NPASS Compound

Structure

CID113056 OpenBabel06191715462D 22 24 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 12 2 0 0 0 0 5 13 2 0 0 0 0 6 15 1 0 0 0 0 7 17 1 0 0 0 0 8 11 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 18 2 0 0 0 0 10 19 1 0 0 0 0 11 20 2 0 0 0 0 12 13 1 0 0 0 0 12 16 1 0 0 0 0 13 18 1 0 0 0 0 14 8 1 6 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 15 21 1 1 0 0 0 16 19 1 0 0 0 0 16 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	301.14
Volume:	303.165
LogP:	-0.01
LogD:	-0.488
LogS:	-1.08
# Rotatable Bonds:	4
TPSA:	84.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.857
Synthetic Accessibility Score:	3.201
Fsp3:	0.438
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:	-5.49
MDCK Permeability:	8.233121661760379e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.969
Human Intestinal Absorption (HIA):	0.848
20% Bioavailability (F20%):	0.54
30% Bioavailability (F30%):	0.425

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.75
Plasma Protein Binding (PPB):	32.761844635009766%
Volume Distribution (VD):	1.896
Pgp-substrate:	77.96774291992188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.139
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.307
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.455
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.148

ADMET: Excretion

Clearance (CL):	6.291
Half-life (T1/2):	0.762

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.912
Drug-inuced Liver Injury (DILI):	0.709
AMES Toxicity:	0.388
Rat Oral Acute Toxicity:	0.584
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.624
Carcinogencity:	0.346
Eye Corrosion:	0.004
Eye Irritation:	0.022
Respiratory Toxicity:	0.534

Download Data

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

Natural Product: NPC113056

Natural Product ID:	NPC113056
*Common Name:**	Febrifugine
IUPAC Name:	3-[3-[(2S,3R)-3-hydroxypiperidin-2-yl]-2-oxopropyl]quinazolin-4-one
Synonyms:	Febrifugine
Standard InCHIKey:	FWVHWDSCPKXMDB-LSDHHAIUSA-N
Standard InCHI:	InChI=1S/C16H19N3O3/c20-11(8-14-15(21)6-3-7-17-14)9-19-10-18-13-5-2-1-4-12(13)16(19)22/h1-2,4-5,10,14-15,17,21H,3,6-9H2/t14-,15+/m0/s1
SMILES:	c1ccc2c(c1)c(=O)n(CC(=O)C[C@H]1[C@@H](CCCN1)O)cn2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479432
PubChem CID:	63224
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000485] Quinazolines

*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
NPO22018	Hydrangea chinensis	Species	Hydrangeaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11473431]
NPO11394	Dichroa febrifuga	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19467876]
NPO22018	Hydrangea chinensis	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11394	Dichroa febrifuga	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22018	Hydrangea chinensis	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11394	Dichroa febrifuga	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11394	Dichroa febrifuga	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11394	Dichroa febrifuga	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22018	Hydrangea chinensis	Species	Hydrangeaceae	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
EC50	13
ED50	7
IC50	11
LD50	1
Others	19

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	4
Organism	33
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1759	Cell Line	FM3A	Mus musculus	EC50	=	170.0	nM	PMID[503967]
NPT1759	Cell Line	FM3A	Mus musculus	Selectivity	=	243.0	n.a.	PMID[503967]
NPT1759	Cell Line	FM3A	Mus musculus	EC50	=	170.0	nM	PMID[503968]
NPT1759	Cell Line	FM3A	Mus musculus	EC50	=	170.0	nM	PMID[503969]
NPT984	Cell Line	Hepatocyte		IC50	=	169.0	nM	PMID[503970]
NPT1460	Cell Line	L929	Mus musculus	EC50	=	0.167	ug.mL-1	PMID[503971]
NPT1460	Cell Line	L929	Mus musculus	Ratio EC50	=	118.0	n.a.	PMID[503971]
NPT2	Others	Unspecified		EC50	=	700.0	nM	PMID[503967]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	ED50	=	1.0	umol.kg-1	PMID[503967]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	ED90	=	5.0	uM kg-1	PMID[503967]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	0.7	nM	PMID[503968]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio	=	243.0	n.a.	PMID[503968]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	ED50	=	0.3	mg.kg-1	PMID[503968]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	ED90	=	1.5	mg kg-1	PMID[503968]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	0.7	nM	PMID[503969]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Selectivity	=	243.0	n.a.	PMID[503969]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	1.2	nM	PMID[503969]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Selectivity	=	142.0	n.a.	PMID[503969]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	1.0	umol.kg-1	PMID[503969]
NPT32	Organism	Mus musculus	Mus musculus	ED90	=	5.0	uM kg-1	PMID[503969]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.6	nM	PMID[503970]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.9	nM	PMID[503970]
NPT27	Others	Unspecified		Ratio LD50/ED50	=	17.0	n.a.	PMID[503971]
NPT32	Organism	Mus musculus	Mus musculus	LD50	=	7.1	mg.kg-1	PMID[503971]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	ED50	=	0.41	mg.kg-1	PMID[503971]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	0.0014	ug.mL-1	PMID[503971]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	0.00142	ug.mL-1	PMID[503971]
NPT27	Others	Unspecified		Activity	>	90.0	%	PMID[503973]
NPT27	Others	Unspecified		Activity	=	10.0	%	PMID[503973]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	378000000.0	n.a.	PMID[503973]
NPT610	Others	Molecular identity unknown		Activity	=	91.0	%	PMID[503973]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.00076	ug.mL-1	PMID[503975]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	ED50	=	2.3	mg.kg-1	PMID[503975]
NPT32	Organism	Mus musculus	Mus musculus	MTD	=	35.0	mg kg-1	PMID[503975]
NPT27	Others	Unspecified		TI	=	3.0	n.a.	PMID[503975]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	MCD	=	12.0	mg kg-1	PMID[503975]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.6	nM	PMID[503976]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.9	nM	PMID[503976]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2.1	nM	PMID[503976]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3.1	nM	PMID[503976]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	2.0	nM	PMID[503976]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5.4	nM	PMID[503976]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.2	nM	PMID[503976]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	ED50	=	2.3	mg.kg-1	PMID[503976]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	MCD	=	12.0	mg kg-1	PMID[503976]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	MTD	=	35.0	mg kg-1	PMID[503976]
NPT27	Others	Unspecified		TI	=	3.0	n.a.	PMID[503976]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	0.076	nM	PMID[503977]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	200.0	nM	PMID[503978]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	0.7	nM	PMID[503977]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	ED50	=	0.6	mg/kg/day	PMID[503977]

☑ 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 NPC113056 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	367
0.1-0.2	3921
0.2-0.3	16335
0.3-0.4	15329
0.4-0.5	2728
0.5-0.6	2844
0.6-0.7	1052
0.7-0.8	92
0.8-0.85	24
0.85-0.9	1
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC138293
0.8098	Intermediate Similarity	NPC154478
0.8086	Intermediate Similarity	NPC84317
0.8038	Intermediate Similarity	NPC324445
0.7701	Intermediate Similarity	NPC475094
0.7532	Intermediate Similarity	NPC122553
0.7457	Intermediate Similarity	NPC472118
0.7438	Intermediate Similarity	NPC207554
0.7436	Intermediate Similarity	NPC207428
0.7425	Intermediate Similarity	NPC295021
0.7405	Intermediate Similarity	NPC470787
0.7405	Intermediate Similarity	NPC472539
0.7405	Intermediate Similarity	NPC472540
0.7366	Intermediate Similarity	NPC472541
0.7366	Intermediate Similarity	NPC472542
0.7303	Intermediate Similarity	NPC131450
0.7303	Intermediate Similarity	NPC147298
0.7303	Intermediate Similarity	NPC182057
0.7296	Intermediate Similarity	NPC300299
0.7287	Intermediate Similarity	NPC106118
0.7284	Intermediate Similarity	NPC2823
0.7247	Intermediate Similarity	NPC14849
0.724	Intermediate Similarity	NPC225400
0.7232	Intermediate Similarity	NPC248862
0.7232	Intermediate Similarity	NPC328611
0.7209	Intermediate Similarity	NPC309531
0.7209	Intermediate Similarity	NPC472102
0.7202	Intermediate Similarity	NPC470786
0.7202	Intermediate Similarity	NPC471155
0.7202	Intermediate Similarity	NPC472538
0.7179	Intermediate Similarity	NPC72473
0.7179	Intermediate Similarity	NPC58827
0.7179	Intermediate Similarity	NPC307437
0.7178	Intermediate Similarity	NPC471164
0.7165	Intermediate Similarity	NPC270241
0.7126	Intermediate Similarity	NPC189116
0.7115	Intermediate Similarity	NPC322433
0.7091	Intermediate Similarity	NPC314287
0.7089	Intermediate Similarity	NPC194562
0.7077	Intermediate Similarity	NPC285192
0.7059	Intermediate Similarity	NPC179605
0.7059	Intermediate Similarity	NPC279385
0.7059	Intermediate Similarity	NPC117032
0.7055	Intermediate Similarity	NPC83214
0.7045	Intermediate Similarity	NPC214960
0.7045	Intermediate Similarity	NPC279527
0.7043	Intermediate Similarity	NPC471195
0.7043	Intermediate Similarity	NPC471196
0.7022	Intermediate Similarity	NPC292265
0.7019	Intermediate Similarity	NPC162417
0.7019	Intermediate Similarity	NPC316104
0.7013	Intermediate Similarity	NPC103292
0.7	Intermediate Similarity	NPC475607
0.7	Intermediate Similarity	NPC471199
0.7	Intermediate Similarity	NPC471192
0.6993	Remote Similarity	NPC177684
0.6993	Remote Similarity	NPC291962
0.6989	Remote Similarity	NPC471130
0.6971	Remote Similarity	NPC472117
0.6971	Remote Similarity	NPC88970
0.697	Remote Similarity	NPC316202
0.6965	Remote Similarity	NPC471197
0.6961	Remote Similarity	NPC474081
0.6948	Remote Similarity	NPC161956
0.6948	Remote Similarity	NPC112373
0.6948	Remote Similarity	NPC258531
0.6946	Remote Similarity	NPC136002
0.6944	Remote Similarity	NPC475594
0.6935	Remote Similarity	NPC471193
0.6935	Remote Similarity	NPC471194
0.6931	Remote Similarity	NPC471198
0.6927	Remote Similarity	NPC355
0.6923	Remote Similarity	NPC475761
0.6923	Remote Similarity	NPC254698
0.6923	Remote Similarity	NPC474041
0.6903	Remote Similarity	NPC257490
0.6889	Remote Similarity	NPC177261
0.6885	Remote Similarity	NPC475685
0.6884	Remote Similarity	NPC72956
0.6882	Remote Similarity	NPC300596
0.6882	Remote Similarity	NPC237649
0.6875	Remote Similarity	NPC472121
0.6872	Remote Similarity	NPC295548
0.6867	Remote Similarity	NPC43477
0.6859	Remote Similarity	NPC268534
0.685	Remote Similarity	NPC6865
0.685	Remote Similarity	NPC153980
0.6847	Remote Similarity	NPC248601
0.6845	Remote Similarity	NPC473815
0.6832	Remote Similarity	NPC316746
0.6813	Remote Similarity	NPC209389
0.6802	Remote Similarity	NPC471191
0.6791	Remote Similarity	NPC150308
0.679	Remote Similarity	NPC40364
0.678	Remote Similarity	NPC472120
0.678	Remote Similarity	NPC472101
0.6768	Remote Similarity	NPC478075
0.6766	Remote Similarity	NPC471574
0.676	Remote Similarity	NPC182131
0.6752	Remote Similarity	NPC39818
0.6723	Remote Similarity	NPC68650
0.672	Remote Similarity	NPC477159
0.6709	Remote Similarity	NPC283130
0.6709	Remote Similarity	NPC328683
0.6704	Remote Similarity	NPC472106
0.6703	Remote Similarity	NPC285622
0.6684	Remote Similarity	NPC21429
0.6667	Remote Similarity	NPC470548
0.6649	Remote Similarity	NPC92803
0.6648	Remote Similarity	NPC318183
0.6647	Remote Similarity	NPC144691
0.6634	Remote Similarity	NPC244425
0.6634	Remote Similarity	NPC15384
0.6632	Remote Similarity	NPC18890
0.6632	Remote Similarity	NPC284706
0.6609	Remote Similarity	NPC314223
0.6604	Remote Similarity	NPC175726
0.6604	Remote Similarity	NPC474082
0.6592	Remote Similarity	NPC176983
0.657	Remote Similarity	NPC470579
0.6568	Remote Similarity	NPC470301
0.6562	Remote Similarity	NPC192533
0.655	Remote Similarity	NPC130797
0.6546	Remote Similarity	NPC198401
0.6536	Remote Similarity	NPC27904
0.6536	Remote Similarity	NPC315368
0.6533	Remote Similarity	NPC172170
0.6517	Remote Similarity	NPC113946
0.6508	Remote Similarity	NPC97584
0.6506	Remote Similarity	NPC253476
0.65	Remote Similarity	NPC293458
0.6493	Remote Similarity	NPC122886
0.6489	Remote Similarity	NPC270301
0.6488	Remote Similarity	NPC287358
0.648	Remote Similarity	NPC316282
0.648	Remote Similarity	NPC36495
0.648	Remote Similarity	NPC469901
0.6474	Remote Similarity	NPC133003
0.6474	Remote Similarity	NPC478039
0.6471	Remote Similarity	NPC99043
0.6471	Remote Similarity	NPC218594
0.6463	Remote Similarity	NPC314431
0.6453	Remote Similarity	NPC472103
0.6452	Remote Similarity	NPC471743
0.6448	Remote Similarity	NPC66490
0.6433	Remote Similarity	NPC472241
0.6425	Remote Similarity	NPC213914
0.6425	Remote Similarity	NPC62104
0.6425	Remote Similarity	NPC1390
0.6425	Remote Similarity	NPC147983
0.6425	Remote Similarity	NPC177996
0.6425	Remote Similarity	NPC104345
0.6415	Remote Similarity	NPC27833
0.6413	Remote Similarity	NPC471943
0.6412	Remote Similarity	NPC315051
0.6412	Remote Similarity	NPC130251
0.6409	Remote Similarity	NPC286871
0.6406	Remote Similarity	NPC14994
0.6391	Remote Similarity	NPC132636
0.6386	Remote Similarity	NPC325479
0.6379	Remote Similarity	NPC246412
0.6374	Remote Similarity	NPC22082
0.6374	Remote Similarity	NPC186284
0.6369	Remote Similarity	NPC94167
0.6369	Remote Similarity	NPC285926
0.6369	Remote Similarity	NPC172937
0.6369	Remote Similarity	NPC14672
0.6369	Remote Similarity	NPC29285
0.6369	Remote Similarity	NPC315276
0.6368	Remote Similarity	NPC314659
0.6368	Remote Similarity	NPC470317
0.6364	Remote Similarity	NPC477432
0.6364	Remote Similarity	NPC300443
0.6364	Remote Similarity	NPC473329
0.6364	Remote Similarity	NPC472245
0.6359	Remote Similarity	NPC223595
0.6359	Remote Similarity	NPC167724
0.6359	Remote Similarity	NPC224970
0.6358	Remote Similarity	NPC314186
0.6349	Remote Similarity	NPC88110
0.6349	Remote Similarity	NPC91179
0.6346	Remote Similarity	NPC33742
0.634	Remote Similarity	NPC324091
0.6339	Remote Similarity	NPC52059
0.6339	Remote Similarity	NPC470069
0.6335	Remote Similarity	NPC477003
0.6333	Remote Similarity	NPC61013
0.6333	Remote Similarity	NPC469898
0.6333	Remote Similarity	NPC123241
0.6322	Remote Similarity	NPC472242
0.6321	Remote Similarity	NPC17059
0.6321	Remote Similarity	NPC220851
0.6319	Remote Similarity	NPC474926
0.6316	Remote Similarity	NPC472243
0.6316	Remote Similarity	NPC197335
0.6313	Remote Similarity	NPC209362
0.631	Remote Similarity	NPC474473
0.6308	Remote Similarity	NPC276430
0.6307	Remote Similarity	NPC242000
0.6303	Remote Similarity	NPC150863

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 NPC113056 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	586
0.2-0.3	1038
0.3-0.4	1916
0.4-0.5	2239
0.5-0.6	2076
0.6-0.7	975
0.7-0.8	115
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8305	Intermediate Similarity	NPD1992	Phase 2
0.8305	Intermediate Similarity	NPD1991	Phase 2
0.8305	Intermediate Similarity	NPD1990	Phase 2
0.7937	Intermediate Similarity	NPD4942	Approved
0.7569	Intermediate Similarity	NPD5042	Phase 1
0.756	Intermediate Similarity	NPD4393	Approved
0.756	Intermediate Similarity	NPD33	Approved
0.7545	Intermediate Similarity	NPD951	Approved
0.75	Intermediate Similarity	NPD4939	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD979	Approved
0.7439	Intermediate Similarity	NPD7088	Discontinued
0.7423	Intermediate Similarity	NPD6017	Discontinued
0.7345	Intermediate Similarity	NPD3995	Approved
0.7345	Intermediate Similarity	NPD3991	Approved
0.7345	Intermediate Similarity	NPD3994	Approved
0.7345	Intermediate Similarity	NPD3993	Approved
0.7345	Intermediate Similarity	NPD3996	Approved
0.7345	Intermediate Similarity	NPD3992	Approved
0.7303	Intermediate Similarity	NPD3998	Approved
0.7303	Intermediate Similarity	NPD3999	Approved
0.7303	Intermediate Similarity	NPD3997	Approved
0.7302	Intermediate Similarity	NPD7817	Phase 1
0.7288	Intermediate Similarity	NPD4091	Approved
0.7247	Intermediate Similarity	NPD4092	Approved
0.7232	Intermediate Similarity	NPD3522	Approved
0.7215	Intermediate Similarity	NPD1920	Approved
0.7215	Intermediate Similarity	NPD1919	Approved
0.7198	Intermediate Similarity	NPD6557	Phase 2
0.717	Intermediate Similarity	NPD1527	Phase 2
0.7167	Intermediate Similarity	NPD3989	Phase 3
0.7143	Intermediate Similarity	NPD5923	Phase 1
0.7135	Intermediate Similarity	NPD6613	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD3990	Phase 3
0.7115	Intermediate Similarity	NPD9540	Approved
0.7099	Intermediate Similarity	NPD4077	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1524	Phase 1
0.7059	Intermediate Similarity	NPD3248	Phase 1
0.7055	Intermediate Similarity	NPD6655	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5748	Phase 2
0.7027	Intermediate Similarity	NPD4515	Suspended
0.7025	Intermediate Similarity	NPD1781	Discontinued
0.7022	Intermediate Similarity	NPD2432	Approved
0.7022	Intermediate Similarity	NPD5727	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD1165	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD2431	Approved
0.7017	Intermediate Similarity	NPD2869	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2037	Approved
0.6994	Remote Similarity	NPD4517	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5024	Approved
0.6987	Remote Similarity	NPD9541	Approved
0.6987	Remote Similarity	NPD9539	Approved
0.6983	Remote Similarity	NPD7443	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4330	Approved
0.6978	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4329	Approved
0.6977	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6260	Discontinued
0.6971	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5856	Discontinued
0.6961	Remote Similarity	NPD3792	Approved
0.6957	Remote Similarity	NPD1541	Approved
0.6957	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5918	Discontinued
0.6944	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2356	Phase 1
0.6919	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4549	Discontinued
0.691	Remote Similarity	NPD2455	Approved
0.691	Remote Similarity	NPD2454	Approved
0.6882	Remote Similarity	NPD5942	Approved
0.6882	Remote Similarity	NPD5941	Approved
0.6865	Remote Similarity	NPD4412	Phase 2
0.6864	Remote Similarity	NPD3519	Discontinued
0.6839	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD3790	Phase 2
0.6832	Remote Similarity	NPD486	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6768	Approved
0.6813	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6805	Discontinued
0.6795	Remote Similarity	NPD1124	Approved
0.6795	Remote Similarity	NPD1123	Approved
0.679	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6342	Discontinued
0.6786	Remote Similarity	NPD7205	Discontinued
0.6778	Remote Similarity	NPD2350	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7727	Phase 2
0.6768	Remote Similarity	NPD3908	Approved
0.6757	Remote Similarity	NPD3470	Approved
0.6757	Remote Similarity	NPD3471	Approved
0.6755	Remote Similarity	NPD4988	Discontinued
0.6751	Remote Similarity	NPD8114	Approved
0.6751	Remote Similarity	NPD8115	Approved
0.6743	Remote Similarity	NPD6395	Phase 2
0.6743	Remote Similarity	NPD7105	Phase 1
0.6743	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3782	Discontinued
0.6732	Remote Similarity	NPD1323	Discontinued
0.6727	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD2506	Approved
0.672	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD478	Approved
0.6704	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.67	Remote Similarity	NPD3968	Approved
0.6688	Remote Similarity	NPD1079	Discontinued
0.6687	Remote Similarity	NPD797	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2369	Discontinued
0.6685	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8241	Phase 2
0.6683	Remote Similarity	NPD3410	Approved
0.6683	Remote Similarity	NPD3411	Phase 2
0.6667	Remote Similarity	NPD3423	Phase 2
0.6667	Remote Similarity	NPD2461	Phase 1
0.6667	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3422	Phase 3
0.6649	Remote Similarity	NPD5077	Approved
0.6649	Remote Similarity	NPD5076	Approved
0.6648	Remote Similarity	NPD2288	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7254	Discontinued
0.6646	Remote Similarity	NPD2949	Approved
0.6646	Remote Similarity	NPD2950	Approved
0.663	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3468	Approved
0.6627	Remote Similarity	NPD167	Phase 2
0.6627	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD168	Phase 1
0.6593	Remote Similarity	NPD5186	Approved
0.6593	Remote Similarity	NPD5183	Approved
0.6591	Remote Similarity	NPD7072	Phase 2
0.659	Remote Similarity	NPD5423	Phase 2
0.6587	Remote Similarity	NPD6294	Approved
0.6587	Remote Similarity	NPD6295	Approved
0.6585	Remote Similarity	NPD5581	Approved
0.6573	Remote Similarity	NPD4514	Approved
0.6573	Remote Similarity	NPD2427	Approved
0.6568	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD3625	Discontinued
0.6568	Remote Similarity	NPD2010	Phase 3
0.6564	Remote Similarity	NPD3828	Approved
0.6554	Remote Similarity	NPD7091	Discontinued
0.6552	Remote Similarity	NPD6144	Discontinued
0.655	Remote Similarity	NPD3967	Approved
0.6545	Remote Similarity	NPD941	Approved
0.6545	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5993	Phase 1
0.6541	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD2404	Discontinued
0.6536	Remote Similarity	NPD5992	Approved
0.6534	Remote Similarity	NPD2790	Discontinued
0.6534	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD2360	Approved
0.6533	Remote Similarity	NPD3802	Phase 3
0.6528	Remote Similarity	NPD7786	Discontinued
0.6527	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD4733	Approved
0.6514	Remote Similarity	NPD6575	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5840	Discontinued
0.6503	Remote Similarity	NPD7795	Phase 2
0.6494	Remote Similarity	NPD4432	Discontinued
0.6494	Remote Similarity	NPD4185	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD4682	Phase 2
0.6492	Remote Similarity	NPD3246	Discontinued
0.6491	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD4214	Discontinued
0.6488	Remote Similarity	NPD6358	Phase 2
0.6488	Remote Similarity	NPD6901	Phase 3
0.6485	Remote Similarity	NPD7232	Discontinued
0.6485	Remote Similarity	NPD6487	Approved
0.6485	Remote Similarity	NPD6486	Approved
0.6482	Remote Similarity	NPD3774	Approved
0.6482	Remote Similarity	NPD3775	Approved
0.6482	Remote Similarity	NPD3773	Approved
0.6481	Remote Similarity	NPD3606	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD1593	Approved
0.648	Remote Similarity	NPD7572	Phase 2
0.648	Remote Similarity	NPD7599	Phase 2
0.6477	Remote Similarity	NPD5504	Discontinued
0.6474	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5774	Approved
0.6471	Remote Similarity	NPD4461	Discontinued
0.6471	Remote Similarity	NPD5775	Approved
0.6471	Remote Similarity	NPD7428	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD2331	Discontinued
0.6467	Remote Similarity	NPD2791	Discontinued
0.6463	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD5510	Approved
0.645	Remote Similarity	NPD7142	Discontinued
0.6443	Remote Similarity	NPD7570	Approved
0.6443	Remote Similarity	NPD7569	Approved
0.6442	Remote Similarity	NPD3588	Discontinued
0.6442	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD3624	Phase 2
0.6433	Remote Similarity	NPD6566	Discontinued
0.6432	Remote Similarity	NPD7854	Phase 2
0.6425	Remote Similarity	NPD4258	Approved
0.6425	Remote Similarity	NPD3353	Approved
0.6425	Remote Similarity	NPD4259	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