NPASS Compound

Structure

CID148423 OpenBabel06191715522D 22 25 0 0 0 0 0 0 0 0999 V2000 -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 2.0000 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 4.3301 1.5000 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 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 -0.8660 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 21 1 0 0 0 0 9 13 1 0 0 0 0 9 14 2 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 12 18 2 0 0 0 0 13 17 1 0 0 0 0 13 19 2 0 0 0 0 14 22 1 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 18 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.07
Volume:	297.091
LogP:	4.527
LogD:	3.08
LogS:	-5.791
# Rotatable Bonds:	2
TPSA:	52.58
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.555
Synthetic Accessibility Score:	2.329
Fsp3:	0.056
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:	-4.755
MDCK Permeability:	2.204733573307749e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.848
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	93.64643096923828%
Volume Distribution (VD):	0.508
Pgp-substrate:	6.2245869636535645%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.833
CYP2C19-inhibitor:	0.93
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.833
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.497
CYP2D6-substrate:	0.869
CYP3A4-inhibitor:	0.59
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	4.235
Half-life (T1/2):	0.2

ADMET: Toxicity

hERG Blockers:	0.204
Human Hepatotoxicity (H-HT):	0.069
Drug-inuced Liver Injury (DILI):	0.919
AMES Toxicity:	0.543
Rat Oral Acute Toxicity:	0.43
Maximum Recommended Daily Dose:	0.487
Skin Sensitization:	0.516
Carcinogencity:	0.665
Eye Corrosion:	0.003
Eye Irritation:	0.87
Respiratory Toxicity:	0.793

Download Data

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

Natural Product: NPC148423

Natural Product ID:	NPC148423
*Common Name:**	Pinnatin
IUPAC Name:	4-methoxy-7-phenylfuro[3,2-g]chromen-5-one
Synonyms:	Pinnatin
Standard InCHIKey:	QNWOJWLIFBMWKQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12O4/c1-20-18-12-7-8-21-15(12)10-16-17(18)13(19)9-14(22-16)11-5-3-2-4-6-11/h2-10H,1H3
SMILES:	COc1c2c(=O)cc(oc2cc2c1cco2)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL395770
PubChem CID:	5320607
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001759] Furanoflavones

*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
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[10.1016/j.tet.2012.03.006]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/j.tet.2012.03.006]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	stem bark	Indonesia	1999-SEP	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[14510596]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[16317898]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[17449162]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[19235686]
NPO3037	Derris indica	Species	Fabaceae	Eukaryota	root	n.a.	n.a.	PMID[19515570]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19666019]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[22707864]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23088673]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[2393954]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	dry stem	n.a.	n.a.	PMID[25466192]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[25594733]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29482940]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[7912074]
NPO17794	Streptomyces violaceusniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8557611]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15028	Lespedeza cuneata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15028	Lespedeza cuneata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19432	Millettia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15028	Lespedeza cuneata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28332	Lecidea tumida	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15028	Lespedeza cuneata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27972	Clitocybe phosphorea	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28007	Cakile maritima	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6223	Ceiba insignis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19432	Millettia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28142	Anthoceros agrestis	Species	Anthocerotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28157	Vriesea regina	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28299	Leucaena diversifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27863	Diospyros nigra	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17794	Streptomyces violaceusniger	Species	Streptomycetaceae	Bacteria	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	2
MIC	1
Others	3

Activity Type	# Activity
Cell Line	1
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	>	100000.0	nM	PMID[494486]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	23.7	n.a.	PMID[494483]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	34.8	mm	PMID[494483]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Preventive_index	=	31.3	n.a.	PMID[494483]
NPT2	Others	Unspecified		IC50	=	36.5	%	PMID[494484]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	12.5	ug.mL-1	PMID[494485]

☑ 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 NPC148423 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	582
0.1-0.2	2154
0.2-0.3	5126
0.3-0.4	12286
0.4-0.5	5589
0.5-0.6	5020
0.6-0.7	5615
0.7-0.8	4240
0.8-0.85	1591
0.85-0.9	442
0.9-0.95	42
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC135303
0.9862	High Similarity	NPC130015
0.9862	High Similarity	NPC38361
0.986	High Similarity	NPC306788
0.9795	High Similarity	NPC41719
0.9793	High Similarity	NPC472407
0.979	High Similarity	NPC198427
0.9728	High Similarity	NPC233776
0.972	High Similarity	NPC190572
0.9592	High Similarity	NPC263676
0.9589	High Similarity	NPC472406
0.9392	High Similarity	NPC116604
0.9388	High Similarity	NPC88445
0.9346	High Similarity	NPC193998
0.9324	High Similarity	NPC191104
0.931	High Similarity	NPC17262
0.9286	High Similarity	NPC65846
0.9252	High Similarity	NPC304443
0.9252	High Similarity	NPC74539
0.92	High Similarity	NPC253872
0.9145	High Similarity	NPC160015
0.9145	High Similarity	NPC247677
0.9139	High Similarity	NPC213608
0.9139	High Similarity	NPC122365
0.9139	High Similarity	NPC1477
0.9128	High Similarity	NPC226644
0.9128	High Similarity	NPC37226
0.9116	High Similarity	NPC246903
0.9103	High Similarity	NPC38914
0.9097	High Similarity	NPC219861
0.9091	High Similarity	NPC29638
0.9085	High Similarity	NPC65504
0.9085	High Similarity	NPC260902
0.9085	High Similarity	NPC296957
0.9073	High Similarity	NPC5871
0.9073	High Similarity	NPC67654
0.906	High Similarity	NPC266743
0.9051	High Similarity	NPC41853
0.9041	High Similarity	NPC22467
0.9032	High Similarity	NPC304387
0.9026	High Similarity	NPC476349
0.9026	High Similarity	NPC476350
0.9013	High Similarity	NPC472462
0.9007	High Similarity	NPC156244
0.9007	High Similarity	NPC170169
0.9	High Similarity	NPC37208
0.9	High Similarity	NPC296030
0.9	High Similarity	NPC221868
0.9	High Similarity	NPC317492
0.9	High Similarity	NPC39929
0.8993	High Similarity	NPC130581
0.8993	High Similarity	NPC12148
0.8987	High Similarity	NPC167479
0.8987	High Similarity	NPC241820
0.8986	High Similarity	NPC208584
0.898	High Similarity	NPC51146
0.898	High Similarity	NPC313036
0.898	High Similarity	NPC166858
0.8961	High Similarity	NPC269495
0.8958	High Similarity	NPC254741
0.8954	High Similarity	NPC278010
0.8954	High Similarity	NPC198490
0.8954	High Similarity	NPC250769
0.8954	High Similarity	NPC295608
0.894	High Similarity	NPC230713
0.894	High Similarity	NPC78335
0.8933	High Similarity	NPC135325
0.8933	High Similarity	NPC168085
0.8933	High Similarity	NPC272194
0.8926	High Similarity	NPC51641
0.8926	High Similarity	NPC300267
0.8926	High Similarity	NPC210826
0.8919	High Similarity	NPC225884
0.8919	High Similarity	NPC302181
0.8917	High Similarity	NPC472581
0.8917	High Similarity	NPC109180
0.891	High Similarity	NPC264293
0.8903	High Similarity	NPC40583
0.8889	High Similarity	NPC183874
0.8889	High Similarity	NPC131725
0.8882	High Similarity	NPC62640
0.8881	High Similarity	NPC292998
0.8875	High Similarity	NPC190351
0.8874	High Similarity	NPC178202
0.8867	High Similarity	NPC17816
0.8859	High Similarity	NPC230943
0.8859	High Similarity	NPC179970
0.8851	High Similarity	NPC53192
0.8846	High Similarity	NPC169
0.8846	High Similarity	NPC49009
0.8839	High Similarity	NPC270044
0.8839	High Similarity	NPC268360
0.8831	High Similarity	NPC148938
0.8828	High Similarity	NPC161196
0.8816	High Similarity	NPC155882
0.8811	High Similarity	NPC182428
0.879	High Similarity	NPC14822
0.8784	High Similarity	NPC254010
0.8782	High Similarity	NPC250076
0.8782	High Similarity	NPC472877
0.8776	High Similarity	NPC136095
0.8776	High Similarity	NPC262635
0.8776	High Similarity	NPC11566
0.8767	High Similarity	NPC259685
0.8766	High Similarity	NPC235333
0.8766	High Similarity	NPC72370
0.8758	High Similarity	NPC115324
0.875	High Similarity	NPC223354
0.8742	High Similarity	NPC471285
0.8742	High Similarity	NPC136641
0.8741	High Similarity	NPC278556
0.8741	High Similarity	NPC284424
0.8733	High Similarity	NPC311741
0.8733	High Similarity	NPC271590
0.8733	High Similarity	NPC234629
0.8733	High Similarity	NPC155144
0.8733	High Similarity	NPC110776
0.8733	High Similarity	NPC98926
0.8726	High Similarity	NPC95472
0.8726	High Similarity	NPC239270
0.8726	High Similarity	NPC303210
0.8726	High Similarity	NPC260296
0.8726	High Similarity	NPC115432
0.8718	High Similarity	NPC96342
0.8718	High Similarity	NPC212967
0.8718	High Similarity	NPC246647
0.8718	High Similarity	NPC164110
0.8716	High Similarity	NPC101366
0.8716	High Similarity	NPC472409
0.8716	High Similarity	NPC28337
0.8712	High Similarity	NPC66804
0.871	High Similarity	NPC297531
0.871	High Similarity	NPC99199
0.871	High Similarity	NPC213936
0.8707	High Similarity	NPC17848
0.8704	High Similarity	NPC157522
0.8701	High Similarity	NPC476238
0.8701	High Similarity	NPC327269
0.8701	High Similarity	NPC207624
0.8701	High Similarity	NPC31627
0.8693	High Similarity	NPC167576
0.8693	High Similarity	NPC321896
0.8693	High Similarity	NPC476185
0.869	High Similarity	NPC125269
0.8684	High Similarity	NPC266572
0.8684	High Similarity	NPC39195
0.8681	High Similarity	NPC473655
0.8681	High Similarity	NPC101294
0.8675	High Similarity	NPC476153
0.8675	High Similarity	NPC2416
0.8675	High Similarity	NPC215885
0.8671	High Similarity	NPC45124
0.8671	High Similarity	NPC30655
0.8671	High Similarity	NPC74854
0.8671	High Similarity	NPC472346
0.8667	High Similarity	NPC59522
0.8662	High Similarity	NPC244750
0.8658	High Similarity	NPC103362
0.8658	High Similarity	NPC110969
0.8658	High Similarity	NPC55832
0.8658	High Similarity	NPC268204
0.8658	High Similarity	NPC3188
0.8658	High Similarity	NPC52789
0.8658	High Similarity	NPC26051
0.8658	High Similarity	NPC469404
0.8654	High Similarity	NPC470625
0.8654	High Similarity	NPC180924
0.865	High Similarity	NPC72455
0.8649	High Similarity	NPC295384
0.8649	High Similarity	NPC18260
0.8649	High Similarity	NPC78913
0.8642	High Similarity	NPC131866
0.8639	High Similarity	NPC157855
0.8639	High Similarity	NPC103001
0.8636	High Similarity	NPC471675
0.8636	High Similarity	NPC23668
0.8636	High Similarity	NPC193976
0.8636	High Similarity	NPC106372
0.8636	High Similarity	NPC58668
0.863	High Similarity	NPC46869
0.863	High Similarity	NPC99854
0.8627	High Similarity	NPC214493
0.8621	High Similarity	NPC247743
0.8618	High Similarity	NPC201731
0.8618	High Similarity	NPC24673
0.8618	High Similarity	NPC97716
0.8618	High Similarity	NPC104406
0.8618	High Similarity	NPC237635
0.8618	High Similarity	NPC79469
0.8618	High Similarity	NPC308200
0.8609	High Similarity	NPC303185
0.8609	High Similarity	NPC184649
0.8609	High Similarity	NPC216538
0.8609	High Similarity	NPC124780
0.8609	High Similarity	NPC224714
0.8609	High Similarity	NPC273538
0.8609	High Similarity	NPC87486
0.8608	High Similarity	NPC304839
0.8608	High Similarity	NPC220582
0.8608	High Similarity	NPC243509

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 NPC148423 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	506
0.1-0.2	1008
0.2-0.3	1693
0.3-0.4	2823
0.4-0.5	1824
0.5-0.6	911
0.6-0.7	251
0.7-0.8	100
0.8-0.85	25
0.85-0.9	5
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9252	High Similarity	NPD920	Approved
0.9116	High Similarity	NPD642	Clinical (unspecified phase)
0.898	High Similarity	NPD643	Clinical (unspecified phase)
0.891	High Similarity	NPD1247	Approved
0.8828	High Similarity	NPD2796	Approved
0.8776	High Similarity	NPD1243	Approved
0.8609	High Similarity	NPD4378	Clinical (unspecified phase)
0.8544	High Similarity	NPD919	Approved
0.8516	High Similarity	NPD7411	Suspended
0.8378	Intermediate Similarity	NPD1510	Phase 2
0.8375	Intermediate Similarity	NPD5494	Approved
0.8366	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1549	Phase 2
0.8267	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD3749	Approved
0.8217	Intermediate Similarity	NPD4380	Phase 2
0.8204	Intermediate Similarity	NPD6559	Discontinued
0.8176	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7819	Suspended
0.8176	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD2344	Approved
0.8113	Intermediate Similarity	NPD6801	Discontinued
0.811	Intermediate Similarity	NPD3926	Phase 2
0.8108	Intermediate Similarity	NPD1240	Approved
0.8065	Intermediate Similarity	NPD6799	Approved
0.8039	Intermediate Similarity	NPD2800	Approved
0.8026	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7075	Discontinued
0.8013	Intermediate Similarity	NPD3748	Approved
0.8	Intermediate Similarity	NPD1607	Approved
0.8	Intermediate Similarity	NPD1934	Approved
0.7964	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD7768	Phase 2
0.7963	Intermediate Similarity	NPD3882	Suspended
0.795	Intermediate Similarity	NPD2801	Approved
0.7949	Intermediate Similarity	NPD1511	Approved
0.7935	Intermediate Similarity	NPD2309	Approved
0.7914	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD1471	Phase 3
0.7901	Intermediate Similarity	NPD3817	Phase 2
0.7879	Intermediate Similarity	NPD6959	Discontinued
0.7875	Intermediate Similarity	NPD6599	Discontinued
0.7857	Intermediate Similarity	NPD3818	Discontinued
0.7852	Intermediate Similarity	NPD2313	Discontinued
0.7848	Intermediate Similarity	NPD1512	Approved
0.7843	Intermediate Similarity	NPD1551	Phase 2
0.7756	Intermediate Similarity	NPD3750	Approved
0.7725	Intermediate Similarity	NPD6808	Phase 2
0.7724	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD3226	Approved
0.7673	Intermediate Similarity	NPD2533	Approved
0.7673	Intermediate Similarity	NPD5401	Approved
0.7673	Intermediate Similarity	NPD2534	Approved
0.7673	Intermediate Similarity	NPD2532	Approved
0.7669	Intermediate Similarity	NPD6280	Approved
0.7669	Intermediate Similarity	NPD6279	Approved
0.7662	Intermediate Similarity	NPD2799	Discontinued
0.7633	Intermediate Similarity	NPD6166	Phase 2
0.7633	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6232	Discontinued
0.7616	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6832	Phase 2
0.7588	Intermediate Similarity	NPD7473	Discontinued
0.7578	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD5403	Approved
0.7576	Intermediate Similarity	NPD5402	Approved
0.7532	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3267	Approved
0.7517	Intermediate Similarity	NPD3266	Approved
0.7516	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7468	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2654	Approved
0.7452	Intermediate Similarity	NPD2346	Discontinued
0.7427	Intermediate Similarity	NPD2403	Approved
0.7412	Intermediate Similarity	NPD7229	Phase 3
0.7399	Intermediate Similarity	NPD7054	Approved
0.7394	Intermediate Similarity	NPD5890	Approved
0.7394	Intermediate Similarity	NPD5889	Approved
0.7365	Intermediate Similarity	NPD2296	Approved
0.736	Intermediate Similarity	NPD8434	Phase 2
0.7356	Intermediate Similarity	NPD7074	Phase 3
0.7356	Intermediate Similarity	NPD7472	Approved
0.7351	Intermediate Similarity	NPD2798	Approved
0.7337	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6797	Phase 2
0.7308	Intermediate Similarity	NPD6651	Approved
0.7305	Intermediate Similarity	NPD5761	Phase 2
0.7305	Intermediate Similarity	NPD5760	Phase 2
0.729	Intermediate Similarity	NPD4307	Phase 2
0.7278	Intermediate Similarity	NPD4287	Approved
0.7273	Intermediate Similarity	NPD3268	Approved
0.7273	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7251	Discontinued
0.7244	Intermediate Similarity	NPD1933	Approved
0.7237	Intermediate Similarity	NPD1019	Discontinued
0.7232	Intermediate Similarity	NPD7808	Phase 3
0.7232	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6585	Discontinued
0.7222	Intermediate Similarity	NPD1241	Discontinued
0.7215	Intermediate Similarity	NPD7033	Discontinued
0.7205	Intermediate Similarity	NPD4628	Phase 3
0.72	Intermediate Similarity	NPD3972	Approved
0.7179	Intermediate Similarity	NPD943	Approved
0.7178	Intermediate Similarity	NPD7390	Discontinued
0.7174	Intermediate Similarity	NPD4361	Phase 2
0.7174	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1203	Approved
0.7161	Intermediate Similarity	NPD1296	Phase 2
0.716	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD1729	Discontinued
0.7143	Intermediate Similarity	NPD4908	Phase 1
0.712	Intermediate Similarity	NPD4363	Phase 3
0.712	Intermediate Similarity	NPD4360	Phase 2
0.7119	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5710	Approved
0.711	Intermediate Similarity	NPD5711	Approved
0.7107	Intermediate Similarity	NPD4308	Phase 3
0.7105	Intermediate Similarity	NPD1876	Approved
0.7101	Intermediate Similarity	NPD1465	Phase 2
0.7095	Intermediate Similarity	NPD1548	Phase 1
0.7086	Intermediate Similarity	NPD9717	Approved
0.7083	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4288	Approved
0.7051	Intermediate Similarity	NPD3764	Approved
0.7043	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1610	Phase 2
0.7	Intermediate Similarity	NPD17	Approved
0.6993	Remote Similarity	NPD3225	Approved
0.6964	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6100	Approved
0.6957	Remote Similarity	NPD6099	Approved
0.6954	Remote Similarity	NPD7199	Phase 2
0.6951	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3751	Discontinued
0.6948	Remote Similarity	NPD2797	Approved
0.6941	Remote Similarity	NPD6844	Discontinued
0.6918	Remote Similarity	NPD447	Suspended
0.6918	Remote Similarity	NPD5124	Phase 1
0.6918	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD230	Phase 1
0.6908	Remote Similarity	NPD422	Phase 1
0.689	Remote Similarity	NPD7003	Approved
0.689	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5242	Approved
0.6871	Remote Similarity	NPD2424	Discontinued
0.6867	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7458	Discontinued
0.6863	Remote Similarity	NPD1608	Approved
0.6855	Remote Similarity	NPD3140	Approved
0.6855	Remote Similarity	NPD3142	Approved
0.6848	Remote Similarity	NPD3887	Approved
0.6836	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6798	Discontinued
0.6828	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1651	Approved
0.6818	Remote Similarity	NPD3787	Discontinued
0.6815	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD8313	Approved
0.6813	Remote Similarity	NPD8312	Approved
0.6811	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.681	Remote Similarity	NPD2353	Approved
0.681	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7584	Approved
0.6802	Remote Similarity	NPD8455	Phase 2
0.6796	Remote Similarity	NPD6104	Discontinued
0.6789	Remote Similarity	NPD8285	Discontinued
0.6782	Remote Similarity	NPD6971	Discontinued
0.6772	Remote Similarity	NPD4625	Phase 3
0.676	Remote Similarity	NPD7177	Discontinued
0.676	Remote Similarity	NPD2163	Approved
0.6755	Remote Similarity	NPD9545	Approved
0.675	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.675	Remote Similarity	NPD2979	Phase 3
0.675	Remote Similarity	NPD1613	Approved
0.6748	Remote Similarity	NPD5405	Approved
0.6748	Remote Similarity	NPD5408	Approved
0.6748	Remote Similarity	NPD5406	Approved
0.6748	Remote Similarity	NPD5404	Approved
0.6746	Remote Similarity	NPD3869	Phase 3
0.6746	Remote Similarity	NPD3873	Phase 3
0.6744	Remote Similarity	NPD37	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data