NPASS Compound

Structure

NPC475354 OpenBabel07101719152D 45 49 0 0 1 0 0 0 0 0999 V2000 7.5917 -11.8688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4328 -10.5817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5032 -7.2871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4135 -6.2894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9680 -8.9344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9190 -9.2434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -4.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -5.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -8.2350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -5.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5154 -9.5013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3838 -10.8907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7601 -7.9562 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0000 -2.3660 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.8090 -7.6472 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0000 -4.0981 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.1910 -7.6472 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5000 -4.9641 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.3074 -8.5232 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.1270 -10.2215 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.5000 -4.9641 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.3564 -8.2141 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.6132 -8.8833 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.5000 -6.6962 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.8212 -9.8614 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.0000 -4.0981 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.5000 -6.6962 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.0000 -5.8301 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.2399 -7.9562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -4.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0506 -7.8540 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1485 -7.2360 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6622 -8.5743 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -6.6962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5000 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7722 -10.1704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0780 -10.5306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -1.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 30 1 0 0 0 0 5 31 1 0 0 0 0 6 7 2 0 0 0 0 6 17 1 0 0 0 0 7 24 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 25 1 0 0 0 0 10 30 1 0 0 0 0 11 31 1 0 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 14 32 1 0 0 0 0 15 23 1 0 0 0 0 15 42 1 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 18 44 1 0 0 0 0 19 31 1 0 0 0 0 20 22 1 0 0 0 0 20 30 1 0 0 0 0 21 28 1 0 0 0 0 21 33 1 0 0 0 0 22 34 1 0 0 0 0 23 26 1 0 0 0 0 23 35 1 0 0 0 0 24 43 1 0 0 0 0 25 30 1 0 0 0 0 25 32 1 0 0 0 0 26 27 1 0 0 0 0 26 36 1 0 0 0 0 27 29 1 0 0 0 0 27 37 1 0 0 0 0 28 31 1 0 0 0 0 28 32 1 0 0 0 0 29 42 1 0 0 0 0 29 43 1 0 0 0 0 32 38 1 0 0 0 0 39 45 1 0 0 0 0 40 45 2 0 0 0 0 41 45 2 0 0 0 0 44 45 1 0 0 0 0 M CHG 1 39 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	661.33
Volume:	639.283
LogP:	1.699
LogD:	1.0
LogS:	-2.963
# Rotatable Bonds:	8
TPSA:	206.27
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.123
Synthetic Accessibility Score:	5.926
Fsp3:	0.938
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.627
MDCK Permeability:	2.6320567485527135e-05
Pgp-inhibitor:	0.107
Pgp-substrate:	0.833
Human Intestinal Absorption (HIA):	0.303
20% Bioavailability (F20%):	0.052
30% Bioavailability (F30%):	0.786

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	81.66800689697266%
Volume Distribution (VD):	0.741
Pgp-substrate:	4.870621681213379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.427
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.055

ADMET: Excretion

Clearance (CL):	0.871
Half-life (T1/2):	0.122

ADMET: Toxicity

hERG Blockers:	0.223
Human Hepatotoxicity (H-HT):	0.329
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.356
Rat Oral Acute Toxicity:	0.605
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.702
Carcinogencity:	0.224
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC475354

Natural Product ID:	NPC475354
*Common Name:**	Minutoside A
IUPAC Name:	sodium;[(3S,5S,6S,8S,9R,10S,13R,14S,15R,17R)-6,8,15-trihydroxy-10,13-dimethyl-17-[(E,2R,5R)-6-methyl-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyhept-3-en-2-yl]-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] sulfate
Synonyms:
Standard InCHIKey:	MBFUPVKKRMTACS-VXQSHKTJSA-M
Standard InCHI:	InChI=1S/C32H54O12S.Na/c1-16(2)24(43-29-27(37)26(36)23(35)15-42-29)7-6-17(3)19-13-21(33)28-31(19,5)11-9-25-30(4)10-8-18(44-45(39,40)41)12-20(30)22(34)14-32(25,28)38;/h6-7,16-29,33-38H,8-15H2,1-5H3,(H,39,40,41);/q;+1/p-1/b7-6+;/t17-,18+,19-,20-,21-,22+,23-,24+,25-,26+,27-,28-,29+,30+,31-,32+;/m1./s1
SMILES:	CC([C@@H](O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O)/C=C/[C@H]([C@H]1C[C@H]([C@@H]2[C@]1(C)CC[C@H]1[C@@]2(O)C[C@@H]([C@@H]2[C@]1(C)CC[C@@H](C2)OS(=O)(=O)[O-])O)O)C)C.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503996
PubChem CID:	44559195
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal 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
NPO7694	Anasterias minuta	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11858747]
NPO7694	Anasterias minuta	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16124779]
NPO7694	Anasterias minuta	Species	n.a.	n.a.	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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	7.0	mm	PMID[505582]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	IZ	=	5.0	mm	PMID[505582]

☑ 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 NPC475354 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	279
0.1-0.2	2030
0.2-0.3	5946
0.3-0.4	12910
0.4-0.5	9929
0.5-0.6	5961
0.6-0.7	3528
0.7-0.8	1638
0.8-0.85	316
0.85-0.9	154
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9252	High Similarity	NPC216595
0.9252	High Similarity	NPC473567
0.9252	High Similarity	NPC475312
0.9151	High Similarity	NPC473328
0.9151	High Similarity	NPC473318
0.9151	High Similarity	NPC28844
0.9074	High Similarity	NPC477050
0.9065	High Similarity	NPC65155
0.9065	High Similarity	NPC170974
0.9065	High Similarity	NPC191439
0.9065	High Similarity	NPC103627
0.8972	High Similarity	NPC472901
0.8962	High Similarity	NPC33053
0.8952	High Similarity	NPC312774
0.8952	High Similarity	NPC475365
0.8899	High Similarity	NPC231797
0.8879	High Similarity	NPC472897
0.8879	High Similarity	NPC235824
0.8879	High Similarity	NPC472896
0.8868	High Similarity	NPC472899
0.8868	High Similarity	NPC472900
0.8868	High Similarity	NPC472898
0.8846	High Similarity	NPC309425
0.8846	High Similarity	NPC47566
0.8846	High Similarity	NPC4831
0.8846	High Similarity	NPC129372
0.8846	High Similarity	NPC160734
0.8846	High Similarity	NPC88000
0.8846	High Similarity	NPC472023
0.8807	High Similarity	NPC473021
0.8807	High Similarity	NPC208189
0.8807	High Similarity	NPC472987
0.8807	High Similarity	NPC65034
0.8785	High Similarity	NPC231340
0.8785	High Similarity	NPC473469
0.8774	High Similarity	NPC93352
0.8762	High Similarity	NPC136816
0.875	High Similarity	NPC474418
0.875	High Similarity	NPC93883
0.875	High Similarity	NPC87250
0.875	High Similarity	NPC157376
0.875	High Similarity	NPC142066
0.875	High Similarity	NPC471354
0.875	High Similarity	NPC243196
0.875	High Similarity	NPC471353
0.875	High Similarity	NPC34390
0.875	High Similarity	NPC100048
0.875	High Similarity	NPC244402
0.875	High Similarity	NPC196429
0.875	High Similarity	NPC473200
0.875	High Similarity	NPC471351
0.875	High Similarity	NPC158344
0.875	High Similarity	NPC309034
0.875	High Similarity	NPC471355
0.875	High Similarity	NPC50305
0.875	High Similarity	NPC99728
0.875	High Similarity	NPC20979
0.875	High Similarity	NPC77319
0.875	High Similarity	NPC84987
0.875	High Similarity	NPC473852
0.875	High Similarity	NPC7341
0.875	High Similarity	NPC27507
0.875	High Similarity	NPC476690
0.8716	High Similarity	NPC472717
0.8704	High Similarity	NPC80210
0.8704	High Similarity	NPC38376
0.8704	High Similarity	NPC475634
0.8684	High Similarity	NPC475556
0.8684	High Similarity	NPC475629
0.8679	High Similarity	NPC286969
0.8679	High Similarity	NPC131479
0.8679	High Similarity	NPC16520
0.8679	High Similarity	NPC31907
0.8679	High Similarity	NPC155010
0.8679	High Similarity	NPC472252
0.8679	High Similarity	NPC8039
0.8679	High Similarity	NPC157659
0.8679	High Similarity	NPC473020
0.8679	High Similarity	NPC473198
0.8679	High Similarity	NPC245280
0.8679	High Similarity	NPC211879
0.8679	High Similarity	NPC213190
0.8679	High Similarity	NPC189852
0.8679	High Similarity	NPC120123
0.8679	High Similarity	NPC114874
0.8673	High Similarity	NPC83287
0.8673	High Similarity	NPC10366
0.8667	High Similarity	NPC285231
0.8667	High Similarity	NPC21568
0.8661	High Similarity	NPC99620
0.8661	High Similarity	NPC193382
0.8661	High Similarity	NPC5311
0.8661	High Similarity	NPC310341
0.8661	High Similarity	NPC199428
0.8654	High Similarity	NPC234287
0.8654	High Similarity	NPC280825
0.8636	High Similarity	NPC472715
0.8636	High Similarity	NPC13190
0.8624	High Similarity	NPC195116
0.8624	High Similarity	NPC250089
0.8624	High Similarity	NPC14630
0.8624	High Similarity	NPC285253
0.8624	High Similarity	NPC221110
0.8624	High Similarity	NPC180459
0.8624	High Similarity	NPC157530
0.8624	High Similarity	NPC474573
0.8611	High Similarity	NPC226642
0.8609	High Similarity	NPC314535
0.8609	High Similarity	NPC173555
0.8598	High Similarity	NPC273879
0.8598	High Similarity	NPC75608
0.8598	High Similarity	NPC165033
0.8596	High Similarity	NPC5883
0.8596	High Similarity	NPC236973
0.8596	High Similarity	NPC55532
0.8596	High Similarity	NPC469756
0.8596	High Similarity	NPC30483
0.8596	High Similarity	NPC29639
0.8596	High Similarity	NPC44899
0.8596	High Similarity	NPC292467
0.8596	High Similarity	NPC470897
0.8596	High Similarity	NPC304260
0.8596	High Similarity	NPC32177
0.8585	High Similarity	NPC312553
0.8585	High Similarity	NPC37207
0.8585	High Similarity	NPC159036
0.8585	High Similarity	NPC288694
0.8584	High Similarity	NPC152615
0.8571	High Similarity	NPC69576
0.8571	High Similarity	NPC471633
0.8571	High Similarity	NPC31354
0.8571	High Similarity	NPC84949
0.8559	High Similarity	NPC112274
0.8559	High Similarity	NPC472716
0.8534	High Similarity	NPC264336
0.8532	High Similarity	NPC7213
0.8522	High Similarity	NPC474466
0.8522	High Similarity	NPC475136
0.8522	High Similarity	NPC72260
0.8519	High Similarity	NPC473476
0.8519	High Similarity	NPC473923
0.8519	High Similarity	NPC269627
0.8519	High Similarity	NPC160816
0.8519	High Similarity	NPC208477
0.8519	High Similarity	NPC127801
0.8519	High Similarity	NPC69737
0.8519	High Similarity	NPC242748
0.8519	High Similarity	NPC26798
0.8519	High Similarity	NPC473199
0.8519	High Similarity	NPC194842
0.8519	High Similarity	NPC152584
0.8519	High Similarity	NPC208594
0.8509	High Similarity	NPC476692
0.8509	High Similarity	NPC476691
0.8505	High Similarity	NPC473123
0.8505	High Similarity	NPC16573
0.8505	High Similarity	NPC471887
0.8505	High Similarity	NPC471886
0.8505	High Similarity	NPC471885
0.8505	High Similarity	NPC471888
0.8505	High Similarity	NPC473124
0.8482	Intermediate Similarity	NPC51154
0.8468	Intermediate Similarity	NPC110494
0.8468	Intermediate Similarity	NPC157474
0.8462	Intermediate Similarity	NPC208193
0.8462	Intermediate Similarity	NPC308262
0.8462	Intermediate Similarity	NPC117445
0.8462	Intermediate Similarity	NPC472989
0.8455	Intermediate Similarity	NPC128133
0.8448	Intermediate Similarity	NPC475590
0.8448	Intermediate Similarity	NPC474908
0.8448	Intermediate Similarity	NPC120390
0.8448	Intermediate Similarity	NPC40749
0.8448	Intermediate Similarity	NPC231518
0.8448	Intermediate Similarity	NPC475419
0.8448	Intermediate Similarity	NPC475219
0.8447	Intermediate Similarity	NPC473503
0.844	Intermediate Similarity	NPC181467
0.844	Intermediate Similarity	NPC14946
0.844	Intermediate Similarity	NPC63368
0.844	Intermediate Similarity	NPC208650
0.8435	Intermediate Similarity	NPC329905
0.8426	Intermediate Similarity	NPC470885
0.8426	Intermediate Similarity	NPC221562
0.8426	Intermediate Similarity	NPC187400
0.8426	Intermediate Similarity	NPC475521
0.8426	Intermediate Similarity	NPC110656
0.8426	Intermediate Similarity	NPC473127
0.8426	Intermediate Similarity	NPC203354
0.8421	Intermediate Similarity	NPC203862
0.8421	Intermediate Similarity	NPC290693
0.8411	Intermediate Similarity	NPC300399
0.8411	Intermediate Similarity	NPC471482
0.8407	Intermediate Similarity	NPC11548
0.8393	Intermediate Similarity	NPC473125
0.8393	Intermediate Similarity	NPC476305
0.8381	Intermediate Similarity	NPC477226
0.8376	Intermediate Similarity	NPC193893
0.8376	Intermediate Similarity	NPC474423
0.8376	Intermediate Similarity	NPC74259

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 NPC475354 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	2094
0.2-0.3	4191
0.3-0.4	1774
0.4-0.5	492
0.5-0.6	260
0.6-0.7	100
0.7-0.8	9
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
0.8673	High Similarity	NPD7328	Approved
0.8673	High Similarity	NPD7327	Approved
0.8609	High Similarity	NPD8379	Approved
0.8609	High Similarity	NPD8296	Approved
0.8609	High Similarity	NPD8378	Approved
0.8609	High Similarity	NPD8335	Approved
0.8609	High Similarity	NPD8380	Approved
0.8596	High Similarity	NPD7516	Approved
0.8522	High Similarity	NPD8377	Approved
0.8522	High Similarity	NPD8294	Approved
0.8448	Intermediate Similarity	NPD8033	Approved
0.8136	Intermediate Similarity	NPD7503	Approved
0.8017	Intermediate Similarity	NPD7507	Approved
0.7967	Intermediate Similarity	NPD7319	Approved
0.7692	Intermediate Similarity	NPD8133	Approved
0.75	Intermediate Similarity	NPD8171	Discontinued
0.7478	Intermediate Similarity	NPD6412	Phase 2
0.7265	Intermediate Similarity	NPD6686	Approved
0.7188	Intermediate Similarity	NPD7736	Approved
0.7168	Intermediate Similarity	NPD7638	Approved
0.7105	Intermediate Similarity	NPD7639	Approved
0.7105	Intermediate Similarity	NPD7640	Approved
0.7063	Intermediate Similarity	NPD6370	Approved
0.7019	Intermediate Similarity	NPD7525	Registered
0.6929	Remote Similarity	NPD7625	Phase 1
0.6917	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6054	Approved
0.6881	Remote Similarity	NPD7524	Approved
0.6864	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6928	Phase 2
0.6846	Remote Similarity	NPD8293	Discontinued
0.6772	Remote Similarity	NPD6059	Approved
0.6759	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6882	Approved
0.6748	Remote Similarity	NPD8297	Approved
0.6744	Remote Similarity	NPD8328	Phase 3
0.6719	Remote Similarity	NPD8517	Approved
0.6719	Remote Similarity	NPD6016	Approved
0.6719	Remote Similarity	NPD8515	Approved
0.6719	Remote Similarity	NPD8516	Approved
0.6719	Remote Similarity	NPD8513	Phase 3
0.6719	Remote Similarity	NPD6015	Approved
0.6716	Remote Similarity	NPD8449	Approved
0.6692	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD6695	Phase 3
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8450	Suspended
0.6641	Remote Similarity	NPD6319	Approved
0.6641	Remote Similarity	NPD6616	Approved
0.6615	Remote Similarity	NPD6067	Discontinued
0.661	Remote Similarity	NPD4159	Approved
0.6591	Remote Similarity	NPD7078	Approved
0.6577	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD7750	Discontinued
0.656	Remote Similarity	NPD4632	Approved
0.6557	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7632	Discontinued
0.6504	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5344	Discontinued
0.646	Remote Similarity	NPD6051	Approved
0.6449	Remote Similarity	NPD7645	Phase 2
0.6423	Remote Similarity	NPD6881	Approved
0.6423	Remote Similarity	NPD6899	Approved
0.64	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6649	Approved
0.64	Remote Similarity	NPD6650	Approved
0.64	Remote Similarity	NPD8130	Phase 1
0.6393	Remote Similarity	NPD6402	Approved
0.6393	Remote Similarity	NPD5739	Approved
0.6393	Remote Similarity	NPD6675	Approved
0.6393	Remote Similarity	NPD7128	Approved
0.6389	Remote Similarity	NPD6930	Phase 2
0.6389	Remote Similarity	NPD6931	Approved
0.6389	Remote Similarity	NPD7514	Phase 3
0.6371	Remote Similarity	NPD6373	Approved
0.6371	Remote Similarity	NPD6372	Approved
0.6341	Remote Similarity	NPD5697	Approved
0.6321	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7290	Approved
0.632	Remote Similarity	NPD6883	Approved
0.632	Remote Similarity	NPD4634	Approved
0.632	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7102	Approved
0.6303	Remote Similarity	NPD4225	Approved
0.6296	Remote Similarity	NPD6929	Approved
0.6296	Remote Similarity	NPD6033	Approved
0.629	Remote Similarity	NPD7320	Approved
0.6281	Remote Similarity	NPD5211	Phase 2
0.627	Remote Similarity	NPD6617	Approved
0.627	Remote Similarity	NPD6847	Approved
0.627	Remote Similarity	NPD6869	Approved
0.6262	Remote Similarity	NPD6932	Approved
0.625	Remote Similarity	NPD5286	Approved
0.625	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD4696	Approved
0.6241	Remote Similarity	NPD7604	Phase 2
0.624	Remote Similarity	NPD6012	Approved
0.624	Remote Similarity	NPD6014	Approved
0.624	Remote Similarity	NPD6013	Approved
0.6239	Remote Similarity	NPD7332	Phase 2
0.6226	Remote Similarity	NPD7339	Approved
0.6226	Remote Similarity	NPD6942	Approved
0.6218	Remote Similarity	NPD4755	Approved
0.6214	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD5983	Phase 2
0.621	Remote Similarity	NPD5701	Approved
0.6207	Remote Similarity	NPD7087	Discontinued
0.6207	Remote Similarity	NPD8035	Phase 2
0.6207	Remote Similarity	NPD8034	Phase 2
0.6207	Remote Similarity	NPD7637	Suspended
0.6204	Remote Similarity	NPD7145	Approved
0.6186	Remote Similarity	NPD7991	Discontinued
0.6182	Remote Similarity	NPD6902	Approved
0.6179	Remote Similarity	NPD5141	Approved
0.6168	Remote Similarity	NPD6933	Approved
0.6167	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.616	Remote Similarity	NPD6011	Approved
0.6154	Remote Similarity	NPD4202	Approved
0.6148	Remote Similarity	NPD5225	Approved
0.6148	Remote Similarity	NPD5226	Approved
0.6148	Remote Similarity	NPD4633	Approved
0.6148	Remote Similarity	NPD5224	Approved
0.6148	Remote Similarity	NPD6336	Discontinued
0.6142	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD7741	Discontinued
0.6132	Remote Similarity	NPD4784	Approved
0.6132	Remote Similarity	NPD4785	Approved
0.6116	Remote Similarity	NPD4700	Approved
0.6116	Remote Similarity	NPD6648	Approved
0.6111	Remote Similarity	NPD5776	Phase 2
0.6111	Remote Similarity	NPD6925	Approved
0.6106	Remote Similarity	NPD6893	Approved
0.6103	Remote Similarity	NPD8074	Phase 3
0.6098	Remote Similarity	NPD5174	Approved
0.6098	Remote Similarity	NPD5175	Approved
0.6095	Remote Similarity	NPD4243	Approved
0.6094	Remote Similarity	NPD6053	Discontinued
0.609	Remote Similarity	NPD6921	Approved
0.6083	Remote Similarity	NPD6084	Phase 2
0.6083	Remote Similarity	NPD6083	Phase 2
0.608	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD5223	Approved
0.6032	Remote Similarity	NPD4729	Approved
0.6032	Remote Similarity	NPD4730	Approved
0.6017	Remote Similarity	NPD6399	Phase 3
0.6	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD6640	Phase 3
0.6	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD6683	Phase 2
0.6	Remote Similarity	NPD4767	Approved
0.5983	Remote Similarity	NPD3168	Discontinued
0.5983	Remote Similarity	NPD7838	Discovery
0.5981	Remote Similarity	NPD1811	Approved
0.5981	Remote Similarity	NPD6926	Approved
0.5981	Remote Similarity	NPD1810	Approved
0.5981	Remote Similarity	NPD6924	Approved
0.5971	Remote Similarity	NPD5956	Approved
0.5968	Remote Similarity	NPD4754	Approved
0.5966	Remote Similarity	NPD7748	Approved
0.5965	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD7799	Discontinued
0.595	Remote Similarity	NPD7902	Approved
0.5946	Remote Similarity	NPD4748	Discontinued
0.594	Remote Similarity	NPD7100	Approved
0.594	Remote Similarity	NPD7101	Approved
0.5938	Remote Similarity	NPD5249	Phase 3
0.5938	Remote Similarity	NPD5247	Approved
0.5938	Remote Similarity	NPD5251	Approved
0.5938	Remote Similarity	NPD5248	Approved
0.5938	Remote Similarity	NPD5250	Approved
0.5932	Remote Similarity	NPD6079	Approved
0.5926	Remote Similarity	NPD5125	Phase 3
0.5926	Remote Similarity	NPD5126	Approved
0.5909	Remote Similarity	NPD6317	Approved
0.5897	Remote Similarity	NPD4753	Phase 2
0.5897	Remote Similarity	NPD5328	Approved
0.5893	Remote Similarity	NPD6898	Phase 1
0.5877	Remote Similarity	NPD4786	Approved
0.5865	Remote Similarity	NPD6335	Approved
0.5856	Remote Similarity	NPD4195	Approved
0.5847	Remote Similarity	NPD6698	Approved
0.5847	Remote Similarity	NPD46	Approved
0.5847	Remote Similarity	NPD7136	Phase 2
0.5833	Remote Similarity	NPD6940	Discontinued
0.5833	Remote Similarity	NPD6274	Approved
0.5827	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD5135	Approved
0.5814	Remote Similarity	NPD6371	Approved
0.5812	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD7509	Discontinued
0.5798	Remote Similarity	NPD7515	Phase 2
0.5794	Remote Similarity	NPD7150	Approved
0.5794	Remote Similarity	NPD7152	Approved
0.5794	Remote Similarity	NPD7151	Approved
0.5785	Remote Similarity	NPD4629	Approved
0.5785	Remote Similarity	NPD5210	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