NPASS Compound

Structure

CID220241 OpenBabel06191716012D 21 23 0 0 0 0 0 0 0 0999 V2000 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 9 2 0 0 0 0 7 10 2 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 15 2 0 0 0 0 14 18 2 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	285.1
Volume:	287.325
LogP:	2.251
LogD:	2.217
LogS:	-3.559
# Rotatable Bonds:	2
TPSA:	60.69
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.735
Synthetic Accessibility Score:	2.21
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.87
MDCK Permeability:	3.1344578019343317e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.445
Plasma Protein Binding (PPB):	91.94647979736328%
Volume Distribution (VD):	0.841
Pgp-substrate:	7.145015716552734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.957
CYP1A2-substrate:	0.974
CYP2C19-inhibitor:	0.607
CYP2C19-substrate:	0.838
CYP2C9-inhibitor:	0.671
CYP2C9-substrate:	0.868
CYP2D6-inhibitor:	0.425
CYP2D6-substrate:	0.86
CYP3A4-inhibitor:	0.383
CYP3A4-substrate:	0.423

ADMET: Excretion

Clearance (CL):	2.793
Half-life (T1/2):	0.441

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.125
Drug-inuced Liver Injury (DILI):	0.22
AMES Toxicity:	0.786
Rat Oral Acute Toxicity:	0.24
Maximum Recommended Daily Dose:	0.282
Skin Sensitization:	0.476
Carcinogencity:	0.883
Eye Corrosion:	0.007
Eye Irritation:	0.813
Respiratory Toxicity:	0.731

Download Data

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

Natural Product: NPC220241

Natural Product ID:	NPC220241
*Common Name:**	Arborinine
IUPAC Name:	1-hydroxy-2,3-dimethoxy-10-methylacridin-9-one
Synonyms:	Arborinine
Standard InCHIKey:	ATBZZQPALSPNMF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H15NO4/c1-17-10-7-5-4-6-9(10)14(18)13-11(17)8-12(20-2)16(21-3)15(13)19/h4-8,19H,1-3H3
SMILES:	COc1cc2c(c(c1OC)O)c(=O)c1c(n2C)cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL349609
PubChem CID:	5281832
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001811] Acridones

*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
NPO25892	Tricleocarpa fragilis	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691711]
NPO6049	Teclea trichocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141852]
NPO26262	Strychnos potatorum	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398531]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12568545]
NPO17936	Glycosmis arborea	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387647]
NPO10019	Ilex oblonga	Species	Aquifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17329884]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19191562]
NPO15090	Zanthoxylum leprieurii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20413315]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	Whole Plants	n.a.	n.a.	PMID[28093914]
NPO4594	Vitellaria paradoxa	Species	Sapotaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4594	Vitellaria paradoxa	Species	Sapotaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26447	Cassia singueana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26557	Daphne tangutica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26557	Daphne tangutica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23886	Pachysandra axillaris	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6049	Teclea trichocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10019	Ilex oblonga	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26400	Boronia anemonifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1833	Erigeron acris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13589	Prunus padus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26317	Cladosporium phlei	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25892	Tricleocarpa fragilis	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25650	Dacrydium fonkii	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17936	Glycosmis arborea	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26557	Daphne tangutica	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15090	Zanthoxylum leprieurii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8736	Bauerella simplicifolia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26262	Strychnos potatorum	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1947	Nemopilema nomurai	Species	Rhizostomatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1568	Allium ramosum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4594	Vitellaria paradoxa	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26447	Cassia singueana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15180	Fusarium sulphureum	Species	Nectriaceae	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	6
Ki	2
Others	10

Activity Type	# Activity
Cell Line	6
Individual Protein	3
NON-MOLECULAR	1
Organism	2
Others	4
SMALL MOLECULE	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1315	Individual Protein	Adenosine A1 receptor	Rattus norvegicus	Ki	=	12700.0	nM	PMID[545010]
NPT1316	Individual Protein	Adenosine A2a receptor	Rattus norvegicus	Ki	=	6470.0	nM	PMID[545010]
NPT218	Individual Protein	Adenosine A3 receptor	Homo sapiens	Displacement	=	63.0	%	PMID[545010]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[545012]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[545012]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	35000.0	nM	PMID[545013]
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	=	74000.0	nM	PMID[545013]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3850.0	nM	PMID[545011]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	9340.0	nM	PMID[545011]
NPT2	Others	Unspecified		Activity	=	2.7	%	PMID[545012]
NPT2	Others	Unspecified		Activity	=	39.6	%	PMID[545012]
NPT2	Others	Unspecified		Activity	=	74.3	%	PMID[545012]
NPT2	Others	Unspecified		Activity	=	95.6	%	PMID[545012]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	56000.0	nM	PMID[545013]
NPT20576	SMALL MOLECULE	Heme	n.a.	Ka	=	3.9	10'4/M	PMID[545014]
NPT20576	SMALL MOLECULE	Heme	n.a.	IC50	=	42000.0	nM	PMID[545014]

☑ 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 NPC220241 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	559
0.1-0.2	3219
0.2-0.3	11688
0.3-0.4	5148
0.4-0.5	7873
0.5-0.6	10751
0.6-0.7	3078
0.7-0.8	308
0.8-0.85	36
0.85-0.9	22
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC295479
0.9689	High Similarity	NPC182853
0.9442	High Similarity	NPC118189
0.9388	High Similarity	NPC134702
0.9343	High Similarity	NPC76478
0.9184	High Similarity	NPC114468
0.9137	High Similarity	NPC2905
0.9137	High Similarity	NPC148391
0.9091	High Similarity	NPC206109
0.9091	High Similarity	NPC114039
0.9086	High Similarity	NPC268223
0.9	High Similarity	NPC195120
0.896	High Similarity	NPC7560
0.8939	High Similarity	NPC116178
0.8905	High Similarity	NPC87560
0.8894	High Similarity	NPC217903
0.8878	High Similarity	NPC212123
0.8818	High Similarity	NPC157983
0.8818	High Similarity	NPC118154
0.88	High Similarity	NPC321166
0.8782	High Similarity	NPC198160
0.8696	High Similarity	NPC285254
0.8673	High Similarity	NPC15987
0.8654	High Similarity	NPC13249
0.8614	High Similarity	NPC30749
0.8592	High Similarity	NPC329830
0.8564	High Similarity	NPC305542
0.8556	High Similarity	NPC298320
0.8542	High Similarity	NPC1820
0.8469	Intermediate Similarity	NPC234933
0.8465	Intermediate Similarity	NPC474366
0.8392	Intermediate Similarity	NPC288759
0.8367	Intermediate Similarity	NPC170333
0.8333	Intermediate Similarity	NPC218303
0.8218	Intermediate Similarity	NPC301292
0.8218	Intermediate Similarity	NPC313112
0.8213	Intermediate Similarity	NPC176113
0.815	Intermediate Similarity	NPC241263
0.8128	Intermediate Similarity	NPC133156
0.7968	Intermediate Similarity	NPC204867
0.7833	Intermediate Similarity	NPC17677
0.7831	Intermediate Similarity	NPC299582
0.7751	Intermediate Similarity	NPC207873
0.7751	Intermediate Similarity	NPC100573
0.7704	Intermediate Similarity	NPC5167
0.7672	Intermediate Similarity	NPC93653
0.7652	Intermediate Similarity	NPC134637
0.7633	Intermediate Similarity	NPC471489
0.7617	Intermediate Similarity	NPC298449
0.7614	Intermediate Similarity	NPC85613
0.7602	Intermediate Similarity	NPC9475
0.7598	Intermediate Similarity	NPC107123
0.7583	Intermediate Similarity	NPC90185
0.7574	Intermediate Similarity	NPC208890
0.7549	Intermediate Similarity	NPC254957
0.7536	Intermediate Similarity	NPC16249
0.7536	Intermediate Similarity	NPC308943
0.7534	Intermediate Similarity	NPC148124
0.7525	Intermediate Similarity	NPC477186
0.7525	Intermediate Similarity	NPC98416
0.7524	Intermediate Similarity	NPC268077
0.7511	Intermediate Similarity	NPC15406
0.75	Intermediate Similarity	NPC476429
0.7489	Intermediate Similarity	NPC99724
0.7489	Intermediate Similarity	NPC128476
0.7488	Intermediate Similarity	NPC71124
0.7487	Intermediate Similarity	NPC327005
0.7476	Intermediate Similarity	NPC41216
0.7465	Intermediate Similarity	NPC477825
0.743	Intermediate Similarity	NPC25961
0.743	Intermediate Similarity	NPC269449
0.7407	Intermediate Similarity	NPC195763
0.7407	Intermediate Similarity	NPC200060
0.7407	Intermediate Similarity	NPC40290
0.7407	Intermediate Similarity	NPC69430
0.7407	Intermediate Similarity	NPC139293
0.7407	Intermediate Similarity	NPC333691
0.7407	Intermediate Similarity	NPC142876
0.7407	Intermediate Similarity	NPC264289
0.7407	Intermediate Similarity	NPC264550
0.7404	Intermediate Similarity	NPC83019
0.7399	Intermediate Similarity	NPC248903
0.7393	Intermediate Similarity	NPC207971
0.7387	Intermediate Similarity	NPC19175
0.738	Intermediate Similarity	NPC476258
0.738	Intermediate Similarity	NPC304837
0.7368	Intermediate Similarity	NPC5374
0.7368	Intermediate Similarity	NPC207239
0.7368	Intermediate Similarity	NPC29231
0.7361	Intermediate Similarity	NPC477827
0.7361	Intermediate Similarity	NPC470481
0.7361	Intermediate Similarity	NPC477826
0.7361	Intermediate Similarity	NPC470482
0.7361	Intermediate Similarity	NPC119722
0.7356	Intermediate Similarity	NPC204580
0.7354	Intermediate Similarity	NPC203747
0.7354	Intermediate Similarity	NPC26928
0.7354	Intermediate Similarity	NPC194653
0.7354	Intermediate Similarity	NPC254702
0.7354	Intermediate Similarity	NPC476436
0.7354	Intermediate Similarity	NPC80710
0.7354	Intermediate Similarity	NPC139364
0.7353	Intermediate Similarity	NPC320088
0.7348	Intermediate Similarity	NPC119134
0.7347	Intermediate Similarity	NPC13916
0.7347	Intermediate Similarity	NPC264850
0.733	Intermediate Similarity	NPC31363
0.7326	Intermediate Similarity	NPC142165
0.7319	Intermediate Similarity	NPC302807
0.7306	Intermediate Similarity	NPC117992
0.7306	Intermediate Similarity	NPC477828
0.7306	Intermediate Similarity	NPC230149
0.7306	Intermediate Similarity	NPC168247
0.7306	Intermediate Similarity	NPC57674
0.7306	Intermediate Similarity	NPC152951
0.7304	Intermediate Similarity	NPC18306
0.7302	Intermediate Similarity	NPC46990
0.7302	Intermediate Similarity	NPC188074
0.7302	Intermediate Similarity	NPC125449
0.7296	Intermediate Similarity	NPC24465
0.7294	Intermediate Similarity	NPC55470
0.7292	Intermediate Similarity	NPC121522
0.7292	Intermediate Similarity	NPC269451
0.7292	Intermediate Similarity	NPC477231
0.7292	Intermediate Similarity	NPC216769
0.7292	Intermediate Similarity	NPC131266
0.7292	Intermediate Similarity	NPC257648
0.7292	Intermediate Similarity	NPC181209
0.7292	Intermediate Similarity	NPC35763
0.7292	Intermediate Similarity	NPC100263
0.7292	Intermediate Similarity	NPC100971
0.7292	Intermediate Similarity	NPC291802
0.7292	Intermediate Similarity	NPC209487
0.7292	Intermediate Similarity	NPC245382
0.729	Intermediate Similarity	NPC222561
0.7285	Intermediate Similarity	NPC469439
0.7284	Intermediate Similarity	NPC188400
0.7281	Intermediate Similarity	NPC10732
0.7277	Intermediate Similarity	NPC472279
0.7273	Intermediate Similarity	NPC83198
0.7273	Intermediate Similarity	NPC204908
0.7273	Intermediate Similarity	NPC24228
0.7273	Intermediate Similarity	NPC82056
0.7273	Intermediate Similarity	NPC254659
0.7273	Intermediate Similarity	NPC287722
0.7264	Intermediate Similarity	NPC283810
0.7263	Intermediate Similarity	NPC272721
0.7263	Intermediate Similarity	NPC287395
0.7263	Intermediate Similarity	NPC196277
0.7263	Intermediate Similarity	NPC43669
0.7263	Intermediate Similarity	NPC183655
0.7255	Intermediate Similarity	NPC33902
0.7255	Intermediate Similarity	NPC276674
0.7254	Intermediate Similarity	NPC33051
0.7254	Intermediate Similarity	NPC124714
0.7254	Intermediate Similarity	NPC206238
0.7254	Intermediate Similarity	NPC227337
0.7254	Intermediate Similarity	NPC292214
0.7254	Intermediate Similarity	NPC271779
0.7254	Intermediate Similarity	NPC49402
0.7254	Intermediate Similarity	NPC70433
0.7254	Intermediate Similarity	NPC273462
0.7254	Intermediate Similarity	NPC167091
0.7254	Intermediate Similarity	NPC88645
0.7254	Intermediate Similarity	NPC469550
0.7249	Intermediate Similarity	NPC291173
0.7249	Intermediate Similarity	NPC144691
0.7249	Intermediate Similarity	NPC12377
0.7246	Intermediate Similarity	NPC226708
0.7246	Intermediate Similarity	NPC77878
0.724	Intermediate Similarity	NPC45291
0.724	Intermediate Similarity	NPC19980
0.724	Intermediate Similarity	NPC256406
0.7238	Intermediate Similarity	NPC23080
0.7238	Intermediate Similarity	NPC193906
0.7234	Intermediate Similarity	NPC207732
0.7231	Intermediate Similarity	NPC299520
0.7231	Intermediate Similarity	NPC99597
0.7231	Intermediate Similarity	NPC210084
0.7231	Intermediate Similarity	NPC129684
0.7227	Intermediate Similarity	NPC126556
0.7225	Intermediate Similarity	NPC102003
0.7225	Intermediate Similarity	NPC92722
0.7222	Intermediate Similarity	NPC120239
0.7219	Intermediate Similarity	NPC301178
0.7219	Intermediate Similarity	NPC284556
0.7219	Intermediate Similarity	NPC312256
0.7216	Intermediate Similarity	NPC2928
0.7216	Intermediate Similarity	NPC39184
0.7216	Intermediate Similarity	NPC256925
0.7211	Intermediate Similarity	NPC77378
0.7209	Intermediate Similarity	NPC478075
0.7207	Intermediate Similarity	NPC10653
0.7207	Intermediate Similarity	NPC318525
0.7205	Intermediate Similarity	NPC160113
0.7205	Intermediate Similarity	NPC476220
0.7202	Intermediate Similarity	NPC219582
0.7202	Intermediate Similarity	NPC260979
0.7202	Intermediate Similarity	NPC180234
0.7202	Intermediate Similarity	NPC236637

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 NPC220241 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	685
0.2-0.3	1091
0.3-0.4	1759
0.4-0.5	2641
0.5-0.6	1960
0.6-0.7	589
0.7-0.8	66
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.934	High Similarity	NPD2899	Discontinued
0.803	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD683	Approved
0.7467	Intermediate Similarity	NPD6625	Approved
0.7467	Intermediate Similarity	NPD1483	Discontinued
0.7465	Intermediate Similarity	NPD3949	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6874	Approved
0.7393	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5071	Phase 2
0.7313	Intermediate Similarity	NPD7922	Phase 1
0.7296	Intermediate Similarity	NPD2821	Approved
0.7277	Intermediate Similarity	NPD3298	Approved
0.7251	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD4846	Phase 2
0.7209	Intermediate Similarity	NPD7263	Phase 2
0.7203	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1934	Approved
0.7189	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7071	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD5005	Approved
0.7183	Intermediate Similarity	NPD5006	Approved
0.7172	Intermediate Similarity	NPD5186	Approved
0.7172	Intermediate Similarity	NPD5183	Approved
0.7162	Intermediate Similarity	NPD5496	Approved
0.7136	Intermediate Similarity	NPD5242	Approved
0.7123	Intermediate Similarity	NPD3297	Approved
0.7077	Intermediate Similarity	NPD2801	Approved
0.7059	Intermediate Similarity	NPD7559	Phase 2
0.7054	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD824	Approved
0.7032	Intermediate Similarity	NPD5860	Discontinued
0.7028	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD8091	Phase 3
0.7024	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3882	Suspended
0.7	Intermediate Similarity	NPD5937	Approved
0.6995	Remote Similarity	NPD4668	Phase 2
0.6995	Remote Similarity	NPD3793	Phase 3
0.6995	Remote Similarity	NPD4420	Approved
0.6992	Remote Similarity	NPD7803	Approved
0.699	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7654	Discontinued
0.6972	Remote Similarity	NPD7584	Approved
0.6957	Remote Similarity	NPD8054	Approved
0.6957	Remote Similarity	NPD8053	Approved
0.6955	Remote Similarity	NPD8461	Discontinued
0.6954	Remote Similarity	NPD5978	Approved
0.6954	Remote Similarity	NPD5977	Approved
0.6948	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6296	Discontinued
0.6892	Remote Similarity	NPD7225	Discontinued
0.6889	Remote Similarity	NPD6198	Phase 1
0.6881	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1511	Approved
0.6867	Remote Similarity	NPD6723	Discontinued
0.6847	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6166	Phase 2
0.6829	Remote Similarity	NPD7708	Approved
0.6825	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5582	Discontinued
0.6812	Remote Similarity	NPD6104	Discontinued
0.6808	Remote Similarity	NPD4539	Phase 1
0.6804	Remote Similarity	NPD1512	Approved
0.6802	Remote Similarity	NPD5914	Approved
0.6802	Remote Similarity	NPD6386	Approved
0.6802	Remote Similarity	NPD6385	Approved
0.68	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.68	Remote Similarity	NPD8149	Discontinued
0.6798	Remote Similarity	NPD7907	Approved
0.6792	Remote Similarity	NPD5488	Discontinued
0.6789	Remote Similarity	NPD7955	Approved
0.6789	Remote Similarity	NPD7956	Approved
0.6787	Remote Similarity	NPD4082	Approved
0.6786	Remote Similarity	NPD3229	Phase 2
0.6784	Remote Similarity	NPD5519	Discontinued
0.678	Remote Similarity	NPD3818	Discontinued
0.6771	Remote Similarity	NPD1945	Phase 1
0.6765	Remote Similarity	NPD2898	Approved
0.6765	Remote Similarity	NPD1220	Phase 1
0.6753	Remote Similarity	NPD7224	Discontinued
0.6753	Remote Similarity	NPD7186	Phase 3
0.6753	Remote Similarity	NPD7223	Discontinued
0.675	Remote Similarity	NPD6788	Approved
0.6748	Remote Similarity	NPD1221	Approved
0.6745	Remote Similarity	NPD2843	Phase 2
0.6745	Remote Similarity	NPD2845	Phase 2
0.6743	Remote Similarity	NPD3452	Approved
0.6743	Remote Similarity	NPD3450	Approved
0.6743	Remote Similarity	NPD2494	Approved
0.6743	Remote Similarity	NPD2493	Approved
0.6738	Remote Similarity	NPD4981	Phase 2
0.6729	Remote Similarity	NPD5610	Approved
0.6728	Remote Similarity	NPD5608	Approved
0.6728	Remote Similarity	NPD5609	Approved
0.6726	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.672	Remote Similarity	NPD1510	Phase 2
0.6717	Remote Similarity	NPD2672	Discontinued
0.6717	Remote Similarity	NPD2366	Approved
0.6716	Remote Similarity	NPD955	Approved
0.6715	Remote Similarity	NPD7074	Phase 3
0.6715	Remote Similarity	NPD7479	Phase 2
0.6713	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD7626	Approved
0.6712	Remote Similarity	NPD7627	Approved
0.6712	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4111	Phase 1
0.6711	Remote Similarity	NPD4665	Approved
0.6709	Remote Similarity	NPD7048	Phase 3
0.6709	Remote Similarity	NPD6962	Phase 2
0.6709	Remote Similarity	NPD8067	Phase 3
0.6698	Remote Similarity	NPD4363	Phase 3
0.6698	Remote Similarity	NPD1898	Discontinued
0.6698	Remote Similarity	NPD4360	Phase 2
0.6696	Remote Similarity	NPD6997	Phase 2
0.6684	Remote Similarity	NPD3639	Approved
0.6684	Remote Similarity	NPD3641	Approved
0.6684	Remote Similarity	NPD1240	Approved
0.6684	Remote Similarity	NPD943	Approved
0.6684	Remote Similarity	NPD3640	Phase 3
0.6682	Remote Similarity	NPD5196	Approved
0.6682	Remote Similarity	NPD5197	Approved
0.6682	Remote Similarity	NPD5194	Approved
0.6681	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD6232	Discontinued
0.6667	Remote Similarity	NPD7278	Phase 2
0.6667	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4361	Phase 2
0.6667	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7279	Phase 2
0.6667	Remote Similarity	NPD4380	Phase 2
0.6667	Remote Similarity	NPD6020	Phase 2
0.6667	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5928	Phase 1
0.6653	Remote Similarity	NPD7886	Phase 2
0.6653	Remote Similarity	NPD4373	Phase 2
0.6653	Remote Similarity	NPD7885	Phase 2
0.6652	Remote Similarity	NPD4583	Approved
0.6652	Remote Similarity	NPD4582	Approved
0.6652	Remote Similarity	NPD5025	Approved
0.6652	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7473	Discontinued
0.665	Remote Similarity	NPD3446	Phase 1
0.6638	Remote Similarity	NPD3925	Approved
0.6637	Remote Similarity	NPD4859	Phase 1
0.6637	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD2490	Approved
0.6636	Remote Similarity	NPD2488	Approved
0.6636	Remote Similarity	NPD3516	Approved
0.6636	Remote Similarity	NPD3515	Approved
0.6635	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7472	Approved
0.6634	Remote Similarity	NPD1913	Phase 1
0.6625	Remote Similarity	NPD7417	Discontinued
0.6623	Remote Similarity	NPD4049	Phase 2
0.662	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD8099	Discontinued
0.6618	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD8252	Approved
0.6618	Remote Similarity	NPD8251	Approved
0.6617	Remote Similarity	NPD5353	Approved
0.6617	Remote Similarity	NPD3817	Phase 2
0.6615	Remote Similarity	NPD1549	Phase 2
0.6614	Remote Similarity	NPD1607	Approved
0.6609	Remote Similarity	NPD3437	Discontinued
0.6609	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4004	Approved
0.6606	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4002	Approved
0.6604	Remote Similarity	NPD3154	Approved
0.6604	Remote Similarity	NPD3153	Approved
0.6603	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7301	Phase 3
0.6592	Remote Similarity	NPD4596	Phase 1
0.6587	Remote Similarity	NPD8156	Discontinued
0.6583	Remote Similarity	NPD3296	Phase 1
0.6582	Remote Similarity	NPD4584	Approved
0.6581	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.658	Remote Similarity	NPD2654	Approved
0.658	Remote Similarity	NPD7805	Phase 3
0.6577	Remote Similarity	NPD4467	Phase 2
0.6577	Remote Similarity	NPD4465	Phase 2
0.6575	Remote Similarity	NPD1880	Phase 3
0.6574	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD8367	Approved
0.6569	Remote Similarity	NPD5494	Approved
0.6562	Remote Similarity	NPD2906	Approved
0.6562	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3472	Approved
0.6562	Remote Similarity	NPD7585	Approved
0.6562	Remote Similarity	NPD4022	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