NPASS Compound

Structure

NPC203373 OpenBabel07101719522D 23 25 0 0 0 0 0 0 0 0999 V2000 2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 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 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 23 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	319.11
Volume:	307.542
LogP:	2.384
LogD:	2.725
LogS:	-2.868
# Rotatable Bonds:	5
TPSA:	72.18
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.715
Synthetic Accessibility Score:	2.869
Fsp3:	0.312
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.751
MDCK Permeability:	2.8534259399748407e-05
Pgp-inhibitor:	0.249
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.061
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	75.68291473388672%
Volume Distribution (VD):	0.491
Pgp-substrate:	20.015464782714844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.575
CYP1A2-substrate:	0.985
CYP2C19-inhibitor:	0.651
CYP2C19-substrate:	0.888
CYP2C9-inhibitor:	0.342
CYP2C9-substrate:	0.865
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.871
CYP3A4-inhibitor:	0.5
CYP3A4-substrate:	0.856

ADMET: Excretion

Clearance (CL):	4.555
Half-life (T1/2):	0.39

ADMET: Toxicity

hERG Blockers:	0.263
Human Hepatotoxicity (H-HT):	0.061
Drug-inuced Liver Injury (DILI):	0.863
AMES Toxicity:	0.261
Rat Oral Acute Toxicity:	0.808
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.568
Carcinogencity:	0.273
Eye Corrosion:	0.003
Eye Irritation:	0.201
Respiratory Toxicity:	0.647

Download Data

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

Natural Product: NPC203373

Natural Product ID:	NPC203373
*Common Name:**	4,5,6,7,8-Pentamethoxyfuroquinoline
IUPAC Name:	4,5,6,7,8-pentamethoxyfuro[2,3-b]quinoline
Synonyms:	4,5,6,7,8-Pentamethoxyfuroquinoline
Standard InCHIKey:	ATNODOVGBPPUGB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H17NO6/c1-18-11-8-6-7-23-16(8)17-10-9(11)12(19-2)14(21-4)15(22-5)13(10)20-3/h6-7H,1-5H3
SMILES:	COc1c(OC)c2nc3occc3c(c2c(c1OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513443
PubChem CID:	10381260
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0002374] Furanoquinolines

*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
NPO29436	Vepris punctata	Species	Rutaceae	Eukaryota	wood	Madagascar rainforest	n.a.	PMID[12713408]
NPO29436	Vepris punctata	Species	Rutaceae	Eukaryota	wood	Madagascar Rainforest	n.a.	PMID[15165160]
NPO29436	Vepris punctata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	3.4	ug.mL-1	PMID[551759]

☑ 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 NPC203373 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	648
0.1-0.2	3885
0.2-0.3	12408
0.3-0.4	5061
0.4-0.5	10298
0.5-0.6	9111
0.6-0.7	1097
0.7-0.8	146
0.8-0.85	26
0.85-0.9	7
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9602	High Similarity	NPC120513
0.9452	High Similarity	NPC34770
0.9372	High Similarity	NPC166712
0.9336	High Similarity	NPC173250
0.9248	High Similarity	NPC58209
0.9159	High Similarity	NPC208364
0.9159	High Similarity	NPC160100
0.9091	High Similarity	NPC140296
0.9054	High Similarity	NPC217176
0.9039	High Similarity	NPC1608
0.8917	High Similarity	NPC101312
0.8826	High Similarity	NPC188400
0.8777	High Similarity	NPC168922
0.8727	High Similarity	NPC131885
0.852	High Similarity	NPC298436
0.8451	Intermediate Similarity	NPC205372
0.8341	Intermediate Similarity	NPC16066
0.8333	Intermediate Similarity	NPC97746
0.8161	Intermediate Similarity	NPC269367
0.8138	Intermediate Similarity	NPC230683
0.8065	Intermediate Similarity	NPC209981
0.8	Intermediate Similarity	NPC219664
0.7968	Intermediate Similarity	NPC470042
0.793	Intermediate Similarity	NPC203168
0.7769	Intermediate Similarity	NPC185197
0.7668	Intermediate Similarity	NPC282346
0.7664	Intermediate Similarity	NPC119134
0.7662	Intermediate Similarity	NPC268223
0.7611	Intermediate Similarity	NPC66815
0.756	Intermediate Similarity	NPC473188
0.7542	Intermediate Similarity	NPC118154
0.7542	Intermediate Similarity	NPC157983
0.7532	Intermediate Similarity	NPC87560
0.7521	Intermediate Similarity	NPC314633
0.7511	Intermediate Similarity	NPC76478
0.751	Intermediate Similarity	NPC318068
0.751	Intermediate Similarity	NPC315634
0.751	Intermediate Similarity	NPC100734
0.751	Intermediate Similarity	NPC88923
0.7458	Intermediate Similarity	NPC195120
0.7451	Intermediate Similarity	NPC129897
0.7437	Intermediate Similarity	NPC118189
0.7426	Intermediate Similarity	NPC208084
0.7404	Intermediate Similarity	NPC148391
0.7384	Intermediate Similarity	NPC46561
0.7381	Intermediate Similarity	NPC134637
0.7362	Intermediate Similarity	NPC114468
0.7355	Intermediate Similarity	NPC13249
0.7354	Intermediate Similarity	NPC89549
0.7354	Intermediate Similarity	NPC191489
0.735	Intermediate Similarity	NPC146418
0.7315	Intermediate Similarity	NPC284685
0.7314	Intermediate Similarity	NPC200888
0.7311	Intermediate Similarity	NPC134702
0.7292	Intermediate Similarity	NPC198503
0.728	Intermediate Similarity	NPC148409
0.7265	Intermediate Similarity	NPC476999
0.7257	Intermediate Similarity	NPC2905
0.724	Intermediate Similarity	NPC49672
0.7238	Intermediate Similarity	NPC182853
0.722	Intermediate Similarity	NPC7560
0.7205	Intermediate Similarity	NPC270515
0.7202	Intermediate Similarity	NPC179287
0.7195	Intermediate Similarity	NPC474688
0.7194	Intermediate Similarity	NPC72715
0.7194	Intermediate Similarity	NPC107123
0.7189	Intermediate Similarity	NPC6786
0.7184	Intermediate Similarity	NPC476997
0.7178	Intermediate Similarity	NPC469439
0.7178	Intermediate Similarity	NPC225279
0.7177	Intermediate Similarity	NPC90875
0.7173	Intermediate Similarity	NPC308137
0.7173	Intermediate Similarity	NPC310211
0.7171	Intermediate Similarity	NPC475844
0.7154	Intermediate Similarity	NPC476996
0.7154	Intermediate Similarity	NPC476998
0.7148	Intermediate Similarity	NPC302807
0.7148	Intermediate Similarity	NPC227824
0.7137	Intermediate Similarity	NPC288987
0.7131	Intermediate Similarity	NPC187501
0.713	Intermediate Similarity	NPC112937
0.7125	Intermediate Similarity	NPC169402
0.7124	Intermediate Similarity	NPC41216
0.7114	Intermediate Similarity	NPC476994
0.7107	Intermediate Similarity	NPC150239
0.7104	Intermediate Similarity	NPC472589
0.7097	Intermediate Similarity	NPC207620
0.7087	Intermediate Similarity	NPC124313
0.7082	Intermediate Similarity	NPC67401
0.7075	Intermediate Similarity	NPC207283
0.7075	Intermediate Similarity	NPC84164
0.7071	Intermediate Similarity	NPC30749
0.7071	Intermediate Similarity	NPC169716
0.7068	Intermediate Similarity	NPC329631
0.7059	Intermediate Similarity	NPC220241
0.7059	Intermediate Similarity	NPC295479
0.7052	Intermediate Similarity	NPC476995
0.7049	Intermediate Similarity	NPC144452
0.7042	Intermediate Similarity	NPC116238
0.7033	Intermediate Similarity	NPC285254
0.7028	Intermediate Similarity	NPC233334
0.7027	Intermediate Similarity	NPC472588
0.7025	Intermediate Similarity	NPC247803
0.702	Intermediate Similarity	NPC94842
0.7008	Intermediate Similarity	NPC124300
0.7	Intermediate Similarity	NPC39500
0.7	Intermediate Similarity	NPC474594
0.6996	Remote Similarity	NPC215837
0.698	Remote Similarity	NPC251071
0.698	Remote Similarity	NPC291609
0.6976	Remote Similarity	NPC274640
0.6972	Remote Similarity	NPC253675
0.6969	Remote Similarity	NPC148889
0.6967	Remote Similarity	NPC174760
0.6962	Remote Similarity	NPC212123
0.6962	Remote Similarity	NPC249583
0.6958	Remote Similarity	NPC305542
0.6957	Remote Similarity	NPC79293
0.6957	Remote Similarity	NPC279401
0.6953	Remote Similarity	NPC280714
0.695	Remote Similarity	NPC183537
0.6949	Remote Similarity	NPC470930
0.6948	Remote Similarity	NPC24019
0.6943	Remote Similarity	NPC132385
0.6926	Remote Similarity	NPC310618
0.692	Remote Similarity	NPC45190
0.6917	Remote Similarity	NPC477589
0.6917	Remote Similarity	NPC218303
0.6917	Remote Similarity	NPC477587
0.6914	Remote Similarity	NPC15406
0.6905	Remote Similarity	NPC39370
0.6901	Remote Similarity	NPC176113
0.6901	Remote Similarity	NPC146976
0.6899	Remote Similarity	NPC161801
0.6898	Remote Similarity	NPC196449
0.6898	Remote Similarity	NPC314222
0.689	Remote Similarity	NPC166722
0.6888	Remote Similarity	NPC116178
0.6888	Remote Similarity	NPC264176
0.6885	Remote Similarity	NPC184408
0.6885	Remote Similarity	NPC77878
0.6885	Remote Similarity	NPC137353
0.6875	Remote Similarity	NPC474366
0.687	Remote Similarity	NPC303374
0.6863	Remote Similarity	NPC304837
0.6863	Remote Similarity	NPC476258
0.6863	Remote Similarity	NPC477585
0.6863	Remote Similarity	NPC477590
0.6863	Remote Similarity	NPC477588
0.6863	Remote Similarity	NPC477586
0.686	Remote Similarity	NPC217903
0.686	Remote Similarity	NPC321166
0.686	Remote Similarity	NPC236668
0.685	Remote Similarity	NPC182907
0.685	Remote Similarity	NPC189903
0.6846	Remote Similarity	NPC165964
0.6842	Remote Similarity	NPC471978
0.6835	Remote Similarity	NPC317572
0.683	Remote Similarity	NPC473833
0.6829	Remote Similarity	NPC54066
0.6828	Remote Similarity	NPC471979
0.6825	Remote Similarity	NPC473186
0.682	Remote Similarity	NPC474595
0.682	Remote Similarity	NPC198160
0.6818	Remote Similarity	NPC38237
0.6815	Remote Similarity	NPC473639
0.6811	Remote Similarity	NPC108342
0.6811	Remote Similarity	NPC473187
0.6809	Remote Similarity	NPC220408
0.6802	Remote Similarity	NPC280799
0.6798	Remote Similarity	NPC172222
0.6787	Remote Similarity	NPC473449
0.6786	Remote Similarity	NPC474701
0.6778	Remote Similarity	NPC304183
0.6777	Remote Similarity	NPC23294
0.6756	Remote Similarity	NPC133609
0.675	Remote Similarity	NPC4687
0.6736	Remote Similarity	NPC303951
0.6735	Remote Similarity	NPC3207
0.6732	Remote Similarity	NPC41501
0.6732	Remote Similarity	NPC22481
0.6731	Remote Similarity	NPC120239
0.6725	Remote Similarity	NPC42591
0.672	Remote Similarity	NPC21638
0.6719	Remote Similarity	NPC184680
0.6717	Remote Similarity	NPC13603
0.6708	Remote Similarity	NPC294375
0.6708	Remote Similarity	NPC300156
0.6707	Remote Similarity	NPC210434
0.6706	Remote Similarity	NPC315914
0.6706	Remote Similarity	NPC246381
0.6706	Remote Similarity	NPC277351
0.6706	Remote Similarity	NPC476220
0.6706	Remote Similarity	NPC160113
0.6696	Remote Similarity	NPC204385
0.6695	Remote Similarity	NPC207971
0.6695	Remote Similarity	NPC234933
0.6694	Remote Similarity	NPC209769
0.6693	Remote Similarity	NPC470785
0.6693	Remote Similarity	NPC470018

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 NPC203373 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	737
0.2-0.3	1322
0.3-0.4	2288
0.4-0.5	2623
0.5-0.6	1423
0.6-0.7	348
0.7-0.8	23
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
0.7733	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD1505	Phase 2
0.7574	Intermediate Similarity	NPD2899	Discontinued
0.751	Intermediate Similarity	NPD7803	Approved
0.7447	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD7708	Approved
0.7315	Intermediate Similarity	NPD7955	Approved
0.7315	Intermediate Similarity	NPD7956	Approved
0.7283	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD6974	Phase 3
0.7211	Intermediate Similarity	NPD6716	Phase 1
0.7154	Intermediate Similarity	NPD4952	Phase 3
0.712	Intermediate Similarity	NPD4846	Phase 2
0.7107	Intermediate Similarity	NPD7180	Phase 3
0.7103	Intermediate Similarity	NPD7417	Discontinued
0.71	Intermediate Similarity	NPD2778	Approved
0.7093	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD5924	Discontinued
0.7085	Intermediate Similarity	NPD4898	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1483	Discontinued
0.7068	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD4373	Phase 2
0.7063	Intermediate Similarity	NPD7886	Phase 2
0.7063	Intermediate Similarity	NPD7885	Phase 2
0.7043	Intermediate Similarity	NPD5482	Discontinued
0.7025	Intermediate Similarity	NPD5632	Approved
0.7009	Intermediate Similarity	NPD2779	Approved
0.7	Intermediate Similarity	NPD6625	Approved
0.6944	Remote Similarity	NPD3006	Discontinued
0.6935	Remote Similarity	NPD4328	Approved
0.6929	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7859	Phase 2
0.692	Remote Similarity	NPD1867	Approved
0.6911	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6963	Approved
0.6905	Remote Similarity	NPD2951	Discontinued
0.6905	Remote Similarity	NPD6964	Approved
0.6902	Remote Similarity	NPD6790	Phase 1
0.6901	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3257	Approved
0.6887	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5022	Discontinued
0.6875	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3945	Discontinued
0.6857	Remote Similarity	NPD3258	Approved
0.6855	Remote Similarity	NPD3925	Approved
0.6853	Remote Similarity	NPD6962	Phase 2
0.6852	Remote Similarity	NPD5922	Phase 3
0.6842	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.683	Remote Similarity	NPD6228	Discontinued
0.6827	Remote Similarity	NPD3263	Phase 3
0.682	Remote Similarity	NPD6745	Discontinued
0.6818	Remote Similarity	NPD8091	Phase 3
0.6815	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5479	Discontinued
0.6811	Remote Similarity	NPD7853	Phase 2
0.6795	Remote Similarity	NPD5488	Discontinued
0.6778	Remote Similarity	NPD3507	Phase 2
0.6777	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5532	Phase 2
0.6752	Remote Similarity	NPD5512	Phase 3
0.6748	Remote Similarity	NPD4429	Discontinued
0.6732	Remote Similarity	NPD6494	Phase 2
0.6729	Remote Similarity	NPD5450	Discontinued
0.6722	Remote Similarity	NPD5658	Approved
0.672	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1466	Phase 3
0.6719	Remote Similarity	NPD1467	Approved
0.6708	Remote Similarity	NPD5416	Discontinued
0.6705	Remote Similarity	NPD8463	Approved
0.6694	Remote Similarity	NPD5930	Phase 3
0.6693	Remote Similarity	NPD7031	Phase 1
0.6693	Remote Similarity	NPD5640	Discontinued
0.6681	Remote Similarity	NPD6550	Discontinued
0.668	Remote Similarity	NPD7395	Discontinued
0.6679	Remote Similarity	NPD8102	Discontinued
0.6667	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5914	Approved
0.6667	Remote Similarity	NPD5857	Phase 3
0.6667	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6104	Discontinued
0.6654	Remote Similarity	NPD5805	Approved
0.6654	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD3328	Phase 2
0.664	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.664	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD4885	Approved
0.6626	Remote Similarity	NPD5903	Approved
0.6626	Remote Similarity	NPD5902	Approved
0.6626	Remote Similarity	NPD5293	Phase 2
0.6615	Remote Similarity	NPD7022	Phase 2
0.6612	Remote Similarity	NPD5866	Approved
0.6612	Remote Similarity	NPD5429	Discontinued
0.6603	Remote Similarity	NPD5817	Discontinued
0.6591	Remote Similarity	NPD3986	Discontinued
0.659	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD4368	Phase 2
0.6588	Remote Similarity	NPD3442	Approved
0.6588	Remote Similarity	NPD3441	Approved
0.6585	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD5005	Approved
0.6583	Remote Similarity	NPD5006	Approved
0.6579	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD3920	Phase 2
0.6571	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.657	Remote Similarity	NPD3217	Phase 2
0.6568	Remote Similarity	NPD4418	Discontinued
0.6561	Remote Similarity	NPD7426	Phase 1
0.6559	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5256	Discontinued
0.6543	Remote Similarity	NPD7222	Phase 2
0.6537	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD8459	Approved
0.6536	Remote Similarity	NPD8460	Approved
0.6535	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD3259	Approved
0.6523	Remote Similarity	NPD8067	Phase 3
0.6523	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.652	Remote Similarity	NPD3875	Discontinued
0.6513	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5459	Phase 2
0.6506	Remote Similarity	NPD8461	Discontinued
0.6506	Remote Similarity	NPD5164	Discontinued
0.6504	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD3842	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD7223	Discontinued
0.6496	Remote Similarity	NPD7224	Discontinued
0.6492	Remote Similarity	NPD1638	Discovery
0.6489	Remote Similarity	NPD6517	Phase 3
0.6488	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD1659	Phase 1
0.6484	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6198	Phase 1
0.6477	Remote Similarity	NPD8359	Phase 2
0.6473	Remote Similarity	NPD6321	Discontinued
0.6463	Remote Similarity	NPD3392	Approved
0.6462	Remote Similarity	NPD7048	Phase 3
0.646	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD2884	Phase 1
0.6452	Remote Similarity	NPD8465	Approved
0.6452	Remote Similarity	NPD8467	Approved
0.6452	Remote Similarity	NPD8466	Approved
0.6447	Remote Similarity	NPD6456	Discontinued
0.6444	Remote Similarity	NPD1955	Discontinued
0.6437	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD683	Approved
0.6434	Remote Similarity	NPD3003	Approved
0.6429	Remote Similarity	NPD4369	Phase 2
0.6426	Remote Similarity	NPD7559	Phase 2
0.6417	Remote Similarity	NPD4420	Approved
0.6417	Remote Similarity	NPD7278	Phase 2
0.6417	Remote Similarity	NPD7279	Phase 2
0.6412	Remote Similarity	NPD4613	Phase 2
0.6411	Remote Similarity	NPD3815	Phase 1
0.6411	Remote Similarity	NPD3816	Phase 1
0.6411	Remote Similarity	NPD7069	Discontinued
0.6409	Remote Similarity	NPD7558	Phase 2
0.6408	Remote Similarity	NPD7453	Approved
0.6408	Remote Similarity	NPD7452	Approved
0.6406	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6244	Phase 3
0.6404	Remote Similarity	NPD6243	Phase 3
0.6397	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD6531	Approved
0.6397	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD6530	Approved
0.6382	Remote Similarity	NPD7467	Discontinued
0.6375	Remote Similarity	NPD6719	Approved
0.6374	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6242	Discontinued
0.6364	Remote Similarity	NPD4876	Phase 3
0.6364	Remote Similarity	NPD4875	Phase 3
0.636	Remote Similarity	NPD8426	Approved
0.636	Remote Similarity	NPD3250	Phase 1
0.636	Remote Similarity	NPD8425	Approved
0.6356	Remote Similarity	NPD1898	Discontinued
0.6354	Remote Similarity	NPD8364	Approved
0.6354	Remote Similarity	NPD8363	Approved
0.6353	Remote Similarity	NPD8100	Phase 3
0.6349	Remote Similarity	NPD1926	Approved
0.6345	Remote Similarity	NPD3923	Approved
0.6345	Remote Similarity	NPD3921	Approved
0.6345	Remote Similarity	NPD3924	Approved
0.6345	Remote Similarity	NPD3922	Approved
0.6343	Remote Similarity	NPD7588	Discontinued
0.6342	Remote Similarity	NPD8357	Approved
0.6339	Remote Similarity	NPD7907	Approved
0.6339	Remote Similarity	NPD4923	Phase 1
0.6335	Remote Similarity	NPD8427	Approved
0.6335	Remote Similarity	NPD8428	Approved
0.6335	Remote Similarity	NPD8429	Approved
0.6331	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD2564	Approved
0.6329	Remote Similarity	NPD2565	Phase 2

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