NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	273.14
Volume:	283.808
LogP:	3.384
LogD:	3.527
LogS:	-5.103
# Rotatable Bonds:	4
TPSA:	47.56
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.861
Synthetic Accessibility Score:	2.097
Fsp3:	0.438
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.767
MDCK Permeability:	3.129866672679782e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.399
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.97
Plasma Protein Binding (PPB):	95.72924041748047%
Volume Distribution (VD):	0.653
Pgp-substrate:	4.138206958770752%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.16
CYP2C19-inhibitor:	0.898
CYP2C19-substrate:	0.157
CYP2C9-inhibitor:	0.628
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.829
CYP2D6-substrate:	0.72
CYP3A4-inhibitor:	0.924
CYP3A4-substrate:	0.159

ADMET: Excretion

Clearance (CL):	11.869
Half-life (T1/2):	0.274

ADMET: Toxicity

hERG Blockers:	0.326
Human Hepatotoxicity (H-HT):	0.23
Drug-inuced Liver Injury (DILI):	0.42
AMES Toxicity:	0.126
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.187
Skin Sensitization:	0.86
Carcinogencity:	0.83
Eye Corrosion:	0.011
Eye Irritation:	0.211
Respiratory Toxicity:	0.847

Download Data

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

Natural Product: NPC470706

Natural Product ID:	NPC470706
*Common Name:**	3-(Benzo[D][1,3]Dioxol-5-Yl)-N-Cyclohexylacrylamide
IUPAC Name:	(E)-3-(1,3-benzodioxol-5-yl)-N-cyclohexylprop-2-enamide
Synonyms:
Standard InCHIKey:	HEVXIAMRBRLSEJ-VQHVLOKHSA-N
Standard InCHI:	InChI=1S/C16H19NO3/c18-16(17-13-4-2-1-3-5-13)9-7-12-6-8-14-15(10-12)20-11-19-14/h6-10,13H,1-5,11H2,(H,17,18)/b9-7+
SMILES:	OC(=NC1CCCCC1)/C=C/c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2203918
PubChem CID:	692702
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		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.	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	=	666.0	nM	PMID[523151]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	IC50	>	100000.0	nM	PMID[523151]

☑ 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 NPC470706 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	205
0.1-0.2	1432
0.2-0.3	8377
0.3-0.4	10335
0.4-0.5	6627
0.5-0.6	11025
0.6-0.7	4054
0.7-0.8	588
0.8-0.85	31
0.85-0.9	8
0.9-0.95	14
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9597	High Similarity	NPC469977
0.9435	High Similarity	NPC251466
0.9355	High Similarity	NPC246133
0.9355	High Similarity	NPC170583
0.9355	High Similarity	NPC152186
0.9355	High Similarity	NPC207541
0.9355	High Similarity	NPC71105
0.9355	High Similarity	NPC182147
0.928	High Similarity	NPC156944
0.9274	High Similarity	NPC300955
0.9206	High Similarity	NPC157740
0.9206	High Similarity	NPC41331
0.9206	High Similarity	NPC291449
0.9206	High Similarity	NPC99798
0.9134	High Similarity	NPC246974
0.9134	High Similarity	NPC147247
0.8931	High Similarity	NPC473463
0.8906	High Similarity	NPC191302
0.8872	High Similarity	NPC254610
0.8828	High Similarity	NPC301713
0.8788	High Similarity	NPC282477
0.8788	High Similarity	NPC284855
0.8692	High Similarity	NPC155838
0.8626	High Similarity	NPC195749
0.8626	High Similarity	NPC52029
0.8626	High Similarity	NPC35961
0.8615	High Similarity	NPC186898
0.8496	Intermediate Similarity	NPC214869
0.8473	Intermediate Similarity	NPC251571
0.8473	Intermediate Similarity	NPC153990
0.8421	Intermediate Similarity	NPC114102
0.8333	Intermediate Similarity	NPC77572
0.8273	Intermediate Similarity	NPC275150
0.8188	Intermediate Similarity	NPC41473
0.8188	Intermediate Similarity	NPC312770
0.8188	Intermediate Similarity	NPC14600
0.8188	Intermediate Similarity	NPC204848
0.8188	Intermediate Similarity	NPC160607
0.8168	Intermediate Similarity	NPC249788
0.8148	Intermediate Similarity	NPC255550
0.8148	Intermediate Similarity	NPC308885
0.813	Intermediate Similarity	NPC127326
0.8129	Intermediate Similarity	NPC299583
0.8129	Intermediate Similarity	NPC296898
0.8088	Intermediate Similarity	NPC130595
0.8088	Intermediate Similarity	NPC93882
0.8065	Intermediate Similarity	NPC31279
0.8058	Intermediate Similarity	NPC193528
0.8043	Intermediate Similarity	NPC277042
0.8043	Intermediate Similarity	NPC205178
0.8043	Intermediate Similarity	NPC136330
0.8043	Intermediate Similarity	NPC255817
0.8043	Intermediate Similarity	NPC251454
0.8043	Intermediate Similarity	NPC196609
0.8043	Intermediate Similarity	NPC230698
0.8043	Intermediate Similarity	NPC180647
0.8043	Intermediate Similarity	NPC73883
0.8042	Intermediate Similarity	NPC327623
0.8031	Intermediate Similarity	NPC303370
0.8029	Intermediate Similarity	NPC6854
0.8029	Intermediate Similarity	NPC285078
0.8029	Intermediate Similarity	NPC313737
0.8	Intermediate Similarity	NPC263835
0.8	Intermediate Similarity	NPC344161
0.8	Intermediate Similarity	NPC166837
0.7986	Intermediate Similarity	NPC99078
0.7985	Intermediate Similarity	NPC274356
0.7971	Intermediate Similarity	NPC167096
0.7971	Intermediate Similarity	NPC218530
0.7959	Intermediate Similarity	NPC474560
0.7956	Intermediate Similarity	NPC118419
0.7956	Intermediate Similarity	NPC318862
0.7943	Intermediate Similarity	NPC477838
0.7943	Intermediate Similarity	NPC477837
0.7929	Intermediate Similarity	NPC470707
0.7929	Intermediate Similarity	NPC225745
0.7929	Intermediate Similarity	NPC252107
0.7929	Intermediate Similarity	NPC220923
0.7923	Intermediate Similarity	NPC57501
0.7923	Intermediate Similarity	NPC43275
0.7907	Intermediate Similarity	NPC283468
0.7879	Intermediate Similarity	NPC80241
0.7879	Intermediate Similarity	NPC301641
0.7857	Intermediate Similarity	NPC198741
0.7852	Intermediate Similarity	NPC213711
0.7852	Intermediate Similarity	NPC40352
0.7846	Intermediate Similarity	NPC122009
0.7842	Intermediate Similarity	NPC103947
0.7842	Intermediate Similarity	NPC94280
0.7842	Intermediate Similarity	NPC159150
0.7842	Intermediate Similarity	NPC193673
0.7842	Intermediate Similarity	NPC45783
0.7842	Intermediate Similarity	NPC328419
0.7832	Intermediate Similarity	NPC100478
0.7832	Intermediate Similarity	NPC222039
0.781	Intermediate Similarity	NPC228769
0.781	Intermediate Similarity	NPC470633
0.7803	Intermediate Similarity	NPC83279
0.7801	Intermediate Similarity	NPC28641
0.7801	Intermediate Similarity	NPC194359
0.7793	Intermediate Similarity	NPC5462
0.7786	Intermediate Similarity	NPC11147
0.7786	Intermediate Similarity	NPC96406
0.7786	Intermediate Similarity	NPC256369
0.7786	Intermediate Similarity	NPC69670
0.7761	Intermediate Similarity	NPC211218
0.7755	Intermediate Similarity	NPC475959
0.7754	Intermediate Similarity	NPC275950
0.7754	Intermediate Similarity	NPC63574
0.7754	Intermediate Similarity	NPC184814
0.773	Intermediate Similarity	NPC416184
0.773	Intermediate Similarity	NPC145446
0.773	Intermediate Similarity	NPC137172
0.7704	Intermediate Similarity	NPC95733
0.7704	Intermediate Similarity	NPC62101
0.7703	Intermediate Similarity	NPC182119
0.7698	Intermediate Similarity	NPC217574
0.7698	Intermediate Similarity	NPC476345
0.7692	Intermediate Similarity	NPC111225
0.7687	Intermediate Similarity	NPC471314
0.7687	Intermediate Similarity	NPC256167
0.7687	Intermediate Similarity	NPC471315
0.768	Intermediate Similarity	NPC227894
0.7676	Intermediate Similarity	NPC95366
0.7676	Intermediate Similarity	NPC248505
0.7671	Intermediate Similarity	NPC145304
0.7669	Intermediate Similarity	NPC183262
0.7664	Intermediate Similarity	NPC172403
0.7656	Intermediate Similarity	NPC165646
0.7655	Intermediate Similarity	NPC178466
0.7655	Intermediate Similarity	NPC63628
0.7652	Intermediate Similarity	NPC268572
0.7647	Intermediate Similarity	NPC17348
0.7647	Intermediate Similarity	NPC69360
0.7643	Intermediate Similarity	NPC106739
0.7643	Intermediate Similarity	NPC104077
0.7643	Intermediate Similarity	NPC147616
0.7643	Intermediate Similarity	NPC259742
0.7643	Intermediate Similarity	NPC227002
0.7643	Intermediate Similarity	NPC471505
0.7643	Intermediate Similarity	NPC97316
0.7643	Intermediate Similarity	NPC219671
0.7635	Intermediate Similarity	NPC471032
0.7635	Intermediate Similarity	NPC153644
0.7635	Intermediate Similarity	NPC470935
0.7634	Intermediate Similarity	NPC212643
0.7634	Intermediate Similarity	NPC199209
0.7634	Intermediate Similarity	NPC120075
0.7634	Intermediate Similarity	NPC33271
0.7634	Intermediate Similarity	NPC280001
0.763	Intermediate Similarity	NPC13020
0.763	Intermediate Similarity	NPC140359
0.7626	Intermediate Similarity	NPC173308
0.7626	Intermediate Similarity	NPC134764
0.7626	Intermediate Similarity	NPC181079
0.7626	Intermediate Similarity	NPC171550
0.7612	Intermediate Similarity	NPC114845
0.7606	Intermediate Similarity	NPC7018
0.7594	Intermediate Similarity	NPC471308
0.7594	Intermediate Similarity	NPC289330
0.7594	Intermediate Similarity	NPC17388
0.7594	Intermediate Similarity	NPC53596
0.7594	Intermediate Similarity	NPC160120
0.7589	Intermediate Similarity	NPC169973
0.7589	Intermediate Similarity	NPC471391
0.7589	Intermediate Similarity	NPC471390
0.7589	Intermediate Similarity	NPC112237
0.7578	Intermediate Similarity	NPC55300
0.7576	Intermediate Similarity	NPC470626
0.7568	Intermediate Similarity	NPC115144
0.7568	Intermediate Similarity	NPC277857
0.7568	Intermediate Similarity	NPC16436
0.7564	Intermediate Similarity	NPC54125
0.7564	Intermediate Similarity	NPC89199
0.7561	Intermediate Similarity	NPC310905
0.7561	Intermediate Similarity	NPC12714
0.7559	Intermediate Similarity	NPC7097
0.7559	Intermediate Similarity	NPC36108
0.7559	Intermediate Similarity	NPC246358
0.7559	Intermediate Similarity	NPC233731
0.7557	Intermediate Similarity	NPC258992
0.7556	Intermediate Similarity	NPC298486
0.755	Intermediate Similarity	NPC270811
0.755	Intermediate Similarity	NPC471073
0.7536	Intermediate Similarity	NPC177167
0.7536	Intermediate Similarity	NPC100129
0.7536	Intermediate Similarity	NPC158737
0.7533	Intermediate Similarity	NPC478189
0.7532	Intermediate Similarity	NPC111485
0.7519	Intermediate Similarity	NPC119949
0.7519	Intermediate Similarity	NPC281298
0.7519	Intermediate Similarity	NPC310338
0.7518	Intermediate Similarity	NPC252833
0.7518	Intermediate Similarity	NPC29477
0.75	Intermediate Similarity	NPC31344
0.75	Intermediate Similarity	NPC476570
0.75	Intermediate Similarity	NPC228040
0.75	Intermediate Similarity	NPC189782
0.75	Intermediate Similarity	NPC293619
0.75	Intermediate Similarity	NPC477694

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 NPC470706 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	653
0.2-0.3	1213
0.3-0.4	2285
0.4-0.5	2639
0.5-0.6	1502
0.6-0.7	622
0.7-0.8	80
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8148	Intermediate Similarity	NPD3145	Approved
0.8148	Intermediate Similarity	NPD3144	Approved
0.8088	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD2674	Phase 3
0.8062	Intermediate Similarity	NPD1357	Approved
0.8043	Intermediate Similarity	NPD2492	Phase 1
0.7931	Intermediate Similarity	NPD4739	Approved
0.7867	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD2922	Phase 1
0.7829	Intermediate Similarity	NPD5604	Discontinued
0.78	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6331	Phase 2
0.7761	Intermediate Similarity	NPD1669	Approved
0.7748	Intermediate Similarity	NPD2977	Approved
0.7748	Intermediate Similarity	NPD2978	Approved
0.7746	Intermediate Similarity	NPD2161	Phase 2
0.7724	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4237	Approved
0.7708	Intermediate Similarity	NPD4236	Phase 3
0.7692	Intermediate Similarity	NPD1375	Discontinued
0.7676	Intermediate Similarity	NPD4108	Discontinued
0.7671	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD2122	Discontinued
0.7571	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD4123	Phase 3
0.7554	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD7153	Discontinued
0.7516	Intermediate Similarity	NPD5773	Approved
0.7516	Intermediate Similarity	NPD5772	Approved
0.75	Intermediate Similarity	NPD5111	Phase 2
0.75	Intermediate Similarity	NPD5109	Approved
0.75	Intermediate Similarity	NPD5718	Phase 2
0.75	Intermediate Similarity	NPD5110	Phase 2
0.7484	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5241	Discontinued
0.7481	Intermediate Similarity	NPD3705	Approved
0.7462	Intermediate Similarity	NPD5283	Phase 1
0.7442	Intermediate Similarity	NPD228	Approved
0.7429	Intermediate Similarity	NPD1024	Discontinued
0.74	Intermediate Similarity	NPD7526	Approved
0.74	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD52	Approved
0.74	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4357	Discontinued
0.7368	Intermediate Similarity	NPD4005	Discontinued
0.7353	Intermediate Similarity	NPD776	Approved
0.7348	Intermediate Similarity	NPD709	Approved
0.7347	Intermediate Similarity	NPD3060	Approved
0.7333	Intermediate Similarity	NPD2667	Approved
0.7333	Intermediate Similarity	NPD2668	Approved
0.732	Intermediate Similarity	NPD4675	Approved
0.732	Intermediate Similarity	NPD4678	Approved
0.7305	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD2230	Approved
0.7299	Intermediate Similarity	NPD2232	Approved
0.7299	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD2233	Approved
0.7292	Intermediate Similarity	NPD2157	Approved
0.7286	Intermediate Similarity	NPD4993	Discontinued
0.7286	Intermediate Similarity	NPD1712	Approved
0.7279	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6895	Approved
0.7241	Intermediate Similarity	NPD6896	Approved
0.7239	Intermediate Similarity	NPD5536	Phase 2
0.723	Intermediate Similarity	NPD4162	Approved
0.7219	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2231	Phase 2
0.7174	Intermediate Similarity	NPD2235	Phase 2
0.7172	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD2040	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1558	Phase 1
0.7152	Intermediate Similarity	NPD4055	Discovery
0.7133	Intermediate Similarity	NPD2219	Phase 1
0.7122	Intermediate Similarity	NPD3685	Discontinued
0.7114	Intermediate Similarity	NPD5177	Phase 3
0.7095	Intermediate Similarity	NPD3656	Approved
0.7092	Intermediate Similarity	NPD6584	Phase 3
0.7083	Intermediate Similarity	NPD7477	Discontinued
0.7063	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2653	Approved
0.7051	Intermediate Similarity	NPD5089	Approved
0.7051	Intermediate Similarity	NPD5090	Approved
0.7047	Intermediate Similarity	NPD2808	Discontinued
0.7047	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4083	Discontinued
0.7034	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3055	Approved
0.7021	Intermediate Similarity	NPD3053	Approved
0.7019	Intermediate Similarity	NPD2821	Approved
0.7	Intermediate Similarity	NPD2983	Phase 2
0.7	Intermediate Similarity	NPD2982	Phase 2
0.6993	Remote Similarity	NPD4584	Approved
0.6992	Remote Similarity	NPD821	Approved
0.6975	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD839	Approved
0.6966	Remote Similarity	NPD840	Approved
0.6962	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2644	Approved
0.6951	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3027	Phase 3
0.6939	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1182	Approved
0.6933	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2981	Phase 2
0.6923	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2238	Phase 2
0.6908	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3692	Discontinued
0.6897	Remote Similarity	NPD1039	Discontinued
0.6892	Remote Similarity	NPD6111	Discontinued
0.6886	Remote Similarity	NPD7007	Discovery
0.6883	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6583	Phase 3
0.6879	Remote Similarity	NPD6582	Phase 2
0.6866	Remote Similarity	NPD9379	Approved
0.6866	Remote Similarity	NPD9377	Approved
0.6864	Remote Similarity	NPD7281	Phase 3
0.6864	Remote Similarity	NPD7280	Phase 3
0.6863	Remote Similarity	NPD7124	Phase 2
0.6859	Remote Similarity	NPD3686	Approved
0.6859	Remote Similarity	NPD2883	Discontinued
0.6859	Remote Similarity	NPD3687	Approved
0.6849	Remote Similarity	NPD1423	Approved
0.6849	Remote Similarity	NPD3530	Approved
0.6849	Remote Similarity	NPD3532	Approved
0.6849	Remote Similarity	NPD3531	Approved
0.6846	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4110	Phase 3
0.6842	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6385	Approved
0.6835	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6386	Approved
0.6831	Remote Similarity	NPD5311	Approved
0.6831	Remote Similarity	NPD5310	Approved
0.6829	Remote Similarity	NPD2970	Approved
0.6829	Remote Similarity	NPD2969	Approved
0.6824	Remote Similarity	NPD3052	Approved
0.6824	Remote Similarity	NPD3054	Approved
0.6824	Remote Similarity	NPD4097	Suspended
0.6821	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7037	Approved
0.6818	Remote Similarity	NPD5297	Approved
0.6818	Remote Similarity	NPD2684	Approved
0.6815	Remote Similarity	NPD3111	Phase 1
0.6815	Remote Similarity	NPD4017	Approved
0.6813	Remote Similarity	NPD2563	Approved
0.6813	Remote Similarity	NPD2560	Approved
0.6806	Remote Similarity	NPD3018	Phase 2
0.6803	Remote Similarity	NPD3110	Approved
0.6803	Remote Similarity	NPD3620	Phase 2
0.6803	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD3109	Approved
0.6802	Remote Similarity	NPD3349	Phase 2
0.68	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6030	Approved
0.6795	Remote Similarity	NPD4727	Phase 1
0.6795	Remote Similarity	NPD6031	Approved
0.6788	Remote Similarity	NPD3596	Phase 2
0.6788	Remote Similarity	NPD2489	Approved
0.6788	Remote Similarity	NPD27	Approved
0.6783	Remote Similarity	NPD1818	Approved
0.6783	Remote Similarity	NPD1820	Approved
0.6783	Remote Similarity	NPD1817	Approved
0.6783	Remote Similarity	NPD1819	Approved
0.6781	Remote Similarity	NPD1048	Approved
0.6781	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2458	Approved
0.6776	Remote Similarity	NPD2460	Phase 3
0.6776	Remote Similarity	NPD2459	Approved
0.6774	Remote Similarity	NPD2505	Approved
0.6774	Remote Similarity	NPD2874	Phase 2
0.6774	Remote Similarity	NPD2504	Approved
0.6772	Remote Similarity	NPD3296	Phase 1
0.6768	Remote Similarity	NPD3051	Approved
0.6765	Remote Similarity	NPD593	Approved
0.6765	Remote Similarity	NPD595	Approved
0.6763	Remote Similarity	NPD6382	Discontinued
0.6761	Remote Similarity	NPD4129	Approved
0.6761	Remote Similarity	NPD1420	Approved
0.6761	Remote Similarity	NPD1421	Approved
0.6759	Remote Similarity	NPD600	Approved
0.6759	Remote Similarity	NPD596	Approved
0.6759	Remote Similarity	NPD2614	Approved
0.6752	Remote Similarity	NPD4210	Discontinued
0.6744	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD558	Phase 2
0.6736	Remote Similarity	NPD7905	Discontinued
0.6735	Remote Similarity	NPD5745	Approved
0.6735	Remote Similarity	NPD3058	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