NPASS Compound

Structure

NPC210717 OpenBabel07101718182D 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 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 1 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 2 0 0 0 0 21 26 1 0 0 0 0 22 23 1 0 0 0 0 22 27 1 1 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:	4.976
LogD:	4.242
LogS:	-5.342
# 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:	5.739
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:	-4.711
MDCK Permeability:	2.9754046408925205e-05
Pgp-inhibitor:	0.065
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.837
30% Bioavailability (F30%):	0.557

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.283
Plasma Protein Binding (PPB):	89.1905746459961%
Volume Distribution (VD):	1.157
Pgp-substrate:	1.4439213275909424%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.509
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.928
CYP2C9-inhibitor:	0.229
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.178
CYP3A4-inhibitor:	0.877
CYP3A4-substrate:	0.851

ADMET: Excretion

Clearance (CL):	5.816
Half-life (T1/2):	0.059

ADMET: Toxicity

hERG Blockers:	0.099
Human Hepatotoxicity (H-HT):	0.181
Drug-inuced Liver Injury (DILI):	0.108
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.927
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.106
Carcinogencity:	0.07
Eye Corrosion:	0.007
Eye Irritation:	0.033
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC210717

Natural Product ID:	NPC210717
*Common Name:**	Topsentisterol B5
IUPAC Name:	n.a.
Synonyms:	Topsentisterol B5
Standard InCHIKey:	MEIJIKXWOMTKCH-ONOMXDCASA-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/h7-8,16-20,22,24-25,29-30H,9-15H2,1-6H3/b8-7+/t17-,18-,19+,20-,22+,24+,25+,26-,27-,28+/m1/s1
SMILES:	CC(C)[C@H](C)/C=C/[C@@H](C)[C@H]1CCC2=C3[C@H](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:	CHEMBL492817
PubChem CID:	16099499
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.	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	=	13.9	ug ml-1	PMID[514298]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	7.9	ug ml-1	PMID[514298]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	5.5	ug ml-1	PMID[514298]
NPT574	Cell Line	XF498	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[514298]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	18.4	ug ml-1	PMID[514298]

☑ 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 NPC210717 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	219
0.1-0.2	1433
0.2-0.3	4929
0.3-0.4	10984
0.4-0.5	11887
0.5-0.6	6702
0.6-0.7	5094
0.7-0.8	1337
0.8-0.85	78
0.85-0.9	30
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC103165
0.9551	High Similarity	NPC114389
0.9457	High Similarity	NPC261807
0.9032	High Similarity	NPC8774
0.9022	High Similarity	NPC137461
0.9022	High Similarity	NPC119379
0.9011	High Similarity	NPC204188
0.9011	High Similarity	NPC329596
0.9011	High Similarity	NPC80561
0.9011	High Similarity	NPC3345
0.9011	High Similarity	NPC291484
0.9011	High Similarity	NPC11216
0.8936	High Similarity	NPC227583
0.8936	High Similarity	NPC72204
0.8936	High Similarity	NPC98457
0.8936	High Similarity	NPC12103
0.8936	High Similarity	NPC288970
0.8925	High Similarity	NPC127718
0.8925	High Similarity	NPC65402
0.8913	High Similarity	NPC41554
0.8913	High Similarity	NPC97404
0.8901	High Similarity	NPC470361
0.8791	High Similarity	NPC133588
0.8646	High Similarity	NPC476040
0.8646	High Similarity	NPC476021
0.8646	High Similarity	NPC474994
0.8617	High Similarity	NPC310013
0.8602	High Similarity	NPC191323
0.8587	High Similarity	NPC474668
0.8571	High Similarity	NPC476896
0.8571	High Similarity	NPC299068
0.8571	High Similarity	NPC125399
0.8526	High Similarity	NPC144202
0.8511	High Similarity	NPC275671
0.8511	High Similarity	NPC210268
0.8495	Intermediate Similarity	NPC115607
0.8462	Intermediate Similarity	NPC470360
0.8447	Intermediate Similarity	NPC472214
0.8447	Intermediate Similarity	NPC472215
0.8444	Intermediate Similarity	NPC477978
0.8427	Intermediate Similarity	NPC249423
0.8421	Intermediate Similarity	NPC27531
0.8404	Intermediate Similarity	NPC295668
0.8384	Intermediate Similarity	NPC475617
0.837	Intermediate Similarity	NPC6391
0.837	Intermediate Similarity	NPC94462
0.837	Intermediate Similarity	NPC255143
0.837	Intermediate Similarity	NPC261266
0.8367	Intermediate Similarity	NPC476895
0.8352	Intermediate Similarity	NPC474047
0.8317	Intermediate Similarity	NPC473543
0.8315	Intermediate Similarity	NPC287749
0.8315	Intermediate Similarity	NPC96362
0.8298	Intermediate Similarity	NPC97103
0.828	Intermediate Similarity	NPC476948
0.8265	Intermediate Similarity	NPC476893
0.8252	Intermediate Similarity	NPC472218
0.8252	Intermediate Similarity	NPC472219
0.8252	Intermediate Similarity	NPC472217
0.8242	Intermediate Similarity	NPC317458
0.8242	Intermediate Similarity	NPC475789
0.8222	Intermediate Similarity	NPC476646
0.8218	Intermediate Similarity	NPC474124
0.8218	Intermediate Similarity	NPC473523
0.8211	Intermediate Similarity	NPC270511
0.8211	Intermediate Similarity	NPC192437
0.8211	Intermediate Similarity	NPC475751
0.8211	Intermediate Similarity	NPC14380
0.8211	Intermediate Similarity	NPC245410
0.8211	Intermediate Similarity	NPC470390
0.8211	Intermediate Similarity	NPC473956
0.8191	Intermediate Similarity	NPC473436
0.8191	Intermediate Similarity	NPC67872
0.8172	Intermediate Similarity	NPC71520
0.8172	Intermediate Similarity	NPC269058
0.8163	Intermediate Similarity	NPC471903
0.8152	Intermediate Similarity	NPC86238
0.8152	Intermediate Similarity	NPC205845
0.8152	Intermediate Similarity	NPC15534
0.8152	Intermediate Similarity	NPC185568
0.8144	Intermediate Similarity	NPC477605
0.8137	Intermediate Similarity	NPC75608
0.8132	Intermediate Similarity	NPC50964
0.8132	Intermediate Similarity	NPC49964
0.8119	Intermediate Similarity	NPC475344
0.8119	Intermediate Similarity	NPC476471
0.8113	Intermediate Similarity	NPC477050
0.8105	Intermediate Similarity	NPC101886
0.8105	Intermediate Similarity	NPC128066
0.8105	Intermediate Similarity	NPC477917
0.8105	Intermediate Similarity	NPC259875
0.8105	Intermediate Similarity	NPC187785
0.8105	Intermediate Similarity	NPC109744
0.8105	Intermediate Similarity	NPC138974
0.81	Intermediate Similarity	NPC473510
0.81	Intermediate Similarity	NPC324598
0.809	Intermediate Similarity	NPC476314
0.8085	Intermediate Similarity	NPC470620
0.8085	Intermediate Similarity	NPC149224
0.8085	Intermediate Similarity	NPC189777
0.8081	Intermediate Similarity	NPC316604
0.8081	Intermediate Similarity	NPC477226
0.8081	Intermediate Similarity	NPC210337
0.8081	Intermediate Similarity	NPC240372
0.8081	Intermediate Similarity	NPC475033
0.8081	Intermediate Similarity	NPC475032
0.8081	Intermediate Similarity	NPC26307
0.8065	Intermediate Similarity	NPC474189
0.8065	Intermediate Similarity	NPC290731
0.8065	Intermediate Similarity	NPC474349
0.8065	Intermediate Similarity	NPC274448
0.8061	Intermediate Similarity	NPC476894
0.8058	Intermediate Similarity	NPC472898
0.8058	Intermediate Similarity	NPC472899
0.8058	Intermediate Similarity	NPC472900
0.8043	Intermediate Similarity	NPC474634
0.8041	Intermediate Similarity	NPC307776
0.8041	Intermediate Similarity	NPC98193
0.8037	Intermediate Similarity	NPC317210
0.8022	Intermediate Similarity	NPC474531
0.8022	Intermediate Similarity	NPC471270
0.8022	Intermediate Similarity	NPC470383
0.8022	Intermediate Similarity	NPC209620
0.8022	Intermediate Similarity	NPC23852
0.8022	Intermediate Similarity	NPC264245
0.802	Intermediate Similarity	NPC96784
0.802	Intermediate Similarity	NPC470434
0.802	Intermediate Similarity	NPC476897
0.802	Intermediate Similarity	NPC235920
0.8	Intermediate Similarity	NPC472901
0.8	Intermediate Similarity	NPC475664
0.8	Intermediate Similarity	NPC4574
0.8	Intermediate Similarity	NPC300179
0.8	Intermediate Similarity	NPC284828
0.8	Intermediate Similarity	NPC212596
0.8	Intermediate Similarity	NPC102426
0.8	Intermediate Similarity	NPC173905
0.8	Intermediate Similarity	NPC216260
0.8	Intermediate Similarity	NPC5358
0.8	Intermediate Similarity	NPC472216
0.8	Intermediate Similarity	NPC5475
0.8	Intermediate Similarity	NPC280556
0.7981	Intermediate Similarity	NPC476594
0.7981	Intermediate Similarity	NPC33053
0.798	Intermediate Similarity	NPC90583
0.798	Intermediate Similarity	NPC54248
0.798	Intermediate Similarity	NPC88009
0.798	Intermediate Similarity	NPC276103
0.7979	Intermediate Similarity	NPC476217
0.7979	Intermediate Similarity	NPC293287
0.7979	Intermediate Similarity	NPC152808
0.7959	Intermediate Similarity	NPC473258
0.7957	Intermediate Similarity	NPC470077
0.7957	Intermediate Similarity	NPC83702
0.7944	Intermediate Similarity	NPC216595
0.7944	Intermediate Similarity	NPC473567
0.7941	Intermediate Similarity	NPC300399
0.7941	Intermediate Similarity	NPC471482
0.7941	Intermediate Similarity	NPC471889
0.7935	Intermediate Similarity	NPC296701
0.7935	Intermediate Similarity	NPC30166
0.7935	Intermediate Similarity	NPC87489
0.7935	Intermediate Similarity	NPC259858
0.7935	Intermediate Similarity	NPC101462
0.7935	Intermediate Similarity	NPC218616
0.7925	Intermediate Similarity	NPC103627
0.7925	Intermediate Similarity	NPC65155
0.7925	Intermediate Similarity	NPC191439
0.7925	Intermediate Similarity	NPC170974
0.7921	Intermediate Similarity	NPC230546
0.7921	Intermediate Similarity	NPC469942
0.7921	Intermediate Similarity	NPC471242
0.7921	Intermediate Similarity	NPC38855
0.7917	Intermediate Similarity	NPC105495
0.7917	Intermediate Similarity	NPC49783
0.7912	Intermediate Similarity	NPC471266
0.7912	Intermediate Similarity	NPC236112
0.7912	Intermediate Similarity	NPC236707
0.7912	Intermediate Similarity	NPC209944
0.7912	Intermediate Similarity	NPC164840
0.7912	Intermediate Similarity	NPC95124
0.7912	Intermediate Similarity	NPC234193
0.7912	Intermediate Similarity	NPC241290
0.7905	Intermediate Similarity	NPC472896
0.7905	Intermediate Similarity	NPC472897
0.7895	Intermediate Similarity	NPC304083
0.7895	Intermediate Similarity	NPC186145
0.7895	Intermediate Similarity	NPC474657
0.7895	Intermediate Similarity	NPC233744
0.7889	Intermediate Similarity	NPC83351
0.7889	Intermediate Similarity	NPC52755
0.7889	Intermediate Similarity	NPC167891
0.7885	Intermediate Similarity	NPC474015
0.7872	Intermediate Similarity	NPC157257
0.7872	Intermediate Similarity	NPC298595
0.7872	Intermediate Similarity	NPC266511
0.7865	Intermediate Similarity	NPC253190
0.7864	Intermediate Similarity	NPC471887
0.7864	Intermediate Similarity	NPC471888
0.7864	Intermediate Similarity	NPC475701

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 NPC210717 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	1608
0.2-0.3	4129
0.3-0.4	2166
0.4-0.5	630
0.5-0.6	218
0.6-0.7	174
0.7-0.8	28
0.8-0.85	1
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
0.7957	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6695	Phase 3
0.7717	Intermediate Similarity	NPD6931	Approved
0.7717	Intermediate Similarity	NPD7514	Phase 3
0.7717	Intermediate Similarity	NPD6930	Phase 2
0.767	Intermediate Similarity	NPD4159	Approved
0.767	Intermediate Similarity	NPD5344	Discontinued
0.7634	Intermediate Similarity	NPD6902	Approved
0.7609	Intermediate Similarity	NPD6929	Approved
0.7527	Intermediate Similarity	NPD7332	Phase 2
0.7527	Intermediate Similarity	NPD7525	Registered
0.7526	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7750	Discontinued
0.75	Intermediate Similarity	NPD7145	Approved
0.7391	Intermediate Similarity	NPD5776	Phase 2
0.7391	Intermediate Similarity	NPD6932	Approved
0.7391	Intermediate Similarity	NPD6925	Approved
0.7363	Intermediate Similarity	NPD7339	Approved
0.7363	Intermediate Similarity	NPD6942	Approved
0.7345	Intermediate Similarity	NPD7115	Discovery
0.7339	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6893	Approved
0.7283	Intermediate Similarity	NPD6933	Approved
0.7283	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7640	Approved
0.7238	Intermediate Similarity	NPD6648	Approved
0.7238	Intermediate Similarity	NPD7639	Approved
0.7234	Intermediate Similarity	NPD7645	Phase 2
0.7228	Intermediate Similarity	NPD7087	Discontinued
0.7217	Intermediate Similarity	NPD7516	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.713	Intermediate Similarity	NPD7328	Approved
0.713	Intermediate Similarity	NPD7327	Approved
0.7083	Intermediate Similarity	NPD6898	Phase 1
0.7065	Intermediate Similarity	NPD6924	Approved
0.7065	Intermediate Similarity	NPD6926	Approved
0.7059	Intermediate Similarity	NPD7637	Suspended
0.7053	Intermediate Similarity	NPD6683	Phase 2
0.6989	Remote Similarity	NPD8264	Approved
0.6981	Remote Similarity	NPD4225	Approved
0.6964	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD3168	Discontinued
0.6949	Remote Similarity	NPD7503	Approved
0.6949	Remote Similarity	NPD8379	Approved
0.6949	Remote Similarity	NPD8033	Approved
0.6949	Remote Similarity	NPD8380	Approved
0.6949	Remote Similarity	NPD8296	Approved
0.6949	Remote Similarity	NPD8378	Approved
0.6949	Remote Similarity	NPD8335	Approved
0.6947	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4785	Approved
0.6882	Remote Similarity	NPD4784	Approved
0.6869	Remote Similarity	NPD4786	Approved
0.6864	Remote Similarity	NPD8377	Approved
0.6864	Remote Similarity	NPD8294	Approved
0.6848	Remote Similarity	NPD7150	Approved
0.6848	Remote Similarity	NPD7151	Approved
0.6848	Remote Similarity	NPD7152	Approved
0.6847	Remote Similarity	NPD6412	Phase 2
0.6837	Remote Similarity	NPD3667	Approved
0.6804	Remote Similarity	NPD7509	Discontinued
0.6789	Remote Similarity	NPD5211	Phase 2
0.6783	Remote Similarity	NPD4632	Approved
0.6739	Remote Similarity	NPD7144	Approved
0.6739	Remote Similarity	NPD7143	Approved
0.6733	Remote Similarity	NPD3618	Phase 1
0.6731	Remote Similarity	NPD6079	Approved
0.6723	Remote Similarity	NPD6054	Approved
0.6723	Remote Similarity	NPD6319	Approved
0.6699	Remote Similarity	NPD5328	Approved
0.6696	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD4243	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD5141	Approved
0.6637	Remote Similarity	NPD6881	Approved
0.6637	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6899	Approved
0.6637	Remote Similarity	NPD6686	Approved
0.6636	Remote Similarity	NPD7632	Discontinued
0.6633	Remote Similarity	NPD4748	Discontinued
0.663	Remote Similarity	NPD6923	Approved
0.663	Remote Similarity	NPD6922	Approved
0.6612	Remote Similarity	NPD6370	Approved
0.6607	Remote Similarity	NPD5739	Approved
0.6607	Remote Similarity	NPD6640	Phase 3
0.6607	Remote Similarity	NPD6008	Approved
0.6607	Remote Similarity	NPD6675	Approved
0.6607	Remote Similarity	NPD7128	Approved
0.6607	Remote Similarity	NPD6402	Approved
0.6606	Remote Similarity	NPD5285	Approved
0.6606	Remote Similarity	NPD4696	Approved
0.6606	Remote Similarity	NPD5286	Approved
0.6585	Remote Similarity	NPD7507	Approved
0.6583	Remote Similarity	NPD6059	Approved
0.6574	Remote Similarity	NPD4755	Approved
0.656	Remote Similarity	NPD7319	Approved
0.6557	Remote Similarity	NPD7604	Phase 2
0.6549	Remote Similarity	NPD5697	Approved
0.6529	Remote Similarity	NPD6016	Approved
0.6529	Remote Similarity	NPD6015	Approved
0.6522	Remote Similarity	NPD6883	Approved
0.6522	Remote Similarity	NPD7290	Approved
0.6522	Remote Similarity	NPD7102	Approved
0.6504	Remote Similarity	NPD7492	Approved
0.6491	Remote Similarity	NPD7320	Approved
0.6486	Remote Similarity	NPD4633	Approved
0.6486	Remote Similarity	NPD5224	Approved
0.6486	Remote Similarity	NPD5225	Approved
0.6486	Remote Similarity	NPD5226	Approved
0.6476	Remote Similarity	NPD7838	Discovery
0.6476	Remote Similarity	NPD7136	Phase 2
0.6475	Remote Similarity	NPD5988	Approved
0.6471	Remote Similarity	NPD6009	Approved
0.6466	Remote Similarity	NPD8130	Phase 1
0.6466	Remote Similarity	NPD6650	Approved
0.6466	Remote Similarity	NPD6847	Approved
0.6466	Remote Similarity	NPD6649	Approved
0.6466	Remote Similarity	NPD6869	Approved
0.6466	Remote Similarity	NPD6617	Approved
0.646	Remote Similarity	NPD5357	Phase 1
0.6455	Remote Similarity	NPD4700	Approved
0.6452	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6616	Approved
0.6446	Remote Similarity	NPD7741	Discontinued
0.6435	Remote Similarity	NPD6014	Approved
0.6435	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6013	Approved
0.6435	Remote Similarity	NPD6372	Approved
0.6435	Remote Similarity	NPD6012	Approved
0.6435	Remote Similarity	NPD6373	Approved
0.6429	Remote Similarity	NPD5174	Approved
0.6429	Remote Similarity	NPD5175	Approved
0.641	Remote Similarity	NPD6882	Approved
0.6404	Remote Similarity	NPD5701	Approved
0.64	Remote Similarity	NPD7078	Approved
0.6396	Remote Similarity	NPD5223	Approved
0.6393	Remote Similarity	NPD5983	Phase 2
0.6381	Remote Similarity	NPD6051	Approved
0.6373	Remote Similarity	NPD3133	Approved
0.6373	Remote Similarity	NPD3666	Approved
0.6373	Remote Similarity	NPD3665	Phase 1
0.6364	Remote Similarity	NPD4195	Approved
0.6355	Remote Similarity	NPD5778	Approved
0.6355	Remote Similarity	NPD5779	Approved
0.6349	Remote Similarity	NPD7736	Approved
0.6348	Remote Similarity	NPD6011	Approved
0.6339	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5221	Approved
0.633	Remote Similarity	NPD5222	Approved
0.633	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6698	Approved
0.6321	Remote Similarity	NPD46	Approved
0.632	Remote Similarity	NPD6336	Discontinued
0.6289	Remote Similarity	NPD5275	Approved
0.6289	Remote Similarity	NPD4190	Phase 3
0.6273	Remote Similarity	NPD6083	Phase 2
0.6273	Remote Similarity	NPD6084	Phase 2
0.6273	Remote Similarity	NPD5173	Approved
0.627	Remote Similarity	NPD8293	Discontinued
0.6264	Remote Similarity	NPD371	Approved
0.625	Remote Similarity	NPD4732	Discontinued
0.6226	Remote Similarity	NPD4753	Phase 2
0.6222	Remote Similarity	NPD368	Approved
0.6218	Remote Similarity	NPD8133	Approved
0.6216	Remote Similarity	NPD5290	Discontinued
0.6214	Remote Similarity	NPD3668	Phase 3
0.6207	Remote Similarity	NPD4729	Approved
0.6207	Remote Similarity	NPD4730	Approved
0.619	Remote Similarity	NPD4250	Approved
0.619	Remote Similarity	NPD4251	Approved
0.6186	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD4697	Phase 3
0.6174	Remote Similarity	NPD4767	Approved
0.6174	Remote Similarity	NPD4768	Approved
0.616	Remote Similarity	NPD6067	Discontinued
0.6154	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD7748	Approved
0.614	Remote Similarity	NPD4754	Approved
0.6139	Remote Similarity	NPD4822	Approved
0.6139	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4819	Approved
0.6139	Remote Similarity	NPD4820	Approved
0.6139	Remote Similarity	NPD4821	Approved
0.6134	Remote Similarity	NPD6053	Discontinued
0.6129	Remote Similarity	NPD8516	Approved
0.6129	Remote Similarity	NPD8517	Approved
0.6129	Remote Similarity	NPD8515	Approved
0.6129	Remote Similarity	NPD8513	Phase 3
0.6126	Remote Similarity	NPD7902	Approved
0.6111	Remote Similarity	NPD7515	Phase 2
0.6111	Remote Similarity	NPD8035	Phase 2
0.6111	Remote Similarity	NPD6411	Approved
0.6111	Remote Similarity	NPD8034	Phase 2
0.6111	Remote Similarity	NPD7983	Approved
0.6102	Remote Similarity	NPD5247	Approved
0.6102	Remote Similarity	NPD5248	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