NPASS Compound

Structure

NPC471647 OpenBabel07101719132D 25 26 0 0 0 0 0 0 0 0999 V2000 -5.2469 -1.2474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0604 0.5797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3135 2.6931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6591 -0.4384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4836 1.1796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4781 1.2841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8958 1.9886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 -0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0659 0.4751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9013 1.8841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 0.2024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 1.2024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 2.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 2 6 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 17 1 0 0 0 0 6 22 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 17 2 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 23 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 15 20 2 0 0 0 0 16 19 2 0 0 0 0 16 25 1 0 0 0 0 19 21 1 0 0 0 0 20 25 1 0 0 0 0 21 23 1 0 0 0 0 21 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.23
Volume:	378.414
LogP:	3.897
LogD:	3.749
LogS:	-3.887
# Rotatable Bonds:	8
TPSA:	36.69
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.69
Synthetic Accessibility Score:	3.008
Fsp3:	0.476
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:	-4.642
MDCK Permeability:	1.0380361345596611e-05
Pgp-inhibitor:	0.23
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.078

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.942
Plasma Protein Binding (PPB):	77.46672821044922%
Volume Distribution (VD):	1.814
Pgp-substrate:	13.33649730682373%

ADMET: Metabolism

CYP1A2-inhibitor:	0.115
CYP1A2-substrate:	0.34
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.724
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.218
CYP2D6-inhibitor:	0.633
CYP2D6-substrate:	0.894
CYP3A4-inhibitor:	0.06
CYP3A4-substrate:	0.241

ADMET: Excretion

Clearance (CL):	6.877
Half-life (T1/2):	0.415

ADMET: Toxicity

hERG Blockers:	0.925
Human Hepatotoxicity (H-HT):	0.655
Drug-inuced Liver Injury (DILI):	0.321
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.924
Maximum Recommended Daily Dose:	0.648
Skin Sensitization:	0.327
Carcinogencity:	0.36
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC471647

Natural Product ID:	NPC471647
*Common Name:**	(5-((1E,5Z)-2,6-Dimethylocta-1,5,7-Trienyl)Furan-3-Yl)(4-Ethylpiperazin-1-Yl)Methanone
IUPAC Name:	[5-[(1E,5Z)-2,6-dimethylocta-1,5,7-trienyl]furan-3-yl]-(4-ethylpiperazin-1-yl)methanone
Synonyms:
Standard InCHIKey:	PREPUTJROSKPDO-UZCYSTGLSA-N
Standard InCHI:	InChI=1S/C21H30N2O2/c1-5-17(3)8-7-9-18(4)14-20-15-19(16-25-20)21(24)23-12-10-22(6-2)11-13-23/h5,8,14-16H,1,6-7,9-13H2,2-4H3/b17-8-,18-14+
SMILES:	CCN1CCN(CC1)C(=O)C2=COC(=C2)C=C(C)CCC=C(C)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3087063
PubChem CID:	72543910
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	=	26500.0	nM	PMID[496368]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	30300.0	nM	PMID[496368]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	35900.0	nM	PMID[496368]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	27900.0	nM	PMID[496368]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	20400.0	nM	PMID[496368]

☑ 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 NPC471647 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	243
0.1-0.2	3053
0.2-0.3	11086
0.3-0.4	6959
0.4-0.5	13886
0.5-0.6	7181
0.6-0.7	273
0.7-0.8	10
0.8-0.85	1
0.85-0.9	1
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471646
0.9444	High Similarity	NPC471649
0.8947	High Similarity	NPC471651
0.8831	High Similarity	NPC471648
0.8144	Intermediate Similarity	NPC471650
0.7826	Intermediate Similarity	NPC471652
0.755	Intermediate Similarity	NPC216149
0.755	Intermediate Similarity	NPC208170
0.7394	Intermediate Similarity	NPC67345
0.7394	Intermediate Similarity	NPC244862
0.7371	Intermediate Similarity	NPC45389
0.7342	Intermediate Similarity	NPC223873
0.7285	Intermediate Similarity	NPC266425
0.7268	Intermediate Similarity	NPC41216
0.7179	Intermediate Similarity	NPC26589
0.7179	Intermediate Similarity	NPC473444
0.7123	Intermediate Similarity	NPC270807
0.7123	Intermediate Similarity	NPC174915
0.7088	Intermediate Similarity	NPC112937
0.7029	Intermediate Similarity	NPC140688
0.6943	Remote Similarity	NPC471653
0.6923	Remote Similarity	NPC307682
0.6875	Remote Similarity	NPC205523
0.6855	Remote Similarity	NPC325857
0.6786	Remote Similarity	NPC476443
0.6786	Remote Similarity	NPC133817
0.6781	Remote Similarity	NPC217180
0.6781	Remote Similarity	NPC312525
0.6735	Remote Similarity	NPC21831
0.6735	Remote Similarity	NPC187547
0.6712	Remote Similarity	NPC45536
0.669	Remote Similarity	NPC292036
0.6687	Remote Similarity	NPC189908
0.6686	Remote Similarity	NPC176304
0.6686	Remote Similarity	NPC70840
0.6686	Remote Similarity	NPC473245
0.6667	Remote Similarity	NPC470708
0.6647	Remote Similarity	NPC119669
0.6624	Remote Similarity	NPC132308
0.6585	Remote Similarity	NPC286692
0.6573	Remote Similarity	NPC469964
0.6573	Remote Similarity	NPC476236
0.6573	Remote Similarity	NPC472474
0.6558	Remote Similarity	NPC218323
0.6558	Remote Similarity	NPC184391
0.6556	Remote Similarity	NPC314659
0.6544	Remote Similarity	NPC146316
0.6541	Remote Similarity	NPC196708
0.6538	Remote Similarity	NPC116007
0.6536	Remote Similarity	NPC222524
0.6524	Remote Similarity	NPC477258
0.65	Remote Similarity	NPC106606
0.65	Remote Similarity	NPC197335
0.6497	Remote Similarity	NPC136340
0.649	Remote Similarity	NPC79557
0.6475	Remote Similarity	NPC156768
0.6474	Remote Similarity	NPC283079
0.6471	Remote Similarity	NPC118853
0.6467	Remote Similarity	NPC169387
0.6467	Remote Similarity	NPC477259
0.6464	Remote Similarity	NPC27887
0.646	Remote Similarity	NPC470707
0.6448	Remote Similarity	NPC87391
0.6446	Remote Similarity	NPC296085
0.6438	Remote Similarity	NPC196609
0.6438	Remote Similarity	NPC230698
0.6438	Remote Similarity	NPC73883
0.6438	Remote Similarity	NPC277042
0.6438	Remote Similarity	NPC255817
0.6438	Remote Similarity	NPC136330
0.6438	Remote Similarity	NPC205178
0.6438	Remote Similarity	NPC251454
0.6429	Remote Similarity	NPC289167
0.6429	Remote Similarity	NPC186957
0.6429	Remote Similarity	NPC76433
0.6415	Remote Similarity	NPC470740
0.6398	Remote Similarity	NPC99078
0.6392	Remote Similarity	NPC477645
0.6389	Remote Similarity	NPC471521
0.6389	Remote Similarity	NPC473356
0.6386	Remote Similarity	NPC469978
0.6384	Remote Similarity	NPC284842
0.6382	Remote Similarity	NPC1848
0.6379	Remote Similarity	NPC135006
0.6375	Remote Similarity	NPC167096
0.6375	Remote Similarity	NPC106247
0.6374	Remote Similarity	NPC99723
0.6364	Remote Similarity	NPC42471
0.6359	Remote Similarity	NPC297647
0.6359	Remote Similarity	NPC83511
0.6358	Remote Similarity	NPC252107
0.6358	Remote Similarity	NPC4898
0.6358	Remote Similarity	NPC471316
0.6358	Remote Similarity	NPC220923
0.6347	Remote Similarity	NPC71629
0.6345	Remote Similarity	NPC177331
0.634	Remote Similarity	NPC26285
0.634	Remote Similarity	NPC263870
0.6335	Remote Similarity	NPC180647
0.6335	Remote Similarity	NPC159786
0.6333	Remote Similarity	NPC227660
0.6333	Remote Similarity	NPC131801
0.6327	Remote Similarity	NPC22678
0.6323	Remote Similarity	NPC471074
0.6323	Remote Similarity	NPC473885
0.6319	Remote Similarity	NPC270301
0.6312	Remote Similarity	NPC217226
0.6312	Remote Similarity	NPC169766
0.631	Remote Similarity	NPC324081
0.6309	Remote Similarity	NPC28054
0.6304	Remote Similarity	NPC473007
0.6304	Remote Similarity	NPC128683
0.6301	Remote Similarity	NPC301163
0.6291	Remote Similarity	NPC243704
0.6291	Remote Similarity	NPC206007
0.6284	Remote Similarity	NPC53953
0.6282	Remote Similarity	NPC216810
0.6277	Remote Similarity	NPC473004
0.6277	Remote Similarity	NPC233791
0.6275	Remote Similarity	NPC115859
0.6272	Remote Similarity	NPC214239
0.6271	Remote Similarity	NPC469505
0.6267	Remote Similarity	NPC476014
0.6267	Remote Similarity	NPC476031
0.6259	Remote Similarity	NPC105249
0.6258	Remote Similarity	NPC188377
0.6258	Remote Similarity	NPC473268
0.6258	Remote Similarity	NPC65735
0.6258	Remote Similarity	NPC42400
0.6258	Remote Similarity	NPC225745
0.6257	Remote Similarity	NPC208890
0.625	Remote Similarity	NPC469479
0.625	Remote Similarity	NPC471396
0.625	Remote Similarity	NPC473982
0.625	Remote Similarity	NPC153631
0.625	Remote Similarity	NPC137710
0.625	Remote Similarity	NPC473969
0.6242	Remote Similarity	NPC252004
0.6236	Remote Similarity	NPC471568
0.6236	Remote Similarity	NPC473196
0.6236	Remote Similarity	NPC473693
0.6235	Remote Similarity	NPC470088
0.623	Remote Similarity	NPC327005
0.623	Remote Similarity	NPC24228
0.6226	Remote Similarity	NPC45947
0.622	Remote Similarity	NPC472376
0.622	Remote Similarity	NPC177262
0.622	Remote Similarity	NPC231572
0.6216	Remote Similarity	NPC26157
0.6216	Remote Similarity	NPC1811
0.6216	Remote Similarity	NPC102760
0.6213	Remote Similarity	NPC233763
0.6211	Remote Similarity	NPC198401
0.6207	Remote Similarity	NPC219969
0.62	Remote Similarity	NPC11821
0.6196	Remote Similarity	NPC281104
0.6196	Remote Similarity	NPC146872
0.619	Remote Similarity	NPC117674
0.619	Remote Similarity	NPC229387
0.6188	Remote Similarity	NPC67978
0.6188	Remote Similarity	NPC303581
0.6182	Remote Similarity	NPC474615
0.618	Remote Similarity	NPC186617
0.618	Remote Similarity	NPC231198
0.6178	Remote Similarity	NPC308895
0.6176	Remote Similarity	NPC281398
0.6176	Remote Similarity	NPC224418
0.6173	Remote Similarity	NPC94280
0.6173	Remote Similarity	NPC328419
0.6173	Remote Similarity	NPC200718
0.6173	Remote Similarity	NPC103947
0.6173	Remote Similarity	NPC193673
0.6173	Remote Similarity	NPC45783
0.6173	Remote Similarity	NPC159150
0.6171	Remote Similarity	NPC93653
0.617	Remote Similarity	NPC473008
0.617	Remote Similarity	NPC283207
0.6169	Remote Similarity	NPC97566
0.6164	Remote Similarity	NPC59502
0.6159	Remote Similarity	NPC474987
0.6159	Remote Similarity	NPC316062
0.6159	Remote Similarity	NPC76844
0.6158	Remote Similarity	NPC254700
0.6154	Remote Similarity	NPC27798
0.6154	Remote Similarity	NPC93241
0.6154	Remote Similarity	NPC195920
0.6149	Remote Similarity	NPC54626
0.614	Remote Similarity	NPC469540
0.614	Remote Similarity	NPC469539
0.6139	Remote Similarity	NPC141059
0.6135	Remote Similarity	NPC96406
0.6129	Remote Similarity	NPC314329
0.6129	Remote Similarity	NPC473379
0.6129	Remote Similarity	NPC471549
0.6127	Remote Similarity	NPC320751
0.6121	Remote Similarity	NPC236532
0.6121	Remote Similarity	NPC160747
0.612	Remote Similarity	NPC475421
0.612	Remote Similarity	NPC308267
0.6118	Remote Similarity	NPC475864

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 NPC471647 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	737
0.2-0.3	1289
0.3-0.4	2215
0.4-0.5	3233
0.5-0.6	1349
0.6-0.7	150
0.7-0.8	5
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
0.7325	Intermediate Similarity	NPD160	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD743	Approved
0.7246	Intermediate Similarity	NPD5262	Discontinued
0.7171	Intermediate Similarity	NPD3142	Approved
0.7171	Intermediate Similarity	NPD3140	Approved
0.7117	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1670	Discontinued
0.6933	Remote Similarity	NPD3613	Discontinued
0.6928	Remote Similarity	NPD7317	Phase 3
0.6845	Remote Similarity	NPD7318	Phase 3
0.6839	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3446	Phase 1
0.674	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6279	Approved
0.6726	Remote Similarity	NPD6844	Discontinued
0.6726	Remote Similarity	NPD6280	Approved
0.6723	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6321	Discontinued
0.6667	Remote Similarity	NPD1309	Phase 2
0.6667	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1307	Phase 2
0.6648	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD824	Approved
0.6584	Remote Similarity	NPD3656	Approved
0.6577	Remote Similarity	NPD2594	Approved
0.6577	Remote Similarity	NPD2595	Approved
0.6576	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD2245	Discovery
0.6554	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4503	Phase 2
0.6509	Remote Similarity	NPD2592	Discontinued
0.6508	Remote Similarity	NPD7811	Phase 3
0.6508	Remote Similarity	NPD7810	Phase 3
0.6505	Remote Similarity	NPD4466	Phase 1
0.6503	Remote Similarity	NPD2654	Approved
0.6494	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD7626	Approved
0.6492	Remote Similarity	NPD7627	Approved
0.6486	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5890	Approved
0.6471	Remote Similarity	NPD5889	Approved
0.6453	Remote Similarity	NPD5977	Approved
0.6453	Remote Similarity	NPD5978	Approved
0.6447	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD2492	Phase 1
0.6437	Remote Similarity	NPD6862	Phase 2
0.6433	Remote Similarity	NPD6039	Approved
0.6433	Remote Similarity	NPD7577	Discontinued
0.6432	Remote Similarity	NPD5910	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD1880	Phase 3
0.642	Remote Similarity	NPD3156	Discontinued
0.642	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.642	Remote Similarity	NPD6808	Phase 2
0.6416	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD4661	Approved
0.6407	Remote Similarity	NPD4662	Approved
0.6407	Remote Similarity	NPD2335	Discontinued
0.6393	Remote Similarity	NPD6618	Phase 2
0.6387	Remote Similarity	NPD5457	Discontinued
0.6378	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1420	Approved
0.6364	Remote Similarity	NPD1421	Approved
0.6358	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD5967	Approved
0.6348	Remote Similarity	NPD2248	Approved
0.6348	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD2246	Approved
0.6347	Remote Similarity	NPD5297	Approved
0.6343	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.634	Remote Similarity	NPD4465	Phase 2
0.634	Remote Similarity	NPD4467	Phase 2
0.6333	Remote Similarity	NPD1212	Approved
0.6331	Remote Similarity	NPD3869	Phase 3
0.6331	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD3873	Phase 3
0.6331	Remote Similarity	NPD7131	Phase 3
0.6329	Remote Similarity	NPD5746	Approved
0.6328	Remote Similarity	NPD5186	Approved
0.6328	Remote Similarity	NPD5183	Approved
0.6322	Remote Similarity	NPD504	Phase 2
0.6319	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6585	Discontinued
0.6316	Remote Similarity	NPD5564	Approved
0.6307	Remote Similarity	NPD2904	Discontinued
0.6302	Remote Similarity	NPD4496	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7291	Discontinued
0.6286	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD2247	Approved
0.6271	Remote Similarity	NPD2249	Approved
0.627	Remote Similarity	NPD3154	Approved
0.627	Remote Similarity	NPD3153	Approved
0.6265	Remote Similarity	NPD6748	Discontinued
0.6264	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD4258	Approved
0.6257	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD4259	Approved
0.6257	Remote Similarity	NPD1986	Approved
0.6257	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6382	Discontinued
0.625	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5745	Approved
0.6243	Remote Similarity	NPD5313	Approved
0.6243	Remote Similarity	NPD5312	Approved
0.6242	Remote Similarity	NPD2990	Approved
0.6242	Remote Similarity	NPD2987	Approved
0.6237	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD1987	Approved
0.6237	Remote Similarity	NPD4515	Suspended
0.6237	Remote Similarity	NPD1985	Approved
0.6236	Remote Similarity	NPD4166	Phase 2
0.6229	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4130	Phase 3
0.622	Remote Similarity	NPD1725	Approved
0.6215	Remote Similarity	NPD3862	Approved
0.6215	Remote Similarity	NPD3861	Approved
0.6209	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD2388	Discontinued
0.6196	Remote Similarity	NPD2569	Approved
0.6196	Remote Similarity	NPD2567	Approved
0.6196	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.618	Remote Similarity	NPD2680	Approved
0.618	Remote Similarity	NPD2681	Approved
0.6178	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD4098	Discontinued
0.6171	Remote Similarity	NPD9478	Approved
0.6171	Remote Similarity	NPD9479	Approved
0.617	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD3447	Discontinued
0.6162	Remote Similarity	NPD1639	Discontinued
0.6159	Remote Similarity	NPD6380	Phase 1
0.6159	Remote Similarity	NPD2164	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD3958	Approved
0.6154	Remote Similarity	NPD6020	Phase 2
0.615	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5515	Phase 2
0.6142	Remote Similarity	NPD8161	Suspended
0.6139	Remote Similarity	NPD5293	Phase 2
0.6138	Remote Similarity	NPD5624	Phase 3
0.6138	Remote Similarity	NPD5626	Phase 3
0.6138	Remote Similarity	NPD5625	Phase 3
0.6134	Remote Similarity	NPD8164	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD5228	Phase 3
0.6133	Remote Similarity	NPD3366	Approved
0.6129	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD1142	Approved
0.6127	Remote Similarity	NPD1143	Approved
0.6127	Remote Similarity	NPD1141	Approved
0.6127	Remote Similarity	NPD1140	Approved
0.6126	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.612	Remote Similarity	NPD3885	Approved
0.6117	Remote Similarity	NPD7693	Approved
0.6111	Remote Similarity	NPD7043	Discontinued
0.6108	Remote Similarity	NPD44	Approved
0.6108	Remote Similarity	NPD6364	Approved
0.6092	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD6385	Approved
0.6092	Remote Similarity	NPD6386	Approved
0.6089	Remote Similarity	NPD7126	Discontinued
0.6084	Remote Similarity	NPD2344	Approved
0.6082	Remote Similarity	NPD2186	Approved
0.6081	Remote Similarity	NPD2671	Approved
0.6081	Remote Similarity	NPD2673	Approved
0.6078	Remote Similarity	NPD2486	Discontinued
0.6077	Remote Similarity	NPD246	Approved
0.6077	Remote Similarity	NPD6894	Phase 1
0.6075	Remote Similarity	NPD7281	Phase 3
0.6075	Remote Similarity	NPD7280	Phase 3
0.6074	Remote Similarity	NPD4622	Approved
0.6074	Remote Similarity	NPD4618	Approved
0.6073	Remote Similarity	NPD6181	Discontinued
0.6071	Remote Similarity	NPD5481	Discontinued
0.6069	Remote Similarity	NPD2649	Approved
0.6069	Remote Similarity	NPD2651	Approved
0.6066	Remote Similarity	NPD4981	Phase 2
0.6065	Remote Similarity	NPD3294	Phase 2
0.6064	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD822	Approved
0.6057	Remote Similarity	NPD7248	Discontinued
0.6051	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD7713	Phase 3
0.6049	Remote Similarity	NPD4475	Approved
0.6049	Remote Similarity	NPD4474	Approved
0.6047	Remote Similarity	NPD3639	Approved
0.6047	Remote Similarity	NPD3641	Approved
0.6047	Remote Similarity	NPD3640	Phase 3

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