NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.09
Volume:	267.538
LogP:	4.411
LogD:	3.743
LogS:	-6.255
# Rotatable Bonds:	2
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.617
Synthetic Accessibility Score:	2.218
Fsp3:	0.188
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:	-4.731
MDCK Permeability:	2.864736416086089e-05
Pgp-inhibitor:	0.062
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.869
30% Bioavailability (F30%):	0.891

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	97.54949188232422%
Volume Distribution (VD):	0.965
Pgp-substrate:	2.086888551712036%

ADMET: Metabolism

CYP1A2-inhibitor:	0.952
CYP1A2-substrate:	0.94
CYP2C19-inhibitor:	0.89
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.539
CYP2C9-substrate:	0.864
CYP2D6-inhibitor:	0.776
CYP2D6-substrate:	0.925
CYP3A4-inhibitor:	0.76
CYP3A4-substrate:	0.241

ADMET: Excretion

Clearance (CL):	10.408
Half-life (T1/2):	0.126

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.396
Drug-inuced Liver Injury (DILI):	0.86
AMES Toxicity:	0.062
Rat Oral Acute Toxicity:	0.268
Maximum Recommended Daily Dose:	0.468
Skin Sensitization:	0.091
Carcinogencity:	0.674
Eye Corrosion:	0.004
Eye Irritation:	0.576
Respiratory Toxicity:	0.203

Download Data

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

Natural Product: NPC475092

Natural Product ID:	NPC475092
*Common Name:**	11-Carbomethoxylinderazulene
IUPAC Name:	methyl 1,5-dimethylazuleno[6,7-b]furan-8-carboxylate
Synonyms:	11-Carbomethoxylinderazulene
Standard InCHIKey:	IRGLEIHRANDEHS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O3/c1-9-6-15-13(10(2)8-19-15)7-14-11(9)4-5-12(14)16(17)18-3/h4-8H,1-3H3
SMILES:	COC(=O)c1ccc2c1cc1c(C)coc1cc2C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497241
PubChem CID:	656394
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]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	2.7	ug.mL-1	PMID[548247]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	18.7	ug.mL-1	PMID[548247]

☑ 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 NPC475092 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	313
0.1-0.2	1755
0.2-0.3	4701
0.3-0.4	10889
0.4-0.5	8056
0.5-0.6	7910
0.6-0.7	7983
0.7-0.8	1015
0.8-0.85	70
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9675	High Similarity	NPC141059
0.9593	High Similarity	NPC83301
0.8583	High Similarity	NPC115859
0.8425	Intermediate Similarity	NPC137710
0.8413	Intermediate Similarity	NPC227660
0.8385	Intermediate Similarity	NPC118853
0.8346	Intermediate Similarity	NPC206007
0.8281	Intermediate Similarity	NPC473969
0.8254	Intermediate Similarity	NPC28054
0.8254	Intermediate Similarity	NPC205523
0.8244	Intermediate Similarity	NPC65735
0.8244	Intermediate Similarity	NPC188377
0.8217	Intermediate Similarity	NPC246214
0.8203	Intermediate Similarity	NPC21831
0.8203	Intermediate Similarity	NPC187547
0.8182	Intermediate Similarity	NPC247221
0.8125	Intermediate Similarity	NPC312525
0.8125	Intermediate Similarity	NPC131801
0.8125	Intermediate Similarity	NPC217180
0.808	Intermediate Similarity	NPC105249
0.8074	Intermediate Similarity	NPC50583
0.8047	Intermediate Similarity	NPC476031
0.8047	Intermediate Similarity	NPC476014
0.8045	Intermediate Similarity	NPC473885
0.8045	Intermediate Similarity	NPC471074
0.8016	Intermediate Similarity	NPC22678
0.8	Intermediate Similarity	NPC215109
0.8	Intermediate Similarity	NPC307401
0.8	Intermediate Similarity	NPC170604
0.8	Intermediate Similarity	NPC4898
0.7986	Intermediate Similarity	NPC209858
0.7985	Intermediate Similarity	NPC216810
0.7984	Intermediate Similarity	NPC144745
0.7984	Intermediate Similarity	NPC208906
0.797	Intermediate Similarity	NPC243269
0.7967	Intermediate Similarity	NPC42471
0.7956	Intermediate Similarity	NPC183348
0.7956	Intermediate Similarity	NPC136340
0.7956	Intermediate Similarity	NPC282230
0.7931	Intermediate Similarity	NPC290038
0.7931	Intermediate Similarity	NPC56731
0.791	Intermediate Similarity	NPC71274
0.791	Intermediate Similarity	NPC75557
0.7907	Intermediate Similarity	NPC59035
0.7907	Intermediate Similarity	NPC79202
0.7899	Intermediate Similarity	NPC470977
0.7899	Intermediate Similarity	NPC15083
0.7899	Intermediate Similarity	NPC470976
0.7899	Intermediate Similarity	NPC196979
0.7895	Intermediate Similarity	NPC16922
0.7887	Intermediate Similarity	NPC202260
0.7883	Intermediate Similarity	NPC170546
0.7883	Intermediate Similarity	NPC66246
0.7879	Intermediate Similarity	NPC97566
0.7868	Intermediate Similarity	NPC474279
0.7868	Intermediate Similarity	NPC474438
0.7867	Intermediate Similarity	NPC471863
0.7857	Intermediate Similarity	NPC265793
0.7852	Intermediate Similarity	NPC474260
0.7852	Intermediate Similarity	NPC81912
0.7852	Intermediate Similarity	NPC329694
0.7852	Intermediate Similarity	NPC329922
0.7842	Intermediate Similarity	NPC293253
0.784	Intermediate Similarity	NPC473356
0.784	Intermediate Similarity	NPC471521
0.7836	Intermediate Similarity	NPC141252
0.7836	Intermediate Similarity	NPC11799
0.7823	Intermediate Similarity	NPC224418
0.7823	Intermediate Similarity	NPC308799
0.781	Intermediate Similarity	NPC59502
0.7794	Intermediate Similarity	NPC476016
0.7786	Intermediate Similarity	NPC106247
0.7786	Intermediate Similarity	NPC291619
0.7786	Intermediate Similarity	NPC254958
0.7786	Intermediate Similarity	NPC243704
0.7786	Intermediate Similarity	NPC293424
0.7778	Intermediate Similarity	NPC179354
0.7778	Intermediate Similarity	NPC474829
0.777	Intermediate Similarity	NPC125153
0.777	Intermediate Similarity	NPC113428
0.777	Intermediate Similarity	NPC61284
0.777	Intermediate Similarity	NPC93666
0.777	Intermediate Similarity	NPC473982
0.7769	Intermediate Similarity	NPC470860
0.7769	Intermediate Similarity	NPC316062
0.7769	Intermediate Similarity	NPC45536
0.7762	Intermediate Similarity	NPC233707
0.7761	Intermediate Similarity	NPC476351
0.7755	Intermediate Similarity	NPC208584
0.7752	Intermediate Similarity	NPC292036
0.7752	Intermediate Similarity	NPC252004
0.7746	Intermediate Similarity	NPC278832
0.7746	Intermediate Similarity	NPC64157
0.774	Intermediate Similarity	NPC261733
0.774	Intermediate Similarity	NPC307346
0.774	Intermediate Similarity	NPC267004
0.774	Intermediate Similarity	NPC218712
0.773	Intermediate Similarity	NPC324117
0.773	Intermediate Similarity	NPC159786
0.7721	Intermediate Similarity	NPC470858
0.7721	Intermediate Similarity	NPC138139
0.7721	Intermediate Similarity	NPC46536
0.7721	Intermediate Similarity	NPC74612
0.7718	Intermediate Similarity	NPC266743
0.7718	Intermediate Similarity	NPC95526
0.7714	Intermediate Similarity	NPC470740
0.771	Intermediate Similarity	NPC45104
0.7708	Intermediate Similarity	NPC148374
0.7698	Intermediate Similarity	NPC298190
0.7697	Intermediate Similarity	NPC25351
0.7692	Intermediate Similarity	NPC150895
0.7692	Intermediate Similarity	NPC130976
0.7687	Intermediate Similarity	NPC283284
0.7687	Intermediate Similarity	NPC27798
0.7687	Intermediate Similarity	NPC93241
0.7687	Intermediate Similarity	NPC289911
0.7681	Intermediate Similarity	NPC208389
0.7676	Intermediate Similarity	NPC303217
0.7667	Intermediate Similarity	NPC472298
0.7667	Intermediate Similarity	NPC88445
0.7664	Intermediate Similarity	NPC83178
0.7664	Intermediate Similarity	NPC137570
0.7664	Intermediate Similarity	NPC319140
0.7664	Intermediate Similarity	NPC95567
0.7664	Intermediate Similarity	NPC474830
0.7656	Intermediate Similarity	NPC54626
0.7647	Intermediate Similarity	NPC107846
0.7639	Intermediate Similarity	NPC474615
0.7639	Intermediate Similarity	NPC62735
0.7632	Intermediate Similarity	NPC24232
0.763	Intermediate Similarity	NPC475818
0.7626	Intermediate Similarity	NPC21460
0.7622	Intermediate Similarity	NPC286130
0.7622	Intermediate Similarity	NPC163029
0.7622	Intermediate Similarity	NPC473268
0.7619	Intermediate Similarity	NPC51146
0.7619	Intermediate Similarity	NPC117674
0.7619	Intermediate Similarity	NPC166858
0.7616	Intermediate Similarity	NPC191104
0.7616	Intermediate Similarity	NPC144010
0.7612	Intermediate Similarity	NPC1848
0.7612	Intermediate Similarity	NPC474136
0.7612	Intermediate Similarity	NPC79557
0.7609	Intermediate Similarity	NPC207294
0.7609	Intermediate Similarity	NPC329707
0.7609	Intermediate Similarity	NPC112706
0.7597	Intermediate Similarity	NPC1811
0.7597	Intermediate Similarity	NPC26157
0.7594	Intermediate Similarity	NPC67345
0.7594	Intermediate Similarity	NPC244862
0.7591	Intermediate Similarity	NPC52035
0.7589	Intermediate Similarity	NPC471006
0.7586	Intermediate Similarity	NPC56197
0.7576	Intermediate Similarity	NPC217423
0.7576	Intermediate Similarity	NPC469954
0.7571	Intermediate Similarity	NPC477645
0.7561	Intermediate Similarity	NPC156768
0.7557	Intermediate Similarity	NPC11821
0.7556	Intermediate Similarity	NPC314329
0.7552	Intermediate Similarity	NPC146872
0.7552	Intermediate Similarity	NPC204592
0.7551	Intermediate Similarity	NPC470273
0.7551	Intermediate Similarity	NPC80635
0.7551	Intermediate Similarity	NPC27220
0.7538	Intermediate Similarity	NPC53953
0.7537	Intermediate Similarity	NPC230951
0.7536	Intermediate Similarity	NPC184391
0.7533	Intermediate Similarity	NPC198427
0.7533	Intermediate Similarity	NPC74539
0.7533	Intermediate Similarity	NPC304443
0.7532	Intermediate Similarity	NPC474542
0.7519	Intermediate Similarity	NPC23332
0.7519	Intermediate Similarity	NPC57879
0.7518	Intermediate Similarity	NPC471817
0.7518	Intermediate Similarity	NPC221798
0.7518	Intermediate Similarity	NPC471559
0.7517	Intermediate Similarity	NPC478166
0.7517	Intermediate Similarity	NPC107571
0.7517	Intermediate Similarity	NPC246903
0.7516	Intermediate Similarity	NPC44606
0.7516	Intermediate Similarity	NPC10429
0.75	Intermediate Similarity	NPC472406
0.75	Intermediate Similarity	NPC474987
0.75	Intermediate Similarity	NPC69403
0.75	Intermediate Similarity	NPC939
0.75	Intermediate Similarity	NPC259554
0.75	Intermediate Similarity	NPC291189
0.75	Intermediate Similarity	NPC76844
0.7483	Intermediate Similarity	NPC92941
0.7482	Intermediate Similarity	NPC161322
0.7482	Intermediate Similarity	NPC428300
0.7468	Intermediate Similarity	NPC261184
0.7468	Intermediate Similarity	NPC131725
0.7467	Intermediate Similarity	NPC71821
0.7467	Intermediate Similarity	NPC281398
0.7466	Intermediate Similarity	NPC282973
0.7465	Intermediate Similarity	NPC474426
0.7465	Intermediate Similarity	NPC474425
0.7465	Intermediate Similarity	NPC474407
0.7463	Intermediate Similarity	NPC201284

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 NPC475092 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	1081
0.2-0.3	1485
0.3-0.4	2727
0.4-0.5	2018
0.5-0.6	1128
0.6-0.7	354
0.7-0.8	66
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
0.8406	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD1876	Approved
0.7674	Intermediate Similarity	NPD1241	Discontinued
0.7639	Intermediate Similarity	NPD2344	Approved
0.7619	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6832	Phase 2
0.7533	Intermediate Similarity	NPD920	Approved
0.7517	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2799	Discontinued
0.7432	Intermediate Similarity	NPD2309	Approved
0.7415	Intermediate Similarity	NPD1243	Approved
0.7407	Intermediate Similarity	NPD17	Approved
0.7372	Intermediate Similarity	NPD3972	Approved
0.7351	Intermediate Similarity	NPD6273	Approved
0.7343	Intermediate Similarity	NPD4307	Phase 2
0.7338	Intermediate Similarity	NPD3267	Approved
0.7338	Intermediate Similarity	NPD3266	Approved
0.7324	Intermediate Similarity	NPD2313	Discontinued
0.7308	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1019	Discontinued
0.7286	Intermediate Similarity	NPD2798	Approved
0.726	Intermediate Similarity	NPD3748	Approved
0.7248	Intermediate Similarity	NPD4628	Phase 3
0.7246	Intermediate Similarity	NPD1608	Approved
0.7246	Intermediate Similarity	NPD9717	Approved
0.7214	Intermediate Similarity	NPD2797	Approved
0.7206	Intermediate Similarity	NPD5585	Approved
0.719	Intermediate Similarity	NPD3869	Phase 3
0.719	Intermediate Similarity	NPD3873	Phase 3
0.7179	Intermediate Similarity	NPD6279	Approved
0.7179	Intermediate Similarity	NPD6280	Approved
0.7174	Intermediate Similarity	NPD1281	Approved
0.7172	Intermediate Similarity	NPD6355	Discontinued
0.717	Intermediate Similarity	NPD919	Approved
0.7162	Intermediate Similarity	NPD2346	Discontinued
0.7162	Intermediate Similarity	NPD1471	Phase 3
0.7153	Intermediate Similarity	NPD8032	Phase 2
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD6808	Phase 2
0.7132	Intermediate Similarity	NPD3134	Approved
0.7132	Intermediate Similarity	NPD1894	Discontinued
0.7095	Intermediate Similarity	NPD1551	Phase 2
0.7095	Intermediate Similarity	NPD2796	Approved
0.7092	Intermediate Similarity	NPD1203	Approved
0.7086	Intermediate Similarity	NPD3887	Approved
0.7083	Intermediate Similarity	NPD3268	Approved
0.7083	Intermediate Similarity	NPD3764	Approved
0.7055	Intermediate Similarity	NPD1933	Approved
0.7047	Intermediate Similarity	NPD6002	Phase 3
0.7047	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2353	Approved
0.7047	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6004	Phase 3
0.7047	Intermediate Similarity	NPD6005	Phase 3
0.7042	Intermediate Similarity	NPD5647	Approved
0.7021	Intermediate Similarity	NPD1283	Approved
0.702	Intermediate Similarity	NPD7003	Approved
0.702	Intermediate Similarity	NPD3750	Approved
0.7007	Intermediate Similarity	NPD9545	Approved
0.7	Intermediate Similarity	NPD3749	Approved
0.6987	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3140	Approved
0.6986	Remote Similarity	NPD2979	Phase 3
0.6986	Remote Similarity	NPD3142	Approved
0.698	Remote Similarity	NPD4476	Approved
0.698	Remote Similarity	NPD4477	Approved
0.6978	Remote Similarity	NPD3496	Discontinued
0.697	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6798	Discontinued
0.6957	Remote Similarity	NPD5691	Approved
0.6957	Remote Similarity	NPD1651	Approved
0.695	Remote Similarity	NPD4359	Approved
0.6947	Remote Similarity	NPD1358	Approved
0.694	Remote Similarity	NPD5535	Approved
0.6939	Remote Similarity	NPD4622	Approved
0.6939	Remote Similarity	NPD4618	Approved
0.6929	Remote Similarity	NPD1238	Approved
0.6923	Remote Similarity	NPD9697	Approved
0.6894	Remote Similarity	NPD2182	Approved
0.6887	Remote Similarity	NPD2897	Discontinued
0.6883	Remote Similarity	NPD6799	Approved
0.6875	Remote Similarity	NPD2296	Approved
0.6867	Remote Similarity	NPD2935	Discontinued
0.6863	Remote Similarity	NPD2354	Approved
0.6861	Remote Similarity	NPD9493	Approved
0.6859	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6362	Approved
0.6849	Remote Similarity	NPD411	Approved
0.6846	Remote Similarity	NPD5689	Approved
0.6846	Remote Similarity	NPD5688	Approved
0.6839	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6599	Discontinued
0.6832	Remote Similarity	NPD7768	Phase 2
0.6832	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD447	Suspended
0.6818	Remote Similarity	NPD7440	Discontinued
0.6813	Remote Similarity	NPD7819	Suspended
0.6805	Remote Similarity	NPD6765	Approved
0.6805	Remote Similarity	NPD6764	Approved
0.6805	Remote Similarity	NPD6559	Discontinued
0.6803	Remote Similarity	NPD6233	Phase 2
0.6797	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7411	Suspended
0.6786	Remote Similarity	NPD1778	Approved
0.6779	Remote Similarity	NPD6653	Approved
0.6776	Remote Similarity	NPD5958	Discontinued
0.6774	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3226	Approved
0.6768	Remote Similarity	NPD1247	Approved
0.6761	Remote Similarity	NPD1481	Phase 2
0.6759	Remote Similarity	NPD9494	Approved
0.6755	Remote Similarity	NPD2438	Suspended
0.6755	Remote Similarity	NPD2531	Phase 2
0.6748	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5401	Approved
0.6718	Remote Similarity	NPD164	Approved
0.6715	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1535	Discovery
0.669	Remote Similarity	NPD1611	Approved
0.6689	Remote Similarity	NPD4062	Phase 3
0.6689	Remote Similarity	NPD4870	Approved
0.6689	Remote Similarity	NPD7033	Discontinued
0.6688	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4110	Phase 3
0.6687	Remote Similarity	NPD3926	Phase 2
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD4534	Discontinued
0.6667	Remote Similarity	NPD4626	Approved
0.6647	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6784	Approved
0.6647	Remote Similarity	NPD6785	Approved
0.6646	Remote Similarity	NPD5403	Approved
0.6644	Remote Similarity	NPD1240	Approved
0.6644	Remote Similarity	NPD4140	Approved
0.6644	Remote Similarity	NPD454	Approved
0.6642	Remote Similarity	NPD2684	Approved
0.6624	Remote Similarity	NPD4662	Approved
0.6624	Remote Similarity	NPD4661	Approved
0.6622	Remote Similarity	NPD1296	Phase 2
0.662	Remote Similarity	NPD3847	Discontinued
0.6618	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD5760	Phase 2
0.6605	Remote Similarity	NPD5761	Phase 2
0.6601	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7075	Discontinued
0.6584	Remote Similarity	NPD5890	Approved
0.6584	Remote Similarity	NPD5889	Approved
0.6582	Remote Similarity	NPD5049	Phase 3
0.6579	Remote Similarity	NPD1510	Phase 2
0.6575	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6287	Discontinued
0.6571	Remote Similarity	NPD5536	Phase 2
0.6571	Remote Similarity	NPD9092	Discovery
0.6566	Remote Similarity	NPD7199	Phase 2
0.6556	Remote Similarity	NPD1607	Approved
0.6554	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD7095	Approved
0.6552	Remote Similarity	NPD3225	Approved
0.6549	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD7157	Approved
0.6543	Remote Similarity	NPD6801	Discontinued
0.6543	Remote Similarity	NPD7577	Discontinued
0.6541	Remote Similarity	NPD7427	Discontinued
0.6541	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD9261	Approved
0.6514	Remote Similarity	NPD8434	Phase 2
0.6506	Remote Similarity	NPD5494	Approved
0.6503	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.65	Remote Similarity	NPD957	Approved
0.6494	Remote Similarity	NPD5763	Approved
0.6494	Remote Similarity	NPD5762	Approved
0.6488	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD2614	Approved
0.6485	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD5327	Phase 3
0.6479	Remote Similarity	NPD3443	Approved
0.6479	Remote Similarity	NPD3445	Approved
0.6479	Remote Similarity	NPD3444	Approved
0.6478	Remote Similarity	NPD2186	Approved
0.6474	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2067	Discontinued
0.6471	Remote Similarity	NPD7177	Discontinued
0.6467	Remote Similarity	NPD8127	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