NPASS Compound

Structure

CID246974 OpenBabel06191716052D 22 23 0 0 0 0 0 0 0 0999 V2000 11.3434 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4773 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 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 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 1.8171 -0.1910 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 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4773 -1.1910 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 21 1 0 0 0 0 13 22 1 0 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 19 2 3 0 0 0 18 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	303.18
Volume:	326.956
LogP:	4.315
LogD:	4.017
LogS:	-4.382
# Rotatable Bonds:	9
TPSA:	47.56
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.591
Synthetic Accessibility Score:	2.263
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.66
MDCK Permeability:	2.7344896807335317e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.435
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.346
Plasma Protein Binding (PPB):	97.52970123291016%
Volume Distribution (VD):	1.522
Pgp-substrate:	2.4871439933776855%

ADMET: Metabolism

CYP1A2-inhibitor:	0.937
CYP1A2-substrate:	0.265
CYP2C19-inhibitor:	0.963
CYP2C19-substrate:	0.594
CYP2C9-inhibitor:	0.851
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.936
CYP2D6-substrate:	0.871
CYP3A4-inhibitor:	0.948
CYP3A4-substrate:	0.208

ADMET: Excretion

Clearance (CL):	12.608
Half-life (T1/2):	0.434

ADMET: Toxicity

hERG Blockers:	0.306
Human Hepatotoxicity (H-HT):	0.356
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.525
Skin Sensitization:	0.945
Carcinogencity:	0.72
Eye Corrosion:	0.035
Eye Irritation:	0.479
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC246974

Natural Product ID:	NPC246974
*Common Name:**	Pipercallosidine
IUPAC Name:	(E)-7-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)hept-2-enamide
Synonyms:	Pipercallosidine
Standard InCHIKey:	PWLZXPUSJOUTMB-SOFGYWHQSA-N
Standard InCHI:	InChI=1S/C18H25NO3/c1-14(2)12-19-18(20)8-6-4-3-5-7-15-9-10-16-17(11-15)22-13-21-16/h6,8-11,14H,3-5,7,12-13H2,1-2H3,(H,19,20)/b8-6+
SMILES:	CC(CN=C(/C=C/CCCCc1ccc2c(c1)OCO2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL226637
PubChem CID:	5372065
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
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17243725]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	whole plants	Sendai, Miyagi Prefecture, Japan	2000-Sep	PMID[17243725]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17397219]
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]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	Kego Nature Reserve, Hatinh Province, Vietnam	2008-DEC	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	twig	n.a.	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	aerial parts	Kego Nature Reserve, Hatinh Province, Vietnam	2008-DEC	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	stem	n.a.	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	inflorescence	n.a.	PMID[21973101]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22940450]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	leaves, twigs, and fruits	Nui Chua National Park (11 43' N; 109 08' E; 730 m alt.), Ninh Thuan Province, Vietnam	2010-Jan	PMID[23301897]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31621322]
NPO2846	Piper sarmentosum	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]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1912	Acanthosyris paulo-alvinii	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6614	Rubus pileatus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO61	Phoebe grandis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO992	Betula alnoides	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5657	Oocystis polymorpha	Species	Oocystaceae	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	11

Activity Type	# Activity
Cell Line	10
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[459650]
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[459650]
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[459650]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[459651]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[459651]
NPT133	Cell Line	ZR-75-1	Homo sapiens	IC50	>	40000.0	nM	PMID[459651]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	40000.0	nM	PMID[459651]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	40000.0	nM	PMID[459651]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	40000.0	nM	PMID[459651]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	40000.0	nM	PMID[459651]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	40000.0	nM	PMID[459651]

☑ 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 NPC246974 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	165
0.1-0.2	1362
0.2-0.3	5711
0.3-0.4	13021
0.4-0.5	5344
0.5-0.6	10988
0.6-0.7	4871
0.7-0.8	1159
0.8-0.85	50
0.85-0.9	10
0.9-0.95	0
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC147247
0.9917	High Similarity	NPC157740
0.9917	High Similarity	NPC99798
0.9835	High Similarity	NPC156944
0.9754	High Similarity	NPC41331
0.9754	High Similarity	NPC291449
0.9752	High Similarity	NPC152186
0.9752	High Similarity	NPC170583
0.9752	High Similarity	NPC71105
0.9752	High Similarity	NPC182147
0.9752	High Similarity	NPC246133
0.9752	High Similarity	NPC207541
0.9672	High Similarity	NPC251466
0.9669	High Similarity	NPC300955
0.9593	High Similarity	NPC191302
0.9134	High Similarity	NPC470706
0.9055	High Similarity	NPC469977
0.9	High Similarity	NPC473463
0.9	High Similarity	NPC284855
0.9	High Similarity	NPC282477
0.8881	High Similarity	NPC275150
0.875	High Similarity	NPC301713
0.8682	High Similarity	NPC153990
0.8661	High Similarity	NPC249788
0.8657	High Similarity	NPC254610
0.8623	High Similarity	NPC327623
0.8521	High Similarity	NPC474560
0.8512	High Similarity	NPC166837
0.8492	Intermediate Similarity	NPC344161
0.8473	Intermediate Similarity	NPC155838
0.8462	Intermediate Similarity	NPC274356
0.8433	Intermediate Similarity	NPC218530
0.843	Intermediate Similarity	NPC31279
0.8421	Intermediate Similarity	NPC214869
0.8409	Intermediate Similarity	NPC52029
0.8409	Intermediate Similarity	NPC195749
0.8409	Intermediate Similarity	NPC35961
0.8397	Intermediate Similarity	NPC186898
0.8359	Intermediate Similarity	NPC80241
0.8359	Intermediate Similarity	NPC301641
0.8347	Intermediate Similarity	NPC127326
0.8346	Intermediate Similarity	NPC114102
0.8284	Intermediate Similarity	NPC93882
0.8284	Intermediate Similarity	NPC130595
0.8261	Intermediate Similarity	NPC77572
0.8258	Intermediate Similarity	NPC251571
0.8222	Intermediate Similarity	NPC6854
0.8222	Intermediate Similarity	NPC285078
0.8222	Intermediate Similarity	NPC313737
0.8209	Intermediate Similarity	NPC308885
0.8209	Intermediate Similarity	NPC275950
0.8209	Intermediate Similarity	NPC255550
0.8182	Intermediate Similarity	NPC40352
0.8182	Intermediate Similarity	NPC213711
0.8148	Intermediate Similarity	NPC476345
0.8116	Intermediate Similarity	NPC14600
0.8116	Intermediate Similarity	NPC204848
0.8116	Intermediate Similarity	NPC160607
0.8116	Intermediate Similarity	NPC41473
0.8116	Intermediate Similarity	NPC312770
0.8106	Intermediate Similarity	NPC17348
0.8088	Intermediate Similarity	NPC227002
0.8088	Intermediate Similarity	NPC147616
0.8088	Intermediate Similarity	NPC104077
0.8088	Intermediate Similarity	NPC219671
0.8088	Intermediate Similarity	NPC471505
0.8088	Intermediate Similarity	NPC259742
0.8088	Intermediate Similarity	NPC106739
0.8074	Intermediate Similarity	NPC173308
0.8074	Intermediate Similarity	NPC63574
0.8074	Intermediate Similarity	NPC181079
0.8058	Intermediate Similarity	NPC299583
0.8029	Intermediate Similarity	NPC169973
0.8	Intermediate Similarity	NPC183262
0.7986	Intermediate Similarity	NPC95366
0.7986	Intermediate Similarity	NPC248505
0.7985	Intermediate Similarity	NPC158737
0.7985	Intermediate Similarity	NPC177167
0.7985	Intermediate Similarity	NPC64948
0.7984	Intermediate Similarity	NPC281298
0.7984	Intermediate Similarity	NPC69670
0.7984	Intermediate Similarity	NPC310338
0.7984	Intermediate Similarity	NPC57501
0.7984	Intermediate Similarity	NPC119949
0.7984	Intermediate Similarity	NPC137685
0.7969	Intermediate Similarity	NPC164386
0.7956	Intermediate Similarity	NPC97316
0.7955	Intermediate Similarity	NPC317769
0.7955	Intermediate Similarity	NPC31344
0.7953	Intermediate Similarity	NPC303370
0.7941	Intermediate Similarity	NPC134764
0.7941	Intermediate Similarity	NPC171550
0.7941	Intermediate Similarity	NPC184814
0.7939	Intermediate Similarity	NPC114845
0.7937	Intermediate Similarity	NPC165106
0.7934	Intermediate Similarity	NPC292792
0.7929	Intermediate Similarity	NPC296898
0.7926	Intermediate Similarity	NPC57119
0.7926	Intermediate Similarity	NPC158471
0.7926	Intermediate Similarity	NPC226862
0.7926	Intermediate Similarity	NPC165128
0.7923	Intermediate Similarity	NPC232316
0.7923	Intermediate Similarity	NPC227217
0.7923	Intermediate Similarity	NPC117780
0.7923	Intermediate Similarity	NPC165133
0.7923	Intermediate Similarity	NPC242885
0.7923	Intermediate Similarity	NPC95614
0.7923	Intermediate Similarity	NPC56214
0.792	Intermediate Similarity	NPC257124
0.792	Intermediate Similarity	NPC8547
0.792	Intermediate Similarity	NPC173746
0.792	Intermediate Similarity	NPC156840
0.7914	Intermediate Similarity	NPC137172
0.7914	Intermediate Similarity	NPC145446
0.7914	Intermediate Similarity	NPC184938
0.7914	Intermediate Similarity	NPC142547
0.7914	Intermediate Similarity	NPC135777
0.7914	Intermediate Similarity	NPC174191
0.7914	Intermediate Similarity	NPC101624
0.7907	Intermediate Similarity	NPC474040
0.7907	Intermediate Similarity	NPC470626
0.7899	Intermediate Similarity	NPC196937
0.7886	Intermediate Similarity	NPC227894
0.7883	Intermediate Similarity	NPC318862
0.7868	Intermediate Similarity	NPC476748
0.7857	Intermediate Similarity	NPC470707
0.7857	Intermediate Similarity	NPC193528
0.7857	Intermediate Similarity	NPC252107
0.7857	Intermediate Similarity	NPC165646
0.7852	Intermediate Similarity	NPC100129
0.7846	Intermediate Similarity	NPC311595
0.7846	Intermediate Similarity	NPC43275
0.7846	Intermediate Similarity	NPC24474
0.7842	Intermediate Similarity	NPC96406
0.7842	Intermediate Similarity	NPC264956
0.7836	Intermediate Similarity	NPC85830
0.7829	Intermediate Similarity	NPC120075
0.7829	Intermediate Similarity	NPC212643
0.7829	Intermediate Similarity	NPC199209
0.7829	Intermediate Similarity	NPC33271
0.7829	Intermediate Similarity	NPC293619
0.782	Intermediate Similarity	NPC140359
0.782	Intermediate Similarity	NPC13020
0.7817	Intermediate Similarity	NPC195814
0.7812	Intermediate Similarity	NPC47194
0.7812	Intermediate Similarity	NPC475815
0.7812	Intermediate Similarity	NPC473264
0.781	Intermediate Similarity	NPC477705
0.781	Intermediate Similarity	NPC233224
0.781	Intermediate Similarity	NPC271208
0.781	Intermediate Similarity	NPC477694
0.7803	Intermediate Similarity	NPC160380
0.7803	Intermediate Similarity	NPC38996
0.7786	Intermediate Similarity	NPC18576
0.7786	Intermediate Similarity	NPC263835
0.7786	Intermediate Similarity	NPC471308
0.7786	Intermediate Similarity	NPC160120
0.7786	Intermediate Similarity	NPC99078
0.7786	Intermediate Similarity	NPC289330
0.7786	Intermediate Similarity	NPC17388
0.7786	Intermediate Similarity	NPC53596
0.7778	Intermediate Similarity	NPC473960
0.7778	Intermediate Similarity	NPC55300
0.777	Intermediate Similarity	NPC45783
0.777	Intermediate Similarity	NPC193673
0.777	Intermediate Similarity	NPC94280
0.777	Intermediate Similarity	NPC103947
0.777	Intermediate Similarity	NPC471390
0.777	Intermediate Similarity	NPC471391
0.777	Intermediate Similarity	NPC159150
0.777	Intermediate Similarity	NPC328419
0.777	Intermediate Similarity	NPC112237
0.7769	Intermediate Similarity	NPC310905
0.7769	Intermediate Similarity	NPC12714
0.7769	Intermediate Similarity	NPC474214
0.776	Intermediate Similarity	NPC246358
0.776	Intermediate Similarity	NPC233731
0.776	Intermediate Similarity	NPC36108
0.776	Intermediate Similarity	NPC7097
0.7755	Intermediate Similarity	NPC77359
0.7754	Intermediate Similarity	NPC192255
0.7754	Intermediate Similarity	NPC82111
0.7754	Intermediate Similarity	NPC227160
0.7754	Intermediate Similarity	NPC118419
0.7754	Intermediate Similarity	NPC477706
0.7752	Intermediate Similarity	NPC9341
0.7752	Intermediate Similarity	NPC111225
0.7752	Intermediate Similarity	NPC81067
0.7746	Intermediate Similarity	NPC123526
0.7746	Intermediate Similarity	NPC193666
0.7746	Intermediate Similarity	NPC88640
0.7744	Intermediate Similarity	NPC256167
0.7744	Intermediate Similarity	NPC471314
0.7744	Intermediate Similarity	NPC471315
0.7744	Intermediate Similarity	NPC298486
0.7744	Intermediate Similarity	NPC30462
0.7744	Intermediate Similarity	NPC85488
0.774	Intermediate Similarity	NPC16436
0.7737	Intermediate Similarity	NPC228769
0.7737	Intermediate Similarity	NPC470633

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 NPC246974 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	795
0.2-0.3	1238
0.3-0.4	2510
0.4-0.5	2375
0.5-0.6	1385
0.6-0.7	619
0.7-0.8	86
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8284	Intermediate Similarity	NPD2674	Phase 3
0.8268	Intermediate Similarity	NPD1357	Approved
0.8209	Intermediate Similarity	NPD3145	Approved
0.8209	Intermediate Similarity	NPD3144	Approved
0.8188	Intermediate Similarity	NPD2161	Phase 2
0.8041	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1375	Discontinued
0.7986	Intermediate Similarity	NPD4108	Discontinued
0.7958	Intermediate Similarity	NPD6331	Phase 2
0.7939	Intermediate Similarity	NPD3705	Approved
0.7937	Intermediate Similarity	NPD5283	Phase 1
0.792	Intermediate Similarity	NPD228	Approved
0.7895	Intermediate Similarity	NPD2922	Phase 1
0.7883	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4739	Approved
0.7852	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD3685	Discontinued
0.782	Intermediate Similarity	NPD1669	Approved
0.781	Intermediate Similarity	NPD5109	Approved
0.781	Intermediate Similarity	NPD5111	Phase 2
0.781	Intermediate Similarity	NPD5110	Phase 2
0.7778	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD1712	Approved
0.7714	Intermediate Similarity	NPD2157	Approved
0.7714	Intermediate Similarity	NPD2492	Phase 1
0.7692	Intermediate Similarity	NPD7153	Discontinued
0.7687	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD776	Approved
0.7647	Intermediate Similarity	NPD5604	Discontinued
0.7603	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7526	Approved
0.7568	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD52	Approved
0.7538	Intermediate Similarity	NPD709	Approved
0.7536	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD2668	Approved
0.7519	Intermediate Similarity	NPD2667	Approved
0.7482	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD2232	Approved
0.7481	Intermediate Similarity	NPD2230	Approved
0.7481	Intermediate Similarity	NPD2233	Approved
0.7451	Intermediate Similarity	NPD2978	Approved
0.7451	Intermediate Similarity	NPD2977	Approved
0.745	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD821	Approved
0.7429	Intermediate Similarity	NPD5718	Phase 2
0.7419	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD2219	Phase 1
0.7413	Intermediate Similarity	NPD6895	Approved
0.7413	Intermediate Similarity	NPD6896	Approved
0.7402	Intermediate Similarity	NPD2684	Approved
0.7397	Intermediate Similarity	NPD4237	Approved
0.7397	Intermediate Similarity	NPD4236	Phase 3
0.7391	Intermediate Similarity	NPD6584	Phase 3
0.7383	Intermediate Similarity	NPD4123	Phase 3
0.7361	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD2653	Approved
0.7338	Intermediate Similarity	NPD5772	Approved
0.7338	Intermediate Similarity	NPD5773	Approved
0.7324	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1558	Phase 1
0.7315	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6111	Discontinued
0.7285	Intermediate Similarity	NPD2122	Discontinued
0.7279	Intermediate Similarity	NPD5177	Phase 3
0.7279	Intermediate Similarity	NPD3060	Approved
0.7234	Intermediate Similarity	NPD3027	Phase 3
0.723	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4110	Phase 3
0.7222	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4097	Suspended
0.7211	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2808	Discontinued
0.7203	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3620	Phase 2
0.72	Intermediate Similarity	NPD4357	Discontinued
0.719	Intermediate Similarity	NPD4005	Discontinued
0.7181	Intermediate Similarity	NPD5241	Discontinued
0.7179	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7843	Approved
0.7174	Intermediate Similarity	NPD6582	Phase 2
0.7174	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6583	Phase 3
0.7164	Intermediate Similarity	NPD5536	Phase 2
0.7162	Intermediate Similarity	NPD4162	Approved
0.7152	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4675	Approved
0.7143	Intermediate Similarity	NPD7157	Approved
0.7143	Intermediate Similarity	NPD4678	Approved
0.7133	Intermediate Similarity	NPD839	Approved
0.7133	Intermediate Similarity	NPD840	Approved
0.7132	Intermediate Similarity	NPD4626	Approved
0.7124	Intermediate Similarity	NPD4210	Discontinued
0.7113	Intermediate Similarity	NPD1024	Discontinued
0.7103	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2235	Phase 2
0.7101	Intermediate Similarity	NPD2231	Phase 2
0.7097	Intermediate Similarity	NPD5089	Approved
0.7097	Intermediate Similarity	NPD5090	Approved
0.7095	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD4993	Discontinued
0.7092	Intermediate Similarity	NPD2040	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3596	Phase 2
0.7083	Intermediate Similarity	NPD2238	Phase 2
0.7077	Intermediate Similarity	NPD3021	Approved
0.7077	Intermediate Similarity	NPD3022	Approved
0.7063	Intermediate Similarity	NPD1048	Approved
0.7063	Intermediate Similarity	NPD1039	Discontinued
0.7032	Intermediate Similarity	NPD1642	Discontinued
0.7032	Intermediate Similarity	NPD7028	Phase 2
0.702	Intermediate Similarity	NPD7124	Phase 2
0.7014	Intermediate Similarity	NPD1423	Approved
0.7014	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3687	Approved
0.7013	Intermediate Similarity	NPD3686	Approved
0.6993	Remote Similarity	NPD3164	Approved
0.6993	Remote Similarity	NPD3166	Approved
0.6993	Remote Similarity	NPD3165	Approved
0.6993	Remote Similarity	NPD3167	Approved
0.6985	Remote Similarity	NPD6580	Approved
0.6985	Remote Similarity	NPD6581	Approved
0.6981	Remote Similarity	NPD4055	Discovery
0.698	Remote Similarity	NPD7037	Approved
0.6977	Remote Similarity	NPD1445	Approved
0.6977	Remote Similarity	NPD1444	Approved
0.6968	Remote Similarity	NPD3111	Phase 1
0.6962	Remote Similarity	NPD2563	Approved
0.6962	Remote Similarity	NPD2560	Approved
0.6957	Remote Similarity	NPD3847	Discontinued
0.695	Remote Similarity	NPD1820	Approved
0.695	Remote Similarity	NPD1819	Approved
0.695	Remote Similarity	NPD1818	Approved
0.695	Remote Similarity	NPD1817	Approved
0.6943	Remote Similarity	NPD37	Approved
0.6943	Remote Similarity	NPD5722	Discontinued
0.6939	Remote Similarity	NPD7119	Phase 2
0.6934	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2983	Phase 2
0.6929	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2982	Phase 2
0.6928	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3657	Discovery
0.6917	Remote Similarity	NPD9379	Approved
0.6917	Remote Similarity	NPD9377	Approved
0.6917	Remote Similarity	NPD1138	Approved
0.6913	Remote Similarity	NPD3656	Approved
0.6901	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3163	Approved
0.6897	Remote Similarity	NPD7477	Discontinued
0.6897	Remote Similarity	NPD3162	Approved
0.6894	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6387	Discontinued
0.6889	Remote Similarity	NPD6671	Approved
0.6889	Remote Similarity	NPD2557	Approved
0.6879	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7833	Phase 2
0.6875	Remote Similarity	NPD7831	Phase 2
0.6875	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4083	Discontinued
0.6867	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2229	Approved
0.6866	Remote Similarity	NPD2234	Approved
0.6866	Remote Similarity	NPD2228	Approved
0.6861	Remote Similarity	NPD1182	Approved
0.6857	Remote Similarity	NPD2981	Phase 2
0.6857	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2237	Approved
0.6853	Remote Similarity	NPD3018	Phase 2
0.6849	Remote Similarity	NPD4060	Phase 1
0.6846	Remote Similarity	NPD3134	Approved
0.6846	Remote Similarity	NPD6032	Approved
0.6842	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1139	Approved
0.6842	Remote Similarity	NPD1137	Approved
0.6839	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6674	Discontinued
0.6818	Remote Similarity	NPD3146	Approved
0.6818	Remote Similarity	NPD556	Approved
0.6818	Remote Similarity	NPD1792	Phase 2
0.6818	Remote Similarity	NPD4584	Approved
0.6818	Remote Similarity	NPD5451	Approved
0.6818	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4967	Phase 2
0.6813	Remote Similarity	NPD4966	Approved
0.6813	Remote Similarity	NPD4965	Approved
0.6812	Remote Similarity	NPD3445	Approved
0.6812	Remote Similarity	NPD3443	Approved
0.6812	Remote Similarity	NPD5691	Approved
0.6812	Remote Similarity	NPD3444	Approved
0.6805	Remote Similarity	NPD7280	Phase 3
0.6805	Remote Similarity	NPD7281	Phase 3
0.6795	Remote Similarity	NPD2883	Discontinued
0.6794	Remote Similarity	NPD1358	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