NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	265.07
Volume:	267.342
LogP:	3.928
LogD:	2.917
LogS:	-5.64
# Rotatable Bonds:	1
TPSA:	58.56
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.664
Synthetic Accessibility Score:	2.462
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.013
MDCK Permeability:	1.0279171874572057e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.14
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.116
Plasma Protein Binding (PPB):	94.94147491455078%
Volume Distribution (VD):	0.64
Pgp-substrate:	6.055291175842285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.912
CYP2C19-inhibitor:	0.27
CYP2C19-substrate:	0.233
CYP2C9-inhibitor:	0.692
CYP2C9-substrate:	0.798
CYP2D6-inhibitor:	0.604
CYP2D6-substrate:	0.316
CYP3A4-inhibitor:	0.314
CYP3A4-substrate:	0.108

ADMET: Excretion

Clearance (CL):	2.096
Half-life (T1/2):	0.48

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.237
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.81
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.684
Skin Sensitization:	0.931
Carcinogencity:	0.815
Eye Corrosion:	0.009
Eye Irritation:	0.76
Respiratory Toxicity:	0.85

Download Data

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

Natural Product: NPC311936

Natural Product ID:	NPC311936
*Common Name:**	Piperolactam A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KBGNBPGXVKPRQI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H11NO3/c1-20-12-7-10-13-11(17-16(10)19)6-8-4-2-3-5-9(8)14(13)15(12)18/h2-7,18H,1H3,(H,17,19)
SMILES:	COc1cc2c3c(cc4ccccc4c3c1O)N=C2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL387864
PubChem CID:	3081016
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002663] Aristolactams

*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
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978218]
NPO23507	Fissistigma balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978218]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872768]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	stem	n.a.	n.a.	PMID[17081761]
NPO26094	Stolonica socialis	Species	Styelidae	Eukaryota	n.a.	At a depth between 3 and 15 m in Las Lajas (Cdiz, Spain) (3606'11'' N, 525'47'' W)	2003-SEP	PMID[20014800]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	fruits	n.a.	n.a.	PMID[20839888]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21158422]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	whole plant	Luxi County, Yunnan Province, China	2008-OCT	PMID[21158422]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23434420]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29099182]
NPO30274	Pararistolochia flos-avis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3437282]
NPO30274	Pararistolochia flos-avis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8287	Piper taiwanense	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13925	Piper hamiltonii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26195	Tephrosia crassifolia	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13925	Piper hamiltonii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8287	Piper taiwanense	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26405	Duguetia staudtii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO989	Piper boehmeriifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28392	Macrosiphum liriodendri	Species	Aphididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13925	Piper hamiltonii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26094	Stolonica socialis	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28510	Aspergillus pseudodeflectus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9769	Mortonia palmeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23507	Fissistigma balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28938	Artemisia coerulescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11236	Mycale mytilorum	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8287	Piper taiwanense	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28218	Asplenium adiantum-nigrum	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26195	Tephrosia crassifolia	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10517	Aconitum vilmorini	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26405	Duguetia staudtii	Species	Annonaceae	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
GI50	4
IC50	2
Others	11

Activity Type	# Activity
Cell Line	2
CELL-LINE	8
NON-MOLECULAR	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1076	Cell Line	B-cells		IC50	=	1300.0	nM	PMID[555908]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	>	30000.0	nM	PMID[555911]
NPT27	Others	Unspecified		CC50	=	8120.0	nM	PMID[555908]
NPT2	Others	Unspecified		IC50	=	798.0	nM	PMID[555908]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	10.0	n.a.	PMID[555908]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	6.0	n.a.	PMID[555908]
NPT20967	CELL-LINE	Platelet	n.a.	Inhibition	=	84.3	%	PMID[555910]
NPT20967	CELL-LINE	Platelet	n.a.	Inhibition	=	0.0	%	PMID[555910]
NPT20967	CELL-LINE	Platelet	n.a.	Inhibition	=	84.1	%	PMID[555910]
NPT20967	CELL-LINE	Platelet	n.a.	Inhibition	=	14.7	%	PMID[555910]
NPT20967	CELL-LINE	Platelet	n.a.	Inhibition	=	83.5	%	PMID[555910]
NPT20967	CELL-LINE	Platelet	n.a.	Inhibition	=	22.2	%	PMID[555910]
NPT20967	CELL-LINE	Platelet	n.a.	Inhibition	=	84.2	%	PMID[555910]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	>	30000.0	nM	PMID[555911]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	26960.0	nM	PMID[555911]

☑ 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 NPC311936 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	499
0.1-0.2	2327
0.2-0.3	10310
0.3-0.4	7164
0.4-0.5	7083
0.5-0.6	12042
0.6-0.7	2845
0.7-0.8	393
0.8-0.85	13
0.85-0.9	3
0.9-0.95	10
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9939	High Similarity	NPC119579
0.9878	High Similarity	NPC28425
0.9756	High Similarity	NPC192939
0.9756	High Similarity	NPC215747
0.9755	High Similarity	NPC265383
0.9695	High Similarity	NPC260118
0.9467	High Similarity	NPC22928
0.9408	High Similarity	NPC219170
0.9408	High Similarity	NPC180253
0.9302	High Similarity	NPC294244
0.9298	High Similarity	NPC296742
0.9298	High Similarity	NPC112676
0.9294	High Similarity	NPC69213
0.929	High Similarity	NPC276060
0.924	High Similarity	NPC224293
0.8977	High Similarity	NPC29472
0.8689	High Similarity	NPC159101
0.8483	Intermediate Similarity	NPC320088
0.8475	Intermediate Similarity	NPC276674
0.8475	Intermediate Similarity	NPC33902
0.8373	Intermediate Similarity	NPC18614
0.8313	Intermediate Similarity	NPC52475
0.8284	Intermediate Similarity	NPC235628
0.8079	Intermediate Similarity	NPC285941
0.8045	Intermediate Similarity	NPC190461
0.8033	Intermediate Similarity	NPC474904
0.8023	Intermediate Similarity	NPC231371
0.8	Intermediate Similarity	NPC78284
0.7921	Intermediate Similarity	NPC168153
0.7912	Intermediate Similarity	NPC249405
0.7853	Intermediate Similarity	NPC158376
0.7853	Intermediate Similarity	NPC474931
0.7853	Intermediate Similarity	NPC145832
0.7853	Intermediate Similarity	NPC306555
0.7853	Intermediate Similarity	NPC12053
0.7853	Intermediate Similarity	NPC81218
0.7853	Intermediate Similarity	NPC117188
0.7853	Intermediate Similarity	NPC205421
0.7838	Intermediate Similarity	NPC312531
0.7797	Intermediate Similarity	NPC68328
0.7784	Intermediate Similarity	NPC1229
0.7784	Intermediate Similarity	NPC324144
0.7771	Intermediate Similarity	NPC27410
0.7771	Intermediate Similarity	NPC166014
0.7744	Intermediate Similarity	NPC90185
0.7744	Intermediate Similarity	NPC100573
0.7744	Intermediate Similarity	NPC207873
0.774	Intermediate Similarity	NPC477563
0.774	Intermediate Similarity	NPC13504
0.774	Intermediate Similarity	NPC306843
0.774	Intermediate Similarity	NPC136508
0.774	Intermediate Similarity	NPC253043
0.774	Intermediate Similarity	NPC78222
0.774	Intermediate Similarity	NPC212794
0.774	Intermediate Similarity	NPC196447
0.774	Intermediate Similarity	NPC96603
0.7733	Intermediate Similarity	NPC275027
0.768	Intermediate Similarity	NPC477020
0.768	Intermediate Similarity	NPC192135
0.768	Intermediate Similarity	NPC66341
0.7677	Intermediate Similarity	NPC91234
0.7656	Intermediate Similarity	NPC25897
0.765	Intermediate Similarity	NPC320223
0.765	Intermediate Similarity	NPC114364
0.7644	Intermediate Similarity	NPC17677
0.7632	Intermediate Similarity	NPC162653
0.7627	Intermediate Similarity	NPC60186
0.7614	Intermediate Similarity	NPC121510
0.7614	Intermediate Similarity	NPC171882
0.7614	Intermediate Similarity	NPC85661
0.7598	Intermediate Similarity	NPC476573
0.7598	Intermediate Similarity	NPC81247
0.7598	Intermediate Similarity	NPC35627
0.7586	Intermediate Similarity	NPC10730
0.7586	Intermediate Similarity	NPC10875
0.7569	Intermediate Similarity	NPC69712
0.7569	Intermediate Similarity	NPC477562
0.7569	Intermediate Similarity	NPC26240
0.7569	Intermediate Similarity	NPC168753
0.7569	Intermediate Similarity	NPC118274
0.7568	Intermediate Similarity	NPC179704
0.7563	Intermediate Similarity	NPC46679
0.7558	Intermediate Similarity	NPC77359
0.7544	Intermediate Similarity	NPC16436
0.7541	Intermediate Similarity	NPC199465
0.7541	Intermediate Similarity	NPC128560
0.7541	Intermediate Similarity	NPC229166
0.7527	Intermediate Similarity	NPC239775
0.7514	Intermediate Similarity	NPC329837
0.75	Intermediate Similarity	NPC287588
0.7488	Intermediate Similarity	NPC200888
0.7487	Intermediate Similarity	NPC135772
0.7486	Intermediate Similarity	NPC19555
0.7462	Intermediate Similarity	NPC304183
0.7459	Intermediate Similarity	NPC298979
0.7458	Intermediate Similarity	NPC476572
0.7436	Intermediate Similarity	NPC471489
0.7427	Intermediate Similarity	NPC122463
0.7427	Intermediate Similarity	NPC5462
0.7427	Intermediate Similarity	NPC118121
0.7426	Intermediate Similarity	NPC298449
0.7419	Intermediate Similarity	NPC474507
0.7411	Intermediate Similarity	NPC38961
0.7405	Intermediate Similarity	NPC148709
0.7405	Intermediate Similarity	NPC173416
0.7405	Intermediate Similarity	NPC476577
0.7402	Intermediate Similarity	NPC204446
0.7401	Intermediate Similarity	NPC291359
0.7396	Intermediate Similarity	NPC470090
0.7394	Intermediate Similarity	NPC228843
0.7391	Intermediate Similarity	NPC474051
0.7391	Intermediate Similarity	NPC228040
0.7389	Intermediate Similarity	NPC240684
0.738	Intermediate Similarity	NPC477561
0.738	Intermediate Similarity	NPC312918
0.738	Intermediate Similarity	NPC155442
0.738	Intermediate Similarity	NPC476574
0.7371	Intermediate Similarity	NPC326316
0.7371	Intermediate Similarity	NPC81733
0.7363	Intermediate Similarity	NPC310894
0.736	Intermediate Similarity	NPC195766
0.736	Intermediate Similarity	NPC206736
0.7351	Intermediate Similarity	NPC477558
0.7345	Intermediate Similarity	NPC99659
0.7345	Intermediate Similarity	NPC325871
0.7344	Intermediate Similarity	NPC302001
0.734	Intermediate Similarity	NPC116284
0.734	Intermediate Similarity	NPC290227
0.7337	Intermediate Similarity	NPC218131
0.7337	Intermediate Similarity	NPC105847
0.7337	Intermediate Similarity	NPC243759
0.733	Intermediate Similarity	NPC26601
0.7316	Intermediate Similarity	NPC477186
0.7314	Intermediate Similarity	NPC219383
0.7308	Intermediate Similarity	NPC257354
0.7308	Intermediate Similarity	NPC219341
0.7303	Intermediate Similarity	NPC186063
0.7294	Intermediate Similarity	NPC308768
0.7294	Intermediate Similarity	NPC12668
0.7292	Intermediate Similarity	NPC79213
0.7286	Intermediate Similarity	NPC261388
0.7283	Intermediate Similarity	NPC152212
0.7278	Intermediate Similarity	NPC151656
0.7278	Intermediate Similarity	NPC230919
0.7278	Intermediate Similarity	NPC200935
0.7278	Intermediate Similarity	NPC266453
0.7268	Intermediate Similarity	NPC210140
0.7268	Intermediate Similarity	NPC247389
0.7262	Intermediate Similarity	NPC126637
0.7257	Intermediate Similarity	NPC103379
0.7257	Intermediate Similarity	NPC477565
0.7253	Intermediate Similarity	NPC225774
0.725	Intermediate Similarity	NPC193777
0.7249	Intermediate Similarity	NPC248642
0.7246	Intermediate Similarity	NPC218530
0.7245	Intermediate Similarity	NPC212163
0.7241	Intermediate Similarity	NPC179825
0.7241	Intermediate Similarity	NPC321505
0.7241	Intermediate Similarity	NPC191376
0.7238	Intermediate Similarity	NPC24954
0.7236	Intermediate Similarity	NPC156728
0.7236	Intermediate Similarity	NPC244606
0.7235	Intermediate Similarity	NPC243996
0.7235	Intermediate Similarity	NPC132804
0.7235	Intermediate Similarity	NPC275061
0.7235	Intermediate Similarity	NPC220344
0.7234	Intermediate Similarity	NPC126284
0.7229	Intermediate Similarity	NPC130595
0.7229	Intermediate Similarity	NPC93882
0.7216	Intermediate Similarity	NPC184161
0.7213	Intermediate Similarity	NPC476432
0.7213	Intermediate Similarity	NPC90984
0.7213	Intermediate Similarity	NPC24264
0.7211	Intermediate Similarity	NPC156576
0.7209	Intermediate Similarity	NPC175838
0.7207	Intermediate Similarity	NPC170503
0.7207	Intermediate Similarity	NPC203784
0.7207	Intermediate Similarity	NPC126519
0.7202	Intermediate Similarity	NPC114335
0.7202	Intermediate Similarity	NPC141915
0.7202	Intermediate Similarity	NPC280964
0.72	Intermediate Similarity	NPC24233
0.72	Intermediate Similarity	NPC147390
0.72	Intermediate Similarity	NPC135538
0.72	Intermediate Similarity	NPC246587
0.72	Intermediate Similarity	NPC428
0.72	Intermediate Similarity	NPC476571
0.7196	Intermediate Similarity	NPC473182
0.7192	Intermediate Similarity	NPC61731
0.7192	Intermediate Similarity	NPC186569
0.7188	Intermediate Similarity	NPC186546
0.7188	Intermediate Similarity	NPC476576
0.7186	Intermediate Similarity	NPC313737
0.7186	Intermediate Similarity	NPC6854
0.7186	Intermediate Similarity	NPC285078
0.7182	Intermediate Similarity	NPC477559
0.7182	Intermediate Similarity	NPC266753
0.7182	Intermediate Similarity	NPC160298
0.7182	Intermediate Similarity	NPC232924
0.7182	Intermediate Similarity	NPC306902

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 NPC311936 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	802
0.2-0.3	963
0.3-0.4	1970
0.4-0.5	2610
0.5-0.6	1984
0.6-0.7	455
0.7-0.8	32
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7733	Intermediate Similarity	NPD5617	Suspended
0.7569	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2883	Discontinued
0.7389	Intermediate Similarity	NPD1850	Phase 3
0.7371	Intermediate Similarity	NPD5811	Approved
0.7363	Intermediate Similarity	NPD4083	Discontinued
0.736	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD3778	Approved
0.7278	Intermediate Similarity	NPD3453	Discontinued
0.7258	Intermediate Similarity	NPD3920	Phase 2
0.7229	Intermediate Similarity	NPD2674	Phase 3
0.7219	Intermediate Similarity	NPD6184	Discontinued
0.7191	Intermediate Similarity	NPD2789	Approved
0.7188	Intermediate Similarity	NPD2843	Phase 2
0.7188	Intermediate Similarity	NPD2845	Phase 2
0.7135	Intermediate Similarity	NPD27	Approved
0.7135	Intermediate Similarity	NPD2489	Approved
0.7135	Intermediate Similarity	NPD3296	Phase 1
0.7135	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3237	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3236	Phase 3
0.7086	Intermediate Similarity	NPD2420	Approved
0.7086	Intermediate Similarity	NPD2421	Approved
0.7083	Intermediate Similarity	NPD4951	Discontinued
0.7074	Intermediate Similarity	NPD7479	Phase 2
0.7072	Intermediate Similarity	NPD5599	Discontinued
0.7066	Intermediate Similarity	NPD3145	Approved
0.7066	Intermediate Similarity	NPD3144	Approved
0.7062	Intermediate Similarity	NPD5641	Discontinued
0.7056	Intermediate Similarity	NPD3812	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD677	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3051	Approved
0.7022	Intermediate Similarity	NPD4003	Phase 3
0.7022	Intermediate Similarity	NPD950	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5810	Discontinued
0.7005	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4055	Discovery
0.699	Remote Similarity	NPD7262	Phase 1
0.6989	Remote Similarity	NPD2970	Approved
0.6989	Remote Similarity	NPD2969	Approved
0.6983	Remote Similarity	NPD4005	Discontinued
0.6974	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD2821	Approved
0.6959	Remote Similarity	NPD7906	Approved
0.6952	Remote Similarity	NPD3763	Approved
0.6949	Remote Similarity	NPD4123	Phase 3
0.6935	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4578	Approved
0.6927	Remote Similarity	NPD4577	Approved
0.6914	Remote Similarity	NPD6331	Phase 2
0.691	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4097	Suspended
0.6884	Remote Similarity	NPD7034	Discontinued
0.6882	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3301	Approved
0.6875	Remote Similarity	NPD5241	Discontinued
0.6872	Remote Similarity	NPD3349	Phase 2
0.6872	Remote Similarity	NPD5800	Discontinued
0.6872	Remote Similarity	NPD3398	Discontinued
0.6863	Remote Similarity	NPD5530	Phase 1
0.6862	Remote Similarity	NPD2898	Approved
0.6859	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3922	Approved
0.6853	Remote Similarity	NPD3923	Approved
0.6853	Remote Similarity	NPD3921	Approved
0.6853	Remote Similarity	NPD3924	Approved
0.6853	Remote Similarity	NPD3963	Phase 1
0.6839	Remote Similarity	NPD7313	Approved
0.6839	Remote Similarity	NPD7311	Approved
0.6839	Remote Similarity	NPD7310	Approved
0.6839	Remote Similarity	NPD7312	Approved
0.6829	Remote Similarity	NPD7263	Phase 2
0.6828	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4663	Approved
0.6818	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD7831	Phase 2
0.6811	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD7833	Phase 2
0.6804	Remote Similarity	NPD8054	Approved
0.6804	Remote Similarity	NPD8053	Approved
0.6804	Remote Similarity	NPD7309	Approved
0.68	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6612	Phase 2
0.6782	Remote Similarity	NPD2161	Phase 2
0.676	Remote Similarity	NPD4584	Approved
0.6758	Remote Similarity	NPD4675	Approved
0.6758	Remote Similarity	NPD4678	Approved
0.6757	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD1669	Approved
0.6739	Remote Similarity	NPD5929	Approved
0.6738	Remote Similarity	NPD6037	Discontinued
0.6727	Remote Similarity	NPD6494	Phase 2
0.6723	Remote Similarity	NPD5819	Phase 2
0.6717	Remote Similarity	NPD2490	Approved
0.6717	Remote Similarity	NPD2488	Approved
0.6716	Remote Similarity	NPD4605	Approved
0.6716	Remote Similarity	NPD4604	Approved
0.6716	Remote Similarity	NPD6527	Approved
0.67	Remote Similarity	NPD7686	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4502	Phase 2
0.6698	Remote Similarity	NPD5164	Discontinued
0.6686	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1558	Phase 1
0.6667	Remote Similarity	NPD3342	Phase 2
0.6667	Remote Similarity	NPD7546	Discontinued
0.665	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7125	Discontinued
0.6649	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD3845	Phase 1
0.6636	Remote Similarity	NPD8067	Phase 3
0.6634	Remote Similarity	NPD3516	Approved
0.6634	Remote Similarity	NPD3515	Approved
0.6628	Remote Similarity	NPD7477	Discontinued
0.6617	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD2560	Approved
0.6613	Remote Similarity	NPD3557	Approved
0.6613	Remote Similarity	NPD3560	Approved
0.6613	Remote Similarity	NPD2563	Approved
0.6613	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD3558	Approved
0.6613	Remote Similarity	NPD6063	Approved
0.6613	Remote Similarity	NPD3556	Approved
0.6611	Remote Similarity	NPD4357	Discontinued
0.6599	Remote Similarity	NPD6340	Approved
0.6599	Remote Similarity	NPD6339	Approved
0.6593	Remote Similarity	NPD6030	Approved
0.6593	Remote Similarity	NPD6031	Approved
0.659	Remote Similarity	NPD3620	Phase 2
0.659	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3816	Phase 1
0.6588	Remote Similarity	NPD3815	Phase 1
0.6587	Remote Similarity	NPD5429	Discontinued
0.6587	Remote Similarity	NPD7453	Approved
0.6587	Remote Similarity	NPD7222	Phase 2
0.6587	Remote Similarity	NPD7452	Approved
0.6582	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4010	Discontinued
0.6577	Remote Similarity	NPD7922	Phase 1
0.6573	Remote Similarity	NPD8149	Discontinued
0.657	Remote Similarity	NPD5111	Phase 2
0.657	Remote Similarity	NPD5110	Phase 2
0.657	Remote Similarity	NPD5109	Approved
0.6567	Remote Similarity	NPD6526	Approved
0.6562	Remote Similarity	NPD5938	Phase 3
0.6556	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5658	Approved
0.6554	Remote Similarity	NPD1375	Discontinued
0.6545	Remote Similarity	NPD2216	Approved
0.6545	Remote Similarity	NPD2215	Approved
0.6543	Remote Similarity	NPD5604	Discontinued
0.6543	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.654	Remote Similarity	NPD5936	Approved
0.654	Remote Similarity	NPD5939	Approved
0.6538	Remote Similarity	NPD4319	Phase 2
0.6536	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD3634	Approved
0.6517	Remote Similarity	NPD7153	Discontinued
0.6517	Remote Similarity	NPD3633	Approved
0.651	Remote Similarity	NPD4481	Phase 3
0.6509	Remote Similarity	NPD7225	Discontinued
0.6505	Remote Similarity	NPD3450	Approved
0.6505	Remote Similarity	NPD2494	Approved
0.6505	Remote Similarity	NPD3452	Approved
0.6505	Remote Similarity	NPD2493	Approved
0.6502	Remote Similarity	NPD5582	Discontinued
0.6502	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD6723	Discontinued
0.65	Remote Similarity	NPD3692	Discontinued
0.65	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD6071	Discontinued
0.6489	Remote Similarity	NPD7773	Phase 2
0.6486	Remote Similarity	NPD6502	Phase 2
0.6484	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4859	Phase 1
0.6474	Remote Similarity	NPD2322	Discovery
0.6473	Remote Similarity	NPD6975	Discontinued
0.6471	Remote Similarity	NPD2978	Approved
0.6471	Remote Similarity	NPD2977	Approved
0.6458	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD3290	Approved
0.6456	Remote Similarity	NPD3289	Phase 3

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