NPASS Compound

Structure

NPC288970 OpenBabel07101718242D 33 36 0 0 1 0 0 0 0 0999 V2000 5.9580 -4.9884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5607 -4.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9594 -2.6169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1028 -4.3815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1321 -3.3213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3566 -3.1377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7056 -3.8607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0251 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4532 -1.1588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6090 -4.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3083 -3.3400 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7539 -3.6584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6852 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4532 -2.7331 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5279 -1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6852 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5279 -2.4324 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 1 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 -2.5279 0.4865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 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 6 27 1 0 0 0 0 7 33 1 0 0 0 0 8 9 2 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 27 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 28 1 0 0 0 0 16 24 2 0 0 0 0 16 25 1 0 0 0 0 17 21 1 0 0 0 0 17 29 1 0 0 0 0 18 19 1 0 0 0 0 19 3 1 1 0 0 0 20 4 1 1 0 0 0 20 22 1 0 0 0 0 21 30 1 6 0 0 0 22 26 1 6 0 0 0 23 24 1 0 0 0 0 23 26 1 6 0 0 0 24 28 1 0 0 0 0 25 29 1 6 0 0 0 25 33 1 0 0 0 0 26 5 1 6 0 0 0 27 28 1 1 0 0 0 28 31 1 1 0 0 0 29 27 1 1 0 0 0 29 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.36
Volume:	505.802
LogP:	4.735
LogD:	4.56
LogS:	-5.17
# Rotatable Bonds:	5
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.489
Synthetic Accessibility Score:	5.186
Fsp3:	0.862
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:	-4.794
MDCK Permeability:	5.572424197453074e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.912
Human Intestinal Absorption (HIA):	0.094
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.756

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	89.12447357177734%
Volume Distribution (VD):	1.466
Pgp-substrate:	2.171180486679077%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.656
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.87
CYP2C9-inhibitor:	0.216
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.882
CYP3A4-substrate:	0.92

ADMET: Excretion

Clearance (CL):	2.881
Half-life (T1/2):	0.145

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.262
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.773
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.051
Carcinogencity:	0.007
Eye Corrosion:	0.003
Eye Irritation:	0.043
Respiratory Toxicity:	0.915

Download Data

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

Natural Product: NPC288970

Natural Product ID:	NPC288970
*Common Name:**	Topsentisterol C3
IUPAC Name:	(3S,5R,6R,9R,10R,13R,14R,17R)-17-[(E,2R,5S)-5,6-dimethylhept-3-en-2-yl]-6-methoxy-10,13-dimethyl-2,3,4,6,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,5,9-triol
Synonyms:	Topsentisterol C3
Standard InCHIKey:	ZHBXGHWSDHVEKS-BAICXCQRSA-N
Standard InCHI:	InChI=1S/C29H48O4/c1-18(2)19(3)8-9-20(4)22-10-11-23-24-16-25(33-7)29(32)17-21(30)12-13-27(29,6)28(24,31)15-14-26(22,23)5/h8-9,16,18-23,25,30-32H,10-15,17H2,1-7H3/b9-8+/t19-,20-,21+,22-,23+,25-,26-,27-,28-,29+/m1/s1
SMILES:	CC(C)[C@H](C)/C=C/[C@@H](C)[C@H]1CC[C@H]2C3=C[C@H]([C@]4(C[C@H](CC[C@]4(C)[C@]3(CC[C@]12C)O)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL524156
PubChem CID:	16099493
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
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	At the 20 m depth, the coast of Jeju Island, Korea	2002-OCT	PMID[16643027]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	the coast of Jeju Island, Korea	2002-OCT	PMID[16643027]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[17190456]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[19653640]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[2045823]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[20806907]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[8145229]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	5.6	ug ml-1	PMID[522918]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	7.8	ug ml-1	PMID[522918]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	11.5	ug ml-1	PMID[522918]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	4.7	ug ml-1	PMID[522918]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	4.3	ug ml-1	PMID[522918]

☑ 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 NPC288970 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	1354
0.2-0.3	4404
0.3-0.4	9516
0.4-0.5	12724
0.5-0.6	6774
0.6-0.7	5432
0.7-0.8	2031
0.8-0.85	197
0.85-0.9	44
0.9-0.95	15
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9775	High Similarity	NPC65402
0.9775	High Similarity	NPC127718
0.9667	High Similarity	NPC8774
0.956	High Similarity	NPC227583
0.956	High Similarity	NPC12103
0.956	High Similarity	NPC98457
0.9551	High Similarity	NPC41554
0.9551	High Similarity	NPC97404
0.9438	High Similarity	NPC291484
0.9438	High Similarity	NPC204188
0.9438	High Similarity	NPC11216
0.9438	High Similarity	NPC3345
0.9438	High Similarity	NPC329596
0.9438	High Similarity	NPC80561
0.9326	High Similarity	NPC470361
0.9222	High Similarity	NPC295668
0.9101	High Similarity	NPC149224
0.9043	High Similarity	NPC261807
0.9022	High Similarity	NPC310013
0.9	High Similarity	NPC133588
0.9	High Similarity	NPC474668
0.8989	High Similarity	NPC6391
0.8989	High Similarity	NPC261266
0.8989	High Similarity	NPC299068
0.8936	High Similarity	NPC72204
0.8936	High Similarity	NPC103165
0.8936	High Similarity	NPC210717
0.8925	High Similarity	NPC144202
0.8876	High Similarity	NPC266511
0.8876	High Similarity	NPC470360
0.8876	High Similarity	NPC274448
0.8817	High Similarity	NPC27531
0.8764	High Similarity	NPC470077
0.8764	High Similarity	NPC205845
0.8764	High Similarity	NPC185568
0.8763	High Similarity	NPC475617
0.875	High Similarity	NPC476895
0.8713	High Similarity	NPC173905
0.8713	High Similarity	NPC472216
0.8713	High Similarity	NPC5475
0.8713	High Similarity	NPC284828
0.871	High Similarity	NPC210268
0.871	High Similarity	NPC275671
0.8687	High Similarity	NPC473543
0.8667	High Similarity	NPC157257
0.866	High Similarity	NPC473510
0.8652	High Similarity	NPC474634
0.8646	High Similarity	NPC210337
0.8646	High Similarity	NPC476893
0.8617	High Similarity	NPC137461
0.8602	High Similarity	NPC473956
0.8602	High Similarity	NPC475751
0.8602	High Similarity	NPC192437
0.8602	High Similarity	NPC245410
0.8602	High Similarity	NPC270511
0.8602	High Similarity	NPC470390
0.8602	High Similarity	NPC14380
0.8587	High Similarity	NPC67872
0.8586	High Similarity	NPC474124
0.8586	High Similarity	NPC473523
0.8571	High Similarity	NPC152808
0.8571	High Similarity	NPC476896
0.8571	High Similarity	NPC293287
0.8556	High Similarity	NPC83702
0.8542	High Similarity	NPC88009
0.8539	High Similarity	NPC50964
0.8539	High Similarity	NPC30166
0.8539	High Similarity	NPC101462
0.8539	High Similarity	NPC49964
0.8539	High Similarity	NPC470049
0.8526	High Similarity	NPC477605
0.8515	High Similarity	NPC33053
0.8511	High Similarity	NPC114389
0.8495	Intermediate Similarity	NPC101886
0.8495	Intermediate Similarity	NPC109744
0.8485	Intermediate Similarity	NPC475344
0.8485	Intermediate Similarity	NPC476471
0.8485	Intermediate Similarity	NPC471482
0.8485	Intermediate Similarity	NPC300399
0.8478	Intermediate Similarity	NPC476948
0.8478	Intermediate Similarity	NPC470620
0.8469	Intermediate Similarity	NPC230546
0.8469	Intermediate Similarity	NPC38855
0.8462	Intermediate Similarity	NPC473567
0.8462	Intermediate Similarity	NPC216595
0.8454	Intermediate Similarity	NPC477226
0.8447	Intermediate Similarity	NPC103627
0.8447	Intermediate Similarity	NPC65155
0.8447	Intermediate Similarity	NPC191439
0.8447	Intermediate Similarity	NPC170974
0.8444	Intermediate Similarity	NPC470558
0.8444	Intermediate Similarity	NPC317458
0.8438	Intermediate Similarity	NPC476894
0.8431	Intermediate Similarity	NPC472219
0.8431	Intermediate Similarity	NPC472217
0.8431	Intermediate Similarity	NPC472218
0.8427	Intermediate Similarity	NPC264245
0.8427	Intermediate Similarity	NPC470383
0.8427	Intermediate Similarity	NPC474752
0.8427	Intermediate Similarity	NPC7505
0.8427	Intermediate Similarity	NPC209620
0.8427	Intermediate Similarity	NPC474683
0.8427	Intermediate Similarity	NPC474731
0.8427	Intermediate Similarity	NPC82986
0.8427	Intermediate Similarity	NPC249423
0.8427	Intermediate Similarity	NPC476646
0.8427	Intermediate Similarity	NPC23852
0.8427	Intermediate Similarity	NPC474759
0.8421	Intermediate Similarity	NPC119379
0.8421	Intermediate Similarity	NPC98193
0.8421	Intermediate Similarity	NPC307776
0.84	Intermediate Similarity	NPC471888
0.84	Intermediate Similarity	NPC471886
0.84	Intermediate Similarity	NPC471887
0.84	Intermediate Similarity	NPC471885
0.8387	Intermediate Similarity	NPC471952
0.8387	Intermediate Similarity	NPC475664
0.8387	Intermediate Similarity	NPC212596
0.8387	Intermediate Similarity	NPC4574
0.8387	Intermediate Similarity	NPC280556
0.8387	Intermediate Similarity	NPC475605
0.837	Intermediate Similarity	NPC201273
0.837	Intermediate Similarity	NPC125399
0.837	Intermediate Similarity	NPC94462
0.837	Intermediate Similarity	NPC6605
0.837	Intermediate Similarity	NPC139724
0.837	Intermediate Similarity	NPC255143
0.8365	Intermediate Similarity	NPC65034
0.8365	Intermediate Similarity	NPC208189
0.8352	Intermediate Similarity	NPC15534
0.8352	Intermediate Similarity	NPC124172
0.8351	Intermediate Similarity	NPC471903
0.835	Intermediate Similarity	NPC473328
0.835	Intermediate Similarity	NPC128133
0.835	Intermediate Similarity	NPC28844
0.835	Intermediate Similarity	NPC473318
0.8333	Intermediate Similarity	NPC87489
0.8333	Intermediate Similarity	NPC471408
0.8333	Intermediate Similarity	NPC296701
0.8333	Intermediate Similarity	NPC218616
0.8317	Intermediate Similarity	NPC93352
0.8317	Intermediate Similarity	NPC75608
0.8316	Intermediate Similarity	NPC471453
0.8315	Intermediate Similarity	NPC241290
0.8315	Intermediate Similarity	NPC234193
0.8315	Intermediate Similarity	NPC164840
0.8315	Intermediate Similarity	NPC96362
0.8315	Intermediate Similarity	NPC209944
0.83	Intermediate Similarity	NPC37207
0.83	Intermediate Similarity	NPC471889
0.8298	Intermediate Similarity	NPC259875
0.8298	Intermediate Similarity	NPC187785
0.8298	Intermediate Similarity	NPC105495
0.8298	Intermediate Similarity	NPC115607
0.8298	Intermediate Similarity	NPC138974
0.8286	Intermediate Similarity	NPC477050
0.8286	Intermediate Similarity	NPC231797
0.828	Intermediate Similarity	NPC304083
0.828	Intermediate Similarity	NPC186145
0.828	Intermediate Similarity	NPC474657
0.8265	Intermediate Similarity	NPC476021
0.8265	Intermediate Similarity	NPC474994
0.8265	Intermediate Similarity	NPC476040
0.8261	Intermediate Similarity	NPC318390
0.8242	Intermediate Similarity	NPC211135
0.8242	Intermediate Similarity	NPC207013
0.8242	Intermediate Similarity	NPC475789
0.8242	Intermediate Similarity	NPC85095
0.8242	Intermediate Similarity	NPC320548
0.8242	Intermediate Similarity	NPC216420
0.8235	Intermediate Similarity	NPC472898
0.8235	Intermediate Similarity	NPC472899
0.8235	Intermediate Similarity	NPC472900
0.8222	Intermediate Similarity	NPC47761
0.8222	Intermediate Similarity	NPC474531
0.8218	Intermediate Similarity	NPC471450
0.8202	Intermediate Similarity	NPC30986
0.8202	Intermediate Similarity	NPC209430
0.8202	Intermediate Similarity	NPC328714
0.8202	Intermediate Similarity	NPC28862
0.8202	Intermediate Similarity	NPC84694
0.8202	Intermediate Similarity	NPC47982
0.8202	Intermediate Similarity	NPC143182
0.8202	Intermediate Similarity	NPC109546
0.8202	Intermediate Similarity	NPC81306
0.82	Intermediate Similarity	NPC21568
0.82	Intermediate Similarity	NPC285231
0.82	Intermediate Similarity	NPC470434
0.819	Intermediate Similarity	NPC470076
0.8182	Intermediate Similarity	NPC216260
0.8182	Intermediate Similarity	NPC5358
0.8173	Intermediate Similarity	NPC472901
0.8172	Intermediate Similarity	NPC121981
0.8172	Intermediate Similarity	NPC269058
0.8172	Intermediate Similarity	NPC71520
0.8172	Intermediate Similarity	NPC24277
0.8155	Intermediate Similarity	NPC475781
0.8152	Intermediate Similarity	NPC231310
0.8152	Intermediate Similarity	NPC238485
0.8152	Intermediate Similarity	NPC127606

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 NPC288970 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	1493
0.2-0.3	3923
0.3-0.4	2348
0.4-0.5	738
0.5-0.6	223
0.6-0.7	172
0.7-0.8	71
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.828	Intermediate Similarity	NPD7524	Approved
0.8152	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD7525	Registered
0.8043	Intermediate Similarity	NPD6695	Phase 3
0.7912	Intermediate Similarity	NPD7514	Phase 3
0.7912	Intermediate Similarity	NPD6931	Approved
0.7912	Intermediate Similarity	NPD6930	Phase 2
0.7895	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD6929	Approved
0.7753	Intermediate Similarity	NPD7339	Approved
0.7753	Intermediate Similarity	NPD6942	Approved
0.7717	Intermediate Similarity	NPD7332	Phase 2
0.7708	Intermediate Similarity	NPD7750	Discontinued
0.7692	Intermediate Similarity	NPD7145	Approved
0.7658	Intermediate Similarity	NPD7115	Discovery
0.7634	Intermediate Similarity	NPD6902	Approved
0.7589	Intermediate Similarity	NPD7328	Approved
0.7589	Intermediate Similarity	NPD7327	Approved
0.7582	Intermediate Similarity	NPD6925	Approved
0.7582	Intermediate Similarity	NPD6932	Approved
0.7582	Intermediate Similarity	NPD5776	Phase 2
0.7573	Intermediate Similarity	NPD7640	Approved
0.7573	Intermediate Similarity	NPD7639	Approved
0.7522	Intermediate Similarity	NPD7516	Approved
0.75	Intermediate Similarity	NPD6893	Approved
0.75	Intermediate Similarity	NPD4159	Approved
0.7476	Intermediate Similarity	NPD7638	Approved
0.7473	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD6933	Approved
0.7419	Intermediate Similarity	NPD7645	Phase 2
0.74	Intermediate Similarity	NPD7087	Discontinued
0.7391	Intermediate Similarity	NPD8296	Approved
0.7391	Intermediate Similarity	NPD8380	Approved
0.7391	Intermediate Similarity	NPD8379	Approved
0.7391	Intermediate Similarity	NPD8033	Approved
0.7391	Intermediate Similarity	NPD8335	Approved
0.7391	Intermediate Similarity	NPD8378	Approved
0.7391	Intermediate Similarity	NPD7503	Approved
0.7333	Intermediate Similarity	NPD5344	Discontinued
0.7308	Intermediate Similarity	NPD4225	Approved
0.7304	Intermediate Similarity	NPD8377	Approved
0.7304	Intermediate Similarity	NPD8294	Approved
0.7264	Intermediate Similarity	NPD5211	Phase 2
0.7263	Intermediate Similarity	NPD6898	Phase 1
0.7253	Intermediate Similarity	NPD6924	Approved
0.7253	Intermediate Similarity	NPD4785	Approved
0.7253	Intermediate Similarity	NPD4784	Approved
0.7253	Intermediate Similarity	NPD6926	Approved
0.7234	Intermediate Similarity	NPD6683	Phase 2
0.7228	Intermediate Similarity	NPD7637	Suspended
0.7216	Intermediate Similarity	NPD4786	Approved
0.7182	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5141	Approved
0.7128	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4634	Approved
0.708	Intermediate Similarity	NPD4632	Approved
0.7075	Intermediate Similarity	NPD5286	Approved
0.7075	Intermediate Similarity	NPD4696	Approved
0.7075	Intermediate Similarity	NPD5285	Approved
0.7064	Intermediate Similarity	NPD6640	Phase 3
0.7059	Intermediate Similarity	NPD6079	Approved
0.7048	Intermediate Similarity	NPD4755	Approved
0.7033	Intermediate Similarity	NPD7152	Approved
0.7033	Intermediate Similarity	NPD7151	Approved
0.7033	Intermediate Similarity	NPD7150	Approved
0.7033	Intermediate Similarity	NPD4243	Approved
0.703	Intermediate Similarity	NPD6051	Approved
0.703	Intermediate Similarity	NPD5328	Approved
0.701	Intermediate Similarity	NPD3667	Approved
0.7	Intermediate Similarity	NPD7507	Approved
0.7	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD8297	Approved
0.699	Remote Similarity	NPD6399	Phase 3
0.699	Remote Similarity	NPD4202	Approved
0.6989	Remote Similarity	NPD8264	Approved
0.6979	Remote Similarity	NPD7509	Discontinued
0.6979	Remote Similarity	NPD4748	Discontinued
0.6967	Remote Similarity	NPD7319	Approved
0.6944	Remote Similarity	NPD5226	Approved
0.6944	Remote Similarity	NPD5225	Approved
0.6944	Remote Similarity	NPD4633	Approved
0.6944	Remote Similarity	NPD7632	Discontinued
0.6944	Remote Similarity	NPD5224	Approved
0.6937	Remote Similarity	NPD6899	Approved
0.6937	Remote Similarity	NPD6881	Approved
0.6923	Remote Similarity	NPD7143	Approved
0.6923	Remote Similarity	NPD7144	Approved
0.6916	Remote Similarity	NPD4700	Approved
0.6916	Remote Similarity	NPD6648	Approved
0.6909	Remote Similarity	NPD7128	Approved
0.6909	Remote Similarity	NPD5739	Approved
0.6909	Remote Similarity	NPD6675	Approved
0.6909	Remote Similarity	NPD6402	Approved
0.69	Remote Similarity	NPD3618	Phase 1
0.6881	Remote Similarity	NPD5175	Approved
0.6881	Remote Similarity	NPD5174	Approved
0.6864	Remote Similarity	NPD6319	Approved
0.6864	Remote Similarity	NPD6054	Approved
0.6852	Remote Similarity	NPD5223	Approved
0.6847	Remote Similarity	NPD5697	Approved
0.6847	Remote Similarity	NPD6412	Phase 2
0.6814	Remote Similarity	NPD7102	Approved
0.6814	Remote Similarity	NPD6883	Approved
0.6814	Remote Similarity	NPD7290	Approved
0.6814	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6923	Approved
0.6813	Remote Similarity	NPD6922	Approved
0.6796	Remote Similarity	NPD7136	Phase 2
0.6792	Remote Similarity	NPD5221	Approved
0.6792	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5222	Approved
0.6786	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7320	Approved
0.6786	Remote Similarity	NPD6686	Approved
0.6754	Remote Similarity	NPD6617	Approved
0.6754	Remote Similarity	NPD6869	Approved
0.6754	Remote Similarity	NPD6649	Approved
0.6754	Remote Similarity	NPD6847	Approved
0.6754	Remote Similarity	NPD6650	Approved
0.6754	Remote Similarity	NPD8130	Phase 1
0.6752	Remote Similarity	NPD6009	Approved
0.675	Remote Similarity	NPD6370	Approved
0.6729	Remote Similarity	NPD5173	Approved
0.6726	Remote Similarity	NPD6373	Approved
0.6726	Remote Similarity	NPD6014	Approved
0.6726	Remote Similarity	NPD6372	Approved
0.6726	Remote Similarity	NPD6013	Approved
0.6726	Remote Similarity	NPD6012	Approved
0.6723	Remote Similarity	NPD7741	Discontinued
0.6723	Remote Similarity	NPD6059	Approved
0.6701	Remote Similarity	NPD4195	Approved
0.6699	Remote Similarity	NPD4753	Phase 2
0.6696	Remote Similarity	NPD5701	Approved
0.6696	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6639	Remote Similarity	NPD7492	Approved
0.6638	Remote Similarity	NPD8133	Approved
0.6637	Remote Similarity	NPD4730	Approved
0.6637	Remote Similarity	NPD6011	Approved
0.6637	Remote Similarity	NPD4729	Approved
0.6636	Remote Similarity	NPD4697	Phase 3
0.6632	Remote Similarity	NPD5275	Approved
0.6632	Remote Similarity	NPD4190	Phase 3
0.6612	Remote Similarity	NPD5988	Approved
0.6607	Remote Similarity	NPD4768	Approved
0.6607	Remote Similarity	NPD4767	Approved
0.6585	Remote Similarity	NPD6616	Approved
0.6577	Remote Similarity	NPD4754	Approved
0.6574	Remote Similarity	NPD6084	Phase 2
0.6574	Remote Similarity	NPD6083	Phase 2
0.6557	Remote Similarity	NPD7604	Phase 2
0.6552	Remote Similarity	NPD6053	Discontinued
0.6549	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4629	Approved
0.6542	Remote Similarity	NPD5210	Approved
0.6535	Remote Similarity	NPD3666	Approved
0.6535	Remote Similarity	NPD3133	Approved
0.6535	Remote Similarity	NPD3668	Phase 3
0.6535	Remote Similarity	NPD3665	Phase 1
0.6532	Remote Similarity	NPD7078	Approved
0.6529	Remote Similarity	NPD5983	Phase 2
0.6522	Remote Similarity	NPD5247	Approved
0.6522	Remote Similarity	NPD5249	Phase 3
0.6522	Remote Similarity	NPD5248	Approved
0.6522	Remote Similarity	NPD5251	Approved
0.6522	Remote Similarity	NPD5250	Approved
0.6491	Remote Similarity	NPD5128	Approved
0.648	Remote Similarity	NPD7736	Approved
0.6471	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5215	Approved
0.6466	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5217	Approved
0.6466	Remote Similarity	NPD5216	Approved
0.646	Remote Similarity	NPD6008	Approved
0.6452	Remote Similarity	NPD6336	Discontinued
0.6415	Remote Similarity	NPD7515	Phase 2
0.6415	Remote Similarity	NPD8034	Phase 2
0.6415	Remote Similarity	NPD8035	Phase 2
0.6404	Remote Similarity	NPD368	Approved
0.64	Remote Similarity	NPD8293	Discontinued
0.6393	Remote Similarity	NPD8516	Approved
0.6393	Remote Similarity	NPD8517	Approved
0.6393	Remote Similarity	NPD8515	Approved
0.6393	Remote Similarity	NPD8513	Phase 3
0.6379	Remote Similarity	NPD5169	Approved
0.6379	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5135	Approved
0.6364	Remote Similarity	NPD5290	Discontinued
0.6364	Remote Similarity	NPD7101	Approved
0.6364	Remote Similarity	NPD7100	Approved
0.6355	Remote Similarity	NPD5778	Approved
0.6355	Remote Similarity	NPD5779	Approved
0.6337	Remote Similarity	NPD4221	Approved
0.6337	Remote Similarity	NPD4223	Phase 3
0.6325	Remote Similarity	NPD5127	Approved
0.6321	Remote Similarity	NPD3168	Discontinued
0.6321	Remote Similarity	NPD7838	Discovery
0.6311	Remote Similarity	NPD5329	Approved
0.63	Remote Similarity	NPD4819	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