NPASS Compound

Structure

CID288084 OpenBabel06191716092D 30 33 0 0 1 0 0 0 0 0999 V2000 3.5116 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 -0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 4.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9135 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9135 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6456 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2514 -1.4476 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 5.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8185 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5759 -2.5227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5522 -2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 2.5933 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 1.7796 0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 8 2 0 0 0 0 2 4 2 0 0 0 0 2 8 1 0 0 0 0 3 9 2 0 0 0 0 4 9 1 0 0 0 0 5 10 2 0 0 0 0 5 11 1 0 0 0 0 6 10 1 0 0 0 0 6 12 2 0 0 0 0 7 21 1 0 0 0 0 8 18 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 14 2 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 28 1 0 0 0 0 13 7 1 6 0 0 0 13 15 1 0 0 0 0 13 29 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 25 1 1 0 0 0 16 19 1 0 0 0 0 16 26 2 0 0 0 0 17 20 1 0 0 0 0 17 27 1 6 0 0 0 18 19 2 0 0 0 0 18 28 1 0 0 0 0 19 30 1 0 0 0 0 20 29 1 0 0 0 0 20 30 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.09
Volume:	387.061
LogP:	1.321
LogD:	0.909
LogS:	-4.299
# Rotatable Bonds:	4
TPSA:	170.05
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.348
Synthetic Accessibility Score:	3.708
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.835
MDCK Permeability:	9.744348972162697e-06
Pgp-inhibitor:	0.025
Pgp-substrate:	0.623
Human Intestinal Absorption (HIA):	0.264
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	91.32378387451172%
Volume Distribution (VD):	0.988
Pgp-substrate:	10.70513916015625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.386
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.115
CYP2C9-substrate:	0.792
CYP2D6-inhibitor:	0.495
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.309
CYP3A4-substrate:	0.021

ADMET: Excretion

Clearance (CL):	4.893
Half-life (T1/2):	0.841

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.139
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.802
Rat Oral Acute Toxicity:	0.183
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.874
Carcinogencity:	0.073
Eye Corrosion:	0.003
Eye Irritation:	0.419
Respiratory Toxicity:	0.034

Download Data

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

Natural Product: NPC288084

Natural Product ID:	NPC288084
*Common Name:**	Juglanin
IUPAC Name:	3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms:	Juglanin
Standard InCHIKey:	POQICXMTUPVZMX-UXYNSRGZSA-N
Standard InCHI:	InChI=1S/C20H18O10/c21-7-13-15(25)17(27)20(29-13)30-19-16(26)14-11(24)5-10(23)6-12(14)28-18(19)8-1-3-9(22)4-2-8/h1-6,13,15,17,20-25,27H,7H2/t13-,15-,17+,20-/m0/s1
SMILES:	c1cc(ccc1c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1[C@@H]([C@H]([C@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469440
PubChem CID:	5318717
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

*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
NPO3057	Polygonum aviculare	Species	Polygonaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1016/S1572-557X(05)02007-6]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21190854]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	stems and twigs	Beihai, Guangxi province, China	2008-Jan	PMID[22196120]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	twig	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	bark	n.a.	PMID[7623051]
NPO3057	Polygonum aviculare	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO1982	Tilia miqueliana	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21919	Polysaccharidum versicolor	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO3057	Polygonum aviculare	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3057	Polygonum aviculare	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1982	Tilia miqueliana	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21919	Polysaccharidum versicolor	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3057	Polygonum aviculare	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3057	Polygonum aviculare	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15245	Paenibacillus macerans	Species	Paenibacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2675	Cordyline neocaledonica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8343	Centaurea corcubionensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1189	Aspergillus giganteus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10919	Salvia cyanescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10444	Dendrophthoe falcata	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1982	Tilia miqueliana	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12044	Dorstenia barteri	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	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	4
Others	1

Activity Type	# Activity
Cell Line	2
Individual Protein	1
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	0.0	%	PMID[503216]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	1800.0	nM	PMID[503217]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	2400.0	nM	PMID[503217]
NPT2	Others	Unspecified		IC50	=	2000.0	nM	PMID[503217]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[503217]

☑ 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 NPC288084 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	421
0.1-0.2	1722
0.2-0.3	4020
0.3-0.4	9434
0.4-0.5	9187
0.5-0.6	4329
0.6-0.7	5840
0.7-0.8	4909
0.8-0.85	1913
0.85-0.9	775
0.9-0.95	142
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9739	High Similarity	NPC150164
0.9735	High Similarity	NPC77672
0.9735	High Similarity	NPC54802
0.9735	High Similarity	NPC133671
0.9735	High Similarity	NPC78263
0.9735	High Similarity	NPC135391
0.9735	High Similarity	NPC197304
0.9671	High Similarity	NPC320283
0.9671	High Similarity	NPC41121
0.9671	High Similarity	NPC472459
0.9671	High Similarity	NPC111929
0.9669	High Similarity	NPC203500
0.9669	High Similarity	NPC307938
0.9669	High Similarity	NPC323593
0.9613	High Similarity	NPC72016
0.9608	High Similarity	NPC470405
0.9608	High Similarity	NPC471079
0.9608	High Similarity	NPC304741
0.9605	High Similarity	NPC182634
0.9605	High Similarity	NPC108831
0.9605	High Similarity	NPC122809
0.9551	High Similarity	NPC255615
0.9551	High Similarity	NPC67037
0.9545	High Similarity	NPC476215
0.9545	High Similarity	NPC249281
0.9545	High Similarity	NPC246943
0.9545	High Similarity	NPC259957
0.9545	High Similarity	NPC173582
0.9545	High Similarity	NPC253788
0.9545	High Similarity	NPC159579
0.9545	High Similarity	NPC139320
0.9545	High Similarity	NPC181465
0.9545	High Similarity	NPC135846
0.9545	High Similarity	NPC470125
0.9545	High Similarity	NPC297987
0.9545	High Similarity	NPC129217
0.9545	High Similarity	NPC48093
0.9545	High Similarity	NPC116458
0.9545	High Similarity	NPC282169
0.9545	High Similarity	NPC276377
0.9545	High Similarity	NPC163242
0.9545	High Similarity	NPC85707
0.9545	High Similarity	NPC215710
0.9545	High Similarity	NPC473438
0.9545	High Similarity	NPC224530
0.9545	High Similarity	NPC170052
0.9545	High Similarity	NPC265885
0.9545	High Similarity	NPC216496
0.9545	High Similarity	NPC64305
0.9539	High Similarity	NPC149368
0.9539	High Similarity	NPC265480
0.9536	High Similarity	NPC210003
0.9536	High Similarity	NPC39360
0.9536	High Similarity	NPC83283
0.9536	High Similarity	NPC29763
0.9536	High Similarity	NPC143851
0.9487	High Similarity	NPC34531
0.9484	High Similarity	NPC240306
0.9484	High Similarity	NPC27942
0.9481	High Similarity	NPC187379
0.9481	High Similarity	NPC136761
0.9481	High Similarity	NPC153342
0.9477	High Similarity	NPC6985
0.9474	High Similarity	NPC27408
0.9474	High Similarity	NPC95090
0.947	High Similarity	NPC259182
0.947	High Similarity	NPC88484
0.947	High Similarity	NPC121001
0.947	High Similarity	NPC259767
0.9427	High Similarity	NPC254306
0.9423	High Similarity	NPC278419
0.9423	High Similarity	NPC179198
0.9423	High Similarity	NPC66087
0.9423	High Similarity	NPC121703
0.9416	High Similarity	NPC104677
0.9408	High Similarity	NPC106625
0.9367	High Similarity	NPC149244
0.9367	High Similarity	NPC48640
0.9363	High Similarity	NPC19240
0.9363	High Similarity	NPC289667
0.9363	High Similarity	NPC85751
0.9363	High Similarity	NPC292929
0.9363	High Similarity	NPC205824
0.9363	High Similarity	NPC76831
0.9363	High Similarity	NPC129264
0.9359	High Similarity	NPC131745
0.9355	High Similarity	NPC306978
0.9355	High Similarity	NPC200708
0.9351	High Similarity	NPC161749
0.9351	High Similarity	NPC65003
0.9351	High Similarity	NPC473512
0.9351	High Similarity	NPC60966
0.9351	High Similarity	NPC197896
0.9351	High Similarity	NPC44931
0.9351	High Similarity	NPC313163
0.9351	High Similarity	NPC156457
0.9351	High Similarity	NPC258035
0.9351	High Similarity	NPC129827
0.9346	High Similarity	NPC39351
0.9346	High Similarity	NPC72649
0.9346	High Similarity	NPC97052
0.9346	High Similarity	NPC99233
0.9346	High Similarity	NPC26195
0.9346	High Similarity	NPC169248
0.9338	High Similarity	NPC191154
0.9313	High Similarity	NPC245452
0.9308	High Similarity	NPC476771
0.9304	High Similarity	NPC118284
0.9304	High Similarity	NPC256188
0.9304	High Similarity	NPC11432
0.9304	High Similarity	NPC64425
0.9304	High Similarity	NPC274618
0.9304	High Similarity	NPC56077
0.9304	High Similarity	NPC12013
0.9304	High Similarity	NPC179950
0.9304	High Similarity	NPC281131
0.9304	High Similarity	NPC476470
0.9304	High Similarity	NPC32641
0.9304	High Similarity	NPC189564
0.9304	High Similarity	NPC221342
0.9304	High Similarity	NPC142142
0.9304	High Similarity	NPC88789
0.9304	High Similarity	NPC477613
0.9304	High Similarity	NPC145038
0.9304	High Similarity	NPC203145
0.9304	High Similarity	NPC186816
0.9304	High Similarity	NPC276222
0.9304	High Similarity	NPC253662
0.9304	High Similarity	NPC308404
0.9299	High Similarity	NPC80068
0.9299	High Similarity	NPC183672
0.929	High Similarity	NPC473634
0.929	High Similarity	NPC73511
0.929	High Similarity	NPC22062
0.929	High Similarity	NPC138811
0.9286	High Similarity	NPC261866
0.9286	High Similarity	NPC206378
0.9286	High Similarity	NPC127406
0.9286	High Similarity	NPC170475
0.9276	High Similarity	NPC134819
0.925	High Similarity	NPC72249
0.9245	High Similarity	NPC84362
0.9245	High Similarity	NPC223424
0.9245	High Similarity	NPC317489
0.9245	High Similarity	NPC173637
0.9245	High Similarity	NPC127546
0.9245	High Similarity	NPC52550
0.9241	High Similarity	NPC139060
0.9241	High Similarity	NPC19388
0.9241	High Similarity	NPC55786
0.9241	High Similarity	NPC240431
0.9241	High Similarity	NPC277205
0.9241	High Similarity	NPC287889
0.9241	High Similarity	NPC135358
0.9236	High Similarity	NPC259834
0.9231	High Similarity	NPC473623
0.9226	High Similarity	NPC43638
0.9226	High Similarity	NPC470606
0.9226	High Similarity	NPC23817
0.9205	High Similarity	NPC199335
0.9205	High Similarity	NPC287294
0.9193	High Similarity	NPC476772
0.9187	High Similarity	NPC120099
0.9187	High Similarity	NPC223747
0.9187	High Similarity	NPC5319
0.9187	High Similarity	NPC219904
0.9187	High Similarity	NPC225434
0.9187	High Similarity	NPC203050
0.9182	High Similarity	NPC113968
0.9182	High Similarity	NPC135599
0.9182	High Similarity	NPC277174
0.9182	High Similarity	NPC73855
0.9182	High Similarity	NPC328940
0.9182	High Similarity	NPC21100
0.9182	High Similarity	NPC197285
0.9172	High Similarity	NPC477629
0.9172	High Similarity	NPC210961
0.9172	High Similarity	NPC195685
0.9172	High Similarity	NPC47923
0.9172	High Similarity	NPC270675
0.9172	High Similarity	NPC477628
0.9172	High Similarity	NPC472994
0.9172	High Similarity	NPC303913
0.9172	High Similarity	NPC101636
0.9167	High Similarity	NPC308265
0.9167	High Similarity	NPC470607
0.9161	High Similarity	NPC473657
0.9161	High Similarity	NPC45165
0.9161	High Similarity	NPC295613
0.9156	High Similarity	NPC268950
0.9156	High Similarity	NPC108706
0.9156	High Similarity	NPC211158
0.9156	High Similarity	NPC78021
0.9156	High Similarity	NPC87304
0.915	High Similarity	NPC23253
0.9141	High Similarity	NPC296018
0.9141	High Similarity	NPC154741
0.9139	High Similarity	NPC23084
0.913	High Similarity	NPC96605
0.913	High Similarity	NPC95866

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 NPC288084 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	867
0.2-0.3	1876
0.3-0.4	2730
0.4-0.5	1921
0.5-0.6	955
0.6-0.7	278
0.7-0.8	113
0.8-0.85	23
0.85-0.9	14
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9351	High Similarity	NPD4381	Clinical (unspecified phase)
0.9187	High Similarity	NPD7804	Clinical (unspecified phase)
0.9125	High Similarity	NPD3818	Discontinued
0.9074	High Similarity	NPD6797	Phase 2
0.9018	High Similarity	NPD7251	Discontinued
0.8963	High Similarity	NPD7808	Phase 3
0.8963	High Similarity	NPD4338	Clinical (unspecified phase)
0.8846	High Similarity	NPD6801	Discontinued
0.8834	High Similarity	NPD7054	Approved
0.878	High Similarity	NPD7472	Approved
0.8766	High Similarity	NPD5403	Approved
0.8742	High Similarity	NPD7075	Discontinued
0.8718	High Similarity	NPD4380	Phase 2
0.8693	High Similarity	NPD6799	Approved
0.8667	High Similarity	NPD7074	Phase 3
0.8636	High Similarity	NPD4378	Clinical (unspecified phase)
0.8636	High Similarity	NPD5401	Approved
0.8616	High Similarity	NPD3817	Phase 2
0.8563	High Similarity	NPD6559	Discontinued
0.8562	High Similarity	NPD3882	Suspended
0.8553	High Similarity	NPD7096	Clinical (unspecified phase)
0.8543	High Similarity	NPD1552	Clinical (unspecified phase)
0.8543	High Similarity	NPD1550	Clinical (unspecified phase)
0.85	High Similarity	NPD5402	Approved
0.8487	Intermediate Similarity	NPD1549	Phase 2
0.8462	Intermediate Similarity	NPD1512	Approved
0.8424	Intermediate Similarity	NPD6166	Phase 2
0.8424	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD1934	Approved
0.8365	Intermediate Similarity	NPD6599	Discontinued
0.8333	Intermediate Similarity	NPD1511	Approved
0.8323	Intermediate Similarity	NPD2801	Approved
0.8323	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1510	Phase 2
0.8235	Intermediate Similarity	NPD2796	Approved
0.8165	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD7411	Suspended
0.8049	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1240	Approved
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1607	Approved
0.7921	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3751	Discontinued
0.7879	Intermediate Similarity	NPD7819	Suspended
0.787	Intermediate Similarity	NPD3787	Discontinued
0.7861	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD3750	Approved
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1551	Phase 2
0.7751	Intermediate Similarity	NPD5494	Approved
0.7747	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD3749	Approved
0.773	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7199	Phase 2
0.7706	Intermediate Similarity	NPD6959	Discontinued
0.7692	Intermediate Similarity	NPD919	Approved
0.7688	Intermediate Similarity	NPD4628	Phase 3
0.7683	Intermediate Similarity	NPD1653	Approved
0.7674	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7584	Approved
0.7627	Intermediate Similarity	NPD8312	Approved
0.7627	Intermediate Similarity	NPD8313	Approved
0.7625	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2800	Approved
0.7622	Intermediate Similarity	NPD920	Approved
0.7607	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD1247	Approved
0.7595	Intermediate Similarity	NPD7033	Discontinued
0.7593	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7768	Phase 2
0.7571	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD8455	Phase 2
0.7558	Intermediate Similarity	NPD6232	Discontinued
0.7548	Intermediate Similarity	NPD6798	Discontinued
0.7533	Intermediate Similarity	NPD1091	Approved
0.7529	Intermediate Similarity	NPD7473	Discontinued
0.7527	Intermediate Similarity	NPD6781	Approved
0.7527	Intermediate Similarity	NPD6778	Approved
0.7527	Intermediate Similarity	NPD6782	Approved
0.7527	Intermediate Similarity	NPD6776	Approved
0.7527	Intermediate Similarity	NPD6777	Approved
0.7527	Intermediate Similarity	NPD6779	Approved
0.7527	Intermediate Similarity	NPD6780	Approved
0.7516	Intermediate Similarity	NPD1243	Approved
0.7514	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD6233	Phase 2
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD6234	Discontinued
0.7484	Intermediate Similarity	NPD3748	Approved
0.7471	Intermediate Similarity	NPD4965	Approved
0.7471	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4967	Phase 2
0.7471	Intermediate Similarity	NPD4966	Approved
0.7451	Intermediate Similarity	NPD1203	Approved
0.7443	Intermediate Similarity	NPD5844	Phase 1
0.7439	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6190	Approved
0.7419	Intermediate Similarity	NPD6832	Phase 2
0.7416	Intermediate Similarity	NPD7685	Pre-registration
0.7405	Intermediate Similarity	NPD1933	Approved
0.7405	Intermediate Similarity	NPD6355	Discontinued
0.7403	Intermediate Similarity	NPD8434	Phase 2
0.7391	Intermediate Similarity	NPD2344	Approved
0.7386	Intermediate Similarity	NPD7228	Approved
0.7383	Intermediate Similarity	NPD1548	Phase 1
0.736	Intermediate Similarity	NPD5953	Discontinued
0.7358	Intermediate Similarity	NPD6651	Approved
0.7353	Intermediate Similarity	NPD1465	Phase 2
0.7348	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7286	Phase 2
0.7342	Intermediate Similarity	NPD1613	Approved
0.7342	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2935	Discontinued
0.7325	Intermediate Similarity	NPD2313	Discontinued
0.7316	Intermediate Similarity	NPD7698	Approved
0.7316	Intermediate Similarity	NPD7696	Phase 3
0.7316	Intermediate Similarity	NPD7697	Approved
0.7303	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1652	Phase 2
0.729	Intermediate Similarity	NPD2798	Approved
0.7277	Intermediate Similarity	NPD7871	Phase 2
0.7277	Intermediate Similarity	NPD7870	Phase 2
0.7268	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7874	Approved
0.7258	Intermediate Similarity	NPD6535	Approved
0.7258	Intermediate Similarity	NPD6534	Approved
0.7254	Intermediate Similarity	NPD7701	Phase 2
0.7254	Intermediate Similarity	NPD7585	Approved
0.7233	Intermediate Similarity	NPD943	Approved
0.7219	Intermediate Similarity	NPD7458	Discontinued
0.7216	Intermediate Similarity	NPD8151	Discontinued
0.7215	Intermediate Similarity	NPD3268	Approved
0.7212	Intermediate Similarity	NPD2309	Approved
0.7202	Intermediate Similarity	NPD7583	Approved
0.7195	Intermediate Similarity	NPD2654	Approved
0.719	Intermediate Similarity	NPD422	Phase 1
0.7188	Intermediate Similarity	NPD4340	Discontinued
0.7186	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD2403	Approved
0.717	Intermediate Similarity	NPD4062	Phase 3
0.7166	Intermediate Similarity	NPD4360	Phase 2
0.7166	Intermediate Similarity	NPD4363	Phase 3
0.7161	Intermediate Similarity	NPD3225	Approved
0.716	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD7783	Phase 2
0.7143	Intermediate Similarity	NPD7700	Phase 2
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD7801	Approved
0.7143	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7699	Phase 2
0.7135	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4361	Phase 2
0.7118	Intermediate Similarity	NPD3226	Approved
0.7115	Intermediate Similarity	NPD2797	Approved
0.7108	Intermediate Similarity	NPD3887	Approved
0.7108	Intermediate Similarity	NPD2354	Approved
0.7098	Intermediate Similarity	NPD8319	Approved
0.7098	Intermediate Similarity	NPD8320	Phase 1
0.7089	Intermediate Similarity	NPD4908	Phase 1
0.7089	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6823	Phase 2
0.7081	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD230	Phase 1
0.7081	Intermediate Similarity	NPD5124	Phase 1
0.7078	Intermediate Similarity	NPD1610	Phase 2
0.7073	Intermediate Similarity	NPD7266	Discontinued
0.7055	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3027	Phase 3
0.7035	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7240	Approved
0.7025	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6100	Approved
0.7012	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD4662	Approved
0.6982	Remote Similarity	NPD4661	Approved
0.6975	Remote Similarity	NPD447	Suspended
0.6975	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5710	Approved
0.6966	Remote Similarity	NPD5711	Approved
0.6951	Remote Similarity	NPD4308	Phase 3
0.695	Remote Similarity	NPD7930	Approved
0.6941	Remote Similarity	NPD5049	Phase 3
0.6935	Remote Similarity	NPD8150	Discontinued
0.6928	Remote Similarity	NPD2424	Discontinued
0.6928	Remote Similarity	NPD9545	Approved
0.6923	Remote Similarity	NPD1729	Discontinued
0.6923	Remote Similarity	NPD7390	Discontinued
0.6914	Remote Similarity	NPD4288	Approved
0.6914	Remote Similarity	NPD4060	Phase 1

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