NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	229.07
Volume:	229.284
LogP:	3.121
LogD:	3.123
LogS:	-4.04
# Rotatable Bonds:	2
TPSA:	44.49
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.677
Synthetic Accessibility Score:	2.337
Fsp3:	0.154
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.745
MDCK Permeability:	2.8761009161826223e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.427
Plasma Protein Binding (PPB):	90.05899047851562%
Volume Distribution (VD):	0.493
Pgp-substrate:	6.2070136070251465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.906
CYP2C19-substrate:	0.51
CYP2C9-inhibitor:	0.571
CYP2C9-substrate:	0.893
CYP2D6-inhibitor:	0.776
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.867
CYP3A4-substrate:	0.349

ADMET: Excretion

Clearance (CL):	9.397
Half-life (T1/2):	0.34

ADMET: Toxicity

hERG Blockers:	0.136
Human Hepatotoxicity (H-HT):	0.391
Drug-inuced Liver Injury (DILI):	0.928
AMES Toxicity:	0.778
Rat Oral Acute Toxicity:	0.496
Maximum Recommended Daily Dose:	0.387
Skin Sensitization:	0.367
Carcinogencity:	0.734
Eye Corrosion:	0.003
Eye Irritation:	0.138
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC16066

Natural Product ID:	NPC16066
*Common Name:**	Pteleine
IUPAC Name:	4,6-dimethoxyfuro[2,3-b]quinoline
Synonyms:	Pteleine
Standard InCHIKey:	ALLQMEDAYDKMIO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H11NO3/c1-15-8-3-4-11-10(7-8)12(16-2)9-5-6-17-13(9)14-11/h3-7H,1-2H3
SMILES:	COc1ccc2c(c1)c(c1ccoc1n2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486165
PubChem CID:	159650
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
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	roots	northern Saudi desert	n.a.	PMID[10924184]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12568545]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19191562]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	Whole Plants	n.a.	n.a.	PMID[28093914]
NPO10385	Ptelea trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10385	Ptelea trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10385	Ptelea trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24476	Phellodendron amurense	Species	Rutaceae	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]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26538	Phellodendron chinese	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10385	Ptelea trifoliata	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
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	50.0	ug.mL-1	PMID[456376]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	50.0	ug.mL-1	PMID[456376]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	50.0	ug.mL-1	PMID[456376]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[456376]

☑ 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 NPC16066 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	560
0.1-0.2	3547
0.2-0.3	12873
0.3-0.4	3855
0.4-0.5	12831
0.5-0.6	7442
0.6-0.7	1321
0.7-0.8	239
0.8-0.85	15
0.85-0.9	6
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9789	High Similarity	NPC269367
0.9394	High Similarity	NPC298436
0.9343	High Similarity	NPC131885
0.922	High Similarity	NPC217176
0.9167	High Similarity	NPC140296
0.9163	High Similarity	NPC97746
0.9113	High Similarity	NPC205372
0.8915	High Similarity	NPC168922
0.8791	High Similarity	NPC188400
0.867	High Similarity	NPC1608
0.8638	High Similarity	NPC34770
0.8402	Intermediate Similarity	NPC166712
0.8378	Intermediate Similarity	NPC173250
0.8364	Intermediate Similarity	NPC208364
0.8364	Intermediate Similarity	NPC160100
0.8341	Intermediate Similarity	NPC203373
0.8288	Intermediate Similarity	NPC58209
0.8158	Intermediate Similarity	NPC120513
0.8152	Intermediate Similarity	NPC46561
0.8146	Intermediate Similarity	NPC45190
0.7915	Intermediate Similarity	NPC310211
0.7915	Intermediate Similarity	NPC308137
0.7889	Intermediate Similarity	NPC66083
0.7885	Intermediate Similarity	NPC300156
0.787	Intermediate Similarity	NPC198503
0.7857	Intermediate Similarity	NPC101312
0.7847	Intermediate Similarity	NPC249583
0.7812	Intermediate Similarity	NPC6786
0.7811	Intermediate Similarity	NPC45389
0.7783	Intermediate Similarity	NPC187501
0.7767	Intermediate Similarity	NPC280714
0.7757	Intermediate Similarity	NPC116238
0.775	Intermediate Similarity	NPC194040
0.7731	Intermediate Similarity	NPC247803
0.7717	Intermediate Similarity	NPC314633
0.7696	Intermediate Similarity	NPC208084
0.7685	Intermediate Similarity	NPC169402
0.7664	Intermediate Similarity	NPC472098
0.7661	Intermediate Similarity	NPC150239
0.7633	Intermediate Similarity	NPC112937
0.7626	Intermediate Similarity	NPC280799
0.7619	Intermediate Similarity	NPC41216
0.761	Intermediate Similarity	NPC79293
0.761	Intermediate Similarity	NPC279401
0.7605	Intermediate Similarity	NPC230683
0.7594	Intermediate Similarity	NPC4687
0.7594	Intermediate Similarity	NPC321428
0.758	Intermediate Similarity	NPC174760
0.7576	Intermediate Similarity	NPC283152
0.7546	Intermediate Similarity	NPC39500
0.7535	Intermediate Similarity	NPC146418
0.7523	Intermediate Similarity	NPC179287
0.7512	Intermediate Similarity	NPC193238
0.75	Intermediate Similarity	NPC264176
0.75	Intermediate Similarity	NPC225279
0.75	Intermediate Similarity	NPC472099
0.7477	Intermediate Similarity	NPC82548
0.7455	Intermediate Similarity	NPC157931
0.7454	Intermediate Similarity	NPC87413
0.7453	Intermediate Similarity	NPC317572
0.7437	Intermediate Similarity	NPC288943
0.7409	Intermediate Similarity	NPC184408
0.7407	Intermediate Similarity	NPC470020
0.7397	Intermediate Similarity	NPC3207
0.7382	Intermediate Similarity	NPC26872
0.7358	Intermediate Similarity	NPC26850
0.7353	Intermediate Similarity	NPC42591
0.735	Intermediate Similarity	NPC84347
0.7349	Intermediate Similarity	NPC53344
0.7319	Intermediate Similarity	NPC161801
0.7315	Intermediate Similarity	NPC210828
0.7315	Intermediate Similarity	NPC86834
0.7301	Intermediate Similarity	NPC478078
0.73	Intermediate Similarity	NPC303225
0.7297	Intermediate Similarity	NPC288987
0.7294	Intermediate Similarity	NPC9894
0.7294	Intermediate Similarity	NPC23294
0.7294	Intermediate Similarity	NPC294375
0.7294	Intermediate Similarity	NPC220337
0.7281	Intermediate Similarity	NPC474688
0.7277	Intermediate Similarity	NPC144452
0.7273	Intermediate Similarity	NPC477589
0.7273	Intermediate Similarity	NPC477587
0.7269	Intermediate Similarity	NPC270918
0.7265	Intermediate Similarity	NPC469439
0.7261	Intermediate Similarity	NPC253675
0.7261	Intermediate Similarity	NPC39370
0.7253	Intermediate Similarity	NPC119134
0.7249	Intermediate Similarity	NPC473186
0.7248	Intermediate Similarity	NPC303951
0.7244	Intermediate Similarity	NPC322482
0.7235	Intermediate Similarity	NPC39679
0.7231	Intermediate Similarity	NPC185197
0.7229	Intermediate Similarity	NPC473187
0.722	Intermediate Similarity	NPC62069
0.7212	Intermediate Similarity	NPC473449
0.721	Intermediate Similarity	NPC477590
0.721	Intermediate Similarity	NPC477586
0.721	Intermediate Similarity	NPC477588
0.721	Intermediate Similarity	NPC477585
0.7202	Intermediate Similarity	NPC174758
0.7202	Intermediate Similarity	NPC174672
0.7195	Intermediate Similarity	NPC118228
0.7193	Intermediate Similarity	NPC311906
0.7193	Intermediate Similarity	NPC471762
0.719	Intermediate Similarity	NPC230403
0.7189	Intermediate Similarity	NPC283117
0.7188	Intermediate Similarity	NPC323969
0.7181	Intermediate Similarity	NPC470018
0.7175	Intermediate Similarity	NPC96321
0.7174	Intermediate Similarity	NPC196718
0.7174	Intermediate Similarity	NPC102593
0.7171	Intermediate Similarity	NPC176127
0.7169	Intermediate Similarity	NPC471304
0.7162	Intermediate Similarity	NPC148183
0.7162	Intermediate Similarity	NPC152768
0.716	Intermediate Similarity	NPC89549
0.7156	Intermediate Similarity	NPC131017
0.715	Intermediate Similarity	NPC204385
0.7149	Intermediate Similarity	NPC257851
0.7143	Intermediate Similarity	NPC329631
0.713	Intermediate Similarity	NPC162484
0.713	Intermediate Similarity	NPC305984
0.7129	Intermediate Similarity	NPC312872
0.7121	Intermediate Similarity	NPC118511
0.7118	Intermediate Similarity	NPC274640
0.7114	Intermediate Similarity	NPC88923
0.7114	Intermediate Similarity	NPC100734
0.7114	Intermediate Similarity	NPC315634
0.7102	Intermediate Similarity	NPC209981
0.7093	Intermediate Similarity	NPC122436
0.7091	Intermediate Similarity	NPC309845
0.709	Intermediate Similarity	NPC191489
0.7089	Intermediate Similarity	NPC90229
0.7083	Intermediate Similarity	NPC295898
0.708	Intermediate Similarity	NPC60621
0.7078	Intermediate Similarity	NPC287208
0.7072	Intermediate Similarity	NPC74562
0.7072	Intermediate Similarity	NPC151781
0.7072	Intermediate Similarity	NPC316181
0.7071	Intermediate Similarity	NPC177404
0.7067	Intermediate Similarity	NPC160381
0.7064	Intermediate Similarity	NPC472111
0.7049	Intermediate Similarity	NPC284685
0.7048	Intermediate Similarity	NPC144381
0.7043	Intermediate Similarity	NPC194740
0.7043	Intermediate Similarity	NPC66777
0.7042	Intermediate Similarity	NPC134637
0.704	Intermediate Similarity	NPC146976
0.7039	Intermediate Similarity	NPC206201
0.7035	Intermediate Similarity	NPC128115
0.7034	Intermediate Similarity	NPC475844
0.7032	Intermediate Similarity	NPC315545
0.7032	Intermediate Similarity	NPC314297
0.7022	Intermediate Similarity	NPC174576
0.702	Intermediate Similarity	NPC314222
0.702	Intermediate Similarity	NPC196449
0.7014	Intermediate Similarity	NPC469390
0.7014	Intermediate Similarity	NPC219664
0.7012	Intermediate Similarity	NPC67401
0.7009	Intermediate Similarity	NPC274982
0.7	Intermediate Similarity	NPC74575
0.6996	Remote Similarity	NPC236668
0.6992	Remote Similarity	NPC475816
0.6991	Remote Similarity	NPC176538
0.6987	Remote Similarity	NPC72715
0.6986	Remote Similarity	NPC315638
0.6986	Remote Similarity	NPC313796
0.6986	Remote Similarity	NPC314855
0.6986	Remote Similarity	NPC313345
0.6983	Remote Similarity	NPC474701
0.6978	Remote Similarity	NPC293151
0.6972	Remote Similarity	NPC223427
0.6971	Remote Similarity	NPC320394
0.6971	Remote Similarity	NPC165964
0.697	Remote Similarity	NPC246381
0.6964	Remote Similarity	NPC471978
0.6951	Remote Similarity	NPC203168
0.6948	Remote Similarity	NPC470042
0.6948	Remote Similarity	NPC471979
0.6947	Remote Similarity	NPC303658
0.6946	Remote Similarity	NPC78609
0.6943	Remote Similarity	NPC51388
0.6937	Remote Similarity	NPC314834
0.6936	Remote Similarity	NPC470017
0.6933	Remote Similarity	NPC72905
0.6927	Remote Similarity	NPC135887
0.6927	Remote Similarity	NPC199277
0.6926	Remote Similarity	NPC303374
0.6923	Remote Similarity	NPC171787
0.6916	Remote Similarity	NPC74360
0.6913	Remote Similarity	NPC21638
0.691	Remote Similarity	NPC260434
0.6909	Remote Similarity	NPC472286
0.6909	Remote Similarity	NPC472287
0.6907	Remote Similarity	NPC235685
0.6907	Remote Similarity	NPC184680
0.6905	Remote Similarity	NPC61350
0.6904	Remote Similarity	NPC142385
0.6904	Remote Similarity	NPC75179

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 NPC16066 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	717
0.2-0.3	1012
0.3-0.4	1544
0.4-0.5	2864
0.5-0.6	1947
0.6-0.7	606
0.7-0.8	81
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
0.7925	Intermediate Similarity	NPD3257	Approved
0.7867	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3258	Approved
0.7692	Intermediate Similarity	NPD4328	Approved
0.7681	Intermediate Similarity	NPD2778	Approved
0.7674	Intermediate Similarity	NPD5293	Phase 2
0.7639	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD2779	Approved
0.7511	Intermediate Similarity	NPD8102	Discontinued
0.7488	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4952	Phase 3
0.7465	Intermediate Similarity	NPD3507	Phase 2
0.7457	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7454	Intermediate Similarity	NPD5416	Discontinued
0.7444	Intermediate Similarity	NPD3925	Approved
0.7368	Intermediate Similarity	NPD4373	Phase 2
0.7368	Intermediate Similarity	NPD5512	Phase 3
0.7352	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD5488	Discontinued
0.733	Intermediate Similarity	NPD5632	Approved
0.7328	Intermediate Similarity	NPD6790	Phase 1
0.7327	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4418	Discontinued
0.7306	Intermediate Similarity	NPD3945	Discontinued
0.7304	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6974	Phase 3
0.7289	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD1505	Phase 2
0.7277	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD6242	Discontinued
0.7238	Intermediate Similarity	NPD8463	Approved
0.7236	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6716	Phase 1
0.721	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD4204	Approved
0.7206	Intermediate Similarity	NPD4203	Approved
0.7205	Intermediate Similarity	NPD1466	Phase 3
0.7205	Intermediate Similarity	NPD1467	Approved
0.7205	Intermediate Similarity	NPD1867	Approved
0.72	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD5429	Discontinued
0.7186	Intermediate Similarity	NPD2951	Discontinued
0.7175	Intermediate Similarity	NPD7395	Discontinued
0.7162	Intermediate Similarity	NPD5479	Discontinued
0.7162	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4898	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD7853	Phase 2
0.7149	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4369	Phase 2
0.713	Intermediate Similarity	NPD6962	Phase 2
0.713	Intermediate Similarity	NPD5513	Phase 2
0.7117	Intermediate Similarity	NPD4667	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7803	Approved
0.7113	Intermediate Similarity	NPD5482	Discontinued
0.7111	Intermediate Similarity	NPD7180	Phase 3
0.711	Intermediate Similarity	NPD7222	Phase 2
0.7106	Intermediate Similarity	NPD7417	Discontinued
0.7098	Intermediate Similarity	NPD4429	Discontinued
0.7093	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7708	Approved
0.7087	Intermediate Similarity	NPD5022	Discontinued
0.7075	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4558	Phase 2
0.7049	Intermediate Similarity	NPD7956	Approved
0.7049	Intermediate Similarity	NPD7955	Approved
0.704	Intermediate Similarity	NPD4897	Phase 2
0.7027	Intermediate Similarity	NPD7069	Discontinued
0.7026	Intermediate Similarity	NPD7797	Approved
0.7026	Intermediate Similarity	NPD7796	Approved
0.7025	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD3875	Discontinued
0.6974	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6550	Discontinued
0.6955	Remote Similarity	NPD7452	Approved
0.6955	Remote Similarity	NPD7453	Approved
0.6953	Remote Similarity	NPD7031	Phase 1
0.6951	Remote Similarity	NPD6228	Discontinued
0.6951	Remote Similarity	NPD5866	Approved
0.6942	Remote Similarity	NPD3920	Phase 2
0.6941	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5924	Discontinued
0.693	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD3259	Approved
0.6923	Remote Similarity	NPD5658	Approved
0.6923	Remote Similarity	NPD7467	Discontinued
0.6916	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5256	Discontinued
0.6886	Remote Similarity	NPD8479	Phase 2
0.6883	Remote Similarity	NPD3263	Phase 3
0.6883	Remote Similarity	NPD7426	Phase 1
0.688	Remote Similarity	NPD4885	Approved
0.6872	Remote Similarity	NPD3354	Phase 2
0.6867	Remote Similarity	NPD1659	Phase 1
0.6866	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD1483	Discontinued
0.6856	Remote Similarity	NPD5507	Approved
0.6856	Remote Similarity	NPD5506	Approved
0.6852	Remote Similarity	NPD5003	Discontinued
0.6846	Remote Similarity	NPD8100	Phase 3
0.6844	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2884	Phase 1
0.6838	Remote Similarity	NPD5139	Phase 1
0.6838	Remote Similarity	NPD5922	Phase 3
0.6837	Remote Similarity	NPD6251	Discontinued
0.6833	Remote Similarity	NPD3842	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6963	Approved
0.6822	Remote Similarity	NPD6964	Approved
0.682	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8091	Phase 3
0.6795	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD3250	Phase 1
0.6793	Remote Similarity	NPD3006	Discontinued
0.6791	Remote Similarity	NPD1038	Approved
0.6791	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6874	Approved
0.6786	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3392	Approved
0.6774	Remote Similarity	NPD6988	Phase 1
0.6773	Remote Similarity	NPD5450	Discontinued
0.6771	Remote Similarity	NPD3853	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD8101	Phase 3
0.6761	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6590	Discontinued
0.6758	Remote Similarity	NPD1740	Approved
0.6758	Remote Similarity	NPD1739	Approved
0.6757	Remote Similarity	NPD3003	Approved
0.6757	Remote Similarity	NPD5601	Phase 2
0.6757	Remote Similarity	NPD6150	Discontinued
0.6752	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5559	Phase 2
0.6749	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.674	Remote Similarity	NPD1638	Discovery
0.6729	Remote Similarity	NPD2564	Approved
0.6729	Remote Similarity	NPD2565	Phase 2
0.6727	Remote Similarity	NPD6321	Discontinued
0.6712	Remote Similarity	NPD4795	Phase 2
0.6712	Remote Similarity	NPD1768	Approved
0.6711	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.671	Remote Similarity	NPD4923	Phase 1
0.6709	Remote Similarity	NPD7994	Phase 2
0.6696	Remote Similarity	NPD2916	Discontinued
0.6695	Remote Similarity	NPD4368	Phase 2
0.6695	Remote Similarity	NPD5805	Approved
0.6695	Remote Similarity	NPD946	Discontinued
0.6695	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6475	Phase 2
0.6682	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6245	Phase 2
0.668	Remote Similarity	NPD6530	Approved
0.668	Remote Similarity	NPD3328	Phase 2
0.668	Remote Similarity	NPD5532	Phase 2
0.668	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.668	Remote Similarity	NPD6531	Approved
0.6667	Remote Similarity	NPD4506	Discontinued
0.6667	Remote Similarity	NPD5640	Discontinued
0.6667	Remote Similarity	NPD5930	Phase 3
0.6653	Remote Similarity	NPD5469	Phase 3
0.6653	Remote Similarity	NPD4322	Discontinued
0.6653	Remote Similarity	NPD7022	Phase 2
0.6652	Remote Similarity	NPD6568	Discontinued
0.664	Remote Similarity	NPD7859	Phase 2
0.6639	Remote Similarity	NPD7886	Phase 2
0.6639	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7885	Phase 2
0.6639	Remote Similarity	NPD5817	Discontinued
0.6638	Remote Similarity	NPD4845	Discontinued
0.6637	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD3947	Discontinued
0.6636	Remote Similarity	NPD1880	Phase 3
0.6636	Remote Similarity	NPD3825	Phase 3
0.6626	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD3488	Phase 1
0.6622	Remote Similarity	NPD6208	Discontinued
0.6622	Remote Similarity	NPD2510	Approved
0.6622	Remote Similarity	NPD7626	Approved
0.6622	Remote Similarity	NPD2509	Approved
0.6622	Remote Similarity	NPD4154	Approved
0.6622	Remote Similarity	NPD7627	Approved
0.662	Remote Similarity	NPD4889	Approved
0.6619	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD2366	Approved
0.6613	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD8358	Approved
0.661	Remote Similarity	NPD5014	Discontinued
0.6609	Remote Similarity	NPD6209	Approved
0.6609	Remote Similarity	NPD6995	Phase 1
0.6609	Remote Similarity	NPD4989	Phase 2
0.6605	Remote Similarity	NPD2792	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