NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.13
Volume:	269.992
LogP:	3.221
LogD:	2.774
LogS:	-4.052
# Rotatable Bonds:	6
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.761
Synthetic Accessibility Score:	3.2
Fsp3:	0.267
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.827
MDCK Permeability:	2.2080912458477542e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	96.93326568603516%
Volume Distribution (VD):	0.584
Pgp-substrate:	4.596744060516357%

ADMET: Metabolism

CYP1A2-inhibitor:	0.124
CYP1A2-substrate:	0.54
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.098
CYP2C9-substrate:	0.607
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.278
CYP3A4-inhibitor:	0.034
CYP3A4-substrate:	0.119

ADMET: Excretion

Clearance (CL):	2.116
Half-life (T1/2):	0.934

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.713
Drug-inuced Liver Injury (DILI):	0.745
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.787
Maximum Recommended Daily Dose:	0.094
Skin Sensitization:	0.114
Carcinogencity:	0.786
Eye Corrosion:	0.043
Eye Irritation:	0.717
Respiratory Toxicity:	0.903

Download Data

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

Natural Product: NPC270807

Natural Product ID:	NPC270807
*Common Name:**	5-[(1E,5E)-2,6-Dimethylocta-1,5,7-Trienyl]Furan-3-Carboxylic Acid
IUPAC Name:	5-[(1E,5E)-2,6-dimethylocta-1,5,7-trienyl]furan-3-carboxylic acid
Synonyms:
Standard InCHIKey:	CWSVEYKHSSZGRW-DECBNBDHSA-N
Standard InCHI:	InChI=1S/C15H18O3/c1-4-11(2)6-5-7-12(3)8-14-9-13(10-18-14)15(16)17/h4,6,8-10H,1,5,7H2,2-3H3,(H,16,17)/b11-6+,12-8+
SMILES:	C/C(=Cc1cc(co1)C(=O)O)/CC/C=C(/C=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3087059
PubChem CID:	6382798
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO32605	sinularia kavarattiensis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24144848]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	39800.0	nM	PMID[458497]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	74500.0	nM	PMID[458497]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	80400.0	nM	PMID[458497]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	89700.0	nM	PMID[458497]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	38900.0	nM	PMID[458497]

☑ 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 NPC270807 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	278
0.1-0.2	2249
0.2-0.3	6940
0.3-0.4	11547
0.4-0.5	6154
0.5-0.6	8235
0.6-0.7	6838
0.7-0.8	433
0.8-0.85	17
0.85-0.9	2
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC174915
0.9565	High Similarity	NPC244862
0.9565	High Similarity	NPC67345
0.8824	High Similarity	NPC187547
0.8824	High Similarity	NPC21831
0.8538	High Similarity	NPC159786
0.8362	Intermediate Similarity	NPC140688
0.8333	Intermediate Similarity	NPC292036
0.824	Intermediate Similarity	NPC263870
0.8231	Intermediate Similarity	NPC136340
0.8167	Intermediate Similarity	NPC26157
0.8167	Intermediate Similarity	NPC1811
0.816	Intermediate Similarity	NPC1848
0.8125	Intermediate Similarity	NPC216810
0.8115	Intermediate Similarity	NPC11821
0.8095	Intermediate Similarity	NPC323118
0.8049	Intermediate Similarity	NPC76844
0.8045	Intermediate Similarity	NPC106247
0.8043	Intermediate Similarity	NPC254198
0.8016	Intermediate Similarity	NPC79557
0.7969	Intermediate Similarity	NPC118853
0.7943	Intermediate Similarity	NPC308799
0.7941	Intermediate Similarity	NPC472376
0.7941	Intermediate Similarity	NPC471653
0.7917	Intermediate Similarity	NPC177331
0.7903	Intermediate Similarity	NPC45536
0.7887	Intermediate Similarity	NPC61284
0.7887	Intermediate Similarity	NPC113428
0.7868	Intermediate Similarity	NPC473268
0.7833	Intermediate Similarity	NPC471521
0.7833	Intermediate Similarity	NPC473356
0.7823	Intermediate Similarity	NPC205523
0.7807	Intermediate Similarity	NPC146316
0.7805	Intermediate Similarity	NPC311987
0.7778	Intermediate Similarity	NPC254958
0.7778	Intermediate Similarity	NPC291619
0.7754	Intermediate Similarity	NPC474615
0.7752	Intermediate Similarity	NPC311219
0.7746	Intermediate Similarity	NPC104924
0.7734	Intermediate Similarity	NPC474136
0.7717	Intermediate Similarity	NPC4898
0.7705	Intermediate Similarity	NPC229387
0.7704	Intermediate Similarity	NPC474425
0.7704	Intermediate Similarity	NPC474407
0.7704	Intermediate Similarity	NPC474426
0.7698	Intermediate Similarity	NPC131801
0.7698	Intermediate Similarity	NPC217180
0.7698	Intermediate Similarity	NPC144745
0.7698	Intermediate Similarity	NPC208906
0.7698	Intermediate Similarity	NPC312525
0.7698	Intermediate Similarity	NPC227660
0.7692	Intermediate Similarity	NPC156768
0.7674	Intermediate Similarity	NPC289911
0.7674	Intermediate Similarity	NPC283284
0.7671	Intermediate Similarity	NPC474378
0.7671	Intermediate Similarity	NPC474219
0.7656	Intermediate Similarity	NPC474817
0.7652	Intermediate Similarity	NPC319140
0.7652	Intermediate Similarity	NPC95567
0.7652	Intermediate Similarity	NPC184391
0.7642	Intermediate Similarity	NPC105249
0.7623	Intermediate Similarity	NPC209111
0.7619	Intermediate Similarity	NPC476031
0.7619	Intermediate Similarity	NPC476014
0.7615	Intermediate Similarity	NPC476351
0.7615	Intermediate Similarity	NPC475818
0.7609	Intermediate Similarity	NPC186626
0.7578	Intermediate Similarity	NPC90522
0.7578	Intermediate Similarity	NPC328459
0.7578	Intermediate Similarity	NPC473969
0.7576	Intermediate Similarity	NPC4164
0.7574	Intermediate Similarity	NPC470740
0.7559	Intermediate Similarity	NPC217423
0.7557	Intermediate Similarity	NPC243269
0.7557	Intermediate Similarity	NPC65735
0.7557	Intermediate Similarity	NPC188377
0.7552	Intermediate Similarity	NPC195920
0.7521	Intermediate Similarity	NPC42471
0.7519	Intermediate Similarity	NPC72977
0.7519	Intermediate Similarity	NPC230951
0.7517	Intermediate Similarity	NPC474542
0.75	Intermediate Similarity	NPC75557
0.75	Intermediate Similarity	NPC474829
0.75	Intermediate Similarity	NPC107571
0.75	Intermediate Similarity	NPC475864
0.75	Intermediate Similarity	NPC71274
0.75	Intermediate Similarity	NPC94637
0.7483	Intermediate Similarity	NPC261733
0.7483	Intermediate Similarity	NPC267004
0.7483	Intermediate Similarity	NPC218712
0.7483	Intermediate Similarity	NPC307346
0.7482	Intermediate Similarity	NPC215109
0.7482	Intermediate Similarity	NPC170604
0.7482	Intermediate Similarity	NPC286130
0.7481	Intermediate Similarity	NPC21460
0.748	Intermediate Similarity	NPC474987
0.7479	Intermediate Similarity	NPC217226
0.7478	Intermediate Similarity	NPC265461
0.7478	Intermediate Similarity	NPC233791
0.7463	Intermediate Similarity	NPC474279
0.7463	Intermediate Similarity	NPC71525
0.7463	Intermediate Similarity	NPC474438
0.7444	Intermediate Similarity	NPC474260
0.7444	Intermediate Similarity	NPC81912
0.7444	Intermediate Similarity	NPC329922
0.7444	Intermediate Similarity	NPC329694
0.744	Intermediate Similarity	NPC22678
0.7431	Intermediate Similarity	NPC105381
0.7431	Intermediate Similarity	NPC37488
0.7431	Intermediate Similarity	NPC10302
0.7426	Intermediate Similarity	NPC477645
0.7422	Intermediate Similarity	NPC240664
0.7417	Intermediate Similarity	NPC269495
0.7413	Intermediate Similarity	NPC267632
0.7405	Intermediate Similarity	NPC272487
0.7402	Intermediate Similarity	NPC188907
0.7397	Intermediate Similarity	NPC471618
0.7397	Intermediate Similarity	NPC474255
0.7397	Intermediate Similarity	NPC474220
0.7388	Intermediate Similarity	NPC474830
0.7388	Intermediate Similarity	NPC475236
0.7383	Intermediate Similarity	NPC67654
0.7376	Intermediate Similarity	NPC202260
0.7372	Intermediate Similarity	NPC473982
0.7368	Intermediate Similarity	NPC221798
0.7368	Intermediate Similarity	NPC4012
0.7368	Intermediate Similarity	NPC471559
0.7361	Intermediate Similarity	NPC476164
0.7361	Intermediate Similarity	NPC476310
0.7353	Intermediate Similarity	NPC238309
0.7353	Intermediate Similarity	NPC45947
0.7351	Intermediate Similarity	NPC160015
0.7351	Intermediate Similarity	NPC247677
0.7348	Intermediate Similarity	NPC69403
0.7348	Intermediate Similarity	NPC291189
0.7347	Intermediate Similarity	NPC475904
0.7347	Intermediate Similarity	NPC474270
0.7344	Intermediate Similarity	NPC128825
0.7338	Intermediate Similarity	NPC265793
0.7329	Intermediate Similarity	NPC224418
0.7329	Intermediate Similarity	NPC474317
0.7317	Intermediate Similarity	NPC219969
0.7315	Intermediate Similarity	NPC156244
0.7305	Intermediate Similarity	NPC130976
0.7303	Intermediate Similarity	NPC296957
0.7303	Intermediate Similarity	NPC260902
0.7299	Intermediate Similarity	NPC475092
0.7286	Intermediate Similarity	NPC303217
0.7286	Intermediate Similarity	NPC146872
0.7273	Intermediate Similarity	NPC24761
0.7273	Intermediate Similarity	NPC473379
0.7273	Intermediate Similarity	NPC471549
0.7266	Intermediate Similarity	NPC28054
0.7266	Intermediate Similarity	NPC288209
0.7266	Intermediate Similarity	NPC200718
0.726	Intermediate Similarity	NPC233763
0.7259	Intermediate Similarity	NPC473355
0.7259	Intermediate Similarity	NPC471573
0.7259	Intermediate Similarity	NPC471501
0.7259	Intermediate Similarity	NPC476016
0.7259	Intermediate Similarity	NPC471554
0.7255	Intermediate Similarity	NPC476350
0.7255	Intermediate Similarity	NPC476349
0.7252	Intermediate Similarity	NPC31314
0.7252	Intermediate Similarity	NPC233282
0.7252	Intermediate Similarity	NPC193193
0.7248	Intermediate Similarity	NPC155882
0.7248	Intermediate Similarity	NPC191104
0.7246	Intermediate Similarity	NPC97740
0.7246	Intermediate Similarity	NPC45358
0.7246	Intermediate Similarity	NPC7012
0.7244	Intermediate Similarity	NPC53953
0.7241	Intermediate Similarity	NPC137295
0.7241	Intermediate Similarity	NPC84479
0.7241	Intermediate Similarity	NPC476944
0.7239	Intermediate Similarity	NPC193805
0.7239	Intermediate Similarity	NPC6888
0.7239	Intermediate Similarity	NPC471074
0.7239	Intermediate Similarity	NPC473885
0.7237	Intermediate Similarity	NPC221992
0.7237	Intermediate Similarity	NPC81405
0.7234	Intermediate Similarity	NPC42400
0.7234	Intermediate Similarity	NPC278832
0.7234	Intermediate Similarity	NPC64157
0.7231	Intermediate Similarity	NPC206007
0.723	Intermediate Similarity	NPC211625
0.7219	Intermediate Similarity	NPC158261
0.7219	Intermediate Similarity	NPC42458
0.7214	Intermediate Similarity	NPC92941
0.7214	Intermediate Similarity	NPC14650
0.7209	Intermediate Similarity	NPC33717
0.7209	Intermediate Similarity	NPC328451
0.7208	Intermediate Similarity	NPC260296
0.7208	Intermediate Similarity	NPC169
0.7208	Intermediate Similarity	NPC115432
0.7208	Intermediate Similarity	NPC49009
0.7206	Intermediate Similarity	NPC207294
0.7206	Intermediate Similarity	NPC329707
0.7206	Intermediate Similarity	NPC112706
0.7203	Intermediate Similarity	NPC61157

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 NPC270807 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	1047
0.2-0.3	2163
0.3-0.4	2898
0.4-0.5	1804
0.5-0.6	791
0.6-0.7	194
0.7-0.8	18
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
0.7752	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD1203	Approved
0.7391	Intermediate Similarity	NPD447	Suspended
0.7388	Intermediate Similarity	NPD1019	Discontinued
0.7344	Intermediate Similarity	NPD9493	Approved
0.7305	Intermediate Similarity	NPD1551	Phase 2
0.7279	Intermediate Similarity	NPD6832	Phase 2
0.7254	Intermediate Similarity	NPD2344	Approved
0.7185	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD411	Approved
0.7162	Intermediate Similarity	NPD920	Approved
0.7154	Intermediate Similarity	NPD9092	Discovery
0.7143	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2309	Approved
0.705	Intermediate Similarity	NPD2313	Discontinued
0.7021	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2799	Discontinued
0.6986	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2935	Discontinued
0.6889	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5647	Approved
0.6846	Remote Similarity	NPD6799	Approved
0.6846	Remote Similarity	NPD1241	Discontinued
0.6842	Remote Similarity	NPD9545	Approved
0.6825	Remote Similarity	NPD3134	Approved
0.6812	Remote Similarity	NPD2797	Approved
0.6803	Remote Similarity	NPD1243	Approved
0.6783	Remote Similarity	NPD1933	Approved
0.6781	Remote Similarity	NPD2346	Discontinued
0.6781	Remote Similarity	NPD1471	Phase 3
0.6772	Remote Similarity	NPD9263	Approved
0.6772	Remote Similarity	NPD1358	Approved
0.6772	Remote Similarity	NPD9264	Approved
0.6772	Remote Similarity	NPD9267	Approved
0.6753	Remote Similarity	NPD7411	Suspended
0.6741	Remote Similarity	NPD1778	Approved
0.6735	Remote Similarity	NPD1549	Phase 2
0.6719	Remote Similarity	NPD74	Approved
0.6719	Remote Similarity	NPD9266	Approved
0.6714	Remote Similarity	NPD9494	Approved
0.6713	Remote Similarity	NPD1240	Approved
0.6711	Remote Similarity	NPD5403	Approved
0.6691	Remote Similarity	NPD3496	Discontinued
0.669	Remote Similarity	NPD3268	Approved
0.6689	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6559	Discontinued
0.6646	Remote Similarity	NPD3749	Approved
0.6644	Remote Similarity	NPD4308	Phase 3
0.6643	Remote Similarity	NPD2798	Approved
0.6624	Remote Similarity	NPD5402	Approved
0.6623	Remote Similarity	NPD3226	Approved
0.6621	Remote Similarity	NPD1607	Approved
0.6619	Remote Similarity	NPD3225	Approved
0.6604	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD919	Approved
0.6599	Remote Similarity	NPD2796	Approved
0.6584	Remote Similarity	NPD6808	Phase 2
0.6582	Remote Similarity	NPD3882	Suspended
0.6581	Remote Similarity	NPD6599	Discontinued
0.6579	Remote Similarity	NPD2532	Approved
0.6579	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD2534	Approved
0.6579	Remote Similarity	NPD2533	Approved
0.6579	Remote Similarity	NPD5401	Approved
0.6571	Remote Similarity	NPD6362	Approved
0.6568	Remote Similarity	NPD8434	Phase 2
0.6561	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD7819	Suspended
0.6544	Remote Similarity	NPD5585	Approved
0.6541	Remote Similarity	NPD7075	Discontinued
0.6533	Remote Similarity	NPD4628	Phase 3
0.6531	Remote Similarity	NPD7033	Discontinued
0.6531	Remote Similarity	NPD1510	Phase 2
0.6522	Remote Similarity	NPD422	Phase 1
0.6519	Remote Similarity	NPD2296	Approved
0.651	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD6653	Approved
0.6497	Remote Similarity	NPD6801	Discontinued
0.6497	Remote Similarity	NPD6279	Approved
0.6497	Remote Similarity	NPD6280	Approved
0.6489	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD9697	Approved
0.6478	Remote Similarity	NPD7768	Phase 2
0.6475	Remote Similarity	NPD1481	Phase 2
0.6471	Remote Similarity	NPD1894	Discontinued
0.6467	Remote Similarity	NPD2800	Approved
0.6462	Remote Similarity	NPD2182	Approved
0.6458	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD9261	Approved
0.6456	Remote Similarity	NPD5761	Phase 2
0.6456	Remote Similarity	NPD5760	Phase 2
0.6447	Remote Similarity	NPD7440	Discontinued
0.6438	Remote Similarity	NPD230	Phase 1
0.6434	Remote Similarity	NPD968	Approved
0.6424	Remote Similarity	NPD3750	Approved
0.642	Remote Similarity	NPD1247	Approved
0.6418	Remote Similarity	NPD9281	Approved
0.6415	Remote Similarity	NPD3817	Phase 2
0.6414	Remote Similarity	NPD6233	Phase 2
0.6403	Remote Similarity	NPD1535	Discovery
0.6385	Remote Similarity	NPD290	Approved
0.6383	Remote Similarity	NPD1876	Approved
0.637	Remote Similarity	NPD4307	Phase 2
0.6364	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD3972	Approved
0.6357	Remote Similarity	NPD1608	Approved
0.6352	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD2801	Approved
0.6338	Remote Similarity	NPD3267	Approved
0.6338	Remote Similarity	NPD3266	Approved
0.6335	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6002	Phase 3
0.6333	Remote Similarity	NPD6005	Phase 3
0.6333	Remote Similarity	NPD6004	Phase 3
0.6325	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD3818	Discontinued
0.6323	Remote Similarity	NPD6273	Approved
0.6312	Remote Similarity	NPD4359	Approved
0.6312	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.631	Remote Similarity	NPD5953	Discontinued
0.6306	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD520	Approved
0.6299	Remote Similarity	NPD1511	Approved
0.6291	Remote Similarity	NPD2424	Discontinued
0.6289	Remote Similarity	NPD6844	Discontinued
0.6289	Remote Similarity	NPD1934	Approved
0.6287	Remote Similarity	NPD7286	Phase 2
0.6279	Remote Similarity	NPD164	Approved
0.6266	Remote Similarity	NPD4380	Phase 2
0.6259	Remote Similarity	NPD3142	Approved
0.6259	Remote Similarity	NPD3140	Approved
0.6258	Remote Similarity	NPD4662	Approved
0.6258	Remote Similarity	NPD4661	Approved
0.625	Remote Similarity	NPD454	Approved
0.6242	Remote Similarity	NPD7097	Phase 1
0.6242	Remote Similarity	NPD3926	Phase 2
0.6233	Remote Similarity	NPD3764	Approved
0.6233	Remote Similarity	NPD1048	Approved
0.6233	Remote Similarity	NPD6798	Discontinued
0.6226	Remote Similarity	NPD5889	Approved
0.6226	Remote Similarity	NPD5890	Approved
0.6222	Remote Similarity	NPD9069	Phase 1
0.622	Remote Similarity	NPD1238	Approved
0.6218	Remote Similarity	NPD1512	Approved
0.6216	Remote Similarity	NPD6355	Discontinued
0.6214	Remote Similarity	NPD3847	Discontinued
0.6212	Remote Similarity	NPD2684	Approved
0.6211	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD1562	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD405	Clinical (unspecified phase)
0.62	Remote Similarity	NPD3748	Approved
0.619	Remote Similarity	NPD4062	Phase 3
0.6182	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.617	Remote Similarity	NPD1091	Approved
0.6169	Remote Similarity	NPD2354	Approved
0.6169	Remote Similarity	NPD3887	Approved
0.6159	Remote Similarity	NPD5494	Approved
0.6159	Remote Similarity	NPD5536	Phase 2
0.6159	Remote Similarity	NPD2862	Discontinued
0.6159	Remote Similarity	NPD6032	Approved
0.6149	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD821	Approved
0.6148	Remote Similarity	NPD5535	Approved
0.6143	Remote Similarity	NPD17	Approved
0.6143	Remote Similarity	NPD4626	Approved
0.6136	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD2366	Approved
0.6122	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1164	Approved
0.6107	Remote Similarity	NPD4622	Approved
0.6107	Remote Similarity	NPD4618	Approved
0.6104	Remote Similarity	NPD7003	Approved
0.6104	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD6232	Discontinued
0.6082	Remote Similarity	NPD6764	Approved
0.6082	Remote Similarity	NPD6765	Approved
0.6071	Remote Similarity	NPD5691	Approved
0.6071	Remote Similarity	NPD7473	Discontinued
0.6069	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD6585	Discontinued
0.6059	Remote Similarity	NPD1729	Discontinued
0.6054	Remote Similarity	NPD5163	Phase 2
0.6054	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD4477	Approved
0.6053	Remote Similarity	NPD4476	Approved
0.6053	Remote Similarity	NPD5712	Approved
0.6051	Remote Similarity	NPD1578	Phase 2
0.6051	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD7972	Discontinued
0.6048	Remote Similarity	NPD9365	Approved
0.6047	Remote Similarity	NPD4338	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