NPASS Compound

Structure

CID272946 OpenBabel06191716082D 39 41 0 0 1 0 0 0 0 0999 V2000 -0.8660 2.4319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1390 -1.5731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4417 -2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3461 3.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6165 -4.2188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6390 3.6390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5050 3.1390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6762 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8102 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6762 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9441 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8102 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 2.6390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6730 2.8978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6730 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6049 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8910 -0.4540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6390 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7346 -1.4417 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2121 3.4319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1625 -3.3278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9441 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -0.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3461 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3461 1.9319 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2531 -1.5981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2588 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0781 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6390 2.6390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0781 3.9319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8362 -3.2755 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2588 0.9659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0781 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9150 0.4034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2121 2.4319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -2.4891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2121 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 30 1 0 0 0 0 7 30 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 23 2 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 18 2 0 0 0 0 14 30 1 0 0 0 0 15 19 2 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 16 26 1 0 0 0 0 17 20 1 0 0 0 0 17 31 1 0 0 0 0 18 28 1 0 0 0 0 19 25 1 0 0 0 0 20 3 1 6 0 0 0 20 27 1 0 0 0 0 21 32 2 0 0 0 0 21 37 1 0 0 0 0 22 33 2 0 0 0 0 22 38 1 0 0 0 0 23 29 1 0 0 0 0 24 27 1 0 0 0 0 24 31 1 1 0 0 0 25 39 1 1 0 0 0 26 30 1 0 0 0 0 26 37 1 6 0 0 0 27 38 1 1 0 0 0 28 31 1 0 0 0 0 28 34 2 0 0 0 0 29 35 2 0 0 0 0 29 39 1 0 0 0 0 31 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.27
Volume:	565.656
LogP:	4.344
LogD:	3.229
LogS:	-4.886
# Rotatable Bonds:	7
TPSA:	116.2
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.335
Synthetic Accessibility Score:	5.214
Fsp3:	0.548
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:	-4.81
MDCK Permeability:	5.232140756561421e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.049
20% Bioavailability (F20%):	0.932
30% Bioavailability (F30%):	0.669

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.198
Plasma Protein Binding (PPB):	99.63947296142578%
Volume Distribution (VD):	2.683
Pgp-substrate:	5.459565162658691%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.051
CYP2C19-inhibitor:	0.149
CYP2C19-substrate:	0.144
CYP2C9-inhibitor:	0.874
CYP2C9-substrate:	0.384
CYP2D6-inhibitor:	0.093
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.892
CYP3A4-substrate:	0.574

ADMET: Excretion

Clearance (CL):	3.267
Half-life (T1/2):	0.316

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.961
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.491
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.136
Carcinogencity:	0.047
Eye Corrosion:	0.005
Eye Irritation:	0.037
Respiratory Toxicity:	0.459

Download Data

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

Natural Product: NPC272946

Natural Product ID:	NPC272946
*Common Name:**	Pubescene D
IUPAC Name:	[(1S,2R,3aR,5E,9R,11R,12E,13aS)-1,9-diacetyloxy-3a-hydroxy-2,5,8,8,12-pentamethyl-4-oxo-1,2,3,7,9,10,11,13a-octahydrocyclopenta[12]annulen-11-yl] benzoate
Synonyms:	Pubescene D
Standard InCHIKey:	UAKCWZDVHJZVRU-CJSPNJQUSA-N
Standard InCHI:	InChI=1S/C31H40O8/c1-18-13-14-30(6,7)26(37-21(4)32)16-25(39-29(35)23-11-9-8-10-12-23)19(2)15-24-27(38-22(5)33)20(3)17-31(24,36)28(18)34/h8-13,15,20,24-27,36H,14,16-17H2,1-7H3/b18-13+,19-15+/t20-,24+,25-,26-,27+,31-/m1/s1
SMILES:	C/C/1=CCC(C)(C)[C@@H](C[C@H](/C(=C/[C@H]2[C@H]([C@H](C)C[C@@]2(C1=O)O)OC(=O)C)/C)OC(=O)c1ccccc1)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL488000
PubChem CID:	10370059
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002877] Jatrophane and cyclojatrophane diterpenoids

*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
NPO11807	Euphorbia pubescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165162]
NPO11807	Euphorbia pubescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11807	Euphorbia pubescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
GI50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	37500.0	nM	PMID[490073]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	37500.0	nM	PMID[490073]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	90120.0	nM	PMID[490073]

☑ 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 NPC272946 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	262
0.1-0.2	952
0.2-0.3	2174
0.3-0.4	5837
0.4-0.5	11489
0.5-0.6	14412
0.6-0.7	6649
0.7-0.8	737
0.8-0.85	51
0.85-0.9	72
0.9-0.95	58
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9603	High Similarity	NPC477364
0.9528	High Similarity	NPC477368
0.9528	High Similarity	NPC477359
0.9453	High Similarity	NPC477367
0.9453	High Similarity	NPC232888
0.9365	High Similarity	NPC42234
0.9302	High Similarity	NPC472247
0.9242	High Similarity	NPC473497
0.9219	High Similarity	NPC477360
0.9194	High Similarity	NPC477362
0.9154	High Similarity	NPC475262
0.9154	High Similarity	NPC265459
0.9154	High Similarity	NPC290833
0.9154	High Similarity	NPC270364
0.9104	High Similarity	NPC45307
0.9104	High Similarity	NPC153214
0.9098	High Similarity	NPC475413
0.9098	High Similarity	NPC474303
0.9084	High Similarity	NPC285221
0.9084	High Similarity	NPC194769
0.9077	High Similarity	NPC472250
0.9048	High Similarity	NPC477363
0.9048	High Similarity	NPC477366
0.9015	High Similarity	NPC86772
0.8976	High Similarity	NPC477357
0.8976	High Similarity	NPC477365
0.8947	High Similarity	NPC325805
0.8947	High Similarity	NPC272523
0.8947	High Similarity	NPC276652
0.8939	High Similarity	NPC477358
0.8923	High Similarity	NPC239358
0.8923	High Similarity	NPC233860
0.8906	High Similarity	NPC477370
0.8905	High Similarity	NPC170668
0.8881	High Similarity	NPC475660
0.8881	High Similarity	NPC251294
0.8855	High Similarity	NPC472248
0.8841	High Similarity	NPC205389
0.8837	High Similarity	NPC37968
0.8815	High Similarity	NPC473654
0.8788	High Similarity	NPC28836
0.8788	High Similarity	NPC311492
0.8779	High Similarity	NPC233692
0.874	High Similarity	NPC8990
0.8722	High Similarity	NPC79699
0.8722	High Similarity	NPC200154
0.8714	High Similarity	NPC477097
0.8714	High Similarity	NPC477101
0.8714	High Similarity	NPC25484
0.8714	High Similarity	NPC125033
0.8714	High Similarity	NPC232583
0.8714	High Similarity	NPC477099
0.8686	High Similarity	NPC477096
0.8686	High Similarity	NPC82467
0.8686	High Similarity	NPC477094
0.8676	High Similarity	NPC242355
0.8672	High Similarity	NPC477369
0.8657	High Similarity	NPC202729
0.8626	High Similarity	NPC475508
0.8593	High Similarity	NPC27721
0.854	High Similarity	NPC187566
0.8538	High Similarity	NPC472706
0.8531	High Similarity	NPC477098
0.8531	High Similarity	NPC477100
0.8529	High Similarity	NPC473301
0.8507	High Similarity	NPC153617
0.85	High Similarity	NPC477095
0.8485	Intermediate Similarity	NPC475452
0.8485	Intermediate Similarity	NPC475671
0.8473	Intermediate Similarity	NPC472707
0.845	Intermediate Similarity	NPC472704
0.8372	Intermediate Similarity	NPC472703
0.837	Intermediate Similarity	NPC134937
0.837	Intermediate Similarity	NPC298547
0.837	Intermediate Similarity	NPC324898
0.837	Intermediate Similarity	NPC329913
0.8346	Intermediate Similarity	NPC472708
0.8309	Intermediate Similarity	NPC279637
0.8309	Intermediate Similarity	NPC149401
0.8288	Intermediate Similarity	NPC70344
0.8261	Intermediate Similarity	NPC170718
0.8248	Intermediate Similarity	NPC52523
0.8248	Intermediate Similarity	NPC217673
0.8235	Intermediate Similarity	NPC126516
0.8219	Intermediate Similarity	NPC469456
0.8214	Intermediate Similarity	NPC183540
0.8214	Intermediate Similarity	NPC51181
0.8209	Intermediate Similarity	NPC122504
0.8209	Intermediate Similarity	NPC3450
0.8197	Intermediate Similarity	NPC469636
0.8188	Intermediate Similarity	NPC327511
0.8188	Intermediate Similarity	NPC205305
0.8182	Intermediate Similarity	NPC476599
0.8156	Intermediate Similarity	NPC95449
0.814	Intermediate Similarity	NPC473243
0.8133	Intermediate Similarity	NPC55744
0.8129	Intermediate Similarity	NPC53361
0.8129	Intermediate Similarity	NPC121268
0.8102	Intermediate Similarity	NPC203486
0.8085	Intermediate Similarity	NPC475135
0.8074	Intermediate Similarity	NPC82712
0.8042	Intermediate Similarity	NPC127857
0.8016	Intermediate Similarity	NPC153053
0.8016	Intermediate Similarity	NPC307651
0.8015	Intermediate Similarity	NPC72915
0.8	Intermediate Similarity	NPC270699
0.8	Intermediate Similarity	NPC82899
0.8	Intermediate Similarity	NPC9905
0.7985	Intermediate Similarity	NPC169913
0.797	Intermediate Similarity	NPC246166
0.797	Intermediate Similarity	NPC295664
0.7959	Intermediate Similarity	NPC138641
0.7959	Intermediate Similarity	NPC22571
0.7959	Intermediate Similarity	NPC283875
0.7959	Intermediate Similarity	NPC469648
0.7959	Intermediate Similarity	NPC469647
0.7958	Intermediate Similarity	NPC182869
0.7943	Intermediate Similarity	NPC162613
0.7943	Intermediate Similarity	NPC87934
0.7939	Intermediate Similarity	NPC50872
0.7926	Intermediate Similarity	NPC51448
0.7926	Intermediate Similarity	NPC115797
0.7923	Intermediate Similarity	NPC204784
0.7922	Intermediate Similarity	NPC161151
0.792	Intermediate Similarity	NPC1082
0.792	Intermediate Similarity	NPC305912
0.7917	Intermediate Similarity	NPC134131
0.7917	Intermediate Similarity	NPC478264
0.7917	Intermediate Similarity	NPC25043
0.791	Intermediate Similarity	NPC275576
0.7902	Intermediate Similarity	NPC131966
0.7902	Intermediate Similarity	NPC191387
0.7891	Intermediate Similarity	NPC161955
0.7891	Intermediate Similarity	NPC472398
0.7891	Intermediate Similarity	NPC51602
0.7891	Intermediate Similarity	NPC471103
0.7887	Intermediate Similarity	NPC266374
0.7877	Intermediate Similarity	NPC250046
0.7877	Intermediate Similarity	NPC60509
0.7877	Intermediate Similarity	NPC81698
0.7862	Intermediate Similarity	NPC478263
0.7857	Intermediate Similarity	NPC321852
0.7852	Intermediate Similarity	NPC469730
0.7852	Intermediate Similarity	NPC473632
0.7852	Intermediate Similarity	NPC473611
0.7852	Intermediate Similarity	NPC132599
0.7842	Intermediate Similarity	NPC48929
0.784	Intermediate Similarity	NPC93084
0.784	Intermediate Similarity	NPC196246
0.784	Intermediate Similarity	NPC251854
0.784	Intermediate Similarity	NPC214067
0.7838	Intermediate Similarity	NPC233581
0.7838	Intermediate Similarity	NPC145649
0.7832	Intermediate Similarity	NPC192658
0.7826	Intermediate Similarity	NPC125153
0.7823	Intermediate Similarity	NPC161239
0.7823	Intermediate Similarity	NPC112216
0.7823	Intermediate Similarity	NPC165260
0.7823	Intermediate Similarity	NPC198455
0.7823	Intermediate Similarity	NPC7095
0.781	Intermediate Similarity	NPC471832
0.78	Intermediate Similarity	NPC11410
0.7795	Intermediate Similarity	NPC161611
0.7793	Intermediate Similarity	NPC471100
0.7793	Intermediate Similarity	NPC471107
0.7793	Intermediate Similarity	NPC471162
0.7787	Intermediate Similarity	NPC474365
0.7787	Intermediate Similarity	NPC301943
0.7786	Intermediate Similarity	NPC477893
0.7786	Intermediate Similarity	NPC477896
0.7778	Intermediate Similarity	NPC477894
0.7778	Intermediate Similarity	NPC260818
0.777	Intermediate Similarity	NPC472656
0.777	Intermediate Similarity	NPC101043
0.777	Intermediate Similarity	NPC306799
0.7761	Intermediate Similarity	NPC471466
0.776	Intermediate Similarity	NPC17417
0.776	Intermediate Similarity	NPC83628
0.776	Intermediate Similarity	NPC10251
0.776	Intermediate Similarity	NPC265407
0.7754	Intermediate Similarity	NPC470278
0.774	Intermediate Similarity	NPC475552
0.774	Intermediate Similarity	NPC312393
0.7734	Intermediate Similarity	NPC474363
0.7733	Intermediate Similarity	NPC251139
0.7733	Intermediate Similarity	NPC21410
0.7733	Intermediate Similarity	NPC473670
0.7733	Intermediate Similarity	NPC282239
0.7724	Intermediate Similarity	NPC34943
0.7721	Intermediate Similarity	NPC473220
0.7721	Intermediate Similarity	NPC470753
0.7721	Intermediate Similarity	NPC204579
0.7708	Intermediate Similarity	NPC472546
0.7703	Intermediate Similarity	NPC476173
0.7697	Intermediate Similarity	NPC159692
0.7692	Intermediate Similarity	NPC473440
0.7692	Intermediate Similarity	NPC90614
0.7692	Intermediate Similarity	NPC97667
0.7692	Intermediate Similarity	NPC171207
0.7692	Intermediate Similarity	NPC472547

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 NPC272946 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	730
0.2-0.3	1510
0.3-0.4	2800
0.4-0.5	2327
0.5-0.6	1206
0.6-0.7	326
0.7-0.8	30
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8561	High Similarity	NPD7236	Approved
0.8392	Intermediate Similarity	NPD7239	Suspended
0.792	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD7057	Phase 3
0.7881	Intermediate Similarity	NPD7058	Phase 2
0.7852	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD2182	Approved
0.7547	Intermediate Similarity	NPD7799	Discontinued
0.7538	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD6085	Phase 2
0.746	Intermediate Similarity	NPD6685	Approved
0.7447	Intermediate Similarity	NPD7961	Discontinued
0.744	Intermediate Similarity	NPD164	Approved
0.7422	Intermediate Similarity	NPD2067	Discontinued
0.7407	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6647	Phase 2
0.7344	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2629	Approved
0.7222	Intermediate Similarity	NPD5765	Approved
0.7206	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6912	Phase 3
0.7176	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1237	Approved
0.7143	Intermediate Similarity	NPD6362	Approved
0.7121	Intermediate Similarity	NPD7094	Approved
0.7121	Intermediate Similarity	NPD6858	Approved
0.712	Intermediate Similarity	NPD1238	Approved
0.7101	Intermediate Similarity	NPD6287	Discontinued
0.7095	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD4198	Discontinued
0.7075	Intermediate Similarity	NPD7305	Phase 1
0.7063	Intermediate Similarity	NPD7008	Discontinued
0.7059	Intermediate Similarity	NPD6273	Approved
0.7059	Intermediate Similarity	NPD9545	Approved
0.6984	Remote Similarity	NPD2066	Phase 3
0.698	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6005	Phase 3
0.698	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6004	Phase 3
0.698	Remote Similarity	NPD6002	Phase 3
0.6972	Remote Similarity	NPD5647	Approved
0.6954	Remote Similarity	NPD4628	Phase 3
0.6953	Remote Similarity	NPD1930	Approved
0.6953	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD1929	Approved
0.6939	Remote Similarity	NPD6653	Approved
0.6935	Remote Similarity	NPD1693	Approved
0.6934	Remote Similarity	NPD7741	Discontinued
0.6913	Remote Similarity	NPD7137	Phase 2
0.6905	Remote Similarity	NPD9495	Approved
0.6889	Remote Similarity	NPD5951	Approved
0.6871	Remote Similarity	NPD6355	Discontinued
0.6867	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4806	Approved
0.6857	Remote Similarity	NPD4807	Approved
0.6855	Remote Similarity	NPD5761	Phase 2
0.6855	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5760	Phase 2
0.6849	Remote Similarity	NPD6663	Approved
0.6845	Remote Similarity	NPD6765	Approved
0.6845	Remote Similarity	NPD6764	Approved
0.6845	Remote Similarity	NPD8368	Discontinued
0.6845	Remote Similarity	NPD7685	Pre-registration
0.6835	Remote Similarity	NPD5306	Approved
0.6835	Remote Similarity	NPD5305	Approved
0.6824	Remote Similarity	NPD8407	Phase 2
0.6815	Remote Similarity	NPD2652	Approved
0.6815	Remote Similarity	NPD2650	Approved
0.6812	Remote Similarity	NPD7009	Phase 2
0.6809	Remote Similarity	NPD3972	Approved
0.6806	Remote Similarity	NPD3662	Phase 3
0.6806	Remote Similarity	NPD5736	Approved
0.6806	Remote Similarity	NPD3661	Approved
0.6806	Remote Similarity	NPD3664	Approved
0.6806	Remote Similarity	NPD3663	Approved
0.6791	Remote Similarity	NPD969	Suspended
0.6788	Remote Similarity	NPD9493	Approved
0.6781	Remote Similarity	NPD3764	Approved
0.6774	Remote Similarity	NPD1088	Approved
0.6772	Remote Similarity	NPD6599	Discontinued
0.6769	Remote Similarity	NPD5909	Discontinued
0.6759	Remote Similarity	NPD6832	Phase 2
0.6748	Remote Similarity	NPD9256	Approved
0.6748	Remote Similarity	NPD9258	Approved
0.6744	Remote Similarity	NPD8434	Phase 2
0.6739	Remote Similarity	NPD7610	Discontinued
0.6733	Remote Similarity	NPD2799	Discontinued
0.6716	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1876	Approved
0.6709	Remote Similarity	NPD7458	Discontinued
0.6691	Remote Similarity	NPD6010	Discontinued
0.6688	Remote Similarity	NPD3887	Approved
0.6686	Remote Similarity	NPD6784	Approved
0.6686	Remote Similarity	NPD6785	Approved
0.6667	Remote Similarity	NPD4136	Approved
0.6667	Remote Similarity	NPD2569	Approved
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD2567	Approved
0.6667	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD4135	Approved
0.6667	Remote Similarity	NPD4106	Approved
0.6647	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD230	Phase 1
0.6643	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7075	Discontinued
0.6622	Remote Similarity	NPD7713	Phase 3
0.6615	Remote Similarity	NPD1932	Approved
0.6613	Remote Similarity	NPD1089	Approved
0.6613	Remote Similarity	NPD1086	Approved
0.6613	Remote Similarity	NPD1090	Approved
0.6603	Remote Similarity	NPD6799	Approved
0.6597	Remote Similarity	NPD5667	Approved
0.6596	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5048	Discontinued
0.659	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD1202	Approved
0.6581	Remote Similarity	NPD2354	Approved
0.6581	Remote Similarity	NPD6190	Approved
0.6575	Remote Similarity	NPD5204	Approved
0.6573	Remote Similarity	NPD9717	Approved
0.6571	Remote Similarity	NPD8435	Approved
0.6571	Remote Similarity	NPD8360	Approved
0.6571	Remote Similarity	NPD8361	Approved
0.6568	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD2329	Discontinued
0.6561	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD9259	Approved
0.6557	Remote Similarity	NPD9257	Approved
0.6552	Remote Similarity	NPD2797	Approved
0.6543	Remote Similarity	NPD7819	Suspended
0.6536	Remote Similarity	NPD2346	Discontinued
0.6536	Remote Similarity	NPD5763	Approved
0.6536	Remote Similarity	NPD5762	Approved
0.6532	Remote Similarity	NPD800	Approved
0.6531	Remote Similarity	NPD7055	Discontinued
0.6525	Remote Similarity	NPD4105	Approved
0.6525	Remote Similarity	NPD4102	Approved
0.6522	Remote Similarity	NPD4766	Approved
0.6519	Remote Similarity	NPD1317	Discontinued
0.6516	Remote Similarity	NPD8166	Discontinued
0.6513	Remote Similarity	NPD7033	Discontinued
0.651	Remote Similarity	NPD6233	Phase 2
0.6507	Remote Similarity	NPD2798	Approved
0.6506	Remote Similarity	NPD8127	Discontinued
0.649	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6039	Approved
0.6485	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD1989	Approved
0.6483	Remote Similarity	NPD2198	Approved
0.6483	Remote Similarity	NPD2199	Approved
0.6481	Remote Similarity	NPD6801	Discontinued
0.648	Remote Similarity	NPD3672	Approved
0.648	Remote Similarity	NPD3673	Approved
0.6471	Remote Similarity	NPD6649	Approved
0.6471	Remote Similarity	NPD6650	Approved
0.6471	Remote Similarity	NPD2935	Discontinued
0.6467	Remote Similarity	NPD4140	Approved
0.6458	Remote Similarity	NPD6637	Approved
0.6458	Remote Similarity	NPD1608	Approved
0.6457	Remote Similarity	NPD8150	Discontinued
0.6456	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD2534	Approved
0.6456	Remote Similarity	NPD2533	Approved
0.6456	Remote Similarity	NPD2532	Approved
0.6443	Remote Similarity	NPD6798	Discontinued
0.6443	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD3266	Approved
0.6438	Remote Similarity	NPD3267	Approved
0.6429	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2353	Approved
0.642	Remote Similarity	NPD7411	Suspended
0.6419	Remote Similarity	NPD4617	Approved
0.6419	Remote Similarity	NPD4620	Approved
0.6419	Remote Similarity	NPD5201	Approved
0.6419	Remote Similarity	NPD5203	Approved
0.641	Remote Similarity	NPD4110	Phase 3
0.641	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7003	Approved
0.641	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD4308	Phase 3
0.64	Remote Similarity	NPD8032	Phase 2
0.64	Remote Similarity	NPD7715	Approved
0.64	Remote Similarity	NPD5347	Phase 2
0.64	Remote Similarity	NPD7714	Approved
0.64	Remote Similarity	NPD5346	Phase 2
0.6398	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD4233	Approved
0.6397	Remote Similarity	NPD4234	Approved
0.6395	Remote Similarity	NPD1019	Discontinued
0.6377	Remote Similarity	NPD5277	Phase 2
0.6376	Remote Similarity	NPD7095	Approved
0.6375	Remote Similarity	NPD5403	Approved
0.6371	Remote Similarity	NPD1087	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