NPASS Compound

Structure

NPC475025 OpenBabel07101719522D 29 33 0 0 1 0 0 0 0 0999 V2000 1.5811 -6.6327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9568 -4.7114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9725 -2.6695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3008 -2.1094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9126 -0.6816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2570 -5.8821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6621 0.3285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6621 1.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6207 -4.1708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3086 -3.2101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2661 -0.6816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6723 0.1356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0378 -1.1867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7874 -0.1766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7874 1.8436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8369 -1.6917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0378 1.8436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8369 1.3386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9448 -4.9214 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.9845 -2.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6723 -1.4988 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7117 -0.1766 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0378 -0.1766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7117 -1.1867 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9126 0.3285 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9126 1.3386 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8369 0.3285 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7786 0.4495 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 6 1 0 0 0 0 2 19 1 0 0 0 0 5 25 1 0 0 0 0 6 19 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 10 2 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 16 1 0 0 0 0 13 23 2 0 0 0 0 14 25 1 0 0 0 0 16 24 1 0 0 0 0 17 18 2 0 0 0 0 17 26 1 0 0 0 0 20 3 1 6 0 0 0 20 21 1 0 0 0 0 21 24 1 6 0 0 0 22 24 1 6 0 0 0 22 27 1 0 0 0 0 23 25 1 0 0 0 0 23 27 1 0 0 0 0 24 4 1 6 0 0 0 25 26 1 6 0 0 0 26 15 1 1 0 0 0 26 28 1 0 0 0 0 27 18 1 6 0 0 0 27 29 1 0 0 0 0 28 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.3
Volume:	442.437
LogP:	6.792
LogD:	5.437
LogS:	-6.563
# Rotatable Bonds:	4
TPSA:	18.46
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.37
Synthetic Accessibility Score:	6.824
Fsp3:	0.778
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.664
MDCK Permeability:	1.7701639080769382e-05
Pgp-inhibitor:	0.031
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.119
30% Bioavailability (F30%):	0.118

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.19
Plasma Protein Binding (PPB):	94.94514465332031%
Volume Distribution (VD):	1.312
Pgp-substrate:	1.8829278945922852%

ADMET: Metabolism

CYP1A2-inhibitor:	0.065
CYP1A2-substrate:	0.954
CYP2C19-inhibitor:	0.525
CYP2C19-substrate:	0.951
CYP2C9-inhibitor:	0.584
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.525
CYP2D6-substrate:	0.186
CYP3A4-inhibitor:	0.963
CYP3A4-substrate:	0.933

ADMET: Excretion

Clearance (CL):	1.968
Half-life (T1/2):	0.058

ADMET: Toxicity

hERG Blockers:	0.222
Human Hepatotoxicity (H-HT):	0.466
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.55
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.088
Carcinogencity:	0.027
Eye Corrosion:	0.004
Eye Irritation:	0.038
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC475025

Natural Product ID:	NPC475025
*Common Name:**	Topsentisterol A3
IUPAC Name:	n.a.
Synonyms:	Topsentisterol A3
Standard InCHIKey:	CZLIBAKQDCPVLQ-ZALMTFRLSA-N
Standard InCHI:	InChI=1S/C27H40O2/c1-6-19(2)9-10-20(3)21-11-12-22-24(21,4)16-13-23-25(5)14-7-8-15-26(25)17-18-27(22,23)29-28-26/h9-10,13,17-22H,6-8,11-12,14-16H2,1-5H3/b10-9+/t19?,20-,21-,22-,24-,25-,26+,27+/m1/s1
SMILES:	CCC(C)C=CC(C)C1CCC2C1(CC=C3C24C=CC5(C3(CCCC5)C)OO4)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL492609
PubChem CID:	44566387
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid 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	=	5.4	ug ml-1	PMID[465271]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	7.1	ug ml-1	PMID[465271]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	4.6	ug ml-1	PMID[465271]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	6.2	ug ml-1	PMID[465271]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	4.2	ug ml-1	PMID[465271]

☑ 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 NPC475025 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	244
0.1-0.2	1667
0.2-0.3	9507
0.3-0.4	15801
0.4-0.5	7675
0.5-0.6	5906
0.6-0.7	1664
0.7-0.8	223
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9722	High Similarity	NPC475027
0.9452	High Similarity	NPC474230
0.9315	High Similarity	NPC474231
0.8452	Intermediate Similarity	NPC14380
0.825	Intermediate Similarity	NPC47761
0.8235	Intermediate Similarity	NPC245410
0.8235	Intermediate Similarity	NPC192437
0.8235	Intermediate Similarity	NPC270511
0.8235	Intermediate Similarity	NPC470390
0.8148	Intermediate Similarity	NPC49964
0.8133	Intermediate Similarity	NPC475728
0.8118	Intermediate Similarity	NPC101886
0.8025	Intermediate Similarity	NPC264245
0.8	Intermediate Similarity	NPC4574
0.8	Intermediate Similarity	NPC212596
0.7952	Intermediate Similarity	NPC205845
0.7927	Intermediate Similarity	NPC87489
0.7922	Intermediate Similarity	NPC259049
0.7901	Intermediate Similarity	NPC241290
0.7901	Intermediate Similarity	NPC164840
0.7901	Intermediate Similarity	NPC209944
0.7901	Intermediate Similarity	NPC234193
0.7882	Intermediate Similarity	NPC304083
0.7875	Intermediate Similarity	NPC473943
0.7857	Intermediate Similarity	NPC274448
0.7857	Intermediate Similarity	NPC318390
0.7857	Intermediate Similarity	NPC157257
0.7791	Intermediate Similarity	NPC475605
0.7778	Intermediate Similarity	NPC84694
0.7778	Intermediate Similarity	NPC143182
0.7778	Intermediate Similarity	NPC81306
0.7778	Intermediate Similarity	NPC28862
0.7778	Intermediate Similarity	NPC47982
0.7778	Intermediate Similarity	NPC109546
0.7765	Intermediate Similarity	NPC261266
0.775	Intermediate Similarity	NPC198968
0.775	Intermediate Similarity	NPC155986
0.775	Intermediate Similarity	NPC318495
0.7738	Intermediate Similarity	NPC470077
0.7738	Intermediate Similarity	NPC238485
0.7738	Intermediate Similarity	NPC231310
0.7722	Intermediate Similarity	NPC133580
0.7711	Intermediate Similarity	NPC296701
0.7711	Intermediate Similarity	NPC50964
0.7711	Intermediate Similarity	NPC101462
0.7711	Intermediate Similarity	NPC218616
0.7701	Intermediate Similarity	NPC138974
0.7692	Intermediate Similarity	NPC474140
0.7674	Intermediate Similarity	NPC149224
0.7654	Intermediate Similarity	NPC477514
0.7654	Intermediate Similarity	NPC275910
0.7654	Intermediate Similarity	NPC474216
0.7647	Intermediate Similarity	NPC137493
0.7625	Intermediate Similarity	NPC107059
0.7625	Intermediate Similarity	NPC247325
0.7625	Intermediate Similarity	NPC244488
0.7625	Intermediate Similarity	NPC113733
0.7625	Intermediate Similarity	NPC240604
0.7625	Intermediate Similarity	NPC321381
0.7625	Intermediate Similarity	NPC321016
0.7625	Intermediate Similarity	NPC300324
0.7619	Intermediate Similarity	NPC475789
0.7619	Intermediate Similarity	NPC474634
0.7619	Intermediate Similarity	NPC134481
0.7619	Intermediate Similarity	NPC470384
0.7614	Intermediate Similarity	NPC3345
0.7614	Intermediate Similarity	NPC291484
0.7614	Intermediate Similarity	NPC80561
0.7614	Intermediate Similarity	NPC329596
0.7614	Intermediate Similarity	NPC204188
0.7614	Intermediate Similarity	NPC11216
0.76	Intermediate Similarity	NPC279434
0.759	Intermediate Similarity	NPC474759
0.759	Intermediate Similarity	NPC474731
0.759	Intermediate Similarity	NPC209620
0.759	Intermediate Similarity	NPC7505
0.759	Intermediate Similarity	NPC82986
0.759	Intermediate Similarity	NPC474683
0.759	Intermediate Similarity	NPC23852
0.759	Intermediate Similarity	NPC474752
0.7586	Intermediate Similarity	NPC133588
0.7561	Intermediate Similarity	NPC328714
0.7561	Intermediate Similarity	NPC209430
0.7561	Intermediate Similarity	NPC30986
0.7561	Intermediate Similarity	NPC80530
0.7561	Intermediate Similarity	NPC273410
0.7558	Intermediate Similarity	NPC6391
0.7558	Intermediate Similarity	NPC299068
0.7531	Intermediate Similarity	NPC214570
0.7531	Intermediate Similarity	NPC91594
0.7529	Intermediate Similarity	NPC15534
0.7529	Intermediate Similarity	NPC185568
0.7528	Intermediate Similarity	NPC97404
0.7528	Intermediate Similarity	NPC41554
0.7528	Intermediate Similarity	NPC471453
0.75	Intermediate Similarity	NPC285893
0.75	Intermediate Similarity	NPC189972
0.75	Intermediate Similarity	NPC5985
0.75	Intermediate Similarity	NPC470049
0.75	Intermediate Similarity	NPC136188
0.75	Intermediate Similarity	NPC471468
0.75	Intermediate Similarity	NPC28657
0.75	Intermediate Similarity	NPC304309
0.75	Intermediate Similarity	NPC202389
0.75	Intermediate Similarity	NPC470361
0.75	Intermediate Similarity	NPC230301
0.75	Intermediate Similarity	NPC134847
0.75	Intermediate Similarity	NPC162742
0.75	Intermediate Similarity	NPC288035
0.75	Intermediate Similarity	NPC22105
0.747	Intermediate Similarity	NPC236237
0.747	Intermediate Similarity	NPC322313
0.747	Intermediate Similarity	NPC102253
0.7444	Intermediate Similarity	NPC310013
0.7442	Intermediate Similarity	NPC266511
0.7442	Intermediate Similarity	NPC470360
0.7439	Intermediate Similarity	NPC6978
0.7439	Intermediate Similarity	NPC307965
0.7439	Intermediate Similarity	NPC244385
0.7439	Intermediate Similarity	NPC138621
0.7439	Intermediate Similarity	NPC475337
0.7439	Intermediate Similarity	NPC18603
0.7439	Intermediate Similarity	NPC285761
0.7439	Intermediate Similarity	NPC76931
0.7439	Intermediate Similarity	NPC477522
0.7439	Intermediate Similarity	NPC87604
0.7439	Intermediate Similarity	NPC167037
0.7416	Intermediate Similarity	NPC273199
0.7416	Intermediate Similarity	NPC295668
0.7412	Intermediate Similarity	NPC82623
0.7412	Intermediate Similarity	NPC470558
0.7412	Intermediate Similarity	NPC317458
0.7407	Intermediate Similarity	NPC46160
0.7407	Intermediate Similarity	NPC470362
0.7407	Intermediate Similarity	NPC129165
0.7407	Intermediate Similarity	NPC189883
0.7407	Intermediate Similarity	NPC265588
0.7407	Intermediate Similarity	NPC202642
0.7407	Intermediate Similarity	NPC134330
0.7407	Intermediate Similarity	NPC73875
0.7386	Intermediate Similarity	NPC474668
0.7386	Intermediate Similarity	NPC471952
0.7381	Intermediate Similarity	NPC476646
0.7381	Intermediate Similarity	NPC474531
0.7381	Intermediate Similarity	NPC70927
0.7381	Intermediate Similarity	NPC470383
0.7363	Intermediate Similarity	NPC127718
0.7363	Intermediate Similarity	NPC65402
0.7356	Intermediate Similarity	NPC152808
0.7356	Intermediate Similarity	NPC24277
0.7356	Intermediate Similarity	NPC293287
0.7349	Intermediate Similarity	NPC1319
0.7349	Intermediate Similarity	NPC44083
0.7349	Intermediate Similarity	NPC153987
0.7333	Intermediate Similarity	NPC177641
0.7326	Intermediate Similarity	NPC124172
0.7326	Intermediate Similarity	NPC474047
0.7326	Intermediate Similarity	NPC209802
0.7317	Intermediate Similarity	NPC470750
0.7317	Intermediate Similarity	NPC34019
0.7294	Intermediate Similarity	NPC1272
0.7294	Intermediate Similarity	NPC201852
0.7294	Intermediate Similarity	NPC30166
0.7294	Intermediate Similarity	NPC470614
0.7294	Intermediate Similarity	NPC248886
0.7284	Intermediate Similarity	NPC118508
0.7284	Intermediate Similarity	NPC322353
0.7284	Intermediate Similarity	NPC121744
0.7284	Intermediate Similarity	NPC291503
0.7284	Intermediate Similarity	NPC319090
0.7284	Intermediate Similarity	NPC328104
0.7284	Intermediate Similarity	NPC141071
0.7284	Intermediate Similarity	NPC471723
0.7284	Intermediate Similarity	NPC257347
0.7283	Intermediate Similarity	NPC8774
0.7273	Intermediate Similarity	NPC470620
0.7262	Intermediate Similarity	NPC236112
0.7262	Intermediate Similarity	NPC13554
0.7262	Intermediate Similarity	NPC96362
0.7262	Intermediate Similarity	NPC26117
0.725	Intermediate Similarity	NPC471799
0.7245	Intermediate Similarity	NPC64844
0.7245	Intermediate Similarity	NPC42847
0.7241	Intermediate Similarity	NPC474189
0.7241	Intermediate Similarity	NPC269638
0.7241	Intermediate Similarity	NPC474349
0.7229	Intermediate Similarity	NPC186191
0.7229	Intermediate Similarity	NPC205455
0.7229	Intermediate Similarity	NPC167891
0.7229	Intermediate Similarity	NPC83351
0.7222	Intermediate Similarity	NPC320026
0.7215	Intermediate Similarity	NPC34834
0.7209	Intermediate Similarity	NPC470047
0.7209	Intermediate Similarity	NPC207013
0.7209	Intermediate Similarity	NPC470046
0.7209	Intermediate Similarity	NPC477818
0.7204	Intermediate Similarity	NPC98457
0.7204	Intermediate Similarity	NPC227583
0.7204	Intermediate Similarity	NPC288970
0.7204	Intermediate Similarity	NPC12103

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 NPC475025 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	1732
0.2-0.3	4689
0.3-0.4	1896
0.4-0.5	317
0.5-0.6	179
0.6-0.7	119
0.7-0.8	21
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
0.8052	Intermediate Similarity	NPD4784	Approved
0.8052	Intermediate Similarity	NPD4785	Approved
0.7792	Intermediate Similarity	NPD4243	Approved
0.75	Intermediate Similarity	NPD6942	Approved
0.75	Intermediate Similarity	NPD7339	Approved
0.747	Intermediate Similarity	NPD7525	Registered
0.7349	Intermediate Similarity	NPD4195	Approved
0.7284	Intermediate Similarity	NPD4190	Phase 3
0.7284	Intermediate Similarity	NPD5275	Approved
0.7195	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6924	Approved
0.716	Intermediate Similarity	NPD6926	Approved
0.7079	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6933	Approved
0.6932	Remote Similarity	NPD4786	Approved
0.6923	Remote Similarity	NPD6051	Approved
0.6897	Remote Similarity	NPD4223	Phase 3
0.6897	Remote Similarity	NPD4221	Approved
0.686	Remote Similarity	NPD6930	Phase 2
0.686	Remote Similarity	NPD6931	Approved
0.686	Remote Similarity	NPD7514	Phase 3
0.6854	Remote Similarity	NPD5329	Approved
0.6824	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7144	Approved
0.679	Remote Similarity	NPD7143	Approved
0.6778	Remote Similarity	NPD6098	Approved
0.6778	Remote Similarity	NPD5690	Phase 2
0.6744	Remote Similarity	NPD6929	Approved
0.6744	Remote Similarity	NPD7645	Phase 2
0.6742	Remote Similarity	NPD4197	Approved
0.6742	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7151	Approved
0.6707	Remote Similarity	NPD7150	Approved
0.6707	Remote Similarity	NPD7152	Approved
0.6706	Remote Similarity	NPD6932	Approved
0.6705	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD7509	Discontinued
0.6667	Remote Similarity	NPD7332	Phase 2
0.6667	Remote Similarity	NPD6922	Approved
0.6667	Remote Similarity	NPD6923	Approved
0.6667	Remote Similarity	NPD4748	Discontinued
0.6629	Remote Similarity	NPD6695	Phase 3
0.6628	Remote Similarity	NPD7145	Approved
0.6596	Remote Similarity	NPD5281	Approved
0.6596	Remote Similarity	NPD6079	Approved
0.6596	Remote Similarity	NPD5284	Approved
0.6593	Remote Similarity	NPD4690	Approved
0.6593	Remote Similarity	NPD4623	Approved
0.6593	Remote Similarity	NPD4519	Discontinued
0.6593	Remote Similarity	NPD4688	Approved
0.6593	Remote Similarity	NPD4694	Approved
0.6593	Remote Similarity	NPD5205	Approved
0.6593	Remote Similarity	NPD5280	Approved
0.6593	Remote Similarity	NPD4138	Approved
0.6593	Remote Similarity	NPD4693	Phase 3
0.6593	Remote Similarity	NPD4689	Approved
0.6591	Remote Similarity	NPD6902	Approved
0.6585	Remote Similarity	NPD4747	Approved
0.6559	Remote Similarity	NPD5328	Approved
0.6559	Remote Similarity	NPD6904	Approved
0.6559	Remote Similarity	NPD6673	Approved
0.6559	Remote Similarity	NPD6080	Approved
0.6556	Remote Similarity	NPD3668	Phase 3
0.6548	Remote Similarity	NPD5733	Approved
0.6548	Remote Similarity	NPD4687	Approved
0.6526	Remote Similarity	NPD4202	Approved
0.6526	Remote Similarity	NPD6399	Phase 3
0.6522	Remote Similarity	NPD3573	Approved
0.6512	Remote Similarity	NPD6925	Approved
0.6512	Remote Similarity	NPD5776	Phase 2
0.6489	Remote Similarity	NPD5207	Approved
0.6484	Remote Similarity	NPD6893	Approved
0.6471	Remote Similarity	NPD8264	Approved
0.6463	Remote Similarity	NPD4137	Phase 3
0.6452	Remote Similarity	NPD6672	Approved
0.6452	Remote Similarity	NPD5737	Approved
0.6452	Remote Similarity	NPD4722	Approved
0.6452	Remote Similarity	NPD5208	Approved
0.6452	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4723	Approved
0.6421	Remote Similarity	NPD5693	Phase 1
0.6421	Remote Similarity	NPD5694	Approved
0.6421	Remote Similarity	NPD6050	Approved
0.6413	Remote Similarity	NPD7521	Approved
0.6413	Remote Similarity	NPD6409	Approved
0.6413	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD3618	Phase 1
0.6413	Remote Similarity	NPD7146	Approved
0.6413	Remote Similarity	NPD5330	Approved
0.6413	Remote Similarity	NPD7334	Approved
0.6413	Remote Similarity	NPD6684	Approved
0.6404	Remote Similarity	NPD4139	Approved
0.6404	Remote Similarity	NPD4692	Approved
0.6392	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4691	Approved
0.6383	Remote Similarity	NPD4753	Phase 2
0.6374	Remote Similarity	NPD3133	Approved
0.6374	Remote Similarity	NPD3665	Phase 1
0.6374	Remote Similarity	NPD3666	Approved
0.6364	Remote Similarity	NPD6683	Phase 2
0.6353	Remote Similarity	NPD4058	Approved
0.6344	Remote Similarity	NPD7524	Approved
0.6344	Remote Similarity	NPD7750	Discontinued
0.6341	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5211	Phase 2
0.6316	Remote Similarity	NPD5692	Phase 3
0.631	Remote Similarity	NPD5276	Approved
0.63	Remote Similarity	NPD5285	Approved
0.63	Remote Similarity	NPD4696	Approved
0.63	Remote Similarity	NPD5286	Approved
0.6289	Remote Similarity	NPD6001	Approved
0.6277	Remote Similarity	NPD4518	Approved
0.6277	Remote Similarity	NPD6903	Approved
0.6263	Remote Similarity	NPD4755	Approved
0.625	Remote Similarity	NPD3617	Approved
0.6238	Remote Similarity	NPD5223	Approved
0.6237	Remote Similarity	NPD5279	Phase 3
0.6224	Remote Similarity	NPD4629	Approved
0.6224	Remote Similarity	NPD5210	Approved
0.6222	Remote Similarity	NPD6898	Phase 1
0.6214	Remote Similarity	NPD5141	Approved
0.6203	Remote Similarity	NPD368	Approved
0.6182	Remote Similarity	NPD7115	Discovery
0.6176	Remote Similarity	NPD4633	Approved
0.6176	Remote Similarity	NPD5225	Approved
0.6176	Remote Similarity	NPD5224	Approved
0.6176	Remote Similarity	NPD5226	Approved
0.6162	Remote Similarity	NPD5221	Approved
0.6162	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5222	Approved
0.6146	Remote Similarity	NPD4096	Approved
0.6146	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4700	Approved
0.6129	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5771	Approved
0.6122	Remote Similarity	NPD5707	Approved
0.6117	Remote Similarity	NPD5174	Approved
0.6117	Remote Similarity	NPD5175	Approved
0.6111	Remote Similarity	NPD4695	Discontinued
0.6106	Remote Similarity	NPD7503	Approved
0.61	Remote Similarity	NPD6083	Phase 2
0.61	Remote Similarity	NPD5173	Approved
0.61	Remote Similarity	NPD6084	Phase 2
0.6087	Remote Similarity	NPD4788	Approved
0.6082	Remote Similarity	NPD7087	Discontinued
0.6061	Remote Similarity	NPD5695	Phase 3
0.604	Remote Similarity	NPD7638	Approved
0.6038	Remote Similarity	NPD6881	Approved
0.6038	Remote Similarity	NPD6899	Approved
0.6023	Remote Similarity	NPD1346	Approved
0.602	Remote Similarity	NPD5133	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6939	Phase 2
0.6	Remote Similarity	NPD6402	Approved
0.598	Remote Similarity	NPD7639	Approved
0.598	Remote Similarity	NPD6404	Discontinued
0.598	Remote Similarity	NPD7640	Approved
0.5962	Remote Similarity	NPD4754	Approved
0.596	Remote Similarity	NPD7900	Approved
0.596	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5697	Approved
0.5926	Remote Similarity	NPD7290	Approved
0.5926	Remote Similarity	NPD6883	Approved
0.5926	Remote Similarity	NPD7102	Approved
0.5918	Remote Similarity	NPD7637	Suspended
0.5918	Remote Similarity	NPD7515	Phase 2
0.5918	Remote Similarity	NPD8035	Phase 2
0.5918	Remote Similarity	NPD8034	Phase 2
0.59	Remote Similarity	NPD5654	Approved
0.5888	Remote Similarity	NPD4730	Approved
0.5888	Remote Similarity	NPD7320	Approved
0.5888	Remote Similarity	NPD6011	Approved
0.5888	Remote Similarity	NPD4729	Approved
0.5882	Remote Similarity	NPD5290	Discontinued
0.5882	Remote Similarity	NPD5696	Approved
0.5876	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6650	Approved
0.5872	Remote Similarity	NPD6847	Approved
0.5872	Remote Similarity	NPD8130	Phase 1
0.5872	Remote Similarity	NPD6869	Approved
0.5872	Remote Similarity	NPD6649	Approved
0.5872	Remote Similarity	NPD6617	Approved
0.5865	Remote Similarity	NPD5091	Approved
0.5849	Remote Similarity	NPD4768	Approved
0.5849	Remote Similarity	NPD4767	Approved
0.5841	Remote Similarity	NPD7328	Approved
0.5841	Remote Similarity	NPD7327	Approved
0.5833	Remote Similarity	NPD6372	Approved
0.5833	Remote Similarity	NPD6013	Approved
0.5833	Remote Similarity	NPD6012	Approved
0.5833	Remote Similarity	NPD6014	Approved
0.5833	Remote Similarity	NPD6373	Approved
0.5826	Remote Similarity	NPD8033	Approved
0.5818	Remote Similarity	NPD6882	Approved
0.5818	Remote Similarity	NPD8297	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