NPASS Compound

Structure

NPC130792 OpenBabel07101718282D 33 36 0 0 1 0 0 0 0 0999 V2000 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1902 0.2750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2604 -2.6472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1264 -2.1472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1974 1.7549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2162 1.9481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4635 -0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1687 0.1738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3168 0.7620 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 2.7293 1.0747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3944 -1.1472 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4094 0.3417 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2604 -0.6472 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2604 -1.6472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 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 -2.5981 1.5000 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 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 14 1 0 0 0 0 5 26 1 0 0 0 0 6 26 1 0 0 0 0 7 27 1 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 12 27 1 0 0 0 0 13 14 2 0 0 0 0 13 19 1 0 0 0 0 15 3 1 1 0 0 0 15 20 1 0 0 0 0 16 4 1 6 0 0 0 16 22 1 0 0 0 0 16 31 1 0 0 0 0 17 20 1 0 0 0 0 17 27 1 1 0 0 0 18 11 1 6 0 0 0 18 21 1 0 0 0 0 18 26 1 0 0 0 0 19 28 2 0 0 0 0 19 32 1 0 0 0 0 20 21 1 0 0 0 0 21 26 1 0 0 0 0 22 23 1 0 0 0 0 22 29 1 0 0 0 0 23 24 1 0 0 0 0 23 30 1 0 0 0 0 24 25 1 0 0 0 0 24 32 1 0 0 0 0 25 31 1 0 0 0 0 25 33 1 0 0 0 0 27 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.31
Volume:	488.791
LogP:	5.966
LogD:	5.07
LogS:	-5.165
# Rotatable Bonds:	6
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.468
Synthetic Accessibility Score:	5.132
Fsp3:	0.889
Lipinski Rule-of-5:	Accepted
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:	-4.724
MDCK Permeability:	2.8536796889966354e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.944
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.386

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	92.72711181640625%
Volume Distribution (VD):	1.836
Pgp-substrate:	4.139472961425781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.181
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.782
CYP2C9-inhibitor:	0.166
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.261
CYP3A4-substrate:	0.413

ADMET: Excretion

Clearance (CL):	6.495
Half-life (T1/2):	0.448

ADMET: Toxicity

hERG Blockers:	0.349
Human Hepatotoxicity (H-HT):	0.278
Drug-inuced Liver Injury (DILI):	0.781
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.132
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.809
Carcinogencity:	0.062
Eye Corrosion:	0.149
Eye Irritation:	0.074
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC130792

Natural Product ID:	NPC130792
*Common Name:**	(Z)-((2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-Methyl-2-((1Ar,4R,4As,7R,7As,7Bs)-1,1,4,7-Tetramethyldecahydro-1H-Cyclopropa[E]Azulen-4-Yloxy)Tetrahydro-2H-Pyran-3-Yl)3-Methylpent-2-Enoate
IUPAC Name:	[(2S,3R,4S,5R,6R)-2-[[(1aR,4R,4aS,7R,7aS,7bS)-1,1,4,7-tetramethyl-2,3,4a,5,6,7,7a,7b-octahydro-1aH-cyclopropa[e]azulen-4-yl]oxy]-4,5-dihydroxy-6-methyloxan-3-yl] (Z)-3-methylpent-2-enoate
Synonyms:
Standard InCHIKey:	UQUYXFBISSCISA-IFPHDOPMSA-N
Standard InCHI:	InChI=1S/C27H44O6/c1-8-14(2)13-19(28)32-24-23(30)22(29)16(4)31-25(24)33-27(7)12-11-18-21(26(18,5)6)20-15(3)9-10-17(20)27/h13,15-18,20-25,29-30H,8-12H2,1-7H3/b14-13-/t15-,16-,17+,18-,20-,21-,22+,23+,24-,25+,27-/m1/s1
SMILES:	CC/C(=CC(=O)O[C@H]1[C@@H](O[C@@H]([C@@H]([C@@H]1O)O)C)O[C@]1(C)CC[C@@H]2[C@H]([C@H]3[C@@H]1CC[C@H]3C)C2(C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516857
PubChem CID:	44567061
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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
NPO17716	Calendula arvensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1965654]
NPO17716	Calendula arvensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17716	Calendula arvensis	Species	Asteraceae	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	7

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	Activity	=	22.0	%	PMID[523632]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	Activity	=	18.0	%	PMID[523632]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	Activity	=	5.0	%	PMID[523632]
NPT195	Organism	Vesicular stomatitis virus	Vesicular stomatitis virus	MIC50	>	20.0	ug.mL-1	PMID[523632]
NPT2517	Organism	Human rhinovirus 1B	Human rhinovirus 1B	Activity	=	0.0	%	PMID[523632]

☑ 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 NPC130792 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	202
0.1-0.2	1560
0.2-0.3	5561
0.3-0.4	13607
0.4-0.5	9113
0.5-0.6	7412
0.6-0.7	4554
0.7-0.8	674
0.8-0.85	12
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9362	High Similarity	NPC474182
0.8529	High Similarity	NPC85670
0.8333	Intermediate Similarity	NPC202886
0.8286	Intermediate Similarity	NPC257853
0.8229	Intermediate Similarity	NPC477748
0.8173	Intermediate Similarity	NPC239961
0.8152	Intermediate Similarity	NPC216941
0.8137	Intermediate Similarity	NPC198992
0.8091	Intermediate Similarity	NPC290693
0.8073	Intermediate Similarity	NPC471633
0.8073	Intermediate Similarity	NPC69576
0.8073	Intermediate Similarity	NPC84949
0.8073	Intermediate Similarity	NPC31354
0.8073	Intermediate Similarity	NPC106446
0.8065	Intermediate Similarity	NPC475849
0.8061	Intermediate Similarity	NPC477749
0.802	Intermediate Similarity	NPC155319
0.802	Intermediate Similarity	NPC96597
0.802	Intermediate Similarity	NPC309503
0.802	Intermediate Similarity	NPC239547
0.802	Intermediate Similarity	NPC91197
0.802	Intermediate Similarity	NPC125551
0.8018	Intermediate Similarity	NPC13710
0.8	Intermediate Similarity	NPC193382
0.8	Intermediate Similarity	NPC310341
0.8	Intermediate Similarity	NPC99620
0.8	Intermediate Similarity	NPC5311
0.8	Intermediate Similarity	NPC199428
0.7982	Intermediate Similarity	NPC287075
0.798	Intermediate Similarity	NPC472196
0.798	Intermediate Similarity	NPC238090
0.798	Intermediate Similarity	NPC472195
0.7979	Intermediate Similarity	NPC474266
0.7941	Intermediate Similarity	NPC472015
0.7928	Intermediate Similarity	NPC474418
0.7928	Intermediate Similarity	NPC471354
0.7928	Intermediate Similarity	NPC34390
0.7928	Intermediate Similarity	NPC158344
0.7928	Intermediate Similarity	NPC471355
0.7928	Intermediate Similarity	NPC157376
0.7928	Intermediate Similarity	NPC471351
0.7928	Intermediate Similarity	NPC203862
0.7928	Intermediate Similarity	NPC142066
0.7928	Intermediate Similarity	NPC196429
0.7928	Intermediate Similarity	NPC27507
0.7928	Intermediate Similarity	NPC243196
0.7928	Intermediate Similarity	NPC99728
0.7928	Intermediate Similarity	NPC77319
0.7928	Intermediate Similarity	NPC309034
0.7928	Intermediate Similarity	NPC473852
0.7928	Intermediate Similarity	NPC84987
0.7928	Intermediate Similarity	NPC152615
0.7928	Intermediate Similarity	NPC244402
0.7928	Intermediate Similarity	NPC93883
0.7928	Intermediate Similarity	NPC87250
0.7928	Intermediate Similarity	NPC50305
0.7928	Intermediate Similarity	NPC471353
0.7917	Intermediate Similarity	NPC311163
0.79	Intermediate Similarity	NPC159698
0.7895	Intermediate Similarity	NPC266718
0.7885	Intermediate Similarity	NPC121423
0.7864	Intermediate Similarity	NPC79631
0.7857	Intermediate Similarity	NPC83287
0.785	Intermediate Similarity	NPC177524
0.785	Intermediate Similarity	NPC392
0.785	Intermediate Similarity	NPC219900
0.7838	Intermediate Similarity	NPC207637
0.783	Intermediate Similarity	NPC82251
0.7822	Intermediate Similarity	NPC220221
0.7822	Intermediate Similarity	NPC240838
0.7812	Intermediate Similarity	NPC471494
0.7807	Intermediate Similarity	NPC470829
0.7807	Intermediate Similarity	NPC473228
0.78	Intermediate Similarity	NPC474835
0.7798	Intermediate Similarity	NPC470076
0.7798	Intermediate Similarity	NPC71680
0.7788	Intermediate Similarity	NPC268326
0.7788	Intermediate Similarity	NPC285231
0.7788	Intermediate Similarity	NPC280991
0.7788	Intermediate Similarity	NPC32177
0.7788	Intermediate Similarity	NPC470897
0.7788	Intermediate Similarity	NPC219038
0.7788	Intermediate Similarity	NPC29639
0.7788	Intermediate Similarity	NPC219656
0.7788	Intermediate Similarity	NPC153085
0.7788	Intermediate Similarity	NPC329905
0.7788	Intermediate Similarity	NPC55532
0.7788	Intermediate Similarity	NPC236973
0.7788	Intermediate Similarity	NPC21568
0.7788	Intermediate Similarity	NPC469756
0.7788	Intermediate Similarity	NPC292467
0.7788	Intermediate Similarity	NPC304260
0.7788	Intermediate Similarity	NPC30483
0.7788	Intermediate Similarity	NPC44899
0.7788	Intermediate Similarity	NPC5883
0.7778	Intermediate Similarity	NPC206618
0.7745	Intermediate Similarity	NPC98165
0.7739	Intermediate Similarity	NPC115349
0.7723	Intermediate Similarity	NPC256368
0.7719	Intermediate Similarity	NPC475136
0.7719	Intermediate Similarity	NPC475556
0.7719	Intermediate Similarity	NPC475629
0.7719	Intermediate Similarity	NPC474466
0.7719	Intermediate Similarity	NPC135369
0.7719	Intermediate Similarity	NPC72260
0.7717	Intermediate Similarity	NPC188793
0.7714	Intermediate Similarity	NPC470972
0.7714	Intermediate Similarity	NPC201191
0.7714	Intermediate Similarity	NPC154452
0.7714	Intermediate Similarity	NPC200672
0.7714	Intermediate Similarity	NPC471599
0.7714	Intermediate Similarity	NPC214714
0.7706	Intermediate Similarity	NPC15551
0.77	Intermediate Similarity	NPC235051
0.7699	Intermediate Similarity	NPC218093
0.7692	Intermediate Similarity	NPC244878
0.7692	Intermediate Similarity	NPC477721
0.7692	Intermediate Similarity	NPC477716
0.7685	Intermediate Similarity	NPC38948
0.767	Intermediate Similarity	NPC182811
0.767	Intermediate Similarity	NPC347923
0.767	Intermediate Similarity	NPC476057
0.7664	Intermediate Similarity	NPC93026
0.7664	Intermediate Similarity	NPC265502
0.7664	Intermediate Similarity	NPC29389
0.7664	Intermediate Similarity	NPC473199
0.7664	Intermediate Similarity	NPC469960
0.7652	Intermediate Similarity	NPC233500
0.7652	Intermediate Similarity	NPC475419
0.7652	Intermediate Similarity	NPC314535
0.7652	Intermediate Similarity	NPC475219
0.7652	Intermediate Similarity	NPC474908
0.7652	Intermediate Similarity	NPC475590
0.7652	Intermediate Similarity	NPC231518
0.7652	Intermediate Similarity	NPC120390
0.7652	Intermediate Similarity	NPC40749
0.7652	Intermediate Similarity	NPC173555
0.7647	Intermediate Similarity	NPC93869
0.7647	Intermediate Similarity	NPC6765
0.7632	Intermediate Similarity	NPC81222
0.7632	Intermediate Similarity	NPC291820
0.7624	Intermediate Similarity	NPC320089
0.7624	Intermediate Similarity	NPC474792
0.7624	Intermediate Similarity	NPC91654
0.7624	Intermediate Similarity	NPC67398
0.7619	Intermediate Similarity	NPC20673
0.7619	Intermediate Similarity	NPC477717
0.7619	Intermediate Similarity	NPC121072
0.7619	Intermediate Similarity	NPC26557
0.7619	Intermediate Similarity	NPC21064
0.7615	Intermediate Similarity	NPC472901
0.7604	Intermediate Similarity	NPC231601
0.76	Intermediate Similarity	NPC209816
0.7596	Intermediate Similarity	NPC274458
0.7596	Intermediate Similarity	NPC474957
0.7596	Intermediate Similarity	NPC151093
0.7596	Intermediate Similarity	NPC79449
0.7596	Intermediate Similarity	NPC65700
0.7593	Intermediate Similarity	NPC33053
0.7593	Intermediate Similarity	NPC472263
0.7593	Intermediate Similarity	NPC469957
0.7593	Intermediate Similarity	NPC469959
0.7593	Intermediate Similarity	NPC108682
0.7589	Intermediate Similarity	NPC216665
0.7586	Intermediate Similarity	NPC196130
0.7586	Intermediate Similarity	NPC264336
0.7586	Intermediate Similarity	NPC74259
0.7586	Intermediate Similarity	NPC474423
0.7586	Intermediate Similarity	NPC193893
0.7576	Intermediate Similarity	NPC248312
0.7573	Intermediate Similarity	NPC54731
0.757	Intermediate Similarity	NPC93352
0.757	Intermediate Similarity	NPC85593
0.757	Intermediate Similarity	NPC161775
0.757	Intermediate Similarity	NPC31430
0.7568	Intermediate Similarity	NPC241477
0.7565	Intermediate Similarity	NPC107607
0.7565	Intermediate Similarity	NPC470312
0.7549	Intermediate Similarity	NPC274588
0.7549	Intermediate Similarity	NPC472467
0.7549	Intermediate Similarity	NPC281775
0.7547	Intermediate Similarity	NPC252242
0.7547	Intermediate Similarity	NPC472815
0.7547	Intermediate Similarity	NPC475956
0.7545	Intermediate Similarity	NPC257240
0.7542	Intermediate Similarity	NPC222307
0.7526	Intermediate Similarity	NPC78673
0.7526	Intermediate Similarity	NPC160517
0.7526	Intermediate Similarity	NPC475035
0.7526	Intermediate Similarity	NPC186155
0.7525	Intermediate Similarity	NPC302584
0.7525	Intermediate Similarity	NPC249034
0.7524	Intermediate Similarity	NPC324841
0.7524	Intermediate Similarity	NPC469942
0.7523	Intermediate Similarity	NPC472988
0.7523	Intermediate Similarity	NPC38217
0.7522	Intermediate Similarity	NPC470075
0.7521	Intermediate Similarity	NPC308262
0.7521	Intermediate Similarity	NPC219804
0.7521	Intermediate Similarity	NPC117445

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 NPC130792 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1992
0.2-0.3	4100
0.3-0.4	2047
0.4-0.5	475
0.5-0.6	294
0.6-0.7	63
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7857	Intermediate Similarity	NPD7328	Approved
0.7857	Intermediate Similarity	NPD7327	Approved
0.785	Intermediate Similarity	NPD6686	Approved
0.7788	Intermediate Similarity	NPD7516	Approved
0.7719	Intermediate Similarity	NPD8294	Approved
0.7719	Intermediate Similarity	NPD8377	Approved
0.7652	Intermediate Similarity	NPD8380	Approved
0.7652	Intermediate Similarity	NPD8335	Approved
0.7652	Intermediate Similarity	NPD8296	Approved
0.7652	Intermediate Similarity	NPD8379	Approved
0.7652	Intermediate Similarity	NPD8378	Approved
0.7652	Intermediate Similarity	NPD7503	Approved
0.7652	Intermediate Similarity	NPD8033	Approved
0.7545	Intermediate Similarity	NPD6371	Approved
0.7426	Intermediate Similarity	NPD6698	Approved
0.7426	Intermediate Similarity	NPD46	Approved
0.7395	Intermediate Similarity	NPD7507	Approved
0.7273	Intermediate Similarity	NPD6412	Phase 2
0.7255	Intermediate Similarity	NPD7838	Discovery
0.7213	Intermediate Similarity	NPD7319	Approved
0.713	Intermediate Similarity	NPD5344	Discontinued
0.7103	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7638	Approved
0.6897	Remote Similarity	NPD8133	Approved
0.6881	Remote Similarity	NPD7640	Approved
0.6881	Remote Similarity	NPD7639	Approved
0.6796	Remote Similarity	NPD7524	Approved
0.6727	Remote Similarity	NPD6648	Approved
0.6724	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6053	Discontinued
0.6636	Remote Similarity	NPD4225	Approved
0.6602	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7115	Discovery
0.6569	Remote Similarity	NPD6695	Phase 3
0.6552	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7637	Suspended
0.6509	Remote Similarity	NPD1695	Approved
0.6508	Remote Similarity	NPD8293	Discontinued
0.6504	Remote Similarity	NPD8513	Phase 3
0.6504	Remote Similarity	NPD8515	Approved
0.6504	Remote Similarity	NPD8516	Approved
0.6504	Remote Similarity	NPD8517	Approved
0.6457	Remote Similarity	NPD7736	Approved
0.6452	Remote Similarity	NPD6370	Approved
0.6364	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6051	Approved
0.6349	Remote Similarity	NPD7492	Approved
0.6321	Remote Similarity	NPD4251	Approved
0.6321	Remote Similarity	NPD7750	Discontinued
0.6321	Remote Similarity	NPD4250	Approved
0.6316	Remote Similarity	NPD7632	Discontinued
0.6311	Remote Similarity	NPD6009	Approved
0.6299	Remote Similarity	NPD6616	Approved
0.6296	Remote Similarity	NPD5785	Approved
0.629	Remote Similarity	NPD6054	Approved
0.629	Remote Similarity	NPD6059	Approved
0.6275	Remote Similarity	NPD4819	Approved
0.6275	Remote Similarity	NPD4821	Approved
0.6275	Remote Similarity	NPD4822	Approved
0.6275	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4820	Approved
0.6275	Remote Similarity	NPD6931	Approved
0.6275	Remote Similarity	NPD6930	Phase 2
0.6271	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.627	Remote Similarity	NPD7829	Approved
0.627	Remote Similarity	NPD7642	Approved
0.627	Remote Similarity	NPD8328	Phase 3
0.627	Remote Similarity	NPD7830	Approved
0.6259	Remote Similarity	NPD7625	Phase 1
0.625	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD7078	Approved
0.625	Remote Similarity	NPD6882	Approved
0.6239	Remote Similarity	NPD7983	Approved
0.6238	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4249	Approved
0.6218	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6902	Approved
0.62	Remote Similarity	NPD6933	Approved
0.6198	Remote Similarity	NPD4632	Approved
0.6176	Remote Similarity	NPD6929	Approved
0.617	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.616	Remote Similarity	NPD6319	Approved
0.6154	Remote Similarity	NPD6675	Approved
0.6154	Remote Similarity	NPD6402	Approved
0.6154	Remote Similarity	NPD7128	Approved
0.6154	Remote Similarity	NPD5739	Approved
0.6142	Remote Similarity	NPD7604	Phase 2
0.6126	Remote Similarity	NPD5282	Discontinued
0.6117	Remote Similarity	NPD7514	Phase 3
0.6116	Remote Similarity	NPD8297	Approved
0.6111	Remote Similarity	NPD6015	Approved
0.6111	Remote Similarity	NPD6016	Approved
0.6095	Remote Similarity	NPD5362	Discontinued
0.6091	Remote Similarity	NPD7087	Discontinued
0.6078	Remote Similarity	NPD4271	Approved
0.6078	Remote Similarity	NPD4268	Approved
0.6071	Remote Similarity	NPD5695	Phase 3
0.6063	Remote Similarity	NPD5988	Approved
0.605	Remote Similarity	NPD6881	Approved
0.605	Remote Similarity	NPD7320	Approved
0.605	Remote Similarity	NPD6899	Approved
0.6047	Remote Similarity	NPD8451	Approved
0.6036	Remote Similarity	NPD6399	Phase 3
0.6018	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6067	Discontinued
0.6	Remote Similarity	NPD6926	Approved
0.6	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD6435	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD6924	Approved
0.6	Remote Similarity	NPD5209	Approved
0.6	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7641	Discontinued
0.6	Remote Similarity	NPD8074	Phase 3
0.6	Remote Similarity	NPD6373	Approved
0.5984	Remote Similarity	NPD8444	Approved
0.5981	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD6893	Approved
0.598	Remote Similarity	NPD5776	Phase 2
0.598	Remote Similarity	NPD6925	Approved
0.598	Remote Similarity	NPD6932	Approved
0.5966	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD5701	Approved
0.5966	Remote Similarity	NPD5697	Approved
0.5962	Remote Similarity	NPD7332	Phase 2
0.5962	Remote Similarity	NPD7525	Registered
0.5956	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6883	Approved
0.595	Remote Similarity	NPD7290	Approved
0.595	Remote Similarity	NPD7102	Approved
0.5943	Remote Similarity	NPD5331	Approved
0.5943	Remote Similarity	NPD7154	Phase 3
0.5943	Remote Similarity	NPD5332	Approved
0.5923	Remote Similarity	NPD8273	Phase 1
0.5922	Remote Similarity	NPD7145	Approved
0.592	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD5696	Approved
0.5905	Remote Similarity	NPD4790	Discontinued
0.5902	Remote Similarity	NPD6650	Approved
0.5902	Remote Similarity	NPD6617	Approved
0.5902	Remote Similarity	NPD6847	Approved
0.5902	Remote Similarity	NPD8130	Phase 1
0.5902	Remote Similarity	NPD6649	Approved
0.5902	Remote Similarity	NPD6869	Approved
0.5893	Remote Similarity	NPD5779	Approved
0.5893	Remote Similarity	NPD5778	Approved
0.5893	Remote Similarity	NPD8171	Discontinued
0.5882	Remote Similarity	NPD6008	Approved
0.5882	Remote Similarity	NPD6640	Phase 3
0.5877	Remote Similarity	NPD7839	Suspended
0.5868	Remote Similarity	NPD6012	Approved
0.5868	Remote Similarity	NPD6014	Approved
0.5868	Remote Similarity	NPD6013	Approved
0.5865	Remote Similarity	NPD6683	Phase 2
0.5865	Remote Similarity	NPD8392	Approved
0.5865	Remote Similarity	NPD8391	Approved
0.5865	Remote Similarity	NPD8390	Approved
0.5859	Remote Similarity	NPD5983	Phase 2
0.5856	Remote Similarity	NPD3168	Discontinued
0.5846	Remote Similarity	NPD8342	Approved
0.5846	Remote Similarity	NPD8299	Approved
0.5846	Remote Similarity	NPD8340	Approved
0.5846	Remote Similarity	NPD8341	Approved
0.5833	Remote Similarity	NPD5363	Approved
0.5833	Remote Similarity	NPD6033	Approved
0.5821	Remote Similarity	NPD7260	Phase 2
0.5818	Remote Similarity	NPD5737	Approved
0.5818	Remote Similarity	NPD6672	Approved
0.5814	Remote Similarity	NPD8080	Discontinued
0.581	Remote Similarity	NPD5368	Approved
0.5804	Remote Similarity	NPD5693	Phase 1
0.5804	Remote Similarity	NPD6411	Approved
0.5802	Remote Similarity	NPD6336	Discontinued
0.5794	Remote Similarity	NPD7505	Discontinued
0.5794	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6110	Phase 1
0.5789	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD6011	Approved
0.578	Remote Similarity	NPD7521	Approved
0.578	Remote Similarity	NPD7146	Approved
0.578	Remote Similarity	NPD7334	Approved
0.578	Remote Similarity	NPD6684	Approved
0.578	Remote Similarity	NPD6409	Approved
0.578	Remote Similarity	NPD5330	Approved
0.5772	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD4753	Phase 2
0.5755	Remote Similarity	NPD6898	Phase 1
0.5755	Remote Similarity	NPD5369	Approved
0.575	Remote Similarity	NPD4211	Phase 1
0.5746	Remote Similarity	NPD5956	Approved
0.5727	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8336	Approved
0.5714	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8337	Approved
0.5701	Remote Similarity	NPD4269	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