NPASS Compound

Structure

NPC131466 OpenBabel07101719152D 46 51 0 0 1 0 0 0 0 0999 V2000 7.0628 -0.5309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5870 -2.0753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8020 0.5855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3567 -0.2884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2608 -1.9686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3868 0.5858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2608 1.9544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6951 -0.5191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 1.5452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9595 -2.9494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1027 1.9589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1102 -2.4590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2075 1.4426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9252 1.4247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4114 -1.4782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1102 0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5077 3.4256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8332 0.6492 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5621 -0.9879 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9595 -0.0071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6583 2.9352 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2608 -0.9879 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8089 -2.4590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7712 1.5136 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5621 -0.0071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8089 3.4256 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9595 2.9352 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9595 1.9544 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9595 -0.9879 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8089 1.4641 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8089 -1.4782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8225 0.5342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1102 -1.4782 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4114 0.4833 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2608 -0.0071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8739 0.4453 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.5077 4.4064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7127 -1.4782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6583 -2.9494 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5938 2.0478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8089 4.4064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1102 3.4256 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1102 1.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8089 0.4833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6583 1.9544 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 31 1 0 0 0 0 2 31 1 0 0 0 0 3 32 1 0 0 0 0 4 32 1 0 0 0 0 6 34 1 0 0 0 0 9 13 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 24 1 0 0 0 0 12 33 1 0 0 0 0 13 34 1 0 0 0 0 14 36 1 0 0 0 0 15 19 1 0 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 16 35 1 0 0 0 0 17 37 1 0 0 0 0 18 9 1 1 0 0 0 18 25 1 0 0 0 0 18 36 1 0 0 0 0 19 25 1 0 0 0 0 19 38 1 1 0 0 0 20 29 1 0 0 0 0 20 44 1 6 0 0 0 21 17 1 1 0 0 0 21 26 1 0 0 0 0 21 45 1 0 0 0 0 22 33 1 1 0 0 0 22 35 1 0 0 0 0 23 31 1 0 0 0 0 23 39 1 1 0 0 0 24 32 1 0 0 0 0 24 40 1 6 0 0 0 25 34 1 6 0 0 0 26 27 1 0 0 0 0 26 41 1 6 0 0 0 27 28 1 0 0 0 0 27 42 1 1 0 0 0 28 30 1 0 0 0 0 28 43 1 6 0 0 0 29 31 1 0 0 0 0 29 33 1 1 0 0 0 30 44 1 1 0 0 0 30 45 1 0 0 0 0 32 46 1 0 0 0 0 33 5 1 1 0 0 0 34 35 1 1 0 0 0 35 7 1 1 0 0 0 36 8 1 6 0 0 0 36 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	654.43
Volume:	667.775
LogP:	3.217
LogD:	3.703
LogS:	-3.424
# Rotatable Bonds:	4
TPSA:	169.3
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.224
Synthetic Accessibility Score:	5.616
Fsp3:	1.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.227
MDCK Permeability:	3.196476973243989e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.405
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	70.08618927001953%
Volume Distribution (VD):	0.469
Pgp-substrate:	9.81499195098877%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.723
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.07
CYP3A4-substrate:	0.18

ADMET: Excretion

Clearance (CL):	1.622
Half-life (T1/2):	0.534

ADMET: Toxicity

hERG Blockers:	0.158
Human Hepatotoxicity (H-HT):	0.292
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.581
Maximum Recommended Daily Dose:	0.683
Skin Sensitization:	0.345
Carcinogencity:	0.01
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC131466

Natural Product ID:	NPC131466
*Common Name:**	Ginsenoside R10
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[[(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-17-[(2S,5R)-5-hydroxy-2,6,6-trimethyloxan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	Ginsenoside R10
Standard InCHIKey:	CFOKFXFKMQABRM-JLXGCTMESA-N
Standard InCHI:	InChI=1S/C36H62O10/c1-31(2)23(39)10-12-33(5)22-15-19(38)25-18(36(8)14-11-24(40)32(3,4)46-36)9-13-34(25,6)35(22,7)16-20(29(31)33)44-30-28(43)27(42)26(41)21(17-37)45-30/h18-30,37-43H,9-17H2,1-8H3/t18-,19+,20-,21+,22+,23-,24+,25-,26+,27-,28+,29-,30+,33+,34+,35+,36-/m0/s1
SMILES:	CC1(C)[C@H](CC[C@]2(C)[C@H]3C[C@H]([C@@H]4[C@H](CC[C@@]4(C)[C@]3(C)C[C@@H]([C@@H]12)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)[C@]1(C)CC[C@H](C(C)(C)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509099
PubChem CID:	44584745
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO25128	Panax vietnamensis	Species	Araliaceae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[11325227]
NPO25128	Panax vietnamensis	Species	Araliaceae	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	9

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT993	Cell Line	Hepatocyte	Mus musculus	Survival	=	41.1	%	PMID[484339]
NPT993	Cell Line	Hepatocyte	Mus musculus	Survival	=	35.2	%	PMID[484339]
NPT993	Cell Line	Hepatocyte	Mus musculus	Survival	=	38.3	%	PMID[484339]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	37.6	%	PMID[484339]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	17.8	%	PMID[484339]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	28.0	%	PMID[484339]
NPT993	Cell Line	Hepatocyte	Mus musculus	Activity	=	16.0	%	PMID[484339]
NPT993	Cell Line	Hepatocyte	Mus musculus	Activity	=	7.6	%	PMID[484339]
NPT993	Cell Line	Hepatocyte	Mus musculus	Activity	=	12.0	%	PMID[484339]

☑ 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 NPC131466 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	538
0.1-0.2	4879
0.2-0.3	13087
0.3-0.4	11102
0.4-0.5	5434
0.5-0.6	3705
0.6-0.7	2110
0.7-0.8	1321
0.8-0.85	222
0.85-0.9	146
0.9-0.95	123
0.95-1	30

Similarity Score	Similarity Level	Natural Product ID
0.9765	High Similarity	NPC229801
0.9765	High Similarity	NPC307167
0.9765	High Similarity	NPC210759
0.9759	High Similarity	NPC140446
0.9759	High Similarity	NPC43912
0.9647	High Similarity	NPC65550
0.954	High Similarity	NPC45959
0.954	High Similarity	NPC305418
0.954	High Similarity	NPC309866
0.954	High Similarity	NPC252253
0.9535	High Similarity	NPC204881
0.9535	High Similarity	NPC473830
0.9529	High Similarity	NPC82955
0.9518	High Similarity	NPC290612
0.9432	High Similarity	NPC57964
0.9432	High Similarity	NPC92196
0.9432	High Similarity	NPC94582
0.9432	High Similarity	NPC477494
0.9425	High Similarity	NPC137004
0.9425	High Similarity	NPC149400
0.9425	High Similarity	NPC88962
0.9425	High Similarity	NPC473726
0.9425	High Similarity	NPC144790
0.9425	High Similarity	NPC172838
0.9419	High Similarity	NPC279329
0.9412	High Similarity	NPC281004
0.9326	High Similarity	NPC142264
0.9326	High Similarity	NPC139271
0.9326	High Similarity	NPC238796
0.9326	High Similarity	NPC237071
0.9326	High Similarity	NPC304011
0.9326	High Similarity	NPC476510
0.9326	High Similarity	NPC203434
0.9318	High Similarity	NPC253268
0.9318	High Similarity	NPC179859
0.9318	High Similarity	NPC473851
0.9318	High Similarity	NPC174024
0.9318	High Similarity	NPC291547
0.9318	High Similarity	NPC312678
0.9318	High Similarity	NPC475436
0.9318	High Similarity	NPC131693
0.9318	High Similarity	NPC473774
0.9318	High Similarity	NPC24960
0.931	High Similarity	NPC293609
0.931	High Similarity	NPC36372
0.9302	High Similarity	NPC102725
0.9302	High Similarity	NPC473472
0.9222	High Similarity	NPC233649
0.9222	High Similarity	NPC477222
0.9222	High Similarity	NPC477223
0.9222	High Similarity	NPC470028
0.9213	High Similarity	NPC474399
0.9205	High Similarity	NPC311246
0.9205	High Similarity	NPC177834
0.9205	High Similarity	NPC250393
0.9205	High Similarity	NPC141769
0.9205	High Similarity	NPC477451
0.9205	High Similarity	NPC297348
0.9205	High Similarity	NPC234352
0.9205	High Similarity	NPC325828
0.9205	High Similarity	NPC48339
0.9205	High Similarity	NPC277774
0.9205	High Similarity	NPC167644
0.9205	High Similarity	NPC249204
0.9205	High Similarity	NPC477547
0.9195	High Similarity	NPC223143
0.9195	High Similarity	NPC473542
0.9111	High Similarity	NPC121453
0.9111	High Similarity	NPC296936
0.9101	High Similarity	NPC151214
0.9101	High Similarity	NPC217205
0.9101	High Similarity	NPC473503
0.9101	High Similarity	NPC222731
0.9101	High Similarity	NPC3538
0.9101	High Similarity	NPC191915
0.9101	High Similarity	NPC264101
0.9101	High Similarity	NPC113500
0.9101	High Similarity	NPC477224
0.9101	High Similarity	NPC175
0.9101	High Similarity	NPC291203
0.9101	High Similarity	NPC471464
0.9101	High Similarity	NPC294686
0.9091	High Similarity	NPC5632
0.9091	High Similarity	NPC149966
0.9091	High Similarity	NPC476668
0.9091	High Similarity	NPC473637
0.9011	High Similarity	NPC476112
0.9011	High Similarity	NPC470591
0.9011	High Similarity	NPC274200
0.9011	High Similarity	NPC307534
0.9011	High Similarity	NPC475207
0.9	High Similarity	NPC469710
0.9	High Similarity	NPC475351
0.9	High Similarity	NPC206003
0.9	High Similarity	NPC211354
0.9	High Similarity	NPC107962
0.9	High Similarity	NPC107188
0.9	High Similarity	NPC473727
0.9	High Similarity	NPC19400
0.9	High Similarity	NPC473610
0.9	High Similarity	NPC473067
0.9	High Similarity	NPC473065
0.9	High Similarity	NPC473064
0.9	High Similarity	NPC6295
0.8989	High Similarity	NPC476669
0.8989	High Similarity	NPC171741
0.8989	High Similarity	NPC224003
0.8989	High Similarity	NPC18724
0.8989	High Similarity	NPC470623
0.8989	High Similarity	NPC323231
0.8925	High Similarity	NPC476839
0.8925	High Similarity	NPC472081
0.8925	High Similarity	NPC476838
0.8925	High Similarity	NPC108227
0.8925	High Similarity	NPC475574
0.8925	High Similarity	NPC476512
0.8913	High Similarity	NPC473616
0.8913	High Similarity	NPC473518
0.8901	High Similarity	NPC103616
0.8901	High Similarity	NPC284104
0.8901	High Similarity	NPC287483
0.8901	High Similarity	NPC30856
0.8901	High Similarity	NPC184617
0.8901	High Similarity	NPC252056
0.8901	High Similarity	NPC475643
0.8901	High Similarity	NPC128572
0.8901	High Similarity	NPC84111
0.8901	High Similarity	NPC116756
0.8901	High Similarity	NPC195297
0.8901	High Similarity	NPC132080
0.8901	High Similarity	NPC232037
0.8901	High Similarity	NPC470865
0.8901	High Similarity	NPC97700
0.8901	High Similarity	NPC475625
0.8901	High Similarity	NPC470866
0.8901	High Similarity	NPC98018
0.8901	High Similarity	NPC160426
0.8901	High Similarity	NPC470864
0.8901	High Similarity	NPC472989
0.8901	High Similarity	NPC470863
0.8901	High Similarity	NPC473601
0.8901	High Similarity	NPC473287
0.8889	High Similarity	NPC267238
0.8889	High Similarity	NPC253611
0.8889	High Similarity	NPC148593
0.8889	High Similarity	NPC475325
0.8889	High Similarity	NPC77717
0.8889	High Similarity	NPC471373
0.8864	High Similarity	NPC20822
0.883	High Similarity	NPC310138
0.883	High Similarity	NPC114700
0.883	High Similarity	NPC470029
0.883	High Similarity	NPC134967
0.8804	High Similarity	NPC470861
0.8804	High Similarity	NPC51520
0.8804	High Similarity	NPC303069
0.8804	High Similarity	NPC470862
0.8804	High Similarity	NPC232611
0.8804	High Similarity	NPC210157
0.8804	High Similarity	NPC115165
0.8804	High Similarity	NPC83137
0.8791	High Similarity	NPC205129
0.8791	High Similarity	NPC106701
0.8791	High Similarity	NPC471425
0.8791	High Similarity	NPC189575
0.8791	High Similarity	NPC471429
0.8791	High Similarity	NPC471424
0.8737	High Similarity	NPC139181
0.8737	High Similarity	NPC211879
0.8737	High Similarity	NPC131479
0.8737	High Similarity	NPC472252
0.8737	High Similarity	NPC189852
0.8737	High Similarity	NPC31907
0.8737	High Similarity	NPC114874
0.8737	High Similarity	NPC245280
0.8737	High Similarity	NPC97260
0.8737	High Similarity	NPC286969
0.8737	High Similarity	NPC16520
0.8737	High Similarity	NPC473020
0.8737	High Similarity	NPC155010
0.8737	High Similarity	NPC157659
0.8737	High Similarity	NPC8039
0.8737	High Similarity	NPC476837
0.8737	High Similarity	NPC120123
0.8723	High Similarity	NPC477172
0.871	High Similarity	NPC291548
0.871	High Similarity	NPC473638
0.8681	High Similarity	NPC30687
0.8675	High Similarity	NPC177343
0.8667	High Similarity	NPC59006
0.8646	High Similarity	NPC475521
0.8646	High Similarity	NPC476360
0.8646	High Similarity	NPC476361
0.8646	High Similarity	NPC165033
0.8646	High Similarity	NPC273879
0.8636	High Similarity	NPC472396
0.8632	High Similarity	NPC159036
0.8632	High Similarity	NPC312553
0.8632	High Similarity	NPC288694
0.8617	High Similarity	NPC20028

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 NPC131466 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	533
0.1-0.2	4518
0.2-0.3	2854
0.3-0.4	660
0.4-0.5	312
0.5-0.6	211
0.6-0.7	44
0.7-0.8	16
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9205	High Similarity	NPD8171	Discontinued
0.8265	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD6928	Phase 2
0.7711	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD8133	Approved
0.7558	Intermediate Similarity	NPD1810	Approved
0.7558	Intermediate Similarity	NPD1811	Approved
0.7545	Intermediate Similarity	NPD8294	Approved
0.7545	Intermediate Similarity	NPD8377	Approved
0.7477	Intermediate Similarity	NPD8033	Approved
0.7477	Intermediate Similarity	NPD8296	Approved
0.7477	Intermediate Similarity	NPD8380	Approved
0.7477	Intermediate Similarity	NPD8379	Approved
0.7477	Intermediate Similarity	NPD8335	Approved
0.7477	Intermediate Similarity	NPD8378	Approved
0.7209	Intermediate Similarity	NPD2687	Approved
0.7209	Intermediate Similarity	NPD2686	Approved
0.7209	Intermediate Similarity	NPD2254	Approved
0.7207	Intermediate Similarity	NPD7328	Approved
0.7207	Intermediate Similarity	NPD7327	Approved
0.7143	Intermediate Similarity	NPD7516	Approved
0.7103	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7991	Discontinued
0.7021	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3669	Approved
0.6964	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6940	Discontinued
0.687	Remote Similarity	NPD7503	Approved
0.6852	Remote Similarity	NPD8174	Phase 2
0.6848	Remote Similarity	NPD6114	Approved
0.6848	Remote Similarity	NPD6118	Approved
0.6848	Remote Similarity	NPD6697	Approved
0.6848	Remote Similarity	NPD6115	Approved
0.6818	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7507	Approved
0.6759	Remote Similarity	NPD6412	Phase 2
0.6739	Remote Similarity	NPD6116	Phase 1
0.6706	Remote Similarity	NPD371	Approved
0.663	Remote Similarity	NPD6117	Approved
0.6629	Remote Similarity	NPD4787	Phase 1
0.6612	Remote Similarity	NPD7319	Approved
0.661	Remote Similarity	NPD8328	Phase 3
0.6526	Remote Similarity	NPD7525	Registered
0.6413	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7736	Approved
0.6374	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD3703	Phase 2
0.632	Remote Similarity	NPD8449	Approved
0.6311	Remote Similarity	NPD8034	Phase 2
0.6311	Remote Similarity	NPD8035	Phase 2
0.6289	Remote Similarity	NPD1780	Approved
0.6289	Remote Similarity	NPD1779	Approved
0.627	Remote Similarity	NPD8450	Suspended
0.625	Remote Similarity	NPD6686	Approved
0.625	Remote Similarity	NPD6370	Approved
0.6179	Remote Similarity	NPD8293	Discontinued
0.6163	Remote Similarity	NPD6123	Approved
0.6154	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD6059	Approved
0.6083	Remote Similarity	NPD6054	Approved
0.6082	Remote Similarity	NPD7645	Phase 2
0.6078	Remote Similarity	NPD7524	Approved
0.6044	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD5360	Phase 3
0.604	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3702	Approved
0.598	Remote Similarity	NPD8308	Discontinued
0.5965	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD7638	Approved
0.5956	Remote Similarity	NPD7625	Phase 1
0.5941	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD4244	Approved
0.5914	Remote Similarity	NPD4245	Approved
0.5914	Remote Similarity	NPD4789	Approved
0.5909	Remote Similarity	NPD7639	Approved
0.5909	Remote Similarity	NPD7640	Approved
0.5905	Remote Similarity	NPD6700	Approved
0.5905	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD892	Phase 3
0.5904	Remote Similarity	NPD893	Approved
0.5904	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD891	Phase 3
0.5904	Remote Similarity	NPD888	Phase 3
0.5902	Remote Similarity	NPD6015	Approved
0.5902	Remote Similarity	NPD8516	Approved
0.5902	Remote Similarity	NPD8517	Approved
0.5902	Remote Similarity	NPD8515	Approved
0.5902	Remote Similarity	NPD8513	Phase 3
0.5902	Remote Similarity	NPD6016	Approved
0.5897	Remote Similarity	NPD6882	Approved
0.5897	Remote Similarity	NPD8297	Approved
0.5887	Remote Similarity	NPD7492	Approved
0.5854	Remote Similarity	NPD5988	Approved
0.5849	Remote Similarity	NPD6702	Approved
0.5849	Remote Similarity	NPD6703	Approved
0.5842	Remote Similarity	NPD6695	Phase 3
0.584	Remote Similarity	NPD6616	Approved
0.5833	Remote Similarity	NPD6009	Approved
0.582	Remote Similarity	NPD6319	Approved
0.5806	Remote Similarity	NPD6067	Discontinued
0.5806	Remote Similarity	NPD3698	Phase 2
0.5804	Remote Similarity	NPD7632	Discontinued
0.5794	Remote Similarity	NPD7078	Approved
0.5783	Remote Similarity	NPD2269	Approved
0.5776	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7750	Discontinued
0.5766	Remote Similarity	NPD8418	Phase 2
0.5714	Remote Similarity	NPD889	Approved
0.5714	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1700	Approved
0.5714	Remote Similarity	NPD4632	Approved
0.5714	Remote Similarity	NPD894	Approved
0.5714	Remote Similarity	NPD887	Approved
0.5714	Remote Similarity	NPD895	Approved
0.5702	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD2267	Suspended
0.5684	Remote Similarity	NPD5777	Approved
0.5684	Remote Similarity	NPD4758	Discontinued
0.5684	Remote Similarity	NPD6081	Approved
0.567	Remote Similarity	NPD6942	Approved
0.567	Remote Similarity	NPD7339	Approved
0.5664	Remote Similarity	NPD8085	Approved
0.5664	Remote Similarity	NPD8139	Approved
0.5664	Remote Similarity	NPD8084	Approved
0.5664	Remote Similarity	NPD8083	Approved
0.5664	Remote Similarity	NPD8138	Approved
0.5664	Remote Similarity	NPD8086	Approved
0.5664	Remote Similarity	NPD8082	Approved
0.5663	Remote Similarity	NPD905	Approved
0.5663	Remote Similarity	NPD904	Phase 3
0.5657	Remote Similarity	NPD5364	Discontinued
0.5657	Remote Similarity	NPD3671	Phase 1
0.5652	Remote Similarity	NPD7128	Approved
0.5652	Remote Similarity	NPD6675	Approved
0.5652	Remote Similarity	NPD5739	Approved
0.5652	Remote Similarity	NPD6402	Approved
0.5647	Remote Similarity	NPD7346	Approved
0.5641	Remote Similarity	NPD6372	Approved
0.5641	Remote Similarity	NPD6373	Approved
0.5625	Remote Similarity	NPD6033	Approved
0.5614	Remote Similarity	NPD8276	Approved
0.5614	Remote Similarity	NPD8275	Approved
0.5612	Remote Similarity	NPD6933	Approved
0.5603	Remote Similarity	NPD7646	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