NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	210.1
Volume:	235.298
LogP:	5.244
LogD:	4.214
LogS:	-6.432
# Rotatable Bonds:	0
TPSA:	13.14
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.533
Synthetic Accessibility Score:	2.162
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.807
MDCK Permeability:	2.1014280719100498e-05
Pgp-inhibitor:	0.189
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.859
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.221
Plasma Protein Binding (PPB):	98.43488311767578%
Volume Distribution (VD):	1.253
Pgp-substrate:	1.7386062145233154%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.943
CYP2C19-inhibitor:	0.711
CYP2C19-substrate:	0.101
CYP2C9-inhibitor:	0.35
CYP2C9-substrate:	0.834
CYP2D6-inhibitor:	0.868
CYP2D6-substrate:	0.946
CYP3A4-inhibitor:	0.675
CYP3A4-substrate:	0.371

ADMET: Excretion

Clearance (CL):	9.204
Half-life (T1/2):	0.103

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.147
Drug-inuced Liver Injury (DILI):	0.836
AMES Toxicity:	0.373
Rat Oral Acute Toxicity:	0.206
Maximum Recommended Daily Dose:	0.803
Skin Sensitization:	0.072
Carcinogencity:	0.671
Eye Corrosion:	0.02
Eye Irritation:	0.976
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC83301

Natural Product ID:	NPC83301
*Common Name:**	Linderazulene
IUPAC Name:	1,5,8-trimethylazuleno[6,5-b]furan
Synonyms:	Linderazulene
Standard InCHIKey:	LMVGRKPOXLBIFQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O/c1-9-4-5-12-10(2)6-15-14(7-13(9)12)11(3)8-16-15/h4-8H,1-3H3
SMILES:	Cc1ccc2-c1cc1c(C)coc1cc2C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503851
PubChem CID:	656393
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002936] Cycloheptafurans

*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
NPO33147	Paramuricea	Genus	Paramuriceidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730254]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[17999353]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[19639966]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30415	Lindera aggregate	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4682	Lindera aggregata	Species	Lauraceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	18.8	ug.mL-1	PMID[496905]

☑ 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 NPC83301 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	541
0.1-0.2	2366
0.2-0.3	6220
0.3-0.4	11815
0.4-0.5	5653
0.5-0.6	9298
0.6-0.7	6225
0.7-0.8	546
0.8-0.85	24
0.85-0.9	6
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9916	High Similarity	NPC141059
0.9593	High Similarity	NPC475092
0.878	High Similarity	NPC115859
0.8689	High Similarity	NPC206007
0.8618	High Similarity	NPC137710
0.8548	High Similarity	NPC246214
0.8425	Intermediate Similarity	NPC118853
0.8359	Intermediate Similarity	NPC471074
0.8359	Intermediate Similarity	NPC473885
0.8347	Intermediate Similarity	NPC22678
0.8305	Intermediate Similarity	NPC42471
0.8293	Intermediate Similarity	NPC28054
0.8293	Intermediate Similarity	NPC205523
0.8244	Intermediate Similarity	NPC50583
0.8226	Intermediate Similarity	NPC59035
0.8226	Intermediate Similarity	NPC79202
0.816	Intermediate Similarity	NPC217180
0.816	Intermediate Similarity	NPC312525
0.8148	Intermediate Similarity	NPC209858
0.8106	Intermediate Similarity	NPC59502
0.8047	Intermediate Similarity	NPC97566
0.8016	Intermediate Similarity	NPC227660
0.8015	Intermediate Similarity	NPC324117
0.8	Intermediate Similarity	NPC11799
0.8	Intermediate Similarity	NPC141252
0.8	Intermediate Similarity	NPC188377
0.8	Intermediate Similarity	NPC150895
0.8	Intermediate Similarity	NPC65735
0.7937	Intermediate Similarity	NPC45536
0.7937	Intermediate Similarity	NPC316062
0.792	Intermediate Similarity	NPC252004
0.7914	Intermediate Similarity	NPC233707
0.7891	Intermediate Similarity	NPC473969
0.7883	Intermediate Similarity	NPC265793
0.7881	Intermediate Similarity	NPC156768
0.7879	Intermediate Similarity	NPC470858
0.7832	Intermediate Similarity	NPC247221
0.7823	Intermediate Similarity	NPC54626
0.7812	Intermediate Similarity	NPC187547
0.7812	Intermediate Similarity	NPC243704
0.7812	Intermediate Similarity	NPC21831
0.781	Intermediate Similarity	NPC106247
0.7794	Intermediate Similarity	NPC473982
0.777	Intermediate Similarity	NPC64157
0.777	Intermediate Similarity	NPC278832
0.7769	Intermediate Similarity	NPC79557
0.7744	Intermediate Similarity	NPC216810
0.7734	Intermediate Similarity	NPC131801
0.7727	Intermediate Similarity	NPC178382
0.7721	Intermediate Similarity	NPC477645
0.7714	Intermediate Similarity	NPC130976
0.771	Intermediate Similarity	NPC314329
0.7708	Intermediate Similarity	NPC93241
0.7708	Intermediate Similarity	NPC27798
0.7698	Intermediate Similarity	NPC53953
0.7692	Intermediate Similarity	NPC27220
0.7687	Intermediate Similarity	NPC184391
0.768	Intermediate Similarity	NPC105249
0.768	Intermediate Similarity	NPC57879
0.768	Intermediate Similarity	NPC23332
0.766	Intermediate Similarity	NPC62735
0.7656	Intermediate Similarity	NPC476031
0.7656	Intermediate Similarity	NPC476014
0.7647	Intermediate Similarity	NPC66246
0.7647	Intermediate Similarity	NPC170546
0.7647	Intermediate Similarity	NPC939
0.7643	Intermediate Similarity	NPC163029
0.7643	Intermediate Similarity	NPC170604
0.7643	Intermediate Similarity	NPC215109
0.7643	Intermediate Similarity	NPC473268
0.7643	Intermediate Similarity	NPC307401
0.7639	Intermediate Similarity	NPC117674
0.763	Intermediate Similarity	NPC329707
0.7615	Intermediate Similarity	NPC201284
0.7615	Intermediate Similarity	NPC35744
0.7615	Intermediate Similarity	NPC4898
0.7609	Intermediate Similarity	NPC471006
0.76	Intermediate Similarity	NPC183648
0.7597	Intermediate Similarity	NPC144745
0.7597	Intermediate Similarity	NPC469954
0.7597	Intermediate Similarity	NPC208906
0.7594	Intermediate Similarity	NPC243269
0.7591	Intermediate Similarity	NPC136340
0.7591	Intermediate Similarity	NPC282230
0.7591	Intermediate Similarity	NPC183348
0.7589	Intermediate Similarity	NPC472376
0.7586	Intermediate Similarity	NPC56731
0.7586	Intermediate Similarity	NPC290038
0.7571	Intermediate Similarity	NPC204592
0.7551	Intermediate Similarity	NPC198427
0.7542	Intermediate Similarity	NPC146316
0.7538	Intermediate Similarity	NPC152159
0.7538	Intermediate Similarity	NPC32298
0.7538	Intermediate Similarity	NPC171023
0.7537	Intermediate Similarity	NPC71274
0.7537	Intermediate Similarity	NPC75557
0.7536	Intermediate Similarity	NPC279596
0.7536	Intermediate Similarity	NPC196979
0.7536	Intermediate Similarity	NPC15083
0.7536	Intermediate Similarity	NPC470976
0.7536	Intermediate Similarity	NPC470977
0.7535	Intermediate Similarity	NPC202260
0.7534	Intermediate Similarity	NPC208584
0.7534	Intermediate Similarity	NPC478166
0.7533	Intermediate Similarity	NPC471863
0.7519	Intermediate Similarity	NPC16922
0.7519	Intermediate Similarity	NPC474987
0.7519	Intermediate Similarity	NPC470860
0.7517	Intermediate Similarity	NPC472406
0.7517	Intermediate Similarity	NPC158871
0.75	Intermediate Similarity	NPC474279
0.75	Intermediate Similarity	NPC292036
0.75	Intermediate Similarity	NPC474438
0.75	Intermediate Similarity	NPC428300
0.7483	Intermediate Similarity	NPC308799
0.7483	Intermediate Similarity	NPC281398
0.7483	Intermediate Similarity	NPC112757
0.7483	Intermediate Similarity	NPC190572
0.7483	Intermediate Similarity	NPC224418
0.7482	Intermediate Similarity	NPC470859
0.7482	Intermediate Similarity	NPC293253
0.7481	Intermediate Similarity	NPC81912
0.7481	Intermediate Similarity	NPC224657
0.7481	Intermediate Similarity	NPC54243
0.7481	Intermediate Similarity	NPC329922
0.7481	Intermediate Similarity	NPC329694
0.7481	Intermediate Similarity	NPC474260
0.7467	Intermediate Similarity	NPC156244
0.7466	Intermediate Similarity	NPC469642
0.7465	Intermediate Similarity	NPC29638
0.7464	Intermediate Similarity	NPC245395
0.7462	Intermediate Similarity	NPC45104
0.7444	Intermediate Similarity	NPC477967
0.7444	Intermediate Similarity	NPC317217
0.744	Intermediate Similarity	NPC473356
0.744	Intermediate Similarity	NPC471521
0.7432	Intermediate Similarity	NPC113428
0.7432	Intermediate Similarity	NPC61284
0.7432	Intermediate Similarity	NPC93666
0.7426	Intermediate Similarity	NPC246392
0.7426	Intermediate Similarity	NPC319140
0.7426	Intermediate Similarity	NPC95567
0.7426	Intermediate Similarity	NPC290955
0.7426	Intermediate Similarity	NPC476016
0.7422	Intermediate Similarity	NPC279916
0.7417	Intermediate Similarity	NPC67654
0.7415	Intermediate Similarity	NPC230943
0.741	Intermediate Similarity	NPC125153
0.7407	Intermediate Similarity	NPC107846
0.7407	Intermediate Similarity	NPC474829
0.7407	Intermediate Similarity	NPC179354
0.7405	Intermediate Similarity	NPC87466
0.7405	Intermediate Similarity	NPC254958
0.7405	Intermediate Similarity	NPC293424
0.7405	Intermediate Similarity	NPC291619
0.74	Intermediate Similarity	NPC135303
0.74	Intermediate Similarity	NPC148423
0.7398	Intermediate Similarity	NPC38209
0.7397	Intermediate Similarity	NPC307346
0.7397	Intermediate Similarity	NPC166858
0.7397	Intermediate Similarity	NPC53192
0.7397	Intermediate Similarity	NPC51146
0.7397	Intermediate Similarity	NPC267004
0.7397	Intermediate Similarity	NPC218712
0.7397	Intermediate Similarity	NPC261733
0.7394	Intermediate Similarity	NPC286130
0.7391	Intermediate Similarity	NPC45947
0.7391	Intermediate Similarity	NPC21460
0.7388	Intermediate Similarity	NPC476351
0.7383	Intermediate Similarity	NPC266743
0.7383	Intermediate Similarity	NPC306788
0.7383	Intermediate Similarity	NPC95526
0.7381	Intermediate Similarity	NPC177331
0.7379	Intermediate Similarity	NPC263337
0.7376	Intermediate Similarity	NPC159786
0.7373	Intermediate Similarity	NPC233791
0.7372	Intermediate Similarity	NPC298884
0.7372	Intermediate Similarity	NPC26532
0.7368	Intermediate Similarity	NPC25351
0.7361	Intermediate Similarity	NPC473983
0.7361	Intermediate Similarity	NPC148374
0.7361	Intermediate Similarity	NPC201370
0.7357	Intermediate Similarity	NPC470740
0.7353	Intermediate Similarity	NPC2771
0.7353	Intermediate Similarity	NPC46536
0.7353	Intermediate Similarity	NPC52035
0.7353	Intermediate Similarity	NPC138139
0.7353	Intermediate Similarity	NPC23086
0.7353	Intermediate Similarity	NPC473626
0.7353	Intermediate Similarity	NPC74612
0.7347	Intermediate Similarity	NPC17262
0.7347	Intermediate Similarity	NPC302181
0.7338	Intermediate Similarity	NPC116639
0.7338	Intermediate Similarity	NPC298190
0.7333	Intermediate Similarity	NPC472298
0.7333	Intermediate Similarity	NPC477965
0.7333	Intermediate Similarity	NPC477038
0.7333	Intermediate Similarity	NPC88445
0.7328	Intermediate Similarity	NPC217423
0.7324	Intermediate Similarity	NPC303217

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 NPC83301 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	496
0.1-0.2	1031
0.2-0.3	1576
0.3-0.4	2899
0.4-0.5	1900
0.5-0.6	955
0.6-0.7	269
0.7-0.8	24
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
0.8043	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD1876	Approved
0.784	Intermediate Similarity	NPD1241	Discontinued
0.771	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD2344	Approved
0.7448	Intermediate Similarity	NPD2309	Approved
0.7397	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD3972	Approved
0.732	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD920	Approved
0.7297	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1471	Phase 3
0.72	Intermediate Similarity	NPD3873	Phase 3
0.72	Intermediate Similarity	NPD3869	Phase 3
0.7194	Intermediate Similarity	NPD6832	Phase 2
0.7192	Intermediate Similarity	NPD1243	Approved
0.719	Intermediate Similarity	NPD6280	Approved
0.719	Intermediate Similarity	NPD6279	Approved
0.7174	Intermediate Similarity	NPD2798	Approved
0.7164	Intermediate Similarity	NPD17	Approved
0.7153	Intermediate Similarity	NPD2799	Discontinued
0.7103	Intermediate Similarity	NPD2796	Approved
0.709	Intermediate Similarity	NPD1651	Approved
0.705	Intermediate Similarity	NPD1019	Discontinued
0.702	Intermediate Similarity	NPD6273	Approved
0.7007	Intermediate Similarity	NPD1608	Approved
0.7007	Intermediate Similarity	NPD9717	Approved
0.6993	Remote Similarity	NPD4307	Phase 2
0.6993	Remote Similarity	NPD3142	Approved
0.6993	Remote Similarity	NPD3140	Approved
0.6978	Remote Similarity	NPD3266	Approved
0.6978	Remote Similarity	NPD3267	Approved
0.6972	Remote Similarity	NPD2313	Discontinued
0.6962	Remote Similarity	NPD919	Approved
0.6959	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1281	Approved
0.6923	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3748	Approved
0.6913	Remote Similarity	NPD4628	Phase 3
0.6879	Remote Similarity	NPD9494	Approved
0.6879	Remote Similarity	NPD2296	Approved
0.6875	Remote Similarity	NPD1247	Approved
0.6871	Remote Similarity	NPD1551	Phase 2
0.6857	Remote Similarity	NPD2797	Approved
0.6857	Remote Similarity	NPD1203	Approved
0.6838	Remote Similarity	NPD5585	Approved
0.6832	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6808	Phase 2
0.6828	Remote Similarity	NPD6355	Discontinued
0.6824	Remote Similarity	NPD2346	Discontinued
0.6806	Remote Similarity	NPD8032	Phase 2
0.6803	Remote Similarity	NPD4308	Phase 3
0.6786	Remote Similarity	NPD1283	Approved
0.6779	Remote Similarity	NPD1549	Phase 2
0.6765	Remote Similarity	NPD9545	Approved
0.6765	Remote Similarity	NPD1894	Discontinued
0.6759	Remote Similarity	NPD1240	Approved
0.6755	Remote Similarity	NPD3887	Approved
0.6748	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3134	Approved
0.6742	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3268	Approved
0.6736	Remote Similarity	NPD3764	Approved
0.6712	Remote Similarity	NPD1933	Approved
0.6711	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6002	Phase 3
0.6711	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6005	Phase 3
0.6711	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6004	Phase 3
0.6711	Remote Similarity	NPD2353	Approved
0.6692	Remote Similarity	NPD1358	Approved
0.6691	Remote Similarity	NPD9092	Discovery
0.669	Remote Similarity	NPD5647	Approved
0.6689	Remote Similarity	NPD1510	Phase 2
0.6689	Remote Similarity	NPD3750	Approved
0.6689	Remote Similarity	NPD7003	Approved
0.6687	Remote Similarity	NPD3749	Approved
0.6687	Remote Similarity	NPD3926	Phase 2
0.6667	Remote Similarity	NPD1238	Approved
0.6667	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1607	Approved
0.6667	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9697	Approved
0.6644	Remote Similarity	NPD2979	Phase 3
0.6644	Remote Similarity	NPD4476	Approved
0.6644	Remote Similarity	NPD4477	Approved
0.6641	Remote Similarity	NPD2684	Approved
0.6623	Remote Similarity	NPD4661	Approved
0.6623	Remote Similarity	NPD4662	Approved
0.6621	Remote Similarity	NPD411	Approved
0.6621	Remote Similarity	NPD6798	Discontinued
0.6619	Remote Similarity	NPD3496	Discontinued
0.6618	Remote Similarity	NPD9493	Approved
0.6607	Remote Similarity	NPD6559	Discontinued
0.6604	Remote Similarity	NPD5761	Phase 2
0.6604	Remote Similarity	NPD5760	Phase 2
0.6599	Remote Similarity	NPD4618	Approved
0.6599	Remote Similarity	NPD447	Suspended
0.6599	Remote Similarity	NPD4622	Approved
0.6596	Remote Similarity	NPD4359	Approved
0.6594	Remote Similarity	NPD3444	Approved
0.6594	Remote Similarity	NPD3443	Approved
0.6594	Remote Similarity	NPD5691	Approved
0.6594	Remote Similarity	NPD3445	Approved
0.6569	Remote Similarity	NPD5536	Phase 2
0.6567	Remote Similarity	NPD5535	Approved
0.6558	Remote Similarity	NPD6799	Approved
0.6556	Remote Similarity	NPD2897	Discontinued
0.6547	Remote Similarity	NPD1778	Approved
0.6547	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD7157	Approved
0.6541	Remote Similarity	NPD7577	Discontinued
0.6538	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD2354	Approved
0.6536	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD2935	Discontinued
0.6527	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD1481	Phase 2
0.6522	Remote Similarity	NPD7768	Phase 2
0.6519	Remote Similarity	NPD6599	Discontinued
0.6516	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD2182	Approved
0.651	Remote Similarity	NPD5689	Approved
0.651	Remote Similarity	NPD5688	Approved
0.6509	Remote Similarity	NPD6765	Approved
0.6509	Remote Similarity	NPD6764	Approved
0.6503	Remote Similarity	NPD5494	Approved
0.6503	Remote Similarity	NPD6362	Approved
0.6503	Remote Similarity	NPD710	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7819	Suspended
0.65	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7440	Discontinued
0.6489	Remote Similarity	NPD968	Approved
0.6479	Remote Similarity	NPD5327	Phase 3
0.6478	Remote Similarity	NPD7411	Suspended
0.6471	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6233	Phase 2
0.6462	Remote Similarity	NPD164	Approved
0.646	Remote Similarity	NPD5977	Approved
0.646	Remote Similarity	NPD5978	Approved
0.646	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD2651	Approved
0.6456	Remote Similarity	NPD3226	Approved
0.6456	Remote Similarity	NPD2649	Approved
0.6454	Remote Similarity	NPD1611	Approved
0.6454	Remote Similarity	NPD1535	Discovery
0.6452	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5958	Discontinued
0.6444	Remote Similarity	NPD7843	Approved
0.6443	Remote Similarity	NPD6653	Approved
0.6442	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD290	Approved
0.6424	Remote Similarity	NPD2531	Phase 2
0.6424	Remote Similarity	NPD2438	Suspended
0.6423	Remote Similarity	NPD2557	Approved
0.642	Remote Similarity	NPD3882	Suspended
0.6414	Remote Similarity	NPD454	Approved
0.641	Remote Similarity	NPD5401	Approved
0.641	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD6580	Approved
0.6403	Remote Similarity	NPD6581	Approved
0.6398	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD1296	Phase 2
0.6395	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD3596	Phase 2
0.6369	Remote Similarity	NPD2163	Approved
0.6364	Remote Similarity	NPD4110	Phase 3
0.6364	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD7033	Discontinued
0.6358	Remote Similarity	NPD6785	Approved
0.6358	Remote Similarity	NPD6784	Approved
0.6357	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD7458	Discontinued
0.6351	Remote Similarity	NPD4062	Phase 3
0.6351	Remote Similarity	NPD4870	Approved
0.6347	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD5451	Approved
0.634	Remote Similarity	NPD4534	Discontinued
0.6336	Remote Similarity	NPD1237	Approved
0.6335	Remote Similarity	NPD6844	Discontinued
0.6335	Remote Similarity	NPD1934	Approved
0.6333	Remote Similarity	NPD2157	Approved
0.6329	Remote Similarity	NPD5403	Approved
0.6324	Remote Similarity	NPD821	Approved
0.6312	Remote Similarity	NPD4626	Approved
0.6312	Remote Similarity	NPD7028	Phase 2
0.6309	Remote Similarity	NPD4140	Approved
0.6301	Remote Similarity	NPD6734	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD2861	Phase 2

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