NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	173.08
Volume:	188.304
LogP:	2.195
LogD:	2.384
LogS:	-1.782
# Rotatable Bonds:	1
TPSA:	22.12
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.661
Synthetic Accessibility Score:	1.661
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.599
MDCK Permeability:	2.665843567228876e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.325
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.077

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.96
Plasma Protein Binding (PPB):	93.95344543457031%
Volume Distribution (VD):	0.623
Pgp-substrate:	5.004806995391846%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.736
CYP2C19-substrate:	0.842
CYP2C9-inhibitor:	0.148
CYP2C9-substrate:	0.783
CYP2D6-inhibitor:	0.364
CYP2D6-substrate:	0.906
CYP3A4-inhibitor:	0.275
CYP3A4-substrate:	0.519

ADMET: Excretion

Clearance (CL):	7.599
Half-life (T1/2):	0.651

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.094
Drug-inuced Liver Injury (DILI):	0.631
AMES Toxicity:	0.774
Rat Oral Acute Toxicity:	0.171
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.285
Carcinogencity:	0.897
Eye Corrosion:	0.135
Eye Irritation:	0.943
Respiratory Toxicity:	0.684

Download Data

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

Natural Product: NPC118511

Natural Product ID:	NPC118511
*Common Name:**	8-Methoxy-2-Methylquinoline
IUPAC Name:	8-methoxy-2-methylquinoline
Synonyms:
Standard InCHIKey:	OQXVXPBDSJQYRR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H11NO/c1-8-6-7-9-4-3-5-10(13-2)11(9)12-8/h3-7H,1-2H3
SMILES:	Cc1ccc2cccc(c2n1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2321989
PubChem CID:	316986
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO7170	Tylophora ovata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7170	Tylophora ovata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	2
Others	2

Activity Type	# Activity
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	Activity	=	27.15	%	PMID[512113]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	37.92	%	PMID[512113]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50.0	ug.mL-1	PMID[512114]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	50.0	ug.mL-1	PMID[512114]

☑ 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 NPC118511 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	674
0.1-0.2	5349
0.2-0.3	12054
0.3-0.4	6420
0.4-0.5	13277
0.5-0.6	3449
0.6-0.7	1190
0.7-0.8	263
0.8-0.85	14
0.85-0.9	5
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9085	High Similarity	NPC42591
0.902	High Similarity	NPC26872
0.8846	High Similarity	NPC26850
0.8698	High Similarity	NPC242928
0.8675	High Similarity	NPC474798
0.8598	High Similarity	NPC312872
0.8447	Intermediate Similarity	NPC177404
0.8303	Intermediate Similarity	NPC473764
0.8303	Intermediate Similarity	NPC314940
0.8286	Intermediate Similarity	NPC230403
0.8278	Intermediate Similarity	NPC245816
0.8278	Intermediate Similarity	NPC476138
0.8258	Intermediate Similarity	NPC128823
0.8235	Intermediate Similarity	NPC206201
0.8176	Intermediate Similarity	NPC478032
0.815	Intermediate Similarity	NPC204385
0.8103	Intermediate Similarity	NPC66083
0.8081	Intermediate Similarity	NPC176127
0.8079	Intermediate Similarity	NPC475190
0.8077	Intermediate Similarity	NPC475774
0.8059	Intermediate Similarity	NPC283152
0.8045	Intermediate Similarity	NPC267928
0.8024	Intermediate Similarity	NPC1527
0.8022	Intermediate Similarity	NPC66815
0.8	Intermediate Similarity	NPC288943
0.7962	Intermediate Similarity	NPC60553
0.7931	Intermediate Similarity	NPC62069
0.7929	Intermediate Similarity	NPC252590
0.7917	Intermediate Similarity	NPC44161
0.7912	Intermediate Similarity	NPC19872
0.7907	Intermediate Similarity	NPC472168
0.7861	Intermediate Similarity	NPC222592
0.7861	Intermediate Similarity	NPC185782
0.7861	Intermediate Similarity	NPC168486
0.7861	Intermediate Similarity	NPC473181
0.7829	Intermediate Similarity	NPC84478
0.7819	Intermediate Similarity	NPC199667
0.7816	Intermediate Similarity	NPC118776
0.7789	Intermediate Similarity	NPC476287
0.7778	Intermediate Similarity	NPC187501
0.7772	Intermediate Similarity	NPC470586
0.7753	Intermediate Similarity	NPC296527
0.7742	Intermediate Similarity	NPC470930
0.7737	Intermediate Similarity	NPC26679
0.7737	Intermediate Similarity	NPC473180
0.7737	Intermediate Similarity	NPC94157
0.7709	Intermediate Similarity	NPC76748
0.7701	Intermediate Similarity	NPC304183
0.7696	Intermediate Similarity	NPC39500
0.7667	Intermediate Similarity	NPC92111
0.7647	Intermediate Similarity	NPC264166
0.7647	Intermediate Similarity	NPC274291
0.7647	Intermediate Similarity	NPC47059
0.7647	Intermediate Similarity	NPC329708
0.7647	Intermediate Similarity	NPC165349
0.7647	Intermediate Similarity	NPC118832
0.7637	Intermediate Similarity	NPC131017
0.7632	Intermediate Similarity	NPC219664
0.7629	Intermediate Similarity	NPC174576
0.7622	Intermediate Similarity	NPC315957
0.7622	Intermediate Similarity	NPC176538
0.7622	Intermediate Similarity	NPC329793
0.7619	Intermediate Similarity	NPC287208
0.7617	Intermediate Similarity	NPC8022
0.7617	Intermediate Similarity	NPC470799
0.7611	Intermediate Similarity	NPC144381
0.7604	Intermediate Similarity	NPC162530
0.759	Intermediate Similarity	NPC292958
0.7582	Intermediate Similarity	NPC279401
0.7582	Intermediate Similarity	NPC79293
0.7582	Intermediate Similarity	NPC307963
0.7558	Intermediate Similarity	NPC477888
0.7556	Intermediate Similarity	NPC110741
0.7552	Intermediate Similarity	NPC203168
0.7538	Intermediate Similarity	NPC184408
0.7527	Intermediate Similarity	NPC195268
0.7527	Intermediate Similarity	NPC234197
0.7527	Intermediate Similarity	NPC133140
0.75	Intermediate Similarity	NPC223427
0.75	Intermediate Similarity	NPC473179
0.75	Intermediate Similarity	NPC208084
0.75	Intermediate Similarity	NPC251090
0.7486	Intermediate Similarity	NPC20249
0.7473	Intermediate Similarity	NPC476167
0.7473	Intermediate Similarity	NPC287437
0.747	Intermediate Similarity	NPC153769
0.7469	Intermediate Similarity	NPC470394
0.7469	Intermediate Similarity	NPC470403
0.7469	Intermediate Similarity	NPC470404
0.7462	Intermediate Similarity	NPC132642
0.7462	Intermediate Similarity	NPC225279
0.7459	Intermediate Similarity	NPC230805
0.7449	Intermediate Similarity	NPC131885
0.7444	Intermediate Similarity	NPC314573
0.7444	Intermediate Similarity	NPC61350
0.7433	Intermediate Similarity	NPC329747
0.7432	Intermediate Similarity	NPC114335
0.7432	Intermediate Similarity	NPC280964
0.7432	Intermediate Similarity	NPC141915
0.743	Intermediate Similarity	NPC320394
0.7421	Intermediate Similarity	NPC472111
0.7419	Intermediate Similarity	NPC192315
0.7412	Intermediate Similarity	NPC285635
0.7411	Intermediate Similarity	NPC288987
0.7398	Intermediate Similarity	NPC473513
0.7396	Intermediate Similarity	NPC209769
0.7394	Intermediate Similarity	NPC98685
0.7394	Intermediate Similarity	NPC232727
0.7387	Intermediate Similarity	NPC144452
0.7386	Intermediate Similarity	NPC134586
0.7382	Intermediate Similarity	NPC321428
0.7382	Intermediate Similarity	NPC193238
0.738	Intermediate Similarity	NPC476578
0.738	Intermediate Similarity	NPC4071
0.738	Intermediate Similarity	NPC18487
0.738	Intermediate Similarity	NPC476582
0.7378	Intermediate Similarity	NPC470395
0.7377	Intermediate Similarity	NPC469390
0.7366	Intermediate Similarity	NPC243834
0.7366	Intermediate Similarity	NPC70956
0.7363	Intermediate Similarity	NPC200888
0.736	Intermediate Similarity	NPC173080
0.7356	Intermediate Similarity	NPC476518
0.7354	Intermediate Similarity	NPC135887
0.7354	Intermediate Similarity	NPC199277
0.7345	Intermediate Similarity	NPC211997
0.7344	Intermediate Similarity	NPC82548
0.734	Intermediate Similarity	NPC11017
0.7333	Intermediate Similarity	NPC161292
0.7326	Intermediate Similarity	NPC72211
0.7323	Intermediate Similarity	NPC17565
0.732	Intermediate Similarity	NPC146418
0.7318	Intermediate Similarity	NPC266551
0.7318	Intermediate Similarity	NPC161887
0.7318	Intermediate Similarity	NPC219963
0.7316	Intermediate Similarity	NPC162484
0.7314	Intermediate Similarity	NPC121658
0.7314	Intermediate Similarity	NPC14651
0.7312	Intermediate Similarity	NPC70259
0.7306	Intermediate Similarity	NPC469589
0.7303	Intermediate Similarity	NPC88363
0.7288	Intermediate Similarity	NPC224764
0.7288	Intermediate Similarity	NPC194724
0.7287	Intermediate Similarity	NPC280714
0.7277	Intermediate Similarity	NPC285558
0.7277	Intermediate Similarity	NPC36229
0.7277	Intermediate Similarity	NPC16452
0.7277	Intermediate Similarity	NPC137929
0.7277	Intermediate Similarity	NPC476581
0.7277	Intermediate Similarity	NPC164374
0.7273	Intermediate Similarity	NPC111624
0.7268	Intermediate Similarity	NPC471304
0.7268	Intermediate Similarity	NPC469554
0.7268	Intermediate Similarity	NPC101543
0.7264	Intermediate Similarity	NPC65277
0.7258	Intermediate Similarity	NPC43787
0.7258	Intermediate Similarity	NPC205934
0.7253	Intermediate Similarity	NPC194040
0.7249	Intermediate Similarity	NPC477019
0.7241	Intermediate Similarity	NPC473185
0.724	Intermediate Similarity	NPC45190
0.724	Intermediate Similarity	NPC470164
0.724	Intermediate Similarity	NPC323345
0.724	Intermediate Similarity	NPC300156
0.7238	Intermediate Similarity	NPC284678
0.7236	Intermediate Similarity	NPC148409
0.7231	Intermediate Similarity	NPC208284
0.7228	Intermediate Similarity	NPC471593
0.7228	Intermediate Similarity	NPC179287
0.722	Intermediate Similarity	NPC474688
0.7219	Intermediate Similarity	NPC13880
0.7211	Intermediate Similarity	NPC267423
0.7208	Intermediate Similarity	NPC118228
0.7207	Intermediate Similarity	NPC42979
0.7206	Intermediate Similarity	NPC274640
0.7204	Intermediate Similarity	NPC226202
0.7204	Intermediate Similarity	NPC198673
0.7202	Intermediate Similarity	NPC193777
0.72	Intermediate Similarity	NPC148140
0.7194	Intermediate Similarity	NPC472098
0.7192	Intermediate Similarity	NPC470018
0.7191	Intermediate Similarity	NPC473432
0.7191	Intermediate Similarity	NPC84347
0.7186	Intermediate Similarity	NPC257142
0.7181	Intermediate Similarity	NPC224928
0.7179	Intermediate Similarity	NPC470020
0.7178	Intermediate Similarity	NPC205372
0.7173	Intermediate Similarity	NPC295898
0.7172	Intermediate Similarity	NPC288349
0.7165	Intermediate Similarity	NPC470931
0.7165	Intermediate Similarity	NPC477111
0.7165	Intermediate Similarity	NPC475910
0.716	Intermediate Similarity	NPC284348
0.7157	Intermediate Similarity	NPC471080
0.7157	Intermediate Similarity	NPC140296
0.7157	Intermediate Similarity	NPC74575
0.7157	Intermediate Similarity	NPC469592
0.7152	Intermediate Similarity	NPC81561
0.715	Intermediate Similarity	NPC477113
0.7143	Intermediate Similarity	NPC284559

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 NPC118511 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	403
0.1-0.2	779
0.2-0.3	805
0.3-0.4	1255
0.4-0.5	2963
0.5-0.6	2191
0.6-0.7	640
0.7-0.8	111
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8683	High Similarity	NPD5083	Clinical (unspecified phase)
0.8616	High Similarity	NPD112	Approved
0.8616	High Similarity	NPD9705	Discontinued
0.8047	Intermediate Similarity	NPD9690	Approved
0.8034	Intermediate Similarity	NPD6590	Discontinued
0.8012	Intermediate Similarity	NPD3920	Phase 2
0.7989	Intermediate Similarity	NPD6550	Discontinued
0.7989	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD3477	Phase 2
0.7889	Intermediate Similarity	NPD5512	Phase 3
0.7872	Intermediate Similarity	NPD4502	Phase 2
0.7845	Intermediate Similarity	NPD6988	Phase 1
0.7816	Intermediate Similarity	NPD4203	Approved
0.7816	Intermediate Similarity	NPD4204	Approved
0.7754	Intermediate Similarity	NPD5429	Discontinued
0.7746	Intermediate Similarity	NPD6159	Phase 2
0.7735	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7222	Phase 2
0.7654	Intermediate Similarity	NPD408	Approved
0.7647	Intermediate Similarity	NPD31	Approved
0.7647	Intermediate Similarity	NPD4034	Approved
0.7647	Intermediate Similarity	NPD32	Approved
0.7647	Intermediate Similarity	NPD4036	Approved
0.7647	Intermediate Similarity	NPD4035	Approved
0.7647	Intermediate Similarity	NPD4122	Approved
0.7647	Intermediate Similarity	NPD4037	Approved
0.7647	Intermediate Similarity	NPD4039	Approved
0.7647	Intermediate Similarity	NPD4038	Approved
0.7647	Intermediate Similarity	NPD4033	Approved
0.764	Intermediate Similarity	NPD5256	Discontinued
0.7629	Intermediate Similarity	NPD4429	Discontinued
0.7622	Intermediate Similarity	NPD1739	Approved
0.7622	Intermediate Similarity	NPD1740	Approved
0.7602	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1038	Approved
0.7568	Intermediate Similarity	NPD5999	Phase 2
0.7568	Intermediate Similarity	NPD2176	Approved
0.7568	Intermediate Similarity	NPD2175	Phase 3
0.7568	Intermediate Similarity	NPD2177	Approved
0.7563	Intermediate Similarity	NPD1856	Discontinued
0.7558	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD4418	Discontinued
0.7541	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD3923	Approved
0.7527	Intermediate Similarity	NPD6569	Phase 2
0.7527	Intermediate Similarity	NPD3921	Approved
0.7527	Intermediate Similarity	NPD3922	Approved
0.7527	Intermediate Similarity	NPD3924	Approved
0.7514	Intermediate Similarity	NPD2410	Phase 2
0.7513	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2581	Approved
0.75	Intermediate Similarity	NPD2582	Approved
0.7486	Intermediate Similarity	NPD9695	Approved
0.7485	Intermediate Similarity	NPD1305	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7452	Approved
0.7474	Intermediate Similarity	NPD7453	Approved
0.746	Intermediate Similarity	NPD4795	Phase 2
0.7459	Intermediate Similarity	NPD9714	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD9689	Approved
0.7429	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5530	Phase 1
0.7419	Intermediate Similarity	NPD712	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1034	Phase 3
0.7389	Intermediate Similarity	NPD4889	Approved
0.738	Intermediate Similarity	NPD4548	Discontinued
0.7374	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3525	Discontinued
0.7353	Intermediate Similarity	NPD6060	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD5658	Approved
0.7337	Intermediate Similarity	NPD4372	Phase 1
0.7323	Intermediate Similarity	NPD3875	Discontinued
0.732	Intermediate Similarity	NPD5416	Discontinued
0.7318	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD3386	Phase 2
0.73	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6290	Phase 2
0.7287	Intermediate Similarity	NPD1768	Approved
0.7287	Intermediate Similarity	NPD3825	Phase 3
0.7273	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7395	Discontinued
0.7262	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6158	Phase 2
0.7258	Intermediate Similarity	NPD6251	Discontinued
0.7255	Intermediate Similarity	NPD5022	Discontinued
0.7253	Intermediate Similarity	NPD2917	Approved
0.724	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD6150	Discontinued
0.7236	Intermediate Similarity	NPD3514	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD5680	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD9688	Approved
0.7196	Intermediate Similarity	NPD9687	Approved
0.7194	Intermediate Similarity	NPD4927	Discontinued
0.7191	Intermediate Similarity	NPD4354	Approved
0.7172	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2882	Phase 1
0.716	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD565	Phase 2
0.7157	Intermediate Similarity	NPD3945	Discontinued
0.715	Intermediate Similarity	NPD3003	Approved
0.7143	Intermediate Similarity	NPD5936	Approved
0.7143	Intermediate Similarity	NPD5939	Approved
0.7143	Intermediate Similarity	NPD6220	Phase 3
0.7143	Intermediate Similarity	NPD7468	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD980	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6991	Approved
0.712	Intermediate Similarity	NPD2383	Phase 1
0.712	Intermediate Similarity	NPD6393	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD1418	Phase 2
0.7104	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2334	Discontinued
0.7097	Intermediate Similarity	NPD4148	Approved
0.7093	Intermediate Similarity	NPD1769	Discontinued
0.7092	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2782	Approved
0.7086	Intermediate Similarity	NPD2780	Approved
0.7085	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6643	Discontinued
0.7083	Intermediate Similarity	NPD1897	Discontinued
0.7083	Intermediate Similarity	NPD6208	Discontinued
0.7079	Intermediate Similarity	NPD5078	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD2076	Approved
0.7079	Intermediate Similarity	NPD2077	Approved
0.7077	Intermediate Similarity	NPD2187	Approved
0.7077	Intermediate Similarity	NPD5529	Phase 1
0.7077	Intermediate Similarity	NPD2189	Approved
0.7077	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD3396	Approved
0.7074	Intermediate Similarity	NPD3395	Approved
0.7069	Intermediate Similarity	NPD1684	Approved
0.7069	Intermediate Similarity	NPD1685	Approved
0.7067	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD3504	Approved
0.7056	Intermediate Similarity	NPD5670	Approved
0.7056	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4072	Approved
0.7056	Intermediate Similarity	NPD4071	Approved
0.7056	Intermediate Similarity	NPD1032	Phase 2
0.7056	Intermediate Similarity	NPD3503	Approved
0.705	Intermediate Similarity	NPD3440	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2749	Discontinued
0.7026	Intermediate Similarity	NPD1392	Approved
0.7021	Intermediate Similarity	NPD4551	Phase 2
0.702	Intermediate Similarity	NPD3815	Phase 1
0.702	Intermediate Similarity	NPD3816	Phase 1
0.702	Intermediate Similarity	NPD7069	Discontinued
0.7017	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD2778	Approved
0.7006	Intermediate Similarity	NPD2781	Approved
0.7005	Intermediate Similarity	NPD5913	Phase 3
0.7005	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5420	Discontinued
0.7	Intermediate Similarity	NPD5612	Discontinued
0.7	Intermediate Similarity	NPD3833	Phase 3
0.7	Intermediate Similarity	NPD4673	Phase 2
0.7	Intermediate Similarity	NPD3835	Phase 3
0.699	Remote Similarity	NPD7671	Approved
0.699	Remote Similarity	NPD7672	Approved
0.6983	Remote Similarity	NPD677	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2600	Approved
0.6978	Remote Similarity	NPD2599	Approved
0.6978	Remote Similarity	NPD2601	Approved
0.6973	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4921	Phase 3
0.6973	Remote Similarity	NPD4919	Phase 3
0.697	Remote Similarity	NPD5066	Phase 2
0.697	Remote Similarity	NPD5067	Phase 2
0.6965	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD9595	Approved
0.6959	Remote Similarity	NPD9596	Approved
0.695	Remote Similarity	NPD3257	Approved
0.695	Remote Similarity	NPD5902	Approved
0.695	Remote Similarity	NPD5903	Approved
0.6946	Remote Similarity	NPD5930	Phase 3
0.6932	Remote Similarity	NPD863	Approved
0.6932	Remote Similarity	NPD862	Approved
0.6932	Remote Similarity	NPD861	Approved
0.6931	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6361	Phase 2
0.6927	Remote Similarity	NPD4083	Discontinued
0.6919	Remote Similarity	NPD3006	Discontinued
0.6911	Remote Similarity	NPD4899	Clinical (unspecified phase)

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