NPASS Compound

Structure

CID106786 OpenBabel06191715452D 25 28 0 0 0 0 0 0 0 0999 V2000 8.1010 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5029 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3690 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6369 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5029 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6369 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9049 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9049 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3690 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5029 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7709 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7709 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3690 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6369 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2350 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0388 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0388 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2350 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5029 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.1010 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1010 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 -0.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 -2.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7028 3.0929 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 3 2 0 0 0 0 2 11 1 0 0 0 0 3 16 1 0 0 0 0 4 5 1 0 0 0 0 4 12 1 0 0 0 0 5 20 1 0 0 0 0 6 11 2 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 14 1 0 0 0 0 9 20 2 0 0 0 0 10 23 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 12 13 1 0 0 0 0 13 15 1 0 0 0 0 14 19 2 0 0 0 0 15 20 2 0 0 0 0 16 19 1 0 0 0 0 16 21 2 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	351.17
Volume:	347.407
LogP:	0.796
LogD:	1.075
LogS:	-1.637
# Rotatable Bonds:	1
TPSA:	96.3
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.395
Synthetic Accessibility Score:	5.214
Fsp3:	0.667
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:	-4.846
MDCK Permeability:	6.975371798034757e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.773
30% Bioavailability (F30%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.321
Plasma Protein Binding (PPB):	37.95256805419922%
Volume Distribution (VD):	1.017
Pgp-substrate:	54.08723831176758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.07
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.308
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.22
CYP2D6-substrate:	0.253
CYP3A4-inhibitor:	0.185
CYP3A4-substrate:	0.315

ADMET: Excretion

Clearance (CL):	4.998
Half-life (T1/2):	0.731

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.338
Drug-inuced Liver Injury (DILI):	0.714
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.753
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.165
Carcinogencity:	0.962
Eye Corrosion:	0.004
Eye Irritation:	0.028
Respiratory Toxicity:	0.664

Download Data

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

Natural Product: NPC106786

Natural Product ID:	NPC106786
*Common Name:**	Thalifendine
IUPAC Name:	n.a.
Synonyms:	Thalifendine; Thalifendine Chloride
Standard InCHIKey:	QKDAYMOWDPMRHC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H15NO4.ClH/c1-22-19-14-9-20-5-4-12-7-17-18(24-10-23-17)8-13(12)15(20)6-11(14)2-3-16(19)21;/h2-3,6-9H,4-5,10H2,1H3;1H
SMILES:	COC1=C2C=N3=C(C=C2C=CC1=O)c1cc2c(cc1CC3)OCO2.Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491544
PubChem CID:	5321913
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001909] Protoberberine alkaloids and derivatives

*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
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[11000020]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	tubers	n.a.	n.a.	PMID[20594848]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21401114]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28050	Thalictrum podocarpum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13508	Thalictrum honanenae	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22553	Thalictrum fendleri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28050	Thalictrum podocarpum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13508	Thalictrum honanenae	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22553	Thalictrum fendleri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29008	Coptis teeta	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26538	Phellodendron chinese	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28050	Thalictrum podocarpum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22553	Thalictrum fendleri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29008	Coptis teeta	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13757	Coptis japonica	Species	Ranunculaceae	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	7
Others	3

Activity Type	# Activity
Cell Line	7
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	699000.0	nM	PMID[540494]
NPT65	Cell Line	HepG2	Homo sapiens	FC	=	1.6	n.a.	PMID[540495]
NPT65	Cell Line	HepG2	Homo sapiens	FC	=	1.7	n.a.	PMID[540495]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	28260.0	nM	PMID[540496]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	30000.0	nM	PMID[540496]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	25670.0	nM	PMID[540496]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	>	30000.0	nM	PMID[540496]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	7910.0	nM	PMID[540494]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	116000.0	nM	PMID[540494]
NPT27	Others	Unspecified		Drugexcretion	=	83.0	%	PMID[540497]

☑ 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 NPC106786 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score	Similarity Level	Natural Product ID
0.9801	High Similarity	NPC59567
0.9463	High Similarity	NPC476579
0.9139	High Similarity	NPC223125
0.9108	High Similarity	NPC306669
0.902	High Similarity	NPC223124
0.8903	High Similarity	NPC216459
0.8903	High Similarity	NPC138487
0.8903	High Similarity	NPC41178
0.8896	High Similarity	NPC233029
0.8896	High Similarity	NPC210148
0.8882	High Similarity	NPC475959
0.8846	High Similarity	NPC146288
0.8774	High Similarity	NPC476580
0.8773	High Similarity	NPC4669
0.875	High Similarity	NPC231198
0.8726	High Similarity	NPC234392
0.8726	High Similarity	NPC31311
0.8654	High Similarity	NPC148898
0.8649	High Similarity	NPC7018
0.8616	High Similarity	NPC111485
0.8608	High Similarity	NPC57512
0.859	High Similarity	NPC8337
0.859	High Similarity	NPC85747
0.8553	High Similarity	NPC128019
0.8553	High Similarity	NPC476567
0.8553	High Similarity	NPC136860
0.8544	High Similarity	NPC78733
0.8519	High Similarity	NPC276944
0.8519	High Similarity	NPC238530
0.8519	High Similarity	NPC232514
0.85	High Similarity	NPC477080
0.8457	Intermediate Similarity	NPC476569
0.8452	Intermediate Similarity	NPC210437
0.8452	Intermediate Similarity	NPC51957
0.8452	Intermediate Similarity	NPC16107
0.8452	Intermediate Similarity	NPC476144
0.8452	Intermediate Similarity	NPC106295
0.8428	Intermediate Similarity	NPC93593
0.8421	Intermediate Similarity	NPC213206
0.8421	Intermediate Similarity	NPC188163
0.8421	Intermediate Similarity	NPC328750
0.8421	Intermediate Similarity	NPC474915
0.8397	Intermediate Similarity	NPC7467
0.8385	Intermediate Similarity	NPC118804
0.8355	Intermediate Similarity	NPC314682
0.8333	Intermediate Similarity	NPC266753
0.8333	Intermediate Similarity	NPC160298
0.8333	Intermediate Similarity	NPC306902
0.8333	Intermediate Similarity	NPC477559
0.8333	Intermediate Similarity	NPC232924
0.8323	Intermediate Similarity	NPC130926
0.8303	Intermediate Similarity	NPC474324
0.8303	Intermediate Similarity	NPC57812
0.8253	Intermediate Similarity	NPC475845
0.8253	Intermediate Similarity	NPC241055
0.8242	Intermediate Similarity	NPC24264
0.8242	Intermediate Similarity	NPC476432
0.8221	Intermediate Similarity	NPC215829
0.8221	Intermediate Similarity	NPC97072
0.8221	Intermediate Similarity	NPC226428
0.8214	Intermediate Similarity	NPC2314
0.8208	Intermediate Similarity	NPC169387
0.8208	Intermediate Similarity	NPC477259
0.8204	Intermediate Similarity	NPC474708
0.8193	Intermediate Similarity	NPC247389
0.8182	Intermediate Similarity	NPC247972
0.8182	Intermediate Similarity	NPC255607
0.8182	Intermediate Similarity	NPC167546
0.8182	Intermediate Similarity	NPC3375
0.8182	Intermediate Similarity	NPC168409
0.8182	Intermediate Similarity	NPC302527
0.8182	Intermediate Similarity	NPC16805
0.8182	Intermediate Similarity	NPC225774
0.8176	Intermediate Similarity	NPC97221
0.8176	Intermediate Similarity	NPC151895
0.8176	Intermediate Similarity	NPC192768
0.8176	Intermediate Similarity	NPC220858
0.8176	Intermediate Similarity	NPC88249
0.8144	Intermediate Similarity	NPC82533
0.8144	Intermediate Similarity	NPC158148
0.8144	Intermediate Similarity	NPC266176
0.8144	Intermediate Similarity	NPC290759
0.8133	Intermediate Similarity	NPC219341
0.8129	Intermediate Similarity	NPC27887
0.8121	Intermediate Similarity	NPC160193
0.8118	Intermediate Similarity	NPC474470
0.8105	Intermediate Similarity	NPC252107
0.8095	Intermediate Similarity	NPC75958
0.8089	Intermediate Similarity	NPC185838
0.8086	Intermediate Similarity	NPC2413
0.8086	Intermediate Similarity	NPC278799
0.8086	Intermediate Similarity	NPC110416
0.8086	Intermediate Similarity	NPC276588
0.8086	Intermediate Similarity	NPC249797
0.8086	Intermediate Similarity	NPC469817
0.8086	Intermediate Similarity	NPC5238
0.8086	Intermediate Similarity	NPC127674
0.8086	Intermediate Similarity	NPC184026
0.8086	Intermediate Similarity	NPC193949
0.8086	Intermediate Similarity	NPC204828
0.8086	Intermediate Similarity	NPC172765
0.8086	Intermediate Similarity	NPC207757
0.8086	Intermediate Similarity	NPC76079
0.8086	Intermediate Similarity	NPC295691
0.8086	Intermediate Similarity	NPC39701
0.8086	Intermediate Similarity	NPC189266
0.8086	Intermediate Similarity	NPC54379
0.8084	Intermediate Similarity	NPC298979
0.8084	Intermediate Similarity	NPC210918
0.8084	Intermediate Similarity	NPC100566
0.8072	Intermediate Similarity	NPC39103
0.8072	Intermediate Similarity	NPC2770
0.8063	Intermediate Similarity	NPC274026
0.8061	Intermediate Similarity	NPC24954
0.8059	Intermediate Similarity	NPC49353
0.8059	Intermediate Similarity	NPC304675
0.805	Intermediate Similarity	NPC24233
0.805	Intermediate Similarity	NPC476571
0.805	Intermediate Similarity	NPC147390
0.805	Intermediate Similarity	NPC37144
0.805	Intermediate Similarity	NPC428
0.805	Intermediate Similarity	NPC246587
0.805	Intermediate Similarity	NPC59907
0.805	Intermediate Similarity	NPC135538
0.8047	Intermediate Similarity	NPC470739
0.8047	Intermediate Similarity	NPC225597
0.8047	Intermediate Similarity	NPC477640
0.8047	Intermediate Similarity	NPC67978
0.8047	Intermediate Similarity	NPC303581
0.8039	Intermediate Similarity	NPC99078
0.8039	Intermediate Similarity	NPC416184
0.8037	Intermediate Similarity	NPC247639
0.8037	Intermediate Similarity	NPC25084
0.8036	Intermediate Similarity	NPC58766
0.8036	Intermediate Similarity	NPC475686
0.8036	Intermediate Similarity	NPC470324
0.8036	Intermediate Similarity	NPC86469
0.8024	Intermediate Similarity	NPC86144
0.8024	Intermediate Similarity	NPC304659
0.8012	Intermediate Similarity	NPC237044
0.8012	Intermediate Similarity	NPC320104
0.8012	Intermediate Similarity	NPC189470
0.8012	Intermediate Similarity	NPC241704
0.8	Intermediate Similarity	NPC92541
0.8	Intermediate Similarity	NPC219162
0.7988	Intermediate Similarity	NPC474475
0.7987	Intermediate Similarity	NPC470707
0.7987	Intermediate Similarity	NPC321505
0.7987	Intermediate Similarity	NPC220923
0.7987	Intermediate Similarity	NPC191376
0.7987	Intermediate Similarity	NPC179825
0.7976	Intermediate Similarity	NPC190332
0.7976	Intermediate Similarity	NPC181653
0.7975	Intermediate Similarity	NPC187022
0.7975	Intermediate Similarity	NPC80129
0.7974	Intermediate Similarity	NPC277042
0.7974	Intermediate Similarity	NPC73883
0.7974	Intermediate Similarity	NPC136330
0.7974	Intermediate Similarity	NPC196609
0.7974	Intermediate Similarity	NPC230698
0.7974	Intermediate Similarity	NPC251454
0.7974	Intermediate Similarity	NPC205178
0.7974	Intermediate Similarity	NPC255817
0.7965	Intermediate Similarity	NPC474325
0.7963	Intermediate Similarity	NPC37272
0.7963	Intermediate Similarity	NPC82285
0.7963	Intermediate Similarity	NPC133011
0.7953	Intermediate Similarity	NPC308267
0.7941	Intermediate Similarity	NPC149090
0.7941	Intermediate Similarity	NPC19520
0.7937	Intermediate Similarity	NPC130941
0.7933	Intermediate Similarity	NPC477258
0.7931	Intermediate Similarity	NPC102760
0.7931	Intermediate Similarity	NPC73492
0.7931	Intermediate Similarity	NPC299990
0.7927	Intermediate Similarity	NPC147091
0.7919	Intermediate Similarity	NPC32154
0.7919	Intermediate Similarity	NPC149285
0.7919	Intermediate Similarity	NPC474745
0.7908	Intermediate Similarity	NPC167096
0.7907	Intermediate Similarity	NPC287588
0.7901	Intermediate Similarity	NPC81733
0.7901	Intermediate Similarity	NPC476568
0.7901	Intermediate Similarity	NPC326316
0.7889	Intermediate Similarity	NPC24228
0.7886	Intermediate Similarity	NPC116007
0.7882	Intermediate Similarity	NPC6152
0.7875	Intermediate Similarity	NPC253883
0.7875	Intermediate Similarity	NPC90844
0.7875	Intermediate Similarity	NPC95075
0.7875	Intermediate Similarity	NPC476151
0.7875	Intermediate Similarity	NPC144863
0.7871	Intermediate Similarity	NPC253429
0.787	Intermediate Similarity	NPC471604
0.7865	Intermediate Similarity	NPC63152
0.7865	Intermediate Similarity	NPC475597
0.7865	Intermediate Similarity	NPC473716
0.7861	Intermediate Similarity	NPC294790
0.7861	Intermediate Similarity	NPC148693
0.7861	Intermediate Similarity	NPC477560

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 NPC106786 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8452	Intermediate Similarity	NPD4584	Approved
0.8421	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD3639	Approved
0.8344	Intermediate Similarity	NPD3640	Phase 3
0.8344	Intermediate Similarity	NPD3641	Approved
0.8036	Intermediate Similarity	NPD2898	Approved
0.7975	Intermediate Similarity	NPD7298	Approved
0.7974	Intermediate Similarity	NPD2492	Phase 1
0.7862	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6107	Approved
0.7811	Intermediate Similarity	NPD4166	Phase 2
0.7805	Intermediate Similarity	NPD4772	Phase 2
0.7805	Intermediate Similarity	NPD4773	Phase 2
0.7799	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD4017	Approved
0.7771	Intermediate Similarity	NPD5977	Approved
0.7771	Intermediate Similarity	NPD5978	Approved
0.7669	Intermediate Similarity	NPD6030	Approved
0.7669	Intermediate Similarity	NPD6031	Approved
0.7662	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD4859	Phase 1
0.7647	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD4481	Phase 3
0.7593	Intermediate Similarity	NPD3124	Discontinued
0.7586	Intermediate Similarity	NPD5312	Approved
0.7586	Intermediate Similarity	NPD5313	Approved
0.7571	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD4420	Approved
0.7532	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8252	Approved
0.7529	Intermediate Similarity	NPD8251	Approved
0.7529	Intermediate Similarity	NPD8099	Discontinued
0.7486	Intermediate Similarity	NPD8156	Discontinued
0.7485	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5718	Phase 2
0.7473	Intermediate Similarity	NPD5457	Discontinued
0.7443	Intermediate Similarity	NPD3885	Approved
0.743	Intermediate Similarity	NPD6618	Phase 2
0.7399	Intermediate Similarity	NPD6071	Discontinued
0.7396	Intermediate Similarity	NPD4585	Approved
0.7394	Intermediate Similarity	NPD5006	Approved
0.7394	Intermediate Similarity	NPD5005	Approved
0.7374	Intermediate Similarity	NPD7281	Phase 3
0.7374	Intermediate Similarity	NPD2971	Approved
0.7374	Intermediate Similarity	NPD7280	Phase 3
0.7374	Intermediate Similarity	NPD2968	Approved
0.7353	Intermediate Similarity	NPD2563	Approved
0.7353	Intermediate Similarity	NPD2560	Approved
0.7341	Intermediate Similarity	NPD7802	Discontinued
0.7321	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6297	Approved
0.7299	Intermediate Similarity	NPD4010	Discontinued
0.7287	Intermediate Similarity	NPD4107	Approved
0.7267	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7833	Phase 2
0.7267	Intermediate Similarity	NPD7831	Phase 2
0.7257	Intermediate Similarity	NPD2969	Approved
0.7257	Intermediate Similarity	NPD2970	Approved
0.7256	Intermediate Similarity	NPD5241	Discontinued
0.725	Intermediate Similarity	NPD6895	Approved
0.725	Intermediate Similarity	NPD6896	Approved
0.7244	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD8054	Approved
0.7238	Intermediate Similarity	NPD8053	Approved
0.7216	Intermediate Similarity	NPD27	Approved
0.7216	Intermediate Similarity	NPD2489	Approved
0.7213	Intermediate Similarity	NPD7291	Discontinued
0.7209	Intermediate Similarity	NPD6788	Approved
0.72	Intermediate Similarity	NPD3051	Approved
0.7193	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5090	Approved
0.7176	Intermediate Similarity	NPD7110	Phase 1
0.7176	Intermediate Similarity	NPD5089	Approved
0.7158	Intermediate Similarity	NPD4482	Phase 3
0.7143	Intermediate Similarity	NPD6853	Approved
0.7143	Intermediate Similarity	NPD6851	Approved
0.7143	Intermediate Similarity	NPD4727	Phase 1
0.7135	Intermediate Similarity	NPD2490	Approved
0.7135	Intermediate Similarity	NPD2488	Approved
0.7126	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD2977	Approved
0.7093	Intermediate Similarity	NPD2978	Approved
0.7083	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5604	Discontinued
0.7066	Intermediate Similarity	NPD5297	Approved
0.7063	Intermediate Similarity	NPD3109	Approved
0.7063	Intermediate Similarity	NPD3110	Approved
0.7059	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2974	Approved
0.7037	Intermediate Similarity	NPD2975	Approved
0.7037	Intermediate Similarity	NPD5564	Approved
0.7037	Intermediate Similarity	NPD2973	Approved
0.7035	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD3057	Approved
0.7027	Intermediate Similarity	NPD3349	Phase 2
0.7024	Intermediate Similarity	NPD1424	Approved
0.7011	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7296	Approved
0.7	Intermediate Similarity	NPD4210	Discontinued
0.6989	Remote Similarity	NPD5677	Discontinued
0.6984	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6873	Phase 2
0.6977	Remote Similarity	NPD6386	Approved
0.6977	Remote Similarity	NPD6385	Approved
0.6975	Remote Similarity	NPD2653	Approved
0.697	Remote Similarity	NPD3816	Phase 1
0.697	Remote Similarity	NPD3815	Phase 1
0.6966	Remote Similarity	NPD6687	Approved
0.6966	Remote Similarity	NPD6688	Approved
0.6959	Remote Similarity	NPD824	Approved
0.6943	Remote Similarity	NPD3533	Approved
0.6943	Remote Similarity	NPD2972	Approved
0.6931	Remote Similarity	NPD6493	Phase 3
0.6927	Remote Similarity	NPD4580	Approved
0.6919	Remote Similarity	NPD6876	Approved
0.6919	Remote Similarity	NPD5676	Approved
0.6919	Remote Similarity	NPD6875	Approved
0.6909	Remote Similarity	NPD3656	Approved
0.6906	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7124	Phase 2
0.6903	Remote Similarity	NPD3705	Approved
0.6902	Remote Similarity	NPD7312	Approved
0.6902	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD7310	Approved
0.6902	Remote Similarity	NPD7311	Approved
0.6902	Remote Similarity	NPD7313	Approved
0.6898	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD5582	Discontinued
0.6894	Remote Similarity	NPD2674	Phase 3
0.6891	Remote Similarity	NPD3452	Approved
0.6891	Remote Similarity	NPD2493	Approved
0.6891	Remote Similarity	NPD2494	Approved
0.6891	Remote Similarity	NPD3450	Approved
0.6886	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5754	Discontinued
0.6878	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5242	Approved
0.6871	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7309	Approved
0.6864	Remote Similarity	NPD2420	Approved
0.6864	Remote Similarity	NPD2421	Approved
0.6856	Remote Similarity	NPD2491	Approved
0.6856	Remote Similarity	NPD3448	Approved
0.6848	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7906	Approved
0.6826	Remote Similarity	NPD4237	Approved
0.6826	Remote Similarity	NPD5177	Phase 3
0.6826	Remote Similarity	NPD4236	Phase 3
0.6815	Remote Similarity	NPD1420	Approved
0.6815	Remote Similarity	NPD1421	Approved
0.6807	Remote Similarity	NPD1375	Discontinued
0.6805	Remote Similarity	NPD3845	Phase 1
0.6805	Remote Similarity	NPD2120	Phase 2
0.679	Remote Similarity	NPD4475	Approved
0.679	Remote Similarity	NPD4474	Approved
0.6788	Remote Similarity	NPD4108	Discontinued
0.6788	Remote Similarity	NPD8095	Phase 1
0.6786	Remote Similarity	NPD4582	Approved
0.6786	Remote Similarity	NPD4583	Approved
0.6774	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7598	Phase 2
0.6763	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD5980	Discovery
0.6747	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1914	Approved
0.6744	Remote Similarity	NPD1670	Discontinued
0.6736	Remote Similarity	NPD5071	Phase 2
0.6735	Remote Similarity	NPD4004	Approved
0.6735	Remote Similarity	NPD4002	Approved
0.6728	Remote Similarity	NPD3145	Approved
0.6728	Remote Similarity	NPD3144	Approved
0.6727	Remote Similarity	NPD743	Approved
0.6726	Remote Similarity	NPD4162	Approved
0.6726	Remote Similarity	NPD3060	Approved
0.6724	Remote Similarity	NPD7028	Phase 2
0.672	Remote Similarity	NPD4578	Approved
0.672	Remote Similarity	NPD4577	Approved
0.672	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5772	Approved
0.6705	Remote Similarity	NPD5773	Approved
0.6702	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4663	Approved
0.6688	Remote Similarity	NPD5536	Phase 2
0.6687	Remote Similarity	NPD7905	Discontinued
0.6687	Remote Similarity	NPD7247	Discontinued
0.6686	Remote Similarity	NPD6748	Discontinued
0.6685	Remote Similarity	NPD4055	Discovery
0.6685	Remote Similarity	NPD3920	Phase 2
0.6684	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD8318	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data