NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	978.52
Volume:	973.162
LogP:	2.87
LogD:	1.624
LogS:	-3.488
# Rotatable Bonds:	13
TPSA:	288.66
# H-Bond Aceptor:	18
# H-Bond Donor:	9
# Rings:	7
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.062
Synthetic Accessibility Score:	6.614
Fsp3:	0.824
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:	-5.614
MDCK Permeability:	5.443610643851571e-05
Pgp-inhibitor:	0.965
Pgp-substrate:	0.641
Human Intestinal Absorption (HIA):	0.85
20% Bioavailability (F20%):	0.065
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	80.47100067138672%
Volume Distribution (VD):	0.402
Pgp-substrate:	5.9161176681518555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.255
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.196
CYP3A4-substrate:	0.033

ADMET: Excretion

Clearance (CL):	0.968
Half-life (T1/2):	0.868

ADMET: Toxicity

hERG Blockers:	0.2
Human Hepatotoxicity (H-HT):	0.304
Drug-inuced Liver Injury (DILI):	0.083
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.242
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.64

Download Data

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

Natural Product: NPC477191

Natural Product ID:	NPC477191
*Common Name:**	3beta-[3-O-(alpha-L-Arabinopyranosyl)-beta-D-glucopyranuronosyloxy]-16alpha,23,28-trihydroxy-21beta,22alpha-bis(angeloyloxy)oleana-12-ene
IUPAC Name:	(2S,3S,4S,5R,6R)-6-[[(3S,4R,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-9,10-bis[[(Z)-2-methylbut-2-enoyl]oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms:
Standard InCHIKey:	WGPUVZRQQKVFDP-NFNBLRENSA-N
Standard InCHI:	InChI=1S/C51H78O18/c1-11-24(3)42(62)68-39-40(69-43(63)25(4)12-2)51(23-53)27(19-46(39,5)6)26-13-14-30-47(7)17-16-32(48(8,22-52)29(47)15-18-49(30,9)50(26,10)20-31(51)55)65-45-36(59)37(35(58)38(67-45)41(60)61)66-44-34(57)33(56)28(54)21-64-44/h11-13,27-40,44-45,52-59H,14-23H2,1-10H3,(H,60,61)/b24-11-,25-12-/t27-,28-,29+,30+,31+,32-,33-,34+,35-,36+,37-,38-,39-,40-,44-,45+,47-,48-,49+,50+,51-/m0/s1
SMILES:	C/C=C(/C)\C(=O)O[C@H]1[C@@H](C(C[C@@H]2[C@]1([C@@H](C[C@@]3(C2=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H]([C@@]5(C)CO)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O)O)C)C)C)O)CO)(C)C)OC(=O)/C(=C\C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44140277
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
NPO31118	Gordonia chrysandra	Species	Theaceae	Eukaryota	Roots	Yunnan Province, China	2005-MAY	PMID[20560647]
NPO31118	Gordonia chrysandra	Species	Theaceae	Eukaryota	n.a.	stem	n.a.	PMID[21473609]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	4700	nM	PMID[20560647]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	5500	nM	PMID[20560647]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000	nM	PMID[20560647]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000	nM	PMID[20560647]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000	nM	PMID[20560647]

☑ 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 NPC477191 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	316
0.1-0.2	1918
0.2-0.3	4898
0.3-0.4	8354
0.4-0.5	11976
0.5-0.6	8202
0.6-0.7	4357
0.7-0.8	1837
0.8-0.85	295
0.85-0.9	318
0.9-0.95	132
0.95-1	94

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477193
1.0	High Similarity	NPC477192
1.0	High Similarity	NPC477194
0.9915	High Similarity	NPC88311
0.9915	High Similarity	NPC107536
0.9915	High Similarity	NPC97918
0.9915	High Similarity	NPC477076
0.9915	High Similarity	NPC269484
0.9915	High Similarity	NPC141600
0.9915	High Similarity	NPC1314
0.9915	High Similarity	NPC115656
0.9915	High Similarity	NPC472267
0.9915	High Similarity	NPC470913
0.9915	High Similarity	NPC11577
0.9915	High Similarity	NPC470518
0.9915	High Similarity	NPC252657
0.9915	High Similarity	NPC273878
0.9915	High Similarity	NPC244296
0.9915	High Similarity	NPC477077
0.9915	High Similarity	NPC305793
0.9915	High Similarity	NPC477196
0.9915	High Similarity	NPC280029
0.9915	High Similarity	NPC477079
0.9915	High Similarity	NPC252289
0.9915	High Similarity	NPC82380
0.9915	High Similarity	NPC9470
0.9832	High Similarity	NPC477197
0.9832	High Similarity	NPC476774
0.9832	High Similarity	NPC271610
0.9832	High Similarity	NPC478155
0.9832	High Similarity	NPC476780
0.9832	High Similarity	NPC25998
0.9832	High Similarity	NPC476775
0.9831	High Similarity	NPC475281
0.9831	High Similarity	NPC329923
0.9831	High Similarity	NPC477078
0.9831	High Similarity	NPC477075
0.975	High Similarity	NPC46823
0.975	High Similarity	NPC312650
0.975	High Similarity	NPC277212
0.975	High Similarity	NPC71391
0.975	High Similarity	NPC178264
0.975	High Similarity	NPC30279
0.975	High Similarity	NPC192765
0.975	High Similarity	NPC478152
0.975	High Similarity	NPC476776
0.975	High Similarity	NPC473918
0.975	High Similarity	NPC478153
0.975	High Similarity	NPC478154
0.975	High Similarity	NPC477195
0.975	High Similarity	NPC478150
0.9748	High Similarity	NPC265841
0.9748	High Similarity	NPC470912
0.9748	High Similarity	NPC47995
0.9669	High Similarity	NPC478151
0.9669	High Similarity	NPC225791
0.9667	High Similarity	NPC475377
0.9667	High Similarity	NPC134914
0.9667	High Similarity	NPC478065
0.9667	High Similarity	NPC329993
0.9667	High Similarity	NPC262796
0.9667	High Similarity	NPC173435
0.9667	High Similarity	NPC172374
0.9667	High Similarity	NPC45346
0.9667	High Similarity	NPC475167
0.9667	High Similarity	NPC476074
0.9667	High Similarity	NPC264566
0.9667	High Similarity	NPC301639
0.9667	High Similarity	NPC478064
0.959	High Similarity	NPC476777
0.959	High Similarity	NPC476778
0.9512	High Similarity	NPC110700
0.9512	High Similarity	NPC279915
0.9508	High Similarity	NPC476779
0.9339	High Similarity	NPC470475
0.9328	High Similarity	NPC471964
0.9328	High Similarity	NPC262199
0.9328	High Similarity	NPC471961
0.9328	High Similarity	NPC202666
0.9328	High Similarity	NPC14617
0.9256	High Similarity	NPC470516
0.925	High Similarity	NPC471963
0.925	High Similarity	NPC247315
0.925	High Similarity	NPC471962
0.9244	High Similarity	NPC213952
0.9244	High Similarity	NPC471965
0.9237	High Similarity	NPC236657
0.9237	High Similarity	NPC118440
0.918	High Similarity	NPC470476
0.9174	High Similarity	NPC285091
0.9167	High Similarity	NPC478066
0.9167	High Similarity	NPC257211
0.916	High Similarity	NPC187618
0.916	High Similarity	NPC171544
0.916	High Similarity	NPC31838
0.916	High Similarity	NPC301449
0.916	High Similarity	NPC64715
0.916	High Similarity	NPC22956
0.916	High Similarity	NPC302887
0.916	High Similarity	NPC222580
0.916	High Similarity	NPC159309
0.916	High Similarity	NPC297263
0.916	High Similarity	NPC86222
0.916	High Similarity	NPC11242
0.916	High Similarity	NPC114484
0.916	High Similarity	NPC62725
0.916	High Similarity	NPC223301
0.916	High Similarity	NPC104372
0.9153	High Similarity	NPC114441
0.9153	High Similarity	NPC35405
0.9153	High Similarity	NPC11551
0.9153	High Similarity	NPC309780
0.9153	High Similarity	NPC472949
0.9153	High Similarity	NPC157868
0.9153	High Similarity	NPC39211
0.9153	High Similarity	NPC180550
0.9153	High Similarity	NPC6377
0.9153	High Similarity	NPC473884
0.9153	High Similarity	NPC475171
0.9153	High Similarity	NPC214484
0.9153	High Similarity	NPC208381
0.9153	High Similarity	NPC469945
0.9145	High Similarity	NPC224121
0.9127	High Similarity	NPC471089
0.9127	High Similarity	NPC190065
0.9127	High Similarity	NPC141215
0.9091	High Similarity	NPC23275
0.9091	High Similarity	NPC33068
0.9083	High Similarity	NPC131469
0.9083	High Similarity	NPC21691
0.9083	High Similarity	NPC80986
0.9083	High Similarity	NPC236870
0.9083	High Similarity	NPC187290
0.9083	High Similarity	NPC40775
0.9083	High Similarity	NPC162574
0.9083	High Similarity	NPC475591
0.9083	High Similarity	NPC107966
0.9083	High Similarity	NPC4749
0.9083	High Similarity	NPC313110
0.9083	High Similarity	NPC10607
0.9083	High Similarity	NPC235438
0.9083	High Similarity	NPC249848
0.9068	High Similarity	NPC286347
0.9055	High Similarity	NPC596
0.9055	High Similarity	NPC295885
0.9055	High Similarity	NPC140045
0.9048	High Similarity	NPC262813
0.9016	High Similarity	NPC284449
0.9008	High Similarity	NPC44716
0.9008	High Similarity	NPC235405
0.9008	High Similarity	NPC302543
0.9008	High Similarity	NPC2370
0.9008	High Similarity	NPC258617
0.9008	High Similarity	NPC30735
0.9008	High Similarity	NPC200049
0.9008	High Similarity	NPC281148
0.9008	High Similarity	NPC283417
0.9	High Similarity	NPC31193
0.9	High Similarity	NPC75417
0.9	High Similarity	NPC242840
0.8992	High Similarity	NPC192791
0.8983	High Similarity	NPC473405
0.8976	High Similarity	NPC251998
0.8934	High Similarity	NPC160452
0.8934	High Similarity	NPC470477
0.8917	High Similarity	NPC294112
0.8908	High Similarity	NPC470515
0.8908	High Similarity	NPC471548
0.8898	High Similarity	NPC268954
0.8898	High Similarity	NPC44170
0.888	High Similarity	NPC300655
0.888	High Similarity	NPC222951
0.888	High Similarity	NPC311178
0.888	High Similarity	NPC43589
0.8871	High Similarity	NPC112492
0.8871	High Similarity	NPC23020
0.8871	High Similarity	NPC472268
0.8871	High Similarity	NPC472269
0.8871	High Similarity	NPC472270
0.8862	High Similarity	NPC469947
0.8862	High Similarity	NPC470218
0.8862	High Similarity	NPC181066
0.8862	High Similarity	NPC475368
0.8833	High Similarity	NPC470911
0.8833	High Similarity	NPC473401
0.8833	High Similarity	NPC470915
0.8833	High Similarity	NPC470914
0.8833	High Similarity	NPC470517
0.8824	High Similarity	NPC300419
0.8814	High Similarity	NPC110861
0.881	High Similarity	NPC196874
0.881	High Similarity	NPC324933
0.881	High Similarity	NPC475177
0.881	High Similarity	NPC319719
0.881	High Similarity	NPC475444
0.881	High Similarity	NPC473679
0.881	High Similarity	NPC183816
0.881	High Similarity	NPC233223
0.881	High Similarity	NPC322904
0.879	High Similarity	NPC470780

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 NPC477191 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	2119
0.2-0.3	3771
0.3-0.4	1909
0.4-0.5	631
0.5-0.6	268
0.6-0.7	117
0.7-0.8	32
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9328	High Similarity	NPD8328	Phase 3
0.8824	High Similarity	NPD8295	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7319	Approved
0.8	Intermediate Similarity	NPD6686	Approved
0.8	Intermediate Similarity	NPD7736	Approved
0.7984	Intermediate Similarity	NPD7507	Approved
0.7934	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD8377	Approved
0.7874	Intermediate Similarity	NPD8294	Approved
0.7823	Intermediate Similarity	NPD8133	Approved
0.7812	Intermediate Similarity	NPD8515	Approved
0.7812	Intermediate Similarity	NPD8517	Approved
0.7812	Intermediate Similarity	NPD8380	Approved
0.7812	Intermediate Similarity	NPD8513	Phase 3
0.7812	Intermediate Similarity	NPD8379	Approved
0.7812	Intermediate Similarity	NPD8378	Approved
0.7812	Intermediate Similarity	NPD8296	Approved
0.7812	Intermediate Similarity	NPD8033	Approved
0.7812	Intermediate Similarity	NPD8335	Approved
0.7812	Intermediate Similarity	NPD8516	Approved
0.7656	Intermediate Similarity	NPD7516	Approved
0.7652	Intermediate Similarity	NPD8293	Discontinued
0.7615	Intermediate Similarity	NPD6370	Approved
0.7578	Intermediate Similarity	NPD7328	Approved
0.7578	Intermediate Similarity	NPD7327	Approved
0.7561	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7503	Approved
0.75	Intermediate Similarity	NPD7492	Approved
0.7462	Intermediate Similarity	NPD6054	Approved
0.7462	Intermediate Similarity	NPD6319	Approved
0.7444	Intermediate Similarity	NPD6616	Approved
0.7388	Intermediate Similarity	NPD7078	Approved
0.7339	Intermediate Similarity	NPD6412	Phase 2
0.7328	Intermediate Similarity	NPD6059	Approved
0.7323	Intermediate Similarity	NPD8297	Approved
0.7323	Intermediate Similarity	NPD6882	Approved
0.7273	Intermediate Similarity	NPD6015	Approved
0.7273	Intermediate Similarity	NPD6016	Approved
0.725	Intermediate Similarity	NPD7902	Approved
0.7231	Intermediate Similarity	NPD6009	Approved
0.7231	Intermediate Similarity	NPD7115	Discovery
0.7218	Intermediate Similarity	NPD5988	Approved
0.719	Intermediate Similarity	NPD7638	Approved
0.719	Intermediate Similarity	NPD4225	Approved
0.7143	Intermediate Similarity	NPD7748	Approved
0.7131	Intermediate Similarity	NPD7640	Approved
0.7131	Intermediate Similarity	NPD7639	Approved
0.7109	Intermediate Similarity	NPD6649	Approved
0.7109	Intermediate Similarity	NPD6650	Approved
0.7109	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6373	Approved
0.7087	Intermediate Similarity	NPD6372	Approved
0.7087	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6921	Approved
0.7008	Intermediate Similarity	NPD6881	Approved
0.7008	Intermediate Similarity	NPD6899	Approved
0.7007	Intermediate Similarity	NPD8074	Phase 3
0.7	Intermediate Similarity	NPD4632	Approved
0.7	Intermediate Similarity	NPD7900	Approved
0.7	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7128	Approved
0.6984	Remote Similarity	NPD6675	Approved
0.6984	Remote Similarity	NPD5739	Approved
0.6984	Remote Similarity	NPD6402	Approved
0.6977	Remote Similarity	NPD8130	Phase 1
0.6975	Remote Similarity	NPD7515	Phase 2
0.6929	Remote Similarity	NPD5697	Approved
0.6899	Remote Similarity	NPD7102	Approved
0.6899	Remote Similarity	NPD6883	Approved
0.6899	Remote Similarity	NPD7290	Approved
0.6875	Remote Similarity	NPD7320	Approved
0.6846	Remote Similarity	NPD6847	Approved
0.6846	Remote Similarity	NPD6617	Approved
0.6846	Remote Similarity	NPD6869	Approved
0.6835	Remote Similarity	NPD6033	Approved
0.6822	Remote Similarity	NPD6012	Approved
0.6822	Remote Similarity	NPD6014	Approved
0.6822	Remote Similarity	NPD6013	Approved
0.6797	Remote Similarity	NPD5701	Approved
0.6797	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7604	Phase 2
0.6774	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD4634	Approved
0.6765	Remote Similarity	NPD5983	Phase 2
0.6744	Remote Similarity	NPD6011	Approved
0.6691	Remote Similarity	NPD6336	Discontinued
0.669	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7830	Approved
0.6667	Remote Similarity	NPD7829	Approved
0.6641	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD7632	Discontinued
0.6612	Remote Similarity	NPD6698	Approved
0.6612	Remote Similarity	NPD46	Approved
0.6606	Remote Similarity	NPD7799	Discontinued
0.6591	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7260	Phase 2
0.6552	Remote Similarity	NPD8415	Approved
0.6535	Remote Similarity	NPD5344	Discontinued
0.6525	Remote Similarity	NPD8448	Approved
0.6519	Remote Similarity	NPD6274	Approved
0.6513	Remote Similarity	NPD7625	Phase 1
0.6496	Remote Similarity	NPD7100	Approved
0.6496	Remote Similarity	NPD7101	Approved
0.6484	Remote Similarity	NPD5211	Phase 2
0.6457	Remote Similarity	NPD5286	Approved
0.6457	Remote Similarity	NPD4696	Approved
0.6457	Remote Similarity	NPD5285	Approved
0.6454	Remote Similarity	NPD8451	Approved
0.645	Remote Similarity	NPD8368	Discontinued
0.6429	Remote Similarity	NPD4755	Approved
0.6429	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD6067	Discontinued
0.6429	Remote Similarity	NPD6084	Phase 2
0.6423	Remote Similarity	NPD6335	Approved
0.6423	Remote Similarity	NPD8035	Phase 2
0.6423	Remote Similarity	NPD8034	Phase 2
0.6423	Remote Similarity	NPD7983	Approved
0.6423	Remote Similarity	NPD6411	Approved
0.6397	Remote Similarity	NPD6868	Approved
0.6391	Remote Similarity	NPD6371	Approved
0.6389	Remote Similarity	NPD8392	Approved
0.6389	Remote Similarity	NPD8390	Approved
0.6389	Remote Similarity	NPD8391	Approved
0.6385	Remote Similarity	NPD5141	Approved
0.6371	Remote Similarity	NPD5778	Approved
0.6371	Remote Similarity	NPD5779	Approved
0.6364	Remote Similarity	NPD3573	Approved
0.6357	Remote Similarity	NPD5224	Approved
0.6357	Remote Similarity	NPD4633	Approved
0.6357	Remote Similarity	NPD5226	Approved
0.6357	Remote Similarity	NPD5225	Approved
0.6357	Remote Similarity	NPD8080	Discontinued
0.635	Remote Similarity	NPD6317	Approved
0.6349	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5222	Approved
0.6349	Remote Similarity	NPD4697	Phase 3
0.6349	Remote Similarity	NPD5221	Approved
0.6341	Remote Similarity	NPD7838	Discovery
0.6337	Remote Similarity	NPD8407	Phase 2
0.6336	Remote Similarity	NPD6008	Approved
0.6328	Remote Similarity	NPD4700	Approved
0.6312	Remote Similarity	NPD7642	Approved
0.6308	Remote Similarity	NPD5174	Approved
0.6308	Remote Similarity	NPD5175	Approved
0.6304	Remote Similarity	NPD6313	Approved
0.6304	Remote Similarity	NPD6314	Approved
0.6301	Remote Similarity	NPD6845	Suspended
0.6299	Remote Similarity	NPD5173	Approved
0.6296	Remote Similarity	NPD6053	Discontinued
0.629	Remote Similarity	NPD6079	Approved
0.6286	Remote Similarity	NPD8444	Approved
0.6286	Remote Similarity	NPD6908	Approved
0.6286	Remote Similarity	NPD6909	Approved
0.6279	Remote Similarity	NPD5223	Approved
0.6276	Remote Similarity	NPD5956	Approved
0.6272	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD8340	Approved
0.6268	Remote Similarity	NPD8342	Approved
0.6268	Remote Similarity	NPD8299	Approved
0.6268	Remote Similarity	NPD8341	Approved
0.626	Remote Similarity	NPD5328	Approved
0.626	Remote Similarity	NPD6101	Approved
0.626	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8337	Approved
0.625	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD8336	Approved
0.6241	Remote Similarity	NPD4729	Approved
0.6241	Remote Similarity	NPD4730	Approved
0.624	Remote Similarity	NPD6399	Phase 3
0.6239	Remote Similarity	NPD7645	Phase 2
0.6215	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD4767	Approved
0.6212	Remote Similarity	NPD4768	Approved
0.6202	Remote Similarity	NPD6648	Approved
0.6193	Remote Similarity	NPD8435	Approved
0.619	Remote Similarity	NPD8338	Approved
0.6179	Remote Similarity	NPD6672	Approved
0.6179	Remote Similarity	NPD5737	Approved
0.617	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.617	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD5251	Approved
0.6148	Remote Similarity	NPD5247	Approved
0.6148	Remote Similarity	NPD3618	Phase 1
0.6148	Remote Similarity	NPD5249	Phase 3
0.6148	Remote Similarity	NPD5248	Approved
0.6148	Remote Similarity	NPD5250	Approved
0.6142	Remote Similarity	NPD5695	Phase 3
0.6142	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD5128	Approved
0.6111	Remote Similarity	NPD8171	Discontinued
0.6102	Remote Similarity	NPD8360	Approved
0.6102	Remote Similarity	NPD8361	Approved
0.6094	Remote Similarity	NPD7839	Suspended
0.6093	Remote Similarity	NPD6333	Approved
0.6093	Remote Similarity	NPD6334	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