NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	226.11
Volume:	239.996
LogP:	3.111
LogD:	3.072
LogS:	-3.239
# Rotatable Bonds:	2
TPSA:	37.91
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.728
Synthetic Accessibility Score:	2.294
Fsp3:	0.214
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:	-4.895
MDCK Permeability:	2.063902502413839e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.894
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.087

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.82
Plasma Protein Binding (PPB):	89.07939910888672%
Volume Distribution (VD):	1.631
Pgp-substrate:	5.928739070892334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.991
CYP1A2-substrate:	0.967
CYP2C19-inhibitor:	0.825
CYP2C19-substrate:	0.606
CYP2C9-inhibitor:	0.653
CYP2C9-substrate:	0.788
CYP2D6-inhibitor:	0.866
CYP2D6-substrate:	0.858
CYP3A4-inhibitor:	0.851
CYP3A4-substrate:	0.639

ADMET: Excretion

Clearance (CL):	5.178
Half-life (T1/2):	0.533

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.782
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.649
Rat Oral Acute Toxicity:	0.949
Maximum Recommended Daily Dose:	0.768
Skin Sensitization:	0.5
Carcinogencity:	0.547
Eye Corrosion:	0.024
Eye Irritation:	0.85
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC245816

Natural Product ID:	NPC245816
*Common Name:**	1-Ethyl-8-Methoxy-Beta-Carboline
IUPAC Name:	1-ethyl-8-methoxy-9H-pyrido[3,4-b]indole
Synonyms:
Standard InCHIKey:	XOBFACUQMALBEU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H14N2O/c1-3-11-13-10(7-8-15-11)9-5-4-6-12(17-2)14(9)16-13/h4-8,16H,3H2,1-2H3
SMILES:	CCc1c2c(ccn1)c1cccc(c1[nH]2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL558541
PubChem CID:	45267155
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
NPO2833	Cribricellina cribraria	Species	Catenicellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791472]
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]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19586051]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	stems	n.a.	n.a.	PMID[20095629]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25506718]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27494664]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30917277]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2833	Cribricellina cribraria	Species	Catenicellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	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]

☑ 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	2
MIC	6
Others	9

Activity Type	# Activity
Cell Line	2
Organism	15

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	12.5	ug.mL-1	PMID[464501]
NPT168	Cell Line	P388	Mus musculus	IC50	>	12.5	ug.mL-1	PMID[464502]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	60.0	ug	PMID[464501]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	60.0	ug	PMID[464501]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	60.0	ug	PMID[464501]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	7.5	ug	PMID[464501]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	7.5	ug	PMID[464501]
NPT1223	Organism	Amorphotheca resinae	Amorphotheca resinae	MIC	>	60.0	ug	PMID[464501]
NPT20	Organism	Candida albicans	Candida albicans	MID	=	7.5	ug ml-1	PMID[464502]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MID	>	60.0	ug ml-1	PMID[464502]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MID	=	7.5	ug ml-1	PMID[464502]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	50.0	%	PMID[464503]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	45.5	%	PMID[464503]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	48.4	%	PMID[464503]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	20.9	%	PMID[464503]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	36.4	%	PMID[464503]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	25.0	%	PMID[464503]

☑ 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 NPC245816 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	808
0.1-0.2	6486
0.2-0.3	10921
0.3-0.4	13792
0.4-0.5	6125
0.5-0.6	2360
0.6-0.7	1695
0.7-0.8	445
0.8-0.85	32
0.85-0.9	19
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476138
0.9519	High Similarity	NPC185782
0.9421	High Similarity	NPC476287
0.9402	High Similarity	NPC19872
0.9368	High Similarity	NPC26679
0.9297	High Similarity	NPC176538
0.9223	High Similarity	NPC8022
0.9223	High Similarity	NPC470799
0.9179	High Similarity	NPC292958
0.914	High Similarity	NPC476167
0.9086	High Similarity	NPC192315
0.9043	High Similarity	NPC232727
0.893	High Similarity	NPC267928
0.878	High Similarity	NPC469554
0.878	High Similarity	NPC101543
0.8743	High Similarity	NPC284678
0.8673	High Similarity	NPC123976
0.8673	High Similarity	NPC167860
0.8656	High Similarity	NPC296527
0.8656	High Similarity	NPC242928
0.8634	High Similarity	NPC474798
0.861	High Similarity	NPC76748
0.8564	High Similarity	NPC92111
0.8557	High Similarity	NPC475774
0.8477	Intermediate Similarity	NPC287208
0.8474	Intermediate Similarity	NPC307963
0.8454	Intermediate Similarity	NPC314954
0.8418	Intermediate Similarity	NPC285558
0.8385	Intermediate Similarity	NPC251090
0.8384	Intermediate Similarity	NPC82548
0.835	Intermediate Similarity	NPC208284
0.8333	Intermediate Similarity	NPC213530
0.8333	Intermediate Similarity	NPC193267
0.8308	Intermediate Similarity	NPC94157
0.83	Intermediate Similarity	NPC5145
0.8289	Intermediate Similarity	NPC176127
0.8286	Intermediate Similarity	NPC260434
0.8278	Intermediate Similarity	NPC118511
0.8256	Intermediate Similarity	NPC128823
0.8252	Intermediate Similarity	NPC310118
0.8252	Intermediate Similarity	NPC60621
0.8233	Intermediate Similarity	NPC148889
0.8232	Intermediate Similarity	NPC475070
0.8219	Intermediate Similarity	NPC26543
0.8214	Intermediate Similarity	NPC121772
0.8214	Intermediate Similarity	NPC315957
0.8196	Intermediate Similarity	NPC13880
0.8191	Intermediate Similarity	NPC48938
0.8187	Intermediate Similarity	NPC84853
0.8182	Intermediate Similarity	NPC223427
0.8173	Intermediate Similarity	NPC122436
0.8159	Intermediate Similarity	NPC174758
0.8141	Intermediate Similarity	NPC470500
0.8135	Intermediate Similarity	NPC324149
0.8093	Intermediate Similarity	NPC198673
0.8093	Intermediate Similarity	NPC475190
0.8069	Intermediate Similarity	NPC174672
0.8069	Intermediate Similarity	NPC473181
0.8057	Intermediate Similarity	NPC110151
0.8053	Intermediate Similarity	NPC84478
0.8036	Intermediate Similarity	NPC53534
0.803	Intermediate Similarity	NPC199667
0.8029	Intermediate Similarity	NPC132642
0.7972	Intermediate Similarity	NPC30540
0.7963	Intermediate Similarity	NPC295228
0.7958	Intermediate Similarity	NPC204717
0.7951	Intermediate Similarity	NPC473180
0.794	Intermediate Similarity	NPC329793
0.7931	Intermediate Similarity	NPC476465
0.7929	Intermediate Similarity	NPC168911
0.7929	Intermediate Similarity	NPC239954
0.7923	Intermediate Similarity	NPC274982
0.7917	Intermediate Similarity	NPC314002
0.7913	Intermediate Similarity	NPC162530
0.7913	Intermediate Similarity	NPC266931
0.7906	Intermediate Similarity	NPC220765
0.7903	Intermediate Similarity	NPC473764
0.7903	Intermediate Similarity	NPC314940
0.7889	Intermediate Similarity	NPC187558
0.7889	Intermediate Similarity	NPC287437
0.7876	Intermediate Similarity	NPC171171
0.7874	Intermediate Similarity	NPC470549
0.787	Intermediate Similarity	NPC180504
0.7864	Intermediate Similarity	NPC118940
0.786	Intermediate Similarity	NPC476451
0.7853	Intermediate Similarity	NPC161887
0.785	Intermediate Similarity	NPC234197
0.7843	Intermediate Similarity	NPC266249
0.7837	Intermediate Similarity	NPC170114
0.7834	Intermediate Similarity	NPC182222
0.7831	Intermediate Similarity	NPC224764
0.7826	Intermediate Similarity	NPC152620
0.7824	Intermediate Similarity	NPC42591
0.7824	Intermediate Similarity	NPC20249
0.7816	Intermediate Similarity	NPC187501
0.7804	Intermediate Similarity	NPC473185
0.7803	Intermediate Similarity	NPC471891
0.78	Intermediate Similarity	NPC18487
0.7799	Intermediate Similarity	NPC304926
0.7799	Intermediate Similarity	NPC476041
0.7783	Intermediate Similarity	NPC470930
0.7778	Intermediate Similarity	NPC316981
0.7767	Intermediate Similarity	NPC123839
0.7766	Intermediate Similarity	NPC99666
0.7763	Intermediate Similarity	NPC235685
0.7761	Intermediate Similarity	NPC329747
0.7749	Intermediate Similarity	NPC42979
0.774	Intermediate Similarity	NPC39500
0.7727	Intermediate Similarity	NPC101350
0.7725	Intermediate Similarity	NPC473179
0.7713	Intermediate Similarity	NPC476518
0.7696	Intermediate Similarity	NPC184964
0.7696	Intermediate Similarity	NPC475253
0.7688	Intermediate Similarity	NPC131017
0.7685	Intermediate Similarity	NPC211813
0.7685	Intermediate Similarity	NPC473761
0.7681	Intermediate Similarity	NPC11464
0.7677	Intermediate Similarity	NPC133140
0.7677	Intermediate Similarity	NPC195268
0.7672	Intermediate Similarity	NPC14651
0.7672	Intermediate Similarity	NPC121658
0.7668	Intermediate Similarity	NPC219963
0.7668	Intermediate Similarity	NPC266551
0.7667	Intermediate Similarity	NPC288349
0.7662	Intermediate Similarity	NPC212213
0.7661	Intermediate Similarity	NPC473186
0.7659	Intermediate Similarity	NPC470164
0.7659	Intermediate Similarity	NPC323345
0.7656	Intermediate Similarity	NPC469592
0.7656	Intermediate Similarity	NPC471080
0.7653	Intermediate Similarity	NPC46580
0.7642	Intermediate Similarity	NPC17565
0.7642	Intermediate Similarity	NPC288987
0.7634	Intermediate Similarity	NPC177404
0.7632	Intermediate Similarity	NPC111624
0.7626	Intermediate Similarity	NPC141053
0.7612	Intermediate Similarity	NPC77555
0.761	Intermediate Similarity	NPC165349
0.761	Intermediate Similarity	NPC274291
0.761	Intermediate Similarity	NPC329708
0.761	Intermediate Similarity	NPC118832
0.761	Intermediate Similarity	NPC264166
0.761	Intermediate Similarity	NPC47059
0.7609	Intermediate Similarity	NPC258048
0.7596	Intermediate Similarity	NPC471304
0.7596	Intermediate Similarity	NPC26872
0.7594	Intermediate Similarity	NPC184408
0.7593	Intermediate Similarity	NPC470018
0.7591	Intermediate Similarity	NPC24802
0.7591	Intermediate Similarity	NPC39370
0.7586	Intermediate Similarity	NPC477019
0.7585	Intermediate Similarity	NPC477111
0.7581	Intermediate Similarity	NPC65277
0.758	Intermediate Similarity	NPC49547
0.7579	Intermediate Similarity	NPC252590
0.7577	Intermediate Similarity	NPC314394
0.7573	Intermediate Similarity	NPC476121
0.7573	Intermediate Similarity	NPC476124
0.7573	Intermediate Similarity	NPC477113
0.7569	Intermediate Similarity	NPC179787
0.7569	Intermediate Similarity	NPC201380
0.7568	Intermediate Similarity	NPC26850
0.7566	Intermediate Similarity	NPC1527
0.7559	Intermediate Similarity	NPC208084
0.7558	Intermediate Similarity	NPC74575
0.7558	Intermediate Similarity	NPC6215
0.755	Intermediate Similarity	NPC226202
0.7545	Intermediate Similarity	NPC473312
0.7537	Intermediate Similarity	NPC476578
0.7537	Intermediate Similarity	NPC4071
0.7537	Intermediate Similarity	NPC476582
0.7535	Intermediate Similarity	NPC470501
0.7527	Intermediate Similarity	NPC321911
0.7524	Intermediate Similarity	NPC470505
0.7523	Intermediate Similarity	NPC225279
0.7523	Intermediate Similarity	NPC473183
0.7514	Intermediate Similarity	NPC63545
0.7512	Intermediate Similarity	NPC469594
0.7511	Intermediate Similarity	NPC473184
0.75	Intermediate Similarity	NPC475910
0.7488	Intermediate Similarity	NPC472111
0.7488	Intermediate Similarity	NPC470502
0.7487	Intermediate Similarity	NPC134079
0.7477	Intermediate Similarity	NPC257851
0.7476	Intermediate Similarity	NPC53144
0.7473	Intermediate Similarity	NPC469811
0.7465	Intermediate Similarity	NPC245348
0.7465	Intermediate Similarity	NPC473513
0.7464	Intermediate Similarity	NPC209769
0.7463	Intermediate Similarity	NPC106937
0.7456	Intermediate Similarity	NPC63971
0.7456	Intermediate Similarity	NPC91868
0.7454	Intermediate Similarity	NPC144452
0.7454	Intermediate Similarity	NPC280272
0.7452	Intermediate Similarity	NPC313189
0.744	Intermediate Similarity	NPC16452
0.744	Intermediate Similarity	NPC476581
0.744	Intermediate Similarity	NPC36229
0.7438	Intermediate Similarity	NPC70956
0.7438	Intermediate Similarity	NPC243834

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 NPC245816 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	395
0.1-0.2	705
0.2-0.3	742
0.3-0.4	1753
0.4-0.5	2390
0.5-0.6	2060
0.6-0.7	922
0.7-0.8	176
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD1304	Clinical (unspecified phase)
0.8474	Intermediate Similarity	NPD1038	Approved
0.8232	Intermediate Similarity	NPD4795	Phase 2
0.8214	Intermediate Similarity	NPD1739	Approved
0.8214	Intermediate Similarity	NPD1740	Approved
0.8167	Intermediate Similarity	NPD9705	Discontinued
0.8167	Intermediate Similarity	NPD112	Approved
0.8163	Intermediate Similarity	NPD3825	Phase 3
0.8037	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.8018	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.798	Intermediate Similarity	NPD4548	Discontinued
0.798	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD1856	Discontinued
0.7934	Intermediate Similarity	NPD5559	Phase 2
0.7931	Intermediate Similarity	NPD2187	Approved
0.7931	Intermediate Similarity	NPD5658	Approved
0.7931	Intermediate Similarity	NPD2189	Approved
0.7923	Intermediate Similarity	NPD5612	Discontinued
0.7874	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD4429	Discontinued
0.7828	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7828	Intermediate Similarity	NPD3477	Phase 2
0.7816	Intermediate Similarity	NPD5067	Phase 2
0.7816	Intermediate Similarity	NPD5066	Phase 2
0.7794	Intermediate Similarity	NPD1392	Approved
0.7748	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5482	Discontinued
0.7727	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD3402	Phase 1
0.7717	Intermediate Similarity	NPD3006	Discontinued
0.7689	Intermediate Similarity	NPD6242	Discontinued
0.7684	Intermediate Similarity	NPD9690	Approved
0.7677	Intermediate Similarity	NPD3921	Approved
0.7677	Intermediate Similarity	NPD3923	Approved
0.7677	Intermediate Similarity	NPD3922	Approved
0.7677	Intermediate Similarity	NPD3924	Approved
0.7674	Intermediate Similarity	NPD7603	Discontinued
0.7667	Intermediate Similarity	NPD6643	Discontinued
0.7656	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD1034	Phase 3
0.7653	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD3939	Suspended
0.7644	Intermediate Similarity	NPD4502	Phase 2
0.7642	Intermediate Similarity	NPD6961	Discontinued
0.7636	Intermediate Similarity	NPD4454	Phase 2
0.7624	Intermediate Similarity	NPD5999	Phase 2
0.7621	Intermediate Similarity	NPD7222	Phase 2
0.7619	Intermediate Similarity	NPD565	Phase 2
0.761	Intermediate Similarity	NPD4038	Approved
0.761	Intermediate Similarity	NPD4039	Approved
0.761	Intermediate Similarity	NPD4122	Approved
0.761	Intermediate Similarity	NPD4037	Approved
0.761	Intermediate Similarity	NPD32	Approved
0.761	Intermediate Similarity	NPD4036	Approved
0.761	Intermediate Similarity	NPD4035	Approved
0.761	Intermediate Similarity	NPD31	Approved
0.761	Intermediate Similarity	NPD4034	Approved
0.761	Intermediate Similarity	NPD4033	Approved
0.7602	Intermediate Similarity	NPD5256	Discontinued
0.7588	Intermediate Similarity	NPD4372	Phase 1
0.7588	Intermediate Similarity	NPD6569	Phase 2
0.7579	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD3003	Approved
0.757	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD3514	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1258	Discontinued
0.7545	Intermediate Similarity	NPD7558	Phase 2
0.7525	Intermediate Similarity	NPD7948	Phase 1
0.7511	Intermediate Similarity	NPD7067	Approved
0.7511	Intermediate Similarity	NPD7068	Approved
0.75	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD5022	Discontinued
0.7489	Intermediate Similarity	NPD3343	Phase 3
0.7487	Intermediate Similarity	NPD4203	Approved
0.7487	Intermediate Similarity	NPD4204	Approved
0.7476	Intermediate Similarity	NPD4131	Phase 3
0.7474	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD2582	Approved
0.7473	Intermediate Similarity	NPD2581	Approved
0.7466	Intermediate Similarity	NPD6223	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD802	Phase 2
0.7454	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7452	Approved
0.7452	Intermediate Similarity	NPD7453	Approved
0.7451	Intermediate Similarity	NPD1768	Approved
0.7426	Intermediate Similarity	NPD4418	Discontinued
0.7421	Intermediate Similarity	NPD424	Approved
0.7421	Intermediate Similarity	NPD425	Approved
0.7415	Intermediate Similarity	NPD484	Approved
0.7409	Intermediate Similarity	NPD6968	Phase 2
0.7409	Intermediate Similarity	NPD6969	Phase 2
0.7409	Intermediate Similarity	NPD5065	Approved
0.7404	Intermediate Similarity	NPD5530	Phase 1
0.7398	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7393	Intermediate Similarity	NPD949	Phase 1
0.7384	Intermediate Similarity	NPD4442	Phase 2
0.738	Intermediate Similarity	NPD4558	Phase 2
0.7374	Intermediate Similarity	NPD4889	Approved
0.7371	Intermediate Similarity	NPD5903	Approved
0.7371	Intermediate Similarity	NPD5902	Approved
0.7366	Intermediate Similarity	NPD2176	Approved
0.7366	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD2175	Phase 3
0.7366	Intermediate Similarity	NPD2177	Approved
0.7363	Intermediate Similarity	NPD5913	Phase 3
0.7363	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3815	Phase 1
0.7358	Intermediate Similarity	NPD3816	Phase 1
0.7356	Intermediate Similarity	NPD3397	Phase 2
0.7342	Intermediate Similarity	NPD5450	Discontinued
0.7337	Intermediate Similarity	NPD4921	Phase 3
0.7337	Intermediate Similarity	NPD4919	Phase 3
0.7337	Intermediate Similarity	NPD4920	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1032	Phase 2
0.7321	Intermediate Similarity	NPD5601	Phase 2
0.7315	Intermediate Similarity	NPD7194	Discontinued
0.7304	Intermediate Similarity	NPD5644	Phase 1
0.7303	Intermediate Similarity	NPD5018	Phase 3
0.73	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD8442	Discontinued
0.7291	Intermediate Similarity	NPD9695	Approved
0.7277	Intermediate Similarity	NPD3330	Phase 1
0.7277	Intermediate Similarity	NPD2951	Discontinued
0.7273	Intermediate Similarity	NPD1273	Discontinued
0.7255	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD8512	Phase 3
0.7252	Intermediate Similarity	NPD5479	Discontinued
0.7251	Intermediate Similarity	NPD5529	Phase 1
0.7251	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD706	Phase 1
0.7245	Intermediate Similarity	NPD4072	Approved
0.7245	Intermediate Similarity	NPD4071	Approved
0.724	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD8403	Phase 1
0.7237	Intermediate Similarity	NPD6473	Phase 1
0.7232	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD3938	Phase 1
0.7227	Intermediate Similarity	NPD4890	Phase 2
0.7222	Intermediate Similarity	NPD3440	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3386	Phase 2
0.722	Intermediate Similarity	NPD6131	Phase 1
0.7212	Intermediate Similarity	NPD4343	Phase 1
0.7212	Intermediate Similarity	NPD4344	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1418	Phase 2
0.7208	Intermediate Similarity	NPD3920	Phase 2
0.7208	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5930	Phase 3
0.7202	Intermediate Similarity	NPD6856	Discontinued
0.7196	Intermediate Similarity	NPD6202	Discontinued
0.7189	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD3354	Phase 2
0.7188	Intermediate Similarity	NPD4885	Approved
0.7177	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6590	Discontinued
0.7168	Intermediate Similarity	NPD1259	Discontinued
0.7157	Intermediate Similarity	NPD9689	Approved
0.7156	Intermediate Similarity	NPD2471	Approved
0.7156	Intermediate Similarity	NPD6494	Phase 2
0.7156	Intermediate Similarity	NPD2472	Approved
0.7156	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD4023	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5936	Approved
0.715	Intermediate Similarity	NPD5939	Approved
0.7143	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8100	Phase 3
0.7137	Intermediate Similarity	NPD7659	Discontinued
0.7136	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6290	Phase 2
0.7119	Intermediate Similarity	NPD5911	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7050	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7051	Phase 3
0.7114	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6568	Discontinued
0.711	Intermediate Similarity	NPD6985	Discontinued
0.711	Intermediate Similarity	NPD5632	Approved
0.7104	Intermediate Similarity	NPD6306	Phase 2
0.7101	Intermediate Similarity	NPD1229	Phase 2
0.7098	Intermediate Similarity	NPD926	Approved
0.7098	Intermediate Similarity	NPD925	Approved
0.7098	Intermediate Similarity	NPD2780	Approved
0.7098	Intermediate Similarity	NPD2782	Approved
0.7097	Intermediate Similarity	NPD7112	Discontinued
0.7087	Intermediate Similarity	NPD3395	Approved
0.7087	Intermediate Similarity	NPD3396	Approved
0.7087	Intermediate Similarity	NPD6251	Discontinued
0.7085	Intermediate Similarity	NPD6595	Phase 3
0.7085	Intermediate Similarity	NPD2600	Approved
0.7085	Intermediate Similarity	NPD2599	Approved
0.7085	Intermediate Similarity	NPD2601	Approved
0.7083	Intermediate Similarity	NPD2616	Phase 3
0.7083	Intermediate Similarity	NPD2615	Phase 3
0.7078	Intermediate 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