NPASS Compound

Structure

CID8954 OpenBabel06191715332D 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 -1.0219 2.4292 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 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 -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 -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 17 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 7 30 1 0 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 9 18 2 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 21 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 31 1 0 0 0 0 17 29 2 0 0 0 0 17 32 1 0 0 0 0 18 23 1 0 0 0 0 19 25 1 0 0 0 0 19 26 1 1 0 0 0 20 27 1 1 0 0 0 20 28 1 0 0 0 0 21 26 1 1 0 0 0 21 27 1 0 0 0 0 22 28 1 1 0 0 0 22 32 1 0 0 0 0 23 24 1 0 0 0 0 23 28 1 1 0 0 0 24 30 1 6 0 0 0 24 31 1 0 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.32
Volume:	479.95
LogP:	6.274
LogD:	4.657
LogS:	-5.957
# Rotatable Bonds:	3
TPSA:	44.76
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.379
Synthetic Accessibility Score:	4.974
Fsp3:	0.893
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:	-4.707
MDCK Permeability:	1.6517204130650498e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.928
30% Bioavailability (F30%):	0.65

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.152
Plasma Protein Binding (PPB):	89.07334899902344%
Volume Distribution (VD):	2.271
Pgp-substrate:	10.653166770935059%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.27
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.74
CYP2C9-inhibitor:	0.18
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.335
CYP3A4-substrate:	0.261

ADMET: Excretion

Clearance (CL):	4.677
Half-life (T1/2):	0.044

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.31
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.427
Maximum Recommended Daily Dose:	0.859
Skin Sensitization:	0.355
Carcinogencity:	0.237
Eye Corrosion:	0.874
Eye Irritation:	0.338
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC8954

Natural Product ID:	NPC8954
*Common Name:**	[(1R,5As,5Br,7As,11As,11Br,13R,13As,13Bs)-1-Methoxy-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,7aS,11aS,11bR,13R,13aS,13bS)-1-methoxy-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:	MGLNUFHGBIDJLB-NWLMTDSXSA-N
Standard InCHI:	InChI=1S/C28H44O4/c1-17(29)32-22-15-21-26(4)13-8-12-25(2,3)19(26)11-14-27(21,5)20-10-9-18-16-31-24(30-7)23(18)28(20,22)6/h9,19-24H,8,10-16H2,1-7H3/t19-,20-,21+,22+,23+,24+,26-,27-,28+/m0/s1
SMILES:	CC(=O)O[C@@H]1C[C@@H]2[C@@]3(C)CCCC(C)(C)[C@@H]3CC[C@@]2(C)[C@@H]2CC=C3CO[C@H]([C@@H]3[C@@]12C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1773761
PubChem CID:	52951404
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
NPO33664	Hyatella sp.	Species	n.a.	n.a.	n.a.	the coast of Soheuksan-do, Korea	n.a.	PMID[21341710]
NPO31085	Hyattella	Genus	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21341710]

☑ 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
MIC	6
Others	1

Activity Type	# Activity
Cell Line	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	>	100000.0	nM	PMID[512651]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[512651]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[512651]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[512651]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[512651]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[512651]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[512651]

☑ 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 NPC8954 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	233
0.1-0.2	1574
0.2-0.3	4986
0.3-0.4	12236
0.4-0.5	9851
0.5-0.6	6377
0.6-0.7	5021
0.7-0.8	2222
0.8-0.85	154
0.85-0.9	30
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC94905
0.9462	High Similarity	NPC477968
0.9462	High Similarity	NPC228251
0.9462	High Similarity	NPC219285
0.9462	High Similarity	NPC477972
0.9462	High Similarity	NPC477971
0.9462	High Similarity	NPC161527
0.9462	High Similarity	NPC20113
0.9239	High Similarity	NPC471362
0.9239	High Similarity	NPC472189
0.9239	High Similarity	NPC471372
0.914	High Similarity	NPC171598
0.9111	High Similarity	NPC293044
0.9043	High Similarity	NPC472188
0.9032	High Similarity	NPC477970
0.9032	High Similarity	NPC477969
0.9032	High Similarity	NPC135224
0.9032	High Similarity	NPC100892
0.8947	High Similarity	NPC476800
0.8947	High Similarity	NPC471366
0.8947	High Similarity	NPC472186
0.8947	High Similarity	NPC318917
0.8925	High Similarity	NPC189513
0.89	High Similarity	NPC112457
0.8854	High Similarity	NPC472187
0.8854	High Similarity	NPC473204
0.8854	High Similarity	NPC473545
0.8817	High Similarity	NPC163902
0.8778	High Similarity	NPC118266
0.8723	High Similarity	NPC477722
0.8723	High Similarity	NPC88507
0.8687	High Similarity	NPC222161
0.8673	High Similarity	NPC471363
0.8673	High Similarity	NPC238397
0.8586	High Similarity	NPC7613
0.8586	High Similarity	NPC475889
0.8586	High Similarity	NPC120009
0.8586	High Similarity	NPC134270
0.8586	High Similarity	NPC127933
0.8586	High Similarity	NPC7644
0.8558	High Similarity	NPC157441
0.8542	High Similarity	NPC311166
0.85	High Similarity	NPC470321
0.85	High Similarity	NPC473207
0.85	High Similarity	NPC264867
0.85	High Similarity	NPC201880
0.85	High Similarity	NPC81567
0.8495	Intermediate Similarity	NPC470819
0.8469	Intermediate Similarity	NPC146188
0.8462	Intermediate Similarity	NPC194951
0.8462	Intermediate Similarity	NPC12046
0.8454	Intermediate Similarity	NPC97867
0.8454	Intermediate Similarity	NPC98112
0.8416	Intermediate Similarity	NPC252296
0.8416	Intermediate Similarity	NPC172867
0.8404	Intermediate Similarity	NPC470817
0.84	Intermediate Similarity	NPC254202
0.8387	Intermediate Similarity	NPC144069
0.837	Intermediate Similarity	NPC471369
0.8352	Intermediate Similarity	NPC471367
0.8351	Intermediate Similarity	NPC73858
0.8333	Intermediate Similarity	NPC88013
0.8333	Intermediate Similarity	NPC125423
0.8333	Intermediate Similarity	NPC184512
0.8333	Intermediate Similarity	NPC109376
0.8315	Intermediate Similarity	NPC469802
0.8286	Intermediate Similarity	NPC473125
0.8283	Intermediate Similarity	NPC324841
0.8283	Intermediate Similarity	NPC477716
0.8283	Intermediate Similarity	NPC477721
0.8265	Intermediate Similarity	NPC204054
0.8265	Intermediate Similarity	NPC257726
0.8261	Intermediate Similarity	NPC474013
0.8252	Intermediate Similarity	NPC128795
0.8252	Intermediate Similarity	NPC48548
0.8252	Intermediate Similarity	NPC224660
0.8252	Intermediate Similarity	NPC217921
0.8252	Intermediate Similarity	NPC311223
0.8252	Intermediate Similarity	NPC135015
0.8252	Intermediate Similarity	NPC470024
0.8235	Intermediate Similarity	NPC470056
0.8235	Intermediate Similarity	NPC218158
0.8235	Intermediate Similarity	NPC470055
0.8229	Intermediate Similarity	NPC473678
0.8218	Intermediate Similarity	NPC281378
0.8218	Intermediate Similarity	NPC45897
0.8208	Intermediate Similarity	NPC40133
0.8208	Intermediate Similarity	NPC49413
0.8208	Intermediate Similarity	NPC44298
0.8208	Intermediate Similarity	NPC473128
0.8208	Intermediate Similarity	NPC290608
0.82	Intermediate Similarity	NPC477717
0.8191	Intermediate Similarity	NPC106332
0.8182	Intermediate Similarity	NPC473154
0.8182	Intermediate Similarity	NPC477928
0.8173	Intermediate Similarity	NPC40728
0.8173	Intermediate Similarity	NPC206618
0.8173	Intermediate Similarity	NPC316974
0.8172	Intermediate Similarity	NPC471368
0.8172	Intermediate Similarity	NPC102996
0.8172	Intermediate Similarity	NPC323209
0.8172	Intermediate Similarity	NPC173917
0.8172	Intermediate Similarity	NPC286153
0.8165	Intermediate Similarity	NPC470914
0.8137	Intermediate Similarity	NPC476763
0.8137	Intermediate Similarity	NPC476764
0.8137	Intermediate Similarity	NPC470768
0.8125	Intermediate Similarity	NPC329842
0.8125	Intermediate Similarity	NPC234335
0.8105	Intermediate Similarity	NPC246028
0.8095	Intermediate Similarity	NPC119550
0.8095	Intermediate Similarity	NPC316708
0.8085	Intermediate Similarity	NPC102640
0.8081	Intermediate Similarity	NPC477718
0.8081	Intermediate Similarity	NPC477719
0.8081	Intermediate Similarity	NPC51499
0.8077	Intermediate Similarity	NPC189075
0.8077	Intermediate Similarity	NPC275539
0.8077	Intermediate Similarity	NPC38948
0.8077	Intermediate Similarity	NPC325054
0.8065	Intermediate Similarity	NPC472442
0.8061	Intermediate Similarity	NPC286612
0.8061	Intermediate Similarity	NPC230347
0.8061	Intermediate Similarity	NPC275310
0.8058	Intermediate Similarity	NPC476762
0.8058	Intermediate Similarity	NPC476760
0.8058	Intermediate Similarity	NPC51719
0.8058	Intermediate Similarity	NPC476761
0.8043	Intermediate Similarity	NPC132386
0.8043	Intermediate Similarity	NPC472440
0.8041	Intermediate Similarity	NPC246860
0.8041	Intermediate Similarity	NPC7349
0.8039	Intermediate Similarity	NPC471885
0.8039	Intermediate Similarity	NPC473123
0.8039	Intermediate Similarity	NPC473124
0.8039	Intermediate Similarity	NPC471888
0.8039	Intermediate Similarity	NPC471365
0.8039	Intermediate Similarity	NPC471364
0.8039	Intermediate Similarity	NPC471886
0.8039	Intermediate Similarity	NPC471887
0.8039	Intermediate Similarity	NPC132395
0.8022	Intermediate Similarity	NPC25554
0.802	Intermediate Similarity	NPC475617
0.8019	Intermediate Similarity	NPC470026
0.8019	Intermediate Similarity	NPC17791
0.8	Intermediate Similarity	NPC325229
0.8	Intermediate Similarity	NPC122971
0.8	Intermediate Similarity	NPC275086
0.8	Intermediate Similarity	NPC69713
0.8	Intermediate Similarity	NPC263079
0.8	Intermediate Similarity	NPC31522
0.7982	Intermediate Similarity	NPC203862
0.7981	Intermediate Similarity	NPC110496
0.7981	Intermediate Similarity	NPC475074
0.7981	Intermediate Similarity	NPC472390
0.798	Intermediate Similarity	NPC304899
0.798	Intermediate Similarity	NPC194132
0.798	Intermediate Similarity	NPC475178
0.798	Intermediate Similarity	NPC253115
0.7963	Intermediate Similarity	NPC31354
0.7963	Intermediate Similarity	NPC84949
0.7963	Intermediate Similarity	NPC471633
0.7963	Intermediate Similarity	NPC69576
0.7961	Intermediate Similarity	NPC93352
0.7961	Intermediate Similarity	NPC470064
0.7961	Intermediate Similarity	NPC85593
0.7961	Intermediate Similarity	NPC473127
0.7961	Intermediate Similarity	NPC470057
0.7961	Intermediate Similarity	NPC470062
0.7961	Intermediate Similarity	NPC203354
0.7961	Intermediate Similarity	NPC470059
0.7961	Intermediate Similarity	NPC470060
0.7961	Intermediate Similarity	NPC470061
0.7961	Intermediate Similarity	NPC173583
0.7961	Intermediate Similarity	NPC470058
0.7961	Intermediate Similarity	NPC31430
0.7961	Intermediate Similarity	NPC110656
0.7961	Intermediate Similarity	NPC470043
0.7959	Intermediate Similarity	NPC128488
0.7959	Intermediate Similarity	NPC105490
0.7959	Intermediate Similarity	NPC211238
0.7959	Intermediate Similarity	NPC140277
0.7959	Intermediate Similarity	NPC304968
0.7957	Intermediate Similarity	NPC96055
0.7944	Intermediate Similarity	NPC150228
0.7944	Intermediate Similarity	NPC214005
0.7944	Intermediate Similarity	NPC470025
0.7944	Intermediate Similarity	NPC328074
0.7944	Intermediate Similarity	NPC317460
0.7944	Intermediate Similarity	NPC321272
0.7941	Intermediate Similarity	NPC300399
0.7941	Intermediate Similarity	NPC475344
0.7941	Intermediate Similarity	NPC476471
0.7941	Intermediate Similarity	NPC37207
0.7941	Intermediate Similarity	NPC154452
0.7941	Intermediate Similarity	NPC471482
0.7941	Intermediate Similarity	NPC134077
0.7938	Intermediate Similarity	NPC474631
0.7938	Intermediate Similarity	NPC472811
0.7938	Intermediate Similarity	NPC41239

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 NPC8954 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	1687
0.2-0.3	4020
0.3-0.4	2207
0.4-0.5	601
0.5-0.6	282
0.6-0.7	137
0.7-0.8	24
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7822	Intermediate Similarity	NPD7638	Approved
0.7748	Intermediate Similarity	NPD7327	Approved
0.7748	Intermediate Similarity	NPD7328	Approved
0.7745	Intermediate Similarity	NPD7639	Approved
0.7745	Intermediate Similarity	NPD7640	Approved
0.7699	Intermediate Similarity	NPD8033	Approved
0.7679	Intermediate Similarity	NPD7516	Approved
0.7611	Intermediate Similarity	NPD8377	Approved
0.7611	Intermediate Similarity	NPD8294	Approved
0.7544	Intermediate Similarity	NPD8296	Approved
0.7544	Intermediate Similarity	NPD8380	Approved
0.7544	Intermediate Similarity	NPD8379	Approved
0.7544	Intermediate Similarity	NPD8378	Approved
0.7544	Intermediate Similarity	NPD8335	Approved
0.7407	Intermediate Similarity	NPD6686	Approved
0.7391	Intermediate Similarity	NPD7503	Approved
0.7374	Intermediate Similarity	NPD6051	Approved
0.7288	Intermediate Similarity	NPD7507	Approved
0.7255	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7900	Approved
0.7107	Intermediate Similarity	NPD7319	Approved
0.7103	Intermediate Similarity	NPD7632	Discontinued
0.7087	Intermediate Similarity	NPD7748	Approved
0.708	Intermediate Similarity	NPD8133	Approved
0.7064	Intermediate Similarity	NPD6008	Approved
0.7048	Intermediate Similarity	NPD7902	Approved
0.7027	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6412	Phase 2
0.699	Remote Similarity	NPD6399	Phase 3
0.6981	Remote Similarity	NPD4225	Approved
0.6931	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7515	Phase 2
0.6885	Remote Similarity	NPD7736	Approved
0.6875	Remote Similarity	NPD7645	Phase 2
0.6869	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8328	Phase 3
0.6807	Remote Similarity	NPD8516	Approved
0.6807	Remote Similarity	NPD8513	Phase 3
0.6807	Remote Similarity	NPD8515	Approved
0.6807	Remote Similarity	NPD8517	Approved
0.6804	Remote Similarity	NPD7525	Registered
0.68	Remote Similarity	NPD1694	Approved
0.6733	Remote Similarity	NPD5330	Approved
0.6733	Remote Similarity	NPD7521	Approved
0.6733	Remote Similarity	NPD6684	Approved
0.6733	Remote Similarity	NPD7334	Approved
0.6733	Remote Similarity	NPD6409	Approved
0.6733	Remote Similarity	NPD7146	Approved
0.6731	Remote Similarity	NPD8035	Phase 2
0.6731	Remote Similarity	NPD8034	Phase 2
0.6726	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8293	Discontinued
0.6612	Remote Similarity	NPD6370	Approved
0.661	Remote Similarity	NPD7115	Discovery
0.6606	Remote Similarity	NPD6648	Approved
0.6602	Remote Similarity	NPD6672	Approved
0.6602	Remote Similarity	NPD6903	Approved
0.6602	Remote Similarity	NPD5737	Approved
0.6557	Remote Similarity	NPD6067	Discontinued
0.6552	Remote Similarity	NPD6882	Approved
0.6545	Remote Similarity	NPD5344	Discontinued
0.6542	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD3573	Approved
0.6504	Remote Similarity	NPD7492	Approved
0.6471	Remote Similarity	NPD6009	Approved
0.6471	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.646	Remote Similarity	NPD7128	Approved
0.646	Remote Similarity	NPD6675	Approved
0.646	Remote Similarity	NPD6402	Approved
0.646	Remote Similarity	NPD5739	Approved
0.6458	Remote Similarity	NPD7339	Approved
0.6458	Remote Similarity	NPD6942	Approved
0.6452	Remote Similarity	NPD6616	Approved
0.6446	Remote Similarity	NPD6059	Approved
0.6446	Remote Similarity	NPD6054	Approved
0.6415	Remote Similarity	NPD5693	Phase 1
0.6415	Remote Similarity	NPD7637	Suspended
0.64	Remote Similarity	NPD7078	Approved
0.6392	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4786	Approved
0.6373	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD3668	Phase 3
0.6348	Remote Similarity	NPD6881	Approved
0.6348	Remote Similarity	NPD6899	Approved
0.6348	Remote Similarity	NPD7320	Approved
0.6346	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD3667	Approved
0.6325	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6928	Phase 2
0.6293	Remote Similarity	NPD6372	Approved
0.6293	Remote Similarity	NPD6373	Approved
0.6277	Remote Similarity	NPD7625	Phase 1
0.6275	Remote Similarity	NPD6695	Phase 3
0.6271	Remote Similarity	NPD6053	Discontinued
0.6261	Remote Similarity	NPD5697	Approved
0.6261	Remote Similarity	NPD5701	Approved
0.626	Remote Similarity	NPD6016	Approved
0.626	Remote Similarity	NPD6015	Approved
0.625	Remote Similarity	NPD6098	Approved
0.625	Remote Similarity	NPD3618	Phase 1
0.6239	Remote Similarity	NPD6883	Approved
0.6239	Remote Similarity	NPD7102	Approved
0.6239	Remote Similarity	NPD7290	Approved
0.6226	Remote Similarity	NPD6904	Approved
0.6226	Remote Similarity	NPD5328	Approved
0.6226	Remote Similarity	NPD6673	Approved
0.6226	Remote Similarity	NPD6080	Approved
0.6218	Remote Similarity	NPD4632	Approved
0.6216	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.621	Remote Similarity	NPD5988	Approved
0.6207	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6011	Approved
0.6204	Remote Similarity	NPD5779	Approved
0.6204	Remote Similarity	NPD5778	Approved
0.6186	Remote Similarity	NPD6617	Approved
0.6186	Remote Similarity	NPD6649	Approved
0.6186	Remote Similarity	NPD6847	Approved
0.6186	Remote Similarity	NPD6869	Approved
0.6186	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD8130	Phase 1
0.6186	Remote Similarity	NPD6650	Approved
0.6154	Remote Similarity	NPD6012	Approved
0.6154	Remote Similarity	NPD6013	Approved
0.6154	Remote Similarity	NPD6014	Approved
0.6147	Remote Similarity	NPD6001	Approved
0.6142	Remote Similarity	NPD8074	Phase 3
0.6134	Remote Similarity	NPD8297	Approved
0.6126	Remote Similarity	NPD6083	Phase 2
0.6126	Remote Similarity	NPD6084	Phase 2
0.6122	Remote Similarity	NPD8039	Approved
0.6111	Remote Similarity	NPD6079	Approved
0.6111	Remote Similarity	NPD6411	Approved
0.6094	Remote Similarity	NPD6033	Approved
0.6087	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD8171	Discontinued
0.6055	Remote Similarity	NPD4202	Approved
0.6048	Remote Similarity	NPD6319	Approved
0.604	Remote Similarity	NPD6929	Approved
0.6038	Remote Similarity	NPD7524	Approved
0.6038	Remote Similarity	NPD7750	Discontinued
0.6032	Remote Similarity	NPD7604	Phase 2
0.6019	Remote Similarity	NPD6698	Approved
0.6019	Remote Similarity	NPD7838	Discovery
0.6019	Remote Similarity	NPD3168	Discontinued
0.6019	Remote Similarity	NPD46	Approved
0.6	Remote Similarity	NPD5983	Phase 2
0.5982	Remote Similarity	NPD4755	Approved
0.5981	Remote Similarity	NPD5208	Approved
0.598	Remote Similarity	NPD6930	Phase 2
0.598	Remote Similarity	NPD6931	Approved
0.5963	Remote Similarity	NPD6050	Approved
0.596	Remote Similarity	NPD8264	Approved
0.5946	Remote Similarity	NPD5695	Phase 3
0.5941	Remote Similarity	NPD6114	Approved
0.5941	Remote Similarity	NPD6115	Approved
0.5941	Remote Similarity	NPD6118	Approved
0.5941	Remote Similarity	NPD6697	Approved
0.5938	Remote Similarity	NPD6336	Discontinued
0.5929	Remote Similarity	NPD5696	Approved
0.5926	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD1695	Approved
0.5926	Remote Similarity	NPD6101	Approved
0.5913	Remote Similarity	NPD5211	Phase 2
0.5909	Remote Similarity	NPD8449	Approved
0.5905	Remote Similarity	NPD3133	Approved
0.5905	Remote Similarity	NPD3666	Approved
0.5905	Remote Similarity	NPD3665	Phase 1
0.5893	Remote Similarity	NPD7732	Phase 3
0.5893	Remote Similarity	NPD4697	Phase 3
0.5893	Remote Similarity	NPD5222	Approved
0.5893	Remote Similarity	NPD5221	Approved
0.5893	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4250	Approved
0.5888	Remote Similarity	NPD4251	Approved
0.5887	Remote Similarity	NPD6335	Approved
0.5877	Remote Similarity	NPD4700	Approved
0.5877	Remote Similarity	NPD5286	Approved
0.5877	Remote Similarity	NPD4696	Approved
0.5877	Remote Similarity	NPD5285	Approved
0.5876	Remote Similarity	NPD2687	Approved
0.5876	Remote Similarity	NPD2254	Approved
0.5876	Remote Similarity	NPD2686	Approved
0.5872	Remote Similarity	NPD5207	Approved
0.5872	Remote Similarity	NPD5692	Phase 3
0.5865	Remote Similarity	NPD8450	Suspended
0.5859	Remote Similarity	NPD4784	Approved
0.5859	Remote Similarity	NPD4785	Approved
0.5859	Remote Similarity	NPD6926	Approved
0.5859	Remote Similarity	NPD6924	Approved
0.5854	Remote Similarity	NPD6274	Approved
0.5854	Remote Similarity	NPD6868	Approved
0.5851	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5776	Phase 2
0.5842	Remote Similarity	NPD6116	Phase 1

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