NPASS Compound

Structure

NPC470434 OpenBabel07101719132D 42 46 0 0 1 0 0 0 0 0999 V2000 12.4610 3.3975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4536 5.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1009 5.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5191 5.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5215 3.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4828 3.1896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1664 4.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8356 3.7248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4670 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1227 4.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1883 4.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.8137 3.9328 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8793 3.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 34 1 0 0 0 0 6 35 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 34 1 0 0 0 0 15 35 1 0 0 0 0 16 22 1 0 0 0 0 16 23 1 0 0 0 0 17 22 2 0 0 0 0 17 27 1 0 0 0 0 18 36 1 0 0 0 0 19 21 1 0 0 0 0 20 4 1 6 0 0 0 20 24 1 0 0 0 0 21 7 1 6 0 0 0 22 34 1 0 0 0 0 23 41 1 1 0 0 0 24 35 1 1 0 0 0 25 29 1 0 0 0 0 25 35 1 1 0 0 0 26 29 1 0 0 0 0 26 34 1 1 0 0 0 27 29 1 0 0 0 0 27 37 1 0 0 0 0 28 18 1 6 0 0 0 28 30 1 0 0 0 0 28 42 1 0 0 0 0 30 31 1 0 0 0 0 30 38 1 0 0 0 0 31 32 1 0 0 0 0 31 39 1 0 0 0 0 32 33 1 0 0 0 0 32 40 1 0 0 0 0 33 41 1 0 0 0 0 33 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	592.43
Volume:	630.029
LogP:	5.12
LogD:	5.018
LogS:	-4.151
# Rotatable Bonds:	9
TPSA:	119.61
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.244
Synthetic Accessibility Score:	5.166
Fsp3:	0.943
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:	-4.873
MDCK Permeability:	1.4587327314075083e-05
Pgp-inhibitor:	0.975
Pgp-substrate:	0.079
Human Intestinal Absorption (HIA):	0.107
20% Bioavailability (F20%):	0.662
30% Bioavailability (F30%):	0.067

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	92.46204376220703%
Volume Distribution (VD):	0.866
Pgp-substrate:	2.1582224369049072%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.368
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.813
CYP2C9-inhibitor:	0.098
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.182
CYP3A4-substrate:	0.322

ADMET: Excretion

Clearance (CL):	1.895
Half-life (T1/2):	0.19

ADMET: Toxicity

hERG Blockers:	0.424
Human Hepatotoxicity (H-HT):	0.187
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.438
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.927

Download Data

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

Natural Product: NPC470434

Natural Product ID:	NPC470434
*Common Name:**	7-Hydroxysitosterol-3-O-Beta-D-Glucopyranoside
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-7-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	CPVAKQVYNLPUBL-GKOHCLSJSA-N
Standard InCHI:	InChI=1S/C35H60O7/c1-7-21(19(2)3)9-8-20(4)24-10-11-25-29-26(13-15-35(24,25)6)34(5)14-12-23(16-22(34)17-27(29)37)41-33-32(40)31(39)30(38)28(18-36)42-33/h17,19-21,23-33,36-40H,7-16,18H2,1-6H3/t20-,21-,23+,24-,25+,26+,27?,28-,29+,30-,31+,32-,33-,34+,35-/m1/s1
SMILES:	CC[C@@H](C(C)C)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C(O)C=C2[C@]1(C)CC[C@@H](C2)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2036083
PubChem CID:	70683854
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes and derivatives

*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
NPO32523	solanum violaceum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22413887]
NPO32523	solanum violaceum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23511021]

☑ 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	6

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[480177]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[480177]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[480177]
NPT1031	Cell Line	Ca9-22	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[480177]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[480177]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20.0	ug.mL-1	PMID[480177]

☑ 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 NPC470434 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	220
0.1-0.2	1603
0.2-0.3	5004
0.3-0.4	12372
0.4-0.5	9819
0.5-0.6	6135
0.6-0.7	4794
0.7-0.8	2217
0.8-0.85	381
0.85-0.9	120
0.9-0.95	24
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9892	High Similarity	NPC469942
0.9688	High Similarity	NPC75608
0.9677	High Similarity	NPC473890
0.9677	High Similarity	NPC243728
0.9574	High Similarity	NPC158088
0.9485	High Similarity	NPC93352
0.9474	High Similarity	NPC282669
0.9388	High Similarity	NPC472900
0.9388	High Similarity	NPC472898
0.9388	High Similarity	NPC472899
0.9381	High Similarity	NPC473198
0.9375	High Similarity	NPC285231
0.9375	High Similarity	NPC267510
0.9375	High Similarity	NPC21568
0.9362	High Similarity	NPC207617
0.9293	High Similarity	NPC33053
0.9278	High Similarity	NPC272015
0.9208	High Similarity	NPC141433
0.9167	High Similarity	NPC234287
0.9167	High Similarity	NPC280825
0.91	High Similarity	NPC231340
0.9091	High Similarity	NPC187400
0.9091	High Similarity	NPC470885
0.9091	High Similarity	NPC221562
0.9082	High Similarity	NPC154452
0.9082	High Similarity	NPC136816
0.9072	High Similarity	NPC64348
0.9072	High Similarity	NPC7341
0.9072	High Similarity	NPC473200
0.901	High Similarity	NPC472896
0.901	High Similarity	NPC472897
0.9	High Similarity	NPC309448
0.9	High Similarity	NPC181845
0.9	High Similarity	NPC473476
0.9	High Similarity	NPC242748
0.9	High Similarity	NPC474569
0.9	High Similarity	NPC473923
0.898	High Similarity	NPC47566
0.898	High Similarity	NPC88000
0.898	High Similarity	NPC472023
0.898	High Similarity	NPC309425
0.898	High Similarity	NPC160734
0.898	High Similarity	NPC4831
0.898	High Similarity	NPC21064
0.898	High Similarity	NPC129372
0.898	High Similarity	NPC121072
0.8969	High Similarity	NPC476895
0.8942	High Similarity	NPC307642
0.8936	High Similarity	NPC302584
0.8922	High Similarity	NPC157530
0.8922	High Similarity	NPC472901
0.8922	High Similarity	NPC250089
0.8922	High Similarity	NPC14630
0.8911	High Similarity	NPC190395
0.8911	High Similarity	NPC226642
0.8911	High Similarity	NPC470432
0.8911	High Similarity	NPC305423
0.8911	High Similarity	NPC283829
0.8911	High Similarity	NPC14704
0.8911	High Similarity	NPC230507
0.8911	High Similarity	NPC113044
0.8911	High Similarity	NPC161676
0.8911	High Similarity	NPC94272
0.8889	High Similarity	NPC288694
0.8889	High Similarity	NPC312553
0.8889	High Similarity	NPC159036
0.8866	High Similarity	NPC240372
0.8866	High Similarity	NPC476893
0.8854	High Similarity	NPC476894
0.8846	High Similarity	NPC473567
0.8846	High Similarity	NPC216595
0.8835	High Similarity	NPC191439
0.8835	High Similarity	NPC65155
0.8835	High Similarity	NPC103627
0.8835	High Similarity	NPC170974
0.8824	High Similarity	NPC476538
0.8824	High Similarity	NPC476539
0.8824	High Similarity	NPC476540
0.8824	High Similarity	NPC476541
0.8824	High Similarity	NPC98696
0.8824	High Similarity	NPC295980
0.8824	High Similarity	NPC295389
0.8812	High Similarity	NPC26798
0.88	High Similarity	NPC162354
0.88	High Similarity	NPC189852
0.88	High Similarity	NPC8039
0.88	High Similarity	NPC157659
0.88	High Similarity	NPC211879
0.88	High Similarity	NPC31907
0.88	High Similarity	NPC245280
0.88	High Similarity	NPC114874
0.88	High Similarity	NPC16573
0.88	High Similarity	NPC155010
0.88	High Similarity	NPC213190
0.88	High Similarity	NPC473020
0.88	High Similarity	NPC286969
0.88	High Similarity	NPC472252
0.88	High Similarity	NPC131479
0.88	High Similarity	NPC16520
0.88	High Similarity	NPC120123
0.8788	High Similarity	NPC476896
0.8776	High Similarity	NPC5358
0.8776	High Similarity	NPC216260
0.8774	High Similarity	NPC146652
0.8763	High Similarity	NPC90583
0.8762	High Similarity	NPC51154
0.875	High Similarity	NPC305160
0.875	High Similarity	NPC473021
0.875	High Similarity	NPC72817
0.875	High Similarity	NPC477927
0.875	High Similarity	NPC65034
0.875	High Similarity	NPC208189
0.875	High Similarity	NPC13190
0.875	High Similarity	NPC472987
0.8738	High Similarity	NPC249265
0.8738	High Similarity	NPC70204
0.8738	High Similarity	NPC477809
0.8738	High Similarity	NPC150372
0.8738	High Similarity	NPC475670
0.8738	High Similarity	NPC309278
0.8738	High Similarity	NPC46190
0.8738	High Similarity	NPC208383
0.8738	High Similarity	NPC232054
0.8738	High Similarity	NPC470433
0.8738	High Similarity	NPC475333
0.8738	High Similarity	NPC6806
0.8738	High Similarity	NPC95051
0.8738	High Similarity	NPC302057
0.8738	High Similarity	NPC42482
0.8738	High Similarity	NPC475550
0.8738	High Similarity	NPC244086
0.8738	High Similarity	NPC22779
0.8738	High Similarity	NPC73243
0.8738	High Similarity	NPC306131
0.8738	High Similarity	NPC40440
0.8738	High Similarity	NPC473328
0.8738	High Similarity	NPC473318
0.8738	High Similarity	NPC248746
0.8738	High Similarity	NPC224098
0.8738	High Similarity	NPC477026
0.8738	High Similarity	NPC477027
0.8738	High Similarity	NPC300557
0.8738	High Similarity	NPC171073
0.8738	High Similarity	NPC28844
0.8738	High Similarity	NPC84956
0.8738	High Similarity	NPC102016
0.8738	High Similarity	NPC194207
0.8738	High Similarity	NPC218571
0.8725	High Similarity	NPC473469
0.8713	High Similarity	NPC165033
0.8713	High Similarity	NPC470768
0.8713	High Similarity	NPC273879
0.8687	High Similarity	NPC91497
0.8667	High Similarity	NPC477050
0.8667	High Similarity	NPC231797
0.8667	High Similarity	NPC42171
0.8667	High Similarity	NPC112274
0.8654	High Similarity	NPC87998
0.8654	High Similarity	NPC269297
0.8654	High Similarity	NPC247037
0.8654	High Similarity	NPC222202
0.8654	High Similarity	NPC154856
0.8654	High Similarity	NPC23808
0.8654	High Similarity	NPC477811
0.8654	High Similarity	NPC224314
0.8654	High Similarity	NPC472717
0.8654	High Similarity	NPC52241
0.8654	High Similarity	NPC475317
0.8641	High Similarity	NPC7213
0.8641	High Similarity	NPC235824
0.8632	High Similarity	NPC159876
0.8627	High Similarity	NPC269627
0.8627	High Similarity	NPC127801
0.8627	High Similarity	NPC208477
0.8627	High Similarity	NPC208594
0.8627	High Similarity	NPC194842
0.8627	High Similarity	NPC152584
0.8627	High Similarity	NPC69737
0.8627	High Similarity	NPC160816
0.8627	High Similarity	NPC473199
0.8614	High Similarity	NPC473124
0.8614	High Similarity	NPC473123
0.8614	High Similarity	NPC475701
0.8598	High Similarity	NPC207637
0.8571	High Similarity	NPC114188
0.8571	High Similarity	NPC472989
0.8571	High Similarity	NPC470748
0.8571	High Similarity	NPC477032
0.8571	High Similarity	NPC475247
0.8571	High Similarity	NPC472715
0.8571	High Similarity	NPC13193
0.8571	High Similarity	NPC477028
0.8571	High Similarity	NPC294129
0.8571	High Similarity	NPC476547
0.8571	High Similarity	NPC124677
0.8571	High Similarity	NPC197231
0.8558	High Similarity	NPC246205
0.8544	High Similarity	NPC234160
0.8544	High Similarity	NPC63368
0.8544	High Similarity	NPC208650

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 NPC470434 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	1745
0.2-0.3	4124
0.3-0.4	2052
0.4-0.5	568
0.5-0.6	266
0.6-0.7	163
0.7-0.8	38
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.819	Intermediate Similarity	NPD6412	Phase 2
0.8053	Intermediate Similarity	NPD8033	Approved
0.7965	Intermediate Similarity	NPD8377	Approved
0.7965	Intermediate Similarity	NPD8294	Approved
0.7946	Intermediate Similarity	NPD7327	Approved
0.7946	Intermediate Similarity	NPD7328	Approved
0.7895	Intermediate Similarity	NPD8380	Approved
0.7895	Intermediate Similarity	NPD8379	Approved
0.7895	Intermediate Similarity	NPD8378	Approved
0.7895	Intermediate Similarity	NPD8296	Approved
0.7895	Intermediate Similarity	NPD8335	Approved
0.7876	Intermediate Similarity	NPD7516	Approved
0.7755	Intermediate Similarity	NPD7524	Approved
0.7739	Intermediate Similarity	NPD7503	Approved
0.7629	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD6686	Approved
0.7526	Intermediate Similarity	NPD6695	Phase 3
0.7479	Intermediate Similarity	NPD7507	Approved
0.7434	Intermediate Similarity	NPD8133	Approved
0.7419	Intermediate Similarity	NPD6942	Approved
0.7419	Intermediate Similarity	NPD7339	Approved
0.74	Intermediate Similarity	NPD7750	Discontinued
0.74	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD8171	Discontinued
0.7295	Intermediate Similarity	NPD7319	Approved
0.7292	Intermediate Similarity	NPD6929	Approved
0.7258	Intermediate Similarity	NPD8449	Approved
0.7216	Intermediate Similarity	NPD7525	Registered
0.7216	Intermediate Similarity	NPD6931	Approved
0.7216	Intermediate Similarity	NPD6930	Phase 2
0.72	Intermediate Similarity	NPD8450	Suspended
0.7158	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7640	Approved
0.713	Intermediate Similarity	NPD7639	Approved
0.7094	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6370	Approved
0.7083	Intermediate Similarity	NPD5776	Phase 2
0.7083	Intermediate Similarity	NPD6925	Approved
0.7073	Intermediate Similarity	NPD7736	Approved
0.7048	Intermediate Similarity	NPD6399	Phase 3
0.7041	Intermediate Similarity	NPD7514	Phase 3
0.7037	Intermediate Similarity	NPD7638	Approved
0.7025	Intermediate Similarity	NPD8328	Phase 3
0.701	Intermediate Similarity	NPD7145	Approved
0.6992	Remote Similarity	NPD8293	Discontinued
0.6979	Remote Similarity	NPD6933	Approved
0.697	Remote Similarity	NPD6902	Approved
0.6952	Remote Similarity	NPD7087	Discontinued
0.6952	Remote Similarity	NPD7637	Suspended
0.6949	Remote Similarity	NPD7115	Discovery
0.6939	Remote Similarity	NPD7645	Phase 2
0.6931	Remote Similarity	NPD4786	Approved
0.6917	Remote Similarity	NPD6059	Approved
0.6917	Remote Similarity	NPD6054	Approved
0.6869	Remote Similarity	NPD7332	Phase 2
0.6869	Remote Similarity	NPD6928	Phase 2
0.6863	Remote Similarity	NPD6893	Approved
0.686	Remote Similarity	NPD8516	Approved
0.686	Remote Similarity	NPD8517	Approved
0.686	Remote Similarity	NPD8515	Approved
0.686	Remote Similarity	NPD8513	Phase 3
0.6771	Remote Similarity	NPD6926	Approved
0.6771	Remote Similarity	NPD6924	Approved
0.6748	Remote Similarity	NPD6067	Discontinued
0.6735	Remote Similarity	NPD6932	Approved
0.6733	Remote Similarity	NPD3667	Approved
0.6727	Remote Similarity	NPD4225	Approved
0.6726	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6015	Approved
0.6721	Remote Similarity	NPD6016	Approved
0.6694	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.664	Remote Similarity	NPD6616	Approved
0.6634	Remote Similarity	NPD6898	Phase 1
0.661	Remote Similarity	NPD6882	Approved
0.661	Remote Similarity	NPD8297	Approved
0.6604	Remote Similarity	NPD6051	Approved
0.6602	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6683	Phase 2
0.6598	Remote Similarity	NPD4784	Approved
0.6598	Remote Similarity	NPD4785	Approved
0.6587	Remote Similarity	NPD7078	Approved
0.6562	Remote Similarity	NPD7150	Approved
0.6562	Remote Similarity	NPD7151	Approved
0.6562	Remote Similarity	NPD4243	Approved
0.6562	Remote Similarity	NPD7152	Approved
0.6555	Remote Similarity	NPD4632	Approved
0.6549	Remote Similarity	NPD7632	Discontinued
0.6531	Remote Similarity	NPD8264	Approved
0.6526	Remote Similarity	NPD6922	Approved
0.6526	Remote Similarity	NPD6923	Approved
0.6522	Remote Similarity	NPD6402	Approved
0.6522	Remote Similarity	NPD6640	Phase 3
0.6522	Remote Similarity	NPD5739	Approved
0.6522	Remote Similarity	NPD7128	Approved
0.6522	Remote Similarity	NPD6675	Approved
0.6504	Remote Similarity	NPD6319	Approved
0.65	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6084	Phase 2
0.6486	Remote Similarity	NPD6083	Phase 2
0.6481	Remote Similarity	NPD8035	Phase 2
0.6481	Remote Similarity	NPD8034	Phase 2
0.646	Remote Similarity	NPD4159	Approved
0.646	Remote Similarity	NPD5344	Discontinued
0.6458	Remote Similarity	NPD7143	Approved
0.6458	Remote Similarity	NPD7144	Approved
0.6449	Remote Similarity	NPD5328	Approved
0.6429	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6881	Approved
0.641	Remote Similarity	NPD7320	Approved
0.641	Remote Similarity	NPD6899	Approved
0.6406	Remote Similarity	NPD6033	Approved
0.6404	Remote Similarity	NPD5211	Phase 2
0.6387	Remote Similarity	NPD8130	Phase 1
0.6373	Remote Similarity	NPD7509	Discontinued
0.6373	Remote Similarity	NPD4748	Discontinued
0.6364	Remote Similarity	NPD7748	Approved
0.6356	Remote Similarity	NPD6372	Approved
0.6356	Remote Similarity	NPD6373	Approved
0.6339	Remote Similarity	NPD7902	Approved
0.6339	Remote Similarity	NPD4755	Approved
0.6333	Remote Similarity	NPD6053	Discontinued
0.6331	Remote Similarity	NPD7625	Phase 1
0.633	Remote Similarity	NPD6079	Approved
0.6325	Remote Similarity	NPD5701	Approved
0.6325	Remote Similarity	NPD5697	Approved
0.6321	Remote Similarity	NPD3618	Phase 1
0.6303	Remote Similarity	NPD6883	Approved
0.6303	Remote Similarity	NPD4634	Approved
0.6303	Remote Similarity	NPD7102	Approved
0.6303	Remote Similarity	NPD7290	Approved
0.6296	Remote Similarity	NPD4753	Phase 2
0.6293	Remote Similarity	NPD5141	Approved
0.6286	Remote Similarity	NPD3668	Phase 3
0.6286	Remote Similarity	NPD3133	Approved
0.6286	Remote Similarity	NPD3665	Phase 1
0.6286	Remote Similarity	NPD3666	Approved
0.6273	Remote Similarity	NPD4202	Approved
0.627	Remote Similarity	NPD5125	Phase 3
0.627	Remote Similarity	NPD5126	Approved
0.625	Remote Similarity	NPD6649	Approved
0.625	Remote Similarity	NPD6847	Approved
0.625	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD6869	Approved
0.625	Remote Similarity	NPD6650	Approved
0.624	Remote Similarity	NPD7741	Discontinued
0.6239	Remote Similarity	NPD3168	Discontinued
0.6239	Remote Similarity	NPD6698	Approved
0.6239	Remote Similarity	NPD7838	Discovery
0.6239	Remote Similarity	NPD46	Approved
0.6239	Remote Similarity	NPD6008	Approved
0.6239	Remote Similarity	NPD7136	Phase 2
0.6228	Remote Similarity	NPD5286	Approved
0.6228	Remote Similarity	NPD4700	Approved
0.6228	Remote Similarity	NPD4696	Approved
0.6228	Remote Similarity	NPD5285	Approved
0.6226	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7604	Phase 2
0.6218	Remote Similarity	NPD6013	Approved
0.6218	Remote Similarity	NPD6014	Approved
0.6218	Remote Similarity	NPD6012	Approved
0.6204	Remote Similarity	NPD6672	Approved
0.6204	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5737	Approved
0.6202	Remote Similarity	NPD8074	Phase 3
0.62	Remote Similarity	NPD4190	Phase 3
0.62	Remote Similarity	NPD5275	Approved
0.619	Remote Similarity	NPD5983	Phase 2
0.6186	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD5956	Approved
0.6182	Remote Similarity	NPD7515	Phase 2
0.6182	Remote Similarity	NPD7983	Approved
0.6168	Remote Similarity	NPD7334	Approved
0.6168	Remote Similarity	NPD6684	Approved
0.6168	Remote Similarity	NPD7146	Approved
0.6168	Remote Similarity	NPD5330	Approved
0.6168	Remote Similarity	NPD7521	Approved
0.6168	Remote Similarity	NPD6409	Approved
0.6167	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7991	Discontinued
0.6161	Remote Similarity	NPD5695	Phase 3
0.614	Remote Similarity	NPD5696	Approved
0.6134	Remote Similarity	NPD6011	Approved
0.6134	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD5778	Approved
0.6126	Remote Similarity	NPD5779	Approved
0.6124	Remote Similarity	NPD6336	Discontinued
0.6121	Remote Similarity	NPD5224	Approved
0.6121	Remote Similarity	NPD4633	Approved
0.6121	Remote Similarity	NPD5226	Approved
0.6121	Remote Similarity	NPD5225	Approved
0.6117	Remote Similarity	NPD4195	Approved
0.6116	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4251	Approved
0.6111	Remote Similarity	NPD4250	Approved
0.6106	Remote Similarity	NPD5220	Clinical (unspecified phase)

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