NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	160.06
Volume:	164.709
LogP:	1.123
LogD:	1.152
LogS:	-2.353
# Rotatable Bonds:	1
TPSA:	58.88
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.648
Synthetic Accessibility Score:	1.788
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.771
MDCK Permeability:	6.988887434999924e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.973
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.998
Plasma Protein Binding (PPB):	77.32878112792969%
Volume Distribution (VD):	1.2
Pgp-substrate:	39.19720458984375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.909
CYP1A2-substrate:	0.546
CYP2C19-inhibitor:	0.247
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.088
CYP2C9-substrate:	0.801
CYP2D6-inhibitor:	0.336
CYP2D6-substrate:	0.722
CYP3A4-inhibitor:	0.079
CYP3A4-substrate:	0.144

ADMET: Excretion

Clearance (CL):	8.603
Half-life (T1/2):	0.468

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.192
Drug-inuced Liver Injury (DILI):	0.754
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.831
Maximum Recommended Daily Dose:	0.276
Skin Sensitization:	0.195
Carcinogencity:	0.12
Eye Corrosion:	0.006
Eye Irritation:	0.946
Respiratory Toxicity:	0.292

Download Data

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

Natural Product: NPC131718

Natural Product ID:	NPC131718
*Common Name:**	Sid24824100
IUPAC Name:	1H-indole-3-carboxamide
Synonyms:	3-Indoleacetamide; Indole-3-Acetamide
Standard InCHIKey:	LSGKMZLPZFPAIN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H8N2O/c10-9(12)7-5-11-8-4-2-1-3-6(7)8/h1-5,11H,(H2,10,12)
SMILES:	OC(=N)c1c[nH]c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL379099
PubChem CID:	2192542
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002013] Indolecarboxylic acids and derivatives [CHEMONTID:0002014] Indolecarboxamides and derivatives

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678654]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787451]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	Roots	Anhui, China	n.a.	PMID[22694318]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Others	2
Potency	11

Activity Type	# Activity
Individual Protein	6
Organism	2
Others	3
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	14125.4	nM	PMID[536575]
NPT524	Individual Protein	Serine-protein kinase ATM	Homo sapiens	Potency	=	631.0	nM	PMID[536575]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	1636.0	nM	PMID[536575]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	29.1	nM	PMID[536575]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[536575]
NPT27	Others	Unspecified		LogP app	=	-5.21	n.a.	PMID[536574]
NPT35	Others	n.a.		LogP	=	0.75	n.a.	PMID[536574]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	26121.6	nM	PMID[536575]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PMID[536575]
NPT2	Others	Unspecified		Potency	=	461.1	nM	PMID[536575]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	1852.6	nM	PMID[536575]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	3.3	nM	PMID[536575]

☑ 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 NPC131718 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	638
0.1-0.2	7140
0.2-0.3	13212
0.3-0.4	14167
0.4-0.5	3377
0.5-0.6	1917
0.6-0.7	1520
0.7-0.8	576
0.8-0.85	106
0.85-0.9	26
0.9-0.95	16
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9733	High Similarity	NPC102423
0.9359	High Similarity	NPC313791
0.9252	High Similarity	NPC159856
0.915	High Similarity	NPC230869
0.9139	High Similarity	NPC469763
0.9139	High Similarity	NPC73952
0.9139	High Similarity	NPC259644
0.9139	High Similarity	NPC469786
0.9139	High Similarity	NPC469765
0.9139	High Similarity	NPC469760
0.9139	High Similarity	NPC25008
0.9079	High Similarity	NPC75540
0.9079	High Similarity	NPC212376
0.9079	High Similarity	NPC80597
0.9079	High Similarity	NPC70922
0.9079	High Similarity	NPC211572
0.902	High Similarity	NPC469785
0.9007	High Similarity	NPC24678
0.9007	High Similarity	NPC105818
0.8993	High Similarity	NPC314372
0.8986	High Similarity	NPC190296
0.8961	High Similarity	NPC469762
0.8957	High Similarity	NPC220765
0.8902	High Similarity	NPC204717
0.8855	High Similarity	NPC46580
0.8854	High Similarity	NPC311276
0.8848	High Similarity	NPC314002
0.8846	High Similarity	NPC279918
0.8841	High Similarity	NPC48938
0.8795	High Similarity	NPC171171
0.879	High Similarity	NPC282231
0.8774	High Similarity	NPC141353
0.8712	High Similarity	NPC184964
0.8707	High Similarity	NPC96102
0.8662	High Similarity	NPC135141
0.8662	High Similarity	NPC92796
0.8649	High Similarity	NPC105127
0.8649	High Similarity	NPC84911
0.8631	High Similarity	NPC278434
0.8627	High Similarity	NPC471957
0.8625	High Similarity	NPC54988
0.8625	High Similarity	NPC160105
0.8625	High Similarity	NPC474561
0.8625	High Similarity	NPC49954
0.8598	High Similarity	NPC96890
0.8581	High Similarity	NPC29886
0.8581	High Similarity	NPC261195
0.8571	High Similarity	NPC63751
0.8538	High Similarity	NPC99666
0.8533	High Similarity	NPC110126
0.8533	High Similarity	NPC73767
0.8528	High Similarity	NPC314603
0.85	High Similarity	NPC40779
0.8497	Intermediate Similarity	NPC242209
0.8485	Intermediate Similarity	NPC111275
0.8477	Intermediate Similarity	NPC469784
0.8477	Intermediate Similarity	NPC469779
0.8477	Intermediate Similarity	NPC279081
0.8477	Intermediate Similarity	NPC469780
0.8477	Intermediate Similarity	NPC469767
0.8477	Intermediate Similarity	NPC469783
0.8477	Intermediate Similarity	NPC469768
0.8477	Intermediate Similarity	NPC469761
0.8462	Intermediate Similarity	NPC216713
0.8457	Intermediate Similarity	NPC78020
0.8457	Intermediate Similarity	NPC201700
0.8435	Intermediate Similarity	NPC82295
0.843	Intermediate Similarity	NPC324149
0.8421	Intermediate Similarity	NPC469766
0.8395	Intermediate Similarity	NPC49217
0.8385	Intermediate Similarity	NPC476118
0.8385	Intermediate Similarity	NPC194640
0.8364	Intermediate Similarity	NPC149155
0.8364	Intermediate Similarity	NPC110500
0.8364	Intermediate Similarity	NPC203468
0.8355	Intermediate Similarity	NPC230002
0.8354	Intermediate Similarity	NPC470498
0.8343	Intermediate Similarity	NPC77555
0.8343	Intermediate Similarity	NPC156704
0.8343	Intermediate Similarity	NPC284678
0.8333	Intermediate Similarity	NPC71037
0.8323	Intermediate Similarity	NPC42979
0.8313	Intermediate Similarity	NPC267885
0.8313	Intermediate Similarity	NPC224764
0.8294	Intermediate Similarity	NPC188387
0.8294	Intermediate Similarity	NPC163421
0.8294	Intermediate Similarity	NPC15102
0.8293	Intermediate Similarity	NPC194411
0.8276	Intermediate Similarity	NPC106937
0.8276	Intermediate Similarity	NPC307963
0.8263	Intermediate Similarity	NPC151939
0.8263	Intermediate Similarity	NPC59269
0.8263	Intermediate Similarity	NPC248454
0.8256	Intermediate Similarity	NPC296527
0.8214	Intermediate Similarity	NPC126709
0.8214	Intermediate Similarity	NPC176199
0.8214	Intermediate Similarity	NPC248041
0.8214	Intermediate Similarity	NPC215795
0.8214	Intermediate Similarity	NPC283219
0.8208	Intermediate Similarity	NPC76748
0.8208	Intermediate Similarity	NPC83111
0.8205	Intermediate Similarity	NPC143872
0.8205	Intermediate Similarity	NPC288838
0.8202	Intermediate Similarity	NPC315491
0.8202	Intermediate Similarity	NPC45459
0.8182	Intermediate Similarity	NPC251090
0.8176	Intermediate Similarity	NPC200214
0.8176	Intermediate Similarity	NPC469358
0.8161	Intermediate Similarity	NPC92111
0.8161	Intermediate Similarity	NPC138370
0.8153	Intermediate Similarity	NPC469811
0.8144	Intermediate Similarity	NPC37423
0.8144	Intermediate Similarity	NPC275305
0.814	Intermediate Similarity	NPC315555
0.8125	Intermediate Similarity	NPC326634
0.8118	Intermediate Similarity	NPC233936
0.8107	Intermediate Similarity	NPC55772
0.8107	Intermediate Similarity	NPC72980
0.8107	Intermediate Similarity	NPC213468
0.8103	Intermediate Similarity	NPC95783
0.8101	Intermediate Similarity	NPC213308
0.8101	Intermediate Similarity	NPC321911
0.8101	Intermediate Similarity	NPC37548
0.809	Intermediate Similarity	NPC131887
0.8089	Intermediate Similarity	NPC63545
0.8084	Intermediate Similarity	NPC474409
0.8081	Intermediate Similarity	NPC280290
0.8079	Intermediate Similarity	NPC13880
0.807	Intermediate Similarity	NPC163055
0.8059	Intermediate Similarity	NPC300688
0.805	Intermediate Similarity	NPC53947
0.8047	Intermediate Similarity	NPC68354
0.8046	Intermediate Similarity	NPC32771
0.8038	Intermediate Similarity	NPC179787
0.8038	Intermediate Similarity	NPC201380
0.8025	Intermediate Similarity	NPC212742
0.8012	Intermediate Similarity	NPC317430
0.8	Intermediate Similarity	NPC154339
0.8	Intermediate Similarity	NPC470823
0.7989	Intermediate Similarity	NPC192315
0.7988	Intermediate Similarity	NPC150048
0.7988	Intermediate Similarity	NPC203754
0.7978	Intermediate Similarity	NPC222018
0.7976	Intermediate Similarity	NPC34508
0.7963	Intermediate Similarity	NPC285469
0.7962	Intermediate Similarity	NPC242556
0.795	Intermediate Similarity	NPC141926
0.795	Intermediate Similarity	NPC325903
0.7944	Intermediate Similarity	NPC476167
0.7941	Intermediate Similarity	NPC145885
0.7941	Intermediate Similarity	NPC14113
0.7941	Intermediate Similarity	NPC84827
0.7931	Intermediate Similarity	NPC235684
0.7931	Intermediate Similarity	NPC62749
0.7931	Intermediate Similarity	NPC94752
0.7923	Intermediate Similarity	NPC475070
0.7923	Intermediate Similarity	NPC470505
0.7923	Intermediate Similarity	NPC470500
0.7914	Intermediate Similarity	NPC129721
0.7907	Intermediate Similarity	NPC314394
0.7901	Intermediate Similarity	NPC38736
0.7901	Intermediate Similarity	NPC34844
0.7901	Intermediate Similarity	NPC470507
0.7889	Intermediate Similarity	NPC265576
0.7886	Intermediate Similarity	NPC317030
0.7881	Intermediate Similarity	NPC22079
0.7875	Intermediate Similarity	NPC187951
0.7865	Intermediate Similarity	NPC267343
0.7857	Intermediate Similarity	NPC218268
0.7857	Intermediate Similarity	NPC325252
0.7841	Intermediate Similarity	NPC213629
0.7841	Intermediate Similarity	NPC321708
0.7838	Intermediate Similarity	NPC88008
0.7831	Intermediate Similarity	NPC162268
0.7829	Intermediate Similarity	NPC474707
0.7821	Intermediate Similarity	NPC133366
0.7819	Intermediate Similarity	NPC128084
0.7816	Intermediate Similarity	NPC228835
0.7809	Intermediate Similarity	NPC477166
0.7809	Intermediate Similarity	NPC304187
0.7807	Intermediate Similarity	NPC5145
0.7805	Intermediate Similarity	NPC236711
0.7805	Intermediate Similarity	NPC216643
0.7805	Intermediate Similarity	NPC286427
0.7802	Intermediate Similarity	NPC470497
0.7802	Intermediate Similarity	NPC19872
0.7792	Intermediate Similarity	NPC198988
0.7791	Intermediate Similarity	NPC11126
0.7791	Intermediate Similarity	NPC88363
0.7791	Intermediate Similarity	NPC270009
0.779	Intermediate Similarity	NPC470499
0.7784	Intermediate Similarity	NPC204565
0.7772	Intermediate Similarity	NPC98715
0.7771	Intermediate Similarity	NPC476319
0.7771	Intermediate Similarity	NPC16667
0.7765	Intermediate Similarity	NPC474177
0.7764	Intermediate Similarity	NPC124005
0.776	Intermediate Similarity	NPC300183
0.7758	Intermediate Similarity	NPC56765
0.7758	Intermediate Similarity	NPC206819

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 NPC131718 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	713
0.2-0.3	773
0.3-0.4	1507
0.4-0.5	2666
0.5-0.6	2046
0.6-0.7	888
0.7-0.8	199
0.8-0.85	19
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9177	High Similarity	NPD5065	Approved
0.8707	High Similarity	NPD198	Clinical (unspecified phase)
0.8543	High Similarity	NPD1592	Phase 3
0.8533	High Similarity	NPD786	Approved
0.8519	High Similarity	NPD4184	Clinical (unspecified phase)
0.8519	High Similarity	NPD1326	Approved
0.8519	High Similarity	NPD1325	Approved
0.8488	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1722	Approved
0.8385	Intermediate Similarity	NPD5138	Approved
0.8385	Intermediate Similarity	NPD5140	Approved
0.8364	Intermediate Similarity	NPD482	Approved
0.8344	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1038	Approved
0.8276	Intermediate Similarity	NPD802	Phase 2
0.8239	Intermediate Similarity	NPD7948	Phase 1
0.8218	Intermediate Similarity	NPD3404	Approved
0.8202	Intermediate Similarity	NPD484	Approved
0.8176	Intermediate Similarity	NPD2095	Phase 2
0.8176	Intermediate Similarity	NPD2092	Phase 2
0.8176	Intermediate Similarity	NPD2094	Phase 2
0.8166	Intermediate Similarity	NPD6595	Phase 3
0.8165	Intermediate Similarity	NPD4462	Approved
0.8165	Intermediate Similarity	NPD4463	Approved
0.8155	Intermediate Similarity	NPD2144	Approved
0.8153	Intermediate Similarity	NPD4703	Approved
0.8153	Intermediate Similarity	NPD4702	Approved
0.8129	Intermediate Similarity	NPD2091	Phase 2
0.8129	Intermediate Similarity	NPD2096	Phase 2
0.8107	Intermediate Similarity	NPD4076	Approved
0.8107	Intermediate Similarity	NPD4079	Approved
0.8101	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD3100	Discontinued
0.807	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD2172	Phase 1
0.8047	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD3506	Approved
0.8047	Intermediate Similarity	NPD3505	Approved
0.8035	Intermediate Similarity	NPD706	Phase 1
0.8012	Intermediate Similarity	NPD3038	Discontinued
0.7977	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD750	Phase 2
0.7975	Intermediate Similarity	NPD5255	Approved
0.7943	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD5901	Discontinued
0.7888	Intermediate Similarity	NPD6158	Phase 2
0.7888	Intermediate Similarity	NPD2882	Phase 1
0.7888	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD8431	Approved
0.7879	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD3813	Approved
0.784	Intermediate Similarity	NPD2837	Discontinued
0.7838	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7819	Intermediate Similarity	NPD8093	Discontinued
0.7818	Intermediate Similarity	NPD1404	Approved
0.7818	Intermediate Similarity	NPD1403	Approved
0.7785	Intermediate Similarity	NPD3717	Discontinued
0.7778	Intermediate Similarity	NPD5100	Phase 3
0.7778	Intermediate Similarity	NPD2382	Approved
0.7778	Intermediate Similarity	NPD8094	Discontinued
0.7778	Intermediate Similarity	NPD2380	Approved
0.7778	Intermediate Similarity	NPD2381	Approved
0.7772	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD5596	Phase 2
0.7747	Intermediate Similarity	NPD3825	Phase 3
0.7725	Intermediate Similarity	NPD3330	Phase 1
0.7719	Intermediate Similarity	NPD4128	Approved
0.7706	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5117	Phase 2
0.7688	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD9080	Approved
0.7651	Intermediate Similarity	NPD704	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1392	Approved
0.7633	Intermediate Similarity	NPD2642	Approved
0.7633	Intermediate Similarity	NPD425	Approved
0.7633	Intermediate Similarity	NPD424	Approved
0.7633	Intermediate Similarity	NPD2639	Approved
0.763	Intermediate Similarity	NPD4181	Approved
0.7619	Intermediate Similarity	NPD3323	Discontinued
0.7606	Intermediate Similarity	NPD2509	Approved
0.7606	Intermediate Similarity	NPD2510	Approved
0.7604	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD5612	Discontinued
0.76	Intermediate Similarity	NPD3178	Discontinued
0.7593	Intermediate Similarity	NPD1661	Suspended
0.7588	Intermediate Similarity	NPD4639	Approved
0.7588	Intermediate Similarity	NPD2844	Phase 3
0.7588	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD4638	Approved
0.7588	Intermediate Similarity	NPD2640	Approved
0.7588	Intermediate Similarity	NPD2641	Approved
0.7588	Intermediate Similarity	NPD4640	Approved
0.7579	Intermediate Similarity	NPD5067	Phase 2
0.7579	Intermediate Similarity	NPD7470	Discontinued
0.7579	Intermediate Similarity	NPD5066	Phase 2
0.7574	Intermediate Similarity	NPD926	Approved
0.7574	Intermediate Similarity	NPD925	Approved
0.7572	Intermediate Similarity	NPD4075	Phase 2
0.7572	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD9284	Approved
0.7566	Intermediate Similarity	NPD991	Phase 2
0.756	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD5426	Phase 3
0.7527	Intermediate Similarity	NPD4999	Phase 3
0.7527	Intermediate Similarity	NPD4998	Phase 3
0.7514	Intermediate Similarity	NPD9690	Approved
0.7514	Intermediate Similarity	NPD6492	Phase 2
0.7513	Intermediate Similarity	NPD2189	Approved
0.7513	Intermediate Similarity	NPD2187	Approved
0.75	Intermediate Similarity	NPD1043	Phase 3
0.75	Intermediate Similarity	NPD112	Approved
0.75	Intermediate Similarity	NPD9705	Discontinued
0.75	Intermediate Similarity	NPD6281	Approved
0.7485	Intermediate Similarity	NPD2582	Approved
0.7485	Intermediate Similarity	NPD2581	Approved
0.7474	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4511	Phase 1
0.7471	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD8073	Approved
0.7425	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD4615	Phase 2
0.7418	Intermediate Similarity	NPD2127	Suspended
0.7409	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5254	Discontinued
0.7399	Intermediate Similarity	NPD3609	Approved
0.7399	Intermediate Similarity	NPD3610	Approved
0.7394	Intermediate Similarity	NPD4886	Phase 2
0.7394	Intermediate Similarity	NPD8072	Approved
0.7391	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3961	Discontinued
0.7385	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5862	Discovery
0.7377	Intermediate Similarity	NPD5428	Discontinued
0.7374	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2720	Phase 1
0.7368	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4865	Approved
0.7363	Intermediate Similarity	NPD4699	Discontinued
0.7358	Intermediate Similarity	NPD1262	Discovery
0.7355	Intermediate Similarity	NPD3654	Approved
0.7354	Intermediate Similarity	NPD8272	Phase 2
0.7346	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6452	Discontinued
0.7344	Intermediate Similarity	NPD3013	Phase 3
0.7344	Intermediate Similarity	NPD3014	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD3928	Approved
0.734	Intermediate Similarity	NPD3931	Approved
0.7333	Intermediate Similarity	NPD3389	Approved
0.7333	Intermediate Similarity	NPD3393	Approved
0.7333	Intermediate Similarity	NPD3394	Approved
0.7329	Intermediate Similarity	NPD1649	Discontinued
0.7318	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3475	Approved
0.7308	Intermediate Similarity	NPD3476	Approved
0.7303	Intermediate Similarity	NPD7867	Phase 1
0.7293	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4948	Discontinued
0.7288	Intermediate Similarity	NPD8386	Phase 2
0.7278	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6999	Discontinued
0.7273	Intermediate Similarity	NPD1768	Approved
0.7273	Intermediate Similarity	NPD3814	Phase 1
0.7273	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4547	Phase 3
0.7268	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD5913	Phase 3
0.7268	Intermediate Similarity	NPD1235	Phase 3
0.7264	Intermediate Similarity	NPD7603	Discontinued
0.725	Intermediate Similarity	NPD9506	Approved
0.7249	Intermediate Similarity	NPD6975	Discontinued
0.7247	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3262	Approved
0.7243	Intermediate Similarity	NPD7619	Phase 3
0.7243	Intermediate Similarity	NPD7618	Phase 3
0.7239	Intermediate Similarity	NPD2006	Phase 2
0.7239	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6217	Discontinued
0.7238	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2430	Phase 2
0.7226	Intermediate Similarity	NPD2118	Approved
0.7226	Intermediate Similarity	NPD2119	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