NPASS Compound

Structure

NPC471648 OpenBabel07101719132D 29 31 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 -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 7.1449 -1.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 -1.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 -0.2976 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 -1.2976 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 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 -3.8457 -2.2655 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 5.4128 -0.2976 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 4 2 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 20 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 20 2 0 0 0 0 10 21 1 0 0 0 0 11 23 2 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 27 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 22 1 0 0 0 0 18 24 2 0 0 0 0 19 22 2 0 0 0 0 19 29 1 0 0 0 0 22 25 1 0 0 0 0 23 26 1 0 0 0 0 24 29 1 0 0 0 0 25 27 1 0 0 0 0 25 28 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.23
Volume:	431.133
LogP:	5.075
LogD:	4.357
LogS:	-5.336
# Rotatable Bonds:	8
TPSA:	36.69
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.581
Synthetic Accessibility Score:	2.82
Fsp3:	0.32
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:	-4.756
MDCK Permeability:	2.0579760530381463e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.053

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147
Plasma Protein Binding (PPB):	98.2234878540039%
Volume Distribution (VD):	1.415
Pgp-substrate:	1.3086397647857666%

ADMET: Metabolism

CYP1A2-inhibitor:	0.474
CYP1A2-substrate:	0.304
CYP2C19-inhibitor:	0.915
CYP2C19-substrate:	0.338
CYP2C9-inhibitor:	0.798
CYP2C9-substrate:	0.792
CYP2D6-inhibitor:	0.181
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.666
CYP3A4-substrate:	0.465

ADMET: Excretion

Clearance (CL):	3.783
Half-life (T1/2):	0.497

ADMET: Toxicity

hERG Blockers:	0.889
Human Hepatotoxicity (H-HT):	0.934
Drug-inuced Liver Injury (DILI):	0.583
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.988
Maximum Recommended Daily Dose:	0.585
Skin Sensitization:	0.336
Carcinogencity:	0.369
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.651

Download Data

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

Natural Product: NPC471648

Natural Product ID:	NPC471648
*Common Name:**	(5-((1E,5Z)-2,6-Dimethylocta-1,5,7-Trienyl)Furan-3-Yl)(4-Phenylpiperazin-1-Yl)Methanone
IUPAC Name:	[5-[(1E,5Z)-2,6-dimethylocta-1,5,7-trienyl]furan-3-yl]-(4-phenylpiperazin-1-yl)methanone
Synonyms:
Standard InCHIKey:	JOZSYXLMLHPMNC-NXKVSJAESA-N
Standard InCHI:	InChI=1S/C25H30N2O2/c1-4-20(2)9-8-10-21(3)17-24-18-22(19-29-24)25(28)27-15-13-26(14-16-27)23-11-6-5-7-12-23/h4-7,9,11-12,17-19H,1,8,10,13-16H2,2-3H3/b20-9-,21-17+
SMILES:	CC(=CC1=CC(=CO1)C(=O)N2CCN(CC2)C3=CC=CC=C3)CCC=C(C)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3087064
PubChem CID:	72543911
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002389] Diazinanes [CHEMONTID:0000189] Piperazines [CHEMONTID:0001984] Phenylpiperazines

*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	=	28600.0	nM	PMID[473032]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	39800.0	nM	PMID[473032]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	32100.0	nM	PMID[473032]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	28300.0	nM	PMID[473032]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	30300.0	nM	PMID[473032]

☑ 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 NPC471648 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	321
0.1-0.2	3626
0.2-0.3	12775
0.3-0.4	3854
0.4-0.5	14951
0.5-0.6	6904
0.6-0.7	253
0.7-0.8	7
0.8-0.85	0
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8981	High Similarity	NPC471649
0.8831	High Similarity	NPC471646
0.8831	High Similarity	NPC471647
0.8827	High Similarity	NPC471652
0.8659	High Similarity	NPC471651
0.84	Intermediate Similarity	NPC45389
0.8251	Intermediate Similarity	NPC41216
0.788	Intermediate Similarity	NPC112937
0.7833	Intermediate Similarity	NPC471650
0.72	Intermediate Similarity	NPC93653
0.7174	Intermediate Similarity	NPC314659
0.7158	Intermediate Similarity	NPC198401
0.7143	Intermediate Similarity	NPC473004
0.712	Intermediate Similarity	NPC197335
0.7059	Intermediate Similarity	NPC87391
0.7048	Intermediate Similarity	NPC208170
0.7048	Intermediate Similarity	NPC216149
0.7045	Intermediate Similarity	NPC301163
0.7012	Intermediate Similarity	NPC266425
0.7005	Intermediate Similarity	NPC268077
0.7	Intermediate Similarity	NPC269367
0.6983	Remote Similarity	NPC299582
0.6959	Remote Similarity	NPC286692
0.6954	Remote Similarity	NPC207971
0.6935	Remote Similarity	NPC198160
0.6915	Remote Similarity	NPC473007
0.6879	Remote Similarity	NPC223873
0.6872	Remote Similarity	NPC100863
0.6872	Remote Similarity	NPC234933
0.6872	Remote Similarity	NPC71124
0.6863	Remote Similarity	NPC16066
0.681	Remote Similarity	NPC122886
0.6804	Remote Similarity	NPC230313
0.6791	Remote Similarity	NPC5167
0.6791	Remote Similarity	NPC85613
0.679	Remote Similarity	NPC250476
0.6771	Remote Similarity	NPC473008
0.6766	Remote Similarity	NPC478075
0.6765	Remote Similarity	NPC116178
0.6755	Remote Similarity	NPC288305
0.6753	Remote Similarity	NPC254957
0.6751	Remote Similarity	NPC5374
0.6736	Remote Similarity	NPC1820
0.6732	Remote Similarity	NPC321166
0.6732	Remote Similarity	NPC217903
0.6731	Remote Similarity	NPC298436
0.6727	Remote Similarity	NPC231382
0.6725	Remote Similarity	NPC473444
0.6725	Remote Similarity	NPC26589
0.6718	Remote Similarity	NPC243626
0.6716	Remote Similarity	NPC477161
0.6703	Remote Similarity	NPC73280
0.6702	Remote Similarity	NPC116007
0.6686	Remote Similarity	NPC242000
0.6686	Remote Similarity	NPC308197
0.6684	Remote Similarity	NPC174629
0.6667	Remote Similarity	NPC270301
0.665	Remote Similarity	NPC15987
0.6648	Remote Similarity	NPC315257
0.6633	Remote Similarity	NPC138830
0.6618	Remote Similarity	NPC50562
0.6615	Remote Similarity	NPC206109
0.6615	Remote Similarity	NPC262725
0.6615	Remote Similarity	NPC114039
0.6603	Remote Similarity	NPC131885
0.6593	Remote Similarity	NPC199737
0.6587	Remote Similarity	NPC67658
0.6583	Remote Similarity	NPC241263
0.6582	Remote Similarity	NPC471825
0.6575	Remote Similarity	NPC133817
0.6575	Remote Similarity	NPC476443
0.6573	Remote Similarity	NPC97746
0.6562	Remote Similarity	NPC244862
0.6562	Remote Similarity	NPC67345
0.6557	Remote Similarity	NPC204867
0.655	Remote Similarity	NPC67904
0.6528	Remote Similarity	NPC83511
0.6522	Remote Similarity	NPC10732
0.6513	Remote Similarity	NPC473569
0.6512	Remote Similarity	NPC204156
0.6509	Remote Similarity	NPC329830
0.6495	Remote Similarity	NPC21425
0.6493	Remote Similarity	NPC168209
0.6491	Remote Similarity	NPC307682
0.649	Remote Similarity	NPC473006
0.6488	Remote Similarity	NPC330683
0.6488	Remote Similarity	NPC329567
0.6485	Remote Similarity	NPC473005
0.6477	Remote Similarity	NPC189908
0.6476	Remote Similarity	NPC313327
0.6465	Remote Similarity	NPC476436
0.6462	Remote Similarity	NPC323969
0.6461	Remote Similarity	NPC144691
0.6449	Remote Similarity	NPC205372
0.644	Remote Similarity	NPC222524
0.644	Remote Similarity	NPC70092
0.644	Remote Similarity	NPC283810
0.6439	Remote Similarity	NPC308943
0.6432	Remote Similarity	NPC308895
0.6432	Remote Similarity	NPC477258
0.6422	Remote Similarity	NPC14339
0.6413	Remote Similarity	NPC257763
0.6402	Remote Similarity	NPC473245
0.6402	Remote Similarity	NPC176304
0.6402	Remote Similarity	NPC175150
0.6402	Remote Similarity	NPC70840
0.6402	Remote Similarity	NPC470548
0.6402	Remote Similarity	NPC243633
0.6385	Remote Similarity	NPC128115
0.6383	Remote Similarity	NPC112336
0.6383	Remote Similarity	NPC474814
0.6381	Remote Similarity	NPC55470
0.6378	Remote Similarity	NPC477259
0.6378	Remote Similarity	NPC169387
0.6377	Remote Similarity	NPC477160
0.6374	Remote Similarity	NPC29285
0.6373	Remote Similarity	NPC27887
0.6368	Remote Similarity	NPC477590
0.6368	Remote Similarity	NPC477585
0.6368	Remote Similarity	NPC477588
0.6368	Remote Similarity	NPC477586
0.6364	Remote Similarity	NPC264176
0.6364	Remote Similarity	NPC204970
0.6359	Remote Similarity	NPC140296
0.6359	Remote Similarity	NPC257851
0.6354	Remote Similarity	NPC119669
0.6349	Remote Similarity	NPC96901
0.6347	Remote Similarity	NPC218323
0.6347	Remote Similarity	NPC217176
0.6343	Remote Similarity	NPC476462
0.6341	Remote Similarity	NPC270807
0.6341	Remote Similarity	NPC174915
0.6333	Remote Similarity	NPC30749
0.6333	Remote Similarity	NPC314223
0.6329	Remote Similarity	NPC100573
0.6329	Remote Similarity	NPC207873
0.6324	Remote Similarity	NPC288759
0.6322	Remote Similarity	NPC471653
0.6318	Remote Similarity	NPC476429
0.6316	Remote Similarity	NPC220241
0.6316	Remote Similarity	NPC295479
0.6308	Remote Similarity	NPC322621
0.6302	Remote Similarity	NPC472474
0.6302	Remote Similarity	NPC476236
0.6302	Remote Similarity	NPC469964
0.6292	Remote Similarity	NPC9373
0.6291	Remote Similarity	NPC87560
0.6291	Remote Similarity	NPC77777
0.6291	Remote Similarity	NPC195120
0.6286	Remote Similarity	NPC472098
0.6286	Remote Similarity	NPC305542
0.6284	Remote Similarity	NPC157931
0.6284	Remote Similarity	NPC470708
0.6283	Remote Similarity	NPC75179
0.628	Remote Similarity	NPC212123
0.6279	Remote Similarity	NPC29650
0.6279	Remote Similarity	NPC173295
0.6278	Remote Similarity	NPC477589
0.6278	Remote Similarity	NPC477587
0.6271	Remote Similarity	NPC260601
0.6262	Remote Similarity	NPC313112
0.6262	Remote Similarity	NPC301292
0.6257	Remote Similarity	NPC296085
0.6257	Remote Similarity	NPC254700
0.6256	Remote Similarity	NPC66777
0.6256	Remote Similarity	NPC74562
0.6256	Remote Similarity	NPC316181
0.6256	Remote Similarity	NPC151781
0.6256	Remote Similarity	NPC268223
0.6256	Remote Similarity	NPC471762
0.625	Remote Similarity	NPC14325
0.625	Remote Similarity	NPC127082
0.625	Remote Similarity	NPC28848
0.6244	Remote Similarity	NPC295898
0.6243	Remote Similarity	NPC243756
0.6243	Remote Similarity	NPC138365
0.6237	Remote Similarity	NPC28368
0.6223	Remote Similarity	NPC279527
0.6223	Remote Similarity	NPC214960
0.6221	Remote Similarity	NPC132308
0.6218	Remote Similarity	NPC140688
0.6216	Remote Similarity	NPC329631
0.6215	Remote Similarity	NPC168750
0.6211	Remote Similarity	NPC188400
0.6211	Remote Similarity	NPC205523
0.6209	Remote Similarity	NPC159815
0.6205	Remote Similarity	NPC99723
0.6202	Remote Similarity	NPC16249
0.6193	Remote Similarity	NPC471164
0.6193	Remote Similarity	NPC150308
0.6188	Remote Similarity	NPC160113
0.6188	Remote Similarity	NPC476220
0.6186	Remote Similarity	NPC298320
0.6183	Remote Similarity	NPC320064
0.6183	Remote Similarity	NPC27904
0.6181	Remote Similarity	NPC474059
0.6181	Remote Similarity	NPC208890
0.6176	Remote Similarity	NPC283079
0.6175	Remote Similarity	NPC148124
0.6173	Remote Similarity	NPC76433

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 NPC471648 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	718
0.2-0.3	1058
0.3-0.4	1149
0.4-0.5	3463
0.5-0.6	2210
0.6-0.7	326
0.7-0.8	15
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
0.7874	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6654	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6321	Discontinued
0.7473	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1880	Phase 3
0.7351	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5183	Approved
0.7345	Intermediate Similarity	NPD5186	Approved
0.7253	Intermediate Similarity	NPD6293	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD4496	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD1212	Approved
0.7204	Intermediate Similarity	NPD4515	Suspended
0.7179	Intermediate Similarity	NPD4465	Phase 2
0.7179	Intermediate Similarity	NPD4467	Phase 2
0.7165	Intermediate Similarity	NPD7627	Approved
0.7165	Intermediate Similarity	NPD7626	Approved
0.7143	Intermediate Similarity	NPD5294	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5515	Phase 2
0.705	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5293	Phase 2
0.7029	Intermediate Similarity	NPD4201	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7043	Discontinued
0.7	Intermediate Similarity	NPD7126	Discontinued
0.7	Intermediate Similarity	NPD5262	Discontinued
0.6959	Remote Similarity	NPD5071	Phase 2
0.6959	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD822	Approved
0.6939	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4981	Phase 2
0.6902	Remote Similarity	NPD4020	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2248	Approved
0.6885	Remote Similarity	NPD2246	Approved
0.6868	Remote Similarity	NPD5847	Phase 1
0.6865	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6874	Approved
0.6828	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6357	Discontinued
0.6813	Remote Similarity	NPD6457	Approved
0.6813	Remote Similarity	NPD2249	Approved
0.6813	Remote Similarity	NPD2247	Approved
0.6807	Remote Similarity	NPD3142	Approved
0.6807	Remote Similarity	NPD3140	Approved
0.6806	Remote Similarity	NPD2542	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD5997	Discontinued
0.6789	Remote Similarity	NPD3154	Approved
0.6789	Remote Similarity	NPD3153	Approved
0.6786	Remote Similarity	NPD743	Approved
0.6784	Remote Similarity	NPD5513	Phase 2
0.678	Remote Similarity	NPD4679	Discontinued
0.678	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4259	Approved
0.6771	Remote Similarity	NPD4258	Approved
0.6769	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4539	Phase 1
0.6733	Remote Similarity	NPD7467	Discontinued
0.6733	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD2681	Approved
0.6721	Remote Similarity	NPD2680	Approved
0.672	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7317	Phase 3
0.6703	Remote Similarity	NPD5858	Discontinued
0.6698	Remote Similarity	NPD7186	Phase 3
0.6684	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3793	Phase 3
0.6682	Remote Similarity	NPD3912	Discontinued
0.6651	Remote Similarity	NPD3441	Approved
0.6651	Remote Similarity	NPD3442	Approved
0.6648	Remote Similarity	NPD4205	Phase 3
0.6648	Remote Similarity	NPD2366	Approved
0.6633	Remote Similarity	NPD6519	Phase 2
0.6633	Remote Similarity	NPD5228	Phase 3
0.6632	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.663	Remote Similarity	NPD1012	Discontinued
0.663	Remote Similarity	NPD7318	Phase 3
0.6628	Remote Similarity	NPD4598	Approved
0.6628	Remote Similarity	NPD4597	Approved
0.6619	Remote Similarity	NPD3437	Discontinued
0.6615	Remote Similarity	NPD4372	Phase 1
0.661	Remote Similarity	NPD1670	Discontinued
0.6605	Remote Similarity	NPD1659	Phase 1
0.6599	Remote Similarity	NPD3964	Approved
0.6598	Remote Similarity	NPD6136	Phase 2
0.6589	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5860	Discontinued
0.6578	Remote Similarity	NPD5938	Phase 3
0.6575	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD1678	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD2791	Discontinued
0.6566	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD2425	Phase 1
0.6557	Remote Similarity	NPD1309	Phase 2
0.6557	Remote Similarity	NPD1307	Phase 2
0.655	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD7031	Phase 1
0.6543	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.654	Remote Similarity	NPD8479	Phase 2
0.6537	Remote Similarity	NPD3874	Discontinued
0.6526	Remote Similarity	NPD5566	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7225	Discontinued
0.6519	Remote Similarity	NPD6279	Approved
0.6519	Remote Similarity	NPD6844	Discontinued
0.6519	Remote Similarity	NPD6280	Approved
0.6513	Remote Similarity	NPD5113	Approved
0.6513	Remote Similarity	NPD5114	Approved
0.6513	Remote Similarity	NPD5112	Approved
0.6512	Remote Similarity	NPD3391	Approved
0.6508	Remote Similarity	NPD3965	Phase 1
0.6508	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD5025	Approved
0.6502	Remote Similarity	NPD6250	Discontinued
0.6497	Remote Similarity	NPD2335	Discontinued
0.6495	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD2670	Approved
0.6488	Remote Similarity	NPD2907	Approved
0.6488	Remote Similarity	NPD8027	Approved
0.6488	Remote Similarity	NPD2906	Approved
0.6485	Remote Similarity	NPD7316	Discontinued
0.6485	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5994	Discontinued
0.6474	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7753	Approved
0.6474	Remote Similarity	NPD7752	Approved
0.6471	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3507	Phase 2
0.6471	Remote Similarity	NPD4130	Phase 3
0.6471	Remote Similarity	NPD5601	Phase 2
0.6465	Remote Similarity	NPD5640	Discontinued
0.6462	Remote Similarity	NPD7180	Phase 3
0.6459	Remote Similarity	NPD7559	Phase 2
0.6458	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD2241	Approved
0.6453	Remote Similarity	NPD3170	Approved
0.6453	Remote Similarity	NPD3802	Phase 3
0.6448	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD850	Approved
0.6446	Remote Similarity	NPD848	Approved
0.6446	Remote Similarity	NPD849	Approved
0.6441	Remote Similarity	NPD7560	Approved
0.6429	Remote Similarity	NPD1769	Discontinued
0.6429	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD3613	Discontinued
0.6425	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD3627	Approved
0.6425	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6644	Discontinued
0.6421	Remote Similarity	NPD5600	Discontinued
0.6418	Remote Similarity	NPD7810	Phase 3
0.6418	Remote Similarity	NPD2778	Approved
0.6418	Remote Similarity	NPD7811	Phase 3
0.6411	Remote Similarity	NPD3945	Discontinued
0.641	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4082	Approved
0.6406	Remote Similarity	NPD4204	Approved
0.6406	Remote Similarity	NPD4203	Approved
0.6402	Remote Similarity	NPD3446	Phase 1
0.6402	Remote Similarity	NPD2359	Approved
0.6402	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4430	Phase 2
0.6398	Remote Similarity	NPD6719	Approved
0.6398	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD3239	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD4952	Phase 3
0.6376	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD1544	Phase 1
0.6368	Remote Similarity	NPD2361	Approved
0.6364	Remote Similarity	NPD3511	Discontinued
0.6364	Remote Similarity	NPD6379	Discontinued
0.6364	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3479	Discontinued
0.6359	Remote Similarity	NPD5514	Discontinued
0.6359	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD6063	Approved
0.6358	Remote Similarity	NPD2594	Approved
0.6358	Remote Similarity	NPD2595	Approved
0.6355	Remote Similarity	NPD5041	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6238	Discontinued
0.6354	Remote Similarity	NPD789	Phase 2
0.6351	Remote Similarity	NPD4846	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data