NPASS Compound

Structure

CID95366 OpenBabel06191715432D 26 28 0 0 0 0 0 0 0 0999 V2000 5.4041 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2701 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5380 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1361 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0021 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8682 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1002 -5.5170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1002 -5.5170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7342 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4092 -4.5659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7912 -4.5659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6002 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6002 -3.9781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 11.4662 -2.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -0.8090 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 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 22 1 0 0 0 0 13 14 2 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 23 1 0 0 0 0 16 23 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 25 1 0 0 0 0 18 26 1 0 0 0 0 20 21 2 0 0 0 0 20 25 1 0 0 0 0 21 26 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:	355.21
Volume:	384.947
LogP:	5.417
LogD:	3.967
LogS:	-5.856
# Rotatable Bonds:	10
TPSA:	38.77
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.368
Synthetic Accessibility Score:	2.442
Fsp3:	0.5
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:	-4.87
MDCK Permeability:	2.7194533686270006e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.977
30% Bioavailability (F30%):	0.66

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.141
Plasma Protein Binding (PPB):	98.07816314697266%
Volume Distribution (VD):	1.403
Pgp-substrate:	1.8347855806350708%

ADMET: Metabolism

CYP1A2-inhibitor:	0.931
CYP1A2-substrate:	0.3
CYP2C19-inhibitor:	0.863
CYP2C19-substrate:	0.449
CYP2C9-inhibitor:	0.386
CYP2C9-substrate:	0.771
CYP2D6-inhibitor:	0.972
CYP2D6-substrate:	0.908
CYP3A4-inhibitor:	0.97
CYP3A4-substrate:	0.29

ADMET: Excretion

Clearance (CL):	8.659
Half-life (T1/2):	0.336

ADMET: Toxicity

hERG Blockers:	0.763
Human Hepatotoxicity (H-HT):	0.634
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.463
Skin Sensitization:	0.98
Carcinogencity:	0.763
Eye Corrosion:	0.047
Eye Irritation:	0.13
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC95366

Natural Product ID:	NPC95366
*Common Name:**	11-(Benzo[D][1,3]Dioxol-5-Yl)-1-(Pyrrolidin-1-Yl)Undeca-2,4-Dien-1-One
IUPAC Name:	(2E,4E)-11-(1,3-benzodioxol-5-yl)-1-pyrrolidin-1-ylundeca-2,4-dien-1-one
Synonyms:
Standard InCHIKey:	HQVOLKBRDWRKFF-RZYXTZOYSA-N
Standard InCHI:	InChI=1S/C22H29NO3/c24-22(23-15-9-10-16-23)12-8-6-4-2-1-3-5-7-11-19-13-14-20-21(17-19)26-18-25-20/h4,6,8,12-14,17H,1-3,5,7,9-11,15-16,18H2/b6-4+,12-8+
SMILES:	O=C(N1CCCC1)/C=C/C=C/CCCCCCc1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338735
PubChem CID:	10594373
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	whole plant	Luxi County, Yunnan Province, China	2008-OCT	PMID[21158422]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21158422]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	8
Others	1

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	14420.0	nM	PMID[532979]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	22010.0	nM	PMID[532979]
NPT133	Cell Line	ZR-75-1	Homo sapiens	IC50	=	26710.0	nM	PMID[532979]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	30110.0	nM	PMID[532979]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	31580.0	nM	PMID[532979]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	16020.0	nM	PMID[532979]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	16920.0	nM	PMID[532979]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	15420.0	nM	PMID[532979]
NPT2	Others	Unspecified		Ratio IC50	=	1.1	n.a.	PMID[532979]

☑ 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 NPC95366 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	250
0.1-0.2	1421
0.2-0.3	5973
0.3-0.4	12462
0.4-0.5	5981
0.5-0.6	13006
0.6-0.7	3171
0.7-0.8	395
0.8-0.85	9
0.85-0.9	2
0.9-0.95	15
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC248505
0.9922	High Similarity	NPC137172
0.9922	High Similarity	NPC145446
0.9845	High Similarity	NPC96406
0.9767	High Similarity	NPC45783
0.9767	High Similarity	NPC193673
0.9767	High Similarity	NPC103947
0.9767	High Similarity	NPC328419
0.9767	High Similarity	NPC94280
0.9767	High Similarity	NPC159150
0.9612	High Similarity	NPC217574
0.9398	High Similarity	NPC252107
0.9323	High Similarity	NPC99078
0.9313	High Similarity	NPC318862
0.9254	High Similarity	NPC220923
0.9248	High Similarity	NPC205178
0.9248	High Similarity	NPC136330
0.9248	High Similarity	NPC251454
0.9248	High Similarity	NPC196609
0.9248	High Similarity	NPC230698
0.9248	High Similarity	NPC277042
0.9248	High Similarity	NPC255817
0.9248	High Similarity	NPC73883
0.9173	High Similarity	NPC167096
0.9111	High Similarity	NPC28641
0.9111	High Similarity	NPC194359
0.9111	High Similarity	NPC470707
0.8696	High Similarity	NPC225745
0.8686	High Similarity	NPC180647
0.863	High Similarity	NPC270811
0.863	High Similarity	NPC471073
0.8623	High Similarity	NPC469808
0.8462	Intermediate Similarity	NPC244338
0.8389	Intermediate Similarity	NPC169742
0.8369	Intermediate Similarity	NPC231572
0.8243	Intermediate Similarity	NPC223125
0.8151	Intermediate Similarity	NPC469978
0.8133	Intermediate Similarity	NPC223124
0.8129	Intermediate Similarity	NPC231198
0.8079	Intermediate Similarity	NPC470708
0.8071	Intermediate Similarity	NPC118419
0.8045	Intermediate Similarity	NPC69670
0.8042	Intermediate Similarity	NPC113236
0.8042	Intermediate Similarity	NPC214036
0.7986	Intermediate Similarity	NPC246974
0.7986	Intermediate Similarity	NPC147247
0.7955	Intermediate Similarity	NPC111225
0.7933	Intermediate Similarity	NPC470088
0.7914	Intermediate Similarity	NPC191302
0.7914	Intermediate Similarity	NPC99798
0.7914	Intermediate Similarity	NPC64948
0.7914	Intermediate Similarity	NPC157740
0.7907	Intermediate Similarity	NPC31279
0.7902	Intermediate Similarity	NPC11147
0.7895	Intermediate Similarity	NPC212643
0.7895	Intermediate Similarity	NPC199209
0.7868	Intermediate Similarity	NPC80241
0.7868	Intermediate Similarity	NPC114845
0.7868	Intermediate Similarity	NPC301641
0.7847	Intermediate Similarity	NPC7018
0.7842	Intermediate Similarity	NPC156944
0.7842	Intermediate Similarity	NPC251466
0.7829	Intermediate Similarity	NPC474852
0.781	Intermediate Similarity	NPC256167
0.7793	Intermediate Similarity	NPC193528
0.7792	Intermediate Similarity	NPC76079
0.7792	Intermediate Similarity	NPC78733
0.7786	Intermediate Similarity	NPC291449
0.7786	Intermediate Similarity	NPC41331
0.7778	Intermediate Similarity	NPC57501
0.777	Intermediate Similarity	NPC207541
0.777	Intermediate Similarity	NPC85830
0.777	Intermediate Similarity	NPC170583
0.777	Intermediate Similarity	NPC71105
0.777	Intermediate Similarity	NPC246133
0.777	Intermediate Similarity	NPC152186
0.777	Intermediate Similarity	NPC182147
0.7756	Intermediate Similarity	NPC106786
0.7748	Intermediate Similarity	NPC475959
0.773	Intermediate Similarity	NPC469977
0.7724	Intermediate Similarity	NPC416184
0.7722	Intermediate Similarity	NPC59567
0.7721	Intermediate Similarity	NPC344161
0.7714	Intermediate Similarity	NPC218323
0.7708	Intermediate Similarity	NPC473463
0.7698	Intermediate Similarity	NPC300955
0.7692	Intermediate Similarity	NPC127326
0.7676	Intermediate Similarity	NPC470706
0.7676	Intermediate Similarity	NPC476748
0.7671	Intermediate Similarity	NPC230968
0.7671	Intermediate Similarity	NPC102260
0.7667	Intermediate Similarity	NPC145304
0.7662	Intermediate Similarity	NPC148898
0.7662	Intermediate Similarity	NPC233029
0.7662	Intermediate Similarity	NPC210148
0.766	Intermediate Similarity	NPC172403
0.7655	Intermediate Similarity	NPC475828
0.764	Intermediate Similarity	NPC241055
0.764	Intermediate Similarity	NPC86469
0.7628	Intermediate Similarity	NPC31311
0.7628	Intermediate Similarity	NPC234392
0.7622	Intermediate Similarity	NPC477694
0.7622	Intermediate Similarity	NPC477705
0.7619	Intermediate Similarity	NPC166184
0.7595	Intermediate Similarity	NPC215829
0.7595	Intermediate Similarity	NPC97072
0.7589	Intermediate Similarity	NPC40352
0.7589	Intermediate Similarity	NPC213711
0.7586	Intermediate Similarity	NPC282477
0.7586	Intermediate Similarity	NPC284855
0.7582	Intermediate Similarity	NPC469539
0.7582	Intermediate Similarity	NPC469540
0.7569	Intermediate Similarity	NPC477706
0.7568	Intermediate Similarity	NPC178290
0.7561	Intermediate Similarity	NPC308267
0.7554	Intermediate Similarity	NPC298486
0.7545	Intermediate Similarity	NPC102760
0.7535	Intermediate Similarity	NPC158737
0.7535	Intermediate Similarity	NPC177167
0.7535	Intermediate Similarity	NPC286683
0.7517	Intermediate Similarity	NPC278076
0.7517	Intermediate Similarity	NPC275150
0.75	Intermediate Similarity	NPC249788
0.7484	Intermediate Similarity	NPC165797
0.7483	Intermediate Similarity	NPC226862
0.7483	Intermediate Similarity	NPC165128
0.7483	Intermediate Similarity	NPC158471
0.7483	Intermediate Similarity	NPC57119
0.7482	Intermediate Similarity	NPC193484
0.7469	Intermediate Similarity	NPC474324
0.7469	Intermediate Similarity	NPC57812
0.7468	Intermediate Similarity	NPC211296
0.7467	Intermediate Similarity	NPC908
0.7467	Intermediate Similarity	NPC138438
0.7466	Intermediate Similarity	NPC205915
0.7453	Intermediate Similarity	NPC168409
0.7452	Intermediate Similarity	NPC216459
0.7452	Intermediate Similarity	NPC41178
0.7452	Intermediate Similarity	NPC138487
0.745	Intermediate Similarity	NPC318575
0.7439	Intermediate Similarity	NPC67978
0.7439	Intermediate Similarity	NPC303581
0.7432	Intermediate Similarity	NPC254610
0.7431	Intermediate Similarity	NPC160193
0.7423	Intermediate Similarity	NPC475845
0.7421	Intermediate Similarity	NPC477080
0.7415	Intermediate Similarity	NPC19890
0.7415	Intermediate Similarity	NPC110958
0.7405	Intermediate Similarity	NPC146288
0.7397	Intermediate Similarity	NPC266425
0.7396	Intermediate Similarity	NPC83511
0.7394	Intermediate Similarity	NPC17348
0.7391	Intermediate Similarity	NPC320104
0.7391	Intermediate Similarity	NPC218614
0.7391	Intermediate Similarity	NPC119949
0.7379	Intermediate Similarity	NPC171550
0.7379	Intermediate Similarity	NPC134764
0.7379	Intermediate Similarity	NPC233224
0.7379	Intermediate Similarity	NPC271208
0.7378	Intermediate Similarity	NPC474708
0.7372	Intermediate Similarity	NPC476579
0.7372	Intermediate Similarity	NPC120075
0.7372	Intermediate Similarity	NPC119669
0.7368	Intermediate Similarity	NPC179309
0.7365	Intermediate Similarity	NPC42793
0.7365	Intermediate Similarity	NPC231884
0.7365	Intermediate Similarity	NPC167944
0.7349	Intermediate Similarity	NPC181905
0.7346	Intermediate Similarity	NPC306669
0.7346	Intermediate Similarity	NPC247972
0.7343	Intermediate Similarity	NPC274356
0.7342	Intermediate Similarity	NPC93593
0.7338	Intermediate Similarity	NPC95075
0.7338	Intermediate Similarity	NPC253883
0.7338	Intermediate Similarity	NPC90844
0.7333	Intermediate Similarity	NPC314682
0.7329	Intermediate Similarity	NPC82111
0.7329	Intermediate Similarity	NPC192255
0.7329	Intermediate Similarity	NPC227160
0.7321	Intermediate Similarity	NPC149285
0.732	Intermediate Similarity	NPC15743
0.732	Intermediate Similarity	NPC327623
0.732	Intermediate Similarity	NPC50696
0.7319	Intermediate Similarity	NPC277460
0.7317	Intermediate Similarity	NPC475686
0.7317	Intermediate Similarity	NPC158148
0.7317	Intermediate Similarity	NPC82533
0.7317	Intermediate Similarity	NPC266176
0.7317	Intermediate Similarity	NPC58766
0.7317	Intermediate Similarity	NPC290759
0.731	Intermediate Similarity	NPC169387
0.731	Intermediate Similarity	NPC471650
0.731	Intermediate Similarity	NPC477259
0.7308	Intermediate Similarity	NPC292792
0.7305	Intermediate Similarity	NPC474470
0.7301	Intermediate Similarity	NPC476002
0.7299	Intermediate Similarity	NPC268317
0.7294	Intermediate Similarity	NPC116007
0.7292	Intermediate Similarity	NPC100129
0.729	Intermediate Similarity	NPC37144

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 NPC95366 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	744
0.2-0.3	1069
0.3-0.4	2513
0.4-0.5	2620
0.5-0.6	1497
0.6-0.7	486
0.7-0.8	44
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9248	High Similarity	NPD2492	Phase 1
0.8207	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD5297	Approved
0.7817	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD4210	Discontinued
0.7606	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7281	Phase 3
0.759	Intermediate Similarity	NPD7280	Phase 3
0.7552	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5718	Phase 2
0.7372	Intermediate Similarity	NPD824	Approved
0.7365	Intermediate Similarity	NPD6896	Approved
0.7365	Intermediate Similarity	NPD6895	Approved
0.7357	Intermediate Similarity	NPD3705	Approved
0.7355	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4236	Phase 3
0.7351	Intermediate Similarity	NPD4237	Approved
0.7338	Intermediate Similarity	NPD3146	Approved
0.7338	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2653	Approved
0.7285	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6873	Phase 2
0.7266	Intermediate Similarity	NPD1357	Approved
0.7254	Intermediate Similarity	NPD1420	Approved
0.7254	Intermediate Similarity	NPD1421	Approved
0.725	Intermediate Similarity	NPD5977	Approved
0.725	Intermediate Similarity	NPD5978	Approved
0.7248	Intermediate Similarity	NPD6111	Discontinued
0.7248	Intermediate Similarity	NPD743	Approved
0.7246	Intermediate Similarity	NPD5536	Phase 2
0.7215	Intermediate Similarity	NPD6875	Approved
0.7215	Intermediate Similarity	NPD6876	Approved
0.7214	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD5283	Phase 1
0.7195	Intermediate Similarity	NPD4166	Phase 2
0.717	Intermediate Similarity	NPD6386	Approved
0.717	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7110	Phase 1
0.717	Intermediate Similarity	NPD6385	Approved
0.7143	Intermediate Similarity	NPD2219	Phase 1
0.7143	Intermediate Similarity	NPD3885	Approved
0.7125	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1375	Discontinued
0.7095	Intermediate Similarity	NPD2674	Phase 3
0.7095	Intermediate Similarity	NPD2245	Discovery
0.7092	Intermediate Similarity	NPD2667	Approved
0.7092	Intermediate Similarity	NPD2668	Approved
0.7081	Intermediate Similarity	NPD2978	Approved
0.7081	Intermediate Similarity	NPD2977	Approved
0.7067	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2040	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5604	Discontinued
0.7051	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2161	Phase 2
0.7025	Intermediate Similarity	NPD3640	Phase 3
0.7025	Intermediate Similarity	NPD1670	Discontinued
0.7025	Intermediate Similarity	NPD3641	Approved
0.7025	Intermediate Similarity	NPD3639	Approved
0.7011	Intermediate Similarity	NPD3349	Phase 2
0.7006	Intermediate Similarity	NPD4584	Approved
0.6987	Remote Similarity	NPD7124	Phase 2
0.6986	Remote Similarity	NPD7018	Phase 2
0.6975	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5582	Discontinued
0.6944	Remote Similarity	NPD2232	Approved
0.6944	Remote Similarity	NPD2233	Approved
0.6944	Remote Similarity	NPD2230	Approved
0.6943	Remote Similarity	NPD4357	Discontinued
0.6934	Remote Similarity	NPD228	Approved
0.6933	Remote Similarity	NPD3142	Approved
0.6933	Remote Similarity	NPD3140	Approved
0.6932	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3596	Phase 2
0.6923	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5241	Discontinued
0.6918	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5976	Discontinued
0.6914	Remote Similarity	NPD7248	Discontinued
0.6913	Remote Similarity	NPD3144	Approved
0.6913	Remote Similarity	NPD3145	Approved
0.6906	Remote Similarity	NPD5457	Discontinued
0.6905	Remote Similarity	NPD2898	Approved
0.6903	Remote Similarity	NPD5177	Phase 3
0.6903	Remote Similarity	NPD4162	Approved
0.6903	Remote Similarity	NPD3060	Approved
0.6899	Remote Similarity	NPD4739	Approved
0.6897	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4207	Discontinued
0.6889	Remote Similarity	NPD1358	Approved
0.6879	Remote Similarity	NPD2120	Phase 2
0.6871	Remote Similarity	NPD7905	Discontinued
0.6871	Remote Similarity	NPD4585	Approved
0.6859	Remote Similarity	NPD5754	Discontinued
0.6859	Remote Similarity	NPD5481	Discontinued
0.6849	Remote Similarity	NPD2922	Phase 1
0.6849	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD5746	Approved
0.6839	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7037	Approved
0.6832	Remote Similarity	NPD4017	Approved
0.6829	Remote Similarity	NPD2563	Approved
0.6829	Remote Similarity	NPD2560	Approved
0.6815	Remote Similarity	NPD3134	Approved
0.68	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7296	Approved
0.6797	Remote Similarity	NPD7119	Phase 2
0.6796	Remote Similarity	NPD4420	Approved
0.679	Remote Similarity	NPD7028	Phase 2
0.6784	Remote Similarity	NPD5313	Approved
0.6784	Remote Similarity	NPD5312	Approved
0.6783	Remote Similarity	NPD5691	Approved
0.677	Remote Similarity	NPD3686	Approved
0.677	Remote Similarity	NPD3687	Approved
0.6768	Remote Similarity	NPD5773	Approved
0.6768	Remote Similarity	NPD5772	Approved
0.6766	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6584	Phase 3
0.6755	Remote Similarity	NPD3531	Approved
0.6755	Remote Similarity	NPD5745	Approved
0.6755	Remote Similarity	NPD3532	Approved
0.6755	Remote Similarity	NPD3530	Approved
0.6753	Remote Similarity	NPD4108	Discontinued
0.6752	Remote Similarity	NPD6331	Phase 2
0.675	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5090	Approved
0.6748	Remote Similarity	NPD5089	Approved
0.6746	Remote Similarity	NPD5242	Approved
0.6743	Remote Similarity	NPD6618	Phase 2
0.674	Remote Similarity	NPD5564	Approved
0.6736	Remote Similarity	NPD4626	Approved
0.6733	Remote Similarity	NPD5163	Phase 2
0.6731	Remote Similarity	NPD7153	Discontinued
0.6728	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5353	Approved
0.6723	Remote Similarity	NPD7291	Discontinued
0.6723	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6580	Approved
0.6713	Remote Similarity	NPD6581	Approved
0.6711	Remote Similarity	NPD3109	Approved
0.6711	Remote Similarity	NPD2237	Approved
0.6711	Remote Similarity	NPD3110	Approved
0.671	Remote Similarity	NPD6032	Approved
0.6708	Remote Similarity	NPD6031	Approved
0.6708	Remote Similarity	NPD4727	Phase 1
0.6708	Remote Similarity	NPD6030	Approved
0.6707	Remote Similarity	NPD3383	Approved
0.6707	Remote Similarity	NPD3382	Approved
0.6707	Remote Similarity	NPD3384	Approved
0.6706	Remote Similarity	NPD4481	Phase 3
0.6705	Remote Similarity	NPD6297	Approved
0.6689	Remote Similarity	NPD5109	Approved
0.6689	Remote Similarity	NPD1039	Discontinued
0.6689	Remote Similarity	NPD5111	Phase 2
0.6689	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD5110	Phase 2
0.6688	Remote Similarity	NPD2654	Approved
0.6687	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2335	Discontinued
0.6687	Remote Similarity	NPD1424	Approved
0.6685	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6382	Discontinued
0.6667	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3685	Discontinued
0.6667	Remote Similarity	NPD3656	Approved
0.6667	Remote Similarity	NPD3444	Approved
0.6667	Remote Similarity	NPD1669	Approved
0.6667	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3443	Approved
0.6667	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3445	Approved
0.6649	Remote Similarity	NPD4859	Phase 1
0.6649	Remote Similarity	NPD5005	Approved
0.6649	Remote Similarity	NPD5006	Approved
0.6647	Remote Similarity	NPD7833	Phase 2
0.6647	Remote Similarity	NPD2388	Discontinued
0.6647	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7831	Phase 2
0.6646	Remote Similarity	NPD4110	Phase 3
0.6646	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4772	Phase 2
0.6646	Remote Similarity	NPD4773	Phase 2
0.6646	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2164	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD776	Approved
0.6627	Remote Similarity	NPD6107	Approved
0.6624	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2157	Approved
0.662	Remote Similarity	NPD2557	Approved

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