NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	240.09
Volume:	246.15
LogP:	2.486
LogD:	2.325
LogS:	-3.554
# Rotatable Bonds:	2
TPSA:	54.98
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.701
Synthetic Accessibility Score:	2.255
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.906
MDCK Permeability:	1.2365202564978972e-05
Pgp-inhibitor:	0.048
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.153

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.768
Plasma Protein Binding (PPB):	86.06880950927734%
Volume Distribution (VD):	1.121
Pgp-substrate:	12.308621406555176%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.81
CYP2C19-substrate:	0.415
CYP2C9-inhibitor:	0.406
CYP2C9-substrate:	0.932
CYP2D6-inhibitor:	0.788
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.787
CYP3A4-substrate:	0.271

ADMET: Excretion

Clearance (CL):	4.95
Half-life (T1/2):	0.374

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.921
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.902
Rat Oral Acute Toxicity:	0.972
Maximum Recommended Daily Dose:	0.868
Skin Sensitization:	0.705
Carcinogencity:	0.795
Eye Corrosion:	0.049
Eye Irritation:	0.961
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC122436

Natural Product ID:	NPC122436
*Common Name:**	Arenarine C
IUPAC Name:	1-(7-methoxy-9H-pyrido[3,4-b]indol-1-yl)ethanone
Synonyms:	Arenarine C
Standard InCHIKey:	SNGVLDNQSXBDPZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12N2O2/c1-8(17)13-14-11(5-6-15-13)10-4-3-9(18-2)7-12(10)16-14/h3-7,16H,1-2H3
SMILES:	CC(=O)c1c2c(ccn1)c1ccc(cc1[nH]2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1957115
PubChem CID:	188439
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
NPO13607	Arenaria kansuensis	Species	Scolopacidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17655145]
NPO503	Trigonostemon lii	Species	Euphorbiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22342628]
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28128938]
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6736972]
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22000	Artemisia schrenkiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13607	Arenaria kansuensis	Species	Scolopacidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22000	Artemisia schrenkiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22000	Artemisia schrenkiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13607	Arenaria kansuensis	Species	Scolopacidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO503	Trigonostemon lii	Species	Euphorbiaceae	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	9
Others	2

Activity Type	# Activity
Cell Line	8
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[490308]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[490308]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[490308]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[490308]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[490308]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[490309]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[490309]
NPT515	Cell Line	SGC-7901	Homo sapiens	IC50	>	10000.0	nM	PMID[490309]
NPT3114	Individual Protein	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Homo sapiens	Inhibition	=	92.0	%	PMID[490310]
NPT3114	Individual Protein	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Homo sapiens	Inhibition	=	85.0	%	PMID[490310]
NPT3114	Individual Protein	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Homo sapiens	IC50	=	66.7	nM	PMID[490310]

☑ 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 NPC122436 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	630
0.1-0.2	4325
0.2-0.3	12764
0.3-0.4	7263
0.4-0.5	12930
0.5-0.6	2075
0.6-0.7	2034
0.7-0.8	604
0.8-0.85	46
0.85-0.9	20
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.961	High Similarity	NPC260434
0.9474	High Similarity	NPC235685
0.9429	High Similarity	NPC101350
0.9083	High Similarity	NPC63971
0.9083	High Similarity	NPC91868
0.899	High Similarity	NPC232727
0.8942	High Similarity	NPC60621
0.8641	High Similarity	NPC167860
0.8641	High Similarity	NPC123976
0.8634	High Similarity	NPC266249
0.8626	High Similarity	NPC323969
0.8571	High Similarity	NPC27041
0.8552	High Similarity	NPC148889
0.8551	High Similarity	NPC123839
0.8502	High Similarity	NPC174758
0.8493	Intermediate Similarity	NPC182222
0.8473	Intermediate Similarity	NPC176538
0.8433	Intermediate Similarity	NPC471762
0.8428	Intermediate Similarity	NPC53534
0.8404	Intermediate Similarity	NPC213530
0.8404	Intermediate Similarity	NPC193267
0.8398	Intermediate Similarity	NPC285558
0.8391	Intermediate Similarity	NPC258048
0.8381	Intermediate Similarity	NPC118940
0.8293	Intermediate Similarity	NPC19872
0.8291	Intermediate Similarity	NPC152620
0.8265	Intermediate Similarity	NPC194740
0.8265	Intermediate Similarity	NPC66777
0.8263	Intermediate Similarity	NPC274982
0.8238	Intermediate Similarity	NPC174672
0.8235	Intermediate Similarity	NPC207686
0.823	Intermediate Similarity	NPC249583
0.823	Intermediate Similarity	NPC183777
0.823	Intermediate Similarity	NPC4687
0.8224	Intermediate Similarity	NPC305984
0.8221	Intermediate Similarity	NPC132539
0.8173	Intermediate Similarity	NPC476138
0.8173	Intermediate Similarity	NPC245816
0.8161	Intermediate Similarity	NPC97902
0.8157	Intermediate Similarity	NPC310118
0.8131	Intermediate Similarity	NPC191415
0.8079	Intermediate Similarity	NPC178858
0.8075	Intermediate Similarity	NPC87413
0.8072	Intermediate Similarity	NPC200553
0.8072	Intermediate Similarity	NPC196718
0.8072	Intermediate Similarity	NPC279189
0.8072	Intermediate Similarity	NPC102593
0.8066	Intermediate Similarity	NPC185782
0.805	Intermediate Similarity	NPC84478
0.8038	Intermediate Similarity	NPC295898
0.8037	Intermediate Similarity	NPC310211
0.8037	Intermediate Similarity	NPC308137
0.8029	Intermediate Similarity	NPC121772
0.8019	Intermediate Similarity	NPC82548
0.8018	Intermediate Similarity	NPC473041
0.801	Intermediate Similarity	NPC13880
0.8009	Intermediate Similarity	NPC322064
0.8	Intermediate Similarity	NPC476287
0.7981	Intermediate Similarity	NPC81535
0.7973	Intermediate Similarity	NPC157931
0.7973	Intermediate Similarity	NPC74575
0.7973	Intermediate Similarity	NPC478078
0.7973	Intermediate Similarity	NPC110151
0.7965	Intermediate Similarity	NPC162002
0.7963	Intermediate Similarity	NPC116238
0.7953	Intermediate Similarity	NPC26679
0.7944	Intermediate Similarity	NPC470020
0.7936	Intermediate Similarity	NPC303658
0.793	Intermediate Similarity	NPC472061
0.7926	Intermediate Similarity	NPC148183
0.7926	Intermediate Similarity	NPC152768
0.7926	Intermediate Similarity	NPC170114
0.792	Intermediate Similarity	NPC174489
0.7919	Intermediate Similarity	NPC229893
0.7919	Intermediate Similarity	NPC322482
0.7911	Intermediate Similarity	NPC49547
0.791	Intermediate Similarity	NPC102755
0.7902	Intermediate Similarity	NPC138370
0.79	Intermediate Similarity	NPC74360
0.7892	Intermediate Similarity	NPC296527
0.789	Intermediate Similarity	NPC169402
0.7885	Intermediate Similarity	NPC267928
0.7883	Intermediate Similarity	NPC21638
0.788	Intermediate Similarity	NPC470549
0.787	Intermediate Similarity	NPC264176
0.7857	Intermediate Similarity	NPC315957
0.7854	Intermediate Similarity	NPC247803
0.7854	Intermediate Similarity	NPC264285
0.7854	Intermediate Similarity	NPC46561
0.7854	Intermediate Similarity	NPC76748
0.7851	Intermediate Similarity	NPC26641
0.785	Intermediate Similarity	NPC287208
0.785	Intermediate Similarity	NPC39679
0.7848	Intermediate Similarity	NPC63109
0.7844	Intermediate Similarity	NPC8022
0.7844	Intermediate Similarity	NPC470799
0.7834	Intermediate Similarity	NPC236668
0.783	Intermediate Similarity	NPC53144
0.7826	Intermediate Similarity	NPC307963
0.7821	Intermediate Similarity	NPC165964
0.7818	Intermediate Similarity	NPC208084
0.7818	Intermediate Similarity	NPC288987
0.7816	Intermediate Similarity	NPC92111
0.7798	Intermediate Similarity	NPC477979
0.7798	Intermediate Similarity	NPC146976
0.7788	Intermediate Similarity	NPC219087
0.7783	Intermediate Similarity	NPC150239
0.7783	Intermediate Similarity	NPC284678
0.7783	Intermediate Similarity	NPC174760
0.7783	Intermediate Similarity	NPC37152
0.7778	Intermediate Similarity	NPC471304
0.7773	Intermediate Similarity	NPC240384
0.7773	Intermediate Similarity	NPC329747
0.7768	Intermediate Similarity	NPC470018
0.7757	Intermediate Similarity	NPC45190
0.7757	Intermediate Similarity	NPC300156
0.7756	Intermediate Similarity	NPC46580
0.7751	Intermediate Similarity	NPC251090
0.7748	Intermediate Similarity	NPC198503
0.7746	Intermediate Similarity	NPC134848
0.7746	Intermediate Similarity	NPC223427
0.7745	Intermediate Similarity	NPC26543
0.7742	Intermediate Similarity	NPC146418
0.7729	Intermediate Similarity	NPC473187
0.7729	Intermediate Similarity	NPC477549
0.7725	Intermediate Similarity	NPC78609
0.7721	Intermediate Similarity	NPC270918
0.7713	Intermediate Similarity	NPC16352
0.771	Intermediate Similarity	NPC472259
0.7706	Intermediate Similarity	NPC110182
0.7706	Intermediate Similarity	NPC316981
0.7703	Intermediate Similarity	NPC276657
0.7702	Intermediate Similarity	NPC270515
0.77	Intermediate Similarity	NPC57398
0.7699	Intermediate Similarity	NPC314954
0.7696	Intermediate Similarity	NPC11464
0.7696	Intermediate Similarity	NPC15801
0.7692	Intermediate Similarity	NPC324149
0.7689	Intermediate Similarity	NPC303374
0.7685	Intermediate Similarity	NPC171787
0.7682	Intermediate Similarity	NPC36405
0.7675	Intermediate Similarity	NPC469554
0.7671	Intermediate Similarity	NPC89508
0.7667	Intermediate Similarity	NPC79356
0.7667	Intermediate Similarity	NPC102592
0.7664	Intermediate Similarity	NPC165599
0.7661	Intermediate Similarity	NPC208284
0.7656	Intermediate Similarity	NPC326422
0.7655	Intermediate Similarity	NPC257851
0.765	Intermediate Similarity	NPC208522
0.7644	Intermediate Similarity	NPC179287
0.7639	Intermediate Similarity	NPC321428
0.7634	Intermediate Similarity	NPC210434
0.7634	Intermediate Similarity	NPC220851
0.763	Intermediate Similarity	NPC141454
0.7628	Intermediate Similarity	NPC470500
0.7619	Intermediate Similarity	NPC184680
0.7619	Intermediate Similarity	NPC131017
0.7615	Intermediate Similarity	NPC85273
0.7613	Intermediate Similarity	NPC96321
0.7611	Intermediate Similarity	NPC319232
0.7611	Intermediate Similarity	NPC24370
0.7604	Intermediate Similarity	NPC475910
0.7602	Intermediate Similarity	NPC3207
0.7598	Intermediate Similarity	NPC101543
0.7594	Intermediate Similarity	NPC306376
0.7593	Intermediate Similarity	NPC472064
0.7593	Intermediate Similarity	NPC472065
0.7591	Intermediate Similarity	NPC469592
0.7591	Intermediate Similarity	NPC471080
0.7586	Intermediate Similarity	NPC470784
0.7586	Intermediate Similarity	NPC470785
0.7581	Intermediate Similarity	NPC200836
0.7578	Intermediate Similarity	NPC292958
0.7578	Intermediate Similarity	NPC168209
0.7576	Intermediate Similarity	NPC295228
0.7571	Intermediate Similarity	NPC198673
0.7568	Intermediate Similarity	NPC312645
0.7565	Intermediate Similarity	NPC473105
0.7561	Intermediate Similarity	NPC176127
0.7559	Intermediate Similarity	NPC237414
0.7559	Intermediate Similarity	NPC476167
0.7559	Intermediate Similarity	NPC284338
0.7558	Intermediate Similarity	NPC193238
0.7556	Intermediate Similarity	NPC216612
0.7547	Intermediate Similarity	NPC106824
0.7547	Intermediate Similarity	NPC243834
0.7547	Intermediate Similarity	NPC70956
0.7546	Intermediate Similarity	NPC475070
0.7545	Intermediate Similarity	NPC472099
0.7545	Intermediate Similarity	NPC12344
0.7543	Intermediate Similarity	NPC470022
0.7534	Intermediate Similarity	NPC5145
0.7523	Intermediate Similarity	NPC330009
0.7521	Intermediate Similarity	NPC74619
0.7512	Intermediate Similarity	NPC175602
0.7512	Intermediate Similarity	NPC72211
0.7512	Intermediate Similarity	NPC474916
0.7512	Intermediate Similarity	NPC192315
0.7512	Intermediate Similarity	NPC154339

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 NPC122436 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	672
0.2-0.3	811
0.3-0.4	1537
0.4-0.5	2609
0.5-0.6	1950
0.6-0.7	1099
0.7-0.8	117
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8848	High Similarity	NPD2921	Clinical (unspecified phase)
0.8533	High Similarity	NPD5482	Discontinued
0.8438	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6242	Discontinued
0.8142	Intermediate Similarity	NPD6790	Phase 1
0.8101	Intermediate Similarity	NPD5450	Discontinued
0.8009	Intermediate Similarity	NPD4558	Phase 2
0.8009	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD4795	Phase 2
0.7857	Intermediate Similarity	NPD1740	Approved
0.7857	Intermediate Similarity	NPD1739	Approved
0.7854	Intermediate Similarity	NPD4429	Discontinued
0.785	Intermediate Similarity	NPD5658	Approved
0.7826	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1038	Approved
0.7812	Intermediate Similarity	NPD3259	Approved
0.7773	Intermediate Similarity	NPD5632	Approved
0.7767	Intermediate Similarity	NPD2509	Approved
0.7767	Intermediate Similarity	NPD2510	Approved
0.7763	Intermediate Similarity	NPD3393	Approved
0.7763	Intermediate Similarity	NPD3389	Approved
0.7763	Intermediate Similarity	NPD3394	Approved
0.7746	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD4952	Phase 3
0.7652	Intermediate Similarity	NPD3006	Discontinued
0.7602	Intermediate Similarity	NPD2412	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD4373	Phase 2
0.7558	Intermediate Similarity	NPD1392	Approved
0.7557	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD8091	Phase 3
0.7522	Intermediate Similarity	NPD4885	Approved
0.7521	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD5022	Discontinued
0.7511	Intermediate Similarity	NPD5479	Discontinued
0.75	Intermediate Similarity	NPD7994	Phase 2
0.7489	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD7558	Phase 2
0.7477	Intermediate Similarity	NPD5293	Phase 2
0.7455	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD484	Approved
0.7418	Intermediate Similarity	NPD6228	Discontinued
0.7411	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7406	Intermediate Similarity	NPD802	Phase 2
0.7401	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD3825	Phase 3
0.7389	Intermediate Similarity	NPD1996	Discontinued
0.738	Intermediate Similarity	NPD7426	Phase 1
0.7366	Intermediate Similarity	NPD5612	Discontinued
0.7352	Intermediate Similarity	NPD3003	Approved
0.7349	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6531	Approved
0.7347	Intermediate Similarity	NPD6530	Approved
0.7339	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD4368	Phase 2
0.7316	Intermediate Similarity	NPD5559	Phase 2
0.7315	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7309	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2951	Discontinued
0.7306	Intermediate Similarity	NPD3947	Discontinued
0.7304	Intermediate Similarity	NPD7603	Discontinued
0.729	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2187	Approved
0.7285	Intermediate Similarity	NPD2189	Approved
0.7284	Intermediate Similarity	NPD2311	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7853	Phase 2
0.7273	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD5066	Phase 2
0.7265	Intermediate Similarity	NPD5067	Phase 2
0.7265	Intermediate Similarity	NPD4850	Phase 1
0.7265	Intermediate Similarity	NPD5475	Discontinued
0.7253	Intermediate Similarity	NPD6962	Phase 2
0.7249	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1768	Approved
0.7234	Intermediate Similarity	NPD6963	Approved
0.7234	Intermediate Similarity	NPD6964	Approved
0.7232	Intermediate Similarity	NPD7069	Discontinued
0.7229	Intermediate Similarity	NPD7803	Approved
0.7227	Intermediate Similarity	NPD5901	Discontinued
0.7222	Intermediate Similarity	NPD7948	Phase 1
0.721	Intermediate Similarity	NPD8512	Phase 3
0.7198	Intermediate Similarity	NPD4845	Discontinued
0.7196	Intermediate Similarity	NPD3923	Approved
0.7196	Intermediate Similarity	NPD3922	Approved
0.7196	Intermediate Similarity	NPD3924	Approved
0.7196	Intermediate Similarity	NPD3921	Approved
0.7195	Intermediate Similarity	NPD5601	Phase 2
0.7188	Intermediate Similarity	NPD5416	Discontinued
0.7166	Intermediate Similarity	NPD7955	Approved
0.7166	Intermediate Similarity	NPD7956	Approved
0.7156	Intermediate Similarity	NPD4889	Approved
0.7154	Intermediate Similarity	NPD5509	Phase 1
0.7154	Intermediate Similarity	NPD8049	Phase 2
0.7149	Intermediate Similarity	NPD3354	Phase 2
0.7137	Intermediate Similarity	NPD1659	Phase 1
0.713	Intermediate Similarity	NPD4418	Discontinued
0.7124	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6172	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD2471	Approved
0.7119	Intermediate Similarity	NPD2472	Approved
0.7119	Intermediate Similarity	NPD4369	Phase 2
0.7118	Intermediate Similarity	NPD7194	Discontinued
0.7111	Intermediate Similarity	NPD7470	Discontinued
0.7104	Intermediate Similarity	NPD5513	Phase 2
0.7093	Intermediate Similarity	NPD5903	Approved
0.7093	Intermediate Similarity	NPD5902	Approved
0.7093	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7689	Approved
0.7083	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD3815	Phase 1
0.708	Intermediate Similarity	NPD3816	Phase 1
0.7078	Intermediate Similarity	NPD4548	Discontinued
0.7073	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD3397	Phase 2
0.7069	Intermediate Similarity	NPD6306	Phase 2
0.7069	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD5116	Phase 1
0.7068	Intermediate Similarity	NPD7708	Approved
0.7068	Intermediate Similarity	NPD5867	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6968	Phase 2
0.7064	Intermediate Similarity	NPD6969	Phase 2
0.7061	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6473	Phase 1
0.7051	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3945	Discontinued
0.7048	Intermediate Similarity	NPD3795	Approved
0.7048	Intermediate Similarity	NPD3794	Approved
0.7042	Intermediate Similarity	NPD1927	Discontinued
0.704	Intermediate Similarity	NPD8403	Phase 1
0.7037	Intermediate Similarity	NPD4372	Phase 1
0.7037	Intermediate Similarity	NPD5488	Discontinued
0.7037	Intermediate Similarity	NPD6569	Phase 2
0.7036	Intermediate Similarity	NPD7925	Phase 2
0.7036	Intermediate Similarity	NPD7924	Phase 2
0.7031	Intermediate Similarity	NPD4989	Phase 2
0.7029	Intermediate Similarity	NPD946	Discontinued
0.7027	Intermediate Similarity	NPD6176	Phase 1
0.7025	Intermediate Similarity	NPD7067	Approved
0.7025	Intermediate Similarity	NPD7068	Approved
0.7022	Intermediate Similarity	NPD4506	Discontinued
0.7019	Intermediate Similarity	NPD482	Approved
0.7018	Intermediate Similarity	NPD5512	Phase 3
0.7014	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5930	Phase 3
0.7009	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD8358	Approved
0.7005	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD3960	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD5866	Approved
0.7	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6568	Discontinued
0.6983	Remote Similarity	NPD4923	Phase 1
0.6982	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6376	Discontinued
0.6977	Remote Similarity	NPD7198	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6494	Phase 2
0.697	Remote Similarity	NPD7404	Approved
0.697	Remote Similarity	NPD3402	Phase 1
0.697	Remote Similarity	NPD6770	Approved
0.6968	Remote Similarity	NPD4500	Approved
0.6968	Remote Similarity	NPD4501	Approved
0.6966	Remote Similarity	NPD1258	Discontinued
0.6964	Remote Similarity	NPD3507	Phase 2
0.6959	Remote Similarity	NPD4376	Phase 3
0.6957	Remote Similarity	NPD8284	Discontinued
0.6955	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6961	Discontinued
0.6948	Remote Similarity	NPD3569	Discontinued
0.6943	Remote Similarity	NPD3257	Approved
0.6936	Remote Similarity	NPD8289	Discontinued
0.6934	Remote Similarity	NPD4204	Approved
0.6934	Remote Similarity	NPD4203	Approved
0.6933	Remote Similarity	NPD7222	Phase 2
0.693	Remote Similarity	NPD4948	Discontinued
0.6917	Remote Similarity	NPD1259	Discontinued
0.6908	Remote Similarity	NPD8246	Approved
0.6908	Remote Similarity	NPD8247	Approved
0.6903	Remote Similarity	NPD7467	Discontinued
0.6901	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD3396	Approved
0.6895	Remote Similarity	NPD3395	Approved
0.6894	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5530	Phase 1
0.6889	Remote Similarity	NPD2008	Discontinued
0.688	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD8479	Phase 2
0.6866	Remote Similarity	NPD4499	Approved
0.6864	Remote Similarity	NPD3263	Phase 3
0.686	Remote Similarity	NPD4313	Approved
0.686	Remote Similarity	NPD4314	Approved
0.686	Remote Similarity	NPD5018	Phase 3
0.6857	Remote Similarity	NPD5065	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