NPASS Compound

Structure

NPC219285 OpenBabel07101718242D 32 36 0 0 1 0 0 0 0 0999 V2000 2.4049 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 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 5.8690 -4.0000 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 5.0029 -3.5000 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 -3.5000 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 6.7350 -3.5000 0.0000 C 0 0 1 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 0.6728 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6010 -4.0000 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 1.5388 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 7 8 1 0 0 0 0 7 16 2 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 26 1 0 0 0 0 12 25 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 31 1 0 0 0 0 15 28 2 0 0 0 0 15 32 1 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 17 25 1 1 0 0 0 18 26 1 1 0 0 0 18 27 1 0 0 0 0 19 25 1 1 0 0 0 19 26 1 0 0 0 0 20 24 1 0 0 0 0 20 29 1 1 0 0 0 21 27 1 1 0 0 0 21 32 1 0 0 0 0 22 23 1 0 0 0 0 22 27 1 1 0 0 0 23 30 1 6 0 0 0 23 31 1 0 0 0 0 25 4 1 1 0 0 0 26 5 1 1 0 0 0 27 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.3
Volume:	471.444
LogP:	4.064
LogD:	4.025
LogS:	-4.298
# Rotatable Bonds:	2
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.459
Synthetic Accessibility Score:	5.055
Fsp3:	0.889
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:	-4.739
MDCK Permeability:	3.674824256449938e-05
Pgp-inhibitor:	0.98
Pgp-substrate:	0.06
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.246
30% Bioavailability (F30%):	0.045

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.224
Plasma Protein Binding (PPB):	75.75343322753906%
Volume Distribution (VD):	1.657
Pgp-substrate:	23.863252639770508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.373
CYP2C9-inhibitor:	0.108
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.159
CYP3A4-inhibitor:	0.163
CYP3A4-substrate:	0.17

ADMET: Excretion

Clearance (CL):	3.545
Half-life (T1/2):	0.304

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.121
Drug-inuced Liver Injury (DILI):	0.092
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.751
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.375
Carcinogencity:	0.047
Eye Corrosion:	0.075
Eye Irritation:	0.227
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC219285

Natural Product ID:	NPC219285
*Common Name:**	[(1R,5As,5Br,7Ar,9S,11Ar,11Br,13R,13As,13Bs)-1,9-Dihydroxy-5B,8,8,11A,13A-Pentamethyl-1,3,5,5A,6,7,7A,9,10,11,11B,12,13,13B-Tetradecahydrophenanthro[2,1-E][2]Benzofuran-13-Yl] Acetate
IUPAC Name:	[(1R,5aS,5bR,7aR,9S,11aR,11bR,13R,13aS,13bS)-1,9-dihydroxy-5b,8,8,11a,13a-pentamethyl-1,3,5,5a,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydrophenanthro[2,1-e][2]benzofuran-13-yl] acetate
Synonyms:
Standard InCHIKey:	HNSGSRVVIJFFGB-QMXYAEKJSA-N
Standard InCHI:	InChI=1S/C27H42O5/c1-15(28)32-21-13-19-25(4)12-10-20(29)24(2,3)17(25)9-11-26(19,5)18-8-7-16-14-31-23(30)22(16)27(18,21)6/h7,17-23,29-30H,8-14H2,1-6H3/t17-,18-,19+,20-,21+,22+,23+,25-,26-,27+/m0/s1
SMILES:	CC(=O)O[C@@H]1C[C@H]2[C@@]([C@H]3[C@@]1(C)[C@H]1[C@H](O)OCC1=CC3)(C)CC[C@@H]1[C@]2(C)CC[C@@H](C1(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495272
PubChem CID:	10765805
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
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	=	0.505	ug.mL-1	PMID[465028]

☑ 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 NPC219285 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	1365
0.2-0.3	4392
0.3-0.4	10363
0.4-0.5	11217
0.5-0.6	6189
0.6-0.7	5036
0.7-0.8	3493
0.8-0.85	378
0.85-0.9	52
0.9-0.95	6
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477968
1.0	High Similarity	NPC228251
1.0	High Similarity	NPC161527
1.0	High Similarity	NPC477971
1.0	High Similarity	NPC477972
1.0	High Similarity	NPC20113
0.9565	High Similarity	NPC135224
0.9565	High Similarity	NPC477969
0.9462	High Similarity	NPC8954
0.9462	High Similarity	NPC94905
0.9457	High Similarity	NPC189513
0.9355	High Similarity	NPC100892
0.9355	High Similarity	NPC477970
0.9184	High Similarity	NPC222161
0.898	High Similarity	NPC471363
0.898	High Similarity	NPC238397
0.8932	High Similarity	NPC194951
0.8932	High Similarity	NPC12046
0.8889	High Similarity	NPC127933
0.8889	High Similarity	NPC475889
0.8889	High Similarity	NPC7644
0.8889	High Similarity	NPC7613
0.8889	High Similarity	NPC134270
0.8846	High Similarity	NPC157441
0.8817	High Similarity	NPC470819
0.88	High Similarity	NPC473207
0.88	High Similarity	NPC470321
0.88	High Similarity	NPC264867
0.88	High Similarity	NPC201880
0.88	High Similarity	NPC81567
0.8776	High Similarity	NPC146188
0.8776	High Similarity	NPC324841
0.8763	High Similarity	NPC98112
0.8763	High Similarity	NPC97867
0.875	High Similarity	NPC471372
0.875	High Similarity	NPC471362
0.875	High Similarity	NPC472189
0.8723	High Similarity	NPC470817
0.8713	High Similarity	NPC172867
0.8713	High Similarity	NPC252296
0.87	High Similarity	NPC120009
0.866	High Similarity	NPC171598
0.8632	High Similarity	NPC234335
0.8627	High Similarity	NPC88013
0.8627	High Similarity	NPC184512
0.8627	High Similarity	NPC109376
0.8627	High Similarity	NPC125423
0.8617	High Similarity	NPC293044
0.8586	High Similarity	NPC477716
0.8586	High Similarity	NPC477721
0.8571	High Similarity	NPC477718
0.8571	High Similarity	NPC51499
0.8571	High Similarity	NPC472188
0.8571	High Similarity	NPC477719
0.8571	High Similarity	NPC473125
0.8544	High Similarity	NPC470024
0.8544	High Similarity	NPC224660
0.8544	High Similarity	NPC38948
0.8544	High Similarity	NPC189075
0.8544	High Similarity	NPC325054
0.8544	High Similarity	NPC128795
0.8544	High Similarity	NPC275539
0.8544	High Similarity	NPC217921
0.8544	High Similarity	NPC135015
0.8544	High Similarity	NPC48548
0.8544	High Similarity	NPC311223
0.8529	High Similarity	NPC470055
0.8529	High Similarity	NPC470056
0.8529	High Similarity	NPC218158
0.8515	High Similarity	NPC45897
0.8515	High Similarity	NPC281378
0.85	High Similarity	NPC475617
0.85	High Similarity	NPC477717
0.8495	Intermediate Similarity	NPC173917
0.8491	Intermediate Similarity	NPC44298
0.8491	Intermediate Similarity	NPC40133
0.8491	Intermediate Similarity	NPC290608
0.8491	Intermediate Similarity	NPC473128
0.8491	Intermediate Similarity	NPC49413
0.8485	Intermediate Similarity	NPC476800
0.8485	Intermediate Similarity	NPC318917
0.8485	Intermediate Similarity	NPC325229
0.8485	Intermediate Similarity	NPC472186
0.8485	Intermediate Similarity	NPC477928
0.8485	Intermediate Similarity	NPC473154
0.8485	Intermediate Similarity	NPC471366
0.8485	Intermediate Similarity	NPC275086
0.8469	Intermediate Similarity	NPC304899
0.8469	Intermediate Similarity	NPC253115
0.8462	Intermediate Similarity	NPC31522
0.8462	Intermediate Similarity	NPC316974
0.8462	Intermediate Similarity	NPC40728
0.8462	Intermediate Similarity	NPC112457
0.8462	Intermediate Similarity	NPC206618
0.8454	Intermediate Similarity	NPC105490
0.8447	Intermediate Similarity	NPC110496
0.8447	Intermediate Similarity	NPC475074
0.844	Intermediate Similarity	NPC470914
0.8438	Intermediate Similarity	NPC477574
0.8438	Intermediate Similarity	NPC41239
0.8438	Intermediate Similarity	NPC472811
0.8438	Intermediate Similarity	NPC329842
0.8431	Intermediate Similarity	NPC470768
0.8421	Intermediate Similarity	NPC261320
0.8421	Intermediate Similarity	NPC246028
0.8416	Intermediate Similarity	NPC475344
0.8416	Intermediate Similarity	NPC476471
0.84	Intermediate Similarity	NPC473204
0.84	Intermediate Similarity	NPC472187
0.84	Intermediate Similarity	NPC473545
0.8387	Intermediate Similarity	NPC119001
0.8381	Intermediate Similarity	NPC316708
0.8381	Intermediate Similarity	NPC119550
0.8367	Intermediate Similarity	NPC276110
0.8367	Intermediate Similarity	NPC230347
0.8367	Intermediate Similarity	NPC286612
0.8367	Intermediate Similarity	NPC275310
0.8365	Intermediate Similarity	NPC90946
0.8365	Intermediate Similarity	NPC300614
0.8351	Intermediate Similarity	NPC7349
0.8351	Intermediate Similarity	NPC163902
0.8351	Intermediate Similarity	NPC246860
0.8351	Intermediate Similarity	NPC472812
0.8333	Intermediate Similarity	NPC473124
0.8333	Intermediate Similarity	NPC471885
0.8333	Intermediate Similarity	NPC474124
0.8333	Intermediate Similarity	NPC471887
0.8333	Intermediate Similarity	NPC471888
0.8333	Intermediate Similarity	NPC473123
0.8333	Intermediate Similarity	NPC471208
0.8333	Intermediate Similarity	NPC471886
0.8333	Intermediate Similarity	NPC220216
0.8317	Intermediate Similarity	NPC63249
0.8316	Intermediate Similarity	NPC263079
0.8302	Intermediate Similarity	NPC17791
0.8302	Intermediate Similarity	NPC470026
0.83	Intermediate Similarity	NPC247233
0.8298	Intermediate Similarity	NPC118266
0.8283	Intermediate Similarity	NPC165632
0.8283	Intermediate Similarity	NPC54248
0.8283	Intermediate Similarity	NPC276103
0.828	Intermediate Similarity	NPC102048
0.8273	Intermediate Similarity	NPC122971
0.8269	Intermediate Similarity	NPC473586
0.8269	Intermediate Similarity	NPC471205
0.8269	Intermediate Similarity	NPC472390
0.8269	Intermediate Similarity	NPC475781
0.8265	Intermediate Similarity	NPC472360
0.8265	Intermediate Similarity	NPC104925
0.8265	Intermediate Similarity	NPC472416
0.8265	Intermediate Similarity	NPC469697
0.8265	Intermediate Similarity	NPC298973
0.8265	Intermediate Similarity	NPC88507
0.8265	Intermediate Similarity	NPC211238
0.8265	Intermediate Similarity	NPC474922
0.8265	Intermediate Similarity	NPC477722
0.8257	Intermediate Similarity	NPC203862
0.8252	Intermediate Similarity	NPC470064
0.8252	Intermediate Similarity	NPC173583
0.8252	Intermediate Similarity	NPC470061
0.8252	Intermediate Similarity	NPC203354
0.8252	Intermediate Similarity	NPC93352
0.8252	Intermediate Similarity	NPC470059
0.8252	Intermediate Similarity	NPC470058
0.8252	Intermediate Similarity	NPC110656
0.8252	Intermediate Similarity	NPC473127
0.8252	Intermediate Similarity	NPC473543
0.8252	Intermediate Similarity	NPC470043
0.8252	Intermediate Similarity	NPC470062
0.8252	Intermediate Similarity	NPC31430
0.8252	Intermediate Similarity	NPC470060
0.8252	Intermediate Similarity	NPC470057
0.8252	Intermediate Similarity	NPC85593
0.8247	Intermediate Similarity	NPC124374
0.8241	Intermediate Similarity	NPC69576
0.8241	Intermediate Similarity	NPC471633
0.8241	Intermediate Similarity	NPC31354
0.8241	Intermediate Similarity	NPC84949
0.8235	Intermediate Similarity	NPC471482
0.8235	Intermediate Similarity	NPC300399
0.8235	Intermediate Similarity	NPC154452
0.8235	Intermediate Similarity	NPC165250
0.8235	Intermediate Similarity	NPC471889
0.8235	Intermediate Similarity	NPC134077
0.8235	Intermediate Similarity	NPC472815
0.8235	Intermediate Similarity	NPC37207
0.8229	Intermediate Similarity	NPC477917
0.8229	Intermediate Similarity	NPC473647
0.8229	Intermediate Similarity	NPC16265
0.8224	Intermediate Similarity	NPC317460
0.8224	Intermediate Similarity	NPC470025
0.8224	Intermediate Similarity	NPC328074
0.8224	Intermediate Similarity	NPC321272
0.8218	Intermediate Similarity	NPC208358
0.8218	Intermediate Similarity	NPC251680
0.8218	Intermediate Similarity	NPC474190
0.8211	Intermediate Similarity	NPC471779
0.8211	Intermediate Similarity	NPC166857
0.8208	Intermediate Similarity	NPC177047
0.82	Intermediate Similarity	NPC96597

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 NPC219285 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1498
0.2-0.3	3824
0.3-0.4	2440
0.4-0.5	720
0.5-0.6	266
0.6-0.7	205
0.7-0.8	31
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.83	Intermediate Similarity	NPD7638	Approved
0.8218	Intermediate Similarity	NPD7640	Approved
0.8218	Intermediate Similarity	NPD7639	Approved
0.8018	Intermediate Similarity	NPD7328	Approved
0.8018	Intermediate Similarity	NPD7327	Approved
0.7965	Intermediate Similarity	NPD8033	Approved
0.7946	Intermediate Similarity	NPD7516	Approved
0.7876	Intermediate Similarity	NPD8294	Approved
0.7876	Intermediate Similarity	NPD8377	Approved
0.7807	Intermediate Similarity	NPD8335	Approved
0.7807	Intermediate Similarity	NPD8380	Approved
0.7807	Intermediate Similarity	NPD8378	Approved
0.7807	Intermediate Similarity	NPD8379	Approved
0.7807	Intermediate Similarity	NPD8296	Approved
0.7685	Intermediate Similarity	NPD6686	Approved
0.7652	Intermediate Similarity	NPD7503	Approved
0.7547	Intermediate Similarity	NPD7632	Discontinued
0.7542	Intermediate Similarity	NPD7507	Approved
0.7429	Intermediate Similarity	NPD4225	Approved
0.7379	Intermediate Similarity	NPD7748	Approved
0.7368	Intermediate Similarity	NPD7645	Phase 2
0.7355	Intermediate Similarity	NPD7319	Approved
0.7353	Intermediate Similarity	NPD7515	Phase 2
0.7347	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8133	Approved
0.7333	Intermediate Similarity	NPD7902	Approved
0.7297	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7525	Registered
0.7282	Intermediate Similarity	NPD6399	Phase 3
0.7273	Intermediate Similarity	NPD6412	Phase 2
0.7157	Intermediate Similarity	NPD6051	Approved
0.7155	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD7736	Approved
0.7083	Intermediate Similarity	NPD8328	Phase 3
0.7059	Intermediate Similarity	NPD8513	Phase 3
0.7059	Intermediate Similarity	NPD8517	Approved
0.7059	Intermediate Similarity	NPD8516	Approved
0.7059	Intermediate Similarity	NPD8515	Approved
0.7048	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7900	Approved
0.7019	Intermediate Similarity	NPD8034	Phase 2
0.7019	Intermediate Similarity	NPD8035	Phase 2
0.7009	Intermediate Similarity	NPD7115	Discovery
0.6972	Remote Similarity	NPD5344	Discontinued
0.6947	Remote Similarity	NPD6942	Approved
0.6947	Remote Similarity	NPD7339	Approved
0.6931	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD8293	Discontinued
0.6875	Remote Similarity	NPD7128	Approved
0.6875	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5739	Approved
0.6875	Remote Similarity	NPD6008	Approved
0.6875	Remote Similarity	NPD6675	Approved
0.6875	Remote Similarity	NPD6402	Approved
0.686	Remote Similarity	NPD6370	Approved
0.6857	Remote Similarity	NPD7637	Suspended
0.6832	Remote Similarity	NPD4786	Approved
0.6832	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6882	Approved
0.6803	Remote Similarity	NPD6067	Discontinued
0.68	Remote Similarity	NPD3667	Approved
0.6796	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6899	Approved
0.6754	Remote Similarity	NPD7320	Approved
0.6754	Remote Similarity	NPD6881	Approved
0.6748	Remote Similarity	NPD7492	Approved
0.6733	Remote Similarity	NPD6695	Phase 3
0.6731	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6648	Approved
0.6723	Remote Similarity	NPD6009	Approved
0.6699	Remote Similarity	NPD3618	Phase 1
0.6696	Remote Similarity	NPD6373	Approved
0.6696	Remote Similarity	NPD6372	Approved
0.6694	Remote Similarity	NPD6616	Approved
0.6694	Remote Similarity	NPD6059	Approved
0.6694	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.664	Remote Similarity	NPD7078	Approved
0.6638	Remote Similarity	NPD6883	Approved
0.6638	Remote Similarity	NPD7102	Approved
0.6638	Remote Similarity	NPD7290	Approved
0.6636	Remote Similarity	NPD5779	Approved
0.6636	Remote Similarity	NPD5778	Approved
0.6634	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.661	Remote Similarity	NPD4632	Approved
0.6609	Remote Similarity	NPD6011	Approved
0.6609	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD1694	Approved
0.66	Remote Similarity	NPD6928	Phase 2
0.6581	Remote Similarity	NPD6617	Approved
0.6581	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6649	Approved
0.6581	Remote Similarity	NPD6847	Approved
0.6581	Remote Similarity	NPD6650	Approved
0.6581	Remote Similarity	NPD8130	Phase 1
0.6581	Remote Similarity	NPD6869	Approved
0.6552	Remote Similarity	NPD6013	Approved
0.6552	Remote Similarity	NPD6012	Approved
0.6552	Remote Similarity	NPD6014	Approved
0.6545	Remote Similarity	NPD6083	Phase 2
0.6545	Remote Similarity	NPD6084	Phase 2
0.6542	Remote Similarity	NPD6079	Approved
0.6542	Remote Similarity	NPD6411	Approved
0.6538	Remote Similarity	NPD7334	Approved
0.6538	Remote Similarity	NPD6684	Approved
0.6538	Remote Similarity	NPD6409	Approved
0.6538	Remote Similarity	NPD7146	Approved
0.6538	Remote Similarity	NPD7521	Approved
0.6538	Remote Similarity	NPD5330	Approved
0.6525	Remote Similarity	NPD8297	Approved
0.6504	Remote Similarity	NPD6015	Approved
0.6504	Remote Similarity	NPD6016	Approved
0.65	Remote Similarity	NPD6929	Approved
0.6496	Remote Similarity	NPD7625	Phase 1
0.6486	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4202	Approved
0.6476	Remote Similarity	NPD7750	Discontinued
0.6476	Remote Similarity	NPD7524	Approved
0.6452	Remote Similarity	NPD5988	Approved
0.6449	Remote Similarity	NPD7838	Discovery
0.6449	Remote Similarity	NPD46	Approved
0.6449	Remote Similarity	NPD6698	Approved
0.6436	Remote Similarity	NPD6930	Phase 2
0.6436	Remote Similarity	NPD6931	Approved
0.6429	Remote Similarity	NPD8264	Approved
0.6423	Remote Similarity	NPD6319	Approved
0.6415	Remote Similarity	NPD6903	Approved
0.6415	Remote Similarity	NPD5737	Approved
0.6415	Remote Similarity	NPD6672	Approved
0.64	Remote Similarity	NPD7604	Phase 2
0.64	Remote Similarity	NPD6114	Approved
0.64	Remote Similarity	NPD6115	Approved
0.64	Remote Similarity	NPD6118	Approved
0.64	Remote Similarity	NPD6697	Approved
0.6396	Remote Similarity	NPD4755	Approved
0.6378	Remote Similarity	NPD8074	Phase 3
0.6371	Remote Similarity	NPD5983	Phase 2
0.6364	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6101	Approved
0.6346	Remote Similarity	NPD3133	Approved
0.6346	Remote Similarity	NPD3666	Approved
0.6346	Remote Similarity	NPD3668	Phase 3
0.6346	Remote Similarity	NPD3665	Phase 1
0.633	Remote Similarity	NPD8171	Discontinued
0.6328	Remote Similarity	NPD6033	Approved
0.6327	Remote Similarity	NPD6926	Approved
0.6327	Remote Similarity	NPD6924	Approved
0.6321	Remote Similarity	NPD4251	Approved
0.6321	Remote Similarity	NPD4250	Approved
0.6321	Remote Similarity	NPD3573	Approved
0.6316	Remote Similarity	NPD5211	Phase 2
0.6306	Remote Similarity	NPD5222	Approved
0.6306	Remote Similarity	NPD4697	Phase 3
0.6306	Remote Similarity	NPD5221	Approved
0.6306	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6116	Phase 1
0.63	Remote Similarity	NPD6925	Approved
0.63	Remote Similarity	NPD5776	Phase 2
0.6299	Remote Similarity	NPD6336	Discontinued
0.6286	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD4700	Approved
0.6283	Remote Similarity	NPD4696	Approved
0.6283	Remote Similarity	NPD5285	Approved
0.6283	Remote Similarity	NPD5286	Approved
0.6275	Remote Similarity	NPD7514	Phase 3
0.6275	Remote Similarity	NPD7509	Discontinued
0.6275	Remote Similarity	NPD7332	Phase 2
0.626	Remote Similarity	NPD6335	Approved
0.625	Remote Similarity	NPD5173	Approved
0.6239	Remote Similarity	NPD5693	Phase 1
0.6239	Remote Similarity	NPD7087	Discontinued
0.6238	Remote Similarity	NPD7145	Approved
0.623	Remote Similarity	NPD6274	Approved
0.623	Remote Similarity	NPD6868	Approved
0.6228	Remote Similarity	NPD4159	Approved
0.6228	Remote Similarity	NPD5223	Approved
0.6226	Remote Similarity	NPD4249	Approved
0.6216	Remote Similarity	NPD5695	Phase 3
0.6214	Remote Similarity	NPD6902	Approved
0.621	Remote Similarity	NPD7101	Approved
0.621	Remote Similarity	NPD7100	Approved
0.6207	Remote Similarity	NPD5141	Approved
0.62	Remote Similarity	NPD6117	Approved
0.62	Remote Similarity	NPD6933	Approved
0.6195	Remote Similarity	NPD5696	Approved
0.6179	Remote Similarity	NPD6317	Approved
0.6174	Remote Similarity	NPD5224	Approved
0.6174	Remote Similarity	NPD4633	Approved
0.6174	Remote Similarity	NPD5225	Approved
0.6174	Remote Similarity	NPD5226	Approved
0.6162	Remote Similarity	NPD4785	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