NPASS Compound

Structure

CID192209 OpenBabel06191715572D 21 24 0 0 0 0 0 0 0 0999 V2000 0.9692 2.9064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4836 3.7455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 -1.0045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1955 0.4852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5179 1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1953 1.4544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5177 0.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3568 0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6786 1.9379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3564 1.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6782 -0.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 2.9066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5174 0.4849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8391 1.4534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5172 1.4541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8389 0.4842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0004 1.9380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8392 0.4845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6783 1.9383 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 21 1 0 0 0 0 4 6 1 0 0 0 0 4 8 2 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 11 1 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 10 15 1 0 0 0 0 11 16 2 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 19 2 0 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 20 2 0 0 0 0 16 21 1 0 0 0 0 17 18 2 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	274.15
Volume:	303.856
LogP:	5.355
LogD:	4.63
LogS:	-6.596
# Rotatable Bonds:	1
TPSA:	17.82
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.48
Synthetic Accessibility Score:	2.252
Fsp3:	0.211
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:	-4.843
MDCK Permeability:	2.075487282127142e-05
Pgp-inhibitor:	0.76
Pgp-substrate:	0.053
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.864
Plasma Protein Binding (PPB):	97.89261627197266%
Volume Distribution (VD):	1.198
Pgp-substrate:	1.2452138662338257%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.871
CYP2C19-inhibitor:	0.592
CYP2C19-substrate:	0.57
CYP2C9-inhibitor:	0.585
CYP2C9-substrate:	0.816
CYP2D6-inhibitor:	0.355
CYP2D6-substrate:	0.869
CYP3A4-inhibitor:	0.476
CYP3A4-substrate:	0.229

ADMET: Excretion

Clearance (CL):	4.093
Half-life (T1/2):	0.06

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.246
Drug-inuced Liver Injury (DILI):	0.748
AMES Toxicity:	0.875
Rat Oral Acute Toxicity:	0.295
Maximum Recommended Daily Dose:	0.389
Skin Sensitization:	0.079
Carcinogencity:	0.765
Eye Corrosion:	0.004
Eye Irritation:	0.95
Respiratory Toxicity:	0.219

Download Data

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

Natural Product: NPC192209

Natural Product ID:	NPC192209
*Common Name:**	5-Methyl-11-Propan-2-Ylindolo[3,2-B]Quinoline
IUPAC Name:	5-methyl-11-propan-2-ylindolo[3,2-b]quinoline
Synonyms:
Standard InCHIKey:	SJPBNUIPWOHEAC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18N2/c1-12(2)17-14-9-5-7-11-16(14)21(3)19-13-8-4-6-10-15(13)20-18(17)19/h4-12H,1-3H3
SMILES:	CC(C)c1c2ccccc2n(C)c2-c1nc1ccccc21
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL172137
PubChem CID:	10731055
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000061] Indoloquinolines

*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
NPO20237	Poecillastra wondoensis	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640526]
NPO20237	Poecillastra wondoensis	Species	Vulcanellidae	Eukaryota	n.a.	depth of 25 m off the shore of Keomun Island, Korea	2004-AUG	PMID[18407691]
NPO20912	Wisteria brachybotrys	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2853205]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32998509]
NPO24783	Erysimum diffusum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11155	Ambrosia maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11155	Ambrosia maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24783	Erysimum diffusum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11155	Ambrosia maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17131	Yucca periculosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20299	Strongylophora durissima	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18755	Fumaria judaica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21890	Epidendrum moseni	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20169	Alseodaphne perakensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20989	Calea integrifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11155	Ambrosia maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24783	Erysimum diffusum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20912	Wisteria brachybotrys	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20237	Poecillastra wondoensis	Species	Vulcanellidae	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	3
Others	1

Activity Type	# Activity
Cell Line	1
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	23800.0	nM	PMID[536340]
NPT27	Others	Unspecified		IC50	=	6500.0	nM	PMID[536340]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2200.0	nM	PMID[536340]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IS	=	10.6	n.a.	PMID[536340]

☑ 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 NPC192209 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	1045
0.1-0.2	11837
0.2-0.3	17092
0.3-0.4	6992
0.4-0.5	2610
0.5-0.6	1950
0.6-0.7	860
0.7-0.8	254
0.8-0.85	36
0.85-0.9	10
0.9-0.95	3
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9633	High Similarity	NPC296163
0.9279	High Similarity	NPC187036
0.8852	High Similarity	NPC9856
0.8783	High Similarity	NPC288232
0.8632	High Similarity	NPC313449
0.814	Intermediate Similarity	NPC184437
0.8099	Intermediate Similarity	NPC264580
0.8017	Intermediate Similarity	NPC302790
0.7953	Intermediate Similarity	NPC476950
0.7807	Intermediate Similarity	NPC291610
0.7686	Intermediate Similarity	NPC314141
0.7619	Intermediate Similarity	NPC475915
0.7609	Intermediate Similarity	NPC20144
0.7576	Intermediate Similarity	NPC53044
0.7563	Intermediate Similarity	NPC164802
0.7538	Intermediate Similarity	NPC478079
0.752	Intermediate Similarity	NPC81561
0.7518	Intermediate Similarity	NPC471574
0.746	Intermediate Similarity	NPC162689
0.746	Intermediate Similarity	NPC54102
0.744	Intermediate Similarity	NPC148140
0.7385	Intermediate Similarity	NPC122718
0.7376	Intermediate Similarity	NPC469525
0.7376	Intermediate Similarity	NPC469735
0.7372	Intermediate Similarity	NPC314102
0.7372	Intermediate Similarity	NPC251722
0.7357	Intermediate Similarity	NPC136002
0.7353	Intermediate Similarity	NPC198988
0.7353	Intermediate Similarity	NPC325599
0.7324	Intermediate Similarity	NPC469740
0.7313	Intermediate Similarity	NPC22079
0.7266	Intermediate Similarity	NPC88097
0.723	Intermediate Similarity	NPC475990
0.7214	Intermediate Similarity	NPC59084
0.7209	Intermediate Similarity	NPC215519
0.7174	Intermediate Similarity	NPC325252
0.7163	Intermediate Similarity	NPC63157
0.7163	Intermediate Similarity	NPC473868
0.7153	Intermediate Similarity	NPC300299
0.7143	Intermediate Similarity	NPC104483
0.7132	Intermediate Similarity	NPC475450
0.7123	Intermediate Similarity	NPC117032
0.7122	Intermediate Similarity	NPC150259
0.7095	Intermediate Similarity	NPC51054
0.7092	Intermediate Similarity	NPC2949
0.7092	Intermediate Similarity	NPC238499
0.708	Intermediate Similarity	NPC476160
0.7077	Intermediate Similarity	NPC257490
0.7059	Intermediate Similarity	NPC475428
0.7055	Intermediate Similarity	NPC206592
0.7055	Intermediate Similarity	NPC33421
0.7055	Intermediate Similarity	NPC40070
0.705	Intermediate Similarity	NPC218268
0.7049	Intermediate Similarity	NPC79618
0.7034	Intermediate Similarity	NPC21605
0.702	Intermediate Similarity	NPC476231
0.7015	Intermediate Similarity	NPC250361
0.7	Intermediate Similarity	NPC206819
0.7	Intermediate Similarity	NPC318065
0.7	Intermediate Similarity	NPC221786
0.7	Intermediate Similarity	NPC474880
0.6985	Remote Similarity	NPC473587
0.697	Remote Similarity	NPC41174
0.6966	Remote Similarity	NPC478186
0.6959	Remote Similarity	NPC281094
0.6957	Remote Similarity	NPC473930
0.6954	Remote Similarity	NPC229173
0.6953	Remote Similarity	NPC313673
0.695	Remote Similarity	NPC243162
0.694	Remote Similarity	NPC252794
0.6934	Remote Similarity	NPC476689
0.6934	Remote Similarity	NPC476685
0.6934	Remote Similarity	NPC476687
0.693	Remote Similarity	NPC78154
0.6923	Remote Similarity	NPC177684
0.6923	Remote Similarity	NPC291962
0.6918	Remote Similarity	NPC470111
0.6917	Remote Similarity	NPC46358
0.6913	Remote Similarity	NPC476219
0.6912	Remote Similarity	NPC473762
0.6901	Remote Similarity	NPC73767
0.6897	Remote Similarity	NPC470440
0.6889	Remote Similarity	NPC145754
0.6884	Remote Similarity	NPC179365
0.6879	Remote Similarity	NPC125746
0.687	Remote Similarity	NPC258531
0.687	Remote Similarity	NPC112373
0.687	Remote Similarity	NPC161956
0.6863	Remote Similarity	NPC478182
0.6853	Remote Similarity	NPC469783
0.6853	Remote Similarity	NPC284635
0.6853	Remote Similarity	NPC469761
0.6853	Remote Similarity	NPC115611
0.6853	Remote Similarity	NPC469768
0.6853	Remote Similarity	NPC469784
0.6853	Remote Similarity	NPC469779
0.6853	Remote Similarity	NPC469767
0.6853	Remote Similarity	NPC469780
0.6828	Remote Similarity	NPC242556
0.6824	Remote Similarity	NPC53947
0.6822	Remote Similarity	NPC147957
0.6821	Remote Similarity	NPC104345
0.6806	Remote Similarity	NPC277157
0.6806	Remote Similarity	NPC469766
0.6803	Remote Similarity	NPC477134
0.68	Remote Similarity	NPC476297
0.6794	Remote Similarity	NPC226143
0.6783	Remote Similarity	NPC32002
0.6783	Remote Similarity	NPC316811
0.6783	Remote Similarity	NPC110126
0.6783	Remote Similarity	NPC315348
0.6781	Remote Similarity	NPC204141
0.6776	Remote Similarity	NPC56765
0.6776	Remote Similarity	NPC6436
0.6774	Remote Similarity	NPC434
0.6769	Remote Similarity	NPC476566
0.6765	Remote Similarity	NPC476140
0.6761	Remote Similarity	NPC83214
0.6761	Remote Similarity	NPC84911
0.6757	Remote Similarity	NPC37548
0.6753	Remote Similarity	NPC469541
0.6753	Remote Similarity	NPC271797
0.6753	Remote Similarity	NPC21174
0.6742	Remote Similarity	NPC317564
0.6733	Remote Similarity	NPC325903
0.6732	Remote Similarity	NPC255229
0.6732	Remote Similarity	NPC81229
0.6724	Remote Similarity	NPC470926
0.6721	Remote Similarity	NPC178681
0.6718	Remote Similarity	NPC240136
0.6718	Remote Similarity	NPC471402
0.6718	Remote Similarity	NPC297486
0.6716	Remote Similarity	NPC283130
0.6716	Remote Similarity	NPC328683
0.6715	Remote Similarity	NPC150863
0.6713	Remote Similarity	NPC169433
0.6712	Remote Similarity	NPC116519
0.6711	Remote Similarity	NPC286427
0.671	Remote Similarity	NPC2165
0.671	Remote Similarity	NPC195507
0.669	Remote Similarity	NPC261195
0.669	Remote Similarity	NPC96102
0.669	Remote Similarity	NPC29886
0.6689	Remote Similarity	NPC179787
0.6689	Remote Similarity	NPC201380
0.6688	Remote Similarity	NPC194881
0.6688	Remote Similarity	NPC194411
0.6688	Remote Similarity	NPC474897
0.6667	Remote Similarity	NPC41257
0.6667	Remote Similarity	NPC470233
0.6667	Remote Similarity	NPC470550
0.6667	Remote Similarity	NPC312092
0.6667	Remote Similarity	NPC91958
0.6667	Remote Similarity	NPC2823
0.6667	Remote Similarity	NPC293487
0.6667	Remote Similarity	NPC205652
0.6644	Remote Similarity	NPC124005
0.6644	Remote Similarity	NPC187951
0.6644	Remote Similarity	NPC321911
0.6643	Remote Similarity	NPC105127
0.6642	Remote Similarity	NPC469949
0.6642	Remote Similarity	NPC182570
0.6642	Remote Similarity	NPC48564
0.6642	Remote Similarity	NPC265605
0.6638	Remote Similarity	NPC191444
0.6623	Remote Similarity	NPC200743
0.6622	Remote Similarity	NPC288838
0.6622	Remote Similarity	NPC254798
0.6622	Remote Similarity	NPC63545
0.6622	Remote Similarity	NPC143872
0.6618	Remote Similarity	NPC476322
0.6615	Remote Similarity	NPC143156
0.6601	Remote Similarity	NPC299594
0.6601	Remote Similarity	NPC216643
0.6597	Remote Similarity	NPC130251
0.6596	Remote Similarity	NPC313352
0.6584	Remote Similarity	NPC326575
0.6584	Remote Similarity	NPC28848
0.6584	Remote Similarity	NPC14325
0.6582	Remote Similarity	NPC65080
0.6579	Remote Similarity	NPC38736
0.6579	Remote Similarity	NPC470507
0.6577	Remote Similarity	NPC469811
0.6571	Remote Similarity	NPC69914
0.6562	Remote Similarity	NPC37423
0.6562	Remote Similarity	NPC275305
0.6561	Remote Similarity	NPC478183
0.6554	Remote Similarity	NPC314372
0.6552	Remote Similarity	NPC301760
0.6552	Remote Similarity	NPC22082
0.6552	Remote Similarity	NPC186284
0.6552	Remote Similarity	NPC176858
0.6547	Remote Similarity	NPC314431
0.6547	Remote Similarity	NPC473417
0.6547	Remote Similarity	NPC280807
0.6547	Remote Similarity	NPC472245
0.6544	Remote Similarity	NPC290094
0.6538	Remote Similarity	NPC478184
0.6536	Remote Similarity	NPC285469
0.6533	Remote Similarity	NPC2272

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 NPC192209 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	487
0.1-0.2	837
0.2-0.3	892
0.3-0.4	2034
0.4-0.5	2306
0.5-0.6	1814
0.6-0.7	664
0.7-0.8	104
0.8-0.85	10
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8632	High Similarity	NPD7481	Approved
0.8632	High Similarity	NPD7480	Approved
0.8571	High Similarity	NPD6299	Approved
0.8571	High Similarity	NPD6300	Approved
0.8226	Intermediate Similarity	NPD4985	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD2840	Approved
0.8158	Intermediate Similarity	NPD993	Approved
0.8158	Intermediate Similarity	NPD990	Approved
0.8087	Intermediate Similarity	NPD4115	Approved
0.8087	Intermediate Similarity	NPD4114	Approved
0.8	Intermediate Similarity	NPD3545	Approved
0.8	Intermediate Similarity	NPD3546	Approved
0.7983	Intermediate Similarity	NPD2914	Approved
0.7983	Intermediate Similarity	NPD2913	Approved
0.7949	Intermediate Similarity	NPD4116	Approved
0.7937	Intermediate Similarity	NPD1937	Approved
0.7934	Intermediate Similarity	NPD2467	Approved
0.7934	Intermediate Similarity	NPD2464	Approved
0.7934	Intermediate Similarity	NPD2463	Approved
0.7807	Intermediate Similarity	NPD4735	Approved
0.7807	Intermediate Similarity	NPD4734	Approved
0.7769	Intermediate Similarity	NPD5631	Phase 3
0.768	Intermediate Similarity	NPD2340	Discontinued
0.7669	Intermediate Similarity	NPD3385	Approved
0.7667	Intermediate Similarity	NPD3001	Approved
0.7667	Intermediate Similarity	NPD2999	Approved
0.7664	Intermediate Similarity	NPD6301	Phase 2
0.7647	Intermediate Similarity	NPD7633	Discontinued
0.7627	Intermediate Similarity	NPD5253	Approved
0.7623	Intermediate Similarity	NPD5629	Discontinued
0.7563	Intermediate Similarity	NPD1721	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD477	Phase 1
0.7521	Intermediate Similarity	NPD2038	Approved
0.7521	Intermediate Similarity	NPD2039	Approved
0.75	Intermediate Similarity	NPD3654	Approved
0.7482	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD4047	Discontinued
0.7385	Intermediate Similarity	NPD2143	Discontinued
0.7372	Intermediate Similarity	NPD45	Approved
0.7372	Intermediate Similarity	NPD6554	Approved
0.736	Intermediate Similarity	NPD6069	Approved
0.736	Intermediate Similarity	NPD6070	Approved
0.7353	Intermediate Similarity	NPD1883	Approved
0.7348	Intermediate Similarity	NPD2119	Approved
0.7348	Intermediate Similarity	NPD2118	Approved
0.7319	Intermediate Similarity	NPD3276	Approved
0.7293	Intermediate Similarity	NPD4019	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD4451	Approved
0.7266	Intermediate Similarity	NPD4450	Approved
0.7258	Intermediate Similarity	NPD5179	Approved
0.7258	Intermediate Similarity	NPD5180	Approved
0.7258	Intermediate Similarity	NPD5181	Approved
0.7244	Intermediate Similarity	NPD5657	Phase 3
0.7234	Intermediate Similarity	NPD6506	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7461	Approved
0.7226	Intermediate Similarity	NPD2292	Approved
0.7226	Intermediate Similarity	NPD1998	Approved
0.7214	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD3548	Approved
0.7206	Intermediate Similarity	NPD7200	Approved
0.7203	Intermediate Similarity	NPD1683	Approved
0.7197	Intermediate Similarity	NPD6900	Discontinued
0.7194	Intermediate Similarity	NPD1864	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1870	Approved
0.7194	Intermediate Similarity	NPD1866	Approved
0.7188	Intermediate Similarity	NPD3498	Approved
0.7188	Intermediate Similarity	NPD2212	Approved
0.7188	Intermediate Similarity	NPD3499	Approved
0.7188	Intermediate Similarity	NPD2210	Approved
0.7185	Intermediate Similarity	NPD3476	Approved
0.7185	Intermediate Similarity	NPD3475	Approved
0.7185	Intermediate Similarity	NPD6820	Approved
0.7185	Intermediate Similarity	NPD6822	Approved
0.7176	Intermediate Similarity	NPD2938	Approved
0.7176	Intermediate Similarity	NPD2940	Approved
0.7174	Intermediate Similarity	NPD1255	Approved
0.7174	Intermediate Similarity	NPD4411	Phase 1
0.7174	Intermediate Similarity	NPD1253	Approved
0.7174	Intermediate Similarity	NPD1254	Approved
0.7174	Intermediate Similarity	NPD4410	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3864	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1256	Approved
0.7168	Intermediate Similarity	NPD3000	Approved
0.7168	Intermediate Similarity	NPD2997	Approved
0.7168	Intermediate Similarity	NPD2998	Approved
0.7163	Intermediate Similarity	NPD5526	Phase 2
0.7163	Intermediate Similarity	NPD5527	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4029	Approved
0.7153	Intermediate Similarity	NPD4030	Approved
0.7153	Intermediate Similarity	NPD4028	Approved
0.7143	Intermediate Similarity	NPD1720	Phase 2
0.7143	Intermediate Similarity	NPD1723	Phase 2
0.7143	Intermediate Similarity	NPD6285	Phase 2
0.7143	Intermediate Similarity	NPD2244	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5839	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD2679	Approved
0.7131	Intermediate Similarity	NPD2678	Approved
0.7123	Intermediate Similarity	NPD3248	Phase 1
0.7122	Intermediate Similarity	NPD2733	Approved
0.7111	Intermediate Similarity	NPD4866	Approved
0.7111	Intermediate Similarity	NPD4300	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4867	Approved
0.7111	Intermediate Similarity	NPD3841	Phase 3
0.7109	Intermediate Similarity	NPD1668	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3623	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3622	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1728	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2304	Approved
0.7071	Intermediate Similarity	NPD6606	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD1950	Approved
0.7068	Intermediate Similarity	NPD1949	Approved
0.7063	Intermediate Similarity	NPD4509	Discontinued
0.7063	Intermediate Similarity	NPD5254	Discontinued
0.7063	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1417	Approved
0.7059	Intermediate Similarity	NPD1419	Approved
0.7055	Intermediate Similarity	NPD8355	Approved
0.7055	Intermediate Similarity	NPD6575	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD8353	Approved
0.7029	Intermediate Similarity	NPD3942	Approved
0.7029	Intermediate Similarity	NPD3944	Approved
0.7029	Intermediate Similarity	NPD6821	Approved
0.7021	Intermediate Similarity	NPD1904	Approved
0.7021	Intermediate Similarity	NPD1902	Approved
0.7007	Intermediate Similarity	NPD2882	Phase 1
0.7007	Intermediate Similarity	NPD1251	Discontinued
0.6993	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3100	Discontinued
0.6986	Remote Similarity	NPD5538	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1001	Discontinued
0.6985	Remote Similarity	NPD947	Approved
0.6984	Remote Similarity	NPD3147	Approved
0.6984	Remote Similarity	NPD3150	Approved
0.6984	Remote Similarity	NPD3149	Approved
0.6984	Remote Similarity	NPD2658	Approved
0.6984	Remote Similarity	NPD3148	Approved
0.6984	Remote Similarity	NPD2659	Approved
0.698	Remote Similarity	NPD7091	Discontinued
0.6967	Remote Similarity	NPD1064	Approved
0.6967	Remote Similarity	NPD1065	Approved
0.6959	Remote Similarity	NPD8354	Approved
0.6953	Remote Similarity	NPD6660	Discontinued
0.6935	Remote Similarity	NPD1108	Approved
0.6935	Remote Similarity	NPD1107	Approved
0.6935	Remote Similarity	NPD1539	Approved
0.6918	Remote Similarity	NPD4547	Phase 3
0.6911	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1762	Approved
0.6905	Remote Similarity	NPD1764	Approved
0.6897	Remote Similarity	NPD6549	Approved
0.6897	Remote Similarity	NPD6548	Approved
0.6894	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6707	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD1316	Discontinued
0.6875	Remote Similarity	NPD2866	Approved
0.6875	Remote Similarity	NPD2622	Approved
0.6849	Remote Similarity	NPD1886	Approved
0.6849	Remote Similarity	NPD7469	Discontinued
0.6847	Remote Similarity	NPD2539	Approved
0.6847	Remote Similarity	NPD2538	Approved
0.6842	Remote Similarity	NPD5787	Discontinued
0.6842	Remote Similarity	NPD5656	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1561	Phase 2
0.6838	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2915	Discontinued
0.6812	Remote Similarity	NPD715	Phase 3
0.6812	Remote Similarity	NPD1920	Approved
0.6812	Remote Similarity	NPD1919	Approved
0.6806	Remote Similarity	NPD1722	Approved
0.6794	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3424	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD2075	Approved
0.6783	Remote Similarity	NPD786	Approved
0.6783	Remote Similarity	NPD2071	Approved
0.6783	Remote Similarity	NPD2073	Approved
0.6783	Remote Similarity	NPD2070	Approved
0.6783	Remote Similarity	NPD2069	Approved
0.6783	Remote Similarity	NPD2068	Approved
0.6783	Remote Similarity	NPD2074	Approved
0.6783	Remote Similarity	NPD1953	Discontinued
0.6783	Remote Similarity	NPD2072	Approved
0.6779	Remote Similarity	NPD3306	Approved
0.6759	Remote Similarity	NPD2006	Phase 2
0.6742	Remote Similarity	NPD6892	Discontinued
0.6742	Remote Similarity	NPD1525	Approved
0.6739	Remote Similarity	NPD5782	Phase 3
0.6739	Remote Similarity	NPD4857	Phase 1
0.6739	Remote Similarity	NPD6489	Phase 3
0.6738	Remote Similarity	NPD2867	Approved
0.6731	Remote Similarity	NPD4639	Approved
0.6731	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4638	Approved
0.6731	Remote Similarity	NPD4640	Approved
0.6726	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD23	Approved
0.6718	Remote Similarity	NPD1903	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