NPASS Compound

Structure

CID180647 OpenBabel06191715552D 23 25 0 0 0 0 0 0 0 0999 V2000 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 -3.1910 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 7.0132 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 -2.6910 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 7.8793 0.3090 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 7.8793 -1.6910 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 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 8.7453 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 -1.1910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 0.3090 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 4 1 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 11 2 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 14 18 1 0 0 0 0 15 22 1 0 0 0 0 15 23 1 0 0 0 0 17 18 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	315.18
Volume:	335.696
LogP:	3.255
LogD:	3.079
LogS:	-3.568
# Rotatable Bonds:	7
TPSA:	38.77
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.745
Synthetic Accessibility Score:	2.186
Fsp3:	0.526
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:	-4.809
MDCK Permeability:	3.118427048320882e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.484
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.931
30% Bioavailability (F30%):	0.058

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.974
Plasma Protein Binding (PPB):	95.53755950927734%
Volume Distribution (VD):	0.777
Pgp-substrate:	3.7998671531677246%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.361
CYP2C19-inhibitor:	0.931
CYP2C19-substrate:	0.22
CYP2C9-inhibitor:	0.691
CYP2C9-substrate:	0.842
CYP2D6-inhibitor:	0.939
CYP2D6-substrate:	0.764
CYP3A4-inhibitor:	0.956
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	13.052
Half-life (T1/2):	0.387

ADMET: Toxicity

hERG Blockers:	0.723
Human Hepatotoxicity (H-HT):	0.21
Drug-inuced Liver Injury (DILI):	0.683
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.226
Skin Sensitization:	0.951
Carcinogencity:	0.735
Eye Corrosion:	0.011
Eye Irritation:	0.11
Respiratory Toxicity:	0.261

Download Data

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

Natural Product: NPC180647

Natural Product ID:	NPC180647
*Common Name:**	Piperettine
IUPAC Name:	(E)-7-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylhept-6-en-1-one
Synonyms:	Piperettine
Standard InCHIKey:	MIWPBXQTBYPJEF-XBXARRHUSA-N
Standard InCHI:	InChI=1S/C19H25NO3/c21-19(20-12-6-3-7-13-20)9-5-2-1-4-8-16-10-11-17-18(14-16)23-15-22-17/h4,8,10-11,14H,1-3,5-7,9,12-13,15H2/b8-4+
SMILES:	C(CCCC(=O)N1CCCCC1)/C=C/c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1086887
PubChem CID:	11141599
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]
NPO26687	Piper aurantiacum	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]
NPO26687	Piper aurantiacum	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
Others	13

Activity Type	# Activity
Organism	12
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	32.0	%	PMID[452624]
NPT2564	Organism	Blumeria graminis	Blumeria graminis	Activity	=	40.0	%	PMID[452625]
NPT2564	Organism	Blumeria graminis	Blumeria graminis	Activity	=	60.0	%	PMID[452625]
NPT829	Organism	Puccinia recondita	Puccinia recondita	Activity	=	0.0	%	PMID[452625]
NPT825	Organism	Phytophthora infestans	Phytophthora infestans	Activity	=	0.0	%	PMID[452625]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	Activity	=	0.0	%	PMID[452625]
NPT529	Organism	Rhizoctonia solani	Rhizoctonia solani	Activity	=	0.0	%	PMID[452625]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	Activity	=	0.0	%	PMID[452625]

☑ 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 NPC180647 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	233
0.1-0.2	1368
0.2-0.3	6224
0.3-0.4	12530
0.4-0.5	5446
0.5-0.6	12749
0.6-0.7	3767
0.7-0.8	338
0.8-0.85	11
0.85-0.9	13
0.9-0.95	16
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9845	High Similarity	NPC225745
0.9394	High Similarity	NPC194359
0.9394	High Similarity	NPC28641
0.9389	High Similarity	NPC255817
0.9389	High Similarity	NPC251454
0.9389	High Similarity	NPC277042
0.9389	High Similarity	NPC136330
0.9389	High Similarity	NPC230698
0.9389	High Similarity	NPC196609
0.9389	High Similarity	NPC205178
0.9389	High Similarity	NPC73883
0.9318	High Similarity	NPC99078
0.9313	High Similarity	NPC167096
0.9308	High Similarity	NPC318862
0.9248	High Similarity	NPC220923
0.9248	High Similarity	NPC470707
0.9248	High Similarity	NPC252107
0.8881	High Similarity	NPC45783
0.8881	High Similarity	NPC94280
0.8881	High Similarity	NPC193673
0.8881	High Similarity	NPC159150
0.8881	High Similarity	NPC328419
0.8881	High Similarity	NPC103947
0.8815	High Similarity	NPC96406
0.875	High Similarity	NPC137172
0.875	High Similarity	NPC145446
0.8731	High Similarity	NPC217574
0.8686	High Similarity	NPC248505
0.8686	High Similarity	NPC95366
0.8652	High Similarity	NPC469978
0.8613	High Similarity	NPC469808
0.8503	High Similarity	NPC169742
0.8414	Intermediate Similarity	NPC470088
0.8367	Intermediate Similarity	NPC471073
0.8367	Intermediate Similarity	NPC270811
0.8311	Intermediate Similarity	NPC470708
0.8227	Intermediate Similarity	NPC231572
0.8214	Intermediate Similarity	NPC416184
0.8194	Intermediate Similarity	NPC244338
0.8085	Intermediate Similarity	NPC7018
0.8043	Intermediate Similarity	NPC470706
0.7956	Intermediate Similarity	NPC251466
0.7943	Intermediate Similarity	NPC473463
0.7926	Intermediate Similarity	NPC256167
0.7885	Intermediate Similarity	NPC231198
0.7883	Intermediate Similarity	NPC71105
0.7883	Intermediate Similarity	NPC182147
0.7883	Intermediate Similarity	NPC170583
0.7883	Intermediate Similarity	NPC207541
0.7883	Intermediate Similarity	NPC246133
0.7883	Intermediate Similarity	NPC152186
0.7852	Intermediate Similarity	NPC475959
0.7842	Intermediate Similarity	NPC469977
0.7826	Intermediate Similarity	NPC156944
0.7812	Intermediate Similarity	NPC127326
0.781	Intermediate Similarity	NPC300955
0.7801	Intermediate Similarity	NPC118419
0.7778	Intermediate Similarity	NPC214036
0.7778	Intermediate Similarity	NPC113236
0.777	Intermediate Similarity	NPC157740
0.777	Intermediate Similarity	NPC41331
0.777	Intermediate Similarity	NPC291449
0.777	Intermediate Similarity	NPC191302
0.777	Intermediate Similarity	NPC99798
0.777	Intermediate Similarity	NPC172403
0.7761	Intermediate Similarity	NPC69670
0.7752	Intermediate Similarity	NPC31279
0.7748	Intermediate Similarity	NPC223125
0.7744	Intermediate Similarity	NPC102760
0.7736	Intermediate Similarity	NPC241055
0.773	Intermediate Similarity	NPC477694
0.773	Intermediate Similarity	NPC477705
0.7714	Intermediate Similarity	NPC147247
0.7714	Intermediate Similarity	NPC246974
0.7697	Intermediate Similarity	NPC119669
0.7697	Intermediate Similarity	NPC116007
0.7692	Intermediate Similarity	NPC284855
0.7692	Intermediate Similarity	NPC282477
0.7676	Intermediate Similarity	NPC477706
0.7669	Intermediate Similarity	NPC111225
0.766	Intermediate Similarity	NPC160193
0.7651	Intermediate Similarity	NPC145304
0.7647	Intermediate Similarity	NPC148898
0.7647	Intermediate Similarity	NPC223124
0.7643	Intermediate Similarity	NPC64948
0.7639	Intermediate Similarity	NPC11147
0.7622	Intermediate Similarity	NPC266425
0.7612	Intermediate Similarity	NPC199209
0.7612	Intermediate Similarity	NPC212643
0.7605	Intermediate Similarity	NPC477259
0.7605	Intermediate Similarity	NPC169387
0.7591	Intermediate Similarity	NPC114845
0.759	Intermediate Similarity	NPC83511
0.7574	Intermediate Similarity	NPC344161
0.7569	Intermediate Similarity	NPC205915
0.7548	Intermediate Similarity	NPC138487
0.7548	Intermediate Similarity	NPC76079
0.7548	Intermediate Similarity	NPC216459
0.7548	Intermediate Similarity	NPC93593
0.7548	Intermediate Similarity	NPC78733
0.7548	Intermediate Similarity	NPC41178
0.7547	Intermediate Similarity	NPC168409
0.7536	Intermediate Similarity	NPC298486
0.7534	Intermediate Similarity	NPC254610
0.7534	Intermediate Similarity	NPC193528
0.7532	Intermediate Similarity	NPC210148
0.7532	Intermediate Similarity	NPC233029
0.7518	Intermediate Similarity	NPC286683
0.7517	Intermediate Similarity	NPC110958
0.7517	Intermediate Similarity	NPC19890
0.7516	Intermediate Similarity	NPC106786
0.75	Intermediate Similarity	NPC146288
0.75	Intermediate Similarity	NPC31311
0.75	Intermediate Similarity	NPC37144
0.75	Intermediate Similarity	NPC120066
0.75	Intermediate Similarity	NPC57501
0.75	Intermediate Similarity	NPC471650
0.75	Intermediate Similarity	NPC234392
0.75	Intermediate Similarity	NPC59907
0.7484	Intermediate Similarity	NPC59567
0.7468	Intermediate Similarity	NPC26353
0.7465	Intermediate Similarity	NPC283079
0.7464	Intermediate Similarity	NPC193484
0.7464	Intermediate Similarity	NPC80241
0.7464	Intermediate Similarity	NPC301641
0.7451	Intermediate Similarity	NPC469540
0.7451	Intermediate Similarity	NPC469539
0.7451	Intermediate Similarity	NPC211296
0.745	Intermediate Similarity	NPC138438
0.745	Intermediate Similarity	NPC908
0.7447	Intermediate Similarity	NPC218323
0.7438	Intermediate Similarity	NPC306669
0.7438	Intermediate Similarity	NPC35345
0.7432	Intermediate Similarity	NPC314682
0.7423	Intermediate Similarity	NPC303581
0.7423	Intermediate Similarity	NPC67978
0.7415	Intermediate Similarity	NPC230968
0.7415	Intermediate Similarity	NPC102260
0.741	Intermediate Similarity	NPC27887
0.7407	Intermediate Similarity	NPC86469
0.7407	Intermediate Similarity	NPC268317
0.7397	Intermediate Similarity	NPC475828
0.7394	Intermediate Similarity	NPC223807
0.7391	Intermediate Similarity	NPC474858
0.7383	Intermediate Similarity	NPC188163
0.7383	Intermediate Similarity	NPC474915
0.7383	Intermediate Similarity	NPC328750
0.7383	Intermediate Similarity	NPC213206
0.7376	Intermediate Similarity	NPC85830
0.7365	Intermediate Similarity	NPC231719
0.7365	Intermediate Similarity	NPC52968
0.7362	Intermediate Similarity	NPC474708
0.7358	Intermediate Similarity	NPC160298
0.7358	Intermediate Similarity	NPC215829
0.7358	Intermediate Similarity	NPC232924
0.7358	Intermediate Similarity	NPC306902
0.7358	Intermediate Similarity	NPC266753
0.7358	Intermediate Similarity	NPC477559
0.7358	Intermediate Similarity	NPC135006
0.7358	Intermediate Similarity	NPC97072
0.7357	Intermediate Similarity	NPC249788
0.7353	Intermediate Similarity	NPC120075
0.7353	Intermediate Similarity	NPC185738
0.7353	Intermediate Similarity	NPC33271
0.7347	Intermediate Similarity	NPC42793
0.7347	Intermediate Similarity	NPC231884
0.7347	Intermediate Similarity	NPC167944
0.7341	Intermediate Similarity	NPC477258
0.7341	Intermediate Similarity	NPC470646
0.7333	Intermediate Similarity	NPC308267
0.7324	Intermediate Similarity	NPC301713
0.732	Intermediate Similarity	NPC95075
0.732	Intermediate Similarity	NPC90844
0.732	Intermediate Similarity	NPC253883
0.7303	Intermediate Similarity	NPC130926
0.7303	Intermediate Similarity	NPC189908
0.7301	Intermediate Similarity	NPC475845
0.7299	Intermediate Similarity	NPC159916
0.7299	Intermediate Similarity	NPC24228
0.7299	Intermediate Similarity	NPC205502
0.7296	Intermediate Similarity	NPC111485
0.7296	Intermediate Similarity	NPC477080
0.7292	Intermediate Similarity	NPC476748
0.7273	Intermediate Similarity	NPC4669
0.7267	Intermediate Similarity	NPC275150
0.7267	Intermediate Similarity	NPC470855
0.7266	Intermediate Similarity	NPC12714
0.7266	Intermediate Similarity	NPC471877
0.7266	Intermediate Similarity	NPC310905
0.7266	Intermediate Similarity	NPC158949
0.726	Intermediate Similarity	NPC160692
0.7257	Intermediate Similarity	NPC71124
0.7254	Intermediate Similarity	NPC17348
0.725	Intermediate Similarity	NPC158900
0.7246	Intermediate Similarity	NPC119949
0.7239	Intermediate Similarity	NPC474324
0.7239	Intermediate Similarity	NPC57812
0.723	Intermediate Similarity	NPC131204
0.723	Intermediate Similarity	NPC301050
0.7226	Intermediate Similarity	NPC219162

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 NPC180647 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	666
0.2-0.3	1107
0.3-0.4	2304
0.4-0.5	2610
0.5-0.6	1588
0.6-0.7	627
0.7-0.8	78
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9389	High Similarity	NPD2492	Phase 1
0.8014	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD5297	Approved
0.7947	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD7110	Phase 1
0.7919	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5718	Phase 2
0.7823	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3146	Approved
0.7667	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6875	Approved
0.7647	Intermediate Similarity	NPD6876	Approved
0.7582	Intermediate Similarity	NPD824	Approved
0.7576	Intermediate Similarity	NPD7280	Phase 3
0.7576	Intermediate Similarity	NPD7281	Phase 3
0.7566	Intermediate Similarity	NPD3640	Phase 3
0.7566	Intermediate Similarity	NPD3639	Approved
0.7566	Intermediate Similarity	NPD3641	Approved
0.7546	Intermediate Similarity	NPD3885	Approved
0.7535	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD5978	Approved
0.7452	Intermediate Similarity	NPD5977	Approved
0.7403	Intermediate Similarity	NPD4124	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4210	Discontinued
0.7397	Intermediate Similarity	NPD2653	Approved
0.7391	Intermediate Similarity	NPD4166	Phase 2
0.7383	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD3142	Approved
0.7379	Intermediate Similarity	NPD3140	Approved
0.7372	Intermediate Similarity	NPD6873	Phase 2
0.7372	Intermediate Similarity	NPD1357	Approved
0.7372	Intermediate Similarity	NPD6385	Approved
0.7372	Intermediate Similarity	NPD6386	Approved
0.7358	Intermediate Similarity	NPD5604	Discontinued
0.7353	Intermediate Similarity	NPD5536	Phase 2
0.7347	Intermediate Similarity	NPD6896	Approved
0.7347	Intermediate Similarity	NPD743	Approved
0.7347	Intermediate Similarity	NPD6895	Approved
0.7333	Intermediate Similarity	NPD4236	Phase 3
0.7333	Intermediate Similarity	NPD4237	Approved
0.7325	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6297	Approved
0.7273	Intermediate Similarity	NPD5312	Approved
0.7273	Intermediate Similarity	NPD5313	Approved
0.7214	Intermediate Similarity	NPD3705	Approved
0.7175	Intermediate Similarity	NPD5457	Discontinued
0.717	Intermediate Similarity	NPD2978	Approved
0.717	Intermediate Similarity	NPD2977	Approved
0.7125	Intermediate Similarity	NPD5353	Approved
0.7124	Intermediate Similarity	NPD2219	Phase 1
0.7122	Intermediate Similarity	NPD6382	Discontinued
0.7118	Intermediate Similarity	NPD6853	Approved
0.7118	Intermediate Similarity	NPD6851	Approved
0.7114	Intermediate Similarity	NPD6111	Discontinued
0.7113	Intermediate Similarity	NPD1421	Approved
0.7113	Intermediate Similarity	NPD1420	Approved
0.7105	Intermediate Similarity	NPD5177	Phase 3
0.7101	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4584	Approved
0.7086	Intermediate Similarity	NPD3656	Approved
0.7075	Intermediate Similarity	NPD2245	Discovery
0.7075	Intermediate Similarity	NPD3531	Approved
0.7075	Intermediate Similarity	NPD3532	Approved
0.7075	Intermediate Similarity	NPD3530	Approved
0.7071	Intermediate Similarity	NPD2667	Approved
0.7071	Intermediate Similarity	NPD2668	Approved
0.7063	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5283	Phase 1
0.7047	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3447	Discontinued
0.702	Intermediate Similarity	NPD1725	Approved
0.7019	Intermediate Similarity	NPD5967	Approved
0.7018	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6618	Phase 2
0.7013	Intermediate Similarity	NPD5241	Discontinued
0.7007	Intermediate Similarity	NPD3144	Approved
0.7007	Intermediate Similarity	NPD3145	Approved
0.7006	Intermediate Similarity	NPD1670	Discontinued
0.7006	Intermediate Similarity	NPD2122	Discontinued
0.7	Intermediate Similarity	NPD7248	Discontinued
0.6993	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3060	Approved
0.6993	Remote Similarity	NPD4162	Approved
0.6987	Remote Similarity	NPD1424	Approved
0.6978	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1375	Discontinued
0.6968	Remote Similarity	NPD5295	Discontinued
0.6968	Remote Similarity	NPD7124	Phase 2
0.6959	Remote Similarity	NPD2674	Phase 3
0.6957	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4110	Phase 3
0.6948	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2922	Phase 1
0.6943	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2233	Approved
0.6923	Remote Similarity	NPD4357	Discontinued
0.6923	Remote Similarity	NPD2232	Approved
0.6923	Remote Similarity	NPD2230	Approved
0.6918	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4017	Approved
0.6913	Remote Similarity	NPD3109	Approved
0.6913	Remote Similarity	NPD3110	Approved
0.6909	Remote Similarity	NPD6107	Approved
0.6899	Remote Similarity	NPD6030	Approved
0.6899	Remote Similarity	NPD4727	Phase 1
0.6899	Remote Similarity	NPD6031	Approved
0.6899	Remote Similarity	NPD7131	Phase 3
0.6899	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7427	Discontinued
0.6897	Remote Similarity	NPD3349	Phase 2
0.6897	Remote Similarity	NPD7291	Discontinued
0.6894	Remote Similarity	NPD3384	Approved
0.6894	Remote Similarity	NPD3383	Approved
0.6894	Remote Similarity	NPD3382	Approved
0.6893	Remote Similarity	NPD6493	Phase 3
0.6892	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7119	Phase 2
0.6886	Remote Similarity	NPD4481	Phase 3
0.6879	Remote Similarity	NPD4739	Approved
0.6872	Remote Similarity	NPD4420	Approved
0.6871	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2614	Approved
0.686	Remote Similarity	NPD2968	Approved
0.686	Remote Similarity	NPD2971	Approved
0.6859	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3686	Approved
0.6855	Remote Similarity	NPD3687	Approved
0.6852	Remote Similarity	NPD5772	Approved
0.6852	Remote Similarity	NPD5773	Approved
0.6849	Remote Similarity	NPD7905	Discontinued
0.6848	Remote Similarity	NPD2904	Discontinued
0.6848	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5677	Discontinued
0.6848	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5746	Approved
0.6818	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2161	Phase 2
0.6797	Remote Similarity	NPD4476	Approved
0.6797	Remote Similarity	NPD6032	Approved
0.6797	Remote Similarity	NPD2239	Approved
0.6797	Remote Similarity	NPD2240	Approved
0.6797	Remote Similarity	NPD4477	Approved
0.6795	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD228	Approved
0.6786	Remote Similarity	NPD3596	Phase 2
0.6781	Remote Similarity	NPD4098	Discontinued
0.6779	Remote Similarity	NPD1336	Approved
0.6774	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2654	Approved
0.6772	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.677	Remote Similarity	NPD2592	Discontinued
0.677	Remote Similarity	NPD7028	Phase 2
0.6766	Remote Similarity	NPD7608	Discontinued
0.6761	Remote Similarity	NPD2594	Approved
0.6761	Remote Similarity	NPD2595	Approved
0.6761	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.676	Remote Similarity	NPD5582	Discontinued
0.676	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1755	Approved
0.6755	Remote Similarity	NPD4618	Approved
0.6755	Remote Similarity	NPD4622	Approved
0.6752	Remote Similarity	NPD2120	Phase 2
0.6748	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7018	Phase 2
0.6733	Remote Similarity	NPD5745	Approved
0.6732	Remote Similarity	NPD2164	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD4108	Discontinued
0.6731	Remote Similarity	NPD6331	Phase 2
0.6731	Remote Similarity	NPD5754	Discontinued
0.6728	Remote Similarity	NPD4772	Phase 2
0.6728	Remote Similarity	NPD4773	Phase 2
0.6727	Remote Similarity	NPD1307	Phase 2
0.6727	Remote Similarity	NPD1309	Phase 2
0.6726	Remote Similarity	NPD5242	Approved
0.6721	Remote Similarity	NPD5005	Approved
0.6721	Remote Similarity	NPD5006	Approved
0.6712	Remote Similarity	NPD196	Phase 1
0.6711	Remote Similarity	NPD5163	Phase 2
0.671	Remote Similarity	NPD2897	Discontinued
0.6708	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2563	Approved
0.6707	Remote Similarity	NPD2560	Approved
0.6706	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2486	Discontinued
0.6689	Remote Similarity	NPD9494	Approved
0.6688	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7298	Approved
0.6687	Remote Similarity	NPD5976	Discontinued

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