NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	245.11
Volume:	249.216
LogP:	2.369
LogD:	3.102
LogS:	-3.935
# Rotatable Bonds:	3
TPSA:	38.77
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.748
Synthetic Accessibility Score:	2.053
Fsp3:	0.357
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.71
MDCK Permeability:	3.0128610887913965e-05
Pgp-inhibitor:	0.884
Pgp-substrate:	0.196
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.835
Plasma Protein Binding (PPB):	91.9425277709961%
Volume Distribution (VD):	0.528
Pgp-substrate:	6.97858190536499%

ADMET: Metabolism

CYP1A2-inhibitor:	0.988
CYP1A2-substrate:	0.473
CYP2C19-inhibitor:	0.804
CYP2C19-substrate:	0.179
CYP2C9-inhibitor:	0.205
CYP2C9-substrate:	0.873
CYP2D6-inhibitor:	0.845
CYP2D6-substrate:	0.695
CYP3A4-inhibitor:	0.879
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	12.977
Half-life (T1/2):	0.652

ADMET: Toxicity

hERG Blockers:	0.361
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.536
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.077
Skin Sensitization:	0.849
Carcinogencity:	0.896
Eye Corrosion:	0.118
Eye Irritation:	0.599
Respiratory Toxicity:	0.908

Download Data

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

Natural Product: NPC217574

Natural Product ID:	NPC217574
*Common Name:**	(E)-3-(1,3-Benzodioxol-5-Yl)-1-Pyrrolidin-1-Ylprop-2-En-1-One
IUPAC Name:	(E)-3-(1,3-benzodioxol-5-yl)-1-pyrrolidin-1-ylprop-2-en-1-one
Synonyms:
Standard InCHIKey:	SXFYVDPKNPGHKJ-GQCTYLIASA-N
Standard InCHI:	InChI=1S/C14H15NO3/c16-14(15-7-1-2-8-15)6-4-11-3-5-12-13(9-11)18-10-17-12/h3-6,9H,1-2,7-8,10H2/b6-4+
SMILES:	C1CCN(C1)C(=O)/C=C/c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2203920
PubChem CID:	694735
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
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S0040-4039(01)00209-X]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10575373]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15467205]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16808005]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23102654]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31103896]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	IC50	=	4890.0	nM	PMID[570940]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	IC50	>	100000.0	nM	PMID[570940]

☑ 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 NPC217574 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	229
0.1-0.2	1820
0.2-0.3	8478
0.3-0.4	10249
0.4-0.5	7341
0.5-0.6	11559
0.6-0.7	2682
0.7-0.8	295
0.8-0.85	12
0.85-0.9	4
0.9-0.95	16
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9841	High Similarity	NPC103947
0.9841	High Similarity	NPC45783
0.9841	High Similarity	NPC94280
0.9841	High Similarity	NPC159150
0.9841	High Similarity	NPC328419
0.9841	High Similarity	NPC193673
0.9764	High Similarity	NPC96406
0.9688	High Similarity	NPC145446
0.9688	High Similarity	NPC137172
0.9612	High Similarity	NPC95366
0.9612	High Similarity	NPC248505
0.938	High Similarity	NPC167096
0.9375	High Similarity	NPC318862
0.9308	High Similarity	NPC255817
0.9308	High Similarity	NPC136330
0.9308	High Similarity	NPC277042
0.9308	High Similarity	NPC205178
0.9308	High Similarity	NPC230698
0.9308	High Similarity	NPC251454
0.9308	High Similarity	NPC73883
0.9308	High Similarity	NPC196609
0.9237	High Similarity	NPC99078
0.9167	High Similarity	NPC220923
0.9167	High Similarity	NPC470707
0.9167	High Similarity	NPC252107
0.9023	High Similarity	NPC28641
0.9023	High Similarity	NPC194359
0.8947	High Similarity	NPC469808
0.8731	High Similarity	NPC180647
0.8633	High Similarity	NPC244338
0.8603	High Similarity	NPC225745
0.8288	Intermediate Similarity	NPC471073
0.8288	Intermediate Similarity	NPC270811
0.8268	Intermediate Similarity	NPC111225
0.8231	Intermediate Similarity	NPC470708
0.8203	Intermediate Similarity	NPC212643
0.8203	Intermediate Similarity	NPC199209
0.8176	Intermediate Similarity	NPC169742
0.8143	Intermediate Similarity	NPC231572
0.8095	Intermediate Similarity	NPC474852
0.8077	Intermediate Similarity	NPC69670
0.8077	Intermediate Similarity	NPC57501
0.8071	Intermediate Similarity	NPC113236
0.8071	Intermediate Similarity	NPC214036
0.8056	Intermediate Similarity	NPC469978
0.8027	Intermediate Similarity	NPC223125
0.8	Intermediate Similarity	NPC416184
0.8	Intermediate Similarity	NPC127326
0.7937	Intermediate Similarity	NPC31279
0.7919	Intermediate Similarity	NPC223124
0.7895	Intermediate Similarity	NPC114845
0.7883	Intermediate Similarity	NPC469977
0.7872	Intermediate Similarity	NPC7018
0.7868	Intermediate Similarity	NPC251466
0.7852	Intermediate Similarity	NPC300955
0.7838	Intermediate Similarity	NPC470088
0.7836	Intermediate Similarity	NPC256167
0.7806	Intermediate Similarity	NPC231198
0.7794	Intermediate Similarity	NPC71105
0.7794	Intermediate Similarity	NPC246133
0.7794	Intermediate Similarity	NPC170583
0.7794	Intermediate Similarity	NPC182147
0.7794	Intermediate Similarity	NPC207541
0.7794	Intermediate Similarity	NPC152186
0.7761	Intermediate Similarity	NPC193484
0.7737	Intermediate Similarity	NPC156944
0.773	Intermediate Similarity	NPC473463
0.7714	Intermediate Similarity	NPC118419
0.7698	Intermediate Similarity	NPC470706
0.7681	Intermediate Similarity	NPC99798
0.7681	Intermediate Similarity	NPC291449
0.7681	Intermediate Similarity	NPC157740
0.7681	Intermediate Similarity	NPC191302
0.7681	Intermediate Similarity	NPC41331
0.7656	Intermediate Similarity	NPC179309
0.7626	Intermediate Similarity	NPC147247
0.7626	Intermediate Similarity	NPC246974
0.7609	Intermediate Similarity	NPC218323
0.7606	Intermediate Similarity	NPC284855
0.7606	Intermediate Similarity	NPC282477
0.7557	Intermediate Similarity	NPC294941
0.7554	Intermediate Similarity	NPC64948
0.7554	Intermediate Similarity	NPC172403
0.7554	Intermediate Similarity	NPC286683
0.7552	Intermediate Similarity	NPC11147
0.7548	Intermediate Similarity	NPC106786
0.7536	Intermediate Similarity	NPC120066
0.7536	Intermediate Similarity	NPC85830
0.7519	Intermediate Similarity	NPC33271
0.75	Intermediate Similarity	NPC80241
0.75	Intermediate Similarity	NPC301641
0.7468	Intermediate Similarity	NPC76079
0.7468	Intermediate Similarity	NPC78733
0.7448	Intermediate Similarity	NPC193528
0.7445	Intermediate Similarity	NPC298486
0.744	Intermediate Similarity	NPC310905
0.744	Intermediate Similarity	NPC12714
0.7417	Intermediate Similarity	NPC475959
0.7407	Intermediate Similarity	NPC119949
0.7405	Intermediate Similarity	NPC59567
0.7388	Intermediate Similarity	NPC120075
0.7386	Intermediate Similarity	NPC119669
0.7368	Intermediate Similarity	NPC469539
0.7368	Intermediate Similarity	NPC469540
0.7353	Intermediate Similarity	NPC344161
0.7338	Intermediate Similarity	NPC148898
0.7338	Intermediate Similarity	NPC210148
0.7338	Intermediate Similarity	NPC233029
0.7333	Intermediate Similarity	NPC164706
0.7333	Intermediate Similarity	NPC70744
0.7333	Intermediate Similarity	NPC124916
0.7333	Intermediate Similarity	NPC272471
0.7333	Intermediate Similarity	NPC137537
0.7333	Intermediate Similarity	NPC107588
0.7333	Intermediate Similarity	NPC277460
0.7333	Intermediate Similarity	NPC145304
0.7329	Intermediate Similarity	NPC86469
0.7329	Intermediate Similarity	NPC241055
0.7329	Intermediate Similarity	NPC230968
0.7329	Intermediate Similarity	NPC102260
0.7329	Intermediate Similarity	NPC254610
0.7328	Intermediate Similarity	NPC245552
0.7324	Intermediate Similarity	NPC476748
0.7324	Intermediate Similarity	NPC160193
0.7323	Intermediate Similarity	NPC292792
0.7321	Intermediate Similarity	NPC471650
0.7313	Intermediate Similarity	NPC268317
0.731	Intermediate Similarity	NPC475828
0.7308	Intermediate Similarity	NPC31311
0.7308	Intermediate Similarity	NPC234392
0.7305	Intermediate Similarity	NPC83511
0.7303	Intermediate Similarity	NPC37144
0.7303	Intermediate Similarity	NPC59907
0.7292	Intermediate Similarity	NPC266425
0.7279	Intermediate Similarity	NPC166184
0.7279	Intermediate Similarity	NPC37858
0.7278	Intermediate Similarity	NPC97072
0.7278	Intermediate Similarity	NPC215829
0.7273	Intermediate Similarity	NPC477705
0.7273	Intermediate Similarity	NPC477694
0.7259	Intermediate Similarity	NPC280001
0.7259	Intermediate Similarity	NPC39793
0.7259	Intermediate Similarity	NPC185738
0.7256	Intermediate Similarity	NPC308267
0.725	Intermediate Similarity	NPC168409
0.725	Intermediate Similarity	NPC306669
0.7248	Intermediate Similarity	NPC138438
0.7248	Intermediate Similarity	NPC908
0.7246	Intermediate Similarity	NPC102760
0.7234	Intermediate Similarity	NPC213711
0.7234	Intermediate Similarity	NPC40352
0.723	Intermediate Similarity	NPC178290
0.7226	Intermediate Similarity	NPC202474
0.7226	Intermediate Similarity	NPC222175
0.7222	Intermediate Similarity	NPC477706
0.7218	Intermediate Similarity	NPC303522
0.7183	Intermediate Similarity	NPC158737
0.7183	Intermediate Similarity	NPC177167
0.7181	Intermediate Similarity	NPC278076
0.7181	Intermediate Similarity	NPC275150
0.7174	Intermediate Similarity	NPC471877
0.7174	Intermediate Similarity	NPC204466
0.717	Intermediate Similarity	NPC165797
0.716	Intermediate Similarity	NPC474324
0.716	Intermediate Similarity	NPC57812
0.7154	Intermediate Similarity	NPC258171
0.7154	Intermediate Similarity	NPC227894
0.7152	Intermediate Similarity	NPC181905
0.7152	Intermediate Similarity	NPC287152
0.7143	Intermediate Similarity	NPC249788
0.7143	Intermediate Similarity	NPC247972
0.7143	Intermediate Similarity	NPC307682
0.7143	Intermediate Similarity	NPC211296
0.7134	Intermediate Similarity	NPC216459
0.7134	Intermediate Similarity	NPC41178
0.7134	Intermediate Similarity	NPC67978
0.7134	Intermediate Similarity	NPC303581
0.7134	Intermediate Similarity	NPC93593
0.7134	Intermediate Similarity	NPC138487
0.7133	Intermediate Similarity	NPC158471
0.7133	Intermediate Similarity	NPC165128
0.7133	Intermediate Similarity	NPC57119
0.7133	Intermediate Similarity	NPC226862
0.7123	Intermediate Similarity	NPC205915
0.7122	Intermediate Similarity	NPC70752
0.7122	Intermediate Similarity	NPC310373
0.7117	Intermediate Similarity	NPC475845
0.7114	Intermediate Similarity	NPC77572
0.7114	Intermediate Similarity	NPC318575
0.7107	Intermediate Similarity	NPC329640
0.7107	Intermediate Similarity	NPC477080
0.7101	Intermediate Similarity	NPC116007
0.7101	Intermediate Similarity	NPC2058
0.7092	Intermediate Similarity	NPC283170
0.7092	Intermediate Similarity	NPC191768
0.7092	Intermediate Similarity	NPC92869
0.7089	Intermediate Similarity	NPC146288
0.7081	Intermediate Similarity	NPC218614
0.7081	Intermediate Similarity	NPC320104
0.7075	Intermediate Similarity	NPC45404

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 NPC217574 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	742
0.2-0.3	1234
0.3-0.4	2529
0.4-0.5	2636
0.5-0.6	1398
0.6-0.7	400
0.7-0.8	39
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9308	High Similarity	NPD2492	Phase 1
0.8125	Intermediate Similarity	NPD5297	Approved
0.7862	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD824	Approved
0.75	Intermediate Similarity	NPD743	Approved
0.7451	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4210	Discontinued
0.7407	Intermediate Similarity	NPD1357	Approved
0.7376	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7280	Phase 3
0.7289	Intermediate Similarity	NPD7281	Phase 3
0.7273	Intermediate Similarity	NPD5718	Phase 2
0.7259	Intermediate Similarity	NPD5536	Phase 2
0.7226	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3885	Approved
0.7143	Intermediate Similarity	NPD1420	Approved
0.7143	Intermediate Similarity	NPD1421	Approved
0.7143	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4236	Phase 3
0.7133	Intermediate Similarity	NPD4237	Approved
0.7124	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3146	Approved
0.7122	Intermediate Similarity	NPD3705	Approved
0.7075	Intermediate Similarity	NPD2653	Approved
0.7063	Intermediate Similarity	NPD2040	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2219	Phase 1
0.7032	Intermediate Similarity	NPD1670	Discontinued
0.7027	Intermediate Similarity	NPD6895	Approved
0.7027	Intermediate Similarity	NPD6896	Approved
0.7023	Intermediate Similarity	NPD1358	Approved
0.698	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6873	Phase 2
0.6962	Remote Similarity	NPD6386	Approved
0.6962	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6385	Approved
0.6962	Remote Similarity	NPD7110	Phase 1
0.6957	Remote Similarity	NPD5604	Discontinued
0.6954	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4357	Discontinued
0.694	Remote Similarity	NPD228	Approved
0.6937	Remote Similarity	NPD5978	Approved
0.6937	Remote Similarity	NPD5977	Approved
0.6918	Remote Similarity	NPD3144	Approved
0.6918	Remote Similarity	NPD3145	Approved
0.6913	Remote Similarity	NPD6111	Discontinued
0.6901	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6876	Approved
0.6899	Remote Similarity	NPD6875	Approved
0.689	Remote Similarity	NPD4166	Phase 2
0.6887	Remote Similarity	NPD1375	Discontinued
0.6875	Remote Similarity	NPD2977	Approved
0.6875	Remote Similarity	NPD2978	Approved
0.6871	Remote Similarity	NPD2245	Discovery
0.6871	Remote Similarity	NPD2674	Phase 3
0.6863	Remote Similarity	NPD5481	Discontinued
0.6838	Remote Similarity	NPD5283	Phase 1
0.6818	Remote Similarity	NPD3134	Approved
0.6813	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD776	Approved
0.6743	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD2668	Approved
0.6738	Remote Similarity	NPD2667	Approved
0.6736	Remote Similarity	NPD2922	Phase 1
0.6733	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD3349	Phase 2
0.6722	Remote Similarity	NPD5457	Discontinued
0.6712	Remote Similarity	NPD9494	Approved
0.6711	Remote Similarity	NPD3142	Approved
0.6711	Remote Similarity	NPD2161	Phase 2
0.6711	Remote Similarity	NPD3140	Approved
0.671	Remote Similarity	NPD5241	Discontinued
0.6709	Remote Similarity	NPD3641	Approved
0.6709	Remote Similarity	NPD3640	Phase 3
0.6709	Remote Similarity	NPD3639	Approved
0.6688	Remote Similarity	NPD4584	Approved
0.6688	Remote Similarity	NPD1424	Approved
0.6688	Remote Similarity	NPD4739	Approved
0.6688	Remote Similarity	NPD3060	Approved
0.6688	Remote Similarity	NPD4162	Approved
0.6685	Remote Similarity	NPD5582	Discontinued
0.6667	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3656	Approved
0.6667	Remote Similarity	NPD2120	Phase 2
0.6667	Remote Similarity	NPD7124	Phase 2
0.6645	Remote Similarity	NPD2164	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7018	Phase 2
0.6626	Remote Similarity	NPD5353	Approved
0.6622	Remote Similarity	NPD5746	Approved
0.6607	Remote Similarity	NPD2898	Approved
0.6605	Remote Similarity	NPD7248	Discontinued
0.6604	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5976	Discontinued
0.6603	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD1725	Approved
0.6597	Remote Similarity	NPD2233	Approved
0.6597	Remote Similarity	NPD2232	Approved
0.6597	Remote Similarity	NPD2230	Approved
0.6582	Remote Similarity	NPD2335	Discontinued
0.6581	Remote Similarity	NPD5177	Phase 3
0.6577	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD155	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD3596	Phase 2
0.6564	Remote Similarity	NPD4585	Approved
0.6564	Remote Similarity	NPD5772	Approved
0.6564	Remote Similarity	NPD5773	Approved
0.6562	Remote Similarity	NPD3687	Approved
0.6562	Remote Similarity	NPD3686	Approved
0.6561	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD4207	Discontinued
0.6552	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6618	Phase 2
0.6549	Remote Similarity	NPD6382	Discontinued
0.6549	Remote Similarity	NPD2594	Approved
0.6549	Remote Similarity	NPD2595	Approved
0.6541	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5754	Discontinued
0.6536	Remote Similarity	NPD6493	Phase 3
0.6533	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD3531	Approved
0.6533	Remote Similarity	NPD5745	Approved
0.6533	Remote Similarity	NPD3532	Approved
0.6533	Remote Similarity	NPD3530	Approved
0.6531	Remote Similarity	NPD7905	Discontinued
0.6524	Remote Similarity	NPD2563	Approved
0.6524	Remote Similarity	NPD2560	Approved
0.6522	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4017	Approved
0.6519	Remote Similarity	NPD4420	Approved
0.6517	Remote Similarity	NPD7296	Approved
0.6516	Remote Similarity	NPD7037	Approved
0.6516	Remote Similarity	NPD7153	Discontinued
0.6512	Remote Similarity	NPD6297	Approved
0.651	Remote Similarity	NPD5163	Phase 2
0.6509	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6031	Approved
0.65	Remote Similarity	NPD709	Approved
0.65	Remote Similarity	NPD6030	Approved
0.65	Remote Similarity	NPD2122	Discontinued
0.6491	Remote Similarity	NPD5312	Approved
0.6491	Remote Similarity	NPD5313	Approved
0.6485	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7028	Phase 2
0.6479	Remote Similarity	NPD1182	Approved
0.6478	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD4123	Phase 3
0.6474	Remote Similarity	NPD2654	Approved
0.6471	Remote Similarity	NPD7119	Phase 2
0.6467	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1039	Discontinued
0.6467	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD5677	Discontinued
0.6467	Remote Similarity	NPD1336	Approved
0.6464	Remote Similarity	NPD5564	Approved
0.6463	Remote Similarity	NPD1819	Approved
0.6463	Remote Similarity	NPD1820	Approved
0.6463	Remote Similarity	NPD1818	Approved
0.6463	Remote Similarity	NPD1817	Approved
0.646	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD3447	Discontinued
0.6456	Remote Similarity	NPD5295	Discontinued
0.6456	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.645	Remote Similarity	NPD5242	Approved
0.6442	Remote Similarity	NPD5089	Approved
0.6442	Remote Similarity	NPD5090	Approved
0.6441	Remote Similarity	NPD7291	Discontinued
0.6441	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD1669	Approved
0.6438	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD5691	Approved
0.6433	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6331	Phase 2
0.6429	Remote Similarity	NPD593	Approved
0.6429	Remote Similarity	NPD4108	Discontinued
0.6429	Remote Similarity	NPD595	Approved
0.642	Remote Similarity	NPD746	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6584	Phase 3
0.6412	Remote Similarity	NPD4481	Phase 3
0.6404	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD3384	Approved
0.6402	Remote Similarity	NPD3383	Approved
0.6402	Remote Similarity	NPD3382	Approved
0.6398	Remote Similarity	NPD4727	Phase 1
0.6389	Remote Similarity	NPD4626	Approved
0.6387	Remote Similarity	NPD6032	Approved
0.6384	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4859	Phase 1
0.6382	Remote Similarity	NPD3110	Approved
0.6382	Remote Similarity	NPD3109	Approved
0.6378	Remote Similarity	NPD5005	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