NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.12
Volume:	251.423
LogP:	1.911
LogD:	1.643
LogS:	-1.523
# Rotatable Bonds:	2
TPSA:	54.12
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.753
Synthetic Accessibility Score:	3.204
Fsp3:	0.357
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.826
MDCK Permeability:	1.3339402357814834e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.638
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.431
Plasma Protein Binding (PPB):	27.005624771118164%
Volume Distribution (VD):	1.379
Pgp-substrate:	70.96989440917969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.842
CYP1A2-substrate:	0.801
CYP2C19-inhibitor:	0.691
CYP2C19-substrate:	0.227
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.247
CYP2D6-inhibitor:	0.167
CYP2D6-substrate:	0.884
CYP3A4-inhibitor:	0.3
CYP3A4-substrate:	0.623

ADMET: Excretion

Clearance (CL):	3.563
Half-life (T1/2):	0.526

ADMET: Toxicity

hERG Blockers:	0.236
Human Hepatotoxicity (H-HT):	0.565
Drug-inuced Liver Injury (DILI):	0.366
AMES Toxicity:	0.251
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.311
Carcinogencity:	0.258
Eye Corrosion:	0.005
Eye Irritation:	0.012
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC469896

Natural Product ID:	NPC469896
*Common Name:**	Sid4250872
IUPAC Name:	methyl 1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
Synonyms:
Standard InCHIKey:	WZHYQHKXXRMALW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H16N2O2/c1-8-13-10(7-12(15-8)14(17)18-2)9-5-3-4-6-11(9)16-13/h3-6,8,12,15-16H,7H2,1-2H3
SMILES:	COC(=O)C1NC(C)c2c(C1)c1ccccc1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL12327
PubChem CID:	593930
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]
NPO2833	Cribricellina cribraria	Species	Catenicellidae	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
Ki	1
MIC	6
Others	1
Potency	14

Activity Type	# Activity
Cell Line	1
Individual Protein	11
Organism	8
Others	1
Protein Complex	1
PROTEIN-PROTEIN INTERACTION	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	120.0	ug.mL-1	PMID[522537]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	12589.3	nM	PMID[522538]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	19952.6	nM	PMID[522538]
NPT1197	Individual Protein	Huntingtin	Homo sapiens	Potency	=	1258.9	nM	PMID[522538]
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	3981.1	nM	PMID[522538]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[522538]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	6513.1	nM	PMID[522538]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[522538]
NPT1474	Individual Protein	ATP-dependent Clp protease proteolytic subunit	Bacillus subtilis (strain 168)	Potency	n.a.	35481.3	nM	PMID[522538]
NPT805	Protein Complex	GABA-A receptor; anion channel	Rattus norvegicus	Ki	>	50000.0	nM	PMID[522536]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	60.0	ug	PMID[522537]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	60.0	ug	PMID[522537]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	60.0	ug	PMID[522537]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	7.5	ug	PMID[522537]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	60.0	ug	PMID[522537]
NPT1223	Organism	Amorphotheca resinae	Amorphotheca resinae	MIC	>	60.0	ug	PMID[522537]
NPT2	Others	Unspecified		Potency	=	20596.2	nM	PMID[522538]
NPT21702	PROTEIN-PROTEIN INTERACTION	Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	63095.7	nM	PMID[522538]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PMID[522538]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	56234.1	nM	PMID[522538]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	67455.5	nM	PMID[522538]
NPT1328	Organism	Culex quinquefasciatus	Culex quinquefasciatus	mortality	<	34.85	%	PMID[522539]

☑ 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 NPC469896 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	289
0.1-0.2	2553
0.2-0.3	14531
0.3-0.4	17357
0.4-0.5	3067
0.5-0.6	2564
0.6-0.7	1643
0.7-0.8	579
0.8-0.85	83
0.85-0.9	26
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9571	High Similarity	NPC219336
0.9509	High Similarity	NPC15573
0.9509	High Similarity	NPC217372
0.9509	High Similarity	NPC183662
0.8929	High Similarity	NPC145885
0.8929	High Similarity	NPC84827
0.8929	High Similarity	NPC14113
0.883	High Similarity	NPC143533
0.8793	High Similarity	NPC111602
0.8793	High Similarity	NPC102338
0.8793	High Similarity	NPC196251
0.8793	High Similarity	NPC63199
0.8793	High Similarity	NPC175474
0.8765	High Similarity	NPC248041
0.8765	High Similarity	NPC126709
0.8655	High Similarity	NPC283219
0.8647	High Similarity	NPC267885
0.8596	High Similarity	NPC472210
0.8596	High Similarity	NPC81802
0.8596	High Similarity	NPC247735
0.8596	High Similarity	NPC269886
0.8596	High Similarity	NPC472295
0.8588	High Similarity	NPC149155
0.8588	High Similarity	NPC203468
0.8588	High Similarity	NPC110500
0.8547	High Similarity	NPC220151
0.8547	High Similarity	NPC19692
0.8531	High Similarity	NPC472112
0.8508	High Similarity	NPC52557
0.8478	Intermediate Similarity	NPC476098
0.8466	Intermediate Similarity	NPC235684
0.8436	Intermediate Similarity	NPC472113
0.8427	Intermediate Similarity	NPC329858
0.8427	Intermediate Similarity	NPC314333
0.8415	Intermediate Similarity	NPC81654
0.8415	Intermediate Similarity	NPC195461
0.8415	Intermediate Similarity	NPC49196
0.8415	Intermediate Similarity	NPC313985
0.8415	Intermediate Similarity	NPC249150
0.8415	Intermediate Similarity	NPC79129
0.8398	Intermediate Similarity	NPC245916
0.8391	Intermediate Similarity	NPC91179
0.8362	Intermediate Similarity	NPC62749
0.8353	Intermediate Similarity	NPC78020
0.8352	Intermediate Similarity	NPC472119
0.8343	Intermediate Similarity	NPC289299
0.8343	Intermediate Similarity	NPC57994
0.8315	Intermediate Similarity	NPC128265
0.8315	Intermediate Similarity	NPC312870
0.8315	Intermediate Similarity	NPC254240
0.8315	Intermediate Similarity	NPC214428
0.8315	Intermediate Similarity	NPC294909
0.8315	Intermediate Similarity	NPC199851
0.8314	Intermediate Similarity	NPC161861
0.8306	Intermediate Similarity	NPC50503
0.8297	Intermediate Similarity	NPC472116
0.8284	Intermediate Similarity	NPC21174
0.8284	Intermediate Similarity	NPC271797
0.8268	Intermediate Similarity	NPC321708
0.8251	Intermediate Similarity	NPC141454
0.8235	Intermediate Similarity	NPC132539
0.8232	Intermediate Similarity	NPC55493
0.8232	Intermediate Similarity	NPC472292
0.8226	Intermediate Similarity	NPC474116
0.822	Intermediate Similarity	NPC118940
0.8177	Intermediate Similarity	NPC472291
0.8171	Intermediate Similarity	NPC111275
0.8171	Intermediate Similarity	NPC234987
0.8158	Intermediate Similarity	NPC478158
0.8152	Intermediate Similarity	NPC262898
0.8128	Intermediate Similarity	NPC162730
0.8125	Intermediate Similarity	NPC55772
0.8111	Intermediate Similarity	NPC472323
0.8103	Intermediate Similarity	NPC281049
0.8098	Intermediate Similarity	NPC472293
0.8098	Intermediate Similarity	NPC179701
0.8095	Intermediate Similarity	NPC285469
0.8085	Intermediate Similarity	NPC165599
0.8079	Intermediate Similarity	NPC15840
0.8045	Intermediate Similarity	NPC258480
0.8045	Intermediate Similarity	NPC228835
0.8041	Intermediate Similarity	NPC477979
0.8032	Intermediate Similarity	NPC476874
0.8023	Intermediate Similarity	NPC11126
0.8023	Intermediate Similarity	NPC213468
0.8011	Intermediate Similarity	NPC17059
0.8	Intermediate Similarity	NPC325252
0.8	Intermediate Similarity	NPC472107
0.8	Intermediate Similarity	NPC472123
0.8	Intermediate Similarity	NPC277350
0.8	Intermediate Similarity	NPC79062
0.799	Intermediate Similarity	NPC475271
0.7968	Intermediate Similarity	NPC472297
0.7968	Intermediate Similarity	NPC472296
0.7956	Intermediate Similarity	NPC160381
0.7956	Intermediate Similarity	NPC315555
0.7956	Intermediate Similarity	NPC94752
0.7956	Intermediate Similarity	NPC66210
0.7949	Intermediate Similarity	NPC478157
0.7947	Intermediate Similarity	NPC473376
0.7939	Intermediate Similarity	NPC470440
0.7933	Intermediate Similarity	NPC113626
0.7933	Intermediate Similarity	NPC71037
0.7931	Intermediate Similarity	NPC317430
0.7927	Intermediate Similarity	NPC234999
0.7917	Intermediate Similarity	NPC266249
0.7914	Intermediate Similarity	NPC306376
0.7908	Intermediate Similarity	NPC36405
0.7907	Intermediate Similarity	NPC16667
0.7907	Intermediate Similarity	NPC282231
0.7903	Intermediate Similarity	NPC102592
0.7903	Intermediate Similarity	NPC79356
0.7901	Intermediate Similarity	NPC133003
0.7897	Intermediate Similarity	NPC54744
0.7897	Intermediate Similarity	NPC89508
0.7892	Intermediate Similarity	NPC88315
0.7889	Intermediate Similarity	NPC472108
0.7889	Intermediate Similarity	NPC139291
0.788	Intermediate Similarity	NPC472097
0.7874	Intermediate Similarity	NPC49954
0.7874	Intermediate Similarity	NPC474561
0.7874	Intermediate Similarity	NPC470509
0.7872	Intermediate Similarity	NPC241024
0.7869	Intermediate Similarity	NPC213629
0.7868	Intermediate Similarity	NPC312645
0.7865	Intermediate Similarity	NPC244741
0.7857	Intermediate Similarity	NPC478077
0.7849	Intermediate Similarity	NPC279918
0.7846	Intermediate Similarity	NPC475778
0.7835	Intermediate Similarity	NPC123839
0.7826	Intermediate Similarity	NPC198988
0.7824	Intermediate Similarity	NPC207726
0.7819	Intermediate Similarity	NPC171317
0.7778	Intermediate Similarity	NPC293917
0.7772	Intermediate Similarity	NPC477065
0.7771	Intermediate Similarity	NPC160105
0.7771	Intermediate Similarity	NPC54988
0.7747	Intermediate Similarity	NPC165495
0.7744	Intermediate Similarity	NPC88097
0.7739	Intermediate Similarity	NPC82070
0.773	Intermediate Similarity	NPC469501
0.773	Intermediate Similarity	NPC324091
0.773	Intermediate Similarity	NPC469470
0.7727	Intermediate Similarity	NPC63751
0.7727	Intermediate Similarity	NPC152768
0.7727	Intermediate Similarity	NPC148183
0.7727	Intermediate Similarity	NPC476114
0.7725	Intermediate Similarity	NPC67288
0.7723	Intermediate Similarity	NPC64216
0.7716	Intermediate Similarity	NPC234078
0.7716	Intermediate Similarity	NPC221100
0.7709	Intermediate Similarity	NPC151635
0.7692	Intermediate Similarity	NPC159125
0.7692	Intermediate Similarity	NPC472110
0.7692	Intermediate Similarity	NPC472104
0.7692	Intermediate Similarity	NPC472109
0.7692	Intermediate Similarity	NPC469358
0.7688	Intermediate Similarity	NPC243716
0.7688	Intermediate Similarity	NPC305984
0.7688	Intermediate Similarity	NPC117244
0.7688	Intermediate Similarity	NPC67056
0.7688	Intermediate Similarity	NPC473763
0.7684	Intermediate Similarity	NPC74413
0.7684	Intermediate Similarity	NPC280548
0.768	Intermediate Similarity	NPC54420
0.768	Intermediate Similarity	NPC270918
0.7677	Intermediate Similarity	NPC313640
0.7672	Intermediate Similarity	NPC469736
0.7672	Intermediate Similarity	NPC272483
0.7669	Intermediate Similarity	NPC218268
0.7665	Intermediate Similarity	NPC75634
0.7665	Intermediate Similarity	NPC207020
0.7657	Intermediate Similarity	NPC194640
0.7656	Intermediate Similarity	NPC260900
0.7656	Intermediate Similarity	NPC57398
0.7654	Intermediate Similarity	NPC189812
0.7654	Intermediate Similarity	NPC329688
0.7644	Intermediate Similarity	NPC315491
0.7644	Intermediate Similarity	NPC255229
0.7644	Intermediate Similarity	NPC470497
0.7644	Intermediate Similarity	NPC81229
0.7644	Intermediate Similarity	NPC45459
0.7632	Intermediate Similarity	NPC470499
0.763	Intermediate Similarity	NPC299594
0.7626	Intermediate Similarity	NPC229348
0.7619	Intermediate Similarity	NPC204141
0.7614	Intermediate Similarity	NPC82370
0.7614	Intermediate Similarity	NPC470508
0.7612	Intermediate Similarity	NPC52254
0.7602	Intermediate Similarity	NPC162860
0.7602	Intermediate Similarity	NPC469743
0.76	Intermediate Similarity	NPC194881
0.7598	Intermediate Similarity	NPC314603
0.7596	Intermediate Similarity	NPC470205
0.759	Intermediate Similarity	NPC115611
0.7579	Intermediate Similarity	NPC227582
0.7573	Intermediate Similarity	NPC33949
0.7572	Intermediate Similarity	NPC141353
0.7566	Intermediate Similarity	NPC474121
0.7566	Intermediate Similarity	NPC202812

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 NPC469896 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	495
0.2-0.3	960
0.3-0.4	1459
0.4-0.5	2524
0.5-0.6	2614
0.6-0.7	764
0.7-0.8	141
0.8-0.85	14
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8588	High Similarity	NPD482	Approved
0.8538	High Similarity	NPD749	Clinical (unspecified phase)
0.8427	Intermediate Similarity	NPD4499	Approved
0.8415	Intermediate Similarity	NPD4601	Approved
0.8415	Intermediate Similarity	NPD4600	Approved
0.84	Intermediate Similarity	NPD2092	Phase 2
0.84	Intermediate Similarity	NPD2095	Phase 2
0.84	Intermediate Similarity	NPD2094	Phase 2
0.84	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.8352	Intermediate Similarity	NPD2091	Phase 2
0.8352	Intermediate Similarity	NPD2096	Phase 2
0.8343	Intermediate Similarity	NPD4602	Approved
0.8315	Intermediate Similarity	NPD4501	Approved
0.8315	Intermediate Similarity	NPD4500	Approved
0.8314	Intermediate Similarity	NPD750	Phase 2
0.8035	Intermediate Similarity	NPD2844	Phase 3
0.8	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD2915	Discontinued
0.7884	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD5003	Discontinued
0.7795	Intermediate Similarity	NPD7470	Discontinued
0.7784	Intermediate Similarity	NPD4520	Approved
0.7778	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2564	Approved
0.773	Intermediate Similarity	NPD2565	Phase 2
0.7708	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD1325	Approved
0.7684	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD1326	Approved
0.7653	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD484	Approved
0.7614	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD5104	Approved
0.7592	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6595	Phase 3
0.7581	Intermediate Similarity	NPD1534	Approved
0.7577	Intermediate Similarity	NPD5901	Discontinued
0.7576	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD2144	Approved
0.7566	Intermediate Similarity	NPD7619	Phase 3
0.7566	Intermediate Similarity	NPD7618	Phase 3
0.7563	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD4397	Phase 1
0.7539	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7957	Phase 1
0.7529	Intermediate Similarity	NPD4326	Phase 2
0.7526	Intermediate Similarity	NPD8072	Approved
0.75	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD5426	Phase 3
0.7486	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD8073	Approved
0.7474	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD2510	Approved
0.7462	Intermediate Similarity	NPD2509	Approved
0.7459	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD3038	Discontinued
0.7442	Intermediate Similarity	NPD4463	Approved
0.7442	Intermediate Similarity	NPD4462	Approved
0.744	Intermediate Similarity	NPD1722	Approved
0.7435	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD8386	Phase 2
0.7425	Intermediate Similarity	NPD786	Approved
0.7419	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD8272	Phase 2
0.7387	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7865	Approved
0.7376	Intermediate Similarity	NPD3393	Approved
0.7376	Intermediate Similarity	NPD3389	Approved
0.7376	Intermediate Similarity	NPD3394	Approved
0.7374	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1683	Approved
0.7366	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7730	Approved
0.7356	Intermediate Similarity	NPD7731	Approved
0.7353	Intermediate Similarity	NPD6770	Approved
0.7347	Intermediate Similarity	NPD6176	Phase 1
0.7347	Intermediate Similarity	NPD2920	Discontinued
0.7346	Intermediate Similarity	NPD7952	Approved
0.7346	Intermediate Similarity	NPD7789	Approved
0.7346	Intermediate Similarity	NPD7790	Approved
0.7346	Intermediate Similarity	NPD7953	Approved
0.7346	Intermediate Similarity	NPD7950	Approved
0.7346	Intermediate Similarity	NPD7791	Approved
0.7346	Intermediate Similarity	NPD7951	Approved
0.7343	Intermediate Similarity	NPD7271	Approved
0.734	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD5818	Discontinued
0.7333	Intermediate Similarity	NPD7727	Phase 2
0.7327	Intermediate Similarity	NPD7970	Approved
0.7327	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5075	Discontinued
0.7323	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD5913	Phase 3
0.7312	Intermediate Similarity	NPD3320	Approved
0.7312	Intermediate Similarity	NPD3318	Approved
0.7312	Intermediate Similarity	NPD3319	Phase 1
0.7302	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4885	Approved
0.7297	Intermediate Similarity	NPD5473	Discontinued
0.7292	Intermediate Similarity	NPD7944	Discontinued
0.7286	Intermediate Similarity	NPD7824	Approved
0.7286	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6665	Discontinued
0.7273	Intermediate Similarity	NPD6178	Phase 3
0.7273	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD5065	Approved
0.7263	Intermediate Similarity	NPD5758	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD3178	Discontinued
0.725	Intermediate Similarity	NPD4506	Discontinued
0.7249	Intermediate Similarity	NPD8431	Approved
0.7249	Intermediate Similarity	NPD3961	Discontinued
0.7246	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD8322	Phase 2
0.7228	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8115	Approved
0.7222	Intermediate Similarity	NPD8114	Approved
0.722	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD5632	Approved
0.7216	Intermediate Similarity	NPD6664	Approved
0.7204	Intermediate Similarity	NPD6452	Discontinued
0.7196	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD1630	Approved
0.7191	Intermediate Similarity	NPD2213	Approved
0.7191	Intermediate Similarity	NPD2214	Approved
0.7189	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7864	Approved
0.7182	Intermediate Similarity	NPD7863	Approved
0.7167	Intermediate Similarity	NPD3583	Phase 2
0.7166	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4948	Discontinued
0.7157	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7817	Phase 1
0.7156	Intermediate Similarity	NPD7780	Approved
0.7156	Intermediate Similarity	NPD7781	Approved
0.7151	Intermediate Similarity	NPD5254	Discontinued
0.715	Intermediate Similarity	NPD1996	Discontinued
0.7149	Intermediate Similarity	NPD5482	Discontinued
0.7143	Intermediate Similarity	NPD7866	Approved
0.7143	Intermediate Similarity	NPD6249	Phase 2
0.7143	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6248	Phase 2
0.7136	Intermediate Similarity	NPD8098	Approved
0.7135	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5596	Phase 2
0.7128	Intermediate Similarity	NPD2880	Discontinued
0.712	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD5899	Approved
0.7112	Intermediate Similarity	NPD5898	Approved
0.7112	Intermediate Similarity	NPD5897	Approved
0.7108	Intermediate Similarity	NPD3243	Approved
0.7107	Intermediate Similarity	NPD6479	Discontinued
0.7105	Intermediate Similarity	NPD5809	Phase 3
0.71	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7482	Phase 2
0.709	Intermediate Similarity	NPD7483	Phase 2
0.7089	Intermediate Similarity	NPD7688	Phase 1
0.7086	Intermediate Similarity	NPD3100	Discontinued
0.7077	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5140	Approved
0.7072	Intermediate Similarity	NPD5138	Approved
0.7072	Intermediate Similarity	NPD1631	Approved
0.7062	Intermediate Similarity	NPD7603	Discontinued
0.7059	Intermediate Similarity	NPD4076	Approved
0.7059	Intermediate Similarity	NPD4079	Approved
0.7059	Intermediate Similarity	NPD7455	Approved
0.7059	Intermediate Similarity	NPD7454	Approved
0.7056	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6578	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7716	Approved
0.7048	Intermediate Similarity	NPD7717	Approved
0.7045	Intermediate Similarity	NPD3833	Phase 3
0.7045	Intermediate Similarity	NPD3835	Phase 3
0.7044	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD2381	Approved
0.7043	Intermediate Similarity	NPD2380	Approved
0.7043	Intermediate Similarity	NPD2382	Approved
0.7043	Intermediate Similarity	NPD4075	Phase 2
0.7037	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD1592	Phase 3
0.7035	Intermediate Similarity	NPD5020	Approved
0.7033	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7234	Approved
0.7031	Intermediate Similarity	NPD7233	Approved
0.7031	Intermediate Similarity	NPD4334	Discontinued

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