NPASS Compound

Structure

NPC471652 OpenBabel07101719522D 25 26 0 0 0 0 0 0 0 0999 V2000 -5.4280 -2.9700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4389 -3.1791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6756 -0.7520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8402 -2.1610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6646 -0.5430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2579 -1.4565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0768 0.2661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 3.2024 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 3.6808 2.7024 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 -3.8457 -2.2655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0823 0.1615 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 3.6808 1.7024 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 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 16 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 2 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 17 2 0 0 0 0 10 12 2 0 0 0 0 10 17 1 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 19 1 0 0 0 0 14 21 2 0 0 0 0 15 19 2 0 0 0 0 15 25 1 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 21 25 1 0 0 0 0 22 23 1 0 0 0 0 22 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	335.19
Volume:	376.804
LogP:	5.681
LogD:	4.589
LogS:	-5.976
# Rotatable Bonds:	8
TPSA:	42.24
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.616
Synthetic Accessibility Score:	2.784
Fsp3:	0.227
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.796
MDCK Permeability:	2.3236942070070654e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	99.75142669677734%
Volume Distribution (VD):	3.179
Pgp-substrate:	1.1327532529830933%

ADMET: Metabolism

CYP1A2-inhibitor:	0.733
CYP1A2-substrate:	0.907
CYP2C19-inhibitor:	0.886
CYP2C19-substrate:	0.204
CYP2C9-inhibitor:	0.872
CYP2C9-substrate:	0.44
CYP2D6-inhibitor:	0.567
CYP2D6-substrate:	0.879
CYP3A4-inhibitor:	0.779
CYP3A4-substrate:	0.375

ADMET: Excretion

Clearance (CL):	5.251
Half-life (T1/2):	0.286

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.747
Drug-inuced Liver Injury (DILI):	0.656
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.932
Maximum Recommended Daily Dose:	0.785
Skin Sensitization:	0.323
Carcinogencity:	0.598
Eye Corrosion:	0.004
Eye Irritation:	0.291
Respiratory Toxicity:	0.717

Download Data

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

Natural Product: NPC471652

Natural Product ID:	NPC471652
*Common Name:**	5-((1E,5Z)-2,6-Dimethylocta-1,5,7-Trienyl)-N-P-Tolylfuran-3-Carboxamide
IUPAC Name:	5-[(1E,5Z)-2,6-dimethylocta-1,5,7-trienyl]-N-(4-methylphenyl)furan-3-carboxamide
Synonyms:
Standard InCHIKey:	PQKLRSIVXPRHSL-PFVIGBDXSA-N
Standard InCHI:	InChI=1S/C22H25NO2/c1-5-16(2)7-6-8-18(4)13-21-14-19(15-25-21)22(24)23-20-11-9-17(3)10-12-20/h5,7,9-15H,1,6,8H2,2-4H3,(H,23,24)/b16-7-,18-13+
SMILES:	CC1=CC=C(C=C1)NC(=O)C2=COC(=C2)C=C(C)CCC=C(C)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3087068
PubChem CID:	72544148
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000285] Anilides [CHEMONTID:0004712] Aromatic anilides [CHEMONTID:0004755] Furanilides [CHEMONTID:0004757] 3-furanilides

*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	=	60400.0	nM	PMID[469910]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	65300.0	nM	PMID[469910]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	59500.0	nM	PMID[469910]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	63200.0	nM	PMID[469910]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	56500.0	nM	PMID[469910]

☑ 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 NPC471652 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	308
0.1-0.2	3815
0.2-0.3	12108
0.3-0.4	3952
0.4-0.5	14735
0.5-0.6	7517
0.6-0.7	249
0.7-0.8	11
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8827	High Similarity	NPC471648
0.8098	Intermediate Similarity	NPC471649
0.8023	Intermediate Similarity	NPC45389
0.7826	Intermediate Similarity	NPC471647
0.7826	Intermediate Similarity	NPC471646
0.7824	Intermediate Similarity	NPC471651
0.7796	Intermediate Similarity	NPC41216
0.7527	Intermediate Similarity	NPC112937
0.7289	Intermediate Similarity	NPC286692
0.7288	Intermediate Similarity	NPC73280
0.7126	Intermediate Similarity	NPC93653
0.7104	Intermediate Similarity	NPC314659
0.7097	Intermediate Similarity	NPC471650
0.7049	Intermediate Similarity	NPC197335
0.702	Intermediate Similarity	NPC269367
0.6995	Remote Similarity	NPC283810
0.6989	Remote Similarity	NPC257763
0.6989	Remote Similarity	NPC87391
0.6943	Remote Similarity	NPC241263
0.6919	Remote Similarity	NPC314223
0.691	Remote Similarity	NPC299582
0.6881	Remote Similarity	NPC16066
0.6875	Remote Similarity	NPC301163
0.6823	Remote Similarity	NPC243626
0.6823	Remote Similarity	NPC230313
0.6818	Remote Similarity	NPC477161
0.6788	Remote Similarity	NPC173295
0.6784	Remote Similarity	NPC478075
0.6768	Remote Similarity	NPC301292
0.6768	Remote Similarity	NPC313112
0.6763	Remote Similarity	NPC198503
0.6748	Remote Similarity	NPC298436
0.6727	Remote Similarity	NPC266425
0.672	Remote Similarity	NPC85613
0.672	Remote Similarity	NPC5167
0.6718	Remote Similarity	NPC100863
0.6701	Remote Similarity	NPC308895
0.67	Remote Similarity	NPC198160
0.6688	Remote Similarity	NPC67345
0.6688	Remote Similarity	NPC244862
0.6684	Remote Similarity	NPC288305
0.6684	Remote Similarity	NPC472163
0.6667	Remote Similarity	NPC473007
0.6667	Remote Similarity	NPC288759
0.6667	Remote Similarity	NPC208170
0.6667	Remote Similarity	NPC216149
0.6667	Remote Similarity	NPC49184
0.6649	Remote Similarity	NPC198401
0.6633	Remote Similarity	NPC234933
0.6632	Remote Similarity	NPC473004
0.6626	Remote Similarity	NPC122235
0.6618	Remote Similarity	NPC308137
0.6618	Remote Similarity	NPC310211
0.6618	Remote Similarity	NPC131885
0.6617	Remote Similarity	NPC222561
0.6605	Remote Similarity	NPC250476
0.6601	Remote Similarity	NPC25961
0.66	Remote Similarity	NPC268077
0.6596	Remote Similarity	NPC28368
0.6588	Remote Similarity	NPC97746
0.658	Remote Similarity	NPC1820
0.6575	Remote Similarity	NPC292143
0.6575	Remote Similarity	NPC139506
0.6567	Remote Similarity	NPC45190
0.6555	Remote Similarity	NPC150239
0.6553	Remote Similarity	NPC50562
0.655	Remote Similarity	NPC207971
0.6545	Remote Similarity	NPC231382
0.6538	Remote Similarity	NPC46561
0.6537	Remote Similarity	NPC116178
0.6535	Remote Similarity	NPC249583
0.6529	Remote Similarity	NPC242933
0.6528	Remote Similarity	NPC473008
0.6527	Remote Similarity	NPC132308
0.6522	Remote Similarity	NPC67658
0.6522	Remote Similarity	NPC254698
0.6514	Remote Similarity	NPC242000
0.6514	Remote Similarity	NPC223873
0.6512	Remote Similarity	NPC308197
0.6509	Remote Similarity	NPC122886
0.6505	Remote Similarity	NPC217903
0.6505	Remote Similarity	NPC321166
0.6494	Remote Similarity	NPC146370
0.6481	Remote Similarity	NPC226794
0.6471	Remote Similarity	NPC319645
0.6465	Remote Similarity	NPC71124
0.6462	Remote Similarity	NPC205372
0.646	Remote Similarity	NPC174915
0.646	Remote Similarity	NPC270807
0.6459	Remote Similarity	NPC247803
0.6458	Remote Similarity	NPC262725
0.6455	Remote Similarity	NPC70092
0.645	Remote Similarity	NPC196708
0.6447	Remote Similarity	NPC140688
0.6443	Remote Similarity	NPC474059
0.6433	Remote Similarity	NPC205523
0.6433	Remote Similarity	NPC204156
0.6432	Remote Similarity	NPC473196
0.6432	Remote Similarity	NPC471778
0.6429	Remote Similarity	NPC199737
0.6429	Remote Similarity	NPC471825
0.6429	Remote Similarity	NPC254957
0.6429	Remote Similarity	NPC168209
0.6421	Remote Similarity	NPC270301
0.6418	Remote Similarity	NPC15987
0.6412	Remote Similarity	NPC106606
0.6408	Remote Similarity	NPC187501
0.6407	Remote Similarity	NPC477645
0.6394	Remote Similarity	NPC298449
0.6394	Remote Similarity	NPC176113
0.6392	Remote Similarity	NPC45536
0.639	Remote Similarity	NPC477160
0.6384	Remote Similarity	NPC144691
0.6378	Remote Similarity	NPC114039
0.6378	Remote Similarity	NPC206109
0.6374	Remote Similarity	NPC476475
0.6372	Remote Similarity	NPC140296
0.6364	Remote Similarity	NPC6786
0.6359	Remote Similarity	NPC217176
0.6359	Remote Similarity	NPC474366
0.6358	Remote Similarity	NPC473444
0.6358	Remote Similarity	NPC26589
0.6352	Remote Similarity	NPC217180
0.6352	Remote Similarity	NPC312525
0.635	Remote Similarity	NPC5374
0.6341	Remote Similarity	NPC100573
0.6341	Remote Similarity	NPC207873
0.6341	Remote Similarity	NPC90185
0.6338	Remote Similarity	NPC243633
0.6338	Remote Similarity	NPC251071
0.6338	Remote Similarity	NPC175150
0.6335	Remote Similarity	NPC179605
0.6335	Remote Similarity	NPC279385
0.6333	Remote Similarity	NPC169402
0.6331	Remote Similarity	NPC253476
0.633	Remote Similarity	NPC196718
0.6327	Remote Similarity	NPC22476
0.6324	Remote Similarity	NPC300156
0.6321	Remote Similarity	NPC128683
0.6321	Remote Similarity	NPC225279
0.6316	Remote Similarity	NPC116238
0.6316	Remote Similarity	NPC307682
0.6312	Remote Similarity	NPC187547
0.6312	Remote Similarity	NPC206007
0.6312	Remote Similarity	NPC21831
0.6304	Remote Similarity	NPC204867
0.6296	Remote Similarity	NPC103292
0.6293	Remote Similarity	NPC308943
0.6293	Remote Similarity	NPC4687
0.6291	Remote Similarity	NPC280799
0.6291	Remote Similarity	NPC329830
0.6289	Remote Similarity	NPC116007
0.6275	Remote Similarity	NPC14339
0.6274	Remote Similarity	NPC208084
0.6273	Remote Similarity	NPC137710
0.6265	Remote Similarity	NPC184391
0.6264	Remote Similarity	NPC472241
0.6256	Remote Similarity	NPC102593
0.625	Remote Similarity	NPC218303
0.6244	Remote Similarity	NPC473187
0.6244	Remote Similarity	NPC323969
0.6243	Remote Similarity	NPC160747
0.6238	Remote Similarity	NPC138830
0.6238	Remote Similarity	NPC55470
0.6237	Remote Similarity	NPC314861
0.6236	Remote Similarity	NPC300596
0.6236	Remote Similarity	NPC237649
0.6235	Remote Similarity	NPC169766
0.623	Remote Similarity	NPC133817
0.623	Remote Similarity	NPC476443
0.6228	Remote Similarity	NPC209389
0.6226	Remote Similarity	NPC77777
0.6223	Remote Similarity	NPC112336
0.6223	Remote Similarity	NPC474814
0.6222	Remote Similarity	NPC188400
0.6221	Remote Similarity	NPC316574
0.6215	Remote Similarity	NPC117674
0.6213	Remote Similarity	NPC136340
0.6207	Remote Similarity	NPC214368
0.6205	Remote Similarity	NPC150308
0.6203	Remote Similarity	NPC470971
0.6203	Remote Similarity	NPC53953
0.6203	Remote Similarity	NPC57051
0.6201	Remote Similarity	NPC281398
0.6196	Remote Similarity	NPC79557
0.619	Remote Similarity	NPC177261
0.6188	Remote Similarity	NPC316062
0.6185	Remote Similarity	NPC471316
0.6182	Remote Similarity	NPC118853
0.6182	Remote Similarity	NPC192533
0.618	Remote Similarity	NPC93241
0.618	Remote Similarity	NPC27798
0.6179	Remote Similarity	NPC313327
0.6172	Remote Similarity	NPC23294
0.6172	Remote Similarity	NPC87413
0.6171	Remote Similarity	NPC325857
0.6171	Remote Similarity	NPC301702
0.6168	Remote Similarity	NPC174760
0.6164	Remote Similarity	NPC292036
0.6164	Remote Similarity	NPC252004

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 NPC471652 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	773
0.2-0.3	1065
0.3-0.4	1337
0.4-0.5	3579
0.5-0.6	1895
0.6-0.7	250
0.7-0.8	11
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
0.75	Intermediate Similarity	NPD822	Approved
0.7326	Intermediate Similarity	NPD7880	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4467	Phase 2
0.7292	Intermediate Similarity	NPD4465	Phase 2
0.7273	Intermediate Similarity	NPD5183	Approved
0.7273	Intermediate Similarity	NPD5186	Approved
0.7256	Intermediate Similarity	NPD4597	Approved
0.7256	Intermediate Similarity	NPD4598	Approved
0.7191	Intermediate Similarity	NPD2246	Approved
0.7191	Intermediate Similarity	NPD2248	Approved
0.7188	Intermediate Similarity	NPD7626	Approved
0.7188	Intermediate Similarity	NPD7627	Approved
0.7111	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4981	Phase 2
0.7081	Intermediate Similarity	NPD3153	Approved
0.7081	Intermediate Similarity	NPD3154	Approved
0.705	Intermediate Similarity	NPD4679	Discontinued
0.7027	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD2681	Approved
0.7022	Intermediate Similarity	NPD2680	Approved
0.6995	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1212	Approved
0.6968	Remote Similarity	NPD4258	Approved
0.6968	Remote Similarity	NPD4259	Approved
0.6959	Remote Similarity	NPD6321	Discontinued
0.6943	Remote Similarity	NPD1880	Phase 3
0.6927	Remote Similarity	NPD2249	Approved
0.6927	Remote Similarity	NPD6457	Approved
0.6927	Remote Similarity	NPD2247	Approved
0.6923	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5293	Phase 2
0.6875	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3964	Approved
0.686	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4539	Phase 1
0.6857	Remote Similarity	NPD2366	Approved
0.6854	Remote Similarity	NPD955	Approved
0.6839	Remote Similarity	NPD5515	Phase 2
0.6825	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6719	Approved
0.6802	Remote Similarity	NPD7528	Approved
0.6789	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD3170	Approved
0.6757	Remote Similarity	NPD2425	Phase 1
0.6751	Remote Similarity	NPD7316	Discontinued
0.675	Remote Similarity	NPD5950	Discontinued
0.6744	Remote Similarity	NPD1802	Approved
0.6744	Remote Similarity	NPD1801	Approved
0.6717	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD3874	Discontinued
0.6707	Remote Similarity	NPD2670	Approved
0.6703	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1559	Discontinued
0.6685	Remote Similarity	NPD2359	Approved
0.6684	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2672	Discontinued
0.6667	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD2361	Approved
0.6649	Remote Similarity	NPD2542	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5719	Approved
0.6633	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5071	Phase 2
0.6633	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.663	Remote Similarity	NPD1168	Approved
0.6629	Remote Similarity	NPD3627	Approved
0.6613	Remote Similarity	NPD3793	Phase 3
0.6612	Remote Similarity	NPD5847	Phase 1
0.661	Remote Similarity	NPD3684	Discontinued
0.6607	Remote Similarity	NPD6636	Phase 3
0.6607	Remote Similarity	NPD743	Approved
0.6605	Remote Similarity	NPD552	Approved
0.6605	Remote Similarity	NPD553	Approved
0.6605	Remote Similarity	NPD9567	Approved
0.66	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD2778	Approved
0.6596	Remote Similarity	NPD5637	Discontinued
0.6585	Remote Similarity	NPD3945	Discontinued
0.6583	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD2836	Approved
0.657	Remote Similarity	NPD2241	Approved
0.6566	Remote Similarity	NPD6519	Phase 2
0.6566	Remote Similarity	NPD2339	Phase 3
0.6557	Remote Similarity	NPD5262	Discontinued
0.6554	Remote Similarity	NPD6357	Discontinued
0.6548	Remote Similarity	NPD4668	Phase 2
0.6541	Remote Similarity	NPD5997	Discontinued
0.6524	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD3965	Phase 1
0.6524	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4661	Approved
0.6514	Remote Similarity	NPD4662	Approved
0.6514	Remote Similarity	NPD4161	Discontinued
0.651	Remote Similarity	NPD4515	Suspended
0.6503	Remote Similarity	NPD710	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2779	Approved
0.6484	Remote Similarity	NPD923	Approved
0.6484	Remote Similarity	NPD1307	Phase 2
0.6484	Remote Similarity	NPD1309	Phase 2
0.648	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD1276	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD1891	Discontinued
0.6471	Remote Similarity	NPD1110	Approved
0.6471	Remote Similarity	NPD1109	Approved
0.6462	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5858	Discontinued
0.6448	Remote Similarity	NPD3252	Approved
0.6444	Remote Similarity	NPD7317	Phase 3
0.6442	Remote Similarity	NPD1960	Phase 2
0.6441	Remote Similarity	NPD3869	Phase 3
0.6441	Remote Similarity	NPD3873	Phase 3
0.6441	Remote Similarity	NPD1670	Discontinued
0.6436	Remote Similarity	NPD6250	Discontinued
0.6433	Remote Similarity	NPD3391	Approved
0.6432	Remote Similarity	NPD6874	Approved
0.6432	Remote Similarity	NPD1161	Approved
0.6429	Remote Similarity	NPD3142	Approved
0.6429	Remote Similarity	NPD3140	Approved
0.642	Remote Similarity	NPD4888	Discontinued
0.6417	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5410	Discontinued
0.6411	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5416	Discontinued
0.6408	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4130	Phase 3
0.6402	Remote Similarity	NPD7186	Phase 3
0.64	Remote Similarity	NPD160	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4496	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD1913	Phase 1
0.6398	Remote Similarity	NPD692	Approved
0.6398	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7853	Phase 2
0.6391	Remote Similarity	NPD9694	Discovery
0.6387	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5632	Approved
0.638	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD3511	Discontinued
0.6374	Remote Similarity	NPD1626	Approved
0.6374	Remote Similarity	NPD7318	Phase 3
0.6374	Remote Similarity	NPD1012	Discontinued
0.6373	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7043	Discontinued
0.6369	Remote Similarity	NPD3229	Phase 2
0.6369	Remote Similarity	NPD5086	Approved
0.6368	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD6136	Phase 2
0.6359	Remote Similarity	NPD5928	Phase 1
0.6354	Remote Similarity	NPD6279	Approved
0.6354	Remote Similarity	NPD1769	Discontinued
0.6354	Remote Similarity	NPD6280	Approved
0.6349	Remote Similarity	NPD4503	Phase 2
0.6349	Remote Similarity	NPD4072	Approved
0.6349	Remote Similarity	NPD1170	Approved
0.6349	Remote Similarity	NPD4071	Approved
0.6344	Remote Similarity	NPD1839	Phase 1
0.6341	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD4493	Discontinued
0.6327	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD3289	Phase 3
0.6318	Remote Similarity	NPD3290	Approved
0.6313	Remote Similarity	NPD4952	Phase 3
0.6305	Remote Similarity	NPD5513	Phase 2
0.6302	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD1544	Phase 1
0.6294	Remote Similarity	NPD2331	Discontinued
0.6294	Remote Similarity	NPD2791	Discontinued
0.6292	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.629	Remote Similarity	NPD2821	Approved
0.6284	Remote Similarity	NPD3441	Approved
0.6284	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD3442	Approved
0.6283	Remote Similarity	NPD5445	Approved
0.6281	Remote Similarity	NPD5411	Discontinued
0.628	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD3947	Discontinued
0.6264	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD1861	Discovery
0.6263	Remote Similarity	NPD4466	Phase 1
0.6262	Remote Similarity	NPD8311	Discontinued
0.6262	Remote Similarity	NPD4154	Approved
0.6262	Remote Similarity	NPD7467	Discontinued
0.6262	Remote Similarity	NPD4082	Approved
0.6262	Remote Similarity	NPD2514	Approved
0.6256	Remote Similarity	NPD3863	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