NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	978.45
Volume:	918.841
LogP:	1.618
LogD:	1.138
LogS:	-2.239
# Rotatable Bonds:	11
TPSA:	299.28
# H-Bond Aceptor:	20
# H-Bond Donor:	9
# Rings:	9
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.076
Synthetic Accessibility Score:	4.339
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:	-5.679
MDCK Permeability:	7.103250391082838e-05
Pgp-inhibitor:	0.297
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.945
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	76.55658721923828%
Volume Distribution (VD):	0.167
Pgp-substrate:	7.265725612640381%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.917
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.085
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.007

ADMET: Excretion

Clearance (CL):	0.65
Half-life (T1/2):	0.615

ADMET: Toxicity

hERG Blockers:	0.244
Human Hepatotoxicity (H-HT):	0.242
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.119
Rat Oral Acute Toxicity:	0.38
Maximum Recommended Daily Dose:	0.727
Skin Sensitization:	0.862
Carcinogencity:	0.02
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC476691

Natural Product ID:	NPC476691
*Common Name:**	[(2R,3S,4S,5R,6R)-6-[(2R,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,17R,20R)-16-hydroxy-2,6,6,10,16-pentamethyl-17-(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-3,4,5-trihydroxyoxan-2-yl]methyl hydrogen sulfate
IUPAC Name:	[(2R,3S,4S,5R,6R)-6-[(2R,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,17R,20R)-16-hydroxy-2,6,6,10,16-pentamethyl-17-(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-3,4,5-trihydroxyoxan-2-yl]methyl hydrogen sulfate
Synonyms:	Bacopaside I
Standard InCHIKey:	SKFWOYHZBNAJGA-DKZUISOASA-N
Standard InCHI:	InChI=1S/C46H74O20S/c1-21(2)14-22-16-59-46-19-45(20-60-46)23(37(46)44(22,7)54)8-9-28-42(5)12-11-29(41(3,4)27(42)10-13-43(28,45)6)64-40-36(66-38-33(52)30(49)25(15-47)62-38)35(24(48)17-58-40)65-39-34(53)32(51)31(50)26(63-39)18-61-67(55,56)57/h14,22-40,47-54H,8-13,15-20H2,1-7H3,(H,55,56,57)/t22-,23+,24+,25+,26-,27+,28-,29+,30+,31-,32+,33-,34-,35+,36-,37+,38+,39-,40-,42+,43-,44+,45-,46-/m1/s1
SMILES:	CC(=C[C@@H]1CO[C@]23C[C@@]4(CO2)[C@H]([C@H]3[C@@]1(C)O)CC[C@H]5[C@]4(CC[C@@H]6[C@@]5(CC[C@@H](C6(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)COS(=O)(=O)O)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H](O9)CO)O)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44421668
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	=	75	%	PMID[17343408]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	61	%	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 NPC476691 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	338
0.1-0.2	2502
0.2-0.3	8375
0.3-0.4	14402
0.4-0.5	7852
0.5-0.6	5216
0.6-0.7	2255
0.7-0.8	1235
0.8-0.85	327
0.85-0.9	127
0.9-0.95	65
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476692
0.963	High Similarity	NPC476693
0.9196	High Similarity	NPC100048
0.9196	High Similarity	NPC476690
0.9182	High Similarity	NPC254255
0.9174	High Similarity	NPC247037
0.9167	High Similarity	NPC220427
0.9115	High Similarity	NPC10366
0.9099	High Similarity	NPC476671
0.9091	High Similarity	NPC197231
0.9018	High Similarity	NPC477810
0.9009	High Similarity	NPC475312
0.9009	High Similarity	NPC19888
0.8991	High Similarity	NPC475634
0.8991	High Similarity	NPC98696
0.8981	High Similarity	NPC160816
0.8981	High Similarity	NPC127801
0.8981	High Similarity	NPC208477
0.8981	High Similarity	NPC269627
0.8981	High Similarity	NPC152584
0.8981	High Similarity	NPC208594
0.8981	High Similarity	NPC69737
0.8981	High Similarity	NPC194842
0.8919	High Similarity	NPC477032
0.8919	High Similarity	NPC475247
0.8919	High Similarity	NPC477028
0.8919	High Similarity	NPC124677
0.8919	High Similarity	NPC476547
0.8919	High Similarity	NPC294129
0.8909	High Similarity	NPC248746
0.8909	High Similarity	NPC309278
0.8909	High Similarity	NPC475550
0.8909	High Similarity	NPC150372
0.8909	High Similarity	NPC42482
0.8909	High Similarity	NPC84956
0.8909	High Similarity	NPC194207
0.8909	High Similarity	NPC475670
0.8909	High Similarity	NPC470433
0.8909	High Similarity	NPC475333
0.8909	High Similarity	NPC22779
0.8909	High Similarity	NPC477026
0.8909	High Similarity	NPC102016
0.8909	High Similarity	NPC474573
0.8909	High Similarity	NPC244086
0.8909	High Similarity	NPC249265
0.8909	High Similarity	NPC477027
0.8909	High Similarity	NPC477809
0.8909	High Similarity	NPC46190
0.8909	High Similarity	NPC224098
0.8909	High Similarity	NPC73243
0.8909	High Similarity	NPC232054
0.8909	High Similarity	NPC40440
0.8909	High Similarity	NPC95051
0.8909	High Similarity	NPC306131
0.8909	High Similarity	NPC6806
0.8909	High Similarity	NPC70204
0.8909	High Similarity	NPC300557
0.8909	High Similarity	NPC218571
0.8909	High Similarity	NPC208383
0.8909	High Similarity	NPC171073
0.8899	High Similarity	NPC161676
0.8899	High Similarity	NPC473469
0.8899	High Similarity	NPC283829
0.8899	High Similarity	NPC181467
0.8899	High Similarity	NPC63368
0.8899	High Similarity	NPC14946
0.8899	High Similarity	NPC305423
0.8899	High Similarity	NPC208650
0.8899	High Similarity	NPC470432
0.8899	High Similarity	NPC230507
0.8899	High Similarity	NPC14704
0.8899	High Similarity	NPC113044
0.8899	High Similarity	NPC190395
0.886	High Similarity	NPC20979
0.885	High Similarity	NPC32707
0.885	High Similarity	NPC167183
0.8839	High Similarity	NPC32361
0.8839	High Similarity	NPC210569
0.8839	High Similarity	NPC244431
0.8839	High Similarity	NPC263359
0.8839	High Similarity	NPC31896
0.8829	High Similarity	NPC87998
0.8829	High Similarity	NPC222202
0.8829	High Similarity	NPC23808
0.8829	High Similarity	NPC224314
0.8829	High Similarity	NPC269297
0.8829	High Similarity	NPC477811
0.8818	High Similarity	NPC246124
0.8818	High Similarity	NPC7213
0.8818	High Similarity	NPC476538
0.8818	High Similarity	NPC159005
0.8818	High Similarity	NPC180183
0.8818	High Similarity	NPC476539
0.8818	High Similarity	NPC6931
0.8818	High Similarity	NPC476540
0.8818	High Similarity	NPC476541
0.8807	High Similarity	NPC242748
0.8807	High Similarity	NPC309448
0.8807	High Similarity	NPC181845
0.8796	High Similarity	NPC472252
0.8796	High Similarity	NPC16520
0.8796	High Similarity	NPC155010
0.8796	High Similarity	NPC189852
0.8796	High Similarity	NPC157659
0.8796	High Similarity	NPC131479
0.8796	High Similarity	NPC31907
0.8796	High Similarity	NPC473020
0.8796	High Similarity	NPC245280
0.8796	High Similarity	NPC120123
0.8796	High Similarity	NPC114874
0.8796	High Similarity	NPC8039
0.8796	High Similarity	NPC213190
0.8796	High Similarity	NPC211879
0.8796	High Similarity	NPC286969
0.8761	High Similarity	NPC79900
0.875	High Similarity	NPC13193
0.8739	High Similarity	NPC302057
0.8739	High Similarity	NPC476835
0.8727	High Similarity	NPC226642
0.8727	High Similarity	NPC94272
0.8716	High Similarity	NPC187400
0.8716	High Similarity	NPC221562
0.8716	High Similarity	NPC475365
0.8716	High Similarity	NPC273879
0.8716	High Similarity	NPC165033
0.8716	High Similarity	NPC470885
0.8704	High Similarity	NPC159036
0.8704	High Similarity	NPC312553
0.8704	High Similarity	NPC136816
0.8704	High Similarity	NPC288694
0.8684	High Similarity	NPC11548
0.8673	High Similarity	NPC112274
0.8673	High Similarity	NPC42171
0.8661	High Similarity	NPC141433
0.8649	High Similarity	NPC128123
0.8644	High Similarity	NPC43842
0.8636	High Similarity	NPC473923
0.8636	High Similarity	NPC26798
0.8636	High Similarity	NPC473476
0.8636	High Similarity	NPC474569
0.8624	High Similarity	NPC16573
0.8611	High Similarity	NPC4831
0.8611	High Similarity	NPC472023
0.8611	High Similarity	NPC47566
0.8611	High Similarity	NPC160734
0.8611	High Similarity	NPC309425
0.8611	High Similarity	NPC88000
0.8611	High Similarity	NPC129372
0.8609	High Similarity	NPC477029
0.8609	High Similarity	NPC477031
0.8609	High Similarity	NPC63609
0.8609	High Similarity	NPC477030
0.8596	High Similarity	NPC476546
0.8596	High Similarity	NPC144068
0.8596	High Similarity	NPC51154
0.8584	High Similarity	NPC472715
0.8584	High Similarity	NPC114188
0.8584	High Similarity	NPC13190
0.8584	High Similarity	NPC65167
0.8571	High Similarity	NPC106589
0.8571	High Similarity	NPC257207
0.8571	High Similarity	NPC295133
0.8571	High Similarity	NPC202261
0.8559	High Similarity	NPC231340
0.8545	High Similarity	NPC475521
0.8534	High Similarity	NPC477807
0.8522	High Similarity	NPC477808
0.8522	High Similarity	NPC208832
0.8519	High Similarity	NPC473200
0.8519	High Similarity	NPC7341
0.8509	High Similarity	NPC472716
0.8509	High Similarity	NPC475354
0.8509	High Similarity	NPC308140
0.8496	Intermediate Similarity	NPC472717
0.8482	Intermediate Similarity	NPC472988
0.8482	Intermediate Similarity	NPC472896
0.8482	Intermediate Similarity	NPC49032
0.8482	Intermediate Similarity	NPC51172
0.8482	Intermediate Similarity	NPC472897
0.8482	Intermediate Similarity	NPC38217
0.8482	Intermediate Similarity	NPC125324
0.8475	Intermediate Similarity	NPC476670
0.8468	Intermediate Similarity	NPC472900
0.8468	Intermediate Similarity	NPC472899
0.8468	Intermediate Similarity	NPC472898
0.8455	Intermediate Similarity	NPC473198
0.8455	Intermediate Similarity	NPC475701
0.8448	Intermediate Similarity	NPC148965
0.8435	Intermediate Similarity	NPC469347
0.8435	Intermediate Similarity	NPC307642
0.8435	Intermediate Similarity	NPC469348
0.8426	Intermediate Similarity	NPC234287
0.8426	Intermediate Similarity	NPC280825
0.8421	Intermediate Similarity	NPC472987
0.8421	Intermediate Similarity	NPC92710
0.8421	Intermediate Similarity	NPC470748
0.8421	Intermediate Similarity	NPC473021
0.8407	Intermediate Similarity	NPC125361
0.8407	Intermediate Similarity	NPC51925
0.8407	Intermediate Similarity	NPC154085

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 NPC476691 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	2559
0.2-0.3	4399
0.3-0.4	1237
0.4-0.5	371
0.5-0.6	245
0.6-0.7	40
0.7-0.8	12
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8319	Intermediate Similarity	NPD8377	Approved
0.8319	Intermediate Similarity	NPD8294	Approved
0.825	Intermediate Similarity	NPD8033	Approved
0.825	Intermediate Similarity	NPD8296	Approved
0.825	Intermediate Similarity	NPD8380	Approved
0.825	Intermediate Similarity	NPD8379	Approved
0.825	Intermediate Similarity	NPD8378	Approved
0.825	Intermediate Similarity	NPD8335	Approved
0.7963	Intermediate Similarity	NPD8171	Discontinued
0.7851	Intermediate Similarity	NPD7328	Approved
0.7851	Intermediate Similarity	NPD7327	Approved
0.7787	Intermediate Similarity	NPD7516	Approved
0.7667	Intermediate Similarity	NPD8133	Approved
0.7424	Intermediate Similarity	NPD8450	Suspended
0.7422	Intermediate Similarity	NPD7507	Approved
0.7381	Intermediate Similarity	NPD7503	Approved
0.7348	Intermediate Similarity	NPD8449	Approved
0.7311	Intermediate Similarity	NPD6412	Phase 2
0.7288	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD7319	Approved
0.7176	Intermediate Similarity	NPD7736	Approved
0.7054	Intermediate Similarity	NPD6370	Approved
0.7	Intermediate Similarity	NPD8328	Phase 3
0.697	Remote Similarity	NPD8293	Discontinued
0.6929	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6054	Approved
0.6899	Remote Similarity	NPD6059	Approved
0.6852	Remote Similarity	NPD6928	Phase 2
0.6852	Remote Similarity	NPD7525	Registered
0.6806	Remote Similarity	NPD7625	Phase 1
0.6742	Remote Similarity	NPD6067	Discontinued
0.6718	Remote Similarity	NPD6016	Approved
0.6718	Remote Similarity	NPD6015	Approved
0.6716	Remote Similarity	NPD7078	Approved
0.6692	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6642	Remote Similarity	NPD6616	Approved
0.6591	Remote Similarity	NPD8515	Approved
0.6591	Remote Similarity	NPD8513	Phase 3
0.6591	Remote Similarity	NPD8517	Approved
0.6591	Remote Similarity	NPD8516	Approved
0.6579	Remote Similarity	NPD7524	Approved
0.656	Remote Similarity	NPD6686	Approved
0.6484	Remote Similarity	NPD6882	Approved
0.6484	Remote Similarity	NPD8297	Approved
0.646	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7645	Phase 2
0.6446	Remote Similarity	NPD7638	Approved
0.6423	Remote Similarity	NPD6033	Approved
0.6412	Remote Similarity	NPD6009	Approved
0.6393	Remote Similarity	NPD7639	Approved
0.6393	Remote Similarity	NPD7640	Approved
0.6391	Remote Similarity	NPD6319	Approved
0.6372	Remote Similarity	NPD6695	Phase 3
0.633	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD4632	Approved
0.6299	Remote Similarity	NPD7320	Approved
0.6293	Remote Similarity	NPD7750	Discontinued
0.6293	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.627	Remote Similarity	NPD5739	Approved
0.627	Remote Similarity	NPD6402	Approved
0.627	Remote Similarity	NPD6675	Approved
0.627	Remote Similarity	NPD6008	Approved
0.627	Remote Similarity	NPD7128	Approved
0.625	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD6372	Approved
0.6239	Remote Similarity	NPD6942	Approved
0.6239	Remote Similarity	NPD7339	Approved
0.6198	Remote Similarity	NPD7991	Discontinued
0.6182	Remote Similarity	NPD6933	Approved
0.6172	Remote Similarity	NPD6881	Approved
0.6172	Remote Similarity	NPD6899	Approved
0.6154	Remote Similarity	NPD6650	Approved
0.6154	Remote Similarity	NPD8130	Phase 1
0.6154	Remote Similarity	NPD6649	Approved
0.6106	Remote Similarity	NPD6930	Phase 2
0.6106	Remote Similarity	NPD6931	Approved
0.6098	Remote Similarity	NPD4755	Approved
0.6094	Remote Similarity	NPD5697	Approved
0.6094	Remote Similarity	NPD5701	Approved
0.6083	Remote Similarity	NPD8034	Phase 2
0.6083	Remote Similarity	NPD8035	Phase 2
0.6077	Remote Similarity	NPD7290	Approved
0.6077	Remote Similarity	NPD7102	Approved
0.6077	Remote Similarity	NPD6883	Approved
0.6077	Remote Similarity	NPD4634	Approved
0.6045	Remote Similarity	NPD7115	Discovery
0.6033	Remote Similarity	NPD6399	Phase 3
0.6033	Remote Similarity	NPD4202	Approved
0.6031	Remote Similarity	NPD6847	Approved
0.6031	Remote Similarity	NPD6617	Approved
0.6031	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD6869	Approved
0.6018	Remote Similarity	NPD6929	Approved
0.6014	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD6014	Approved
0.6	Remote Similarity	NPD4784	Approved
0.6	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD6924	Approved
0.6	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD4785	Approved
0.6	Remote Similarity	NPD6926	Approved
0.6	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD4700	Approved
0.6	Remote Similarity	NPD5285	Approved
0.6	Remote Similarity	NPD6012	Approved
0.5986	Remote Similarity	NPD5956	Approved
0.5985	Remote Similarity	NPD5983	Phase 2
0.5984	Remote Similarity	NPD7748	Approved
0.5982	Remote Similarity	NPD6932	Approved
0.5968	Remote Similarity	NPD6083	Phase 2
0.5968	Remote Similarity	NPD7902	Approved
0.5968	Remote Similarity	NPD6084	Phase 2
0.5965	Remote Similarity	NPD4748	Discontinued
0.5963	Remote Similarity	NPD4243	Approved
0.5952	Remote Similarity	NPD4159	Approved
0.595	Remote Similarity	NPD7087	Discontinued
0.5929	Remote Similarity	NPD6336	Discontinued
0.5926	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5923	Remote Similarity	NPD6011	Approved
0.592	Remote Similarity	NPD4225	Approved
0.5906	Remote Similarity	NPD5211	Phase 2
0.5906	Remote Similarity	NPD4633	Approved
0.5906	Remote Similarity	NPD5225	Approved
0.5906	Remote Similarity	NPD5226	Approved
0.5906	Remote Similarity	NPD7632	Discontinued
0.5906	Remote Similarity	NPD5224	Approved
0.5897	Remote Similarity	NPD3668	Phase 3
0.5897	Remote Similarity	NPD4786	Approved
0.5891	Remote Similarity	NPD4768	Approved
0.5891	Remote Similarity	NPD4767	Approved
0.5877	Remote Similarity	NPD6683	Phase 2
0.5868	Remote Similarity	NPD3168	Discontinued
0.5859	Remote Similarity	NPD5174	Approved
0.5859	Remote Similarity	NPD4754	Approved
0.5859	Remote Similarity	NPD5175	Approved
0.5856	Remote Similarity	NPD1811	Approved
0.5856	Remote Similarity	NPD1810	Approved
0.5847	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6893	Approved
0.5841	Remote Similarity	NPD5776	Phase 2
0.5841	Remote Similarity	NPD6925	Approved
0.5827	Remote Similarity	NPD5223	Approved
0.5826	Remote Similarity	NPD7514	Phase 3
0.5826	Remote Similarity	NPD7509	Discontinued
0.582	Remote Similarity	NPD7515	Phase 2
0.5814	Remote Similarity	NPD5141	Approved
0.5806	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD4730	Approved
0.5802	Remote Similarity	NPD4729	Approved
0.5789	Remote Similarity	NPD7145	Approved
0.5785	Remote Similarity	NPD4753	Phase 2
0.5785	Remote Similarity	NPD5328	Approved
0.5785	Remote Similarity	NPD6051	Approved
0.5775	Remote Similarity	NPD8074	Phase 3
0.5758	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5746	Remote Similarity	NPD6053	Discontinued
0.5735	Remote Similarity	NPD6274	Approved
0.5726	Remote Similarity	NPD3667	Approved
0.5726	Remote Similarity	NPD7900	Approved
0.5726	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD7101	Approved
0.5725	Remote Similarity	NPD7100	Approved
0.5714	Remote Similarity	NPD5250	Approved
0.5714	Remote Similarity	NPD5247	Approved
0.5714	Remote Similarity	NPD5249	Phase 3
0.5714	Remote Similarity	NPD5251	Approved
0.5714	Remote Similarity	NPD5248	Approved
0.5703	Remote Similarity	NPD5344	Discontinued
0.5702	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5693	Remote Similarity	NPD6317	Approved
0.5691	Remote Similarity	NPD6079	Approved
0.5691	Remote Similarity	NPD7637	Suspended
0.569	Remote Similarity	NPD7332	Phase 2
0.5682	Remote Similarity	NPD5128	Approved
0.5682	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.568	Remote Similarity	NPD5695	Phase 3
0.568	Remote Similarity	NPD7799	Discontinued
0.5676	Remote Similarity	NPD7151	Approved
0.5676	Remote Similarity	NPD7150	Approved
0.5676	Remote Similarity	NPD7152	Approved
0.5669	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD5696	Approved
0.5667	Remote Similarity	NPD3618	Phase 1
0.5664	Remote Similarity	NPD5275	Approved
0.5664	Remote Similarity	NPD4190	Phase 3
0.5652	Remote Similarity	NPD6335	Approved
0.5643	Remote Similarity	NPD6908	Approved
0.5643	Remote Similarity	NPD6909	Approved
0.5641	Remote Similarity	NPD6902	Approved
0.5641	Remote Similarity	NPD6898	Phase 1
0.5636	Remote Similarity	NPD6922	Approved
0.5636	Remote Similarity	NPD6923	Approved
0.563	Remote Similarity	NPD3133	Approved
0.563	Remote Similarity	NPD3665	Phase 1
0.563	Remote Similarity	NPD3666	Approved
0.5625	Remote Similarity	NPD8336	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