NPASS Compound

Structure

NPC471413 OpenBabel07101718182D 27 29 0 0 1 0 0 0 0 0999 V2000 0.8372 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6743 3.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3205 3.2538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8038 2.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8372 0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6743 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6743 0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5510 -0.1832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8372 2.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2360 -0.5413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8372 1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8675 0.5004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0467 -0.0148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 -0.4833 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8372 4.3500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4847 0.0670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 1.4500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 2.9000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8311 0.9695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 2.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9667 0.0000 C 0 0 2 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 -0.8372 5.3167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3047 1.7802 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1262 -0.9584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7965 0.9189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.8667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 17 1 0 0 0 0 8 12 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 13 1 0 0 0 0 10 16 2 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 26 1 0 0 0 0 14 22 1 1 0 0 0 15 23 2 0 0 0 0 15 27 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 6 0 0 0 18 20 1 0 0 0 0 18 27 1 6 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 21 22 1 1 0 0 0 22 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.24
Volume:	399.441
LogP:	4.107
LogD:	3.65
LogS:	-4.433
# Rotatable Bonds:	5
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.757
Synthetic Accessibility Score:	4.415
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.797
MDCK Permeability:	2.461266194586642e-05
Pgp-inhibitor:	0.896
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.208

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147
Plasma Protein Binding (PPB):	94.19882202148438%
Volume Distribution (VD):	1.579
Pgp-substrate:	5.328494071960449%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.315
CYP2C9-inhibitor:	0.458
CYP2C9-substrate:	0.727
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.575
CYP3A4-inhibitor:	0.256
CYP3A4-substrate:	0.27

ADMET: Excretion

Clearance (CL):	7.738
Half-life (T1/2):	0.204

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.197
Drug-inuced Liver Injury (DILI):	0.097
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.319
Maximum Recommended Daily Dose:	0.734
Skin Sensitization:	0.268
Carcinogencity:	0.386
Eye Corrosion:	0.018
Eye Irritation:	0.049
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC471413

Natural Product ID:	NPC471413
*Common Name:**	(Rel 3S,5S,8R,9R,10S)-3-Acetoxy-9-Hydroxy-13(14)-Labden-16,15-Olide
IUPAC Name:	[(2S,4aS,5R,6R,8aS)-5-hydroxy-1,1,4a,6-tetramethyl-5-[2-(5-oxo-2H-furan-4-yl)ethyl]-3,4,6,7,8,8a-hexahydro-2H-naphthalen-2-yl] acetate
Synonyms:
Standard InCHIKey:	LEEPSVTWQNEWST-NDOLZWLNSA-N
Standard InCHI:	InChI=1S/C22H34O5/c1-14-6-7-17-20(3,4)18(27-15(2)23)9-11-21(17,5)22(14,25)12-8-16-10-13-26-19(16)24/h10,14,17-18,25H,6-9,11-13H2,1-5H3/t14-,17+,18+,21+,22-/m1/s1
SMILES:	CC1CCC2C(C(CCC2(C1(CCC3=CCOC3=O)O)C)OC(=O)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2436611
PubChem CID:	72375238
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[10579867]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	subterranean part	n.a.	n.a.	PMID[11374949]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11536386]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[11975496]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24035341]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	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
IC50	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	90.0	%	PMID[537167]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	49100.0	nM	PMID[537167]

☑ 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 NPC471413 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	197
0.1-0.2	1190
0.2-0.3	3855
0.3-0.4	6918
0.4-0.5	13622
0.5-0.6	6894
0.6-0.7	6502
0.7-0.8	3157
0.8-0.85	304
0.85-0.9	47
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9892	High Similarity	NPC471412
0.9787	High Similarity	NPC162973
0.9674	High Similarity	NPC29952
0.9053	High Similarity	NPC234993
0.9053	High Similarity	NPC134072
0.898	High Similarity	NPC476081
0.898	High Similarity	NPC476769
0.8969	High Similarity	NPC471041
0.8936	High Similarity	NPC7349
0.8936	High Similarity	NPC139692
0.8911	High Similarity	NPC275539
0.8911	High Similarity	NPC189075
0.8889	High Similarity	NPC120321
0.8842	High Similarity	NPC105490
0.8812	High Similarity	NPC302788
0.8812	High Similarity	NPC110496
0.8776	High Similarity	NPC117685
0.8776	High Similarity	NPC476767
0.8713	High Similarity	NPC34768
0.87	High Similarity	NPC180204
0.87	High Similarity	NPC112009
0.87	High Similarity	NPC254202
0.8679	High Similarity	NPC471816
0.866	High Similarity	NPC242848
0.8627	High Similarity	NPC67321
0.8627	High Similarity	NPC187435
0.8627	High Similarity	NPC179380
0.8617	High Similarity	NPC174342
0.86	High Similarity	NPC475038
0.86	High Similarity	NPC109195
0.8587	High Similarity	NPC65661
0.8586	High Similarity	NPC47024
0.8586	High Similarity	NPC201406
0.8586	High Similarity	NPC251680
0.8586	High Similarity	NPC54705
0.8571	High Similarity	NPC90952
0.8571	High Similarity	NPC38530
0.8571	High Similarity	NPC194951
0.8571	High Similarity	NPC84335
0.8571	High Similarity	NPC4573
0.8571	High Similarity	NPC269530
0.8571	High Similarity	NPC470063
0.8571	High Similarity	NPC12046
0.8571	High Similarity	NPC474343
0.8571	High Similarity	NPC277769
0.8558	High Similarity	NPC179642
0.8557	High Similarity	NPC276110
0.8544	High Similarity	NPC476802
0.8544	High Similarity	NPC89171
0.8544	High Similarity	NPC306265
0.8542	High Similarity	NPC472871
0.8529	High Similarity	NPC469607
0.8515	High Similarity	NPC478057
0.8505	High Similarity	NPC469794
0.8505	High Similarity	NPC196931
0.8505	High Similarity	NPC72772
0.8491	Intermediate Similarity	NPC157441
0.8491	Intermediate Similarity	NPC25909
0.8485	Intermediate Similarity	NPC108368
0.8485	Intermediate Similarity	NPC23364
0.8485	Intermediate Similarity	NPC72647
0.8485	Intermediate Similarity	NPC107806
0.8485	Intermediate Similarity	NPC57079
0.8478	Intermediate Similarity	NPC32223
0.8469	Intermediate Similarity	NPC209297
0.8469	Intermediate Similarity	NPC475380
0.8469	Intermediate Similarity	NPC202833
0.8454	Intermediate Similarity	NPC57117
0.8454	Intermediate Similarity	NPC250075
0.8438	Intermediate Similarity	NPC473944
0.8438	Intermediate Similarity	NPC472975
0.8421	Intermediate Similarity	NPC5509
0.8416	Intermediate Similarity	NPC165250
0.8416	Intermediate Similarity	NPC295791
0.84	Intermediate Similarity	NPC470074
0.84	Intermediate Similarity	NPC476299
0.84	Intermediate Similarity	NPC306856
0.84	Intermediate Similarity	NPC474012
0.84	Intermediate Similarity	NPC324841
0.8387	Intermediate Similarity	NPC86316
0.8387	Intermediate Similarity	NPC106416
0.8384	Intermediate Similarity	NPC311241
0.8384	Intermediate Similarity	NPC51499
0.8384	Intermediate Similarity	NPC475446
0.8384	Intermediate Similarity	NPC100912
0.8384	Intermediate Similarity	NPC253826
0.8381	Intermediate Similarity	NPC472666
0.8367	Intermediate Similarity	NPC90014
0.8367	Intermediate Similarity	NPC183012
0.8351	Intermediate Similarity	NPC472303
0.8351	Intermediate Similarity	NPC475657
0.835	Intermediate Similarity	NPC127609
0.835	Intermediate Similarity	NPC478208
0.8333	Intermediate Similarity	NPC78973
0.8333	Intermediate Similarity	NPC36688
0.8333	Intermediate Similarity	NPC51486
0.8333	Intermediate Similarity	NPC95899
0.8333	Intermediate Similarity	NPC232202
0.8333	Intermediate Similarity	NPC282233
0.8333	Intermediate Similarity	NPC95585
0.8317	Intermediate Similarity	NPC222875
0.8317	Intermediate Similarity	NPC303559
0.8317	Intermediate Similarity	NPC11974
0.8317	Intermediate Similarity	NPC268829
0.8317	Intermediate Similarity	NPC295110
0.8317	Intermediate Similarity	NPC475099
0.8317	Intermediate Similarity	NPC247701
0.8317	Intermediate Similarity	NPC25177
0.8316	Intermediate Similarity	NPC104560
0.8316	Intermediate Similarity	NPC50847
0.8316	Intermediate Similarity	NPC106332
0.8302	Intermediate Similarity	NPC474846
0.8302	Intermediate Similarity	NPC469656
0.8302	Intermediate Similarity	NPC469655
0.83	Intermediate Similarity	NPC325229
0.83	Intermediate Similarity	NPC316598
0.83	Intermediate Similarity	NPC216478
0.83	Intermediate Similarity	NPC275086
0.83	Intermediate Similarity	NPC218107
0.83	Intermediate Similarity	NPC278673
0.8298	Intermediate Similarity	NPC131813
0.8298	Intermediate Similarity	NPC471219
0.8286	Intermediate Similarity	NPC476759
0.8286	Intermediate Similarity	NPC112457
0.8286	Intermediate Similarity	NPC474243
0.8283	Intermediate Similarity	NPC471039
0.8283	Intermediate Similarity	NPC473964
0.8273	Intermediate Similarity	NPC469380
0.8269	Intermediate Similarity	NPC216636
0.8269	Intermediate Similarity	NPC475294
0.8269	Intermediate Similarity	NPC319438
0.8265	Intermediate Similarity	NPC471040
0.8265	Intermediate Similarity	NPC140277
0.8265	Intermediate Similarity	NPC476415
0.8261	Intermediate Similarity	NPC200513
0.8257	Intermediate Similarity	NPC134430
0.8257	Intermediate Similarity	NPC475809
0.8257	Intermediate Similarity	NPC473968
0.8257	Intermediate Similarity	NPC284068
0.8252	Intermediate Similarity	NPC118911
0.8252	Intermediate Similarity	NPC470297
0.8252	Intermediate Similarity	NPC189616
0.8247	Intermediate Similarity	NPC72845
0.8247	Intermediate Similarity	NPC329842
0.8247	Intermediate Similarity	NPC177037
0.8247	Intermediate Similarity	NPC472814
0.8247	Intermediate Similarity	NPC289479
0.8241	Intermediate Similarity	NPC470953
0.8235	Intermediate Similarity	NPC32577
0.8235	Intermediate Similarity	NPC58329
0.8235	Intermediate Similarity	NPC475320
0.8235	Intermediate Similarity	NPC22388
0.8235	Intermediate Similarity	NPC155332
0.8235	Intermediate Similarity	NPC469606
0.8235	Intermediate Similarity	NPC136289
0.8235	Intermediate Similarity	NPC472552
0.8235	Intermediate Similarity	NPC273005
0.8235	Intermediate Similarity	NPC31058
0.8235	Intermediate Similarity	NPC114540
0.8229	Intermediate Similarity	NPC170633
0.8229	Intermediate Similarity	NPC116620
0.8224	Intermediate Similarity	NPC476801
0.8218	Intermediate Similarity	NPC16601
0.8218	Intermediate Similarity	NPC476303
0.8218	Intermediate Similarity	NPC38855
0.8218	Intermediate Similarity	NPC472972
0.8218	Intermediate Similarity	NPC476274
0.8211	Intermediate Similarity	NPC175293
0.8208	Intermediate Similarity	NPC5103
0.8208	Intermediate Similarity	NPC253906
0.82	Intermediate Similarity	NPC175351
0.82	Intermediate Similarity	NPC121402
0.82	Intermediate Similarity	NPC132753
0.82	Intermediate Similarity	NPC285513
0.82	Intermediate Similarity	NPC473963
0.82	Intermediate Similarity	NPC151681
0.82	Intermediate Similarity	NPC224356
0.82	Intermediate Similarity	NPC476768
0.82	Intermediate Similarity	NPC254496
0.82	Intermediate Similarity	NPC473456
0.8198	Intermediate Similarity	NPC476962
0.8191	Intermediate Similarity	NPC189311
0.8191	Intermediate Similarity	NPC474013
0.819	Intermediate Similarity	NPC476479
0.819	Intermediate Similarity	NPC476765
0.819	Intermediate Similarity	NPC473483
0.8182	Intermediate Similarity	NPC279974
0.8182	Intermediate Similarity	NPC266899
0.8182	Intermediate Similarity	NPC259042
0.8182	Intermediate Similarity	NPC470229
0.8182	Intermediate Similarity	NPC157686
0.8173	Intermediate Similarity	NPC1679
0.8173	Intermediate Similarity	NPC266570
0.8173	Intermediate Similarity	NPC478052
0.8172	Intermediate Similarity	NPC476927
0.8165	Intermediate Similarity	NPC176840
0.8165	Intermediate Similarity	NPC190286
0.8163	Intermediate Similarity	NPC162615
0.8163	Intermediate Similarity	NPC205034
0.8163	Intermediate Similarity	NPC115021

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 NPC471413 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1463
0.2-0.3	3524
0.3-0.4	2437
0.4-0.5	1015
0.5-0.6	260
0.6-0.7	180
0.7-0.8	98
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8673	High Similarity	NPD7638	Approved
0.8586	High Similarity	NPD7640	Approved
0.8586	High Similarity	NPD7639	Approved
0.8261	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.8019	Intermediate Similarity	NPD6686	Approved
0.7944	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD7748	Approved
0.7885	Intermediate Similarity	NPD7632	Discontinued
0.787	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD6881	Approved
0.785	Intermediate Similarity	NPD6899	Approved
0.7845	Intermediate Similarity	NPD7507	Approved
0.783	Intermediate Similarity	NPD5739	Approved
0.783	Intermediate Similarity	NPD6675	Approved
0.783	Intermediate Similarity	NPD7128	Approved
0.783	Intermediate Similarity	NPD6402	Approved
0.7767	Intermediate Similarity	NPD4225	Approved
0.7757	Intermediate Similarity	NPD5697	Approved
0.7706	Intermediate Similarity	NPD7102	Approved
0.7706	Intermediate Similarity	NPD7290	Approved
0.7706	Intermediate Similarity	NPD6883	Approved
0.77	Intermediate Similarity	NPD7515	Phase 2
0.77	Intermediate Similarity	NPD6079	Approved
0.7685	Intermediate Similarity	NPD6011	Approved
0.7685	Intermediate Similarity	NPD7320	Approved
0.7677	Intermediate Similarity	NPD5328	Approved
0.767	Intermediate Similarity	NPD7902	Approved
0.7664	Intermediate Similarity	NPD6008	Approved
0.7658	Intermediate Similarity	NPD4632	Approved
0.7653	Intermediate Similarity	NPD3573	Approved
0.7647	Intermediate Similarity	NPD7319	Approved
0.7636	Intermediate Similarity	NPD6649	Approved
0.7636	Intermediate Similarity	NPD8130	Phase 1
0.7636	Intermediate Similarity	NPD6617	Approved
0.7636	Intermediate Similarity	NPD6650	Approved
0.7636	Intermediate Similarity	NPD6869	Approved
0.7636	Intermediate Similarity	NPD6847	Approved
0.7629	Intermediate Similarity	NPD1694	Approved
0.7615	Intermediate Similarity	NPD6372	Approved
0.7615	Intermediate Similarity	NPD6014	Approved
0.7615	Intermediate Similarity	NPD6012	Approved
0.7615	Intermediate Similarity	NPD6013	Approved
0.7615	Intermediate Similarity	NPD6373	Approved
0.7611	Intermediate Similarity	NPD7115	Discovery
0.7593	Intermediate Similarity	NPD5701	Approved
0.7593	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD8297	Approved
0.7568	Intermediate Similarity	NPD6882	Approved
0.7477	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6009	Approved
0.7451	Intermediate Similarity	NPD6399	Phase 3
0.7414	Intermediate Similarity	NPD6319	Approved
0.7411	Intermediate Similarity	NPD6053	Discontinued
0.7404	Intermediate Similarity	NPD5221	Approved
0.7404	Intermediate Similarity	NPD5222	Approved
0.7404	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5211	Phase 2
0.7379	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7900	Approved
0.7374	Intermediate Similarity	NPD6409	Approved
0.7374	Intermediate Similarity	NPD7146	Approved
0.7374	Intermediate Similarity	NPD7334	Approved
0.7374	Intermediate Similarity	NPD6684	Approved
0.7374	Intermediate Similarity	NPD3618	Phase 1
0.7374	Intermediate Similarity	NPD7521	Approved
0.7374	Intermediate Similarity	NPD5330	Approved
0.7373	Intermediate Similarity	NPD7604	Phase 2
0.7364	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5286	Approved
0.7358	Intermediate Similarity	NPD5285	Approved
0.7358	Intermediate Similarity	NPD4696	Approved
0.735	Intermediate Similarity	NPD5983	Phase 2
0.7333	Intermediate Similarity	NPD5173	Approved
0.7333	Intermediate Similarity	NPD6083	Phase 2
0.7333	Intermediate Similarity	NPD6084	Phase 2
0.7333	Intermediate Similarity	NPD4755	Approved
0.7311	Intermediate Similarity	NPD7492	Approved
0.729	Intermediate Similarity	NPD5223	Approved
0.7282	Intermediate Similarity	NPD5778	Approved
0.7282	Intermediate Similarity	NPD5779	Approved
0.7265	Intermediate Similarity	NPD6054	Approved
0.725	Intermediate Similarity	NPD6616	Approved
0.725	Intermediate Similarity	NPD6336	Discontinued
0.7248	Intermediate Similarity	NPD5141	Approved
0.7241	Intermediate Similarity	NPD7328	Approved
0.7241	Intermediate Similarity	NPD6335	Approved
0.7241	Intermediate Similarity	NPD7327	Approved
0.7238	Intermediate Similarity	NPD4697	Phase 3
0.7228	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6672	Approved
0.7228	Intermediate Similarity	NPD6903	Approved
0.7228	Intermediate Similarity	NPD5737	Approved
0.7222	Intermediate Similarity	NPD5224	Approved
0.7222	Intermediate Similarity	NPD5226	Approved
0.7222	Intermediate Similarity	NPD4633	Approved
0.7222	Intermediate Similarity	NPD5225	Approved
0.7217	Intermediate Similarity	NPD6868	Approved
0.7217	Intermediate Similarity	NPD6274	Approved
0.7196	Intermediate Similarity	NPD4700	Approved
0.719	Intermediate Similarity	NPD7078	Approved
0.7184	Intermediate Similarity	NPD5693	Phase 1
0.7184	Intermediate Similarity	NPD8035	Phase 2
0.7184	Intermediate Similarity	NPD8034	Phase 2
0.7179	Intermediate Similarity	NPD7516	Approved
0.7179	Intermediate Similarity	NPD7101	Approved
0.7179	Intermediate Similarity	NPD7100	Approved
0.7156	Intermediate Similarity	NPD5174	Approved
0.7156	Intermediate Similarity	NPD5175	Approved
0.7155	Intermediate Similarity	NPD6317	Approved
0.7143	Intermediate Similarity	NPD5695	Phase 3
0.7143	Intermediate Similarity	NPD6370	Approved
0.7143	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD7736	Approved
0.713	Intermediate Similarity	NPD5344	Discontinued
0.7119	Intermediate Similarity	NPD8294	Approved
0.7119	Intermediate Similarity	NPD6059	Approved
0.7119	Intermediate Similarity	NPD8377	Approved
0.7115	Intermediate Similarity	NPD4202	Approved
0.7103	Intermediate Similarity	NPD5696	Approved
0.71	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6314	Approved
0.7094	Intermediate Similarity	NPD6313	Approved
0.7087	Intermediate Similarity	NPD46	Approved
0.7087	Intermediate Similarity	NPD6698	Approved
0.708	Intermediate Similarity	NPD4634	Approved
0.7059	Intermediate Similarity	NPD6015	Approved
0.7059	Intermediate Similarity	NPD8378	Approved
0.7059	Intermediate Similarity	NPD8335	Approved
0.7059	Intermediate Similarity	NPD8380	Approved
0.7059	Intermediate Similarity	NPD8033	Approved
0.7059	Intermediate Similarity	NPD6016	Approved
0.7059	Intermediate Similarity	NPD8379	Approved
0.7059	Intermediate Similarity	NPD8296	Approved
0.7049	Intermediate Similarity	NPD8293	Discontinued
0.7037	Intermediate Similarity	NPD6648	Approved
0.703	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6411	Approved
0.7	Intermediate Similarity	NPD3665	Phase 1
0.7	Intermediate Similarity	NPD4754	Approved
0.7	Intermediate Similarity	NPD4786	Approved
0.7	Intermediate Similarity	NPD3133	Approved
0.7	Intermediate Similarity	NPD5988	Approved
0.7	Intermediate Similarity	NPD3666	Approved
0.699	Remote Similarity	NPD6051	Approved
0.699	Remote Similarity	NPD6673	Approved
0.699	Remote Similarity	NPD6080	Approved
0.699	Remote Similarity	NPD6904	Approved
0.6981	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3667	Approved
0.6964	Remote Similarity	NPD6412	Phase 2
0.6942	Remote Similarity	NPD8328	Phase 3
0.693	Remote Similarity	NPD6371	Approved
0.6923	Remote Similarity	NPD5785	Approved
0.6917	Remote Similarity	NPD7503	Approved
0.6917	Remote Similarity	NPD6909	Approved
0.6917	Remote Similarity	NPD6908	Approved
0.6917	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4729	Approved
0.6903	Remote Similarity	NPD4730	Approved
0.6903	Remote Similarity	NPD5128	Approved
0.6897	Remote Similarity	NPD8133	Approved
0.6875	Remote Similarity	NPD4768	Approved
0.6875	Remote Similarity	NPD4767	Approved
0.6863	Remote Similarity	NPD4623	Approved
0.6863	Remote Similarity	NPD4519	Discontinued
0.6857	Remote Similarity	NPD7637	Suspended
0.6827	Remote Similarity	NPD6101	Approved
0.6827	Remote Similarity	NPD4753	Phase 2
0.6827	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7260	Phase 2
0.6814	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4221	Approved
0.68	Remote Similarity	NPD4223	Phase 3
0.6783	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5251	Approved
0.6783	Remote Similarity	NPD5169	Approved
0.6783	Remote Similarity	NPD5247	Approved
0.6783	Remote Similarity	NPD5248	Approved
0.6783	Remote Similarity	NPD5250	Approved
0.6783	Remote Similarity	NPD5135	Approved
0.6783	Remote Similarity	NPD5249	Phase 3
0.6768	Remote Similarity	NPD4695	Discontinued
0.6768	Remote Similarity	NPD7525	Registered
0.6765	Remote Similarity	NPD5329	Approved
0.6765	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5168	Approved
0.6735	Remote Similarity	NPD6114	Approved
0.6735	Remote Similarity	NPD6115	Approved
0.6735	Remote Similarity	NPD6697	Approved
0.6735	Remote Similarity	NPD6118	Approved
0.6731	Remote Similarity	NPD5208	Approved
0.6729	Remote Similarity	NPD6001	Approved
0.6724	Remote Similarity	NPD5215	Approved
0.6724	Remote Similarity	NPD5127	Approved
0.6724	Remote Similarity	NPD5217	Approved
0.6724	Remote Similarity	NPD5216	Approved
0.672	Remote Similarity	NPD6033	Approved
0.6699	Remote Similarity	NPD6098	Approved
0.6698	Remote Similarity	NPD5281	Approved
0.6698	Remote Similarity	NPD6050	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