NPASS Compound

Structure

NPC471651 OpenBabel07101719522D 36 39 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 5.4128 -3.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0109 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 -2.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 -2.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0109 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 1.7024 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 4.5468 -1.7976 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 6.2788 1.2024 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 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 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 5.4128 -0.2976 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 25 1 0 0 0 0 3 26 1 0 0 0 0 4 25 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 25 2 0 0 0 0 13 26 1 0 0 0 0 14 27 2 0 0 0 0 15 27 1 0 0 0 0 16 28 2 0 0 0 0 17 28 1 0 0 0 0 18 20 1 0 0 0 0 18 33 1 0 0 0 0 19 21 1 0 0 0 0 19 33 1 0 0 0 0 20 34 1 0 0 0 0 21 34 1 0 0 0 0 22 26 2 0 0 0 0 22 30 1 0 0 0 0 23 29 1 0 0 0 0 23 30 2 0 0 0 0 24 29 2 0 0 0 0 24 36 1 0 0 0 0 27 31 1 0 0 0 0 28 31 1 0 0 0 0 29 32 1 0 0 0 0 30 36 1 0 0 0 0 31 33 1 0 0 0 0 32 34 1 0 0 0 0 32 35 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.28
Volume:	535.739
LogP:	6.066
LogD:	5.005
LogS:	-5.454
# Rotatable Bonds:	10
TPSA:	36.69
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.305
Synthetic Accessibility Score:	2.887
Fsp3:	0.281
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.981
MDCK Permeability:	1.1721651389962062e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.839
Plasma Protein Binding (PPB):	97.86772918701172%
Volume Distribution (VD):	3.482
Pgp-substrate:	0.6766892075538635%

ADMET: Metabolism

CYP1A2-inhibitor:	0.183
CYP1A2-substrate:	0.331
CYP2C19-inhibitor:	0.941
CYP2C19-substrate:	0.455
CYP2C9-inhibitor:	0.937
CYP2C9-substrate:	0.805
CYP2D6-inhibitor:	0.955
CYP2D6-substrate:	0.883
CYP3A4-inhibitor:	0.87
CYP3A4-substrate:	0.848

ADMET: Excretion

Clearance (CL):	4.657
Half-life (T1/2):	0.04

ADMET: Toxicity

hERG Blockers:	0.941
Human Hepatotoxicity (H-HT):	0.931
Drug-inuced Liver Injury (DILI):	0.115
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.925
Maximum Recommended Daily Dose:	0.878
Skin Sensitization:	0.037
Carcinogencity:	0.059
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.786

Download Data

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

Natural Product: NPC471651

Natural Product ID:	NPC471651
*Common Name:**	(4-Benzhydrylpiperazin-1-Yl)(5-((1E,5Z)-2,6-Dimethylocta-1,5,7-Trienyl)Furan-3-Yl)Methanone
IUPAC Name:	(4-benzhydrylpiperazin-1-yl)-[5-[(1E,5Z)-2,6-dimethylocta-1,5,7-trienyl]furan-3-yl]methanone
Synonyms:
Standard InCHIKey:	FUWYHTVPTYJCEV-HYIFSMJFSA-N
Standard InCHI:	InChI=1S/C32H36N2O2/c1-4-25(2)12-11-13-26(3)22-30-23-29(24-36-30)32(35)34-20-18-33(19-21-34)31(27-14-7-5-8-15-27)28-16-9-6-10-17-28/h4-10,12,14-17,22-24,31H,1,11,13,18-21H2,2-3H3/b25-12-,26-22+
SMILES:	C=C/C(=CCC/C(=C/c1occ(c1)C(=O)N1CCN(CC1)C(c1ccccc1)c1ccccc1)/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3087067
PubChem CID:	72543914
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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	=	17800.0	nM	PMID[454618]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	26700.0	nM	PMID[454618]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	28500.0	nM	PMID[454618]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	24600.0	nM	PMID[454618]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	16800.0	nM	PMID[454618]

☑ 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 NPC471651 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	301
0.1-0.2	1989
0.2-0.3	8563
0.3-0.4	8707
0.4-0.5	10065
0.5-0.6	12204
0.6-0.7	838
0.7-0.8	24
0.8-0.85	1
0.85-0.9	1
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC471649
0.8947	High Similarity	NPC471646
0.8947	High Similarity	NPC471647
0.8659	High Similarity	NPC471648
0.8229	Intermediate Similarity	NPC471650
0.7824	Intermediate Similarity	NPC471652
0.768	Intermediate Similarity	NPC45389
0.7673	Intermediate Similarity	NPC216149
0.7673	Intermediate Similarity	NPC208170
0.7566	Intermediate Similarity	NPC41216
0.7532	Intermediate Similarity	NPC266425
0.747	Intermediate Similarity	NPC223873
0.7394	Intermediate Similarity	NPC112937
0.7317	Intermediate Similarity	NPC473444
0.7317	Intermediate Similarity	NPC26589
0.7225	Intermediate Similarity	NPC476443
0.7225	Intermediate Similarity	NPC133817
0.7143	Intermediate Similarity	NPC222524
0.7111	Intermediate Similarity	NPC473245
0.7111	Intermediate Similarity	NPC70840
0.7111	Intermediate Similarity	NPC176304
0.7105	Intermediate Similarity	NPC477258
0.7065	Intermediate Similarity	NPC27887
0.7059	Intermediate Similarity	NPC169387
0.7059	Intermediate Similarity	NPC477259
0.6995	Remote Similarity	NPC476236
0.6995	Remote Similarity	NPC472474
0.6995	Remote Similarity	NPC469964
0.6952	Remote Similarity	NPC116007
0.6867	Remote Similarity	NPC307682
0.6845	Remote Similarity	NPC186957
0.6845	Remote Similarity	NPC289167
0.6845	Remote Similarity	NPC76433
0.6842	Remote Similarity	NPC189908
0.6842	Remote Similarity	NPC208890
0.6832	Remote Similarity	NPC218323
0.6828	Remote Similarity	NPC327005
0.6804	Remote Similarity	NPC24228
0.6802	Remote Similarity	NPC296085
0.6791	Remote Similarity	NPC99723
0.6778	Remote Similarity	NPC254700
0.6778	Remote Similarity	NPC471396
0.6772	Remote Similarity	NPC297647
0.6772	Remote Similarity	NPC83511
0.6754	Remote Similarity	NPC283207
0.6732	Remote Similarity	NPC38964
0.6726	Remote Similarity	NPC471316
0.672	Remote Similarity	NPC473007
0.6705	Remote Similarity	NPC27798
0.6705	Remote Similarity	NPC93241
0.6705	Remote Similarity	NPC71629
0.6705	Remote Similarity	NPC119669
0.6684	Remote Similarity	NPC473004
0.6667	Remote Similarity	NPC82056
0.6667	Remote Similarity	NPC308895
0.6667	Remote Similarity	NPC324081
0.6647	Remote Similarity	NPC9373
0.6647	Remote Similarity	NPC117674
0.6646	Remote Similarity	NPC244862
0.6646	Remote Similarity	NPC67345
0.6646	Remote Similarity	NPC283079
0.6632	Remote Similarity	NPC102760
0.6632	Remote Similarity	NPC315542
0.6632	Remote Similarity	NPC128683
0.6629	Remote Similarity	NPC281398
0.6625	Remote Similarity	NPC314329
0.6615	Remote Similarity	NPC198401
0.6614	Remote Similarity	NPC314659
0.6611	Remote Similarity	NPC93653
0.6593	Remote Similarity	NPC153631
0.6588	Remote Similarity	NPC471653
0.6587	Remote Similarity	NPC132308
0.658	Remote Similarity	NPC473008
0.6576	Remote Similarity	NPC473693
0.6576	Remote Similarity	NPC471568
0.6568	Remote Similarity	NPC281104
0.6568	Remote Similarity	NPC106606
0.6567	Remote Similarity	NPC268077
0.6561	Remote Similarity	NPC197335
0.6561	Remote Similarity	NPC45536
0.6556	Remote Similarity	NPC25084
0.6556	Remote Similarity	NPC247639
0.655	Remote Similarity	NPC473005
0.6543	Remote Similarity	NPC285394
0.6541	Remote Similarity	NPC284842
0.6541	Remote Similarity	NPC35744
0.6536	Remote Similarity	NPC470708
0.6529	Remote Similarity	NPC42400
0.6529	Remote Similarity	NPC220923
0.6524	Remote Similarity	NPC303581
0.6524	Remote Similarity	NPC67978
0.6522	Remote Similarity	NPC231198
0.6522	Remote Similarity	NPC26285
0.6522	Remote Similarity	NPC469505
0.6522	Remote Similarity	NPC186617
0.6519	Remote Similarity	NPC312525
0.6519	Remote Similarity	NPC217180
0.6517	Remote Similarity	NPC207971
0.6515	Remote Similarity	NPC46744
0.6515	Remote Similarity	NPC14622
0.6515	Remote Similarity	NPC70290
0.6515	Remote Similarity	NPC215098
0.6515	Remote Similarity	NPC73020
0.6515	Remote Similarity	NPC124302
0.6513	Remote Similarity	NPC473716
0.6513	Remote Similarity	NPC226708
0.6513	Remote Similarity	NPC475597
0.651	Remote Similarity	NPC87391
0.651	Remote Similarity	NPC276120
0.6509	Remote Similarity	NPC196708
0.6503	Remote Similarity	NPC469479
0.6502	Remote Similarity	NPC198160
0.65	Remote Similarity	NPC24232
0.65	Remote Similarity	NPC287757
0.65	Remote Similarity	NPC319320
0.6497	Remote Similarity	NPC205523
0.6488	Remote Similarity	NPC269367
0.6486	Remote Similarity	NPC75179
0.648	Remote Similarity	NPC144010
0.6477	Remote Similarity	NPC233763
0.6471	Remote Similarity	NPC164608
0.6471	Remote Similarity	NPC99078
0.6468	Remote Similarity	NPC328700
0.6468	Remote Similarity	NPC119818
0.6468	Remote Similarity	NPC2173
0.6468	Remote Similarity	NPC202771
0.6467	Remote Similarity	NPC257390
0.6459	Remote Similarity	NPC313327
0.6457	Remote Similarity	NPC469978
0.6455	Remote Similarity	NPC475421
0.6455	Remote Similarity	NPC308267
0.6453	Remote Similarity	NPC314682
0.645	Remote Similarity	NPC72788
0.645	Remote Similarity	NPC120671
0.645	Remote Similarity	NPC29650
0.645	Remote Similarity	NPC314100
0.645	Remote Similarity	NPC226652
0.6448	Remote Similarity	NPC135006
0.6444	Remote Similarity	NPC156244
0.6444	Remote Similarity	NPC145830
0.6438	Remote Similarity	NPC137710
0.6438	Remote Similarity	NPC54243
0.6433	Remote Similarity	NPC470707
0.6433	Remote Similarity	NPC252107
0.6432	Remote Similarity	NPC71124
0.6432	Remote Similarity	NPC234933
0.6432	Remote Similarity	NPC100863
0.6424	Remote Similarity	NPC184391
0.6422	Remote Similarity	NPC478075
0.642	Remote Similarity	NPC174915
0.642	Remote Similarity	NPC270807
0.6417	Remote Similarity	NPC86469
0.6416	Remote Similarity	NPC213206
0.6416	Remote Similarity	NPC328750
0.6416	Remote Similarity	NPC474915
0.6416	Remote Similarity	NPC188163
0.6413	Remote Similarity	NPC299582
0.6412	Remote Similarity	NPC196609
0.6412	Remote Similarity	NPC205178
0.6412	Remote Similarity	NPC251454
0.6412	Remote Similarity	NPC277042
0.6412	Remote Similarity	NPC136330
0.6412	Remote Similarity	NPC73883
0.6412	Remote Similarity	NPC230698
0.6412	Remote Similarity	NPC138365
0.6412	Remote Similarity	NPC255817
0.641	Remote Similarity	NPC166979
0.641	Remote Similarity	NPC174629
0.6409	Remote Similarity	NPC67654
0.6409	Remote Similarity	NPC471863
0.6405	Remote Similarity	NPC140688
0.6404	Remote Similarity	NPC198427
0.6404	Remote Similarity	NPC469540
0.6404	Remote Similarity	NPC469539
0.6402	Remote Similarity	NPC329992
0.64	Remote Similarity	NPC5374
0.6398	Remote Similarity	NPC474858
0.6398	Remote Similarity	NPC473196
0.6398	Remote Similarity	NPC246214
0.6393	Remote Similarity	NPC160015
0.6393	Remote Similarity	NPC247677
0.6391	Remote Similarity	NPC470740
0.6389	Remote Similarity	NPC472406
0.6389	Remote Similarity	NPC148423
0.6389	Remote Similarity	NPC135303
0.6387	Remote Similarity	NPC270301
0.6386	Remote Similarity	NPC298884
0.6384	Remote Similarity	NPC90844
0.6384	Remote Similarity	NPC253883
0.6384	Remote Similarity	NPC95075
0.6378	Remote Similarity	NPC473502
0.6378	Remote Similarity	NPC475393
0.6375	Remote Similarity	NPC206007
0.6375	Remote Similarity	NPC243704
0.6375	Remote Similarity	NPC32298
0.6374	Remote Similarity	NPC122365
0.6374	Remote Similarity	NPC301163
0.6374	Remote Similarity	NPC179170
0.6374	Remote Similarity	NPC88958
0.6369	Remote Similarity	NPC136340

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 NPC471651 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	653
0.2-0.3	961
0.3-0.4	1567
0.4-0.5	3096
0.5-0.6	2254
0.6-0.7	392
0.7-0.8	25
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
0.7514	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4078	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6321	Discontinued
0.7273	Intermediate Similarity	NPD5262	Discontinued
0.7263	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD160	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD6040	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6654	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3140	Approved
0.7205	Intermediate Similarity	NPD3142	Approved
0.7184	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7811	Phase 3
0.7173	Intermediate Similarity	NPD7810	Phase 3
0.7168	Intermediate Similarity	NPD6280	Approved
0.7168	Intermediate Similarity	NPD7317	Phase 3
0.7168	Intermediate Similarity	NPD6279	Approved
0.7168	Intermediate Similarity	NPD6844	Discontinued
0.7167	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6862	Phase 2
0.7158	Intermediate Similarity	NPD7190	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7318	Phase 3
0.7074	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD743	Approved
0.7069	Intermediate Similarity	NPD7577	Discontinued
0.7062	Intermediate Similarity	NPD7626	Approved
0.7062	Intermediate Similarity	NPD7627	Approved
0.7045	Intermediate Similarity	NPD4947	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6748	Discontinued
0.7021	Intermediate Similarity	NPD5910	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6039	Approved
0.7006	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1670	Discontinued
0.6968	Remote Similarity	NPD7291	Discontinued
0.6959	Remote Similarity	NPD8164	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8161	Suspended
0.6944	Remote Similarity	NPD5186	Approved
0.6944	Remote Similarity	NPD5183	Approved
0.6923	Remote Similarity	NPD3446	Phase 1
0.6914	Remote Similarity	NPD5889	Approved
0.6914	Remote Similarity	NPD5890	Approved
0.6911	Remote Similarity	NPD4466	Phase 1
0.6893	Remote Similarity	NPD5978	Approved
0.6893	Remote Similarity	NPD5967	Approved
0.6893	Remote Similarity	NPD5977	Approved
0.6879	Remote Similarity	NPD7131	Phase 3
0.6878	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5457	Discontinued
0.6872	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD6808	Phase 2
0.6848	Remote Similarity	NPD4503	Phase 2
0.6833	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7713	Phase 3
0.6825	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD1307	Phase 2
0.6816	Remote Similarity	NPD1309	Phase 2
0.6809	Remote Similarity	NPD6618	Phase 2
0.6805	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5564	Approved
0.6789	Remote Similarity	NPD7693	Approved
0.6782	Remote Similarity	NPD3873	Phase 3
0.6782	Remote Similarity	NPD3869	Phase 3
0.6774	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4661	Approved
0.6763	Remote Similarity	NPD4662	Approved
0.6761	Remote Similarity	NPD6585	Discontinued
0.6757	Remote Similarity	NPD5312	Approved
0.6757	Remote Similarity	NPD5313	Approved
0.6755	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD2594	Approved
0.6752	Remote Similarity	NPD2595	Approved
0.6742	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.674	Remote Similarity	NPD2904	Discontinued
0.6728	Remote Similarity	NPD7247	Discontinued
0.6727	Remote Similarity	NPD4475	Approved
0.6727	Remote Similarity	NPD4474	Approved
0.6708	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7793	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6894	Phase 1
0.6685	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7280	Phase 3
0.6667	Remote Similarity	NPD6364	Approved
0.6667	Remote Similarity	NPD5689	Approved
0.6667	Remote Similarity	NPD4166	Phase 2
0.6667	Remote Similarity	NPD7281	Phase 3
0.6667	Remote Similarity	NPD4098	Discontinued
0.6667	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD44	Approved
0.6667	Remote Similarity	NPD5688	Approved
0.6667	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2335	Discontinued
0.6667	Remote Similarity	NPD2592	Discontinued
0.6667	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.665	Remote Similarity	NPD1880	Phase 3
0.6649	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD3861	Approved
0.6648	Remote Similarity	NPD3862	Approved
0.6646	Remote Similarity	NPD6382	Discontinued
0.663	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2388	Discontinued
0.6629	Remote Similarity	NPD6385	Approved
0.6629	Remote Similarity	NPD6386	Approved
0.6628	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD2990	Approved
0.6626	Remote Similarity	NPD2987	Approved
0.6625	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7598	Phase 2
0.66	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD7043	Discontinued
0.6582	Remote Similarity	NPD6834	Approved
0.6578	Remote Similarity	NPD6020	Phase 2
0.6568	Remote Similarity	NPD2567	Approved
0.6568	Remote Similarity	NPD2569	Approved
0.6567	Remote Similarity	NPD4465	Phase 2
0.6567	Remote Similarity	NPD4467	Phase 2
0.6566	Remote Similarity	NPD6874	Approved
0.6564	Remote Similarity	NPD6181	Discontinued
0.6562	Remote Similarity	NPD4515	Suspended
0.6559	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.655	Remote Similarity	NPD3656	Approved
0.655	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2344	Approved
0.6548	Remote Similarity	NPD5515	Phase 2
0.6548	Remote Similarity	NPD4618	Approved
0.6548	Remote Similarity	NPD4622	Approved
0.6545	Remote Similarity	NPD6851	Approved
0.6545	Remote Similarity	NPD6853	Approved
0.6545	Remote Similarity	NPD4483	Discontinued
0.6543	Remote Similarity	NPD1421	Approved
0.6543	Remote Similarity	NPD5157	Phase 1
0.6543	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD1420	Approved
0.6543	Remote Similarity	NPD5159	Phase 2
0.6533	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6380	Phase 1
0.6527	Remote Similarity	NPD7477	Discontinued
0.6527	Remote Similarity	NPD2245	Discovery
0.6524	Remote Similarity	NPD7177	Discontinued
0.6522	Remote Similarity	NPD5293	Phase 2
0.6517	Remote Similarity	NPD824	Approved
0.6515	Remote Similarity	NPD4420	Approved
0.6512	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4981	Phase 2
0.6509	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD5746	Approved
0.65	Remote Similarity	NPD7248	Discontinued
0.6497	Remote Similarity	NPD3639	Approved
0.6497	Remote Similarity	NPD3641	Approved
0.6497	Remote Similarity	NPD3640	Phase 3
0.6493	Remote Similarity	NPD5041	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7608	Discontinued
0.6474	Remote Similarity	NPD2654	Approved
0.6471	Remote Similarity	NPD4705	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD5005	Approved
0.6468	Remote Similarity	NPD5006	Approved
0.6462	Remote Similarity	NPD7668	Phase 2
0.6453	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD8031	Discontinued
0.6444	Remote Similarity	NPD4424	Discontinued
0.6437	Remote Similarity	NPD5481	Discontinued
0.6432	Remote Similarity	NPD6457	Approved
0.6432	Remote Similarity	NPD7485	Phase 3
0.6432	Remote Similarity	NPD5071	Phase 2
0.6432	Remote Similarity	NPD7484	Phase 3
0.6429	Remote Similarity	NPD5745	Approved
0.6425	Remote Similarity	NPD3154	Approved
0.6425	Remote Similarity	NPD6357	Discontinued
0.6425	Remote Similarity	NPD3153	Approved
0.6424	Remote Similarity	NPD7018	Phase 2
0.6422	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6297	Approved
0.642	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD2492	Phase 1
0.6411	Remote Similarity	NPD7047	Phase 3
0.641	Remote Similarity	NPD4258	Approved
0.641	Remote Similarity	NPD4259	Approved
0.6408	Remote Similarity	NPD5914	Approved
0.6404	Remote Similarity	NPD7427	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data