NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	290.01
Volume:	241.984
LogP:	3.453
LogD:	3.147
LogS:	-4.165
# Rotatable Bonds:	1
TPSA:	37.91
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.74
Synthetic Accessibility Score:	2.53
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:	-4.821
MDCK Permeability:	1.5986503058229573e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.339
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.932
Plasma Protein Binding (PPB):	95.10570526123047%
Volume Distribution (VD):	1.147
Pgp-substrate:	3.904308795928955%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.922
CYP2C19-substrate:	0.628
CYP2C9-inhibitor:	0.735
CYP2C9-substrate:	0.863
CYP2D6-inhibitor:	0.88
CYP2D6-substrate:	0.88
CYP3A4-inhibitor:	0.743
CYP3A4-substrate:	0.583

ADMET: Excretion

Clearance (CL):	2.414
Half-life (T1/2):	0.356

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.81
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.639
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.699
Skin Sensitization:	0.769
Carcinogencity:	0.807
Eye Corrosion:	0.138
Eye Irritation:	0.96
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC292958

Natural Product ID:	NPC292958
*Common Name:**	5-Bromo-8-Methoxy-1-Methyl-Beta-Carboline
IUPAC Name:	5-bromo-8-methoxy-1-methyl-9H-pyrido[3,4-b]indole
Synonyms:
Standard InCHIKey:	OVNRKQHNHZRXHF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H11BrN2O/c1-7-12-8(5-6-15-7)11-9(14)3-4-10(17-2)13(11)16-12/h3-6,16H,1-2H3
SMILES:	COc1ccc(c2c1[nH]c1c2ccnc1C)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL540307
PubChem CID:	42638980
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14600382]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562843]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	New Zealand	n.a.	PMID[18052329]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	Alderman Islands off the North Island of New Zealand	n.a.	PMID[18052329]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	New Zealand	n.a.	PMID[19220033]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19220033]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[25894905]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28358502]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26055	Relhania fruticosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	3

Activity Type	# Activity
Cell Line	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	5.089	ug.mL-1	PMID[475836]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MID	=	7.5	ug ml-1	PMID[475836]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MID	=	2.0	ug ml-1	PMID[475836]
NPT20	Organism	Candida albicans	Candida albicans	MID	=	7.5	ug ml-1	PMID[475836]

☑ 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 NPC292958 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	995
0.1-0.2	10346
0.2-0.3	7676
0.3-0.4	16395
0.4-0.5	3655
0.5-0.6	2300
0.6-0.7	1160
0.7-0.8	151
0.8-0.85	12
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9179	High Similarity	NPC476138
0.9179	High Similarity	NPC245816
0.8762	High Similarity	NPC185782
0.8683	High Similarity	NPC476287
0.8643	High Similarity	NPC19872
0.8634	High Similarity	NPC26679
0.855	High Similarity	NPC176538
0.851	High Similarity	NPC8022
0.851	High Similarity	NPC470799
0.8408	Intermediate Similarity	NPC476167
0.8358	Intermediate Similarity	NPC192315
0.8325	Intermediate Similarity	NPC232727
0.8218	Intermediate Similarity	NPC267928
0.8164	Intermediate Similarity	NPC476124
0.8136	Intermediate Similarity	NPC469554
0.8136	Intermediate Similarity	NPC101543
0.803	Intermediate Similarity	NPC284678
0.8028	Intermediate Similarity	NPC245348
0.8019	Intermediate Similarity	NPC473761
0.8009	Intermediate Similarity	NPC167860
0.8009	Intermediate Similarity	NPC123976
0.7991	Intermediate Similarity	NPC60006
0.799	Intermediate Similarity	NPC476121
0.796	Intermediate Similarity	NPC296527
0.796	Intermediate Similarity	NPC242928
0.7929	Intermediate Similarity	NPC474798
0.7921	Intermediate Similarity	NPC76748
0.7895	Intermediate Similarity	NPC475774
0.7885	Intermediate Similarity	NPC98685
0.7882	Intermediate Similarity	NPC92111
0.7838	Intermediate Similarity	NPC314954
0.783	Intermediate Similarity	NPC287208
0.7805	Intermediate Similarity	NPC307963
0.7773	Intermediate Similarity	NPC285558
0.7746	Intermediate Similarity	NPC82548
0.7743	Intermediate Similarity	NPC97902
0.7729	Intermediate Similarity	NPC251090
0.7721	Intermediate Similarity	NPC208284
0.7717	Intermediate Similarity	NPC193267
0.7717	Intermediate Similarity	NPC213530
0.7692	Intermediate Similarity	NPC470501
0.7689	Intermediate Similarity	NPC470505
0.7689	Intermediate Similarity	NPC260434
0.7685	Intermediate Similarity	NPC94157
0.7674	Intermediate Similarity	NPC5145
0.7652	Intermediate Similarity	NPC148889
0.765	Intermediate Similarity	NPC26543
0.7647	Intermediate Similarity	NPC60621
0.7647	Intermediate Similarity	NPC470502
0.7647	Intermediate Similarity	NPC310118
0.7624	Intermediate Similarity	NPC176127
0.7619	Intermediate Similarity	NPC128823
0.7606	Intermediate Similarity	NPC475070
0.759	Intermediate Similarity	NPC118511
0.7583	Intermediate Similarity	NPC315957
0.7583	Intermediate Similarity	NPC121772
0.7578	Intermediate Similarity	NPC470503
0.7578	Intermediate Similarity	NPC122436
0.7569	Intermediate Similarity	NPC477610
0.756	Intermediate Similarity	NPC13880
0.7559	Intermediate Similarity	NPC223427
0.7548	Intermediate Similarity	NPC84853
0.7546	Intermediate Similarity	NPC174758
0.7537	Intermediate Similarity	NPC48938
0.7523	Intermediate Similarity	NPC470500
0.75	Intermediate Similarity	NPC324149
0.75	Intermediate Similarity	NPC142901
0.749	Intermediate Similarity	NPC53534
0.7478	Intermediate Similarity	NPC110151
0.7476	Intermediate Similarity	NPC222018
0.7465	Intermediate Similarity	NPC174672
0.7465	Intermediate Similarity	NPC473181
0.7464	Intermediate Similarity	NPC198673
0.7464	Intermediate Similarity	NPC475190
0.7444	Intermediate Similarity	NPC132642
0.7431	Intermediate Similarity	NPC199667
0.7422	Intermediate Similarity	NPC167908
0.7415	Intermediate Similarity	NPC84478
0.7414	Intermediate Similarity	NPC30540
0.7403	Intermediate Similarity	NPC295228
0.7374	Intermediate Similarity	NPC274229
0.7364	Intermediate Similarity	NPC473180
0.7354	Intermediate Similarity	NPC477609
0.7342	Intermediate Similarity	NPC274982
0.7339	Intermediate Similarity	NPC476465
0.7336	Intermediate Similarity	NPC329793
0.733	Intermediate Similarity	NPC266931
0.733	Intermediate Similarity	NPC204717
0.733	Intermediate Similarity	NPC162530
0.7324	Intermediate Similarity	NPC168911
0.7324	Intermediate Similarity	NPC239954
0.7316	Intermediate Similarity	NPC180504
0.7313	Intermediate Similarity	NPC82331
0.7306	Intermediate Similarity	NPC152620
0.7304	Intermediate Similarity	NPC476451
0.7297	Intermediate Similarity	NPC470549
0.7295	Intermediate Similarity	NPC314002
0.729	Intermediate Similarity	NPC187558
0.729	Intermediate Similarity	NPC287437
0.7285	Intermediate Similarity	NPC118940
0.7284	Intermediate Similarity	NPC182222
0.7282	Intermediate Similarity	NPC220765
0.7269	Intermediate Similarity	NPC471891
0.7265	Intermediate Similarity	NPC170114
0.7264	Intermediate Similarity	NPC473764
0.7264	Intermediate Similarity	NPC314940
0.726	Intermediate Similarity	NPC171171
0.726	Intermediate Similarity	NPC266249
0.7256	Intermediate Similarity	NPC234197
0.7249	Intermediate Similarity	NPC473185
0.7244	Intermediate Similarity	NPC255110
0.724	Intermediate Similarity	NPC187501
0.7233	Intermediate Similarity	NPC161887
0.7232	Intermediate Similarity	NPC304926
0.7232	Intermediate Similarity	NPC476041
0.7227	Intermediate Similarity	NPC80596
0.7222	Intermediate Similarity	NPC235685
0.7212	Intermediate Similarity	NPC42591
0.7212	Intermediate Similarity	NPC20249
0.7209	Intermediate Similarity	NPC18487
0.7207	Intermediate Similarity	NPC128084
0.7207	Intermediate Similarity	NPC316981
0.7206	Intermediate Similarity	NPC224764
0.7206	Intermediate Similarity	NPC474958
0.7202	Intermediate Similarity	NPC470930
0.7195	Intermediate Similarity	NPC123839
0.7191	Intermediate Similarity	NPC101350
0.7185	Intermediate Similarity	NPC470504
0.7176	Intermediate Similarity	NPC329747
0.7175	Intermediate Similarity	NPC39500
0.717	Intermediate Similarity	NPC99666
0.7168	Intermediate Similarity	NPC473179
0.7155	Intermediate Similarity	NPC475253
0.7143	Intermediate Similarity	NPC477608
0.7143	Intermediate Similarity	NPC477607
0.7136	Intermediate Similarity	NPC42979
0.7124	Intermediate Similarity	NPC473186
0.7117	Intermediate Similarity	NPC11464
0.7111	Intermediate Similarity	NPC288349
0.711	Intermediate Similarity	NPC211813
0.7103	Intermediate Similarity	NPC131017
0.7102	Intermediate Similarity	NPC258048
0.7098	Intermediate Similarity	NPC469592
0.7098	Intermediate Similarity	NPC471080
0.7097	Intermediate Similarity	NPC303820
0.7097	Intermediate Similarity	NPC205254
0.7097	Intermediate Similarity	NPC106771
0.7097	Intermediate Similarity	NPC23420
0.7094	Intermediate Similarity	NPC141053
0.7094	Intermediate Similarity	NPC476518
0.7094	Intermediate Similarity	NPC97343
0.7093	Intermediate Similarity	NPC288987
0.7093	Intermediate Similarity	NPC17565
0.7091	Intermediate Similarity	NPC470164
0.7091	Intermediate Similarity	NPC323345
0.7089	Intermediate Similarity	NPC133140
0.7089	Intermediate Similarity	NPC195268
0.7087	Intermediate Similarity	NPC184964
0.7083	Intermediate Similarity	NPC212213
0.7067	Intermediate Similarity	NPC219963
0.7067	Intermediate Similarity	NPC266551
0.7064	Intermediate Similarity	NPC24802
0.7064	Intermediate Similarity	NPC52909
0.7064	Intermediate Similarity	NPC39370
0.7064	Intermediate Similarity	NPC94211
0.7064	Intermediate Similarity	NPC475935
0.7062	Intermediate Similarity	NPC46580
0.7059	Intermediate Similarity	NPC14651
0.7059	Intermediate Similarity	NPC121658
0.7056	Intermediate Similarity	NPC470018
0.7051	Intermediate Similarity	NPC49547
0.7051	Intermediate Similarity	NPC200553
0.7051	Intermediate Similarity	NPC279189
0.7048	Intermediate Similarity	NPC184408
0.7045	Intermediate Similarity	NPC118832
0.7045	Intermediate Similarity	NPC47059
0.7045	Intermediate Similarity	NPC165349
0.7045	Intermediate Similarity	NPC329708
0.7045	Intermediate Similarity	NPC264166
0.7045	Intermediate Similarity	NPC274291
0.7043	Intermediate Similarity	NPC65277
0.704	Intermediate Similarity	NPC471304
0.7037	Intermediate Similarity	NPC77555
0.7029	Intermediate Similarity	NPC473312
0.7027	Intermediate Similarity	NPC477111
0.7026	Intermediate Similarity	NPC6215
0.7026	Intermediate Similarity	NPC74575
0.7024	Intermediate Similarity	NPC111624
0.7018	Intermediate Similarity	NPC208084
0.7018	Intermediate Similarity	NPC477019
0.7015	Intermediate Similarity	NPC177404
0.7014	Intermediate Similarity	NPC477113
0.7009	Intermediate Similarity	NPC246518
0.7004	Intermediate Similarity	NPC473183
0.6992	Remote Similarity	NPC473184
0.6987	Remote Similarity	NPC225279
0.6986	Remote Similarity	NPC314394
0.6986	Remote Similarity	NPC307191
0.6978	Remote Similarity	NPC207020
0.6977	Remote Similarity	NPC226202

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 NPC292958 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	463
0.1-0.2	877
0.2-0.3	684
0.3-0.4	2306
0.4-0.5	2490
0.5-0.6	1783
0.6-0.7	507
0.7-0.8	40
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
0.7892	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1038	Approved
0.7703	Intermediate Similarity	NPD4890	Phase 2
0.7606	Intermediate Similarity	NPD4795	Phase 2
0.7583	Intermediate Similarity	NPD1740	Approved
0.7583	Intermediate Similarity	NPD1739	Approved
0.7536	Intermediate Similarity	NPD3825	Phase 3
0.7487	Intermediate Similarity	NPD112	Approved
0.7487	Intermediate Similarity	NPD9705	Discontinued
0.7479	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1856	Discontinued
0.7371	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD4548	Discontinued
0.7368	Intermediate Similarity	NPD5559	Phase 2
0.7348	Intermediate Similarity	NPD2984	Phase 2
0.7346	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5612	Discontinued
0.7339	Intermediate Similarity	NPD5658	Approved
0.7339	Intermediate Similarity	NPD2189	Approved
0.7339	Intermediate Similarity	NPD2187	Approved
0.7297	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD4429	Discontinued
0.724	Intermediate Similarity	NPD5067	Phase 2
0.724	Intermediate Similarity	NPD5066	Phase 2
0.723	Intermediate Similarity	NPD3477	Phase 2
0.723	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1392	Approved
0.7215	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD5482	Discontinued
0.7179	Intermediate Similarity	NPD3006	Discontinued
0.7168	Intermediate Similarity	NPD3402	Phase 1
0.7137	Intermediate Similarity	NPD6242	Discontinued
0.7136	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6961	Discontinued
0.713	Intermediate Similarity	NPD7603	Discontinued
0.7111	Intermediate Similarity	NPD6643	Discontinued
0.7106	Intermediate Similarity	NPD4454	Phase 2
0.7098	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3923	Approved
0.7089	Intermediate Similarity	NPD3921	Approved
0.7089	Intermediate Similarity	NPD3922	Approved
0.7089	Intermediate Similarity	NPD3924	Approved
0.7085	Intermediate Similarity	NPD3939	Suspended
0.7085	Intermediate Similarity	NPD4502	Phase 2
0.7073	Intermediate Similarity	NPD9690	Approved
0.7062	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD1034	Phase 3
0.7059	Intermediate Similarity	NPD7222	Phase 2
0.7051	Intermediate Similarity	NPD5999	Phase 2
0.7045	Intermediate Similarity	NPD4033	Approved
0.7045	Intermediate Similarity	NPD32	Approved
0.7045	Intermediate Similarity	NPD4035	Approved
0.7045	Intermediate Similarity	NPD4034	Approved
0.7045	Intermediate Similarity	NPD4122	Approved
0.7045	Intermediate Similarity	NPD31	Approved
0.7045	Intermediate Similarity	NPD4037	Approved
0.7045	Intermediate Similarity	NPD4038	Approved
0.7045	Intermediate Similarity	NPD4036	Approved
0.7045	Intermediate Similarity	NPD4039	Approved
0.7031	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7558	Phase 2
0.7018	Intermediate Similarity	NPD3514	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5256	Discontinued
0.7014	Intermediate Similarity	NPD3003	Approved
0.7013	Intermediate Similarity	NPD1258	Discontinued
0.701	Intermediate Similarity	NPD565	Phase 2
0.7009	Intermediate Similarity	NPD6569	Phase 2
0.7009	Intermediate Similarity	NPD4372	Phase 1
0.7	Intermediate Similarity	NPD7067	Approved
0.7	Intermediate Similarity	NPD6991	Approved
0.7	Intermediate Similarity	NPD7068	Approved
0.7	Intermediate Similarity	NPD3343	Phase 3
0.6984	Remote Similarity	NPD3255	Phase 1
0.6984	Remote Similarity	NPD3254	Phase 1
0.6976	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5022	Discontinued
0.6959	Remote Similarity	NPD7948	Phase 1
0.6949	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4131	Phase 3
0.6926	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.692	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD1996	Discontinued
0.6906	Remote Similarity	NPD7452	Approved
0.6906	Remote Similarity	NPD7453	Approved
0.6905	Remote Similarity	NPD4203	Approved
0.6905	Remote Similarity	NPD4204	Approved
0.6905	Remote Similarity	NPD4442	Phase 2
0.6898	Remote Similarity	NPD802	Phase 2
0.6895	Remote Similarity	NPD1768	Approved
0.6894	Remote Similarity	NPD6969	Phase 2
0.6894	Remote Similarity	NPD6968	Phase 2
0.6894	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4558	Phase 2
0.6878	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7672	Approved
0.6875	Remote Similarity	NPD7671	Approved
0.6866	Remote Similarity	NPD4418	Discontinued
0.6866	Remote Similarity	NPD2581	Approved
0.6866	Remote Similarity	NPD2582	Approved
0.6865	Remote Similarity	NPD5450	Discontinued
0.6864	Remote Similarity	NPD484	Approved
0.6862	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5530	Phase 1
0.6858	Remote Similarity	NPD949	Phase 1
0.6842	Remote Similarity	NPD5902	Approved
0.6842	Remote Similarity	NPD5903	Approved
0.6836	Remote Similarity	NPD5018	Phase 3
0.6829	Remote Similarity	NPD424	Approved
0.6829	Remote Similarity	NPD425	Approved
0.6828	Remote Similarity	NPD3816	Phase 1
0.6828	Remote Similarity	NPD3815	Phase 1
0.6827	Remote Similarity	NPD5065	Approved
0.6825	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD8512	Phase 3
0.6818	Remote Similarity	NPD2177	Approved
0.6818	Remote Similarity	NPD2175	Phase 3
0.6818	Remote Similarity	NPD2176	Approved
0.6816	Remote Similarity	NPD5644	Phase 1
0.6816	Remote Similarity	NPD3397	Phase 2
0.6815	Remote Similarity	NPD8442	Discontinued
0.6808	Remote Similarity	NPD4889	Approved
0.6806	Remote Similarity	NPD5913	Phase 3
0.6806	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7194	Discontinued
0.6786	Remote Similarity	NPD5601	Phase 2
0.6778	Remote Similarity	NPD2951	Discontinued
0.6776	Remote Similarity	NPD4919	Phase 3
0.6776	Remote Similarity	NPD4921	Phase 3
0.6776	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1273	Discontinued
0.6762	Remote Similarity	NPD1032	Phase 2
0.6754	Remote Similarity	NPD3330	Phase 1
0.6751	Remote Similarity	NPD5479	Discontinued
0.6749	Remote Similarity	NPD6473	Phase 1
0.6744	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD9695	Approved
0.6737	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5529	Phase 1
0.6726	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD3938	Phase 1
0.6723	Remote Similarity	NPD6131	Phase 1
0.6722	Remote Similarity	NPD4343	Phase 1
0.6722	Remote Similarity	NPD4344	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD8403	Phase 1
0.671	Remote Similarity	NPD3440	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD706	Phase 1
0.6695	Remote Similarity	NPD4885	Approved
0.6695	Remote Similarity	NPD6856	Discontinued
0.6695	Remote Similarity	NPD5930	Phase 3
0.6682	Remote Similarity	NPD4072	Approved
0.6682	Remote Similarity	NPD4071	Approved
0.6681	Remote Similarity	NPD3354	Phase 2
0.6681	Remote Similarity	NPD6202	Discontinued
0.6681	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.668	Remote Similarity	NPD5891	Approved
0.668	Remote Similarity	NPD1259	Discontinued
0.668	Remote Similarity	NPD5051	Phase 1
0.6667	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3386	Phase 2
0.6667	Remote Similarity	NPD8100	Phase 3
0.6667	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2472	Approved
0.6667	Remote Similarity	NPD2471	Approved
0.6667	Remote Similarity	NPD7659	Discontinued
0.6667	Remote Similarity	NPD6494	Phase 2
0.6653	Remote Similarity	NPD5911	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD3920	Phase 2
0.6638	Remote Similarity	NPD5936	Approved
0.6638	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5939	Approved
0.6637	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6590	Discontinued
0.6634	Remote Similarity	NPD1418	Phase 2
0.6624	Remote Similarity	NPD7051	Phase 3
0.6624	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD9689	Approved
0.6611	Remote Similarity	NPD3302	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6306	Phase 2
0.6609	Remote Similarity	NPD6568	Discontinued
0.6609	Remote Similarity	NPD5632	Approved
0.6609	Remote Similarity	NPD6985	Discontinued
0.6608	Remote Similarity	NPD6290	Phase 2
0.6595	Remote Similarity	NPD7112	Discontinued
0.6595	Remote Similarity	NPD2763	Phase 2
0.6586	Remote Similarity	NPD8101	Phase 3
0.6581	Remote Similarity	NPD6500	Approved
0.6581	Remote Similarity	NPD6501	Approved
0.6581	Remote Similarity	NPD3763	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