NPASS Compound

Structure

NPC219516 OpenBabel07101718222D 35 38 0 0 1 0 0 0 0 0999 V2000 -6.1235 5.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7707 4.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1527 2.6896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 4.5032 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 -2.1913 3.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5054 3.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 3.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7926 4.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4836 3.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 3.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 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 -3.5491 2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 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 -2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 2 0 0 0 0 5 21 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 27 1 0 0 0 0 16 22 1 0 0 0 0 16 30 1 0 0 0 0 17 29 1 0 0 0 0 17 35 1 0 0 0 0 18 19 1 0 0 0 0 20 4 1 1 0 0 0 20 24 1 0 0 0 0 21 31 2 0 0 0 0 21 35 1 0 0 0 0 22 32 1 6 0 0 0 23 15 1 1 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 24 28 1 6 0 0 0 25 28 1 6 0 0 0 26 29 1 6 0 0 0 27 30 1 6 0 0 0 27 33 1 0 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.37
Volume:	531.888
LogP:	5.051
LogD:	4.863
LogS:	-4.798
# Rotatable Bonds:	8
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.335
Synthetic Accessibility Score:	4.933
Fsp3:	0.9
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:	-4.75
MDCK Permeability:	3.2223026209976524e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.977
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.552
30% Bioavailability (F30%):	0.04

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.143
Plasma Protein Binding (PPB):	94.31720733642578%
Volume Distribution (VD):	0.9
Pgp-substrate:	2.5277273654937744%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.158
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.785
CYP2C9-inhibitor:	0.234
CYP2C9-substrate:	0.178
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.817
CYP3A4-substrate:	0.381

ADMET: Excretion

Clearance (CL):	5.209
Half-life (T1/2):	0.238

ADMET: Toxicity

hERG Blockers:	0.644
Human Hepatotoxicity (H-HT):	0.176
Drug-inuced Liver Injury (DILI):	0.738
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.313
Skin Sensitization:	0.933
Carcinogencity:	0.129
Eye Corrosion:	0.028
Eye Irritation:	0.221
Respiratory Toxicity:	0.903

Download Data

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

Natural Product: NPC219516

Natural Product ID:	NPC219516
*Common Name:**	Armatinol B
IUPAC Name:	[(3S,5R,6R,8S,9S,10R,13R,14S,17R)-3,5,6-trihydroxy-13-methyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-10-yl]methyl acetate
Synonyms:	Armatinol B
Standard InCHIKey:	LAVASOSSYAPADQ-WVMCKFTRSA-N
Standard InCHI:	InChI=1S/C30H50O5/c1-18(2)19(3)7-8-20(4)24-9-10-25-23-15-27(33)30(34)16-22(32)11-14-29(30,17-35-21(5)31)26(23)12-13-28(24,25)6/h18,20,22-27,32-34H,3,7-17H2,1-2,4-6H3/t20-,22+,23+,24-,25+,26+,27-,28-,29+,30+/m1/s1
SMILES:	CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@H]([C@]4(C[C@H](CC[C@]4(COC(=O)C)[C@H]3CC[C@]12C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463369
PubChem CID:	11386309
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO21076	Nephthea armata	Species	Nephtheidae	Eukaryota	n.a.	Taiwan	n.a.	PMID[15387641]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121250]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	Hainan soft coral	n.a.	PMID[23357636]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21076	Nephthea armata	Species	Nephtheidae	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	2
Others	1

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	3200.0	nM	PMID[448411]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	3100.0	nM	PMID[448411]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC50	=	15600.0	nM	PMID[448412]

☑ 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 NPC219516 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	1809
0.2-0.3	5942
0.3-0.4	13939
0.4-0.5	7989
0.5-0.6	4782
0.6-0.7	5086
0.7-0.8	2667
0.8-0.85	231
0.85-0.9	30
0.9-0.95	19
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9425	High Similarity	NPC10274
0.9176	High Similarity	NPC299963
0.9121	High Similarity	NPC169270
0.9121	High Similarity	NPC292718
0.9121	High Similarity	NPC471903
0.9121	High Similarity	NPC111834
0.9121	High Similarity	NPC306797
0.9059	High Similarity	NPC211135
0.9059	High Similarity	NPC85095
0.9059	High Similarity	NPC216420
0.9022	High Similarity	NPC274793
0.9011	High Similarity	NPC241047
0.8989	High Similarity	NPC53890
0.8989	High Similarity	NPC123252
0.8989	High Similarity	NPC219937
0.8989	High Similarity	NPC194485
0.8977	High Similarity	NPC473436
0.8941	High Similarity	NPC472504
0.8941	High Similarity	NPC154043
0.8941	High Similarity	NPC60018
0.8941	High Similarity	NPC202688
0.8936	High Similarity	NPC49532
0.8925	High Similarity	NPC300179
0.8925	High Similarity	NPC102426
0.8889	High Similarity	NPC130840
0.8851	High Similarity	NPC266651
0.8791	High Similarity	NPC26046
0.8764	High Similarity	NPC160304
0.875	High Similarity	NPC121981
0.8737	High Similarity	NPC289670
0.8736	High Similarity	NPC86238
0.8706	High Similarity	NPC206735
0.8696	High Similarity	NPC3359
0.8696	High Similarity	NPC277399
0.8632	High Similarity	NPC208358
0.8632	High Similarity	NPC317019
0.8617	High Similarity	NPC475032
0.8617	High Similarity	NPC475033
0.8617	High Similarity	NPC253586
0.8587	High Similarity	NPC291373
0.8542	High Similarity	NPC475617
0.8542	High Similarity	NPC155974
0.8539	High Similarity	NPC215968
0.8539	High Similarity	NPC155531
0.8526	High Similarity	NPC470066
0.8526	High Similarity	NPC470068
0.8526	High Similarity	NPC477875
0.8526	High Similarity	NPC119036
0.8526	High Similarity	NPC477876
0.8526	High Similarity	NPC469725
0.8526	High Similarity	NPC470067
0.8523	High Similarity	NPC255882
0.85	High Similarity	NPC473570
0.8471	Intermediate Similarity	NPC31828
0.8469	Intermediate Similarity	NPC301787
0.8454	Intermediate Similarity	NPC177701
0.8454	Intermediate Similarity	NPC31085
0.8444	Intermediate Similarity	NPC477600
0.8438	Intermediate Similarity	NPC108371
0.8427	Intermediate Similarity	NPC164424
0.8421	Intermediate Similarity	NPC471770
0.8421	Intermediate Similarity	NPC473555
0.8421	Intermediate Similarity	NPC278939
0.8421	Intermediate Similarity	NPC210337
0.8409	Intermediate Similarity	NPC5280
0.8409	Intermediate Similarity	NPC232023
0.8409	Intermediate Similarity	NPC473742
0.8384	Intermediate Similarity	NPC222833
0.8384	Intermediate Similarity	NPC473199
0.8367	Intermediate Similarity	NPC473523
0.8367	Intermediate Similarity	NPC471467
0.8367	Intermediate Similarity	NPC474124
0.8351	Intermediate Similarity	NPC144486
0.8351	Intermediate Similarity	NPC470054
0.8333	Intermediate Similarity	NPC28864
0.8333	Intermediate Similarity	NPC20479
0.8333	Intermediate Similarity	NPC157739
0.8333	Intermediate Similarity	NPC477283
0.8333	Intermediate Similarity	NPC168231
0.8333	Intermediate Similarity	NPC162459
0.8333	Intermediate Similarity	NPC38471
0.8333	Intermediate Similarity	NPC98837
0.8333	Intermediate Similarity	NPC38296
0.8317	Intermediate Similarity	NPC154085
0.8317	Intermediate Similarity	NPC296761
0.8317	Intermediate Similarity	NPC125361
0.8317	Intermediate Similarity	NPC51925
0.8317	Intermediate Similarity	NPC43976
0.8316	Intermediate Similarity	NPC304899
0.8316	Intermediate Similarity	NPC472989
0.8316	Intermediate Similarity	NPC253115
0.8316	Intermediate Similarity	NPC88009
0.83	Intermediate Similarity	NPC166993
0.8298	Intermediate Similarity	NPC39453
0.8283	Intermediate Similarity	NPC31430
0.8283	Intermediate Similarity	NPC473543
0.8283	Intermediate Similarity	NPC85593
0.828	Intermediate Similarity	NPC210268
0.8276	Intermediate Similarity	NPC475679
0.8265	Intermediate Similarity	NPC476471
0.8265	Intermediate Similarity	NPC52585
0.8265	Intermediate Similarity	NPC475344
0.8265	Intermediate Similarity	NPC470053
0.8265	Intermediate Similarity	NPC68630
0.8265	Intermediate Similarity	NPC228049
0.8261	Intermediate Similarity	NPC109744
0.8261	Intermediate Similarity	NPC220498
0.8247	Intermediate Similarity	NPC293866
0.8247	Intermediate Similarity	NPC477655
0.8247	Intermediate Similarity	NPC473510
0.8247	Intermediate Similarity	NPC94906
0.8247	Intermediate Similarity	NPC230546
0.8247	Intermediate Similarity	NPC477656
0.8242	Intermediate Similarity	NPC5943
0.8235	Intermediate Similarity	NPC91573
0.8229	Intermediate Similarity	NPC476021
0.8229	Intermediate Similarity	NPC170978
0.8229	Intermediate Similarity	NPC474994
0.8229	Intermediate Similarity	NPC316604
0.8229	Intermediate Similarity	NPC476040
0.8218	Intermediate Similarity	NPC472988
0.8218	Intermediate Similarity	NPC472218
0.8218	Intermediate Similarity	NPC231278
0.8218	Intermediate Similarity	NPC472219
0.8218	Intermediate Similarity	NPC472217
0.8218	Intermediate Similarity	NPC112895
0.8218	Intermediate Similarity	NPC218123
0.8218	Intermediate Similarity	NPC38217
0.8218	Intermediate Similarity	NPC273155
0.8218	Intermediate Similarity	NPC473517
0.8211	Intermediate Similarity	NPC279974
0.8202	Intermediate Similarity	NPC207013
0.8202	Intermediate Similarity	NPC470929
0.8202	Intermediate Similarity	NPC111582
0.8202	Intermediate Similarity	NPC477285
0.82	Intermediate Similarity	NPC165405
0.82	Intermediate Similarity	NPC186668
0.82	Intermediate Similarity	NPC138908
0.82	Intermediate Similarity	NPC200957
0.8182	Intermediate Similarity	NPC10232
0.8182	Intermediate Similarity	NPC97487
0.8182	Intermediate Similarity	NPC189588
0.8182	Intermediate Similarity	NPC73515
0.8182	Intermediate Similarity	NPC209298
0.8182	Intermediate Similarity	NPC277074
0.8182	Intermediate Similarity	NPC187302
0.8182	Intermediate Similarity	NPC472821
0.8182	Intermediate Similarity	NPC196471
0.8172	Intermediate Similarity	NPC473956
0.8172	Intermediate Similarity	NPC475751
0.8163	Intermediate Similarity	NPC252614
0.8163	Intermediate Similarity	NPC121218
0.8163	Intermediate Similarity	NPC46848
0.8163	Intermediate Similarity	NPC235920
0.8163	Intermediate Similarity	NPC96784
0.8163	Intermediate Similarity	NPC253886
0.8161	Intermediate Similarity	NPC475727
0.8161	Intermediate Similarity	NPC116119
0.8161	Intermediate Similarity	NPC80297
0.8161	Intermediate Similarity	NPC476176
0.8161	Intermediate Similarity	NPC472742
0.8155	Intermediate Similarity	NPC65167
0.8152	Intermediate Similarity	NPC255176
0.8144	Intermediate Similarity	NPC89099
0.8144	Intermediate Similarity	NPC472028
0.8137	Intermediate Similarity	NPC240125
0.8137	Intermediate Similarity	NPC91583
0.8132	Intermediate Similarity	NPC201273
0.8132	Intermediate Similarity	NPC269058
0.8132	Intermediate Similarity	NPC131365
0.8132	Intermediate Similarity	NPC71520
0.8132	Intermediate Similarity	NPC474970
0.8125	Intermediate Similarity	NPC29410
0.8125	Intermediate Similarity	NPC200054
0.8125	Intermediate Similarity	NPC256227
0.8125	Intermediate Similarity	NPC299654
0.8119	Intermediate Similarity	NPC470170
0.8119	Intermediate Similarity	NPC234160
0.8119	Intermediate Similarity	NPC59530
0.8119	Intermediate Similarity	NPC470169
0.8118	Intermediate Similarity	NPC158208
0.8118	Intermediate Similarity	NPC3403
0.8118	Intermediate Similarity	NPC243027
0.8118	Intermediate Similarity	NPC196136
0.8105	Intermediate Similarity	NPC47853
0.81	Intermediate Similarity	NPC470062
0.81	Intermediate Similarity	NPC470043
0.81	Intermediate Similarity	NPC470061
0.81	Intermediate Similarity	NPC470060
0.81	Intermediate Similarity	NPC470064
0.81	Intermediate Similarity	NPC470059
0.81	Intermediate Similarity	NPC470057
0.81	Intermediate Similarity	NPC470058
0.81	Intermediate Similarity	NPC475521
0.809	Intermediate Similarity	NPC477447
0.809	Intermediate Similarity	NPC470155
0.809	Intermediate Similarity	NPC477446
0.809	Intermediate Similarity	NPC477286
0.809	Intermediate Similarity	NPC286719
0.8081	Intermediate Similarity	NPC124544

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 NPC219516 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	2205
0.2-0.3	4094
0.3-0.4	1773
0.4-0.5	454
0.5-0.6	184
0.6-0.7	211
0.7-0.8	51
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
0.7895	Intermediate Similarity	NPD8034	Phase 2
0.7895	Intermediate Similarity	NPD8035	Phase 2
0.7865	Intermediate Similarity	NPD7525	Registered
0.7826	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7516	Approved
0.7778	Intermediate Similarity	NPD7638	Approved
0.7706	Intermediate Similarity	NPD7328	Approved
0.7706	Intermediate Similarity	NPD7327	Approved
0.77	Intermediate Similarity	NPD7640	Approved
0.77	Intermediate Similarity	NPD7639	Approved
0.7529	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8335	Approved
0.75	Intermediate Similarity	NPD8380	Approved
0.75	Intermediate Similarity	NPD8379	Approved
0.75	Intermediate Similarity	NPD8133	Approved
0.75	Intermediate Similarity	NPD8378	Approved
0.75	Intermediate Similarity	NPD8296	Approved
0.7474	Intermediate Similarity	NPD7524	Approved
0.7444	Intermediate Similarity	NPD6118	Approved
0.7444	Intermediate Similarity	NPD6115	Approved
0.7444	Intermediate Similarity	NPD6114	Approved
0.7444	Intermediate Similarity	NPD6697	Approved
0.7411	Intermediate Similarity	NPD8377	Approved
0.7411	Intermediate Similarity	NPD8294	Approved
0.7358	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8033	Approved
0.734	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7128	Approved
0.7333	Intermediate Similarity	NPD6116	Phase 1
0.7333	Intermediate Similarity	NPD5739	Approved
0.7333	Intermediate Similarity	NPD6675	Approved
0.7333	Intermediate Similarity	NPD6402	Approved
0.729	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6399	Phase 3
0.7234	Intermediate Similarity	NPD6695	Phase 3
0.7222	Intermediate Similarity	NPD6117	Approved
0.7212	Intermediate Similarity	NPD7632	Discontinued
0.7196	Intermediate Similarity	NPD6899	Approved
0.7196	Intermediate Similarity	NPD6881	Approved
0.7196	Intermediate Similarity	NPD7320	Approved
0.7182	Intermediate Similarity	NPD4632	Approved
0.713	Intermediate Similarity	NPD6373	Approved
0.713	Intermediate Similarity	NPD6372	Approved
0.7105	Intermediate Similarity	NPD6319	Approved
0.7103	Intermediate Similarity	NPD5697	Approved
0.7103	Intermediate Similarity	NPD5701	Approved
0.7094	Intermediate Similarity	NPD7507	Approved
0.7091	Intermediate Similarity	NPD8297	Approved
0.7064	Intermediate Similarity	NPD7102	Approved
0.7064	Intermediate Similarity	NPD7290	Approved
0.7064	Intermediate Similarity	NPD6883	Approved
0.7059	Intermediate Similarity	NPD7319	Approved
0.7043	Intermediate Similarity	NPD7503	Approved
0.7	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6869	Approved
0.7	Intermediate Similarity	NPD8130	Phase 1
0.7	Intermediate Similarity	NPD6649	Approved
0.7	Intermediate Similarity	NPD6617	Approved
0.7	Intermediate Similarity	NPD7637	Suspended
0.7	Intermediate Similarity	NPD6650	Approved
0.7	Intermediate Similarity	NPD6847	Approved
0.699	Remote Similarity	NPD6084	Phase 2
0.699	Remote Similarity	NPD6083	Phase 2
0.6989	Remote Similarity	NPD7645	Phase 2
0.6972	Remote Similarity	NPD6014	Approved
0.6972	Remote Similarity	NPD6012	Approved
0.6972	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6013	Approved
0.6952	Remote Similarity	NPD5344	Discontinued
0.6944	Remote Similarity	NPD6412	Phase 2
0.6939	Remote Similarity	NPD7750	Discontinued
0.6937	Remote Similarity	NPD6882	Approved
0.6923	Remote Similarity	NPD7339	Approved
0.6923	Remote Similarity	NPD6942	Approved
0.6915	Remote Similarity	NPD6928	Phase 2
0.6915	Remote Similarity	NPD6931	Approved
0.6915	Remote Similarity	NPD6930	Phase 2
0.6909	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6011	Approved
0.6875	Remote Similarity	NPD4788	Approved
0.6864	Remote Similarity	NPD7492	Approved
0.6863	Remote Similarity	NPD7748	Approved
0.6852	Remote Similarity	NPD6008	Approved
0.6848	Remote Similarity	NPD6933	Approved
0.6847	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7115	Discovery
0.6842	Remote Similarity	NPD6009	Approved
0.6833	Remote Similarity	NPD7736	Approved
0.6832	Remote Similarity	NPD7515	Phase 2
0.6827	Remote Similarity	NPD7902	Approved
0.6827	Remote Similarity	NPD4755	Approved
0.681	Remote Similarity	NPD6054	Approved
0.681	Remote Similarity	NPD6059	Approved
0.6809	Remote Similarity	NPD6929	Approved
0.6807	Remote Similarity	NPD6616	Approved
0.6804	Remote Similarity	NPD4786	Approved
0.68	Remote Similarity	NPD6051	Approved
0.68	Remote Similarity	NPD5328	Approved
0.678	Remote Similarity	NPD7604	Phase 2
0.6774	Remote Similarity	NPD6932	Approved
0.6765	Remote Similarity	NPD4202	Approved
0.6765	Remote Similarity	NPD8171	Discontinued
0.6762	Remote Similarity	NPD4225	Approved
0.6757	Remote Similarity	NPD4634	Approved
0.6752	Remote Similarity	NPD5983	Phase 2
0.675	Remote Similarity	NPD7078	Approved
0.675	Remote Similarity	NPD8293	Discontinued
0.6727	Remote Similarity	NPD6686	Approved
0.6698	Remote Similarity	NPD5286	Approved
0.6698	Remote Similarity	NPD5285	Approved
0.6698	Remote Similarity	NPD4700	Approved
0.6698	Remote Similarity	NPD4696	Approved
0.6695	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD7087	Discontinued
0.6667	Remote Similarity	NPD6079	Approved
0.6636	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5695	Phase 3
0.6632	Remote Similarity	NPD6683	Phase 2
0.663	Remote Similarity	NPD6926	Approved
0.663	Remote Similarity	NPD6924	Approved
0.661	Remote Similarity	NPD6921	Approved
0.661	Remote Similarity	NPD6016	Approved
0.661	Remote Similarity	NPD6015	Approved
0.6609	Remote Similarity	NPD6274	Approved
0.6604	Remote Similarity	NPD5696	Approved
0.66	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD3667	Approved
0.6596	Remote Similarity	NPD5776	Phase 2
0.6596	Remote Similarity	NPD6925	Approved
0.6593	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7100	Approved
0.6581	Remote Similarity	NPD7101	Approved
0.6574	Remote Similarity	NPD5226	Approved
0.6574	Remote Similarity	NPD5225	Approved
0.6574	Remote Similarity	NPD4633	Approved
0.6574	Remote Similarity	NPD5224	Approved
0.6574	Remote Similarity	NPD5211	Phase 2
0.6566	Remote Similarity	NPD6893	Approved
0.6562	Remote Similarity	NPD7514	Phase 3
0.6559	Remote Similarity	NPD3703	Phase 2
0.6555	Remote Similarity	NPD5988	Approved
0.6552	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD371	Approved
0.6542	Remote Similarity	NPD6648	Approved
0.6538	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7900	Approved
0.6535	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6672	Approved
0.6535	Remote Similarity	NPD5737	Approved
0.6526	Remote Similarity	NPD7145	Approved
0.6514	Remote Similarity	NPD5175	Approved
0.6514	Remote Similarity	NPD5174	Approved
0.65	Remote Similarity	NPD7334	Approved
0.65	Remote Similarity	NPD7521	Approved
0.65	Remote Similarity	NPD6409	Approved
0.65	Remote Similarity	NPD6684	Approved
0.65	Remote Similarity	NPD7146	Approved
0.65	Remote Similarity	NPD5330	Approved
0.65	Remote Similarity	NPD8328	Phase 3
0.6496	Remote Similarity	NPD6335	Approved
0.6484	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4787	Phase 1
0.6481	Remote Similarity	NPD4159	Approved
0.6481	Remote Similarity	NPD5223	Approved
0.6476	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6909	Approved
0.6471	Remote Similarity	NPD4753	Phase 2
0.6471	Remote Similarity	NPD6908	Approved
0.6455	Remote Similarity	NPD5141	Approved
0.6455	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5221	Approved
0.6415	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4697	Phase 3
0.6415	Remote Similarity	NPD5222	Approved
0.6413	Remote Similarity	NPD4243	Approved
0.641	Remote Similarity	NPD6317	Approved
0.6396	Remote Similarity	NPD4767	Approved
0.6396	Remote Similarity	NPD4768	Approved
0.6392	Remote Similarity	NPD7332	Phase 2
0.6392	Remote Similarity	NPD4748	Discontinued
0.6392	Remote Similarity	NPD7509	Discontinued
0.6383	Remote Similarity	NPD3702	Approved
0.6374	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6903	Approved
0.6364	Remote Similarity	NPD4754	Approved
0.6356	Remote Similarity	NPD6313	Approved
0.6356	Remote Similarity	NPD6314	Approved
0.6355	Remote Similarity	NPD5173	Approved
0.6348	Remote Similarity	NPD6053	Discontinued
0.6337	Remote Similarity	NPD6098	Approved
0.633	Remote Similarity	NPD1700	Approved
0.6327	Remote Similarity	NPD6902	Approved
0.6327	Remote Similarity	NPD6898	Phase 1
0.6325	Remote Similarity	NPD6868	Approved
0.6311	Remote Similarity	NPD6673	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