NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	235.04
Volume:	226.965
LogP:	2.241
LogD:	2.164
LogS:	-3.48
# Rotatable Bonds:	1
TPSA:	52.32
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.812
Synthetic Accessibility Score:	3.018
Fsp3:	0.083
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:	-4.614
MDCK Permeability:	1.907598925754428e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.106
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988
Plasma Protein Binding (PPB):	96.2892837524414%
Volume Distribution (VD):	1.176
Pgp-substrate:	5.006112098693848%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.728
CYP2C19-inhibitor:	0.393
CYP2C19-substrate:	0.154
CYP2C9-inhibitor:	0.173
CYP2C9-substrate:	0.602
CYP2D6-inhibitor:	0.056
CYP2D6-substrate:	0.877
CYP3A4-inhibitor:	0.088
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	10.671
Half-life (T1/2):	0.586

ADMET: Toxicity

hERG Blockers:	0.169
Human Hepatotoxicity (H-HT):	0.333
Drug-inuced Liver Injury (DILI):	0.701
AMES Toxicity:	0.877
Rat Oral Acute Toxicity:	0.404
Maximum Recommended Daily Dose:	0.359
Skin Sensitization:	0.572
Carcinogencity:	0.859
Eye Corrosion:	0.003
Eye Irritation:	0.055
Respiratory Toxicity:	0.754

Download Data

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

Natural Product: NPC160747

Natural Product ID:	NPC160747
*Common Name:**	(3E)-3-(Chloromethylidene)-1-Benzoxepine-7-Carboxamide
IUPAC Name:	(3E)-3-(chloromethylidene)-1-benzoxepine-7-carboxamide
Synonyms:
Standard InCHIKey:	HBLXRWOEWPJYPL-SOFGYWHQSA-N
Standard InCHI:	InChI=1S/C12H10ClNO2/c13-6-8-1-2-9-5-10(12(14)15)3-4-11(9)16-7-8/h1-6H,7H2,(H2,14,15)/b8-6+
SMILES:	Cl/C=C1/COc2c(C=C1)cc(cc2)C(=O)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097212
PubChem CID:	46210597
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001910] Benzoxepines

*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
NPO23728	Favolaschia tonkinensis	Species	Favolaschiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20329738]
NPO23728	Favolaschia tonkinensis	Species	Favolaschiaceae	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	6

Activity Type	# Activity
Cell Line	4
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	12.15	ug.mL-1	PMID[490580]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[490580]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[490580]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	50.0	ug.mL-1	PMID[490580]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	>	10.0	ug.mL-1	PMID[490580]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	50.0	ug.mL-1	PMID[490580]

☑ 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 NPC160747 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	299
0.1-0.2	2701
0.2-0.3	7798
0.3-0.4	10045
0.4-0.5	4948
0.5-0.6	11902
0.6-0.7	4904
0.7-0.8	96
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8286	Intermediate Similarity	NPC66158
0.7956	Intermediate Similarity	NPC11799
0.7956	Intermediate Similarity	NPC141252
0.7842	Intermediate Similarity	NPC470858
0.7744	Intermediate Similarity	NPC252004
0.7714	Intermediate Similarity	NPC165556
0.7622	Intermediate Similarity	NPC66246
0.7622	Intermediate Similarity	NPC939
0.7622	Intermediate Similarity	NPC170546
0.7578	Intermediate Similarity	NPC473196
0.7569	Intermediate Similarity	NPC282230
0.7569	Intermediate Similarity	NPC183348
0.7556	Intermediate Similarity	NPC160179
0.7552	Intermediate Similarity	NPC50583
0.7535	Intermediate Similarity	NPC237868
0.7519	Intermediate Similarity	NPC23332
0.7519	Intermediate Similarity	NPC57879
0.7517	Intermediate Similarity	NPC470977
0.7517	Intermediate Similarity	NPC196979
0.7517	Intermediate Similarity	NPC15083
0.7517	Intermediate Similarity	NPC470976
0.7483	Intermediate Similarity	NPC37512
0.7466	Intermediate Similarity	NPC470859
0.7444	Intermediate Similarity	NPC183648
0.7431	Intermediate Similarity	NPC2401
0.7397	Intermediate Similarity	NPC279596
0.7376	Intermediate Similarity	NPC291189
0.7376	Intermediate Similarity	NPC69403
0.7372	Intermediate Similarity	NPC470860
0.7347	Intermediate Similarity	NPC266425
0.7329	Intermediate Similarity	NPC109778
0.7319	Intermediate Similarity	NPC469954
0.7319	Intermediate Similarity	NPC142042
0.731	Intermediate Similarity	NPC125887
0.7305	Intermediate Similarity	NPC314329
0.7299	Intermediate Similarity	NPC220540
0.7297	Intermediate Similarity	NPC229646
0.7279	Intermediate Similarity	NPC53953
0.7279	Intermediate Similarity	NPC90903
0.7273	Intermediate Similarity	NPC221798
0.7266	Intermediate Similarity	NPC152159
0.7248	Intermediate Similarity	NPC247743
0.7241	Intermediate Similarity	NPC293387
0.723	Intermediate Similarity	NPC169766
0.723	Intermediate Similarity	NPC132308
0.7214	Intermediate Similarity	NPC35744
0.7211	Intermediate Similarity	NPC327457
0.7211	Intermediate Similarity	NPC86774
0.7211	Intermediate Similarity	NPC245395
0.7194	Intermediate Similarity	NPC217423
0.7194	Intermediate Similarity	NPC45104
0.7172	Intermediate Similarity	NPC474737
0.7172	Intermediate Similarity	NPC475236
0.7163	Intermediate Similarity	NPC230951
0.7153	Intermediate Similarity	NPC255073
0.7153	Intermediate Similarity	NPC184219
0.7153	Intermediate Similarity	NPC107846
0.7153	Intermediate Similarity	NPC279916
0.7143	Intermediate Similarity	NPC32298
0.7143	Intermediate Similarity	NPC473019
0.7143	Intermediate Similarity	NPC206007
0.7133	Intermediate Similarity	NPC196708
0.7123	Intermediate Similarity	NPC121104
0.7122	Intermediate Similarity	NPC316062
0.7103	Intermediate Similarity	NPC2771
0.7103	Intermediate Similarity	NPC473626
0.7092	Intermediate Similarity	NPC201284
0.7092	Intermediate Similarity	NPC61779
0.7092	Intermediate Similarity	NPC54243
0.7078	Intermediate Similarity	NPC11566
0.7078	Intermediate Similarity	NPC137009
0.7075	Intermediate Similarity	NPC283079
0.7059	Intermediate Similarity	NPC259685
0.7059	Intermediate Similarity	NPC253616
0.7051	Intermediate Similarity	NPC17760
0.705	Intermediate Similarity	NPC188907
0.7042	Intermediate Similarity	NPC246214
0.7039	Intermediate Similarity	NPC46869
0.7039	Intermediate Similarity	NPC151113
0.7039	Intermediate Similarity	NPC163029
0.7039	Intermediate Similarity	NPC60667
0.7037	Intermediate Similarity	NPC473194
0.7034	Intermediate Similarity	NPC89630
0.7032	Intermediate Similarity	NPC472409
0.7032	Intermediate Similarity	NPC184053
0.7032	Intermediate Similarity	NPC470856
0.7021	Intermediate Similarity	NPC171023
0.7021	Intermediate Similarity	NPC293424
0.702	Intermediate Similarity	NPC209858
0.702	Intermediate Similarity	NPC292998
0.7014	Intermediate Similarity	NPC67300
0.7013	Intermediate Similarity	NPC36414
0.7007	Intermediate Similarity	NPC54626
0.7007	Intermediate Similarity	NPC475496
0.7007	Intermediate Similarity	NPC49852
0.7007	Intermediate Similarity	NPC233238
0.7	Intermediate Similarity	NPC284424
0.7	Intermediate Similarity	NPC183103
0.7	Intermediate Similarity	NPC175159
0.6993	Remote Similarity	NPC225245
0.6993	Remote Similarity	NPC254741
0.6993	Remote Similarity	NPC29638
0.6993	Remote Similarity	NPC268081
0.6993	Remote Similarity	NPC161196
0.6993	Remote Similarity	NPC156910
0.6993	Remote Similarity	NPC295317
0.6992	Remote Similarity	NPC38209
0.6987	Remote Similarity	NPC3188
0.6987	Remote Similarity	NPC27220
0.6986	Remote Similarity	NPC224657
0.6986	Remote Similarity	NPC65041
0.6974	Remote Similarity	NPC106606
0.6974	Remote Similarity	NPC470844
0.6974	Remote Similarity	NPC125920
0.6974	Remote Similarity	NPC125269
0.6974	Remote Similarity	NPC164136
0.6972	Remote Similarity	NPC137710
0.6968	Remote Similarity	NPC37206
0.6968	Remote Similarity	NPC473076
0.6968	Remote Similarity	NPC23257
0.6966	Remote Similarity	NPC474691
0.6959	Remote Similarity	NPC473907
0.6948	Remote Similarity	NPC476480
0.6948	Remote Similarity	NPC84585
0.6948	Remote Similarity	NPC62735
0.6948	Remote Similarity	NPC157855
0.6943	Remote Similarity	NPC147145
0.694	Remote Similarity	NPC128730
0.6939	Remote Similarity	NPC177925
0.6939	Remote Similarity	NPC474264
0.6934	Remote Similarity	NPC473809
0.6933	Remote Similarity	NPC239134
0.6933	Remote Similarity	NPC164295
0.6933	Remote Similarity	NPC104854
0.6933	Remote Similarity	NPC301717
0.6933	Remote Similarity	NPC472517
0.6928	Remote Similarity	NPC471316
0.6928	Remote Similarity	NPC99854
0.6923	Remote Similarity	NPC471587
0.6917	Remote Similarity	NPC298224
0.6914	Remote Similarity	NPC470708
0.6913	Remote Similarity	NPC78662
0.6913	Remote Similarity	NPC8005
0.6913	Remote Similarity	NPC473894
0.6908	Remote Similarity	NPC27643
0.6908	Remote Similarity	NPC93756
0.6908	Remote Similarity	NPC108113
0.6906	Remote Similarity	NPC242136
0.6906	Remote Similarity	NPC26524
0.6903	Remote Similarity	NPC124269
0.6903	Remote Similarity	NPC17848
0.6903	Remote Similarity	NPC147686
0.6903	Remote Similarity	NPC329225
0.6903	Remote Similarity	NPC472460
0.6903	Remote Similarity	NPC473988
0.6901	Remote Similarity	NPC27633
0.6901	Remote Similarity	NPC94298
0.6899	Remote Similarity	NPC169591
0.6899	Remote Similarity	NPC143896
0.6899	Remote Similarity	NPC310130
0.6899	Remote Similarity	NPC59522
0.6899	Remote Similarity	NPC68104
0.6899	Remote Similarity	NPC149026
0.6899	Remote Similarity	NPC221432
0.6899	Remote Similarity	NPC91560
0.6899	Remote Similarity	NPC257097
0.6899	Remote Similarity	NPC164980
0.6899	Remote Similarity	NPC39329
0.6899	Remote Similarity	NPC150408
0.6899	Remote Similarity	NPC75049
0.6899	Remote Similarity	NPC175504
0.6897	Remote Similarity	NPC311219
0.6894	Remote Similarity	NPC119669
0.6892	Remote Similarity	NPC22783
0.689	Remote Similarity	NPC473193
0.6889	Remote Similarity	NPC176971
0.6889	Remote Similarity	NPC1065
0.6887	Remote Similarity	NPC278556
0.6883	Remote Similarity	NPC174999
0.6883	Remote Similarity	NPC222633
0.6883	Remote Similarity	NPC240593
0.6883	Remote Similarity	NPC187826
0.6883	Remote Similarity	NPC472516
0.6879	Remote Similarity	NPC324386
0.6879	Remote Similarity	NPC171870
0.6879	Remote Similarity	NPC110969
0.6879	Remote Similarity	NPC213322
0.6879	Remote Similarity	NPC103362
0.6879	Remote Similarity	NPC22467
0.6879	Remote Similarity	NPC312391
0.6879	Remote Similarity	NPC4743
0.6867	Remote Similarity	NPC477645
0.6867	Remote Similarity	NPC298268
0.6863	Remote Similarity	NPC144027
0.6863	Remote Similarity	NPC217914
0.6863	Remote Similarity	NPC236974
0.6863	Remote Similarity	NPC229128
0.6861	Remote Similarity	NPC259554
0.6859	Remote Similarity	NPC472515
0.6859	Remote Similarity	NPC136095

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 NPC160747 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	1056
0.2-0.3	1055
0.3-0.4	2389
0.4-0.5	2375
0.5-0.6	1568
0.6-0.7	461
0.7-0.8	16
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7551	Intermediate Similarity	NPD743	Approved
0.7466	Intermediate Similarity	NPD3140	Approved
0.7466	Intermediate Similarity	NPD3142	Approved
0.7407	Intermediate Similarity	NPD1241	Discontinued
0.7305	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1307	Phase 2
0.7222	Intermediate Similarity	NPD1309	Phase 2
0.7186	Intermediate Similarity	NPD2822	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2325	Approved
0.7089	Intermediate Similarity	NPD1670	Discontinued
0.7078	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7190	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1019	Discontinued
0.7051	Intermediate Similarity	NPD160	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2186	Approved
0.7014	Intermediate Similarity	NPD3972	Approved
0.7011	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2796	Approved
0.6981	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3869	Phase 3
0.6981	Remote Similarity	NPD3873	Phase 3
0.6975	Remote Similarity	NPD7317	Phase 3
0.6928	Remote Similarity	NPD2799	Discontinued
0.6903	Remote Similarity	NPD1549	Phase 2
0.6901	Remote Similarity	NPD9545	Approved
0.6897	Remote Similarity	NPD9717	Approved
0.6894	Remote Similarity	NPD824	Approved
0.689	Remote Similarity	NPD7318	Phase 3
0.6886	Remote Similarity	NPD2247	Approved
0.6886	Remote Similarity	NPD2249	Approved
0.6883	Remote Similarity	NPD4476	Approved
0.6883	Remote Similarity	NPD4477	Approved
0.6879	Remote Similarity	NPD3887	Approved
0.686	Remote Similarity	NPD3823	Discontinued
0.6852	Remote Similarity	NPD2592	Discontinued
0.6849	Remote Similarity	NPD4129	Approved
0.6846	Remote Similarity	NPD6832	Phase 2
0.6839	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2353	Approved
0.6839	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3690	Phase 2
0.6824	Remote Similarity	NPD3691	Phase 2
0.6807	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD196	Phase 1
0.6786	Remote Similarity	NPD594	Approved
0.6786	Remote Similarity	NPD592	Approved
0.6776	Remote Similarity	NPD1240	Approved
0.677	Remote Similarity	NPD7427	Discontinued
0.676	Remote Similarity	NPD3819	Phase 2
0.6757	Remote Similarity	NPD3567	Approved
0.6757	Remote Similarity	NPD1203	Approved
0.6757	Remote Similarity	NPD3568	Approved
0.6755	Remote Similarity	NPD1296	Phase 2
0.6755	Remote Similarity	NPD2313	Discontinued
0.6752	Remote Similarity	NPD1243	Approved
0.675	Remote Similarity	NPD4661	Approved
0.675	Remote Similarity	NPD2335	Discontinued
0.675	Remote Similarity	NPD4662	Approved
0.675	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6502	Phase 2
0.6746	Remote Similarity	NPD5183	Approved
0.6746	Remote Similarity	NPD5186	Approved
0.6733	Remote Similarity	NPD2614	Approved
0.6732	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2344	Approved
0.6725	Remote Similarity	NPD3366	Approved
0.6724	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD4466	Phase 1
0.671	Remote Similarity	NPD1510	Phase 2
0.6707	Remote Similarity	NPD955	Approved
0.6707	Remote Similarity	NPD5890	Approved
0.6707	Remote Similarity	NPD5889	Approved
0.6691	Remote Similarity	NPD9697	Approved
0.6689	Remote Similarity	NPD1876	Approved
0.6688	Remote Similarity	NPD1607	Approved
0.6687	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7177	Discontinued
0.6667	Remote Similarity	NPD6279	Approved
0.6667	Remote Similarity	NPD6280	Approved
0.6667	Remote Similarity	NPD2246	Approved
0.6667	Remote Similarity	NPD7577	Discontinued
0.6667	Remote Similarity	NPD920	Approved
0.6667	Remote Similarity	NPD454	Approved
0.6667	Remote Similarity	NPD2248	Approved
0.6667	Remote Similarity	NPD9494	Approved
0.6667	Remote Similarity	NPD2354	Approved
0.6647	Remote Similarity	NPD4503	Phase 2
0.6646	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2654	Approved
0.6642	Remote Similarity	NPD3134	Approved
0.6624	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD5691	Approved
0.6606	Remote Similarity	NPD2366	Approved
0.6606	Remote Similarity	NPD7411	Suspended
0.6605	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4628	Phase 3
0.6603	Remote Similarity	NPD3748	Approved
0.66	Remote Similarity	NPD2987	Approved
0.66	Remote Similarity	NPD2990	Approved
0.6594	Remote Similarity	NPD1358	Approved
0.6592	Remote Similarity	NPD7693	Approved
0.659	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.659	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD2680	Approved
0.6588	Remote Similarity	NPD2681	Approved
0.6587	Remote Similarity	NPD5977	Approved
0.6587	Remote Similarity	NPD5978	Approved
0.6584	Remote Similarity	NPD6799	Approved
0.6578	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD17	Approved
0.657	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2309	Approved
0.6562	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD2935	Discontinued
0.6558	Remote Similarity	NPD4307	Phase 2
0.6552	Remote Similarity	NPD3965	Phase 1
0.6552	Remote Similarity	NPD1894	Discontinued
0.6548	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6585	Discontinued
0.6543	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6181	Discontinued
0.6538	Remote Similarity	NPD1536	Approved
0.6536	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD6104	Discontinued
0.6533	Remote Similarity	NPD553	Approved
0.6533	Remote Similarity	NPD3267	Approved
0.6533	Remote Similarity	NPD3266	Approved
0.6533	Remote Similarity	NPD9567	Approved
0.6533	Remote Similarity	NPD552	Approved
0.6528	Remote Similarity	NPD9493	Approved
0.6527	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD7819	Suspended
0.6524	Remote Similarity	NPD957	Approved
0.6519	Remote Similarity	NPD1471	Phase 3
0.6516	Remote Similarity	NPD4622	Approved
0.6516	Remote Similarity	NPD9694	Discovery
0.6516	Remote Similarity	NPD4618	Approved
0.6516	Remote Similarity	NPD1933	Approved
0.6512	Remote Similarity	NPD5242	Approved
0.6507	Remote Similarity	NPD3049	Approved
0.6507	Remote Similarity	NPD1651	Approved
0.6506	Remote Similarity	NPD6385	Approved
0.6506	Remote Similarity	NPD6386	Approved
0.6497	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD2245	Discovery
0.649	Remote Similarity	NPD2798	Approved
0.6486	Remote Similarity	NPD1281	Approved
0.6485	Remote Similarity	NPD2651	Approved
0.6485	Remote Similarity	NPD2649	Approved
0.6485	Remote Similarity	NPD3769	Discontinued
0.6479	Remote Similarity	NPD821	Approved
0.6478	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD2424	Discontinued
0.6474	Remote Similarity	NPD7584	Approved
0.6474	Remote Similarity	NPD6894	Phase 1
0.6474	Remote Similarity	NPD7583	Approved
0.6471	Remote Similarity	NPD6862	Phase 2
0.6467	Remote Similarity	NPD6801	Discontinued
0.6467	Remote Similarity	NPD6538	Approved
0.6467	Remote Similarity	NPD6541	Approved
0.6464	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1778	Approved
0.6463	Remote Similarity	NPD2554	Approved
0.6463	Remote Similarity	NPD5846	Approved
0.6463	Remote Similarity	NPD6516	Phase 2
0.6463	Remote Similarity	NPD2556	Approved
0.6457	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD1538	Phase 1
0.6456	Remote Similarity	NPD1537	Approved
0.6456	Remote Similarity	NPD1519	Approved
0.6456	Remote Similarity	NPD1551	Phase 2
0.6446	Remote Similarity	NPD4380	Phase 2
0.6446	Remote Similarity	NPD6599	Discontinued
0.6443	Remote Similarity	NPD1608	Approved
0.644	Remote Similarity	NPD7585	Approved
0.6437	Remote Similarity	NPD3446	Phase 1
0.6433	Remote Similarity	NPD2904	Discontinued
0.6433	Remote Similarity	NPD1520	Approved
0.6433	Remote Similarity	NPD1521	Approved
0.6433	Remote Similarity	NPD5689	Approved
0.6433	Remote Similarity	NPD5688	Approved
0.6429	Remote Similarity	NPD411	Approved
0.6429	Remote Similarity	NPD6798	Discontinued
0.6429	Remote Similarity	NPD2684	Approved
0.6429	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD927	Approved
0.6424	Remote Similarity	NPD2797	Approved
0.642	Remote Similarity	NPD1729	Discontinued
0.642	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.642	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD3496	Discontinued
0.6419	Remote Similarity	NPD3294	Phase 2
0.6415	Remote Similarity	NPD2346	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