NPASS Compound

Structure

NPC189513 OpenBabel07101718322D 28 32 0 0 1 0 0 0 0 0999 V2000 7.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2350 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 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 22 1 0 0 0 0 2 22 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 15 2 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 28 1 0 0 0 0 15 20 1 0 0 0 0 16 22 1 0 0 0 0 16 23 1 1 0 0 0 17 24 1 1 0 0 0 17 25 1 0 0 0 0 18 23 1 1 0 0 0 18 24 1 0 0 0 0 19 25 1 1 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 25 1 1 0 0 0 21 27 1 6 0 0 0 21 28 1 0 0 0 0 23 3 1 1 0 0 0 24 4 1 1 0 0 0 25 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.3
Volume:	421.908
LogP:	5.221
LogD:	4.153
LogS:	-4.932
# Rotatable Bonds:	0
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.579
Synthetic Accessibility Score:	4.994
Fsp3:	0.92
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.7
MDCK Permeability:	1.5464429452549666e-05
Pgp-inhibitor:	0.952
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.935
30% Bioavailability (F30%):	0.031

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.181
Plasma Protein Binding (PPB):	89.36249542236328%
Volume Distribution (VD):	1.799
Pgp-substrate:	11.874696731567383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.263
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.677
CYP2C9-inhibitor:	0.152
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.317
CYP3A4-inhibitor:	0.216
CYP3A4-substrate:	0.168

ADMET: Excretion

Clearance (CL):	7.653
Half-life (T1/2):	0.074

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.122
Drug-inuced Liver Injury (DILI):	0.088
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.549
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.299
Carcinogencity:	0.324
Eye Corrosion:	0.078
Eye Irritation:	0.263
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC189513

Natural Product ID:	NPC189513
*Common Name:**	12-Deacetyl-12-Epi-Deoxoscalarin
IUPAC Name:	(1R,5aS,5bR,7aS,11aS,11bR,13R,13aS,13bS)-5b,8,8,11a,13a-pentamethyl-1,3,5,5a,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydrophenanthro[1,2-g][2]benzofuran-1,13-diol
Synonyms:
Standard InCHIKey:	TVZPMYDGQOHLDW-VKYCOJTLSA-N
Standard InCHI:	InChI=1S/C25H40O3/c1-22(2)10-6-11-23(3)16(22)9-12-24(4)17-8-7-15-14-28-21(27)20(15)25(17,5)19(26)13-18(23)24/h7,16-21,26-27H,6,8-14H2,1-5H3/t16-,17-,18+,19+,20+,21+,23-,24-,25+/m0/s1
SMILES:	CC1(C)CCC[C@@]2(C)[C@H]1CC[C@@]1(C)[C@@H]3CC=C4CO[C@H]([C@@H]4[C@@]3(C)[C@@H](C[C@H]21)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495273
PubChem CID:	10548337
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO33445	glossodoris atromarginata	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	PMID[10543894]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[11809054]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Indian Ocean	n.a.	PMID[16124771]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[16378375]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584401]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Maldives	n.a.	PMID[9873492]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	1.0	ug.mL-1	PMID[535659]

☑ 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 NPC189513 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	195
0.1-0.2	1577
0.2-0.3	4834
0.3-0.4	12085
0.4-0.5	10486
0.5-0.6	5980
0.6-0.7	5014
0.7-0.8	2285
0.8-0.85	206
0.85-0.9	20
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9886	High Similarity	NPC100892
0.9886	High Similarity	NPC135224
0.9886	High Similarity	NPC477970
0.9886	High Similarity	NPC477969
0.9457	High Similarity	NPC477971
0.9457	High Similarity	NPC477972
0.9457	High Similarity	NPC161527
0.9457	High Similarity	NPC20113
0.9457	High Similarity	NPC477968
0.9457	High Similarity	NPC228251
0.9457	High Similarity	NPC219285
0.9101	High Similarity	NPC470819
0.9062	High Similarity	NPC222161
0.9	High Similarity	NPC470817
0.8977	High Similarity	NPC173917
0.8925	High Similarity	NPC94905
0.8925	High Similarity	NPC8954
0.8864	High Similarity	NPC119001
0.866	High Similarity	NPC471889
0.8571	High Similarity	NPC471888
0.8571	High Similarity	NPC471885
0.8571	High Similarity	NPC471450
0.8571	High Similarity	NPC473124
0.8571	High Similarity	NPC471887
0.8571	High Similarity	NPC471886
0.8571	High Similarity	NPC473123
0.8485	Intermediate Similarity	NPC93352
0.8485	Intermediate Similarity	NPC203354
0.8485	Intermediate Similarity	NPC110656
0.8485	Intermediate Similarity	NPC473127
0.8478	Intermediate Similarity	NPC477917
0.8469	Intermediate Similarity	NPC238397
0.8469	Intermediate Similarity	NPC300399
0.8469	Intermediate Similarity	NPC471363
0.8469	Intermediate Similarity	NPC471482
0.8469	Intermediate Similarity	NPC37207
0.8447	Intermediate Similarity	NPC194951
0.8447	Intermediate Similarity	NPC12046
0.8438	Intermediate Similarity	NPC26307
0.8416	Intermediate Similarity	NPC80210
0.8416	Intermediate Similarity	NPC38376
0.8391	Intermediate Similarity	NPC17550
0.8384	Intermediate Similarity	NPC7644
0.8384	Intermediate Similarity	NPC127933
0.8384	Intermediate Similarity	NPC7613
0.8384	Intermediate Similarity	NPC134270
0.8384	Intermediate Similarity	NPC475889
0.8367	Intermediate Similarity	NPC176406
0.8365	Intermediate Similarity	NPC157441
0.8333	Intermediate Similarity	NPC157530
0.8333	Intermediate Similarity	NPC46320
0.8333	Intermediate Similarity	NPC285253
0.8333	Intermediate Similarity	NPC221110
0.8333	Intermediate Similarity	NPC180459
0.8333	Intermediate Similarity	NPC250089
0.8333	Intermediate Similarity	NPC195116
0.8333	Intermediate Similarity	NPC14630
0.8333	Intermediate Similarity	NPC472901
0.8317	Intermediate Similarity	NPC281939
0.8317	Intermediate Similarity	NPC33053
0.8316	Intermediate Similarity	NPC305160
0.8316	Intermediate Similarity	NPC72817
0.8316	Intermediate Similarity	NPC477927
0.8315	Intermediate Similarity	NPC304285
0.8315	Intermediate Similarity	NPC109938
0.8315	Intermediate Similarity	NPC122945
0.83	Intermediate Similarity	NPC473207
0.83	Intermediate Similarity	NPC470321
0.83	Intermediate Similarity	NPC75608
0.83	Intermediate Similarity	NPC264867
0.83	Intermediate Similarity	NPC201880
0.83	Intermediate Similarity	NPC81567
0.8295	Intermediate Similarity	NPC206062
0.8265	Intermediate Similarity	NPC64348
0.8265	Intermediate Similarity	NPC473790
0.8265	Intermediate Similarity	NPC146188
0.8265	Intermediate Similarity	NPC324841
0.8252	Intermediate Similarity	NPC103627
0.8252	Intermediate Similarity	NPC191439
0.8252	Intermediate Similarity	NPC170974
0.8247	Intermediate Similarity	NPC240372
0.8247	Intermediate Similarity	NPC98112
0.8247	Intermediate Similarity	NPC476893
0.8247	Intermediate Similarity	NPC76266
0.8247	Intermediate Similarity	NPC97867
0.8229	Intermediate Similarity	NPC471362
0.8229	Intermediate Similarity	NPC471372
0.8229	Intermediate Similarity	NPC472189
0.8229	Intermediate Similarity	NPC476894
0.8218	Intermediate Similarity	NPC472898
0.8218	Intermediate Similarity	NPC472899
0.8218	Intermediate Similarity	NPC472900
0.8218	Intermediate Similarity	NPC172867
0.8218	Intermediate Similarity	NPC252296
0.8211	Intermediate Similarity	NPC235126
0.8211	Intermediate Similarity	NPC242419
0.8202	Intermediate Similarity	NPC476646
0.82	Intermediate Similarity	NPC162354
0.82	Intermediate Similarity	NPC473198
0.82	Intermediate Similarity	NPC120009
0.8191	Intermediate Similarity	NPC92885
0.8191	Intermediate Similarity	NPC77796
0.8191	Intermediate Similarity	NPC476226
0.8191	Intermediate Similarity	NPC159876
0.8191	Intermediate Similarity	NPC295668
0.8182	Intermediate Similarity	NPC285231
0.8182	Intermediate Similarity	NPC21568
0.8182	Intermediate Similarity	NPC470434
0.8173	Intermediate Similarity	NPC473021
0.8173	Intermediate Similarity	NPC472987
0.8173	Intermediate Similarity	NPC157474
0.8173	Intermediate Similarity	NPC110494
0.8173	Intermediate Similarity	NPC65034
0.8173	Intermediate Similarity	NPC208189
0.8163	Intermediate Similarity	NPC280825
0.8163	Intermediate Similarity	NPC216260
0.8163	Intermediate Similarity	NPC234287
0.8163	Intermediate Similarity	NPC5358
0.8163	Intermediate Similarity	NPC476895
0.8155	Intermediate Similarity	NPC473318
0.8155	Intermediate Similarity	NPC28844
0.8155	Intermediate Similarity	NPC473328
0.8152	Intermediate Similarity	NPC323209
0.8144	Intermediate Similarity	NPC171598
0.8144	Intermediate Similarity	NPC90583
0.8137	Intermediate Similarity	NPC109376
0.8137	Intermediate Similarity	NPC88013
0.8137	Intermediate Similarity	NPC125423
0.8137	Intermediate Similarity	NPC110496
0.8137	Intermediate Similarity	NPC184512
0.8132	Intermediate Similarity	NPC319238
0.8125	Intermediate Similarity	NPC144202
0.8111	Intermediate Similarity	NPC155521
0.8111	Intermediate Similarity	NPC470049
0.8111	Intermediate Similarity	NPC248886
0.8105	Intermediate Similarity	NPC234335
0.81	Intermediate Similarity	NPC136816
0.8095	Intermediate Similarity	NPC476305
0.8095	Intermediate Similarity	NPC231797
0.8095	Intermediate Similarity	NPC473125
0.809	Intermediate Similarity	NPC96362
0.8085	Intermediate Similarity	NPC473058
0.8085	Intermediate Similarity	NPC293044
0.8081	Intermediate Similarity	NPC473200
0.8081	Intermediate Similarity	NPC324598
0.8081	Intermediate Similarity	NPC477716
0.8081	Intermediate Similarity	NPC469942
0.8081	Intermediate Similarity	NPC7341
0.8081	Intermediate Similarity	NPC477721
0.8081	Intermediate Similarity	NPC282669
0.8077	Intermediate Similarity	NPC65155
0.8065	Intermediate Similarity	NPC476948
0.8061	Intermediate Similarity	NPC243728
0.8061	Intermediate Similarity	NPC477718
0.8061	Intermediate Similarity	NPC477719
0.8061	Intermediate Similarity	NPC472188
0.8061	Intermediate Similarity	NPC51499
0.8061	Intermediate Similarity	NPC473890
0.8061	Intermediate Similarity	NPC177818
0.8058	Intermediate Similarity	NPC128795
0.8058	Intermediate Similarity	NPC217921
0.8058	Intermediate Similarity	NPC311223
0.8058	Intermediate Similarity	NPC224660
0.8058	Intermediate Similarity	NPC325054
0.8058	Intermediate Similarity	NPC135015
0.8058	Intermediate Similarity	NPC48548
0.8058	Intermediate Similarity	NPC189075
0.8058	Intermediate Similarity	NPC275539
0.8058	Intermediate Similarity	NPC470024
0.8058	Intermediate Similarity	NPC38948
0.8043	Intermediate Similarity	NPC308041
0.8043	Intermediate Similarity	NPC477578
0.8043	Intermediate Similarity	NPC16350
0.8041	Intermediate Similarity	NPC8774
0.8039	Intermediate Similarity	NPC218158
0.8039	Intermediate Similarity	NPC470055
0.8039	Intermediate Similarity	NPC470056
0.8021	Intermediate Similarity	NPC474792
0.8021	Intermediate Similarity	NPC27531
0.8021	Intermediate Similarity	NPC91654
0.8021	Intermediate Similarity	NPC67398
0.802	Intermediate Similarity	NPC213190
0.802	Intermediate Similarity	NPC281378
0.802	Intermediate Similarity	NPC99627
0.802	Intermediate Similarity	NPC45897
0.802	Intermediate Similarity	NPC473129
0.8019	Intermediate Similarity	NPC40133
0.8019	Intermediate Similarity	NPC44298
0.8019	Intermediate Similarity	NPC49413
0.8019	Intermediate Similarity	NPC473128
0.8019	Intermediate Similarity	NPC290608
0.8	Intermediate Similarity	NPC7505
0.8	Intermediate Similarity	NPC474683
0.8	Intermediate Similarity	NPC129372
0.8	Intermediate Similarity	NPC88000
0.8	Intermediate Similarity	NPC4831
0.8	Intermediate Similarity	NPC474752
0.8	Intermediate Similarity	NPC475617
0.8	Intermediate Similarity	NPC160734
0.8	Intermediate Similarity	NPC471432

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 NPC189513 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1686
0.2-0.3	3957
0.3-0.4	2251
0.4-0.5	627
0.5-0.6	240
0.6-0.7	180
0.7-0.8	28
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
0.78	Intermediate Similarity	NPD7638	Approved
0.7778	Intermediate Similarity	NPD7645	Phase 2
0.7723	Intermediate Similarity	NPD7639	Approved
0.7723	Intermediate Similarity	NPD7640	Approved
0.7568	Intermediate Similarity	NPD7327	Approved
0.7568	Intermediate Similarity	NPD7328	Approved
0.7522	Intermediate Similarity	NPD8033	Approved
0.75	Intermediate Similarity	NPD7516	Approved
0.75	Intermediate Similarity	NPD7525	Registered
0.7434	Intermediate Similarity	NPD8377	Approved
0.7434	Intermediate Similarity	NPD8294	Approved
0.7368	Intermediate Similarity	NPD8380	Approved
0.7368	Intermediate Similarity	NPD8296	Approved
0.7368	Intermediate Similarity	NPD8335	Approved
0.7368	Intermediate Similarity	NPD8379	Approved
0.7368	Intermediate Similarity	NPD8378	Approved
0.7333	Intermediate Similarity	NPD6942	Approved
0.7333	Intermediate Similarity	NPD7339	Approved
0.7253	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6686	Approved
0.7217	Intermediate Similarity	NPD7503	Approved
0.7143	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6412	Phase 2
0.7119	Intermediate Similarity	NPD7507	Approved
0.7075	Intermediate Similarity	NPD7632	Discontinued
0.701	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD4225	Approved
0.6947	Remote Similarity	NPD6928	Phase 2
0.6942	Remote Similarity	NPD7319	Approved
0.6907	Remote Similarity	NPD6695	Phase 3
0.6903	Remote Similarity	NPD8133	Approved
0.6893	Remote Similarity	NPD7748	Approved
0.6863	Remote Similarity	NPD7515	Phase 2
0.6857	Remote Similarity	NPD7902	Approved
0.6847	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6929	Approved
0.6837	Remote Similarity	NPD4786	Approved
0.6837	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD3667	Approved
0.6796	Remote Similarity	NPD6399	Phase 3
0.6774	Remote Similarity	NPD8264	Approved
0.6771	Remote Similarity	NPD6930	Phase 2
0.6771	Remote Similarity	NPD6931	Approved
0.6724	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6370	Approved
0.6721	Remote Similarity	NPD7736	Approved
0.67	Remote Similarity	NPD3618	Phase 1
0.6696	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD6051	Approved
0.6639	Remote Similarity	NPD8516	Approved
0.6639	Remote Similarity	NPD8517	Approved
0.6639	Remote Similarity	NPD8515	Approved
0.6639	Remote Similarity	NPD8513	Phase 3
0.6634	Remote Similarity	NPD7524	Approved
0.6634	Remote Similarity	NPD7750	Discontinued
0.6632	Remote Similarity	NPD6925	Approved
0.6632	Remote Similarity	NPD5776	Phase 2
0.66	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7514	Phase 3
0.6598	Remote Similarity	NPD7332	Phase 2
0.6598	Remote Similarity	NPD7509	Discontinued
0.6581	Remote Similarity	NPD7115	Discovery
0.6571	Remote Similarity	NPD7900	Approved
0.6571	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7145	Approved
0.6555	Remote Similarity	NPD6054	Approved
0.6555	Remote Similarity	NPD6059	Approved
0.6538	Remote Similarity	NPD8035	Phase 2
0.6538	Remote Similarity	NPD6079	Approved
0.6538	Remote Similarity	NPD8034	Phase 2
0.6531	Remote Similarity	NPD6902	Approved
0.6526	Remote Similarity	NPD6933	Approved
0.6514	Remote Similarity	NPD5344	Discontinued
0.6514	Remote Similarity	NPD4159	Approved
0.6504	Remote Similarity	NPD8293	Discontinued
0.6491	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4784	Approved
0.6489	Remote Similarity	NPD4785	Approved
0.6476	Remote Similarity	NPD4202	Approved
0.6476	Remote Similarity	NPD8171	Discontinued
0.6458	Remote Similarity	NPD6932	Approved
0.6452	Remote Similarity	NPD4243	Approved
0.6452	Remote Similarity	NPD7150	Approved
0.6452	Remote Similarity	NPD7151	Approved
0.6452	Remote Similarity	NPD7152	Approved
0.6436	Remote Similarity	NPD6893	Approved
0.6429	Remote Similarity	NPD6675	Approved
0.6429	Remote Similarity	NPD6402	Approved
0.6429	Remote Similarity	NPD6008	Approved
0.6429	Remote Similarity	NPD5739	Approved
0.6429	Remote Similarity	NPD7128	Approved
0.6429	Remote Similarity	NPD4748	Discontinued
0.6413	Remote Similarity	NPD6923	Approved
0.6413	Remote Similarity	NPD6922	Approved
0.6408	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7637	Suspended
0.6381	Remote Similarity	NPD7087	Discontinued
0.6379	Remote Similarity	NPD6882	Approved
0.6364	Remote Similarity	NPD6015	Approved
0.6364	Remote Similarity	NPD6898	Phase 1
0.6364	Remote Similarity	NPD6016	Approved
0.6344	Remote Similarity	NPD7144	Approved
0.6344	Remote Similarity	NPD7143	Approved
0.6341	Remote Similarity	NPD7492	Approved
0.6337	Remote Similarity	NPD3133	Approved
0.6337	Remote Similarity	NPD3665	Phase 1
0.6337	Remote Similarity	NPD3666	Approved
0.6327	Remote Similarity	NPD6683	Phase 2
0.6316	Remote Similarity	NPD6881	Approved
0.6316	Remote Similarity	NPD7320	Approved
0.6316	Remote Similarity	NPD6899	Approved
0.6311	Remote Similarity	NPD5988	Approved
0.6303	Remote Similarity	NPD6009	Approved
0.629	Remote Similarity	NPD6616	Approved
0.6286	Remote Similarity	NPD3168	Discontinued
0.6275	Remote Similarity	NPD1694	Approved
0.6273	Remote Similarity	NPD6648	Approved
0.6261	Remote Similarity	NPD6372	Approved
0.6261	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD8449	Approved
0.624	Remote Similarity	NPD7078	Approved
0.6239	Remote Similarity	NPD4755	Approved
0.6239	Remote Similarity	NPD6053	Discontinued
0.6228	Remote Similarity	NPD5701	Approved
0.6228	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5697	Approved
0.6214	Remote Similarity	NPD6684	Approved
0.6214	Remote Similarity	NPD7334	Approved
0.6214	Remote Similarity	NPD5330	Approved
0.6214	Remote Similarity	NPD7146	Approved
0.6214	Remote Similarity	NPD6409	Approved
0.6214	Remote Similarity	NPD7521	Approved
0.6207	Remote Similarity	NPD6883	Approved
0.6207	Remote Similarity	NPD7290	Approved
0.6207	Remote Similarity	NPD7102	Approved
0.6202	Remote Similarity	NPD8450	Suspended
0.619	Remote Similarity	NPD6033	Approved
0.6186	Remote Similarity	NPD4632	Approved
0.618	Remote Similarity	NPD368	Approved
0.6176	Remote Similarity	NPD3668	Phase 3
0.6174	Remote Similarity	NPD6011	Approved
0.6174	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5779	Approved
0.6168	Remote Similarity	NPD5778	Approved
0.6161	Remote Similarity	NPD5211	Phase 2
0.6154	Remote Similarity	NPD6869	Approved
0.6154	Remote Similarity	NPD6650	Approved
0.6154	Remote Similarity	NPD8130	Phase 1
0.6154	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6617	Approved
0.6154	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6649	Approved
0.6154	Remote Similarity	NPD6847	Approved
0.6147	Remote Similarity	NPD5222	Approved
0.6147	Remote Similarity	NPD5221	Approved
0.6147	Remote Similarity	NPD4697	Phase 3
0.6147	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD7625	Phase 1
0.6126	Remote Similarity	NPD4696	Approved
0.6126	Remote Similarity	NPD5286	Approved
0.6126	Remote Similarity	NPD5285	Approved
0.6126	Remote Similarity	NPD4700	Approved
0.6121	Remote Similarity	NPD6012	Approved
0.6121	Remote Similarity	NPD6014	Approved
0.6121	Remote Similarity	NPD6013	Approved
0.6102	Remote Similarity	NPD8297	Approved
0.6095	Remote Similarity	NPD6903	Approved
0.6091	Remote Similarity	NPD6083	Phase 2
0.6091	Remote Similarity	NPD6084	Phase 2
0.6091	Remote Similarity	NPD5173	Approved
0.6082	Remote Similarity	NPD5275	Approved
0.6082	Remote Similarity	NPD4190	Phase 3
0.6075	Remote Similarity	NPD6411	Approved
0.6071	Remote Similarity	NPD5223	Approved
0.6053	Remote Similarity	NPD5141	Approved
0.6048	Remote Similarity	NPD5125	Phase 3
0.6048	Remote Similarity	NPD5126	Approved
0.6036	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD5290	Discontinued
0.6018	Remote Similarity	NPD5225	Approved
0.6018	Remote Similarity	NPD5226	Approved
0.6018	Remote Similarity	NPD4633	Approved
0.6018	Remote Similarity	NPD5224	Approved
0.6016	Remote Similarity	NPD6319	Approved
0.6016	Remote Similarity	NPD7741	Discontinued
0.6	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD4195	Approved
0.6	Remote Similarity	NPD3573	Approved
0.6	Remote Similarity	NPD6640	Phase 3
0.5984	Remote Similarity	NPD8074	Phase 3
0.5981	Remote Similarity	NPD46	Approved
0.5981	Remote Similarity	NPD6698	Approved
0.5981	Remote Similarity	NPD7838	Discovery

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