NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	898.49
Volume:	873.961
LogP:	2.641
LogD:	2.845
LogS:	-3.833
# Rotatable Bonds:	9
TPSA:	255.91
# H-Bond Aceptor:	17
# H-Bond Donor:	9
# Rings:	9
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.114
Synthetic Accessibility Score:	7.838
Fsp3:	0.957
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:	-5.597
MDCK Permeability:	8.932980563258752e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.837
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	76.96691131591797%
Volume Distribution (VD):	0.053
Pgp-substrate:	8.468255996704102%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.456
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.315
CYP3A4-substrate:	0.05

ADMET: Excretion

Clearance (CL):	0.538
Half-life (T1/2):	0.729

ADMET: Toxicity

hERG Blockers:	0.118
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.085
Rat Oral Acute Toxicity:	0.19
Maximum Recommended Daily Dose:	0.23
Skin Sensitization:	0.904
Carcinogencity:	0.012
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC476690

Natural Product ID:	NPC476690
*Common Name:**	bacopaside VII
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5-hydroxy-2-[[(1R,2R,5R,7S,10R,11R,14S,15S,16S,20S)-16-hydroxy-2,6,6,10,16-pentamethyl-18-(2-methylprop-1-enyl)-19,21-dioxahexacyclo[18.2.1.01,14.02,11.05,10.015,20]tricosan-7-yl]oxy]oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	bacopaside VII
Standard InCHIKey:	RANQPHKSRUUPKK-DKVMZZTFSA-N
Standard InCHI:	InChI=1S/C46H74O17/c1-21(2)14-22-15-44(7,55)37-23-8-9-28-42(5)12-11-29(41(3,4)27(42)10-13-43(28,6)45(23)19-46(37,63-22)57-20-45)60-40-36(62-38-33(53)31(51)26(17-48)59-38)35(24(49)18-56-40)61-39-34(54)32(52)30(50)25(16-47)58-39/h14,22-40,47-55H,8-13,15-20H2,1-7H3/t22?,23-,24-,25+,26-,27-,28+,29-,30+,31-,32-,33+,34+,35-,36+,37-,38-,39-,40-,42-,43+,44-,45+,46-/m0/s1
SMILES:	CC(=CC1C[C@]([C@@H]2[C@@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]36C[C@@]2(O1)OC6)C)(C)C)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H](O9)CO)O)O)C)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44421667
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO1097	Bacopa monnieri	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502309]
NPO1097	Bacopa monnieri	Species	Plantaginaceae	Eukaryota	whole plant	Zhangzhou, Fujian Province, China	n.a.	PMID[17343408]
NPO1097	Bacopa monnieri	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1097	Bacopa monnieri	Species	Plantaginaceae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	20	%	PMID[17343408]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	8	%	PMID[17343408]

☑ 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 NPC476690 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	343
0.1-0.2	2249
0.2-0.3	6651
0.3-0.4	13818
0.4-0.5	8891
0.5-0.6	6006
0.6-0.7	2698
0.7-0.8	1364
0.8-0.85	386
0.85-0.9	256
0.9-0.95	30
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC100048
0.9907	High Similarity	NPC10366
0.9633	High Similarity	NPC20979
0.9537	High Similarity	NPC476693
0.9252	High Similarity	NPC220427
0.9196	High Similarity	NPC476691
0.9196	High Similarity	NPC476692
0.9182	High Similarity	NPC469348
0.9182	High Similarity	NPC469347
0.9167	High Similarity	NPC14630
0.9167	High Similarity	NPC250089
0.9167	High Similarity	NPC157530
0.9123	High Similarity	NPC120390
0.9123	High Similarity	NPC475590
0.9123	High Similarity	NPC474908
0.9123	High Similarity	NPC475419
0.9099	High Similarity	NPC11548
0.9091	High Similarity	NPC42171
0.9091	High Similarity	NPC112274
0.9091	High Similarity	NPC254255
0.9083	High Similarity	NPC247037
0.9074	High Similarity	NPC125324
0.9074	High Similarity	NPC51172
0.9074	High Similarity	NPC49032
0.9065	High Similarity	NPC152584
0.9065	High Similarity	NPC127801
0.9065	High Similarity	NPC208594
0.9065	High Similarity	NPC194842
0.9065	High Similarity	NPC160816
0.9065	High Similarity	NPC208477
0.9065	High Similarity	NPC69737
0.9065	High Similarity	NPC269627
0.9043	High Similarity	NPC474423
0.9043	High Similarity	NPC43842
0.9043	High Similarity	NPC74259
0.9035	High Similarity	NPC72260
0.9018	High Similarity	NPC477029
0.9018	High Similarity	NPC477030
0.9009	High Similarity	NPC51154
0.9	High Similarity	NPC472987
0.9	High Similarity	NPC197231
0.9	High Similarity	NPC13190
0.9	High Similarity	NPC473021
0.8991	High Similarity	NPC151134
0.8981	High Similarity	NPC208650
0.8981	High Similarity	NPC14946
0.8981	High Similarity	NPC54619
0.8981	High Similarity	NPC231340
0.8981	High Similarity	NPC63368
0.8981	High Similarity	NPC181467
0.8966	High Similarity	NPC308262
0.8966	High Similarity	NPC208193
0.8966	High Similarity	NPC202261
0.8966	High Similarity	NPC106589
0.8966	High Similarity	NPC257207
0.8966	High Similarity	NPC117445
0.8966	High Similarity	NPC295133
0.8957	High Similarity	NPC314535
0.8957	High Similarity	NPC173555
0.8947	High Similarity	NPC469756
0.8947	High Similarity	NPC292467
0.8947	High Similarity	NPC30483
0.8947	High Similarity	NPC55532
0.8947	High Similarity	NPC236973
0.8947	High Similarity	NPC32177
0.8947	High Similarity	NPC470897
0.8929	High Similarity	NPC477810
0.8919	High Similarity	NPC19888
0.8909	High Similarity	NPC103627
0.8909	High Similarity	NPC191439
0.8909	High Similarity	NPC170974
0.8909	High Similarity	NPC470867
0.8909	High Similarity	NPC141433
0.8899	High Similarity	NPC180183
0.8899	High Similarity	NPC159005
0.8899	High Similarity	NPC6931
0.8899	High Similarity	NPC246124
0.8899	High Similarity	NPC98696
0.8879	High Similarity	NPC157659
0.8879	High Similarity	NPC472252
0.8879	High Similarity	NPC193893
0.8879	High Similarity	NPC189852
0.8879	High Similarity	NPC245280
0.8879	High Similarity	NPC286969
0.8879	High Similarity	NPC114874
0.8879	High Similarity	NPC155010
0.8879	High Similarity	NPC31907
0.8879	High Similarity	NPC473020
0.8879	High Similarity	NPC16520
0.8879	High Similarity	NPC213190
0.8879	High Similarity	NPC131479
0.8879	High Similarity	NPC264336
0.8879	High Similarity	NPC120123
0.8879	High Similarity	NPC8039
0.8879	High Similarity	NPC211879
0.887	High Similarity	NPC475629
0.887	High Similarity	NPC475556
0.885	High Similarity	NPC148965
0.8829	High Similarity	NPC157474
0.8829	High Similarity	NPC475247
0.8829	High Similarity	NPC477028
0.8829	High Similarity	NPC294129
0.8829	High Similarity	NPC477032
0.8829	High Similarity	NPC476547
0.8829	High Similarity	NPC124677
0.8829	High Similarity	NPC472715
0.8829	High Similarity	NPC110494
0.8818	High Similarity	NPC102016
0.8818	High Similarity	NPC244086
0.8818	High Similarity	NPC22779
0.8818	High Similarity	NPC218571
0.8818	High Similarity	NPC95051
0.8818	High Similarity	NPC306131
0.8818	High Similarity	NPC477027
0.8818	High Similarity	NPC475333
0.8818	High Similarity	NPC224098
0.8818	High Similarity	NPC300557
0.8818	High Similarity	NPC473318
0.8818	High Similarity	NPC232054
0.8818	High Similarity	NPC208383
0.8818	High Similarity	NPC248746
0.8818	High Similarity	NPC194207
0.8818	High Similarity	NPC249265
0.8818	High Similarity	NPC70204
0.8818	High Similarity	NPC28844
0.8818	High Similarity	NPC475670
0.8818	High Similarity	NPC46190
0.8818	High Similarity	NPC470433
0.8818	High Similarity	NPC150372
0.8818	High Similarity	NPC476835
0.8818	High Similarity	NPC73243
0.8818	High Similarity	NPC6806
0.8818	High Similarity	NPC473328
0.8818	High Similarity	NPC84956
0.8818	High Similarity	NPC171073
0.8818	High Similarity	NPC477026
0.8818	High Similarity	NPC309278
0.8818	High Similarity	NPC40440
0.8818	High Similarity	NPC472901
0.8818	High Similarity	NPC477809
0.8818	High Similarity	NPC475550
0.8818	High Similarity	NPC42482
0.8807	High Similarity	NPC113044
0.8807	High Similarity	NPC161676
0.8807	High Similarity	NPC281939
0.8807	High Similarity	NPC14704
0.8807	High Similarity	NPC190395
0.8807	High Similarity	NPC305423
0.8807	High Similarity	NPC470432
0.8807	High Similarity	NPC473469
0.8807	High Similarity	NPC283829
0.8807	High Similarity	NPC230507
0.8796	High Similarity	NPC165033
0.8796	High Similarity	NPC475365
0.8796	High Similarity	NPC273879
0.8793	High Similarity	NPC475219
0.8793	High Similarity	NPC231518
0.8793	High Similarity	NPC40749
0.8785	High Similarity	NPC312553
0.8785	High Similarity	NPC159036
0.8785	High Similarity	NPC288694
0.8783	High Similarity	NPC473633
0.8783	High Similarity	NPC476085
0.8783	High Similarity	NPC195560
0.8783	High Similarity	NPC329905
0.8783	High Similarity	NPC229962
0.8772	High Similarity	NPC93883
0.8761	High Similarity	NPC32707
0.8761	High Similarity	NPC167183
0.875	High Similarity	NPC476305
0.875	High Similarity	NPC475354
0.875	High Similarity	NPC263359
0.875	High Similarity	NPC473567
0.875	High Similarity	NPC210569
0.875	High Similarity	NPC472716
0.875	High Similarity	NPC244431
0.875	High Similarity	NPC216595
0.875	High Similarity	NPC32361
0.875	High Similarity	NPC31896
0.875	High Similarity	NPC231797
0.8739	High Similarity	NPC222202
0.8739	High Similarity	NPC65155
0.8739	High Similarity	NPC269297
0.8739	High Similarity	NPC472717
0.8739	High Similarity	NPC87998
0.8739	High Similarity	NPC477811
0.8739	High Similarity	NPC23808
0.8739	High Similarity	NPC224314
0.8727	High Similarity	NPC476540
0.8727	High Similarity	NPC472897
0.8727	High Similarity	NPC476541
0.8727	High Similarity	NPC476513
0.8727	High Similarity	NPC7213
0.8727	High Similarity	NPC476538
0.8727	High Similarity	NPC472896
0.8727	High Similarity	NPC476539
0.8716	High Similarity	NPC472900
0.8716	High Similarity	NPC242748
0.8716	High Similarity	NPC472899
0.8716	High Similarity	NPC472898

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 NPC476690 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	2357
0.2-0.3	4226
0.3-0.4	1530
0.4-0.5	422
0.5-0.6	266
0.6-0.7	39
0.7-0.8	12
0.8-0.85	5
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9035	High Similarity	NPD8294	Approved
0.9035	High Similarity	NPD8377	Approved
0.8957	High Similarity	NPD8335	Approved
0.8957	High Similarity	NPD8378	Approved
0.8957	High Similarity	NPD8296	Approved
0.8957	High Similarity	NPD8380	Approved
0.8957	High Similarity	NPD8379	Approved
0.8793	High Similarity	NPD8033	Approved
0.8534	High Similarity	NPD7328	Approved
0.8534	High Similarity	NPD7327	Approved
0.8462	Intermediate Similarity	NPD7516	Approved
0.819	Intermediate Similarity	NPD8133	Approved
0.8049	Intermediate Similarity	NPD7507	Approved
0.8037	Intermediate Similarity	NPD8171	Discontinued
0.8017	Intermediate Similarity	NPD7503	Approved
0.7857	Intermediate Similarity	NPD7319	Approved
0.7373	Intermediate Similarity	NPD6412	Phase 2
0.735	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD8450	Suspended
0.7273	Intermediate Similarity	NPD8449	Approved
0.7231	Intermediate Similarity	NPD7736	Approved
0.7214	Intermediate Similarity	NPD7625	Phase 1
0.7167	Intermediate Similarity	NPD6686	Approved
0.7109	Intermediate Similarity	NPD6370	Approved
0.7069	Intermediate Similarity	NPD7638	Approved
0.7054	Intermediate Similarity	NPD8328	Phase 3
0.7031	Intermediate Similarity	NPD8515	Approved
0.7031	Intermediate Similarity	NPD8516	Approved
0.7031	Intermediate Similarity	NPD8517	Approved
0.7031	Intermediate Similarity	NPD8513	Phase 3
0.7023	Intermediate Similarity	NPD8293	Discontinued
0.7009	Intermediate Similarity	NPD7640	Approved
0.7009	Intermediate Similarity	NPD7639	Approved
0.6967	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD6054	Approved
0.6953	Remote Similarity	NPD6059	Approved
0.6916	Remote Similarity	NPD6928	Phase 2
0.6916	Remote Similarity	NPD7525	Registered
0.685	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6016	Approved
0.6769	Remote Similarity	NPD6015	Approved
0.6767	Remote Similarity	NPD7078	Approved
0.6742	Remote Similarity	NPD7492	Approved
0.672	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD5988	Approved
0.6692	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6067	Discontinued
0.6637	Remote Similarity	NPD7524	Approved
0.6535	Remote Similarity	NPD8297	Approved
0.6535	Remote Similarity	NPD6882	Approved
0.6518	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7645	Phase 2
0.6491	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD7632	Discontinued
0.6471	Remote Similarity	NPD6033	Approved
0.6462	Remote Similarity	NPD7115	Discovery
0.6462	Remote Similarity	NPD6009	Approved
0.6439	Remote Similarity	NPD6319	Approved
0.6429	Remote Similarity	NPD6695	Phase 3
0.6393	Remote Similarity	NPD4159	Approved
0.6379	Remote Similarity	NPD6051	Approved
0.6364	Remote Similarity	NPD4225	Approved
0.6357	Remote Similarity	NPD4632	Approved
0.6349	Remote Similarity	NPD7320	Approved
0.6348	Remote Similarity	NPD7750	Discontinued
0.632	Remote Similarity	NPD6402	Approved
0.632	Remote Similarity	NPD6675	Approved
0.632	Remote Similarity	NPD5739	Approved
0.632	Remote Similarity	NPD7128	Approved
0.6299	Remote Similarity	NPD6372	Approved
0.6299	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD7991	Discontinued
0.6239	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6881	Approved
0.622	Remote Similarity	NPD6899	Approved
0.6202	Remote Similarity	NPD6649	Approved
0.6202	Remote Similarity	NPD6650	Approved
0.6202	Remote Similarity	NPD8130	Phase 1
0.619	Remote Similarity	NPD6008	Approved
0.6161	Remote Similarity	NPD6931	Approved
0.6161	Remote Similarity	NPD6930	Phase 2
0.6159	Remote Similarity	NPD8074	Phase 3
0.6154	Remote Similarity	NPD6053	Discontinued
0.6148	Remote Similarity	NPD4755	Approved
0.6147	Remote Similarity	NPD7339	Approved
0.6147	Remote Similarity	NPD6942	Approved
0.6142	Remote Similarity	NPD5701	Approved
0.6142	Remote Similarity	NPD5697	Approved
0.6134	Remote Similarity	NPD8035	Phase 2
0.6134	Remote Similarity	NPD8034	Phase 2
0.6129	Remote Similarity	NPD5344	Discontinued
0.6124	Remote Similarity	NPD6883	Approved
0.6124	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD4634	Approved
0.6124	Remote Similarity	NPD7102	Approved
0.6124	Remote Similarity	NPD7290	Approved
0.6098	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6933	Approved
0.6083	Remote Similarity	NPD4202	Approved
0.608	Remote Similarity	NPD5211	Phase 2
0.6077	Remote Similarity	NPD6617	Approved
0.6077	Remote Similarity	NPD6869	Approved
0.6077	Remote Similarity	NPD6847	Approved
0.6071	Remote Similarity	NPD6929	Approved
0.6058	Remote Similarity	NPD7604	Phase 2
0.6048	Remote Similarity	NPD4700	Approved
0.6048	Remote Similarity	NPD4696	Approved
0.6048	Remote Similarity	NPD5285	Approved
0.6048	Remote Similarity	NPD5286	Approved
0.6047	Remote Similarity	NPD6014	Approved
0.6047	Remote Similarity	NPD6013	Approved
0.6047	Remote Similarity	NPD6012	Approved
0.6033	Remote Similarity	NPD7748	Approved
0.6029	Remote Similarity	NPD5983	Phase 2
0.6028	Remote Similarity	NPD5956	Approved
0.6019	Remote Similarity	NPD4243	Approved
0.6018	Remote Similarity	NPD7514	Phase 3
0.6016	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6083	Phase 2
0.6016	Remote Similarity	NPD7902	Approved
0.6016	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD7087	Discontinued
0.6	Remote Similarity	NPD7799	Discontinued
0.5984	Remote Similarity	NPD5141	Approved
0.5981	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD6336	Discontinued
0.5969	Remote Similarity	NPD6011	Approved
0.5954	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD5225	Approved
0.5952	Remote Similarity	NPD5224	Approved
0.5952	Remote Similarity	NPD5226	Approved
0.5952	Remote Similarity	NPD4633	Approved
0.595	Remote Similarity	NPD6399	Phase 3
0.5938	Remote Similarity	NPD4768	Approved
0.5938	Remote Similarity	NPD4767	Approved
0.5909	Remote Similarity	NPD1811	Approved
0.5909	Remote Similarity	NPD4784	Approved
0.5909	Remote Similarity	NPD4785	Approved
0.5909	Remote Similarity	NPD1810	Approved
0.5909	Remote Similarity	NPD6924	Approved
0.5909	Remote Similarity	NPD6926	Approved
0.5906	Remote Similarity	NPD5174	Approved
0.5906	Remote Similarity	NPD5175	Approved
0.5897	Remote Similarity	NPD6893	Approved
0.5897	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6925	Approved
0.5893	Remote Similarity	NPD5776	Phase 2
0.5893	Remote Similarity	NPD6932	Approved
0.5891	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD7332	Phase 2
0.5877	Remote Similarity	NPD4748	Discontinued
0.5873	Remote Similarity	NPD5223	Approved
0.587	Remote Similarity	NPD5126	Approved
0.587	Remote Similarity	NPD5125	Phase 3
0.5868	Remote Similarity	NPD7637	Suspended
0.5868	Remote Similarity	NPD7515	Phase 2
0.5854	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD4729	Approved
0.5846	Remote Similarity	NPD4730	Approved
0.5841	Remote Similarity	NPD7145	Approved
0.5839	Remote Similarity	NPD7741	Discontinued
0.5833	Remote Similarity	NPD5328	Approved
0.5833	Remote Similarity	NPD4753	Phase 2
0.5826	Remote Similarity	NPD6902	Approved
0.5814	Remote Similarity	NPD6640	Phase 3
0.5812	Remote Similarity	NPD4786	Approved
0.5794	Remote Similarity	NPD6648	Approved
0.5789	Remote Similarity	NPD6683	Phase 2
0.5785	Remote Similarity	NPD6698	Approved
0.5785	Remote Similarity	NPD46	Approved
0.5785	Remote Similarity	NPD7838	Discovery
0.5785	Remote Similarity	NPD3168	Discontinued
0.5781	Remote Similarity	NPD4754	Approved
0.5778	Remote Similarity	NPD6274	Approved
0.5772	Remote Similarity	NPD7900	Approved
0.5772	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7101	Approved
0.5766	Remote Similarity	NPD7100	Approved
0.5763	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD5247	Approved
0.5758	Remote Similarity	NPD5250	Approved
0.5758	Remote Similarity	NPD6371	Approved
0.5758	Remote Similarity	NPD5249	Phase 3
0.5758	Remote Similarity	NPD5251	Approved
0.5758	Remote Similarity	NPD5248	Approved
0.575	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD7509	Discontinued
0.5738	Remote Similarity	NPD6079	Approved
0.5726	Remote Similarity	NPD5695	Phase 3
0.5725	Remote Similarity	NPD5128	Approved
0.5714	Remote Similarity	NPD5275	Approved
0.5714	Remote Similarity	NPD5696	Approved
0.5714	Remote Similarity	NPD4190	Phase 3
0.5714	Remote Similarity	NPD3618	Phase 1
0.5693	Remote Similarity	NPD6335	Approved
0.569	Remote Similarity	NPD6898	Phase 1
0.5686	Remote Similarity	NPD6674	Discontinued
0.5683	Remote Similarity	NPD6909	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