NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	484.3
Volume:	491.712
LogP:	1.722
LogD:	2.094
LogS:	-2.757
# Rotatable Bonds:	5
TPSA:	139.84
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.252
Synthetic Accessibility Score:	5.055
Fsp3:	0.923
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.16
MDCK Permeability:	4.598803570843302e-05
Pgp-inhibitor:	0.978
Pgp-substrate:	0.107
Human Intestinal Absorption (HIA):	0.842
20% Bioavailability (F20%):	0.196
30% Bioavailability (F30%):	0.199

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.148
Plasma Protein Binding (PPB):	56.44536209106445%
Volume Distribution (VD):	0.543
Pgp-substrate:	24.636268615722656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.097
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.566
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.097
CYP3A4-substrate:	0.121

ADMET: Excretion

Clearance (CL):	2.597
Half-life (T1/2):	0.736

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.232
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.135
Rat Oral Acute Toxicity:	0.516
Maximum Recommended Daily Dose:	0.761
Skin Sensitization:	0.098
Carcinogencity:	0.217
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC477927

Natural Product ID:	NPC477927
*Common Name:**	(2R,3R,4S,5S,6R)-2-[[(2R,4aS,4bR,7S,10aS)-7-(1,2-dihydroxyethyl)-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthren-2-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[[(2R,4aS,4bR,7S,10aS)-7-(1,2-dihydroxyethyl)-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthren-2-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	QWWPCQGHWWNGET-AWZIAUHPSA-N
Standard InCHI:	InChI=1S/C26H44O8/c1-24(2)17-6-5-14-11-25(3,18(29)13-28)9-7-15(14)26(17,4)10-8-19(24)34-23-22(32)21(31)20(30)16(12-27)33-23/h11,15-23,27-32H,5-10,12-13H2,1-4H3/t15-,16-,17-,18?,19-,20-,21+,22-,23+,25+,26+/m1/s1
SMILES:	C[C@@]1(CC[C@@H]2C(=C1)CC[C@H]3[C@]2(CC[C@H](C3(C)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C)C(CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11785008
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19928884]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	aerial part	n.a.	n.a.	PMID[24997688]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Others	2

Activity Type	# Activity
Others	4

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	5.86	%	PMID[24997688]
NPT2	Others	Unspecified	IC50	>	10	ug/ml	PMID[24997688]
NPT2	Others	Unspecified	Inhibition	=	5.93	%	PMID[24997688]

☑ 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 NPC477927 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	237
0.1-0.2	1776
0.2-0.3	5179
0.3-0.4	12216
0.4-0.5	10803
0.5-0.6	5764
0.6-0.7	4186
0.7-0.8	2007
0.8-0.85	440
0.85-0.9	77
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC72817
0.956	High Similarity	NPC477928
0.9551	High Similarity	NPC305160
0.9451	High Similarity	NPC240372
0.9247	High Similarity	NPC64348
0.9158	High Similarity	NPC473129
0.9158	High Similarity	NPC99627
0.9149	High Similarity	NPC263756
0.9149	High Similarity	NPC117714
0.913	High Similarity	NPC90583
0.9062	High Similarity	NPC187400
0.9062	High Similarity	NPC470885
0.9062	High Similarity	NPC109792
0.9062	High Similarity	NPC57065
0.9062	High Similarity	NPC54521
0.9062	High Similarity	NPC75608
0.9062	High Similarity	NPC221562
0.9053	High Similarity	NPC213674
0.9053	High Similarity	NPC76497
0.9053	High Similarity	NPC136816
0.9053	High Similarity	NPC30289
0.9053	High Similarity	NPC256133
0.9043	High Similarity	NPC473200
0.9043	High Similarity	NPC7341
0.9032	High Similarity	NPC473890
0.9032	High Similarity	NPC243728
0.8969	High Similarity	NPC242748
0.8958	High Similarity	NPC162354
0.8958	High Similarity	NPC473123
0.8958	High Similarity	NPC473124
0.8958	High Similarity	NPC473198
0.8958	High Similarity	NPC123796
0.8947	High Similarity	NPC88000
0.8947	High Similarity	NPC4831
0.8947	High Similarity	NPC309425
0.8947	High Similarity	NPC129372
0.8947	High Similarity	NPC472023
0.8947	High Similarity	NPC160734
0.8947	High Similarity	NPC47566
0.8936	High Similarity	NPC234287
0.8936	High Similarity	NPC158088
0.8936	High Similarity	NPC280825
0.8925	High Similarity	NPC207617
0.8913	High Similarity	NPC211238
0.8878	High Similarity	NPC257964
0.8878	High Similarity	NPC78034
0.8878	High Similarity	NPC190395
0.8866	High Similarity	NPC148603
0.8866	High Similarity	NPC203354
0.8866	High Similarity	NPC471434
0.8866	High Similarity	NPC473127
0.8866	High Similarity	NPC93352
0.8866	High Similarity	NPC470768
0.8866	High Similarity	NPC110656
0.8866	High Similarity	NPC471435
0.8866	High Similarity	NPC230948
0.8866	High Similarity	NPC473734
0.8866	High Similarity	NPC173583
0.8854	High Similarity	NPC312553
0.8854	High Similarity	NPC288694
0.8854	High Similarity	NPC272015
0.8854	High Similarity	NPC159036
0.8842	High Similarity	NPC473790
0.8842	High Similarity	NPC282669
0.8791	High Similarity	NPC159876
0.8788	High Similarity	NPC126147
0.8776	High Similarity	NPC470767
0.8776	High Similarity	NPC472898
0.8776	High Similarity	NPC138057
0.8776	High Similarity	NPC470763
0.8776	High Similarity	NPC472900
0.8776	High Similarity	NPC472899
0.8776	High Similarity	NPC473476
0.8776	High Similarity	NPC473923
0.8776	High Similarity	NPC173859
0.8776	High Similarity	NPC470512
0.8776	High Similarity	NPC309448
0.8763	High Similarity	NPC131479
0.8763	High Similarity	NPC157659
0.8763	High Similarity	NPC245280
0.8763	High Similarity	NPC189852
0.8763	High Similarity	NPC286969
0.8763	High Similarity	NPC213190
0.8763	High Similarity	NPC114874
0.8763	High Similarity	NPC31907
0.8763	High Similarity	NPC155010
0.8763	High Similarity	NPC472252
0.8763	High Similarity	NPC16520
0.8763	High Similarity	NPC8039
0.8763	High Similarity	NPC211879
0.8763	High Similarity	NPC120123
0.8763	High Similarity	NPC16573
0.8763	High Similarity	NPC473020
0.875	High Similarity	NPC470434
0.875	High Similarity	NPC267510
0.8737	High Similarity	NPC5358
0.8737	High Similarity	NPC216260
0.871	High Similarity	NPC178949
0.871	High Similarity	NPC96736
0.87	High Similarity	NPC302057
0.8696	High Similarity	NPC302584
0.8687	High Similarity	NPC226642
0.8687	High Similarity	NPC33053
0.8687	High Similarity	NPC473469
0.8687	High Similarity	NPC281939
0.8681	High Similarity	NPC473058
0.8673	High Similarity	NPC165033
0.8673	High Similarity	NPC273879
0.866	High Similarity	NPC154452
0.8646	High Similarity	NPC469942
0.8632	High Similarity	NPC76486
0.8621	High Similarity	NPC16090
0.8614	High Similarity	NPC274507
0.8602	High Similarity	NPC474792
0.8602	High Similarity	NPC91654
0.8602	High Similarity	NPC67398
0.86	High Similarity	NPC7213
0.86	High Similarity	NPC476538
0.86	High Similarity	NPC476539
0.86	High Similarity	NPC476540
0.86	High Similarity	NPC476541
0.8586	High Similarity	NPC208594
0.8586	High Similarity	NPC152584
0.8586	High Similarity	NPC69737
0.8586	High Similarity	NPC473199
0.8586	High Similarity	NPC474569
0.8586	High Similarity	NPC160816
0.8586	High Similarity	NPC269627
0.8586	High Similarity	NPC181845
0.8586	High Similarity	NPC208477
0.8586	High Similarity	NPC127801
0.8586	High Similarity	NPC26798
0.8586	High Similarity	NPC194842
0.8571	High Similarity	NPC475701
0.8557	High Similarity	NPC21064
0.8557	High Similarity	NPC121072
0.8539	High Similarity	NPC166279
0.8539	High Similarity	NPC319238
0.8529	High Similarity	NPC211798
0.8529	High Similarity	NPC114188
0.8529	High Similarity	NPC191763
0.8529	High Similarity	NPC297208
0.8529	High Similarity	NPC197231
0.8529	High Similarity	NPC473481
0.8529	High Similarity	NPC235841
0.8529	High Similarity	NPC30397
0.8529	High Similarity	NPC108748
0.8526	High Similarity	NPC472989
0.8515	High Similarity	NPC157530
0.8515	High Similarity	NPC250089
0.8515	High Similarity	NPC137917
0.8515	High Similarity	NPC167383
0.8515	High Similarity	NPC477027
0.8515	High Similarity	NPC57362
0.8515	High Similarity	NPC306131
0.8515	High Similarity	NPC204407
0.8515	High Similarity	NPC14630
0.8515	High Similarity	NPC70204
0.8515	High Similarity	NPC237503
0.8515	High Similarity	NPC475670
0.8515	High Similarity	NPC472901
0.8515	High Similarity	NPC306746
0.8515	High Similarity	NPC477026
0.85	High Similarity	NPC305423
0.85	High Similarity	NPC283829
0.85	High Similarity	NPC293512
0.85	High Similarity	NPC113044
0.85	High Similarity	NPC63368
0.85	High Similarity	NPC181467
0.85	High Similarity	NPC94272
0.85	High Similarity	NPC14704
0.85	High Similarity	NPC230507
0.85	High Similarity	NPC161676
0.85	High Similarity	NPC234160
0.85	High Similarity	NPC14946
0.85	High Similarity	NPC208650
0.85	High Similarity	NPC470432
0.85	High Similarity	NPC231340
0.8485	Intermediate Similarity	NPC474464
0.8485	Intermediate Similarity	NPC475365
0.8485	Intermediate Similarity	NPC312774
0.8478	Intermediate Similarity	NPC477917
0.8454	Intermediate Similarity	NPC324598
0.8454	Intermediate Similarity	NPC91497
0.8447	Intermediate Similarity	NPC116794
0.8447	Intermediate Similarity	NPC19888
0.8447	Intermediate Similarity	NPC46388
0.8447	Intermediate Similarity	NPC37739
0.8447	Intermediate Similarity	NPC128925
0.8447	Intermediate Similarity	NPC256798
0.8431	Intermediate Similarity	NPC279554
0.8431	Intermediate Similarity	NPC476881
0.8431	Intermediate Similarity	NPC191439
0.8431	Intermediate Similarity	NPC170974
0.8431	Intermediate Similarity	NPC59804
0.8431	Intermediate Similarity	NPC476886
0.8431	Intermediate Similarity	NPC475296
0.8431	Intermediate Similarity	NPC90856
0.8431	Intermediate Similarity	NPC476887
0.8431	Intermediate Similarity	NPC7870

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 NPC477927 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	2019
0.2-0.3	3970
0.3-0.4	1949
0.4-0.5	607
0.5-0.6	249
0.6-0.7	130
0.7-0.8	18
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7981	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD6412	Phase 2
0.7727	Intermediate Similarity	NPD7328	Approved
0.7727	Intermediate Similarity	NPD7327	Approved
0.7714	Intermediate Similarity	NPD6686	Approved
0.7679	Intermediate Similarity	NPD8033	Approved
0.7658	Intermediate Similarity	NPD7516	Approved
0.7636	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD8377	Approved
0.7589	Intermediate Similarity	NPD8294	Approved
0.7582	Intermediate Similarity	NPD7645	Phase 2
0.7544	Intermediate Similarity	NPD8328	Phase 3
0.7522	Intermediate Similarity	NPD8379	Approved
0.7522	Intermediate Similarity	NPD7503	Approved
0.7522	Intermediate Similarity	NPD8378	Approved
0.7522	Intermediate Similarity	NPD8380	Approved
0.7522	Intermediate Similarity	NPD8296	Approved
0.7522	Intermediate Similarity	NPD8335	Approved
0.7265	Intermediate Similarity	NPD7507	Approved
0.7207	Intermediate Similarity	NPD8133	Approved
0.7143	Intermediate Similarity	NPD7524	Approved
0.7129	Intermediate Similarity	NPD8171	Discontinued
0.7128	Intermediate Similarity	NPD7525	Registered
0.7083	Intermediate Similarity	NPD7319	Approved
0.701	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6370	Approved
0.6957	Remote Similarity	NPD6942	Approved
0.6957	Remote Similarity	NPD7339	Approved
0.6931	Remote Similarity	NPD3168	Discontinued
0.6911	Remote Similarity	NPD8449	Approved
0.6907	Remote Similarity	NPD6695	Phase 3
0.6882	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7736	Approved
0.6855	Remote Similarity	NPD8450	Suspended
0.6838	Remote Similarity	NPD6054	Approved
0.6838	Remote Similarity	NPD6059	Approved
0.6807	Remote Similarity	NPD6067	Discontinued
0.6792	Remote Similarity	NPD4225	Approved
0.6792	Remote Similarity	NPD7638	Approved
0.678	Remote Similarity	NPD8517	Approved
0.678	Remote Similarity	NPD8516	Approved
0.678	Remote Similarity	NPD8513	Phase 3
0.678	Remote Similarity	NPD8515	Approved
0.6777	Remote Similarity	NPD8293	Discontinued
0.6731	Remote Similarity	NPD7748	Approved
0.6729	Remote Similarity	NPD7640	Approved
0.6729	Remote Similarity	NPD7639	Approved
0.6702	Remote Similarity	NPD6933	Approved
0.6699	Remote Similarity	NPD7515	Phase 2
0.6698	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD1810	Approved
0.6667	Remote Similarity	NPD1811	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD6929	Approved
0.6667	Remote Similarity	NPD5344	Discontinued
0.6639	Remote Similarity	NPD6015	Approved
0.6639	Remote Similarity	NPD6016	Approved
0.6635	Remote Similarity	NPD6399	Phase 3
0.6634	Remote Similarity	NPD7750	Discontinued
0.6612	Remote Similarity	NPD7492	Approved
0.6598	Remote Similarity	NPD6931	Approved
0.6598	Remote Similarity	NPD6930	Phase 2
0.6598	Remote Similarity	NPD6928	Phase 2
0.6583	Remote Similarity	NPD5988	Approved
0.6581	Remote Similarity	NPD6009	Approved
0.6557	Remote Similarity	NPD6616	Approved
0.6555	Remote Similarity	NPD6319	Approved
0.6549	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6411	Approved
0.6522	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8297	Approved
0.6504	Remote Similarity	NPD7078	Approved
0.65	Remote Similarity	NPD4786	Approved
0.6489	Remote Similarity	NPD6924	Approved
0.6489	Remote Similarity	NPD6926	Approved
0.6486	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD4632	Approved
0.6465	Remote Similarity	NPD3667	Approved
0.646	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6932	Approved
0.6458	Remote Similarity	NPD5776	Phase 2
0.6458	Remote Similarity	NPD6925	Approved
0.6442	Remote Similarity	NPD6698	Approved
0.6442	Remote Similarity	NPD46	Approved
0.6441	Remote Similarity	NPD7115	Discovery
0.6435	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5357	Phase 1
0.6429	Remote Similarity	NPD6402	Approved
0.6429	Remote Similarity	NPD6675	Approved
0.6429	Remote Similarity	NPD7509	Discontinued
0.6429	Remote Similarity	NPD5739	Approved
0.6429	Remote Similarity	NPD7128	Approved
0.6421	Remote Similarity	NPD8264	Approved
0.6415	Remote Similarity	NPD7900	Approved
0.6415	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6373	Approved
0.6404	Remote Similarity	NPD6372	Approved
0.6392	Remote Similarity	NPD7145	Approved
0.6381	Remote Similarity	NPD7087	Discontinued
0.6373	Remote Similarity	NPD3618	Phase 1
0.6348	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6101	Approved
0.6346	Remote Similarity	NPD5328	Approved
0.6344	Remote Similarity	NPD2687	Approved
0.6344	Remote Similarity	NPD2254	Approved
0.6344	Remote Similarity	NPD2686	Approved
0.6337	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.633	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6683	Phase 2
0.632	Remote Similarity	NPD6033	Approved
0.6316	Remote Similarity	NPD7320	Approved
0.6316	Remote Similarity	NPD6899	Approved
0.6316	Remote Similarity	NPD6881	Approved
0.6293	Remote Similarity	NPD6649	Approved
0.6293	Remote Similarity	NPD6650	Approved
0.6286	Remote Similarity	NPD7838	Discovery
0.6277	Remote Similarity	NPD7152	Approved
0.6277	Remote Similarity	NPD7150	Approved
0.6277	Remote Similarity	NPD7151	Approved
0.6275	Remote Similarity	NPD6893	Approved
0.6273	Remote Similarity	NPD6648	Approved
0.6263	Remote Similarity	NPD7332	Phase 2
0.6263	Remote Similarity	NPD7514	Phase 3
0.6239	Remote Similarity	NPD6430	Approved
0.6239	Remote Similarity	NPD6429	Approved
0.6239	Remote Similarity	NPD4755	Approved
0.6238	Remote Similarity	NPD3669	Approved
0.6238	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6922	Approved
0.6237	Remote Similarity	NPD6923	Approved
0.6228	Remote Similarity	NPD5701	Approved
0.6228	Remote Similarity	NPD5697	Approved
0.6226	Remote Similarity	NPD6079	Approved
0.6226	Remote Similarity	NPD8034	Phase 2
0.6226	Remote Similarity	NPD7637	Suspended
0.6226	Remote Similarity	NPD8035	Phase 2
0.6216	Remote Similarity	NPD4159	Approved
0.6207	Remote Similarity	NPD7290	Approved
0.6207	Remote Similarity	NPD6883	Approved
0.6207	Remote Similarity	NPD4634	Approved
0.6207	Remote Similarity	NPD7102	Approved
0.62	Remote Similarity	NPD6898	Phase 1
0.62	Remote Similarity	NPD6902	Approved
0.617	Remote Similarity	NPD7143	Approved
0.617	Remote Similarity	NPD7144	Approved
0.6168	Remote Similarity	NPD5779	Approved
0.6168	Remote Similarity	NPD5778	Approved
0.6168	Remote Similarity	NPD4202	Approved
0.6161	Remote Similarity	NPD7632	Discontinued
0.6154	Remote Similarity	NPD8130	Phase 1
0.6154	Remote Similarity	NPD6869	Approved
0.6154	Remote Similarity	NPD6617	Approved
0.6154	Remote Similarity	NPD6847	Approved
0.6146	Remote Similarity	NPD4785	Approved
0.6146	Remote Similarity	NPD4784	Approved
0.614	Remote Similarity	NPD6008	Approved
0.6131	Remote Similarity	NPD7625	Phase 1
0.6129	Remote Similarity	NPD7604	Phase 2
0.6126	Remote Similarity	NPD4696	Approved
0.6126	Remote Similarity	NPD5285	Approved
0.6126	Remote Similarity	NPD4700	Approved
0.6126	Remote Similarity	NPD5286	Approved
0.6121	Remote Similarity	NPD6014	Approved
0.6121	Remote Similarity	NPD6012	Approved
0.6121	Remote Similarity	NPD6013	Approved
0.6117	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD8074	Phase 3
0.6105	Remote Similarity	NPD4243	Approved
0.61	Remote Similarity	NPD4748	Discontinued
0.6098	Remote Similarity	NPD5983	Phase 2
0.6091	Remote Similarity	NPD6084	Phase 2
0.6091	Remote Similarity	NPD6083	Phase 2
0.6087	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7983	Approved
0.6064	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD5125	Phase 3
0.6048	Remote Similarity	NPD5126	Approved
0.6044	Remote Similarity	NPD371	Approved
0.6034	Remote Similarity	NPD6011	Approved
0.6032	Remote Similarity	NPD6336	Discontinued
0.6019	Remote Similarity	NPD3133	Approved
0.6019	Remote Similarity	NPD3665	Phase 1
0.6019	Remote Similarity	NPD3666	Approved
0.6019	Remote Similarity	NPD3668	Phase 3
0.6018	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD5225	Approved
0.6018	Remote Similarity	NPD5226	Approved
0.6018	Remote Similarity	NPD5211	Phase 2
0.6018	Remote Similarity	NPD4633	Approved
0.6018	Remote Similarity	NPD5224	Approved
0.6017	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6640	Phase 3
0.6	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD3573	Approved
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4768	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