NPASS Compound

Structure

CID273021 OpenBabel06191716082D 28 32 0 0 0 0 0 0 0 0999 V2000 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 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 1.7321 -0.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6010 4.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 3.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 4.8090 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 22 1 0 0 0 0 2 22 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 13 1 0 0 0 0 5 16 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 22 1 0 0 0 0 8 14 2 0 0 0 0 8 18 1 0 0 0 0 9 17 2 0 0 0 0 9 19 1 0 0 0 0 10 15 2 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 11 27 1 0 0 0 0 12 16 2 0 0 0 0 12 21 1 0 0 0 0 13 20 1 0 0 0 0 13 21 2 0 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 16 28 1 0 0 0 0 17 24 1 0 0 0 0 18 19 2 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 23 2 0 0 0 0 21 25 1 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.11
Volume:	375.299
LogP:	4.627
LogD:	3.723
LogS:	-5.664
# Rotatable Bonds:	2
TPSA:	67.13
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.659
Synthetic Accessibility Score:	2.9
Fsp3:	0.227
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:	-4.988
MDCK Permeability:	2.9256783818709664e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	96.3164291381836%
Volume Distribution (VD):	0.321
Pgp-substrate:	4.195736885070801%

ADMET: Metabolism

CYP1A2-inhibitor:	0.9
CYP1A2-substrate:	0.353
CYP2C19-inhibitor:	0.967
CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.906
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.899
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.942
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	8.576
Half-life (T1/2):	0.158

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.896
Drug-inuced Liver Injury (DILI):	0.905
AMES Toxicity:	0.2
Rat Oral Acute Toxicity:	0.202
Maximum Recommended Daily Dose:	0.557
Skin Sensitization:	0.166
Carcinogencity:	0.938
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.927

Download Data

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

Natural Product: NPC273021

Natural Product ID:	NPC273021
*Common Name:**	Jamaicin
IUPAC Name:	3-(6-methoxy-1,3-benzodioxol-5-yl)-8,8-dimethylpyrano[2,3-f]chromen-4-one
Synonyms:
Standard InCHIKey:	WITLAWYGGVAFLU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H18O6/c1-22(2)7-6-12-16(28-22)5-4-13-20(23)15(10-25-21(12)13)14-8-18-19(27-11-26-18)9-17(14)24-3/h4-10H,11H2,1-3H3
SMILES:	CC1(C)C=Cc2c(ccc3c(=O)c(coc23)c2cc3c(cc2OC)OCO3)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3758966
PubChem CID:	12304682
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0003530] Pyranoisoflavonoids

*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
NPO29483	Swartzia schomburgkii	Species	Fabaceae	Eukaryota	n.a.	suriname rainforest	n.a.	PMID[11087583]
NPO28682	Jatropha multifida	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19036584]
NPO28682	Jatropha multifida	Species	Euphorbiaceae	Eukaryota	stems	Botanical Garden, Osmania University, Hyderabad, Andhra Pradesh	2006-AUG	PMID[21534583]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25590529]
NPO448	Millettia usaramensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26651537]
NPO29252	Moneses uniflora	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984155]
NPO29132	Agaricus campestris	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28711	Artabotrys hexapetalus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28711	Artabotrys hexapetalus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29132	Agaricus campestris	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO448	Millettia usaramensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28711	Artabotrys hexapetalus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29132	Agaricus campestris	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28767	Siparuna apiosyce	Species	Siparunaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29483	Swartzia schomburgkii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29132	Agaricus campestris	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29288	Diplorhynchus condylocarpon	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29393	Hapalopilus rutilans	Species	Phanerochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29339	Didemnum moseleyi	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29269	Celsia roripifolia	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28728	Scutellaria planipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28664	Hydrangea arborescens	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO448	Millettia usaramensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28699	Vincetoxicum nigrum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28798	Calophyllum macrocarpum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29022	Sarcococca wallichii	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28711	Artabotrys hexapetalus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29252	Moneses uniflora	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28910	Dacus cucumis	Species	Tephritidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28682	Jatropha multifida	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28606	Lemaireocereus thurberi	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29164	Lophostemon confertus	Species	Myrtaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT757	Organism	Plasmodium falciparum 3D7	Plasmodium falciparum 3D7	Inhibition	=	94.0	%	PMID[528196]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Inhibition	=	81.0	%	PMID[528196]

☑ 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 NPC273021 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	534
0.1-0.2	2194
0.2-0.3	5152
0.3-0.4	11544
0.4-0.5	6154
0.5-0.6	4204
0.6-0.7	5940
0.7-0.8	4939
0.8-0.85	1737
0.85-0.9	254
0.9-0.95	42
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC18284
0.9675	High Similarity	NPC113055
0.9551	High Similarity	NPC34376
0.9542	High Similarity	NPC128961
0.949	High Similarity	NPC302741
0.9484	High Similarity	NPC19097
0.9484	High Similarity	NPC310206
0.9481	High Similarity	NPC478238
0.9419	High Similarity	NPC180340
0.9416	High Similarity	NPC478213
0.9416	High Similarity	NPC472408
0.9412	High Similarity	NPC279061
0.9359	High Similarity	NPC258644
0.9351	High Similarity	NPC148497
0.9351	High Similarity	NPC52623
0.9351	High Similarity	NPC292460
0.9351	High Similarity	NPC166201
0.9351	High Similarity	NPC68882
0.9351	High Similarity	NPC153008
0.9321	High Similarity	NPC475825
0.9321	High Similarity	NPC223375
0.9295	High Similarity	NPC155063
0.929	High Similarity	NPC57211
0.929	High Similarity	NPC244371
0.9245	High Similarity	NPC478199
0.9221	High Similarity	NPC5840
0.9221	High Similarity	NPC189270
0.9212	High Similarity	NPC67302
0.9198	High Similarity	NPC471287
0.9182	High Similarity	NPC94155
0.9177	High Similarity	NPC257914
0.9177	High Similarity	NPC238405
0.9177	High Similarity	NPC104459
0.9152	High Similarity	NPC156635
0.9125	High Similarity	NPC261470
0.9119	High Similarity	NPC298093
0.9108	High Similarity	NPC284353
0.9103	High Similarity	NPC40033
0.9074	High Similarity	NPC113093
0.9062	High Similarity	NPC40037
0.9062	High Similarity	NPC165549
0.9057	High Similarity	NPC215375
0.9057	High Similarity	NPC62518
0.9051	High Similarity	NPC248299
0.9045	High Similarity	NPC279930
0.9045	High Similarity	NPC186507
0.903	High Similarity	NPC72455
0.9026	High Similarity	NPC205522
0.9018	High Similarity	NPC471288
0.9018	High Similarity	NPC135345
0.9012	High Similarity	NPC50960
0.9012	High Similarity	NPC470773
0.9006	High Similarity	NPC125991
0.9	High Similarity	NPC131557
0.8994	High Similarity	NPC476981
0.8994	High Similarity	NPC167595
0.8981	High Similarity	NPC144162
0.8976	High Similarity	NPC472607
0.8968	High Similarity	NPC63256
0.8968	High Similarity	NPC10304
0.8963	High Similarity	NPC41853
0.8961	High Similarity	NPC40818
0.8961	High Similarity	NPC216314
0.8961	High Similarity	NPC120924
0.8961	High Similarity	NPC106461
0.8961	High Similarity	NPC110639
0.8961	High Similarity	NPC195919
0.8961	High Similarity	NPC14958
0.8961	High Similarity	NPC215932
0.8957	High Similarity	NPC173292
0.8954	High Similarity	NPC182842
0.8951	High Similarity	NPC65846
0.8944	High Similarity	NPC259456
0.8944	High Similarity	NPC260640
0.8944	High Similarity	NPC295009
0.8935	High Similarity	NPC473883
0.8922	High Similarity	NPC257714
0.891	High Similarity	NPC238366
0.8909	High Similarity	NPC472276
0.8909	High Similarity	NPC105511
0.8903	High Similarity	NPC85233
0.8902	High Similarity	NPC167479
0.8896	High Similarity	NPC296575
0.8896	High Similarity	NPC471590
0.8896	High Similarity	NPC136278
0.8896	High Similarity	NPC224687
0.8896	High Similarity	NPC165512
0.8896	High Similarity	NPC475369
0.8889	High Similarity	NPC81679
0.8889	High Similarity	NPC472448
0.8889	High Similarity	NPC83922
0.8889	High Similarity	NPC469575
0.8882	High Similarity	NPC476980
0.8882	High Similarity	NPC225624
0.8882	High Similarity	NPC285973
0.8875	High Similarity	NPC78071
0.8862	High Similarity	NPC66804
0.8855	High Similarity	NPC48773
0.8855	High Similarity	NPC205076
0.8855	High Similarity	NPC307518
0.8855	High Similarity	NPC475155
0.8855	High Similarity	NPC235575
0.8848	High Similarity	NPC152477
0.8848	High Similarity	NPC211309
0.8848	High Similarity	NPC242395
0.8846	High Similarity	NPC476342
0.8841	High Similarity	NPC128293
0.8839	High Similarity	NPC302408
0.8839	High Similarity	NPC231013
0.8839	High Similarity	NPC283002
0.8834	High Similarity	NPC470178
0.8834	High Similarity	NPC470772
0.8831	High Similarity	NPC113089
0.8831	High Similarity	NPC23955
0.8827	High Similarity	NPC162668
0.8827	High Similarity	NPC167678
0.8827	High Similarity	NPC29876
0.8827	High Similarity	NPC470756
0.882	High Similarity	NPC184755
0.882	High Similarity	NPC187792
0.882	High Similarity	NPC74178
0.8805	High Similarity	NPC280937
0.8802	High Similarity	NPC62640
0.8802	High Similarity	NPC310794
0.8797	High Similarity	NPC198615
0.8795	High Similarity	NPC44558
0.8795	High Similarity	NPC212748
0.8795	High Similarity	NPC474434
0.8795	High Similarity	NPC224462
0.879	High Similarity	NPC69752
0.8788	High Similarity	NPC8965
0.8788	High Similarity	NPC76482
0.8788	High Similarity	NPC93099
0.878	High Similarity	NPC187923
0.8773	High Similarity	NPC229632
0.8766	High Similarity	NPC9966
0.8766	High Similarity	NPC476054
0.8766	High Similarity	NPC70853
0.8765	High Similarity	NPC204290
0.8765	High Similarity	NPC43971
0.8765	High Similarity	NPC19554
0.8765	High Similarity	NPC74749
0.8765	High Similarity	NPC269906
0.8765	High Similarity	NPC328102
0.8758	High Similarity	NPC473272
0.8758	High Similarity	NPC284820
0.8757	High Similarity	NPC168584
0.8743	High Similarity	NPC121333
0.8742	High Similarity	NPC35544
0.8742	High Similarity	NPC104728
0.8735	High Similarity	NPC58053
0.8735	High Similarity	NPC477165
0.8735	High Similarity	NPC226294
0.8735	High Similarity	NPC186807
0.8735	High Similarity	NPC183036
0.8735	High Similarity	NPC469931
0.8735	High Similarity	NPC93337
0.8735	High Similarity	NPC45638
0.8735	High Similarity	NPC95855
0.8735	High Similarity	NPC288813
0.8735	High Similarity	NPC472383
0.8735	High Similarity	NPC105025
0.8735	High Similarity	NPC475942
0.8735	High Similarity	NPC210042
0.8735	High Similarity	NPC201292
0.8735	High Similarity	NPC472381
0.8734	High Similarity	NPC201547
0.8734	High Similarity	NPC29056
0.8734	High Similarity	NPC259058
0.8727	High Similarity	NPC67450
0.8727	High Similarity	NPC120593
0.8727	High Similarity	NPC210460
0.8727	High Similarity	NPC155264
0.8727	High Similarity	NPC193881
0.872	High Similarity	NPC303460
0.872	High Similarity	NPC124038
0.872	High Similarity	NPC273959
0.872	High Similarity	NPC306321
0.8712	High Similarity	NPC198829
0.8712	High Similarity	NPC182045
0.8712	High Similarity	NPC258331
0.8712	High Similarity	NPC471290
0.871	High Similarity	NPC293201
0.8704	High Similarity	NPC204879
0.8701	High Similarity	NPC214919
0.8701	High Similarity	NPC29536
0.8701	High Similarity	NPC185607
0.8701	High Similarity	NPC124467
0.8696	High Similarity	NPC276444
0.8696	High Similarity	NPC303255
0.8696	High Similarity	NPC282307
0.8696	High Similarity	NPC472455
0.8696	High Similarity	NPC170026
0.8696	High Similarity	NPC301897
0.8696	High Similarity	NPC471985
0.8688	High Similarity	NPC472915
0.8688	High Similarity	NPC168805
0.8688	High Similarity	NPC121910
0.8683	High Similarity	NPC34287
0.8683	High Similarity	NPC21190

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 NPC273021 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	449
0.1-0.2	1043
0.2-0.3	1995
0.3-0.4	2767
0.4-0.5	1715
0.5-0.6	796
0.6-0.7	257
0.7-0.8	105
0.8-0.85	21
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9119	High Similarity	NPD5494	Approved
0.8788	High Similarity	NPD3818	Discontinued
0.8598	High Similarity	NPD1247	Approved
0.8571	High Similarity	NPD2801	Approved
0.8428	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD3817	Phase 2
0.8402	Intermediate Similarity	NPD7054	Approved
0.8364	Intermediate Similarity	NPD919	Approved
0.8354	Intermediate Similarity	NPD3882	Suspended
0.8353	Intermediate Similarity	NPD7074	Phase 3
0.8353	Intermediate Similarity	NPD7472	Approved
0.8344	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD1934	Approved
0.8258	Intermediate Similarity	NPD2796	Approved
0.8208	Intermediate Similarity	NPD7808	Phase 3
0.8199	Intermediate Similarity	NPD920	Approved
0.8198	Intermediate Similarity	NPD6797	Phase 2
0.815	Intermediate Similarity	NPD7251	Discontinued
0.8081	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD5844	Phase 1
0.8075	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD5402	Approved
0.8061	Intermediate Similarity	NPD6801	Discontinued
0.8059	Intermediate Similarity	NPD3926	Phase 2
0.8049	Intermediate Similarity	NPD4380	Phase 2
0.8046	Intermediate Similarity	NPD6559	Discontinued
0.8012	Intermediate Similarity	NPD1511	Approved
0.8012	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7819	Suspended
0.8012	Intermediate Similarity	NPD6166	Phase 2
0.8012	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1512	Approved
0.7901	Intermediate Similarity	NPD6799	Approved
0.7895	Intermediate Similarity	NPD6232	Discontinued
0.7892	Intermediate Similarity	NPD7411	Suspended
0.7875	Intermediate Similarity	NPD1243	Approved
0.787	Intermediate Similarity	NPD7075	Discontinued
0.7861	Intermediate Similarity	NPD7473	Discontinued
0.784	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1933	Approved
0.7736	Intermediate Similarity	NPD1510	Phase 2
0.7733	Intermediate Similarity	NPD7199	Phase 2
0.7725	Intermediate Similarity	NPD6599	Discontinued
0.7702	Intermediate Similarity	NPD1549	Phase 2
0.7683	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5403	Approved
0.765	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5401	Approved
0.7633	Intermediate Similarity	NPD37	Approved
0.763	Intermediate Similarity	NPD6959	Discontinued
0.7625	Intermediate Similarity	NPD3748	Approved
0.7602	Intermediate Similarity	NPD4967	Phase 2
0.7602	Intermediate Similarity	NPD4965	Approved
0.7602	Intermediate Similarity	NPD4966	Approved
0.7588	Intermediate Similarity	NPD1465	Phase 2
0.7578	Intermediate Similarity	NPD2935	Discontinued
0.7569	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD3749	Approved
0.7546	Intermediate Similarity	NPD2800	Approved
0.753	Intermediate Similarity	NPD2532	Approved
0.753	Intermediate Similarity	NPD2534	Approved
0.753	Intermediate Similarity	NPD2533	Approved
0.7514	Intermediate Similarity	NPD6234	Discontinued
0.7514	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7486	Intermediate Similarity	NPD3787	Discontinued
0.7486	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1240	Approved
0.7439	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1653	Approved
0.7394	Intermediate Similarity	NPD3750	Approved
0.7394	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1607	Approved
0.7368	Intermediate Similarity	NPD6777	Approved
0.7368	Intermediate Similarity	NPD6780	Approved
0.7368	Intermediate Similarity	NPD6776	Approved
0.7368	Intermediate Similarity	NPD6778	Approved
0.7368	Intermediate Similarity	NPD6782	Approved
0.7368	Intermediate Similarity	NPD6781	Approved
0.7368	Intermediate Similarity	NPD6779	Approved
0.7358	Intermediate Similarity	NPD2313	Discontinued
0.7348	Intermediate Similarity	NPD7685	Pre-registration
0.7345	Intermediate Similarity	NPD5242	Approved
0.7329	Intermediate Similarity	NPD447	Suspended
0.7318	Intermediate Similarity	NPD7228	Approved
0.7303	Intermediate Similarity	NPD2403	Approved
0.7301	Intermediate Similarity	NPD2799	Discontinued
0.7278	Intermediate Similarity	NPD7286	Phase 2
0.7273	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8312	Approved
0.7268	Intermediate Similarity	NPD8313	Approved
0.7267	Intermediate Similarity	NPD943	Approved
0.7254	Intermediate Similarity	NPD7435	Discontinued
0.7254	Intermediate Similarity	NPD7696	Phase 3
0.7254	Intermediate Similarity	NPD7698	Approved
0.7254	Intermediate Similarity	NPD7697	Approved
0.7251	Intermediate Similarity	NPD7458	Discontinued
0.7251	Intermediate Similarity	NPD3226	Approved
0.725	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6832	Phase 2
0.7231	Intermediate Similarity	NPD7584	Approved
0.7222	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7870	Phase 2
0.7216	Intermediate Similarity	NPD7871	Phase 2
0.7215	Intermediate Similarity	NPD2798	Approved
0.7213	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2346	Discontinued
0.7202	Intermediate Similarity	NPD5005	Approved
0.7202	Intermediate Similarity	NPD5006	Approved
0.7198	Intermediate Similarity	NPD5953	Discontinued
0.7188	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6385	Approved
0.7168	Intermediate Similarity	NPD6386	Approved
0.7158	Intermediate Similarity	NPD7240	Approved
0.7152	Intermediate Similarity	NPD1551	Phase 2
0.7151	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD5353	Approved
0.7117	Intermediate Similarity	NPD230	Phase 1
0.7115	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6823	Phase 2
0.7111	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2344	Approved
0.7107	Intermediate Similarity	NPD7701	Phase 2
0.7105	Intermediate Similarity	NPD6534	Approved
0.7105	Intermediate Similarity	NPD6535	Approved
0.7095	Intermediate Similarity	NPD7229	Phase 3
0.7085	Intermediate Similarity	NPD7783	Phase 2
0.7085	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4628	Phase 3
0.7083	Intermediate Similarity	NPD4420	Approved
0.7071	Intermediate Similarity	NPD8151	Discontinued
0.7035	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7874	Approved
0.7033	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6844	Discontinued
0.7024	Intermediate Similarity	NPD2654	Approved
0.7011	Intermediate Similarity	NPD7028	Phase 2
0.7006	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3705	Approved
0.7006	Intermediate Similarity	NPD1471	Phase 3
0.7	Intermediate Similarity	NPD5710	Approved
0.7	Intermediate Similarity	NPD5711	Approved
0.7	Intermediate Similarity	NPD7801	Approved
0.6995	Remote Similarity	NPD7699	Phase 2
0.6995	Remote Similarity	NPD7700	Phase 2
0.6989	Remote Similarity	NPD8455	Phase 2
0.6988	Remote Similarity	NPD7033	Discontinued
0.6988	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5890	Approved
0.6971	Remote Similarity	NPD5889	Approved
0.697	Remote Similarity	NPD6651	Approved
0.6951	Remote Similarity	NPD1613	Approved
0.6951	Remote Similarity	NPD4307	Phase 2
0.6951	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6190	Approved
0.6941	Remote Similarity	NPD2309	Approved
0.6935	Remote Similarity	NPD7549	Discontinued
0.6914	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6585	Discontinued
0.6909	Remote Similarity	NPD5124	Phase 1
0.6909	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5536	Phase 2
0.6884	Remote Similarity	NPD7583	Approved
0.6882	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD8150	Discontinued
0.6872	Remote Similarity	NPD8285	Discontinued
0.6871	Remote Similarity	NPD3027	Phase 3
0.686	Remote Similarity	NPD7390	Discontinued
0.6852	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD8127	Discontinued
0.685	Remote Similarity	NPD7585	Approved
0.6845	Remote Similarity	NPD6099	Approved
0.6845	Remote Similarity	NPD6100	Approved
0.6842	Remote Similarity	NPD3887	Approved
0.6839	Remote Similarity	NPD4363	Phase 3
0.6839	Remote Similarity	NPD4360	Phase 2
0.6836	Remote Similarity	NPD6280	Approved
0.6836	Remote Similarity	NPD6279	Approved
0.6833	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3266	Approved
0.6832	Remote Similarity	NPD3267	Approved
0.6829	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6674	Discontinued
0.6821	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6808	Phase 2
0.6804	Remote Similarity	NPD4362	Clinical (unspecified phase)

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