NPASS Compound

Structure

NPC261807 OpenBabel07101719142D 31 35 0 0 1 0 0 0 0 0999 V2000 -7.4106 -7.2859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7633 -7.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7926 -5.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 -5.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -4.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 -5.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 -4.9680 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 -3.5491 -2.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 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 -4.0000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4325 -7.0780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1235 -6.1270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8581 -4.7601 0.0000 C 0 0 2 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 -3.8090 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 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 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 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 2.5981 -0.5000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 6 27 1 0 0 0 0 7 8 2 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 17 3 1 6 0 0 0 18 4 1 6 0 0 0 18 20 1 0 0 0 0 19 29 1 1 0 0 0 20 26 1 1 0 0 0 21 23 1 0 0 0 0 21 26 1 1 0 0 0 22 23 2 0 0 0 0 22 27 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 24 30 1 6 0 0 0 25 28 1 1 0 0 0 25 31 1 0 0 0 0 26 5 1 1 0 0 0 27 28 1 1 0 0 0 28 15 1 1 0 0 0 28 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.33
Volume:	471.16
LogP:	5.105
LogD:	4.721
LogS:	-5.247
# Rotatable Bonds:	4
TPSA:	52.99
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.449
Synthetic Accessibility Score:	5.682
Fsp3:	0.857
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:	-4.805
MDCK Permeability:	3.414897219045088e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.978
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.365
30% Bioavailability (F30%):	0.336

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.099
Plasma Protein Binding (PPB):	88.9891128540039%
Volume Distribution (VD):	1.205
Pgp-substrate:	1.5598362684249878%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.666
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.93
CYP2C9-inhibitor:	0.248
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.207
CYP3A4-inhibitor:	0.869
CYP3A4-substrate:	0.858

ADMET: Excretion

Clearance (CL):	4.308
Half-life (T1/2):	0.109

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.164
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.766
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.043
Carcinogencity:	0.014
Eye Corrosion:	0.004
Eye Irritation:	0.031
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC261807

Natural Product ID:	NPC261807
*Common Name:**	Topsentisterol B4
IUPAC Name:	n.a.
Synonyms:	Topsentisterol B4
Standard InCHIKey:	PCIZFQVDNDHRPP-SGWVODBBSA-N
Standard InCHI:	InChI=1S/C28H44O3/c1-16(2)17(3)7-8-18(4)20-9-10-21-23-22(12-13-26(20,21)5)27(6)14-11-19(29)15-28(27)25(31-28)24(23)30/h7-8,16-21,24-25,29-30H,9-15H2,1-6H3/b8-7+/t17-,18-,19+,20-,21+,24+,25+,26-,27-,28+/m1/s1
SMILES:	CC(C)[C@H](C)/C=C/[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](C[C@@]21[C@H]([C@H]3O)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521817
PubChem CID:	16099489
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids

*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.	the coast of Jeju Island, Korea	2002-OCT	PMID[16643027]
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.	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	=	9.7	ug ml-1	PMID[482657]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	7.8	ug ml-1	PMID[482657]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	11.3	ug ml-1	PMID[482657]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	19.0	ug ml-1	PMID[482657]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	14.1	ug ml-1	PMID[482657]

☑ 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 NPC261807 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	200
0.1-0.2	1439
0.2-0.3	4987
0.3-0.4	12208
0.4-0.5	11164
0.5-0.6	7297
0.6-0.7	4544
0.7-0.8	808
0.8-0.85	36
0.85-0.9	10
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9556	High Similarity	NPC137461
0.9457	High Similarity	NPC103165
0.9457	High Similarity	NPC210717
0.914	High Similarity	NPC8774
0.913	High Similarity	NPC310013
0.9121	High Similarity	NPC3345
0.9121	High Similarity	NPC11216
0.9121	High Similarity	NPC329596
0.9121	High Similarity	NPC291484
0.9121	High Similarity	NPC80561
0.9121	High Similarity	NPC204188
0.9043	High Similarity	NPC12103
0.9043	High Similarity	NPC227583
0.9043	High Similarity	NPC98457
0.9043	High Similarity	NPC288970
0.9032	High Similarity	NPC65402
0.9032	High Similarity	NPC127718
0.9022	High Similarity	NPC97404
0.9022	High Similarity	NPC41554
0.9022	High Similarity	NPC114389
0.9011	High Similarity	NPC470361
0.8842	High Similarity	NPC72204
0.8723	High Similarity	NPC119379
0.871	High Similarity	NPC470390
0.871	High Similarity	NPC245410
0.871	High Similarity	NPC192437
0.871	High Similarity	NPC270511
0.8696	High Similarity	NPC133588
0.8681	High Similarity	NPC299068
0.8681	High Similarity	NPC125399
0.8673	High Similarity	NPC476896
0.8632	High Similarity	NPC144202
0.8617	High Similarity	NPC210268
0.8571	High Similarity	NPC470360
0.8557	High Similarity	NPC476040
0.8557	High Similarity	NPC476021
0.8557	High Similarity	NPC474994
0.8526	High Similarity	NPC27531
0.8511	High Similarity	NPC295668
0.8511	High Similarity	NPC14380
0.8495	Intermediate Similarity	NPC474668
0.8478	Intermediate Similarity	NPC261266
0.8478	Intermediate Similarity	NPC6391
0.8478	Intermediate Similarity	NPC255143
0.8469	Intermediate Similarity	NPC476895
0.8462	Intermediate Similarity	NPC474047
0.8444	Intermediate Similarity	NPC87489
0.8421	Intermediate Similarity	NPC275671
0.8404	Intermediate Similarity	NPC115607
0.8367	Intermediate Similarity	NPC476893
0.8352	Intermediate Similarity	NPC475789
0.835	Intermediate Similarity	NPC472218
0.835	Intermediate Similarity	NPC472217
0.835	Intermediate Similarity	NPC472219
0.8316	Intermediate Similarity	NPC191323
0.83	Intermediate Similarity	NPC475617
0.8298	Intermediate Similarity	NPC67872
0.8298	Intermediate Similarity	NPC280556
0.828	Intermediate Similarity	NPC94462
0.8261	Intermediate Similarity	NPC185568
0.8261	Intermediate Similarity	NPC15534
0.8261	Intermediate Similarity	NPC86238
0.8261	Intermediate Similarity	NPC231310
0.8261	Intermediate Similarity	NPC238485
0.8261	Intermediate Similarity	NPC205845
0.8247	Intermediate Similarity	NPC474922
0.8242	Intermediate Similarity	NPC49964
0.8242	Intermediate Similarity	NPC50964
0.8235	Intermediate Similarity	NPC473543
0.8235	Intermediate Similarity	NPC75608
0.8229	Intermediate Similarity	NPC471453
0.8211	Intermediate Similarity	NPC49783
0.8211	Intermediate Similarity	NPC101886
0.8211	Intermediate Similarity	NPC97103
0.8211	Intermediate Similarity	NPC138974
0.8208	Intermediate Similarity	NPC477050
0.82	Intermediate Similarity	NPC324598
0.8191	Intermediate Similarity	NPC149224
0.8172	Intermediate Similarity	NPC274448
0.8172	Intermediate Similarity	NPC474349
0.8172	Intermediate Similarity	NPC474189
0.8163	Intermediate Similarity	NPC476894
0.8155	Intermediate Similarity	NPC472898
0.8155	Intermediate Similarity	NPC472900
0.8155	Intermediate Similarity	NPC472899
0.8152	Intermediate Similarity	NPC474634
0.8152	Intermediate Similarity	NPC317458
0.8152	Intermediate Similarity	NPC132635
0.8152	Intermediate Similarity	NPC477978
0.8152	Intermediate Similarity	NPC470384
0.8144	Intermediate Similarity	NPC98193
0.8144	Intermediate Similarity	NPC307776
0.8137	Intermediate Similarity	NPC474124
0.8137	Intermediate Similarity	NPC473523
0.8132	Intermediate Similarity	NPC23852
0.8132	Intermediate Similarity	NPC470383
0.8132	Intermediate Similarity	NPC476646
0.8132	Intermediate Similarity	NPC209620
0.8132	Intermediate Similarity	NPC264245
0.8132	Intermediate Similarity	NPC249423
0.8125	Intermediate Similarity	NPC475751
0.8125	Intermediate Similarity	NPC473956
0.8119	Intermediate Similarity	NPC470434
0.8119	Intermediate Similarity	NPC476897
0.8105	Intermediate Similarity	NPC473436
0.8105	Intermediate Similarity	NPC212596
0.8105	Intermediate Similarity	NPC4574
0.81	Intermediate Similarity	NPC5358
0.81	Intermediate Similarity	NPC216260
0.8095	Intermediate Similarity	NPC472901
0.8095	Intermediate Similarity	NPC472216
0.8095	Intermediate Similarity	NPC284828
0.8095	Intermediate Similarity	NPC173905
0.8095	Intermediate Similarity	NPC5475
0.8085	Intermediate Similarity	NPC269058
0.8085	Intermediate Similarity	NPC281316
0.8085	Intermediate Similarity	NPC293287
0.8085	Intermediate Similarity	NPC152808
0.8085	Intermediate Similarity	NPC71520
0.8081	Intermediate Similarity	NPC276103
0.8081	Intermediate Similarity	NPC54248
0.8081	Intermediate Similarity	NPC471903
0.8077	Intermediate Similarity	NPC33053
0.8065	Intermediate Similarity	NPC470077
0.8065	Intermediate Similarity	NPC83702
0.8061	Intermediate Similarity	NPC473258
0.8061	Intermediate Similarity	NPC477605
0.8043	Intermediate Similarity	NPC218616
0.8043	Intermediate Similarity	NPC296701
0.8043	Intermediate Similarity	NPC202389
0.8043	Intermediate Similarity	NPC30166
0.8043	Intermediate Similarity	NPC471408
0.8043	Intermediate Similarity	NPC101462
0.8043	Intermediate Similarity	NPC7988
0.8039	Intermediate Similarity	NPC471889
0.8039	Intermediate Similarity	NPC300399
0.8039	Intermediate Similarity	NPC475344
0.8039	Intermediate Similarity	NPC476471
0.8039	Intermediate Similarity	NPC471482
0.8037	Intermediate Similarity	NPC473567
0.8037	Intermediate Similarity	NPC216595
0.8022	Intermediate Similarity	NPC96362
0.8022	Intermediate Similarity	NPC209944
0.8022	Intermediate Similarity	NPC164840
0.8022	Intermediate Similarity	NPC234193
0.8022	Intermediate Similarity	NPC241290
0.8021	Intermediate Similarity	NPC109744
0.8021	Intermediate Similarity	NPC128066
0.802	Intermediate Similarity	NPC469942
0.802	Intermediate Similarity	NPC473510
0.802	Intermediate Similarity	NPC471242
0.8019	Intermediate Similarity	NPC170974
0.8019	Intermediate Similarity	NPC472215
0.8019	Intermediate Similarity	NPC103627
0.8019	Intermediate Similarity	NPC472214
0.8019	Intermediate Similarity	NPC191439
0.8019	Intermediate Similarity	NPC65155
0.8	Intermediate Similarity	NPC189777
0.8	Intermediate Similarity	NPC316604
0.8	Intermediate Similarity	NPC477226
0.8	Intermediate Similarity	NPC210337
0.8	Intermediate Similarity	NPC472897
0.8	Intermediate Similarity	NPC475033
0.8	Intermediate Similarity	NPC275910
0.8	Intermediate Similarity	NPC475032
0.8	Intermediate Similarity	NPC476948
0.8	Intermediate Similarity	NPC472896
0.8	Intermediate Similarity	NPC304083
0.8	Intermediate Similarity	NPC470620
0.7981	Intermediate Similarity	NPC474015
0.7979	Intermediate Similarity	NPC290731
0.7979	Intermediate Similarity	NPC157257
0.7979	Intermediate Similarity	NPC266511
0.7963	Intermediate Similarity	NPC317210
0.7961	Intermediate Similarity	NPC471887
0.7961	Intermediate Similarity	NPC471450
0.7961	Intermediate Similarity	NPC471885
0.7961	Intermediate Similarity	NPC475701
0.7961	Intermediate Similarity	NPC471888
0.7961	Intermediate Similarity	NPC471886
0.7961	Intermediate Similarity	NPC473198
0.7957	Intermediate Similarity	NPC113978
0.7957	Intermediate Similarity	NPC82623
0.7944	Intermediate Similarity	NPC65034
0.7944	Intermediate Similarity	NPC472987
0.7944	Intermediate Similarity	NPC470076
0.7944	Intermediate Similarity	NPC208189
0.7944	Intermediate Similarity	NPC473021
0.7935	Intermediate Similarity	NPC6707
0.7935	Intermediate Similarity	NPC474531
0.7935	Intermediate Similarity	NPC47761
0.7935	Intermediate Similarity	NPC70927
0.7925	Intermediate Similarity	NPC473328
0.7925	Intermediate Similarity	NPC128133
0.7925	Intermediate Similarity	NPC28844
0.7925	Intermediate Similarity	NPC473318
0.7921	Intermediate Similarity	NPC275865
0.7921	Intermediate Similarity	NPC102426
0.7921	Intermediate Similarity	NPC158088
0.7921	Intermediate Similarity	NPC300179

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 NPC261807 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1736
0.2-0.3	4121
0.3-0.4	2154
0.4-0.5	558
0.5-0.6	244
0.6-0.7	133
0.7-0.8	20
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
0.8	Intermediate Similarity	NPD7524	Approved
0.7872	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD6695	Phase 3
0.7634	Intermediate Similarity	NPD6931	Approved
0.7634	Intermediate Similarity	NPD7525	Registered
0.7634	Intermediate Similarity	NPD6930	Phase 2
0.7634	Intermediate Similarity	NPD7514	Phase 3
0.7629	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD6902	Approved
0.7527	Intermediate Similarity	NPD6929	Approved
0.7473	Intermediate Similarity	NPD7339	Approved
0.7473	Intermediate Similarity	NPD6942	Approved
0.7449	Intermediate Similarity	NPD7750	Discontinued
0.7447	Intermediate Similarity	NPD7332	Phase 2
0.7434	Intermediate Similarity	NPD7115	Discovery
0.7429	Intermediate Similarity	NPD4159	Approved
0.7429	Intermediate Similarity	NPD5344	Discontinued
0.7419	Intermediate Similarity	NPD7145	Approved
0.7312	Intermediate Similarity	NPD6932	Approved
0.7312	Intermediate Similarity	NPD6925	Approved
0.7312	Intermediate Similarity	NPD5776	Phase 2
0.7245	Intermediate Similarity	NPD6893	Approved
0.7217	Intermediate Similarity	NPD7327	Approved
0.7217	Intermediate Similarity	NPD7328	Approved
0.7204	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6933	Approved
0.717	Intermediate Similarity	NPD7640	Approved
0.717	Intermediate Similarity	NPD7639	Approved
0.7158	Intermediate Similarity	NPD7645	Phase 2
0.7157	Intermediate Similarity	NPD7087	Discontinued
0.7155	Intermediate Similarity	NPD7516	Approved
0.7117	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8264	Approved
0.7083	Intermediate Similarity	NPD4748	Discontinued
0.7075	Intermediate Similarity	NPD7638	Approved
0.7034	Intermediate Similarity	NPD8379	Approved
0.7034	Intermediate Similarity	NPD8378	Approved
0.7034	Intermediate Similarity	NPD7503	Approved
0.7034	Intermediate Similarity	NPD8380	Approved
0.7034	Intermediate Similarity	NPD8335	Approved
0.7034	Intermediate Similarity	NPD8033	Approved
0.7034	Intermediate Similarity	NPD8296	Approved
0.701	Intermediate Similarity	NPD6898	Phase 1
0.7009	Intermediate Similarity	NPD6648	Approved
0.699	Remote Similarity	NPD7637	Suspended
0.6989	Remote Similarity	NPD6924	Approved
0.6989	Remote Similarity	NPD6926	Approved
0.6989	Remote Similarity	NPD4785	Approved
0.6989	Remote Similarity	NPD4784	Approved
0.6979	Remote Similarity	NPD6683	Phase 2
0.697	Remote Similarity	NPD4786	Approved
0.6949	Remote Similarity	NPD8294	Approved
0.6949	Remote Similarity	NPD8377	Approved
0.6881	Remote Similarity	NPD5211	Phase 2
0.6875	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.687	Remote Similarity	NPD4632	Approved
0.6827	Remote Similarity	NPD6079	Approved
0.6807	Remote Similarity	NPD6054	Approved
0.6807	Remote Similarity	NPD6319	Approved
0.6796	Remote Similarity	NPD5328	Approved
0.6786	Remote Similarity	NPD6412	Phase 2
0.6783	Remote Similarity	NPD8297	Approved
0.6774	Remote Similarity	NPD4243	Approved
0.6774	Remote Similarity	NPD7150	Approved
0.6774	Remote Similarity	NPD7151	Approved
0.6774	Remote Similarity	NPD7152	Approved
0.6768	Remote Similarity	NPD3667	Approved
0.6762	Remote Similarity	NPD6399	Phase 3
0.6762	Remote Similarity	NPD4202	Approved
0.6759	Remote Similarity	NPD4225	Approved
0.6757	Remote Similarity	NPD5141	Approved
0.6754	Remote Similarity	NPD4634	Approved
0.6754	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7509	Discontinued
0.6731	Remote Similarity	NPD3168	Discontinued
0.6726	Remote Similarity	NPD6899	Approved
0.6726	Remote Similarity	NPD6881	Approved
0.6697	Remote Similarity	NPD5285	Approved
0.6697	Remote Similarity	NPD5286	Approved
0.6697	Remote Similarity	NPD4696	Approved
0.6696	Remote Similarity	NPD6675	Approved
0.6696	Remote Similarity	NPD6008	Approved
0.6696	Remote Similarity	NPD7128	Approved
0.6696	Remote Similarity	NPD6402	Approved
0.6696	Remote Similarity	NPD5739	Approved
0.6694	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD7144	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD7143	Approved
0.6667	Remote Similarity	NPD7507	Approved
0.664	Remote Similarity	NPD7319	Approved
0.6639	Remote Similarity	NPD7604	Phase 2
0.6637	Remote Similarity	NPD5697	Approved
0.6612	Remote Similarity	NPD6016	Approved
0.6612	Remote Similarity	NPD6015	Approved
0.6609	Remote Similarity	NPD7290	Approved
0.6609	Remote Similarity	NPD7102	Approved
0.6609	Remote Similarity	NPD6883	Approved
0.6585	Remote Similarity	NPD7492	Approved
0.6579	Remote Similarity	NPD7320	Approved
0.6577	Remote Similarity	NPD4633	Approved
0.6577	Remote Similarity	NPD5225	Approved
0.6577	Remote Similarity	NPD7632	Discontinued
0.6577	Remote Similarity	NPD5224	Approved
0.6577	Remote Similarity	NPD5226	Approved
0.6559	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6923	Approved
0.6559	Remote Similarity	NPD6922	Approved
0.6557	Remote Similarity	NPD5988	Approved
0.6555	Remote Similarity	NPD6009	Approved
0.6552	Remote Similarity	NPD6617	Approved
0.6552	Remote Similarity	NPD6869	Approved
0.6552	Remote Similarity	NPD6847	Approved
0.6552	Remote Similarity	NPD8130	Phase 1
0.6552	Remote Similarity	NPD6649	Approved
0.6552	Remote Similarity	NPD6650	Approved
0.6549	Remote Similarity	NPD6640	Phase 3
0.6545	Remote Similarity	NPD4700	Approved
0.6532	Remote Similarity	NPD6616	Approved
0.6522	Remote Similarity	NPD6014	Approved
0.6522	Remote Similarity	NPD6373	Approved
0.6522	Remote Similarity	NPD6013	Approved
0.6522	Remote Similarity	NPD6372	Approved
0.6522	Remote Similarity	NPD6012	Approved
0.6518	Remote Similarity	NPD5174	Approved
0.6518	Remote Similarity	NPD5175	Approved
0.6496	Remote Similarity	NPD6882	Approved
0.6491	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5701	Approved
0.6486	Remote Similarity	NPD5223	Approved
0.648	Remote Similarity	NPD7078	Approved
0.6476	Remote Similarity	NPD6051	Approved
0.6475	Remote Similarity	NPD5983	Phase 2
0.6465	Remote Similarity	NPD4195	Approved
0.6449	Remote Similarity	NPD5778	Approved
0.6449	Remote Similarity	NPD5779	Approved
0.6435	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6011	Approved
0.6435	Remote Similarity	NPD6686	Approved
0.6429	Remote Similarity	NPD7736	Approved
0.6422	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5222	Approved
0.6422	Remote Similarity	NPD5221	Approved
0.6415	Remote Similarity	NPD7838	Discovery
0.6415	Remote Similarity	NPD7136	Phase 2
0.64	Remote Similarity	NPD6336	Discontinued
0.6393	Remote Similarity	NPD7741	Discontinued
0.6392	Remote Similarity	NPD5275	Approved
0.6392	Remote Similarity	NPD4190	Phase 3
0.6379	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6084	Phase 2
0.6364	Remote Similarity	NPD6083	Phase 2
0.6364	Remote Similarity	NPD5173	Approved
0.6356	Remote Similarity	NPD6053	Discontinued
0.6349	Remote Similarity	NPD8293	Discontinued
0.6346	Remote Similarity	NPD5279	Phase 3
0.6333	Remote Similarity	NPD368	Approved
0.633	Remote Similarity	NPD5695	Phase 3
0.6321	Remote Similarity	NPD4753	Phase 2
0.6311	Remote Similarity	NPD3666	Approved
0.6311	Remote Similarity	NPD3665	Phase 1
0.6311	Remote Similarity	NPD3133	Approved
0.6303	Remote Similarity	NPD8133	Approved
0.6293	Remote Similarity	NPD4730	Approved
0.6293	Remote Similarity	NPD4729	Approved
0.6273	Remote Similarity	NPD4697	Phase 3
0.6271	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD46	Approved
0.6262	Remote Similarity	NPD6698	Approved
0.6261	Remote Similarity	NPD5357	Phase 1
0.6261	Remote Similarity	NPD4768	Approved
0.6261	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD4754	Approved
0.621	Remote Similarity	NPD8516	Approved
0.621	Remote Similarity	NPD8515	Approved
0.621	Remote Similarity	NPD8513	Phase 3
0.621	Remote Similarity	NPD8517	Approved
0.6204	Remote Similarity	NPD6411	Approved
0.6204	Remote Similarity	NPD8035	Phase 2
0.6204	Remote Similarity	NPD8034	Phase 2
0.6196	Remote Similarity	NPD371	Approved
0.619	Remote Similarity	NPD5690	Phase 2
0.6186	Remote Similarity	NPD5249	Phase 3
0.6186	Remote Similarity	NPD5248	Approved
0.6186	Remote Similarity	NPD4732	Discontinued
0.6186	Remote Similarity	NPD5251	Approved
0.6186	Remote Similarity	NPD5247	Approved
0.6186	Remote Similarity	NPD5250	Approved
0.6186	Remote Similarity	NPD6371	Approved
0.6182	Remote Similarity	NPD4629	Approved
0.6182	Remote Similarity	NPD5210	Approved
0.6179	Remote Similarity	NPD7100	Approved
0.6179	Remote Similarity	NPD7101	Approved
0.6172	Remote Similarity	NPD6033	Approved
0.6161	Remote Similarity	NPD5290	Discontinued
0.6154	Remote Similarity	NPD5128	Approved
0.6154	Remote Similarity	NPD3668	Phase 3

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