NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	206.06
Volume:	203.678
LogP:	1.816
LogD:	1.934
LogS:	-2.681
# Rotatable Bonds:	2
TPSA:	52.58
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.755
Synthetic Accessibility Score:	2.648
Fsp3:	0.182
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:	-4.607
MDCK Permeability:	2.423669138806872e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	91.55641174316406%
Volume Distribution (VD):	1.484
Pgp-substrate:	9.253336906433105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.921
CYP1A2-substrate:	0.755
CYP2C19-inhibitor:	0.787
CYP2C19-substrate:	0.151
CYP2C9-inhibitor:	0.168
CYP2C9-substrate:	0.629
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.647
CYP3A4-inhibitor:	0.088
CYP3A4-substrate:	0.253

ADMET: Excretion

Clearance (CL):	6.099
Half-life (T1/2):	0.593

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.385
Drug-inuced Liver Injury (DILI):	0.472
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.664
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.085
Carcinogencity:	0.474
Eye Corrosion:	0.017
Eye Irritation:	0.469
Respiratory Toxicity:	0.642

Download Data

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

Natural Product: NPC292036

Natural Product ID:	NPC292036
*Common Name:**	Cladobotrin
IUPAC Name:	5-(furan-2-yl)-4-methoxy-3-methylpyran-2-one
Synonyms:	Cladobotrin
Standard InCHIKey:	PVWHKVRSMRDQFV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H10O4/c1-7-10(13-2)8(6-15-11(7)12)9-4-3-5-14-9/h3-6H,1-2H3
SMILES:	Cc1c(c(coc1=O)c1ccco1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL440093
PubChem CID:	10262379
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones 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
NPO33218	cladobotyrum rubrobrunnescens	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9625624]

☑ 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
LD50	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	LD50	=	100.0	ug ml-1	PMID[484659]
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	LD50	=	100.0	ug ml-1	PMID[484660]

☑ 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 NPC292036 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	400
0.1-0.2	1993
0.2-0.3	5351
0.3-0.4	11153
0.4-0.5	7183
0.5-0.6	5895
0.6-0.7	6603
0.7-0.8	3724
0.8-0.85	348
0.85-0.9	46
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8774	High Similarity	NPC156768
0.8621	High Similarity	NPC187547
0.8621	High Similarity	NPC21831
0.8547	High Similarity	NPC67345
0.8547	High Similarity	NPC244862
0.8545	High Similarity	NPC42471
0.8448	Intermediate Similarity	NPC476031
0.8448	Intermediate Similarity	NPC476014
0.8396	Intermediate Similarity	NPC146316
0.8393	Intermediate Similarity	NPC471521
0.8393	Intermediate Similarity	NPC473356
0.8376	Intermediate Similarity	NPC312525
0.8376	Intermediate Similarity	NPC217180
0.8362	Intermediate Similarity	NPC11821
0.8362	Intermediate Similarity	NPC205523
0.8333	Intermediate Similarity	NPC270807
0.8333	Intermediate Similarity	NPC174915
0.8291	Intermediate Similarity	NPC76844
0.825	Intermediate Similarity	NPC1848
0.8246	Intermediate Similarity	NPC229387
0.8235	Intermediate Similarity	NPC4898
0.822	Intermediate Similarity	NPC131801
0.8208	Intermediate Similarity	NPC233791
0.8151	Intermediate Similarity	NPC291619
0.8151	Intermediate Similarity	NPC254958
0.8142	Intermediate Similarity	NPC219969
0.8103	Intermediate Similarity	NPC26157
0.8103	Intermediate Similarity	NPC1811
0.8083	Intermediate Similarity	NPC473969
0.8067	Intermediate Similarity	NPC227660
0.8065	Intermediate Similarity	NPC216810
0.8018	Intermediate Similarity	NPC217226
0.8017	Intermediate Similarity	NPC105249
0.8017	Intermediate Similarity	NPC230951
0.7982	Intermediate Similarity	NPC140688
0.7917	Intermediate Similarity	NPC217423
0.7903	Intermediate Similarity	NPC65735
0.7903	Intermediate Similarity	NPC188377
0.7895	Intermediate Similarity	NPC298087
0.7891	Intermediate Similarity	NPC136340
0.7886	Intermediate Similarity	NPC272487
0.7851	Intermediate Similarity	NPC206007
0.7833	Intermediate Similarity	NPC474987
0.7833	Intermediate Similarity	NPC45536
0.7815	Intermediate Similarity	NPC252004
0.7812	Intermediate Similarity	NPC21460
0.7805	Intermediate Similarity	NPC474136
0.7797	Intermediate Similarity	NPC22678
0.7787	Intermediate Similarity	NPC137710
0.7778	Intermediate Similarity	NPC52035
0.776	Intermediate Similarity	NPC118853
0.7752	Intermediate Similarity	NPC475092
0.775	Intermediate Similarity	NPC188907
0.7742	Intermediate Similarity	NPC283284
0.7742	Intermediate Similarity	NPC289911
0.7731	Intermediate Similarity	NPC53953
0.7731	Intermediate Similarity	NPC311987
0.7724	Intermediate Similarity	NPC474817
0.7717	Intermediate Similarity	NPC319140
0.7717	Intermediate Similarity	NPC95567
0.7698	Intermediate Similarity	NPC473885
0.7698	Intermediate Similarity	NPC471074
0.7692	Intermediate Similarity	NPC177331
0.7686	Intermediate Similarity	NPC470860
0.768	Intermediate Similarity	NPC476351
0.768	Intermediate Similarity	NPC311219
0.768	Intermediate Similarity	NPC475818
0.7674	Intermediate Similarity	NPC170546
0.7674	Intermediate Similarity	NPC66246
0.7669	Intermediate Similarity	NPC215109
0.7669	Intermediate Similarity	NPC170604
0.7652	Intermediate Similarity	NPC159786
0.7642	Intermediate Similarity	NPC244293
0.7634	Intermediate Similarity	NPC470740
0.7623	Intermediate Similarity	NPC45104
0.7623	Intermediate Similarity	NPC208906
0.7623	Intermediate Similarity	NPC144745
0.7615	Intermediate Similarity	NPC183348
0.7615	Intermediate Similarity	NPC282230
0.7603	Intermediate Similarity	NPC28054
0.76	Intermediate Similarity	NPC263870
0.7578	Intermediate Similarity	NPC141059
0.7576	Intermediate Similarity	NPC106247
0.7563	Intermediate Similarity	NPC54626
0.7563	Intermediate Similarity	NPC57879
0.7561	Intermediate Similarity	NPC243704
0.7561	Intermediate Similarity	NPC293424
0.7559	Intermediate Similarity	NPC71274
0.7559	Intermediate Similarity	NPC474829
0.7559	Intermediate Similarity	NPC75557
0.7559	Intermediate Similarity	NPC471559
0.7557	Intermediate Similarity	NPC470977
0.7557	Intermediate Similarity	NPC196979
0.7557	Intermediate Similarity	NPC470976
0.7557	Intermediate Similarity	NPC15083
0.7542	Intermediate Similarity	NPC209111
0.7541	Intermediate Similarity	NPC328451
0.7541	Intermediate Similarity	NPC59035
0.7541	Intermediate Similarity	NPC79202
0.7541	Intermediate Similarity	NPC316062
0.7537	Intermediate Similarity	NPC286130
0.7537	Intermediate Similarity	NPC473268
0.7537	Intermediate Similarity	NPC307401
0.752	Intermediate Similarity	NPC79557
0.75	Intermediate Similarity	NPC128730
0.75	Intermediate Similarity	NPC329922
0.75	Intermediate Similarity	NPC81912
0.75	Intermediate Similarity	NPC329694
0.75	Intermediate Similarity	NPC4164
0.75	Intermediate Similarity	NPC474260
0.75	Intermediate Similarity	NPC83301
0.75	Intermediate Similarity	NPC308799
0.7481	Intermediate Similarity	NPC472376
0.748	Intermediate Similarity	NPC107482
0.7465	Intermediate Similarity	NPC88445
0.7462	Intermediate Similarity	NPC59502
0.746	Intermediate Similarity	NPC473379
0.746	Intermediate Similarity	NPC471549
0.7447	Intermediate Similarity	NPC304443
0.7447	Intermediate Similarity	NPC113428
0.7447	Intermediate Similarity	NPC61284
0.7447	Intermediate Similarity	NPC74539
0.7442	Intermediate Similarity	NPC184391
0.7442	Intermediate Similarity	NPC474830
0.7438	Intermediate Similarity	NPC279916
0.7436	Intermediate Similarity	NPC176971
0.7426	Intermediate Similarity	NPC474615
0.7426	Intermediate Similarity	NPC202260
0.7426	Intermediate Similarity	NPC107571
0.7424	Intermediate Similarity	NPC473982
0.7422	Intermediate Similarity	NPC179354
0.7419	Intermediate Similarity	NPC32298
0.7413	Intermediate Similarity	NPC191104
0.741	Intermediate Similarity	NPC166858
0.741	Intermediate Similarity	NPC51146
0.7405	Intermediate Similarity	NPC238309
0.7402	Intermediate Similarity	NPC291189
0.7402	Intermediate Similarity	NPC69403
0.7402	Intermediate Similarity	NPC16922
0.7394	Intermediate Similarity	NPC266743
0.7388	Intermediate Similarity	NPC92941
0.7385	Intermediate Similarity	NPC474279
0.7385	Intermediate Similarity	NPC474438
0.7381	Intermediate Similarity	NPC97566
0.7381	Intermediate Similarity	NPC115859
0.7373	Intermediate Similarity	NPC151530
0.7373	Intermediate Similarity	NPC157473
0.7372	Intermediate Similarity	NPC282973
0.7372	Intermediate Similarity	NPC148374
0.7368	Intermediate Similarity	NPC293253
0.7368	Intermediate Similarity	NPC474426
0.7368	Intermediate Similarity	NPC474425
0.7368	Intermediate Similarity	NPC474407
0.736	Intermediate Similarity	NPC54243
0.7357	Intermediate Similarity	NPC195920
0.7353	Intermediate Similarity	NPC220094
0.7353	Intermediate Similarity	NPC476943
0.7348	Intermediate Similarity	NPC477645
0.7344	Intermediate Similarity	NPC243269
0.7344	Intermediate Similarity	NPC11799
0.7344	Intermediate Similarity	NPC141252
0.7333	Intermediate Similarity	NPC183648
0.7333	Intermediate Similarity	NPC146872
0.7333	Intermediate Similarity	NPC66705
0.7328	Intermediate Similarity	NPC179686
0.7328	Intermediate Similarity	NPC50583
0.7328	Intermediate Similarity	NPC208389
0.7323	Intermediate Similarity	NPC314329
0.7317	Intermediate Similarity	NPC220540
0.7317	Intermediate Similarity	NPC150895
0.7308	Intermediate Similarity	NPC473355
0.7308	Intermediate Similarity	NPC471573
0.7308	Intermediate Similarity	NPC471501
0.7308	Intermediate Similarity	NPC476016
0.7308	Intermediate Similarity	NPC471554
0.7308	Intermediate Similarity	NPC475236
0.7308	Intermediate Similarity	NPC137570
0.7305	Intermediate Similarity	NPC475864
0.7305	Intermediate Similarity	NPC208584
0.7305	Intermediate Similarity	NPC233763
0.7305	Intermediate Similarity	NPC246903
0.7302	Intermediate Similarity	NPC246214
0.7299	Intermediate Similarity	NPC474722
0.7293	Intermediate Similarity	NPC471817
0.7287	Intermediate Similarity	NPC221798
0.7286	Intermediate Similarity	NPC84479
0.728	Intermediate Similarity	NPC94637
0.7279	Intermediate Similarity	NPC470742
0.7279	Intermediate Similarity	NPC310830
0.7279	Intermediate Similarity	NPC42400
0.7279	Intermediate Similarity	NPC186626
0.7273	Intermediate Similarity	NPC23332
0.7273	Intermediate Similarity	NPC473019
0.7266	Intermediate Similarity	NPC470856
0.7265	Intermediate Similarity	NPC283546
0.7265	Intermediate Similarity	NPC109637
0.726	Intermediate Similarity	NPC131725
0.7254	Intermediate Similarity	NPC224418
0.7254	Intermediate Similarity	NPC190572
0.7252	Intermediate Similarity	NPC293387

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 NPC292036 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	998
0.2-0.3	1755
0.3-0.4	2813
0.4-0.5	1900
0.5-0.6	962
0.6-0.7	251
0.7-0.8	90
0.8-0.85	10
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7717	Intermediate Similarity	NPD1019	Discontinued
0.768	Intermediate Similarity	NPD9717	Approved
0.7597	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD9092	Discovery
0.7447	Intermediate Similarity	NPD920	Approved
0.7438	Intermediate Similarity	NPD1241	Discontinued
0.741	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD1203	Approved
0.7323	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD1358	Approved
0.7226	Intermediate Similarity	NPD1551	Phase 2
0.7194	Intermediate Similarity	NPD1243	Approved
0.7185	Intermediate Similarity	NPD1933	Approved
0.7143	Intermediate Similarity	NPD3134	Approved
0.712	Intermediate Similarity	NPD9493	Approved
0.709	Intermediate Similarity	NPD2313	Discontinued
0.709	Intermediate Similarity	NPD411	Approved
0.7067	Intermediate Similarity	NPD919	Approved
0.7059	Intermediate Similarity	NPD9697	Approved
0.7059	Intermediate Similarity	NPD447	Suspended
0.6985	Remote Similarity	NPD4307	Phase 2
0.697	Remote Similarity	NPD3266	Approved
0.697	Remote Similarity	NPD3267	Approved
0.6929	Remote Similarity	NPD1471	Phase 3
0.6917	Remote Similarity	NPD5647	Approved
0.6906	Remote Similarity	NPD2799	Discontinued
0.6875	Remote Similarity	NPD6799	Approved
0.6875	Remote Similarity	NPD9545	Approved
0.6857	Remote Similarity	NPD2796	Approved
0.6828	Remote Similarity	NPD5401	Approved
0.6809	Remote Similarity	NPD2344	Approved
0.6791	Remote Similarity	NPD2798	Approved
0.6786	Remote Similarity	NPD4308	Phase 3
0.6786	Remote Similarity	NPD3748	Approved
0.6783	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.678	Remote Similarity	NPD1238	Approved
0.6774	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.675	Remote Similarity	NPD9261	Approved
0.6735	Remote Similarity	NPD5403	Approved
0.6716	Remote Similarity	NPD2797	Approved
0.6715	Remote Similarity	NPD3268	Approved
0.6713	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5585	Approved
0.669	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD769	Approved
0.6667	Remote Similarity	NPD7033	Discontinued
0.6645	Remote Similarity	NPD1247	Approved
0.6643	Remote Similarity	NPD1549	Phase 2
0.6642	Remote Similarity	NPD1876	Approved
0.6642	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD3225	Approved
0.6641	Remote Similarity	NPD1778	Approved
0.6641	Remote Similarity	NPD17	Approved
0.6621	Remote Similarity	NPD3887	Approved
0.6621	Remote Similarity	NPD2309	Approved
0.662	Remote Similarity	NPD2935	Discontinued
0.6619	Remote Similarity	NPD3142	Approved
0.6619	Remote Similarity	NPD3140	Approved
0.6618	Remote Similarity	NPD9494	Approved
0.6617	Remote Similarity	NPD3972	Approved
0.6615	Remote Similarity	NPD1894	Discontinued
0.6614	Remote Similarity	NPD9069	Phase 1
0.6613	Remote Similarity	NPD2182	Approved
0.6609	Remote Similarity	NPD9365	Approved
0.6603	Remote Similarity	NPD6808	Phase 2
0.66	Remote Similarity	NPD6599	Discontinued
0.6593	Remote Similarity	NPD6362	Approved
0.6591	Remote Similarity	NPD3496	Discontinued
0.6573	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD2353	Approved
0.6573	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD164	Approved
0.6556	Remote Similarity	NPD7411	Suspended
0.6556	Remote Similarity	NPD5890	Approved
0.6556	Remote Similarity	NPD5889	Approved
0.6552	Remote Similarity	NPD4628	Phase 3
0.6552	Remote Similarity	NPD3750	Approved
0.6552	Remote Similarity	NPD1562	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD1510	Phase 2
0.6535	Remote Similarity	NPD5535	Approved
0.6532	Remote Similarity	NPD9264	Approved
0.6532	Remote Similarity	NPD9263	Approved
0.6532	Remote Similarity	NPD9267	Approved
0.6529	Remote Similarity	NPD291	Approved
0.6528	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6801	Discontinued
0.65	Remote Similarity	NPD1240	Approved
0.6493	Remote Similarity	NPD1481	Phase 2
0.6493	Remote Similarity	NPD1608	Approved
0.648	Remote Similarity	NPD74	Approved
0.648	Remote Similarity	NPD9266	Approved
0.6475	Remote Similarity	NPD1296	Phase 2
0.6475	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7819	Suspended
0.6471	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3749	Approved
0.6444	Remote Similarity	NPD4359	Approved
0.6434	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3817	Phase 2
0.6429	Remote Similarity	NPD5402	Approved
0.6429	Remote Similarity	NPD6233	Phase 2
0.6418	Remote Similarity	NPD422	Phase 1
0.6418	Remote Similarity	NPD1535	Discovery
0.6412	Remote Similarity	NPD5536	Phase 2
0.641	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD1607	Approved
0.6405	Remote Similarity	NPD6279	Approved
0.6405	Remote Similarity	NPD6280	Approved
0.64	Remote Similarity	NPD290	Approved
0.6395	Remote Similarity	NPD2354	Approved
0.6386	Remote Similarity	NPD1987	Approved
0.6386	Remote Similarity	NPD1985	Approved
0.6382	Remote Similarity	NPD6585	Discontinued
0.638	Remote Similarity	NPD6559	Discontinued
0.6377	Remote Similarity	NPD454	Approved
0.6376	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD957	Approved
0.6357	Remote Similarity	NPD6798	Discontinued
0.6351	Remote Similarity	NPD7440	Discontinued
0.6346	Remote Similarity	NPD7075	Discontinued
0.6338	Remote Similarity	NPD6355	Discontinued
0.6335	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6273	Approved
0.6333	Remote Similarity	NPD2186	Approved
0.6331	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5691	Approved
0.6316	Remote Similarity	NPD3226	Approved
0.6312	Remote Similarity	NPD4062	Phase 3
0.631	Remote Similarity	NPD1986	Approved
0.6308	Remote Similarity	NPD9281	Approved
0.6299	Remote Similarity	NPD556	Approved
0.6296	Remote Similarity	NPD1281	Approved
0.6294	Remote Similarity	NPD6653	Approved
0.6291	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD3873	Phase 3
0.6291	Remote Similarity	NPD3869	Phase 3
0.6287	Remote Similarity	NPD8434	Phase 2
0.6282	Remote Similarity	NPD7768	Phase 2
0.6282	Remote Similarity	NPD3882	Suspended
0.6267	Remote Similarity	NPD4661	Approved
0.6267	Remote Similarity	NPD4662	Approved
0.6267	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD1282	Approved
0.6259	Remote Similarity	NPD2654	Approved
0.6258	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD3764	Approved
0.6234	Remote Similarity	NPD2366	Approved
0.6234	Remote Similarity	NPD958	Approved
0.6233	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD6004	Phase 3
0.6233	Remote Similarity	NPD6002	Phase 3
0.6233	Remote Similarity	NPD6005	Phase 3
0.6224	Remote Similarity	NPD230	Phase 1
0.6224	Remote Similarity	NPD4618	Approved
0.6224	Remote Similarity	NPD4622	Approved
0.6222	Remote Similarity	NPD3847	Discontinued
0.622	Remote Similarity	NPD2684	Approved
0.6218	Remote Similarity	NPD1202	Approved
0.6211	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.62	Remote Similarity	NPD1511	Approved
0.6199	Remote Similarity	NPD3958	Approved
0.6197	Remote Similarity	NPD520	Approved
0.6197	Remote Similarity	NPD8032	Phase 2
0.6194	Remote Similarity	NPD6844	Discontinued
0.619	Remote Similarity	NPD968	Approved
0.6182	Remote Similarity	NPD6765	Approved
0.6182	Remote Similarity	NPD6764	Approved
0.6174	Remote Similarity	NPD9259	Approved
0.6174	Remote Similarity	NPD9257	Approved
0.6172	Remote Similarity	NPD2067	Discontinued
0.6164	Remote Similarity	NPD5494	Approved
0.6159	Remote Similarity	NPD2532	Approved
0.6159	Remote Similarity	NPD1283	Approved
0.6159	Remote Similarity	NPD2534	Approved
0.6159	Remote Similarity	NPD2533	Approved
0.6154	Remote Similarity	NPD7843	Approved
0.6154	Remote Similarity	NPD5760	Phase 2
0.6154	Remote Similarity	NPD9295	Approved
0.6154	Remote Similarity	NPD5761	Phase 2
0.6154	Remote Similarity	NPD2979	Phase 3
0.6149	Remote Similarity	NPD3926	Phase 2
0.6142	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD5689	Approved
0.6138	Remote Similarity	NPD5688	Approved
0.6138	Remote Similarity	NPD743	Approved
0.6127	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD5049	Phase 3
0.6118	Remote Similarity	NPD1512	Approved
0.6115	Remote Similarity	NPD2296	Approved
0.6111	Remote Similarity	NPD7852	Clinical (unspecified phase)

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