NPASS Compound

Structure

CID194359 OpenBabel06191715582D 25 27 0 0 0 0 0 0 0 0999 V2000 6.1472 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9773 -1.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9773 -1.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2864 -0.3968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6683 -0.3968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4773 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4773 0.1910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 11.3434 1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 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 1 0 0 0 0 5 7 1 0 0 0 0 6 10 2 0 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 18 1 0 0 0 0 11 21 1 0 0 0 0 12 13 2 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 22 1 0 0 0 0 15 22 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 24 1 0 0 0 0 17 25 1 0 0 0 0 19 20 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	343.21
Volume:	370.288
LogP:	4.389
LogD:	3.66
LogS:	-4.548
# 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:	0.606
Synthetic Accessibility Score:	2.222
Fsp3:	0.571
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:	-4.86
MDCK Permeability:	2.8283262508921325e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.234
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.274

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.925
Plasma Protein Binding (PPB):	96.61122131347656%
Volume Distribution (VD):	1.022
Pgp-substrate:	2.41672945022583%

ADMET: Metabolism

CYP1A2-inhibitor:	0.942
CYP1A2-substrate:	0.226
CYP2C19-inhibitor:	0.882
CYP2C19-substrate:	0.151
CYP2C9-inhibitor:	0.618
CYP2C9-substrate:	0.886
CYP2D6-inhibitor:	0.945
CYP2D6-substrate:	0.815
CYP3A4-inhibitor:	0.96
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	11.837
Half-life (T1/2):	0.267

ADMET: Toxicity

hERG Blockers:	0.858
Human Hepatotoxicity (H-HT):	0.156
Drug-inuced Liver Injury (DILI):	0.708
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.193
Skin Sensitization:	0.957
Carcinogencity:	0.595
Eye Corrosion:	0.011
Eye Irritation:	0.108
Respiratory Toxicity:	0.451

Download Data

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

Natural Product: NPC194359

Natural Product ID:	NPC194359
*Common Name:**	1-[(9E)-10-(3,4-Methylenedioxyphenyl)-9-Decenoyl]Pyrrolidine
IUPAC Name:	(E)-10-(1,3-benzodioxol-5-yl)-1-pyrrolidin-1-yldec-9-en-1-one
Synonyms:
Standard InCHIKey:	HRMXETZEKQCWBC-UXBLZVDNSA-N
Standard InCHI:	InChI=1S/C21H29NO3/c23-21(22-14-8-9-15-22)11-7-5-3-1-2-4-6-10-18-12-13-19-20(16-18)25-17-24-19/h6,10,12-13,16H,1-5,7-9,11,14-15,17H2/b10-6+
SMILES:	C(CC/C=C/c1ccc2c(c1)OCO2)CCCCC(=O)N1CCCC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669575
PubChem CID:	16041826
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	9
Others	1

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2.67	ug.mL-1	PMID[447786]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	25740.0	nM	PMID[447787]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	27680.0	nM	PMID[447787]
NPT133	Cell Line	ZR-75-1	Homo sapiens	IC50	=	40930.0	nM	PMID[447787]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	40000.0	nM	PMID[447787]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	40000.0	nM	PMID[447787]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	23680.0	nM	PMID[447787]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	23740.0	nM	PMID[447787]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	20700.0	nM	PMID[447787]
NPT2	Others	Unspecified		Ratio IC50	=	1.1	n.a.	PMID[447787]

☑ 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 NPC194359 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	234
0.1-0.2	1349
0.2-0.3	5858
0.3-0.4	12762
0.4-0.5	5753
0.5-0.6	13341
0.6-0.7	2971
0.7-0.8	393
0.8-0.85	6
0.85-0.9	13
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC28641
0.9612	High Similarity	NPC318862
0.9545	High Similarity	NPC225745
0.9394	High Similarity	NPC180647
0.9248	High Similarity	NPC96406
0.9179	High Similarity	NPC137172
0.9179	High Similarity	NPC145446
0.9173	High Similarity	NPC94280
0.9173	High Similarity	NPC159150
0.9173	High Similarity	NPC193673
0.9173	High Similarity	NPC328419
0.9173	High Similarity	NPC103947
0.9173	High Similarity	NPC45783
0.9111	High Similarity	NPC248505
0.9111	High Similarity	NPC95366
0.9023	High Similarity	NPC217574
0.8897	High Similarity	NPC99078
0.8832	High Similarity	NPC252107
0.8832	High Similarity	NPC220923
0.8824	High Similarity	NPC196609
0.8824	High Similarity	NPC73883
0.8824	High Similarity	NPC205178
0.8824	High Similarity	NPC136330
0.8824	High Similarity	NPC251454
0.8824	High Similarity	NPC255817
0.8824	High Similarity	NPC230698
0.8824	High Similarity	NPC277042
0.875	High Similarity	NPC167096
0.8696	High Similarity	NPC470707
0.8514	High Similarity	NPC169742
0.8403	Intermediate Similarity	NPC469978
0.8322	Intermediate Similarity	NPC470708
0.8176	Intermediate Similarity	NPC470088
0.8099	Intermediate Similarity	NPC469808
0.8013	Intermediate Similarity	NPC471073
0.8013	Intermediate Similarity	NPC270811
0.7959	Intermediate Similarity	NPC244338
0.7866	Intermediate Similarity	NPC102760
0.7862	Intermediate Similarity	NPC231572
0.7857	Intermediate Similarity	NPC469977
0.7842	Intermediate Similarity	NPC156944
0.7842	Intermediate Similarity	NPC251466
0.7832	Intermediate Similarity	NPC205915
0.7832	Intermediate Similarity	NPC473463
0.7817	Intermediate Similarity	NPC118419
0.7801	Intermediate Similarity	NPC470706
0.7786	Intermediate Similarity	NPC99798
0.7786	Intermediate Similarity	NPC291449
0.7786	Intermediate Similarity	NPC157740
0.7786	Intermediate Similarity	NPC191302
0.7786	Intermediate Similarity	NPC41331
0.7778	Intermediate Similarity	NPC19890
0.7778	Intermediate Similarity	NPC110958
0.777	Intermediate Similarity	NPC207541
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
0.7769	Intermediate Similarity	NPC31279
0.7763	Intermediate Similarity	NPC223125
0.7746	Intermediate Similarity	NPC477694
0.7746	Intermediate Similarity	NPC477705
0.773	Intermediate Similarity	NPC147247
0.773	Intermediate Similarity	NPC246974
0.7724	Intermediate Similarity	NPC7018
0.7724	Intermediate Similarity	NPC416184
0.7698	Intermediate Similarity	NPC300955
0.7697	Intermediate Similarity	NPC469539
0.7697	Intermediate Similarity	NPC469540
0.7692	Intermediate Similarity	NPC127326
0.7692	Intermediate Similarity	NPC477706
0.7681	Intermediate Similarity	NPC256167
0.7673	Intermediate Similarity	NPC231198
0.7671	Intermediate Similarity	NPC230968
0.7671	Intermediate Similarity	NPC102260
0.7662	Intermediate Similarity	NPC223124
0.766	Intermediate Similarity	NPC172403
0.766	Intermediate Similarity	NPC286683
0.7655	Intermediate Similarity	NPC11147
0.7647	Intermediate Similarity	NPC69670
0.764	Intermediate Similarity	NPC86469
0.7639	Intermediate Similarity	NPC266425
0.7609	Intermediate Similarity	NPC80241
0.7609	Intermediate Similarity	NPC301641
0.7605	Intermediate Similarity	NPC83511
0.7586	Intermediate Similarity	NPC282477
0.7586	Intermediate Similarity	NPC284855
0.7584	Intermediate Similarity	NPC908
0.7584	Intermediate Similarity	NPC138438
0.7564	Intermediate Similarity	NPC76079
0.7564	Intermediate Similarity	NPC78733
0.7561	Intermediate Similarity	NPC308267
0.7556	Intermediate Similarity	NPC111225
0.7554	Intermediate Similarity	NPC298486
0.7551	Intermediate Similarity	NPC193528
0.7551	Intermediate Similarity	NPC113236
0.7551	Intermediate Similarity	NPC214036
0.755	Intermediate Similarity	NPC145304
0.7535	Intermediate Similarity	NPC64948
0.7518	Intermediate Similarity	NPC120066
0.7516	Intermediate Similarity	NPC475959
0.75	Intermediate Similarity	NPC212643
0.75	Intermediate Similarity	NPC52968
0.75	Intermediate Similarity	NPC199209
0.75	Intermediate Similarity	NPC116007
0.75	Intermediate Similarity	NPC231719
0.7484	Intermediate Similarity	NPC119669
0.7482	Intermediate Similarity	NPC114845
0.7468	Intermediate Similarity	NPC470082
0.7467	Intermediate Similarity	NPC282291
0.7467	Intermediate Similarity	NPC218092
0.7467	Intermediate Similarity	NPC246474
0.7467	Intermediate Similarity	NPC162851
0.7467	Intermediate Similarity	NPC166137
0.7464	Intermediate Similarity	NPC344161
0.7445	Intermediate Similarity	NPC205502
0.7439	Intermediate Similarity	NPC67978
0.7439	Intermediate Similarity	NPC303581
0.7436	Intermediate Similarity	NPC148898
0.7436	Intermediate Similarity	NPC233029
0.7436	Intermediate Similarity	NPC210148
0.7432	Intermediate Similarity	NPC254610
0.7431	Intermediate Similarity	NPC476748
0.7425	Intermediate Similarity	NPC149285
0.7423	Intermediate Similarity	NPC241055
0.7417	Intermediate Similarity	NPC210354
0.7417	Intermediate Similarity	NPC176586
0.7415	Intermediate Similarity	NPC475828
0.7413	Intermediate Similarity	NPC223807
0.7412	Intermediate Similarity	NPC477259
0.7412	Intermediate Similarity	NPC169387
0.7405	Intermediate Similarity	NPC234392
0.7405	Intermediate Similarity	NPC31311
0.7391	Intermediate Similarity	NPC57501
0.7383	Intermediate Similarity	NPC14022
0.7378	Intermediate Similarity	NPC474708
0.7375	Intermediate Similarity	NPC215829
0.7375	Intermediate Similarity	NPC97072
0.7372	Intermediate Similarity	NPC474852
0.7372	Intermediate Similarity	NPC120075
0.7368	Intermediate Similarity	NPC472564
0.7368	Intermediate Similarity	NPC474288
0.7365	Intermediate Similarity	NPC106606
0.7361	Intermediate Similarity	NPC283079
0.7357	Intermediate Similarity	NPC201777
0.7356	Intermediate Similarity	NPC470646
0.7355	Intermediate Similarity	NPC211296
0.7351	Intermediate Similarity	NPC323601
0.7343	Intermediate Similarity	NPC213711
0.7343	Intermediate Similarity	NPC40352
0.7343	Intermediate Similarity	NPC218323
0.7329	Intermediate Similarity	NPC469479
0.732	Intermediate Similarity	NPC191158
0.732	Intermediate Similarity	NPC15743
0.732	Intermediate Similarity	NPC177644
0.7317	Intermediate Similarity	NPC475845
0.731	Intermediate Similarity	NPC160193
0.731	Intermediate Similarity	NPC471650
0.7303	Intermediate Similarity	NPC151423
0.7303	Intermediate Similarity	NPC40237
0.7301	Intermediate Similarity	NPC474858
0.7292	Intermediate Similarity	NPC177167
0.7292	Intermediate Similarity	NPC158737
0.7285	Intermediate Similarity	NPC275150
0.7285	Intermediate Similarity	NPC470855
0.7284	Intermediate Similarity	NPC218614
0.7278	Intermediate Similarity	NPC292003
0.7273	Intermediate Similarity	NPC474158
0.7273	Intermediate Similarity	NPC85830
0.7273	Intermediate Similarity	NPC327052
0.7273	Intermediate Similarity	NPC280767
0.7267	Intermediate Similarity	NPC166184
0.7267	Intermediate Similarity	NPC165797
0.7267	Intermediate Similarity	NPC141440
0.7267	Intermediate Similarity	NPC26353
0.7266	Intermediate Similarity	NPC119949
0.7266	Intermediate Similarity	NPC299406
0.7256	Intermediate Similarity	NPC474324
0.7256	Intermediate Similarity	NPC57812
0.7254	Intermediate Similarity	NPC4181
0.7254	Intermediate Similarity	NPC244876
0.7254	Intermediate Similarity	NPC164778
0.7254	Intermediate Similarity	NPC163083
0.7254	Intermediate Similarity	NPC257976
0.7254	Intermediate Similarity	NPC249788
0.7254	Intermediate Similarity	NPC242372
0.7248	Intermediate Similarity	NPC167944
0.7248	Intermediate Similarity	NPC42793
0.7248	Intermediate Similarity	NPC231884
0.7246	Intermediate Similarity	NPC33271
0.7241	Intermediate Similarity	NPC226862
0.7241	Intermediate Similarity	NPC158471
0.7241	Intermediate Similarity	NPC57119
0.7241	Intermediate Similarity	NPC165128
0.7239	Intermediate Similarity	NPC168409
0.7239	Intermediate Similarity	NPC469505
0.7239	Intermediate Similarity	NPC35345
0.7237	Intermediate Similarity	NPC28398
0.7234	Intermediate Similarity	NPC177291

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 NPC194359 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	691
0.2-0.3	1109
0.3-0.4	2444
0.4-0.5	2577
0.5-0.6	1582
0.6-0.7	522
0.7-0.8	55
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD2492	Phase 1
0.8082	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7281	Phase 3
0.7914	Intermediate Similarity	NPD7280	Phase 3
0.7817	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD3146	Approved
0.78	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7110	Phase 1
0.7727	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6875	Approved
0.7662	Intermediate Similarity	NPD6876	Approved
0.7647	Intermediate Similarity	NPD4210	Discontinued
0.7616	Intermediate Similarity	NPD5297	Approved
0.7606	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD824	Approved
0.7552	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5718	Phase 2
0.7483	Intermediate Similarity	NPD743	Approved
0.7415	Intermediate Similarity	NPD2653	Approved
0.7389	Intermediate Similarity	NPD6873	Phase 2
0.7389	Intermediate Similarity	NPD6385	Approved
0.7389	Intermediate Similarity	NPD6386	Approved
0.7355	Intermediate Similarity	NPD3640	Phase 3
0.7355	Intermediate Similarity	NPD3639	Approved
0.7355	Intermediate Similarity	NPD3641	Approved
0.7351	Intermediate Similarity	NPD4236	Phase 3
0.7351	Intermediate Similarity	NPD4237	Approved
0.7342	Intermediate Similarity	NPD7248	Discontinued
0.7266	Intermediate Similarity	NPD1357	Approved
0.725	Intermediate Similarity	NPD5977	Approved
0.725	Intermediate Similarity	NPD5978	Approved
0.7248	Intermediate Similarity	NPD6896	Approved
0.7248	Intermediate Similarity	NPD6895	Approved
0.7235	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3705	Approved
0.72	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4166	Phase 2
0.7172	Intermediate Similarity	NPD2040	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3140	Approved
0.7162	Intermediate Similarity	NPD3142	Approved
0.7161	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3885	Approved
0.7134	Intermediate Similarity	NPD1670	Discontinued
0.7133	Intermediate Similarity	NPD1420	Approved
0.7133	Intermediate Similarity	NPD6111	Discontinued
0.7133	Intermediate Similarity	NPD1421	Approved
0.7122	Intermediate Similarity	NPD5536	Phase 2
0.7101	Intermediate Similarity	NPD6297	Approved
0.7095	Intermediate Similarity	NPD2245	Discovery
0.7092	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4124	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7296	Approved
0.7083	Intermediate Similarity	NPD5313	Approved
0.7083	Intermediate Similarity	NPD5312	Approved
0.7081	Intermediate Similarity	NPD2978	Approved
0.7081	Intermediate Similarity	NPD2977	Approved
0.7059	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2219	Phase 1
0.7029	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2654	Approved
0.7	Intermediate Similarity	NPD5457	Discontinued
0.6993	Remote Similarity	NPD1375	Discontinued
0.698	Remote Similarity	NPD2674	Phase 3
0.6972	Remote Similarity	NPD2667	Approved
0.6972	Remote Similarity	NPD2668	Approved
0.6968	Remote Similarity	NPD4110	Phase 3
0.6968	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5283	Phase 1
0.6954	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5604	Discontinued
0.6936	Remote Similarity	NPD6853	Approved
0.6936	Remote Similarity	NPD6851	Approved
0.6928	Remote Similarity	NPD2161	Phase 2
0.6928	Remote Similarity	NPD2240	Approved
0.6928	Remote Similarity	NPD2239	Approved
0.6923	Remote Similarity	NPD5241	Discontinued
0.6919	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7131	Phase 3
0.6913	Remote Similarity	NPD3144	Approved
0.6913	Remote Similarity	NPD3145	Approved
0.6903	Remote Similarity	NPD4162	Approved
0.6903	Remote Similarity	NPD3060	Approved
0.6899	Remote Similarity	NPD4739	Approved
0.6894	Remote Similarity	NPD7028	Phase 2
0.6892	Remote Similarity	NPD2614	Approved
0.689	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4420	Approved
0.6879	Remote Similarity	NPD7124	Phase 2
0.6875	Remote Similarity	NPD3687	Approved
0.6875	Remote Similarity	NPD3686	Approved
0.6871	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD196	Phase 1
0.6846	Remote Similarity	NPD5746	Approved
0.6839	Remote Similarity	NPD6618	Phase 2
0.6829	Remote Similarity	NPD5353	Approved
0.6829	Remote Similarity	NPD5967	Approved
0.6828	Remote Similarity	NPD2230	Approved
0.6828	Remote Similarity	NPD2233	Approved
0.6828	Remote Similarity	NPD2232	Approved
0.6818	Remote Similarity	NPD4476	Approved
0.6818	Remote Similarity	NPD4477	Approved
0.6818	Remote Similarity	NPD3349	Phase 2
0.6812	Remote Similarity	NPD228	Approved
0.6811	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5177	Phase 3
0.6795	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4584	Approved
0.6781	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5582	Discontinued
0.6772	Remote Similarity	NPD2120	Phase 2
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	NPD7018	Phase 2
0.6757	Remote Similarity	NPD7905	Discontinued
0.6755	Remote Similarity	NPD3532	Approved
0.6755	Remote Similarity	NPD5745	Approved
0.6755	Remote Similarity	NPD3530	Approved
0.6755	Remote Similarity	NPD3531	Approved
0.6753	Remote Similarity	NPD2164	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5754	Discontinued
0.6746	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5242	Approved
0.674	Remote Similarity	NPD5564	Approved
0.6739	Remote Similarity	NPD5006	Approved
0.6739	Remote Similarity	NPD5005	Approved
0.6735	Remote Similarity	NPD2922	Phase 1
0.6735	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.673	Remote Similarity	NPD4357	Discontinued
0.6723	Remote Similarity	NPD7291	Discontinued
0.6711	Remote Similarity	NPD9494	Approved
0.671	Remote Similarity	NPD1725	Approved
0.671	Remote Similarity	NPD6032	Approved
0.6709	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD5976	Discontinued
0.6708	Remote Similarity	NPD7427	Discontinued
0.669	Remote Similarity	NPD3596	Phase 2
0.6687	Remote Similarity	NPD4965	Approved
0.6687	Remote Similarity	NPD4966	Approved
0.6687	Remote Similarity	NPD4967	Phase 2
0.6686	Remote Similarity	NPD2968	Approved
0.6686	Remote Similarity	NPD2971	Approved
0.6667	Remote Similarity	NPD6382	Discontinued
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD3656	Approved
0.6667	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4622	Approved
0.6667	Remote Similarity	NPD4618	Approved
0.6649	Remote Similarity	NPD4859	Phase 1
0.6646	Remote Similarity	NPD6331	Phase 2
0.663	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6107	Approved
0.6627	Remote Similarity	NPD2563	Approved
0.6627	Remote Similarity	NPD2560	Approved
0.6626	Remote Similarity	NPD4017	Approved
0.6626	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD7153	Discontinued
0.6624	Remote Similarity	NPD2897	Discontinued
0.6624	Remote Similarity	NPD7037	Approved
0.6623	Remote Similarity	NPD5163	Phase 2
0.6608	Remote Similarity	NPD4481	Phase 3
0.6607	Remote Similarity	NPD6234	Discontinued
0.6606	Remote Similarity	NPD3384	Approved
0.6606	Remote Similarity	NPD3383	Approved
0.6606	Remote Similarity	NPD3382	Approved
0.6606	Remote Similarity	NPD37	Approved
0.6605	Remote Similarity	NPD4727	Phase 1
0.6605	Remote Similarity	NPD6030	Approved
0.6605	Remote Similarity	NPD2122	Discontinued
0.6605	Remote Similarity	NPD6031	Approved
0.6601	Remote Similarity	NPD3109	Approved
0.6601	Remote Similarity	NPD3110	Approved
0.6597	Remote Similarity	NPD2486	Discontinued
0.6593	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7608	Discontinued
0.6587	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD1424	Approved
0.6584	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7119	Phase 2
0.6581	Remote Similarity	NPD5689	Approved
0.6581	Remote Similarity	NPD5688	Approved
0.6579	Remote Similarity	NPD6812	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