NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	259.12
Volume:	266.512
LogP:	2.95
LogD:	3.294
LogS:	-4.794
# 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:	0.848
Synthetic Accessibility Score:	2.094
Fsp3:	0.4
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:	-4.751
MDCK Permeability:	2.9613933293148875e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.485
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.973
Plasma Protein Binding (PPB):	94.89385986328125%
Volume Distribution (VD):	0.61
Pgp-substrate:	5.708580493927002%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.156
CYP2C19-inhibitor:	0.872
CYP2C19-substrate:	0.151
CYP2C9-inhibitor:	0.525
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.817
CYP2D6-substrate:	0.715
CYP3A4-inhibitor:	0.915
CYP3A4-substrate:	0.164

ADMET: Excretion

Clearance (CL):	12.375
Half-life (T1/2):	0.353

ADMET: Toxicity

hERG Blockers:	0.238
Human Hepatotoxicity (H-HT):	0.231
Drug-inuced Liver Injury (DILI):	0.369
AMES Toxicity:	0.174
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.2
Skin Sensitization:	0.821
Carcinogencity:	0.865
Eye Corrosion:	0.011
Eye Irritation:	0.214
Respiratory Toxicity:	0.78

Download Data

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

Natural Product: NPC469977

Natural Product ID:	NPC469977
*Common Name:**	Sid47200685
IUPAC Name:	(E)-3-(1,3-benzodioxol-5-yl)-N-cyclopentylprop-2-enamide
Synonyms:
Standard InCHIKey:	SLFOTQIGIXJPPD-SOFGYWHQSA-N
Standard InCHI:	InChI=1S/C15H17NO3/c17-15(16-12-3-1-2-4-12)8-6-11-5-7-13-14(9-11)19-10-18-13/h5-9,12H,1-4,10H2,(H,16,17)/b8-6+
SMILES:	C1CCC(C1)NC(=O)C=CC2=CC3=C(C=C2)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1575961
PubChem CID:	871734
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
Potency	11

Activity Type	# Activity
Individual Protein	10
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT54	Individual Protein	Nonstructural protein 1	Influenza A virus	Potency	=	3981.1	nM	PMID[521671]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	14125.4	nM	PMID[521671]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[521671]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[521671]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	15101.4	nM	PMID[521671]
NPT157	Individual Protein	Breast cancer type 1 susceptibility protein	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[521671]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[521671]
NPT1043	Individual Protein	Glycoprotein hormones alpha chain	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[521671]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	IC50	=	1130.0	nM	PMID[521672]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	IC50	>	100000.0	nM	PMID[521672]
NPT2	Others	Unspecified		Potency	=	3264.3	nM	PMID[521671]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	2078.7	nM	PMID[521671]
NPT2	Others	Unspecified		Potency	n.a.	7943.3	nM	PMID[521671]

☑ 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 NPC469977 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	203
0.1-0.2	1548
0.2-0.3	9152
0.3-0.4	9605
0.4-0.5	8374
0.5-0.6	10012
0.6-0.7	3348
0.7-0.8	411
0.8-0.85	23
0.85-0.9	6
0.9-0.95	14
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9597	High Similarity	NPC470706
0.9355	High Similarity	NPC251466
0.935	High Similarity	NPC300955
0.9274	High Similarity	NPC170583
0.9274	High Similarity	NPC246133
0.9274	High Similarity	NPC71105
0.9274	High Similarity	NPC152186
0.9274	High Similarity	NPC207541
0.9274	High Similarity	NPC182147
0.92	High Similarity	NPC156944
0.9127	High Similarity	NPC157740
0.9127	High Similarity	NPC291449
0.9127	High Similarity	NPC99798
0.9127	High Similarity	NPC41331
0.9055	High Similarity	NPC147247
0.9055	High Similarity	NPC246974
0.8855	High Similarity	NPC473463
0.8828	High Similarity	NPC191302
0.8712	High Similarity	NPC284855
0.8712	High Similarity	NPC282477
0.8519	High Similarity	NPC254610
0.8462	Intermediate Similarity	NPC301713
0.8397	Intermediate Similarity	NPC153990
0.8333	Intermediate Similarity	NPC275150
0.8333	Intermediate Similarity	NPC155838
0.8271	Intermediate Similarity	NPC195749
0.8271	Intermediate Similarity	NPC35961
0.8271	Intermediate Similarity	NPC52029
0.8261	Intermediate Similarity	NPC77572
0.8258	Intermediate Similarity	NPC186898
0.8197	Intermediate Similarity	NPC127326
0.8148	Intermediate Similarity	NPC214869
0.813	Intermediate Similarity	NPC31279
0.812	Intermediate Similarity	NPC251571
0.8099	Intermediate Similarity	NPC327623
0.8074	Intermediate Similarity	NPC114102
0.8074	Intermediate Similarity	NPC308885
0.8074	Intermediate Similarity	NPC255550
0.8015	Intermediate Similarity	NPC318862
0.8015	Intermediate Similarity	NPC130595
0.8015	Intermediate Similarity	NPC93882
0.7984	Intermediate Similarity	NPC57501
0.7956	Intermediate Similarity	NPC6854
0.7956	Intermediate Similarity	NPC313737
0.7956	Intermediate Similarity	NPC285078
0.792	Intermediate Similarity	NPC166837
0.7899	Intermediate Similarity	NPC193673
0.7899	Intermediate Similarity	NPC94280
0.7899	Intermediate Similarity	NPC218530
0.7899	Intermediate Similarity	NPC167096
0.7899	Intermediate Similarity	NPC103947
0.7899	Intermediate Similarity	NPC45783
0.7899	Intermediate Similarity	NPC159150
0.7899	Intermediate Similarity	NPC328419
0.7883	Intermediate Similarity	NPC217574
0.7857	Intermediate Similarity	NPC194359
0.7857	Intermediate Similarity	NPC41473
0.7857	Intermediate Similarity	NPC204848
0.7857	Intermediate Similarity	NPC312770
0.7857	Intermediate Similarity	NPC28641
0.7857	Intermediate Similarity	NPC160607
0.7857	Intermediate Similarity	NPC14600
0.7842	Intermediate Similarity	NPC230698
0.7842	Intermediate Similarity	NPC96406
0.7842	Intermediate Similarity	NPC196609
0.7842	Intermediate Similarity	NPC255817
0.7842	Intermediate Similarity	NPC251454
0.7842	Intermediate Similarity	NPC73883
0.7842	Intermediate Similarity	NPC277042
0.7842	Intermediate Similarity	NPC180647
0.7842	Intermediate Similarity	NPC205178
0.7842	Intermediate Similarity	NPC136330
0.782	Intermediate Similarity	NPC249788
0.7801	Intermediate Similarity	NPC296898
0.7801	Intermediate Similarity	NPC299583
0.7786	Intermediate Similarity	NPC145446
0.7786	Intermediate Similarity	NPC99078
0.7786	Intermediate Similarity	NPC137172
0.777	Intermediate Similarity	NPC474560
0.7752	Intermediate Similarity	NPC111225
0.7742	Intermediate Similarity	NPC227894
0.773	Intermediate Similarity	NPC220923
0.773	Intermediate Similarity	NPC470707
0.773	Intermediate Similarity	NPC248505
0.773	Intermediate Similarity	NPC193528
0.773	Intermediate Similarity	NPC95366
0.773	Intermediate Similarity	NPC252107
0.773	Intermediate Similarity	NPC225745
0.7727	Intermediate Similarity	NPC183262
0.771	Intermediate Similarity	NPC69670
0.7692	Intermediate Similarity	NPC199209
0.7692	Intermediate Similarity	NPC212643
0.7692	Intermediate Similarity	NPC33271
0.7692	Intermediate Similarity	NPC120075
0.7687	Intermediate Similarity	NPC140359
0.7687	Intermediate Similarity	NPC13020
0.7677	Intermediate Similarity	NPC198741
0.7674	Intermediate Similarity	NPC303370
0.7669	Intermediate Similarity	NPC80241
0.7669	Intermediate Similarity	NPC301641
0.766	Intermediate Similarity	NPC416184
0.7652	Intermediate Similarity	NPC263835
0.7652	Intermediate Similarity	NPC344161
0.7647	Intermediate Similarity	NPC40352
0.7647	Intermediate Similarity	NPC213711
0.7647	Intermediate Similarity	NPC274356
0.7638	Intermediate Similarity	NPC55300
0.7626	Intermediate Similarity	NPC118419
0.7623	Intermediate Similarity	NPC12714
0.7623	Intermediate Similarity	NPC310905
0.7622	Intermediate Similarity	NPC477837
0.7622	Intermediate Similarity	NPC477838
0.7619	Intermediate Similarity	NPC36108
0.7619	Intermediate Similarity	NPC233731
0.7619	Intermediate Similarity	NPC246358
0.7619	Intermediate Similarity	NPC7097
0.7612	Intermediate Similarity	NPC298486
0.7582	Intermediate Similarity	NPC69360
0.7578	Intermediate Similarity	NPC165646
0.7576	Intermediate Similarity	NPC43275
0.7576	Intermediate Similarity	NPC119949
0.7559	Intermediate Similarity	NPC137685
0.7557	Intermediate Similarity	NPC283468
0.7537	Intermediate Similarity	NPC211992
0.7537	Intermediate Similarity	NPC114845
0.7535	Intermediate Similarity	NPC7018
0.7519	Intermediate Similarity	NPC471308
0.7519	Intermediate Similarity	NPC289330
0.7519	Intermediate Similarity	NPC160120
0.7519	Intermediate Similarity	NPC17388
0.7519	Intermediate Similarity	NPC53596
0.7517	Intermediate Similarity	NPC222039
0.7517	Intermediate Similarity	NPC100478
0.75	Intermediate Similarity	NPC156840
0.75	Intermediate Similarity	NPC257124
0.75	Intermediate Similarity	NPC8547
0.75	Intermediate Similarity	NPC78918
0.75	Intermediate Similarity	NPC292792
0.75	Intermediate Similarity	NPC122009
0.75	Intermediate Similarity	NPC173746
0.75	Intermediate Similarity	NPC139617
0.7483	Intermediate Similarity	NPC5462
0.7482	Intermediate Similarity	NPC470633
0.7482	Intermediate Similarity	NPC228769
0.7481	Intermediate Similarity	NPC256167
0.7465	Intermediate Similarity	NPC11147
0.7463	Intermediate Similarity	NPC83279
0.7462	Intermediate Similarity	NPC142599
0.7462	Intermediate Similarity	NPC294941
0.746	Intermediate Similarity	NPC258171
0.745	Intermediate Similarity	NPC475959
0.7447	Intermediate Similarity	NPC259742
0.7447	Intermediate Similarity	NPC147616
0.7447	Intermediate Similarity	NPC219671
0.7447	Intermediate Similarity	NPC104077
0.7444	Intermediate Similarity	NPC256369
0.7436	Intermediate Similarity	NPC189782
0.7429	Intermediate Similarity	NPC184814
0.7429	Intermediate Similarity	NPC171550
0.7429	Intermediate Similarity	NPC134764
0.7429	Intermediate Similarity	NPC63574
0.7429	Intermediate Similarity	NPC476570
0.7429	Intermediate Similarity	NPC275950
0.7426	Intermediate Similarity	NPC211218
0.7419	Intermediate Similarity	NPC97072
0.7419	Intermediate Similarity	NPC215829
0.7413	Intermediate Similarity	NPC469808
0.7407	Intermediate Similarity	NPC193484
0.7402	Intermediate Similarity	NPC146530
0.74	Intermediate Similarity	NPC182119
0.7397	Intermediate Similarity	NPC475698
0.7394	Intermediate Similarity	NPC169973
0.7391	Intermediate Similarity	NPC473960
0.7389	Intermediate Similarity	NPC89199
0.7389	Intermediate Similarity	NPC54125
0.7376	Intermediate Similarity	NPC476345
0.7372	Intermediate Similarity	NPC95733
0.7372	Intermediate Similarity	NPC62101
0.7368	Intermediate Similarity	NPC270811
0.7368	Intermediate Similarity	NPC471073
0.7365	Intermediate Similarity	NPC469978
0.7365	Intermediate Similarity	NPC145304
0.7353	Intermediate Similarity	NPC471315
0.7353	Intermediate Similarity	NPC471314
0.7348	Intermediate Similarity	NPC258992
0.7347	Intermediate Similarity	NPC178466
0.7347	Intermediate Similarity	NPC63628
0.7343	Intermediate Similarity	NPC264956
0.7338	Intermediate Similarity	NPC177167
0.7338	Intermediate Similarity	NPC158737
0.7338	Intermediate Similarity	NPC172403
0.7338	Intermediate Similarity	NPC291847
0.7333	Intermediate Similarity	NPC471032
0.7333	Intermediate Similarity	NPC153644
0.7333	Intermediate Similarity	NPC470935
0.7329	Intermediate Similarity	NPC228040
0.7324	Intermediate Similarity	NPC227002
0.7324	Intermediate Similarity	NPC97316
0.7324	Intermediate Similarity	NPC471505
0.7324	Intermediate Similarity	NPC252833

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 NPC469977 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	639
0.2-0.3	1287
0.3-0.4	2511
0.4-0.5	2642
0.5-0.6	1381
0.6-0.7	480
0.7-0.8	53
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	NPD554	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1357	Approved
0.8074	Intermediate Similarity	NPD3145	Approved
0.8074	Intermediate Similarity	NPD3144	Approved
0.8015	Intermediate Similarity	NPD2674	Phase 3
0.7929	Intermediate Similarity	NPD2161	Phase 2
0.7862	Intermediate Similarity	NPD4739	Approved
0.7842	Intermediate Similarity	NPD2492	Phase 1
0.7754	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1375	Discontinued
0.7609	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6331	Phase 2
0.7566	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD1669	Approved
0.7556	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5604	Discontinued
0.75	Intermediate Similarity	NPD2922	Phase 1
0.75	Intermediate Similarity	NPD228	Approved
0.75	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD2157	Approved
0.7451	Intermediate Similarity	NPD2978	Approved
0.7451	Intermediate Similarity	NPD2977	Approved
0.7448	Intermediate Similarity	NPD7153	Discontinued
0.7407	Intermediate Similarity	NPD3705	Approved
0.7407	Intermediate Similarity	NPD776	Approved
0.74	Intermediate Similarity	NPD2122	Discontinued
0.7397	Intermediate Similarity	NPD4237	Approved
0.7397	Intermediate Similarity	NPD4236	Phase 3
0.7365	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD4108	Discontinued
0.7347	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5772	Approved
0.7338	Intermediate Similarity	NPD1712	Approved
0.7338	Intermediate Similarity	NPD5773	Approved
0.7333	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD52	Approved
0.7333	Intermediate Similarity	NPD7526	Approved
0.7286	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4123	Phase 3
0.7267	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1024	Discontinued
0.7222	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD2040	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD5111	Phase 2
0.7183	Intermediate Similarity	NPD5718	Phase 2
0.7183	Intermediate Similarity	NPD5109	Approved
0.7183	Intermediate Similarity	NPD5110	Phase 2
0.7181	Intermediate Similarity	NPD5241	Discontinued
0.7143	Intermediate Similarity	NPD709	Approved
0.7143	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD5283	Phase 1
0.7105	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4357	Discontinued
0.7078	Intermediate Similarity	NPD4005	Discontinued
0.7067	Intermediate Similarity	NPD2219	Phase 1
0.705	Intermediate Similarity	NPD3685	Discontinued
0.7047	Intermediate Similarity	NPD3060	Approved
0.7045	Intermediate Similarity	NPD821	Approved
0.7032	Intermediate Similarity	NPD4675	Approved
0.7032	Intermediate Similarity	NPD4678	Approved
0.7014	Intermediate Similarity	NPD840	Approved
0.7014	Intermediate Similarity	NPD839	Approved
0.7007	Intermediate Similarity	NPD2667	Approved
0.7007	Intermediate Similarity	NPD2668	Approved
0.6987	Remote Similarity	NPD5090	Approved
0.6987	Remote Similarity	NPD5089	Approved
0.6986	Remote Similarity	NPD2653	Approved
0.698	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2233	Approved
0.6978	Remote Similarity	NPD2232	Approved
0.6978	Remote Similarity	NPD2230	Approved
0.6978	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4993	Discontinued
0.6966	Remote Similarity	NPD1558	Phase 1
0.6962	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6895	Approved
0.6939	Remote Similarity	NPD6896	Approved
0.6933	Remote Similarity	NPD4162	Approved
0.6929	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD9377	Approved
0.6917	Remote Similarity	NPD9379	Approved
0.6913	Remote Similarity	NPD3656	Approved
0.6912	Remote Similarity	NPD5536	Phase 2
0.6903	Remote Similarity	NPD4210	Discontinued
0.6897	Remote Similarity	NPD1423	Approved
0.6894	Remote Similarity	NPD2644	Approved
0.6892	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4055	Discovery
0.6863	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2231	Phase 2
0.6857	Remote Similarity	NPD2235	Phase 2
0.6831	Remote Similarity	NPD1819	Approved
0.6831	Remote Similarity	NPD1820	Approved
0.6831	Remote Similarity	NPD1817	Approved
0.6831	Remote Similarity	NPD1818	Approved
0.6828	Remote Similarity	NPD1039	Discontinued
0.6828	Remote Similarity	NPD1048	Approved
0.6824	Remote Similarity	NPD6111	Discontinued
0.6821	Remote Similarity	NPD5177	Phase 3
0.6818	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD593	Approved
0.6815	Remote Similarity	NPD595	Approved
0.6809	Remote Similarity	NPD1421	Approved
0.6809	Remote Similarity	NPD1420	Approved
0.6806	Remote Similarity	NPD596	Approved
0.6806	Remote Similarity	NPD600	Approved
0.6802	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3686	Approved
0.6795	Remote Similarity	NPD3687	Approved
0.679	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD558	Phase 2
0.6783	Remote Similarity	NPD6584	Phase 3
0.6781	Remote Similarity	NPD7477	Discontinued
0.6768	Remote Similarity	NPD4083	Discontinued
0.6761	Remote Similarity	NPD196	Phase 1
0.6755	Remote Similarity	NPD2808	Discontinued
0.6755	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD3111	Phase 1
0.6748	Remote Similarity	NPD2821	Approved
0.6742	Remote Similarity	NPD2684	Approved
0.6739	Remote Similarity	NPD1182	Approved
0.6735	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3692	Discontinued
0.6713	Remote Similarity	NPD3053	Approved
0.6713	Remote Similarity	NPD3055	Approved
0.671	Remote Similarity	NPD4584	Approved
0.6707	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7281	Phase 3
0.6706	Remote Similarity	NPD7280	Phase 3
0.6692	Remote Similarity	NPD556	Approved
0.669	Remote Similarity	NPD2983	Phase 2
0.669	Remote Similarity	NPD9622	Approved
0.669	Remote Similarity	NPD2982	Phase 2
0.6688	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1350	Approved
0.6667	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6390	Discontinued
0.6667	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5745	Approved
0.6667	Remote Similarity	NPD1351	Approved
0.6667	Remote Similarity	NPD1349	Approved
0.6667	Remote Similarity	NPD4110	Phase 3
0.6667	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1358	Approved
0.6646	Remote Similarity	NPD2560	Approved
0.6646	Remote Similarity	NPD824	Approved
0.6646	Remote Similarity	NPD2563	Approved
0.6645	Remote Similarity	NPD5297	Approved
0.6644	Remote Similarity	NPD3027	Phase 3
0.6644	Remote Similarity	NPD3164	Approved
0.6644	Remote Similarity	NPD3167	Approved
0.6644	Remote Similarity	NPD3179	Approved
0.6644	Remote Similarity	NPD3180	Approved
0.6644	Remote Similarity	NPD3166	Approved
0.6644	Remote Similarity	NPD3165	Approved
0.6644	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD9381	Approved
0.6643	Remote Similarity	NPD9384	Approved
0.6642	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7007	Discovery
0.6623	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD2238	Phase 2
0.6622	Remote Similarity	NPD3620	Phase 2
0.6622	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD2250	Discontinued
0.6621	Remote Similarity	NPD9494	Approved
0.6621	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.662	Remote Similarity	NPD2981	Phase 2
0.6606	Remote Similarity	NPD7315	Approved
0.6604	Remote Similarity	NPD7028	Phase 2
0.6604	Remote Similarity	NPD1642	Discontinued
0.6603	Remote Similarity	NPD2505	Approved
0.6603	Remote Similarity	NPD2504	Approved
0.6599	Remote Similarity	NPD597	Approved
0.6599	Remote Similarity	NPD601	Approved
0.6599	Remote Similarity	NPD598	Approved
0.6597	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD1794	Approved
0.6591	Remote Similarity	NPD1444	Approved
0.6591	Remote Similarity	NPD1445	Approved
0.6587	Remote Similarity	NPD9296	Approved
0.6582	Remote Similarity	NPD2883	Discontinued
0.6581	Remote Similarity	NPD7124	Phase 2
0.6573	Remote Similarity	NPD6582	Phase 2
0.6573	Remote Similarity	NPD6583	Phase 3
0.6571	Remote Similarity	NPD1797	Approved
0.6571	Remote Similarity	NPD1798	Approved
0.6566	Remote Similarity	NPD2969	Approved
0.6566	Remote Similarity	NPD2970	Approved
0.6565	Remote Similarity	NPD9610	Approved
0.6565	Remote Similarity	NPD9608	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