NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.07
Volume:	266.912
LogP:	3.03
LogD:	2.731
LogS:	-4.653
# Rotatable Bonds:	1
TPSA:	65.45
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.707
Synthetic Accessibility Score:	2.512
Fsp3:	0.0
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:	-4.947
MDCK Permeability:	1.577153852849733e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.627

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.348
Plasma Protein Binding (PPB):	98.7383041381836%
Volume Distribution (VD):	0.367
Pgp-substrate:	1.1607297658920288%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.808
CYP2C19-inhibitor:	0.365
CYP2C19-substrate:	0.081
CYP2C9-inhibitor:	0.609
CYP2C9-substrate:	0.799
CYP2D6-inhibitor:	0.558
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.448
CYP3A4-substrate:	0.355

ADMET: Excretion

Clearance (CL):	0.795
Half-life (T1/2):	0.135

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.699
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.341
Rat Oral Acute Toxicity:	0.619
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.37
Carcinogencity:	0.539
Eye Corrosion:	0.003
Eye Irritation:	0.72
Respiratory Toxicity:	0.652

Download Data

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

Natural Product: NPC237649

Natural Product ID:	NPC237649
*Common Name:**	3-(3-Oxo-1H-Indol-2-Ylidene)-1H-Indol-2-One
IUPAC Name:	3-(3-oxo-1H-indol-2-ylidene)-1H-indol-2-one
Synonyms:
Standard InCHIKey:	CRDNMYFJWFXOCH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H10N2O2/c19-15-10-6-2-4-8-12(10)17-14(15)13-9-5-1-3-7-11(9)18-16(13)20/h1-8,17H,(H,18,20)
SMILES:	c1ccc2c(c1)C(=C1C(=O)c3ccccc3N1)C(=N2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3185783
PubChem CID:	5380743
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001146] Indolines

*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
NPO22457	Swertia calycina	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/cbdv.200490123]
NPO22457	Swertia calycina	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22457	Swertia calycina	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22457	Swertia calycina	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22457	Swertia calycina	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23820	Indigofera suffruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23903	Senecio glanduloso-pilosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Potency	4

Activity Type	# Activity
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	421.4	nM	PMID[534851]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	18.8	nM	PMID[534851]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	14950.2	nM	PMID[534851]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	66.8	nM	PMID[534851]

☑ 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 NPC237649 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	263
0.1-0.2	2172
0.2-0.3	10046
0.3-0.4	10807
0.4-0.5	14062
0.5-0.6	4487
0.6-0.7	784
0.7-0.8	72
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC300596
0.8429	Intermediate Similarity	NPC209389
0.8255	Intermediate Similarity	NPC136002
0.8054	Intermediate Similarity	NPC471574
0.7862	Intermediate Similarity	NPC194562
0.7834	Intermediate Similarity	NPC295021
0.7817	Intermediate Similarity	NPC254698
0.7815	Intermediate Similarity	NPC43477
0.777	Intermediate Similarity	NPC253476
0.7763	Intermediate Similarity	NPC472241
0.7738	Intermediate Similarity	NPC475685
0.7665	Intermediate Similarity	NPC471743
0.7632	Intermediate Similarity	NPC207554
0.7632	Intermediate Similarity	NPC472243
0.7622	Intermediate Similarity	NPC268534
0.7613	Intermediate Similarity	NPC472242
0.7606	Intermediate Similarity	NPC179605
0.7606	Intermediate Similarity	NPC279385
0.7605	Intermediate Similarity	NPC475594
0.7593	Intermediate Similarity	NPC27904
0.7574	Intermediate Similarity	NPC475761
0.7571	Intermediate Similarity	NPC147957
0.756	Intermediate Similarity	NPC475607
0.7552	Intermediate Similarity	NPC103292
0.7517	Intermediate Similarity	NPC192533
0.7515	Intermediate Similarity	NPC474081
0.7471	Intermediate Similarity	NPC474041
0.7468	Intermediate Similarity	NPC471164
0.7439	Intermediate Similarity	NPC476231
0.7439	Intermediate Similarity	NPC88970
0.7421	Intermediate Similarity	NPC144691
0.7414	Intermediate Similarity	NPC150308
0.7394	Intermediate Similarity	NPC189116
0.7361	Intermediate Similarity	NPC130931
0.7349	Intermediate Similarity	NPC471130
0.7333	Intermediate Similarity	NPC316746
0.733	Intermediate Similarity	NPC221873
0.7321	Intermediate Similarity	NPC471943
0.7321	Intermediate Similarity	NPC472118
0.731	Intermediate Similarity	NPC257490
0.7285	Intermediate Similarity	NPC40364
0.7267	Intermediate Similarity	NPC472245
0.7267	Intermediate Similarity	NPC475094
0.726	Intermediate Similarity	NPC39818
0.7255	Intermediate Similarity	NPC173295
0.7248	Intermediate Similarity	NPC58827
0.7248	Intermediate Similarity	NPC307437
0.7248	Intermediate Similarity	NPC72473
0.7244	Intermediate Similarity	NPC316202
0.7233	Intermediate Similarity	NPC259678
0.7215	Intermediate Similarity	NPC470822
0.7215	Intermediate Similarity	NPC130797
0.7202	Intermediate Similarity	NPC182131
0.72	Intermediate Similarity	NPC150863
0.72	Intermediate Similarity	NPC471742
0.7193	Intermediate Similarity	NPC470548
0.7179	Intermediate Similarity	NPC242933
0.7175	Intermediate Similarity	NPC473815
0.7174	Intermediate Similarity	NPC471944
0.7172	Intermediate Similarity	NPC177684
0.7172	Intermediate Similarity	NPC291962
0.7166	Intermediate Similarity	NPC471155
0.7143	Intermediate Similarity	NPC117027
0.7143	Intermediate Similarity	NPC470317
0.7134	Intermediate Similarity	NPC2823
0.7128	Intermediate Similarity	NPC270241
0.7126	Intermediate Similarity	NPC472121
0.7123	Intermediate Similarity	NPC161956
0.7123	Intermediate Similarity	NPC258531
0.7123	Intermediate Similarity	NPC112373
0.7115	Intermediate Similarity	NPC181527
0.7112	Intermediate Similarity	NPC225400
0.7079	Intermediate Similarity	NPC278434
0.7078	Intermediate Similarity	NPC184437
0.7076	Intermediate Similarity	NPC355
0.7074	Intermediate Similarity	NPC470786
0.7074	Intermediate Similarity	NPC472538
0.707	Intermediate Similarity	NPC315051
0.7066	Intermediate Similarity	NPC322644
0.7051	Intermediate Similarity	NPC122553
0.705	Intermediate Similarity	NPC172170
0.7045	Intermediate Similarity	NPC243058
0.7044	Intermediate Similarity	NPC314287
0.7041	Intermediate Similarity	NPC115232
0.7039	Intermediate Similarity	NPC314431
0.7039	Intermediate Similarity	NPC280807
0.7035	Intermediate Similarity	NPC177261
0.7033	Intermediate Similarity	NPC202812
0.7032	Intermediate Similarity	NPC300299
0.7019	Intermediate Similarity	NPC478039
0.7019	Intermediate Similarity	NPC146370
0.7012	Intermediate Similarity	NPC117032
0.7011	Intermediate Similarity	NPC219848
0.7011	Intermediate Similarity	NPC284775
0.7006	Intermediate Similarity	NPC203635
0.7	Intermediate Similarity	NPC154339
0.6995	Remote Similarity	NPC472540
0.6995	Remote Similarity	NPC472539
0.6995	Remote Similarity	NPC470787
0.6986	Remote Similarity	NPC229353
0.6982	Remote Similarity	NPC204867
0.6974	Remote Similarity	NPC122235
0.6971	Remote Similarity	NPC256268
0.6962	Remote Similarity	NPC47986
0.6957	Remote Similarity	NPC472542
0.6957	Remote Similarity	NPC472541
0.6944	Remote Similarity	NPC473666
0.6936	Remote Similarity	NPC252572
0.6933	Remote Similarity	NPC226794
0.6928	Remote Similarity	NPC114808
0.6928	Remote Similarity	NPC477432
0.6927	Remote Similarity	NPC90415
0.6923	Remote Similarity	NPC67551
0.6919	Remote Similarity	NPC131887
0.6906	Remote Similarity	NPC313293
0.6905	Remote Similarity	NPC36495
0.6905	Remote Similarity	NPC103250
0.6887	Remote Similarity	NPC205946
0.6885	Remote Similarity	NPC267343
0.6883	Remote Similarity	NPC314098
0.6882	Remote Similarity	NPC138293
0.6882	Remote Similarity	NPC113056
0.6865	Remote Similarity	NPC141454
0.6864	Remote Similarity	NPC93653
0.6859	Remote Similarity	NPC162417
0.6859	Remote Similarity	NPC316104
0.6857	Remote Similarity	NPC151635
0.6854	Remote Similarity	NPC471785
0.6851	Remote Similarity	NPC18890
0.6845	Remote Similarity	NPC211525
0.6845	Remote Similarity	NPC153694
0.6842	Remote Similarity	NPC52059
0.6842	Remote Similarity	NPC470069
0.6839	Remote Similarity	NPC476687
0.6839	Remote Similarity	NPC476685
0.6839	Remote Similarity	NPC476689
0.6837	Remote Similarity	NPC27041
0.6836	Remote Similarity	NPC283810
0.6835	Remote Similarity	NPC287358
0.6835	Remote Similarity	NPC159722
0.6828	Remote Similarity	NPC470550
0.6825	Remote Similarity	NPC295548
0.6824	Remote Similarity	NPC226143
0.6824	Remote Similarity	NPC214106
0.6821	Remote Similarity	NPC317758
0.6813	Remote Similarity	NPC471196
0.6813	Remote Similarity	NPC471195
0.6796	Remote Similarity	NPC206186
0.679	Remote Similarity	NPC314186
0.6788	Remote Similarity	NPC13526
0.6786	Remote Similarity	NPC322064
0.6784	Remote Similarity	NPC476118
0.6782	Remote Similarity	NPC469671
0.6782	Remote Similarity	NPC126676
0.6779	Remote Similarity	NPC150323
0.6776	Remote Similarity	NPC470343
0.6776	Remote Similarity	NPC92803
0.6776	Remote Similarity	NPC472244
0.6763	Remote Similarity	NPC178681
0.6748	Remote Similarity	NPC119569
0.6738	Remote Similarity	NPC474916
0.6737	Remote Similarity	NPC134848
0.6737	Remote Similarity	NPC98715
0.6737	Remote Similarity	NPC165599
0.6734	Remote Similarity	NPC276657
0.6731	Remote Similarity	NPC207428
0.6725	Remote Similarity	NPC293458
0.6719	Remote Similarity	NPC244741
0.6716	Remote Similarity	NPC229893
0.6707	Remote Similarity	NPC324445
0.6706	Remote Similarity	NPC243673
0.6706	Remote Similarity	NPC63210
0.6706	Remote Similarity	NPC310403
0.6706	Remote Similarity	NPC263709
0.6706	Remote Similarity	NPC148468
0.6706	Remote Similarity	NPC97380
0.6702	Remote Similarity	NPC132539
0.6702	Remote Similarity	NPC106118
0.669	Remote Similarity	NPC37584
0.6688	Remote Similarity	NPC476950
0.6687	Remote Similarity	NPC473804
0.6687	Remote Similarity	NPC241392
0.6687	Remote Similarity	NPC83214
0.6687	Remote Similarity	NPC472103
0.6686	Remote Similarity	NPC313757
0.6686	Remote Similarity	NPC84317
0.6686	Remote Similarity	NPC318183
0.6686	Remote Similarity	NPC292265
0.6686	Remote Similarity	NPC6982
0.6685	Remote Similarity	NPC49184
0.6685	Remote Similarity	NPC476460
0.6685	Remote Similarity	NPC138370
0.6667	Remote Similarity	NPC157828
0.6667	Remote Similarity	NPC143457
0.6667	Remote Similarity	NPC195239
0.6648	Remote Similarity	NPC160381
0.6633	Remote Similarity	NPC248601
0.6633	Remote Similarity	NPC110182
0.6632	Remote Similarity	NPC270918
0.6632	Remote Similarity	NPC46225

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 NPC237649 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	592
0.2-0.3	937
0.3-0.4	934
0.4-0.5	3286
0.5-0.6	2698
0.6-0.7	489
0.7-0.8	35
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7947	Intermediate Similarity	NPD1625	Approved
0.7902	Intermediate Similarity	NPD1593	Approved
0.7881	Intermediate Similarity	NPD1189	Approved
0.7806	Intermediate Similarity	NPD4888	Discontinued
0.7727	Intermediate Similarity	NPD6017	Discontinued
0.7682	Intermediate Similarity	NPD1626	Approved
0.759	Intermediate Similarity	NPD3776	Discontinued
0.7532	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1230	Approved
0.7467	Intermediate Similarity	NPD1541	Approved
0.7466	Intermediate Similarity	NPD1574	Approved
0.7438	Intermediate Similarity	NPD1854	Approved
0.7425	Intermediate Similarity	NPD2369	Discontinued
0.7412	Intermediate Similarity	NPD3755	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2844	Phase 3
0.7345	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6506	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7570	Approved
0.7303	Intermediate Similarity	NPD7569	Approved
0.7261	Intermediate Similarity	NPD1592	Phase 3
0.7261	Intermediate Similarity	NPD4464	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6163	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2470	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1874	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1527	Phase 2
0.7195	Intermediate Similarity	NPD951	Approved
0.7195	Intermediate Similarity	NPD2836	Approved
0.7161	Intermediate Similarity	NPD4077	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1228	Phase 2
0.7143	Intermediate Similarity	NPD979	Approved
0.7143	Intermediate Similarity	NPD4161	Discontinued
0.7134	Intermediate Similarity	NPD9477	Approved
0.7126	Intermediate Similarity	NPD1210	Approved
0.7126	Intermediate Similarity	NPD5445	Approved
0.7111	Intermediate Similarity	NPD5937	Approved
0.7105	Intermediate Similarity	NPD1619	Phase 3
0.7089	Intermediate Similarity	NPD2365	Approved
0.7079	Intermediate Similarity	NPD4948	Discontinued
0.7073	Intermediate Similarity	NPD5086	Approved
0.7066	Intermediate Similarity	NPD4311	Approved
0.7044	Intermediate Similarity	NPD2820	Phase 3
0.7025	Intermediate Similarity	NPD3434	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1575	Approved
0.7018	Intermediate Similarity	NPD1573	Approved
0.7012	Intermediate Similarity	NPD3248	Phase 1
0.6994	Remote Similarity	NPD5748	Phase 2
0.6993	Remote Similarity	NPD1175	Approved
0.6993	Remote Similarity	NPD486	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7105	Phase 1
0.6982	Remote Similarity	NPD1631	Approved
0.697	Remote Similarity	NPD2790	Discontinued
0.6962	Remote Similarity	NPD1205	Approved
0.6962	Remote Similarity	NPD1209	Approved
0.6954	Remote Similarity	NPD1544	Phase 1
0.6948	Remote Similarity	NPD1920	Approved
0.6948	Remote Similarity	NPD1919	Approved
0.6943	Remote Similarity	NPD1532	Approved
0.6943	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2331	Discontinued
0.6923	Remote Similarity	NPD2791	Discontinued
0.6914	Remote Similarity	NPD3792	Approved
0.691	Remote Similarity	NPD5923	Phase 1
0.6905	Remote Similarity	NPD4393	Approved
0.6905	Remote Similarity	NPD33	Approved
0.6897	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5466	Approved
0.6886	Remote Similarity	NPD1211	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1208	Approved
0.6875	Remote Similarity	NPD1908	Phase 2
0.6872	Remote Similarity	NPD6557	Phase 2
0.6863	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1079	Discontinued
0.6845	Remote Similarity	NPD212	Discontinued
0.6836	Remote Similarity	NPD4329	Approved
0.6836	Remote Similarity	NPD4330	Approved
0.6835	Remote Similarity	NPD6342	Discontinued
0.6832	Remote Similarity	NPD5024	Approved
0.6826	Remote Similarity	NPD1514	Discontinued
0.6805	Remote Similarity	NPD1630	Approved
0.6795	Remote Similarity	NPD1595	Approved
0.6795	Remote Similarity	NPD1594	Phase 3
0.6784	Remote Similarity	NPD5138	Approved
0.6784	Remote Similarity	NPD5140	Approved
0.6782	Remote Similarity	NPD1913	Phase 1
0.678	Remote Similarity	NPD3782	Discontinued
0.6779	Remote Similarity	NPD9272	Approved
0.6776	Remote Similarity	NPD5076	Approved
0.6776	Remote Similarity	NPD5077	Approved
0.6776	Remote Similarity	NPD5042	Phase 1
0.6774	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1206	Approved
0.6772	Remote Similarity	NPD1207	Approved
0.6763	Remote Similarity	NPD2404	Discontinued
0.6763	Remote Similarity	NPD2037	Approved
0.6752	Remote Similarity	NPD1531	Approved
0.6744	Remote Similarity	NPD5430	Discontinued
0.6738	Remote Similarity	NPD5856	Discontinued
0.6728	Remote Similarity	NPD6301	Phase 2
0.6728	Remote Similarity	NPD4430	Phase 2
0.6726	Remote Similarity	NPD7072	Phase 2
0.6724	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD4412	Phase 2
0.671	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.669	Remote Similarity	NPD181	Approved
0.6687	Remote Similarity	NPD5918	Discontinued
0.6686	Remote Similarity	NPD3790	Phase 2
0.6686	Remote Similarity	NPD2432	Approved
0.6686	Remote Similarity	NPD2431	Approved
0.6685	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1553	Approved
0.6667	Remote Similarity	NPD168	Phase 1
0.6667	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3229	Phase 2
0.6667	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2360	Approved
0.6667	Remote Similarity	NPD167	Phase 2
0.6648	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1168	Approved
0.6646	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD1839	Phase 1
0.6629	Remote Similarity	NPD5498	Phase 2
0.6627	Remote Similarity	NPD4432	Discontinued
0.6627	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD3947	Discontinued
0.6615	Remote Similarity	NPD5901	Discontinued
0.6612	Remote Similarity	NPD6483	Approved
0.6612	Remote Similarity	NPD6484	Approved
0.6611	Remote Similarity	NPD5637	Discontinued
0.6611	Remote Similarity	NPD3990	Phase 3
0.661	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD4514	Approved
0.6606	Remote Similarity	NPD1524	Phase 1
0.6605	Remote Similarity	NPD3625	Discontinued
0.66	Remote Similarity	NPD2212	Approved
0.66	Remote Similarity	NPD2210	Approved
0.6598	Remote Similarity	NPD2509	Approved
0.6598	Remote Similarity	NPD2510	Approved
0.6592	Remote Similarity	NPD1587	Approved
0.6588	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7091	Discontinued
0.6588	Remote Similarity	NPD2672	Discontinued
0.6582	Remote Similarity	NPD2949	Approved
0.6582	Remote Similarity	NPD5416	Discontinued
0.6582	Remote Similarity	NPD2950	Approved
0.6579	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3004	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD2821	Approved
0.6571	Remote Similarity	NPD2455	Approved
0.6571	Remote Similarity	NPD2454	Approved
0.657	Remote Similarity	NPD2506	Approved
0.6564	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6768	Approved
0.6562	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD1036	Approved
0.6556	Remote Similarity	NPD3989	Phase 3
0.6548	Remote Similarity	NPD5982	Phase 2
0.6543	Remote Similarity	NPD3391	Approved
0.6538	Remote Similarity	NPD1781	Discontinued
0.6534	Remote Similarity	NPD5186	Approved
0.6534	Remote Similarity	NPD5183	Approved
0.6534	Remote Similarity	NPD1161	Approved
0.6533	Remote Similarity	NPD3393	Approved
0.6533	Remote Similarity	NPD3394	Approved
0.6533	Remote Similarity	NPD3389	Approved
0.6529	Remote Similarity	NPD4042	Phase 2
0.6529	Remote Similarity	NPD4045	Phase 2
0.6527	Remote Similarity	NPD5942	Approved
0.6527	Remote Similarity	NPD4942	Approved
0.6527	Remote Similarity	NPD1664	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD5941	Approved
0.6526	Remote Similarity	NPD6999	Discontinued
0.6526	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7429	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4539	Phase 1
0.6522	Remote Similarity	NPD6636	Phase 3
0.6519	Remote Similarity	NPD3178	Discontinued
0.6517	Remote Similarity	NPD2359	Approved
0.6517	Remote Similarity	NPD3522	Approved
0.6516	Remote Similarity	NPD9540	Approved
0.6514	Remote Similarity	NPD3587	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD9692	Approved
0.6513	Remote Similarity	NPD9693	Approved
0.6509	Remote Similarity	NPD1879	Approved
0.6508	Remote Similarity	NPD6162	Approved
0.6508	Remote Similarity	NPD6161	Approved
0.6505	Remote Similarity	NPD2336	Approved
0.6503	Remote Similarity	NPD1222	Discontinued
0.6497	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD2387	Approved
0.6484	Remote Similarity	NPD5596	Phase 2
0.6481	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.648	Remote Similarity	NPD2361	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