermediate Similarity	NPC39683
0.78	Intermediate Similarity	NPC98837
0.78	Intermediate Similarity	NPC162459
0.78	Intermediate Similarity	NPC89099
0.78	Intermediate Similarity	NPC252295
0.78	Intermediate Similarity	NPC28864
0.78	Intermediate Similarity	NPC20479
0.78	Intermediate Similarity	NPC38471
0.78	Intermediate Similarity	NPC38296
0.78	Intermediate Similarity	NPC474793
0.7788	Intermediate Similarity	NPC88833
0.7788	Intermediate Similarity	NPC470952
0.7788	Intermediate Similarity	NPC96333
0.7778	Intermediate Similarity	NPC307164
0.7778	Intermediate Similarity	NPC471475
0.7778	Intermediate Similarity	NPC118987
0.7778	Intermediate Similarity	NPC93245
0.7778	Intermediate Similarity	NPC13949
0.7767	Intermediate Similarity	NPC84928
0.7767	Intermediate Similarity	NPC244247
0.7767	Intermediate Similarity	NPC13149
0.7767	Intermediate Similarity	NPC98603
0.7757	Intermediate Similarity	NPC40608
0.7755	Intermediate Similarity	NPC225474
0.7755	Intermediate Similarity	NPC471446
0.7755	Intermediate Similarity	NPC473434
0.7755	Intermediate Similarity	NPC41649
0.7755	Intermediate Similarity	NPC148000
0.7755	Intermediate Similarity	NPC474841
0.7755	Intermediate Similarity	NPC469596
0.7742	Intermediate Similarity	NPC219011
0.7742	Intermediate Similarity	NPC470011
0.7736	Intermediate Similarity	NPC124053
0.7736	Intermediate Similarity	NPC179642
0.7723	Intermediate Similarity	NPC293866
0.7717	Intermediate Similarity	NPC476935
0.7708	Intermediate Similarity	NPC288699
0.7708	Intermediate Similarity	NPC11611
0.77	Intermediate Similarity	NPC10864
0.7692	Intermediate Similarity	NPC28791
0.7692	Intermediate Similarity	NPC164600
0.7692	Intermediate Similarity	NPC170038
0.7692	Intermediate Similarity	NPC138908
0.7692	Intermediate Similarity	NPC37600
0.7692	Intermediate Similarity	NPC103172
0.7692	Intermediate Similarity	NPC200957
0.7684	Intermediate Similarity	NPC476932
0.7684	Intermediate Similarity	NPC259009
0.7677	Intermediate Similarity	NPC90014
0.7677	Intermediate Similarity	NPC56369
0.767	Intermediate Similarity	NPC96217
0.767	Intermediate Similarity	NPC469985
0.767	Intermediate Similarity	NPC36688
0.767	Intermediate Similarity	NPC72842
0.767	Intermediate Similarity	NPC254202
0.7664	Intermediate Similarity	NPC471251
0.7664	Intermediate Similarity	NPC470311
0.7664	Intermediate Similarity	NPC94650
0.766	Intermediate Similarity	NPC471034
0.766	Intermediate Similarity	NPC190704
0.7658	Intermediate Similarity	NPC475520
0.7653	Intermediate Similarity	NPC294263
0.7647	Intermediate Similarity	NPC148279
0.7647	Intermediate Similarity	NPC121218
0.7647	Intermediate Similarity	NPC471790
0.7647	Intermediate Similarity	NPC253886
0.7647	Intermediate Similarity	NPC295276
0.7647	Intermediate Similarity	NPC252614
0.7647	Intermediate Similarity	NPC236585
0.7642	Intermediate Similarity	NPC471250
0.7634	Intermediate Similarity	NPC194637
0.7629	Intermediate Similarity	NPC149761
0.7629	Intermediate Similarity	NPC8062
0.7629	Intermediate Similarity	NPC470378
0.7629	Intermediate Similarity	NPC261994
0.7629	Intermediate Similarity	NPC161638
0.7629	Intermediate Similarity	NPC80401
0.7624	Intermediate Similarity	NPC26270
0.7624	Intermediate Similarity	NPC473155
0.7619	Intermediate Similarity	NPC61071
0.7619	Intermediate Similarity	NPC251824
0.7619	Intermediate Similarity	NPC86852
0.7619	Intermediate Similarity	NPC166993
0.7619	Intermediate Similarity	NPC186054
0.7619	Intermediate Similarity	NPC201908
0.7619	Intermediate Similarity	NPC176949
0.7604	Intermediate Similarity	NPC50847
0.76	Intermediate Similarity	NPC118159
0.7596	Intermediate Similarity	NPC474558
0.7596	Intermediate Similarity	NPC202793
0.7596	Intermediate Similarity	NPC101842
0.7596	Intermediate Similarity	NPC283850
0.7582	Intermediate Similarity	NPC263951
0.7579	Intermediate Similarity	NPC9231
0.7579	Intermediate Similarity	NPC472505
0.7576	Intermediate Similarity	NPC84893
0.7576	Intermediate Similarity	NPC24861
0.7573	Intermediate Similarity	NPC475803
0.7573	Intermediate Similarity	NPC124544
0.7573	Intermediate Similarity	NPC164551
0.7573	Intermediate Similarity	NPC309388
0.757	Intermediate Similarity	NPC98069
0.757	Intermediate Similarity	NPC49730
0.7568	Intermediate Similarity	NPC473720
0.7551	Intermediate Similarity	NPC476168
0.7551	Intermediate Similarity	NPC299185
0.7551	Intermediate Similarity	NPC198054
0.7549	Intermediate Similarity	NPC47024
0.7549	Intermediate Similarity	NPC470906
0.7549	Intermediate Similarity	NPC476303
0.7549	Intermediate Similarity	NPC477656
0.7547	Intermediate Similarity	NPC231278
0.7547	Intermediate Similarity	NPC112895
0.7547	Intermediate Similarity	NPC273155
0.7547	Intermediate Similarity	NPC63841
0.7547	Intermediate Similarity	NPC218123
0.7547	Intermediate Similarity	NPC255082
0.7547	Intermediate Similarity	NPC211224
0.7545	Intermediate Similarity	NPC469794
0.7545	Intermediate Similarity	NPC72772
0.7527	Intermediate Similarity	NPC13494
0.7526	Intermediate Similarity	NPC285982
0.7525	Intermediate Similarity	NPC2049
0.7525	Intermediate Similarity	NPC136781
0.7524	Intermediate Similarity	NPC56656
0.7524	Intermediate Similarity	NPC285927
0.7524	Intermediate Similarity	NPC472655
0.75	Intermediate Similarity	NPC42673

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 NPC100257 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	267
0.1-0.2	2393
0.2-0.3	4086
0.3-0.4	1627
0.4-0.5	402
0.5-0.6	177
0.6-0.7	186
0.7-0.8	12
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
0.7692	Intermediate Similarity	NPD6008	Approved
0.7677	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7638	Approved
0.74	Intermediate Similarity	NPD6001	Approved
0.7379	Intermediate Similarity	NPD7640	Approved
0.7379	Intermediate Similarity	NPD7639	Approved
0.7374	Intermediate Similarity	NPD5693	Phase 1
0.72	Intermediate Similarity	NPD8034	Phase 2
0.72	Intermediate Similarity	NPD8035	Phase 2
0.7113	Intermediate Similarity	NPD1694	Approved
0.71	Intermediate Similarity	NPD5207	Approved
0.7075	Intermediate Similarity	NPD7632	Discontinued
0.7064	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7115	Discovery
0.7	Intermediate Similarity	NPD6673	Approved
0.7	Intermediate Similarity	NPD6904	Approved
0.7	Intermediate Similarity	NPD6080	Approved
0.6979	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3573	Approved
0.6939	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4788	Approved
0.6903	Remote Similarity	NPD8133	Approved
0.69	Remote Similarity	NPD5737	Approved
0.69	Remote Similarity	NPD6903	Approved
0.69	Remote Similarity	NPD6672	Approved
0.69	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5208	Approved
0.6893	Remote Similarity	NPD7900	Approved
0.6893	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7492	Approved
0.6869	Remote Similarity	NPD7146	Approved
0.6869	Remote Similarity	NPD5330	Approved
0.6869	Remote Similarity	NPD6098	Approved
0.6869	Remote Similarity	NPD7521	Approved
0.6869	Remote Similarity	NPD6684	Approved
0.6869	Remote Similarity	NPD6409	Approved
0.6869	Remote Similarity	NPD7334	Approved
0.686	Remote Similarity	NPD7736	Approved
0.6838	Remote Similarity	NPD6054	Approved
0.6838	Remote Similarity	NPD6319	Approved
0.6833	Remote Similarity	NPD6616	Approved
0.6818	Remote Similarity	NPD5697	Approved
0.6803	Remote Similarity	NPD7319	Approved
0.6796	Remote Similarity	NPD6399	Phase 3
0.6792	Remote Similarity	NPD5696	Approved
0.6792	Remote Similarity	NPD4225	Approved
0.6786	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6016	Approved
0.678	Remote Similarity	NPD6015	Approved
0.6777	Remote Similarity	NPD7078	Approved
0.6765	Remote Similarity	NPD5692	Phase 3
0.6757	Remote Similarity	NPD7320	Approved
0.6757	Remote Similarity	NPD6881	Approved
0.6757	Remote Similarity	NPD6899	Approved
0.6757	Remote Similarity	NPD6011	Approved
0.6754	Remote Similarity	NPD4632	Approved
0.6737	Remote Similarity	NPD6114	Approved
0.6737	Remote Similarity	NPD6115	Approved
0.6737	Remote Similarity	NPD6697	Approved
0.6737	Remote Similarity	NPD6118	Approved
0.6731	Remote Similarity	NPD7748	Approved
0.6727	Remote Similarity	NPD6675	Approved
0.6727	Remote Similarity	NPD6402	Approved
0.6727	Remote Similarity	NPD7128	Approved
0.6727	Remote Similarity	NPD5739	Approved
0.6726	Remote Similarity	NPD6649	Approved
0.6726	Remote Similarity	NPD6650	Approved
0.6723	Remote Similarity	NPD6370	Approved
0.6723	Remote Similarity	NPD5988	Approved
0.6699	Remote Similarity	NPD6050	Approved
0.6699	Remote Similarity	NPD5694	Approved
0.6698	Remote Similarity	NPD6084	Phase 2
0.6698	Remote Similarity	NPD7902	Approved
0.6698	Remote Similarity	NPD6083	Phase 2
0.6697	Remote Similarity	NPD6052	Approved
0.6696	Remote Similarity	NPD6372	Approved
0.6696	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6014	Approved
0.6696	Remote Similarity	NPD6373	Approved
0.6696	Remote Similarity	NPD6013	Approved
0.6696	Remote Similarity	NPD6012	Approved
0.6695	Remote Similarity	NPD6059	Approved
0.6694	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD5701	Approved
0.6639	Remote Similarity	NPD8293	Discontinued
0.6637	Remote Similarity	NPD7102	Approved
0.6637	Remote Similarity	NPD7290	Approved
0.6637	Remote Similarity	NPD6883	Approved
0.663	Remote Similarity	NPD5777	Approved
0.6581	Remote Similarity	NPD6009	Approved
0.6579	Remote Similarity	NPD8130	Phase 1
0.6579	Remote Similarity	NPD6847	Approved
0.6579	Remote Similarity	NPD6869	Approved
0.6579	Remote Similarity	NPD6617	Approved
0.6538	Remote Similarity	NPD5281	Approved
0.6538	Remote Similarity	NPD7515	Phase 2
0.6538	Remote Similarity	NPD5284	Approved
0.6535	Remote Similarity	NPD3618	Phase 1
0.6526	Remote Similarity	NPD6117	Approved
0.6522	Remote Similarity	NPD6882	Approved
0.6522	Remote Similarity	NPD8297	Approved
0.6509	Remote Similarity	NPD5654	Approved
0.6505	Remote Similarity	NPD1695	Approved
0.6505	Remote Similarity	NPD6051	Approved
0.65	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5983	Phase 2
0.6491	Remote Similarity	NPD4634	Approved
0.6476	Remote Similarity	NPD4202	Approved
0.6465	Remote Similarity	NPD4223	Phase 3
0.6465	Remote Similarity	NPD4221	Approved
0.6458	Remote Similarity	NPD6116	Phase 1
0.6455	Remote Similarity	NPD5211	Phase 2
0.6444	Remote Similarity	NPD4224	Phase 2
0.6435	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5286	Approved
0.6422	Remote Similarity	NPD5285	Approved
0.6422	Remote Similarity	NPD4696	Approved
0.6421	Remote Similarity	NPD3702	Approved
0.6393	Remote Similarity	NPD7604	Phase 2
0.6389	Remote Similarity	NPD4755	Approved
0.6389	Remote Similarity	NPD5959	Approved
0.6387	Remote Similarity	NPD7328	Approved
0.6387	Remote Similarity	NPD7327	Approved
0.6381	Remote Similarity	NPD6079	Approved
0.6372	Remote Similarity	NPD6614	Approved
0.6364	Remote Similarity	NPD6921	Approved
0.6364	Remote Similarity	NPD5223	Approved
0.6356	Remote Similarity	NPD6274	Approved
0.6355	Remote Similarity	NPD5210	Approved
0.6355	Remote Similarity	NPD4629	Approved
0.6346	Remote Similarity	NPD5328	Approved
0.6346	Remote Similarity	NPD4753	Phase 2
0.6339	Remote Similarity	NPD5141	Approved
0.6337	Remote Similarity	NPD4197	Approved
0.6333	Remote Similarity	NPD7516	Approved
0.632	Remote Similarity	NPD6033	Approved
0.6316	Remote Similarity	NPD6686	Approved
0.6316	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5225	Approved
0.6306	Remote Similarity	NPD4633	Approved
0.6306	Remote Similarity	NPD5226	Approved
0.6306	Remote Similarity	NPD5224	Approved
0.6304	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5360	Phase 3
0.6303	Remote Similarity	NPD6317	Approved
0.6296	Remote Similarity	NPD4697	Phase 3
0.6296	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5222	Approved
0.6296	Remote Similarity	NPD5221	Approved
0.629	Remote Similarity	NPD6336	Discontinued
0.6281	Remote Similarity	NPD8377	Approved
0.6281	Remote Similarity	NPD8294	Approved
0.6277	Remote Similarity	NPD6081	Approved
0.6275	Remote Similarity	NPD5329	Approved
0.6273	Remote Similarity	NPD4700	Approved
0.625	Remote Similarity	NPD5174	Approved
0.625	Remote Similarity	NPD6335	Approved
0.625	Remote Similarity	NPD6313	Approved
0.625	Remote Similarity	NPD3703	Phase 2
0.625	Remote Similarity	NPD6314	Approved
0.625	Remote Similarity	NPD5175	Approved
0.6239	Remote Similarity	NPD5173	Approved
0.6239	Remote Similarity	NPD6053	Discontinued
0.623	Remote Similarity	NPD8380	Approved
0.623	Remote Similarity	NPD8033	Approved
0.623	Remote Similarity	NPD8378	Approved
0.623	Remote Similarity	NPD8296	Approved
0.623	Remote Similarity	NPD8335	Approved
0.623	Remote Similarity	NPD8379	Approved
0.6216	Remote Similarity	NPD1700	Approved
0.6214	Remote Similarity	NPD4688	Approved
0.6214	Remote Similarity	NPD4689	Approved
0.6214	Remote Similarity	NPD5205	Approved
0.6214	Remote Similarity	NPD5690	Phase 2
0.6214	Remote Similarity	NPD4693	Phase 3
0.6214	Remote Similarity	NPD4138	Approved
0.6214	Remote Similarity	NPD4690	Approved
0.6207	Remote Similarity	NPD6371	Approved
0.6204	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7100	Approved
0.6198	Remote Similarity	NPD7101	Approved
0.6176	Remote Similarity	NPD4786	Approved
0.6176	Remote Similarity	NPD3133	Approved
0.6176	Remote Similarity	NPD3668	Phase 3
0.6176	Remote Similarity	NPD3665	Phase 1
0.6176	Remote Similarity	NPD3666	Approved
0.6147	Remote Similarity	NPD7732	Phase 3
0.6139	Remote Similarity	NPD3667	Approved
0.6132	Remote Similarity	NPD5785	Approved
0.6129	Remote Similarity	NPD8328	Phase 3
0.6121	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5282	Discontinued
0.6106	Remote Similarity	NPD4754	Approved
0.6105	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4758	Discontinued
0.6087	Remote Similarity	NPD6412	Phase 2

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