NPASS Compound

Structure

NPC98083 OpenBabel07101718192D 33 37 0 0 1 0 0 0 0 0999 V2000 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 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 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 -3.0000 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 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 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 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 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 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 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 10 1 0 0 0 0 2 4 2 0 0 0 0 2 11 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 10 2 0 0 0 0 5 16 1 0 0 0 0 6 11 2 0 0 0 0 6 17 1 0 0 0 0 7 13 1 0 0 0 0 7 19 1 0 0 0 0 8 12 1 0 0 0 0 8 21 1 0 0 0 0 9 18 2 0 0 0 0 9 20 1 0 0 0 0 12 10 1 1 0 0 0 12 22 1 0 0 0 0 13 20 2 0 0 0 0 13 24 1 0 0 0 0 14 16 2 0 0 0 0 14 25 1 0 0 0 0 15 17 2 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 22 1 0 0 0 0 18 29 1 0 0 0 0 19 23 1 0 0 0 0 19 30 1 1 0 0 0 20 32 1 0 0 0 0 21 31 2 0 0 0 0 21 33 1 0 0 0 0 22 24 2 0 0 0 0 23 11 1 6 0 0 0 23 32 1 0 0 0 0 24 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.11
Volume:	433.625
LogP:	2.758
LogD:	1.989
LogS:	-4.105
# Rotatable Bonds:	2
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.195
Synthetic Accessibility Score:	3.999
Fsp3:	0.208
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.127
MDCK Permeability:	6.136098818387836e-06
Pgp-inhibitor:	0.016
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	89.7728042602539%
Volume Distribution (VD):	0.524
Pgp-substrate:	10.084108352661133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.716
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.234
CYP3A4-inhibitor:	0.162
CYP3A4-substrate:	0.434

ADMET: Excretion

Clearance (CL):	19.264
Half-life (T1/2):	0.833

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.632
AMES Toxicity:	0.593
Rat Oral Acute Toxicity:	0.838
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.95
Carcinogencity:	0.543
Eye Corrosion:	0.003
Eye Irritation:	0.895
Respiratory Toxicity:	0.43

Download Data

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

Natural Product: NPC98083

Natural Product ID:	NPC98083
*Common Name:**	Catechin-[5,6-E]-4Beta-(3,4-Dihydroxyphenyl)Dihydro-2(3H)-Pyranone
IUPAC Name:	(4S,8R,9S)-4,8-bis(3,4-dihydroxyphenyl)-5,9-dihydroxy-4,8,9,10-tetrahydro-3H-pyrano[2,3-h]chromen-2-one
Synonyms:
Standard InCHIKey:	AKZBEMDOKOHIFM-BIGSBDRZSA-N
Standard InCHI:	InChI=1S/C24H20O9/c25-14-3-1-10(5-16(14)27)12-8-21(31)33-24-13-7-19(30)23(11-2-4-15(26)17(28)6-11)32-20(13)9-18(29)22(12)24/h1-6,9,12,19,23,25-30H,7-8H2/t12-,19-,23+/m0/s1
SMILES:	O=C1C[C@@H](c2ccc(c(c2)O)O)c2c(O1)c1C[C@H](O)[C@H](Oc1cc2O)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2316619
PubChem CID:	71661208
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003012] Flavan-3-ols [CHEMONTID:0001584] Catechins

*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
NPO22355	Flacourtia indica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23354072]
NPO22355	Flacourtia indica	Species	Salicaceae	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	3
Others	3

Activity Type	# Activity
Cell Line	1
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	200000.0	nM	PMID[529851]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	>	5000.0	nM	PMID[529851]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	181.8	n.a.	PMID[529851]
NPT2	Others	Unspecified		Inhibition	=	23.0	%	PMID[529851]
NPT475	Organism	Plasmodium yoelii	Plasmodium yoelii	IC50	=	10100.0	nM	PMID[529851]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1100.0	nM	PMID[529851]

☑ 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 NPC98083 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	378
0.1-0.2	1584
0.2-0.3	3580
0.3-0.4	8770
0.4-0.5	9813
0.5-0.6	3694
0.6-0.7	5251
0.7-0.8	7860
0.8-0.85	1551
0.85-0.9	180
0.9-0.95	24
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC94220
1.0	High Similarity	NPC24339
1.0	High Similarity	NPC166456
1.0	High Similarity	NPC7543
0.9868	High Similarity	NPC109061
0.9739	High Similarity	NPC124747
0.9739	High Similarity	NPC155754
0.9735	High Similarity	NPC165483
0.9615	High Similarity	NPC9309
0.961	High Similarity	NPC177100
0.961	High Similarity	NPC139540
0.9172	High Similarity	NPC24164
0.9136	High Similarity	NPC65333
0.9097	High Similarity	NPC8712
0.908	High Similarity	NPC98583
0.9045	High Similarity	NPC114179
0.9045	High Similarity	NPC38779
0.9045	High Similarity	NPC156818
0.9045	High Similarity	NPC289322
0.9045	High Similarity	NPC68324
0.9045	High Similarity	NPC160512
0.9018	High Similarity	NPC271848
0.9018	High Similarity	NPC262580
0.9018	High Similarity	NPC81332
0.9018	High Similarity	NPC100251
0.9018	High Similarity	NPC212038
0.9018	High Similarity	NPC289396
0.9013	High Similarity	NPC18185
0.9013	High Similarity	NPC262911
0.9013	High Similarity	NPC294558
0.9013	High Similarity	NPC70409
0.9013	High Similarity	NPC263940
0.9013	High Similarity	NPC236202
0.9013	High Similarity	NPC204770
0.9013	High Similarity	NPC82917
0.9013	High Similarity	NPC170103
0.9013	High Similarity	NPC108811
0.9013	High Similarity	NPC58190
0.9013	High Similarity	NPC202742
0.8981	High Similarity	NPC291948
0.8981	High Similarity	NPC250436
0.8981	High Similarity	NPC318432
0.8981	High Similarity	NPC88803
0.8981	High Similarity	NPC104983
0.8981	High Similarity	NPC300845
0.8947	High Similarity	NPC96576
0.8931	High Similarity	NPC53889
0.8922	High Similarity	NPC53680
0.8922	High Similarity	NPC208797
0.891	High Similarity	NPC474656
0.8902	High Similarity	NPC186847
0.8902	High Similarity	NPC472454
0.8902	High Similarity	NPC257667
0.8896	High Similarity	NPC211561
0.8889	High Similarity	NPC471823
0.8889	High Similarity	NPC224851
0.8882	High Similarity	NPC121290
0.8875	High Similarity	NPC142252
0.8868	High Similarity	NPC87317
0.8867	High Similarity	NPC178054
0.8854	High Similarity	NPC268484
0.8846	High Similarity	NPC469944
0.8846	High Similarity	NPC226108
0.8846	High Similarity	NPC134911
0.8846	High Similarity	NPC46283
0.8846	High Similarity	NPC44192
0.8846	High Similarity	NPC322899
0.8846	High Similarity	NPC272552
0.8841	High Similarity	NPC180768
0.8834	High Similarity	NPC473818
0.8831	High Similarity	NPC20757
0.8831	High Similarity	NPC227516
0.8827	High Similarity	NPC142614
0.8827	High Similarity	NPC471788
0.8824	High Similarity	NPC268515
0.8824	High Similarity	NPC40222
0.882	High Similarity	NPC12326
0.882	High Similarity	NPC55121
0.879	High Similarity	NPC306267
0.879	High Similarity	NPC20050
0.879	High Similarity	NPC223720
0.8788	High Similarity	NPC67134
0.8788	High Similarity	NPC47140
0.8773	High Similarity	NPC13481
0.8773	High Similarity	NPC320741
0.8773	High Similarity	NPC171985
0.8773	High Similarity	NPC207575
0.8758	High Similarity	NPC97812
0.875	High Similarity	NPC117418
0.875	High Similarity	NPC53545
0.8743	High Similarity	NPC297574
0.8743	High Similarity	NPC67629
0.8743	High Similarity	NPC79736
0.8727	High Similarity	NPC102277
0.8727	High Similarity	NPC279209
0.8726	High Similarity	NPC279406
0.8726	High Similarity	NPC226809
0.872	High Similarity	NPC260266
0.8718	High Similarity	NPC477612
0.8712	High Similarity	NPC72787
0.8712	High Similarity	NPC7688
0.8712	High Similarity	NPC7154
0.8712	High Similarity	NPC58223
0.8712	High Similarity	NPC36916
0.8712	High Similarity	NPC125039
0.8712	High Similarity	NPC36
0.8704	High Similarity	NPC476371
0.8704	High Similarity	NPC476247
0.8704	High Similarity	NPC174311
0.8704	High Similarity	NPC476372
0.8704	High Similarity	NPC477841
0.8698	High Similarity	NPC125352
0.8698	High Similarity	NPC117668
0.8696	High Similarity	NPC24627
0.8693	High Similarity	NPC28440
0.8693	High Similarity	NPC171932
0.869	High Similarity	NPC267549
0.8688	High Similarity	NPC36077
0.8679	High Similarity	NPC292385
0.8679	High Similarity	NPC155015
0.8679	High Similarity	NPC142479
0.8679	High Similarity	NPC125709
0.8671	High Similarity	NPC178574
0.8671	High Similarity	NPC224161
0.8671	High Similarity	NPC65591
0.8667	High Similarity	NPC107627
0.8667	High Similarity	NPC475212
0.8659	High Similarity	NPC43065
0.865	High Similarity	NPC67959
0.865	High Similarity	NPC45943
0.8647	High Similarity	NPC321916
0.8647	High Similarity	NPC123259
0.8647	High Similarity	NPC129533
0.8647	High Similarity	NPC132111
0.8642	High Similarity	NPC305987
0.8642	High Similarity	NPC186228
0.8642	High Similarity	NPC113163
0.8642	High Similarity	NPC472632
0.8642	High Similarity	NPC103201
0.8642	High Similarity	NPC288131
0.8642	High Similarity	NPC473106
0.8642	High Similarity	NPC165970
0.8642	High Similarity	NPC66618
0.8642	High Similarity	NPC158188
0.8642	High Similarity	NPC289771
0.8642	High Similarity	NPC84324
0.8642	High Similarity	NPC26326
0.8642	High Similarity	NPC469889
0.8634	High Similarity	NPC36354
0.8618	High Similarity	NPC277331
0.8618	High Similarity	NPC100482
0.8616	High Similarity	NPC46335
0.8616	High Similarity	NPC7178
0.8616	High Similarity	NPC62903
0.8614	High Similarity	NPC91043
0.8614	High Similarity	NPC313304
0.8614	High Similarity	NPC78734
0.8614	High Similarity	NPC150767
0.8614	High Similarity	NPC476365
0.8614	High Similarity	NPC218488
0.8608	High Similarity	NPC264875
0.8608	High Similarity	NPC476434
0.8608	High Similarity	NPC163598
0.8608	High Similarity	NPC120774
0.8606	High Similarity	NPC14662
0.8598	High Similarity	NPC477840
0.8596	High Similarity	NPC318119
0.859	High Similarity	NPC476348
0.859	High Similarity	NPC187398
0.859	High Similarity	NPC142863
0.8589	High Similarity	NPC474033
0.8589	High Similarity	NPC471745
0.8589	High Similarity	NPC140346
0.8589	High Similarity	NPC192258
0.8589	High Similarity	NPC474034
0.8589	High Similarity	NPC476200
0.8589	High Similarity	NPC219927
0.8581	High Similarity	NPC260397
0.858	High Similarity	NPC476620
0.858	High Similarity	NPC476619
0.858	High Similarity	NPC292415
0.858	High Similarity	NPC476622
0.858	High Similarity	NPC101731
0.858	High Similarity	NPC476621
0.858	High Similarity	NPC476373
0.858	High Similarity	NPC476623
0.858	High Similarity	NPC289346
0.858	High Similarity	NPC174953
0.858	High Similarity	NPC476618
0.8571	High Similarity	NPC474055
0.8571	High Similarity	NPC473108
0.8571	High Similarity	NPC147743
0.8571	High Similarity	NPC108456
0.8571	High Similarity	NPC471209
0.8571	High Similarity	NPC4809
0.8571	High Similarity	NPC73517
0.8571	High Similarity	NPC472598
0.8571	High Similarity	NPC125495
0.8563	High Similarity	NPC256760
0.8563	High Similarity	NPC4200

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 NPC98083 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	889
0.2-0.3	1832
0.3-0.4	2612
0.4-0.5	1788
0.5-0.6	970
0.6-0.7	559
0.7-0.8	136
0.8-0.85	18
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8981	High Similarity	NPD4868	Clinical (unspecified phase)
0.8712	High Similarity	NPD6166	Phase 2
0.8712	High Similarity	NPD6167	Clinical (unspecified phase)
0.8712	High Similarity	NPD6168	Clinical (unspecified phase)
0.8675	High Similarity	NPD7993	Clinical (unspecified phase)
0.8667	High Similarity	NPD5844	Phase 1
0.85	High Similarity	NPD2393	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD7228	Approved
0.8415	Intermediate Similarity	NPD7199	Phase 2
0.8393	Intermediate Similarity	NPD7074	Phase 3
0.8385	Intermediate Similarity	NPD1465	Phase 2
0.8333	Intermediate Similarity	NPD1613	Approved
0.8333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7054	Approved
0.8323	Intermediate Similarity	NPD1934	Approved
0.8293	Intermediate Similarity	NPD6234	Discontinued
0.8284	Intermediate Similarity	NPD7472	Approved
0.8272	Intermediate Similarity	NPD8455	Phase 2
0.8235	Intermediate Similarity	NPD6797	Phase 2
0.8228	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD37	Approved
0.8204	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD4380	Phase 2
0.8187	Intermediate Similarity	NPD7251	Discontinued
0.8171	Intermediate Similarity	NPD4966	Approved
0.8171	Intermediate Similarity	NPD4965	Approved
0.8171	Intermediate Similarity	NPD4967	Phase 2
0.8144	Intermediate Similarity	NPD6232	Discontinued
0.814	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7075	Discontinued
0.811	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7473	Discontinued
0.8084	Intermediate Similarity	NPD6959	Discontinued
0.8079	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD3818	Discontinued
0.8037	Intermediate Similarity	NPD7411	Suspended
0.8035	Intermediate Similarity	NPD7808	Phase 3
0.8024	Intermediate Similarity	NPD5494	Approved
0.8012	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3817	Phase 2
0.7977	Intermediate Similarity	NPD7240	Approved
0.7963	Intermediate Similarity	NPD1653	Approved
0.7961	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD4908	Phase 1
0.7941	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7819	Suspended
0.7939	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD2801	Approved
0.7937	Intermediate Similarity	NPD1511	Approved
0.7925	Intermediate Similarity	NPD6190	Approved
0.7895	Intermediate Similarity	NPD3027	Phase 3
0.7879	Intermediate Similarity	NPD6801	Discontinued
0.784	Intermediate Similarity	NPD1512	Approved
0.7824	Intermediate Similarity	NPD3787	Discontinued
0.7824	Intermediate Similarity	NPD7229	Phase 3
0.7797	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD8313	Approved
0.7784	Intermediate Similarity	NPD8312	Approved
0.7771	Intermediate Similarity	NPD6559	Discontinued
0.7738	Intermediate Similarity	NPD7768	Phase 2
0.7738	Intermediate Similarity	NPD3882	Suspended
0.7727	Intermediate Similarity	NPD6798	Discontinued
0.7711	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5124	Phase 1
0.7688	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD5402	Approved
0.7673	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD8127	Discontinued
0.7647	Intermediate Similarity	NPD7680	Approved
0.7644	Intermediate Similarity	NPD3751	Discontinued
0.764	Intermediate Similarity	NPD4628	Phase 3
0.764	Intermediate Similarity	NPD3750	Approved
0.764	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD4060	Phase 1
0.7625	Intermediate Similarity	NPD1549	Phase 2
0.7622	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6100	Approved
0.761	Intermediate Similarity	NPD6099	Approved
0.7607	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1610	Phase 2
0.7588	Intermediate Similarity	NPD3749	Approved
0.758	Intermediate Similarity	NPD6355	Discontinued
0.7576	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5403	Approved
0.7564	Intermediate Similarity	NPD6233	Phase 2
0.7562	Intermediate Similarity	NPD7266	Discontinued
0.7528	Intermediate Similarity	NPD7549	Discontinued
0.75	Intermediate Similarity	NPD6799	Approved
0.7486	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7097	Phase 1
0.7472	Intermediate Similarity	NPD7685	Pre-registration
0.7469	Intermediate Similarity	NPD6674	Discontinued
0.7468	Intermediate Similarity	NPD230	Phase 1
0.7455	Intermediate Similarity	NPD5401	Approved
0.744	Intermediate Similarity	NPD6599	Discontinued
0.7438	Intermediate Similarity	NPD7033	Discontinued
0.7434	Intermediate Similarity	NPD1608	Approved
0.7419	Intermediate Similarity	NPD2861	Phase 2
0.7407	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2797	Approved
0.7389	Intermediate Similarity	NPD3268	Approved
0.7371	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7783	Phase 2
0.7362	Intermediate Similarity	NPD1652	Phase 2
0.7358	Intermediate Similarity	NPD8151	Discontinued
0.7349	Intermediate Similarity	NPD2534	Approved
0.7349	Intermediate Similarity	NPD2532	Approved
0.7349	Intermediate Similarity	NPD2533	Approved
0.7346	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6002	Phase 3
0.7346	Intermediate Similarity	NPD6005	Phase 3
0.7346	Intermediate Similarity	NPD6004	Phase 3
0.7346	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD919	Approved
0.7329	Intermediate Similarity	NPD1510	Phase 2
0.7329	Intermediate Similarity	NPD3748	Approved
0.7325	Intermediate Similarity	NPD4625	Phase 3
0.7317	Intermediate Similarity	NPD4110	Phase 3
0.7317	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD8166	Discontinued
0.7284	Intermediate Similarity	NPD2796	Approved
0.7284	Intermediate Similarity	NPD2935	Discontinued
0.7278	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3226	Approved
0.7278	Intermediate Similarity	NPD7458	Discontinued
0.7268	Intermediate Similarity	NPD8150	Discontinued
0.7256	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD17	Approved
0.7234	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3225	Approved
0.7219	Intermediate Similarity	NPD1548	Phase 1
0.7215	Intermediate Similarity	NPD7095	Approved
0.7202	Intermediate Similarity	NPD6273	Approved
0.7178	Intermediate Similarity	NPD1551	Phase 2
0.7178	Intermediate Similarity	NPD2438	Suspended
0.7161	Intermediate Similarity	NPD4749	Approved
0.716	Intermediate Similarity	NPD7427	Discontinued
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7134	Intermediate Similarity	NPD5762	Approved
0.7134	Intermediate Similarity	NPD5763	Approved
0.7108	Intermediate Similarity	NPD7003	Approved
0.7102	Intermediate Similarity	NPD6746	Phase 2
0.7099	Intermediate Similarity	NPD6653	Approved
0.7098	Intermediate Similarity	NPD7435	Discontinued
0.7083	Intermediate Similarity	NPD7212	Phase 2
0.7083	Intermediate Similarity	NPD7213	Phase 3
0.7083	Intermediate Similarity	NPD7390	Discontinued
0.7081	Intermediate Similarity	NPD943	Approved
0.7081	Intermediate Similarity	NPD8434	Phase 2
0.7081	Intermediate Similarity	NPD1240	Approved
0.7081	Intermediate Similarity	NPD4140	Approved
0.7079	Intermediate Similarity	NPD3926	Phase 2
0.7076	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD3266	Approved
0.707	Intermediate Similarity	NPD3267	Approved
0.7059	Intermediate Similarity	NPD920	Approved
0.7041	Intermediate Similarity	NPD7585	Approved
0.7041	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7447	Phase 1
0.7037	Intermediate Similarity	NPD447	Suspended
0.7033	Intermediate Similarity	NPD5953	Discontinued
0.7032	Intermediate Similarity	NPD1091	Approved
0.7031	Intermediate Similarity	NPD6780	Approved
0.7031	Intermediate Similarity	NPD6776	Approved
0.7031	Intermediate Similarity	NPD6777	Approved
0.7031	Intermediate Similarity	NPD6781	Approved
0.7031	Intermediate Similarity	NPD6779	Approved
0.7031	Intermediate Similarity	NPD6778	Approved
0.7031	Intermediate Similarity	NPD6782	Approved
0.7024	Intermediate Similarity	NPD6666	Approved
0.7024	Intermediate Similarity	NPD6667	Approved
0.7024	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4062	Phase 3
0.7012	Intermediate Similarity	NPD2799	Discontinued
0.701	Intermediate Similarity	NPD4004	Approved
0.701	Intermediate Similarity	NPD4002	Approved
0.7006	Intermediate Similarity	NPD1283	Approved
0.7	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7039	Approved
0.6995	Remote Similarity	NPD3452	Approved
0.6995	Remote Similarity	NPD2494	Approved
0.6995	Remote Similarity	NPD3450	Approved
0.6995	Remote Similarity	NPD7038	Approved
0.6995	Remote Similarity	NPD2493	Approved
0.6994	Remote Similarity	NPD1607	Approved
0.699	Remote Similarity	NPD7583	Approved
0.6988	Remote Similarity	NPD5958	Discontinued
0.6988	Remote Similarity	NPD2424	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data