NPASS Compound

Structure

CID235239 OpenBabel06191716032D 24 26 0 0 0 0 0 0 0 0999 V2000 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 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 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 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 20 1 0 0 0 0 2 20 1 0 0 0 0 3 7 2 0 0 0 0 3 13 1 0 0 0 0 4 8 2 0 0 0 0 4 13 1 0 0 0 0 5 6 2 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 19 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 20 1 0 0 0 0 11 13 2 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 14 19 2 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 18 2 0 0 0 0 17 22 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.12
Volume:	340.24
LogP:	4.436
LogD:	3.867
LogS:	-3.976
# Rotatable Bonds:	3
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.657
Synthetic Accessibility Score:	2.68
Fsp3:	0.15
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:	-4.903
MDCK Permeability:	1.4994498087617103e-05
Pgp-inhibitor:	0.074
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	100.880126953125%
Volume Distribution (VD):	0.525
Pgp-substrate:	0.4428497850894928%

ADMET: Metabolism

CYP1A2-inhibitor:	0.979
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.93
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.868
CYP2C9-substrate:	0.963
CYP2D6-inhibitor:	0.914
CYP2D6-substrate:	0.845
CYP3A4-inhibitor:	0.906
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	7.604
Half-life (T1/2):	0.611

ADMET: Toxicity

hERG Blockers:	0.334
Human Hepatotoxicity (H-HT):	0.428
Drug-inuced Liver Injury (DILI):	0.426
AMES Toxicity:	0.224
Rat Oral Acute Toxicity:	0.213
Maximum Recommended Daily Dose:	0.798
Skin Sensitization:	0.845
Carcinogencity:	0.839
Eye Corrosion:	0.004
Eye Irritation:	0.907
Respiratory Toxicity:	0.852

Download Data

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

Natural Product: NPC235239

Natural Product ID:	NPC235239
*Common Name:**	Kanzonol B
IUPAC Name:	(E)-1-(2,4-dihydroxyphenyl)-3-(2,2-dimethylchromen-6-yl)prop-2-en-1-one
Synonyms:
Standard InCHIKey:	TUHJQMZJOMZXJO-XVNBXDOJSA-N
Standard InCHI:	InChI=1S/C20H18O4/c1-20(2)10-9-14-11-13(4-8-19(14)24-20)3-7-17(22)16-6-5-15(21)12-18(16)23/h3-12,21,23H,1-2H3/b7-3+
SMILES:	CC1(C)C=Cc2cc(/C=C/C(=O)c3ccc(cc3O)O)ccc2O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL561840
PubChem CID:	10881804
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003472] 2'-Hydroxychalcones

*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
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23019	Glycyrrhiza kansuensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23019	Glycyrrhiza kansuensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23019	Glycyrrhiza kansuensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	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	4
Others	22

Activity Type	# Activity
Cell Line	12
CELL-LINE	1
Individual Protein	7
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	44300.0	nM	PMID[496859]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	14.0	%	PMID[496860]
NPT660	Cell Line	SW480	Homo sapiens	GI	=	14.0	%	PMID[496860]
NPT65	Cell Line	HepG2	Homo sapiens	GI	=	0.0	%	PMID[496860]
NPT2615	Cell Line	HEK-293T	Homo sapiens	GI	=	7.0	%	PMID[496860]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	23.0	%	PMID[496860]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	33.0	%	PMID[496860]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	FC	=	2.37	n.a.	PMID[496861]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	56.5	%	PMID[496862]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	FC	=	1.0	n.a.	PMID[496862]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	0.0	%	PMID[496862]
NPT65	Cell Line	HepG2	Homo sapiens	Inhibition	=	11.1	%	PMID[496862]
NPT81	Cell Line	A549	Homo sapiens	Inhibition	=	2.6	%	PMID[496862]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	45.7	%	PMID[496862]
NPT660	Cell Line	SW480	Homo sapiens	Inhibition	=	7.9	%	PMID[496862]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	>	60.0	%	PMID[496863]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	80.0	%	PMID[496863]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	2200.0	nM	PMID[496864]
NPT21742	CELL-LINE	L02	Homo sapiens	GI	=	5.0	%	PMID[496860]
NPT2	Others	Unspecified		Inhibition	=	78.0	%	PMID[496860]
NPT2	Others	Unspecified		IC50	=	7270.0	nM	PMID[496860]
NPT2	Others	Unspecified		Inhibition	=	1.0	%	PMID[496860]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Inhibition	=	4.4	%	PMID[496862]
NPT2	Others	Unspecified		Inhibition	=	60.7	%	PMID[496862]
NPT2	Others	Unspecified		IC50	=	5500.0	nM	PMID[496862]
NPT2	Others	Unspecified		Inhibition	>	40.0	%	PMID[496863]

☑ 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 NPC235239 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	376
0.1-0.2	1590
0.2-0.3	4208
0.3-0.4	11034
0.4-0.5	7066
0.5-0.6	3773
0.6-0.7	5918
0.7-0.8	5030
0.8-0.85	1957
0.85-0.9	1105
0.9-0.95	539
0.95-1	101

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC147688
0.9926	High Similarity	NPC156590
0.9926	High Similarity	NPC64908
0.9926	High Similarity	NPC118840
0.9926	High Similarity	NPC205006
0.9853	High Similarity	NPC11561
0.9853	High Similarity	NPC226636
0.9852	High Similarity	NPC305355
0.9852	High Similarity	NPC475680
0.9852	High Similarity	NPC172986
0.9852	High Similarity	NPC261227
0.9852	High Similarity	NPC270883
0.9781	High Similarity	NPC38219
0.9779	High Similarity	NPC110969
0.9779	High Similarity	NPC103362
0.9778	High Similarity	NPC220062
0.9778	High Similarity	NPC96565
0.9778	High Similarity	NPC301217
0.9778	High Similarity	NPC303633
0.9778	High Similarity	NPC216978
0.9778	High Similarity	NPC55018
0.971	High Similarity	NPC234629
0.971	High Similarity	NPC311741
0.9708	High Similarity	NPC62840
0.9708	High Similarity	NPC214236
0.9708	High Similarity	NPC299080
0.9708	High Similarity	NPC59739
0.9708	High Similarity	NPC144499
0.9708	High Similarity	NPC217083
0.9708	High Similarity	NPC78803
0.9708	High Similarity	NPC293852
0.9706	High Similarity	NPC159275
0.9706	High Similarity	NPC241100
0.9706	High Similarity	NPC69769
0.9706	High Similarity	NPC150522
0.9704	High Similarity	NPC201395
0.9638	High Similarity	NPC106985
0.9638	High Similarity	NPC18585
0.9638	High Similarity	NPC166138
0.9638	High Similarity	NPC219915
0.9635	High Similarity	NPC282300
0.9632	High Similarity	NPC18260
0.9632	High Similarity	NPC78913
0.9632	High Similarity	NPC217186
0.9632	High Similarity	NPC53181
0.9571	High Similarity	NPC104406
0.9571	High Similarity	NPC79469
0.9571	High Similarity	NPC237635
0.9571	High Similarity	NPC23728
0.9571	High Similarity	NPC24673
0.9571	High Similarity	NPC201731
0.9571	High Similarity	NPC110303
0.9571	High Similarity	NPC97716
0.9568	High Similarity	NPC278175
0.9568	High Similarity	NPC469953
0.9568	High Similarity	NPC209040
0.9568	High Similarity	NPC257236
0.9565	High Similarity	NPC200694
0.9559	High Similarity	NPC470668
0.9559	High Similarity	NPC470669
0.9556	High Similarity	NPC13408
0.9504	High Similarity	NPC132592
0.9504	High Similarity	NPC160821
0.9504	High Similarity	NPC266572
0.9504	High Similarity	NPC6511
0.95	High Similarity	NPC475052
0.95	High Similarity	NPC124729
0.95	High Similarity	NPC176229
0.95	High Similarity	NPC267375
0.95	High Similarity	NPC301276
0.95	High Similarity	NPC214774
0.95	High Similarity	NPC470647
0.95	High Similarity	NPC54577
0.95	High Similarity	NPC312973
0.95	High Similarity	NPC83357
0.95	High Similarity	NPC111786
0.95	High Similarity	NPC195621
0.95	High Similarity	NPC20488
0.95	High Similarity	NPC88964
0.95	High Similarity	NPC246948
0.95	High Similarity	NPC67805
0.95	High Similarity	NPC477955
0.95	High Similarity	NPC142405
0.9496	High Similarity	NPC257097
0.9496	High Similarity	NPC212932
0.9496	High Similarity	NPC9117
0.9496	High Similarity	NPC175504
0.9496	High Similarity	NPC221432
0.9496	High Similarity	NPC190637
0.9496	High Similarity	NPC169591
0.9496	High Similarity	NPC68104
0.9496	High Similarity	NPC150408
0.9496	High Similarity	NPC164980
0.9496	High Similarity	NPC149026
0.9496	High Similarity	NPC75049
0.9496	High Similarity	NPC293053
0.9496	High Similarity	NPC24821
0.9496	High Similarity	NPC11700
0.9496	High Similarity	NPC478086
0.9496	High Similarity	NPC39329
0.9496	High Similarity	NPC91560
0.9496	High Similarity	NPC316816
0.9496	High Similarity	NPC143896
0.9496	High Similarity	NPC214166
0.9496	High Similarity	NPC310130
0.9493	High Similarity	NPC14871
0.9493	High Similarity	NPC3188
0.9489	High Similarity	NPC23257
0.9485	High Similarity	NPC317119
0.9485	High Similarity	NPC266597
0.9485	High Similarity	NPC228661
0.9485	High Similarity	NPC250266
0.9481	High Similarity	NPC131039
0.9481	High Similarity	NPC151113
0.9437	High Similarity	NPC65775
0.9437	High Similarity	NPC221868
0.9437	High Similarity	NPC10027
0.9437	High Similarity	NPC37208
0.9433	High Similarity	NPC296998
0.9433	High Similarity	NPC473077
0.9433	High Similarity	NPC180477
0.9433	High Similarity	NPC166757
0.9433	High Similarity	NPC283234
0.9433	High Similarity	NPC14001
0.9429	High Similarity	NPC273538
0.9429	High Similarity	NPC319752
0.9429	High Similarity	NPC131568
0.9429	High Similarity	NPC197252
0.9429	High Similarity	NPC236766
0.9429	High Similarity	NPC326500
0.9429	High Similarity	NPC473013
0.9429	High Similarity	NPC216538
0.9429	High Similarity	NPC473015
0.9429	High Similarity	NPC131579
0.9424	High Similarity	NPC148757
0.9424	High Similarity	NPC76372
0.9424	High Similarity	NPC473042
0.9424	High Similarity	NPC32739
0.9424	High Similarity	NPC66515
0.9424	High Similarity	NPC107572
0.9424	High Similarity	NPC324134
0.9424	High Similarity	NPC161506
0.9424	High Similarity	NPC36181
0.9424	High Similarity	NPC147145
0.9424	High Similarity	NPC324436
0.9424	High Similarity	NPC194432
0.9424	High Similarity	NPC167624
0.9424	High Similarity	NPC37496
0.9424	High Similarity	NPC166934
0.9424	High Similarity	NPC76338
0.9424	High Similarity	NPC220998
0.9424	High Similarity	NPC227579
0.9424	High Similarity	NPC228504
0.9424	High Similarity	NPC78
0.9424	High Similarity	NPC166482
0.9424	High Similarity	NPC223500
0.9424	High Similarity	NPC328164
0.9424	High Similarity	NPC177354
0.9424	High Similarity	NPC64915
0.9424	High Similarity	NPC10937
0.9424	High Similarity	NPC265040
0.9424	High Similarity	NPC40833
0.9424	High Similarity	NPC125855
0.9424	High Similarity	NPC182852
0.9424	High Similarity	NPC296917
0.9424	High Similarity	NPC1089
0.9424	High Similarity	NPC306829
0.942	High Similarity	NPC219917
0.942	High Similarity	NPC172250
0.942	High Similarity	NPC80962
0.942	High Similarity	NPC471587
0.942	High Similarity	NPC326109
0.942	High Similarity	NPC213659
0.942	High Similarity	NPC259166
0.942	High Similarity	NPC48624
0.942	High Similarity	NPC204985
0.942	High Similarity	NPC215311
0.942	High Similarity	NPC144118
0.9416	High Similarity	NPC254168
0.9416	High Similarity	NPC21350
0.9416	High Similarity	NPC272844
0.9416	High Similarity	NPC248995
0.9416	High Similarity	NPC124269
0.9416	High Similarity	NPC131130
0.9412	High Similarity	NPC186838
0.9412	High Similarity	NPC29353
0.9412	High Similarity	NPC477244
0.9412	High Similarity	NPC98115
0.9412	High Similarity	NPC477242
0.9412	High Similarity	NPC124784
0.9412	High Similarity	NPC66349
0.9412	High Similarity	NPC1486
0.9412	High Similarity	NPC274109
0.9412	High Similarity	NPC161196
0.9412	High Similarity	NPC231772
0.9412	High Similarity	NPC473887
0.9412	High Similarity	NPC168105
0.9412	High Similarity	NPC127447
0.9412	High Similarity	NPC194281
0.9412	High Similarity	NPC249606

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 NPC235239 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	968
0.2-0.3	1463
0.3-0.4	2582
0.4-0.5	1931
0.5-0.6	1200
0.6-0.7	455
0.7-0.8	144
0.8-0.85	42
0.85-0.9	17
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9568	High Similarity	NPD7410	Clinical (unspecified phase)
0.9429	High Similarity	NPD4378	Clinical (unspecified phase)
0.9137	High Similarity	NPD1549	Phase 2
0.9065	High Similarity	NPD1552	Clinical (unspecified phase)
0.9065	High Similarity	NPD1550	Clinical (unspecified phase)
0.9058	High Similarity	NPD1510	Phase 2
0.9044	High Similarity	NPD1240	Approved
0.8993	High Similarity	NPD2796	Approved
0.8913	High Similarity	NPD1607	Approved
0.8912	High Similarity	NPD7411	Suspended
0.8844	High Similarity	NPD4380	Phase 2
0.8792	High Similarity	NPD2393	Clinical (unspecified phase)
0.8742	High Similarity	NPD7075	Discontinued
0.8733	High Similarity	NPD8443	Clinical (unspecified phase)
0.8725	High Similarity	NPD6801	Discontinued
0.869	High Similarity	NPD1511	Approved
0.8667	High Similarity	NPD7096	Clinical (unspecified phase)
0.8667	High Similarity	NPD7819	Suspended
0.8611	High Similarity	NPD3750	Approved
0.8571	High Similarity	NPD1512	Approved
0.8562	High Similarity	NPD6799	Approved
0.8543	High Similarity	NPD2801	Approved
0.8542	High Similarity	NPD7421	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD1934	Approved
0.8431	Intermediate Similarity	NPD7768	Phase 2
0.8414	Intermediate Similarity	NPD1243	Approved
0.8414	Intermediate Similarity	NPD2800	Approved
0.8408	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD2799	Discontinued
0.8377	Intermediate Similarity	NPD3749	Approved
0.8357	Intermediate Similarity	NPD2313	Discontinued
0.8344	Intermediate Similarity	NPD6599	Discontinued
0.8333	Intermediate Similarity	NPD2935	Discontinued
0.8312	Intermediate Similarity	NPD3882	Suspended
0.8276	Intermediate Similarity	NPD2344	Approved
0.8264	Intermediate Similarity	NPD3748	Approved
0.8261	Intermediate Similarity	NPD1203	Approved
0.8252	Intermediate Similarity	NPD6651	Approved
0.825	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6959	Discontinued
0.8207	Intermediate Similarity	NPD1551	Phase 2
0.8146	Intermediate Similarity	NPD920	Approved
0.8146	Intermediate Similarity	NPD5403	Approved
0.8138	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD3817	Phase 2
0.8121	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD3268	Approved
0.8075	Intermediate Similarity	NPD3818	Discontinued
0.8071	Intermediate Similarity	NPD2798	Approved
0.8063	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6166	Phase 2
0.8063	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD2309	Approved
0.8049	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD9717	Approved
0.8038	Intermediate Similarity	NPD5494	Approved
0.8037	Intermediate Similarity	NPD5953	Discontinued
0.8025	Intermediate Similarity	NPD7286	Phase 2
0.8014	Intermediate Similarity	NPD4308	Phase 3
0.8013	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD2797	Approved
0.7987	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD943	Approved
0.7971	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD6100	Approved
0.7959	Intermediate Similarity	NPD6099	Approved
0.7958	Intermediate Similarity	NPD6832	Phase 2
0.7937	Intermediate Similarity	NPD6232	Discontinued
0.7922	Intermediate Similarity	NPD3226	Approved
0.7914	Intermediate Similarity	NPD7054	Approved
0.7905	Intermediate Similarity	NPD2346	Discontinued
0.7901	Intermediate Similarity	NPD7473	Discontinued
0.7895	Intermediate Similarity	NPD2533	Approved
0.7895	Intermediate Similarity	NPD2532	Approved
0.7895	Intermediate Similarity	NPD2534	Approved
0.7891	Intermediate Similarity	NPD7033	Discontinued
0.7879	Intermediate Similarity	NPD6559	Discontinued
0.7867	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7472	Approved
0.7866	Intermediate Similarity	NPD7074	Phase 3
0.7848	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD422	Phase 1
0.7829	Intermediate Similarity	NPD7390	Discontinued
0.7818	Intermediate Similarity	NPD6797	Phase 2
0.781	Intermediate Similarity	NPD1548	Phase 1
0.7785	Intermediate Similarity	NPD5402	Approved
0.7771	Intermediate Similarity	NPD7251	Discontinued
0.775	Intermediate Similarity	NPD919	Approved
0.7748	Intermediate Similarity	NPD4628	Phase 3
0.7746	Intermediate Similarity	NPD3266	Approved
0.7746	Intermediate Similarity	NPD3267	Approved
0.774	Intermediate Similarity	NPD4307	Phase 2
0.7725	Intermediate Similarity	NPD7808	Phase 3
0.7708	Intermediate Similarity	NPD4908	Phase 1
0.7697	Intermediate Similarity	NPD5844	Phase 1
0.7687	Intermediate Similarity	NPD5124	Phase 1
0.7687	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD3225	Approved
0.766	Intermediate Similarity	NPD3972	Approved
0.7655	Intermediate Similarity	NPD4625	Phase 3
0.7654	Intermediate Similarity	NPD1247	Approved
0.7643	Intermediate Similarity	NPD6585	Discontinued
0.7619	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD1610	Phase 2
0.7586	Intermediate Similarity	NPD4360	Phase 2
0.7586	Intermediate Similarity	NPD4363	Phase 3
0.7568	Intermediate Similarity	NPD1933	Approved
0.7566	Intermediate Similarity	NPD2654	Approved
0.7562	Intermediate Similarity	NPD4288	Approved
0.7561	Intermediate Similarity	NPD3926	Phase 2
0.7545	Intermediate Similarity	NPD1729	Discontinued
0.7543	Intermediate Similarity	NPD4361	Phase 2
0.7543	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD9493	Approved
0.75	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD1164	Approved
0.75	Intermediate Similarity	NPD5049	Phase 3
0.7484	Intermediate Similarity	NPD5890	Approved
0.7484	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5889	Approved
0.7483	Intermediate Similarity	NPD5404	Approved
0.7483	Intermediate Similarity	NPD1296	Phase 2
0.7483	Intermediate Similarity	NPD5408	Approved
0.7483	Intermediate Similarity	NPD5406	Approved
0.7483	Intermediate Similarity	NPD3764	Approved
0.7483	Intermediate Similarity	NPD411	Approved
0.7483	Intermediate Similarity	NPD5405	Approved
0.7468	Intermediate Similarity	NPD2354	Approved
0.7468	Intermediate Similarity	NPD7458	Discontinued
0.7465	Intermediate Similarity	NPD1201	Approved
0.7453	Intermediate Similarity	NPD2296	Approved
0.7452	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD447	Suspended
0.7445	Intermediate Similarity	NPD1241	Discontinued
0.7434	Intermediate Similarity	NPD1471	Phase 3
0.7429	Intermediate Similarity	NPD9545	Approved
0.7413	Intermediate Similarity	NPD1608	Approved
0.7403	Intermediate Similarity	NPD7003	Approved
0.7396	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6798	Discontinued
0.7361	Intermediate Similarity	NPD4749	Approved
0.7358	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4287	Approved
0.7347	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1019	Discontinued
0.7322	Intermediate Similarity	NPD7584	Approved
0.7321	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2353	Approved
0.732	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1481	Phase 2
0.7289	Intermediate Similarity	NPD5710	Approved
0.7289	Intermediate Similarity	NPD5711	Approved
0.7279	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6104	Discontinued
0.7244	Intermediate Similarity	NPD3887	Approved
0.7222	Intermediate Similarity	NPD7577	Discontinued
0.7222	Intermediate Similarity	NPD6844	Discontinued
0.7222	Intermediate Similarity	NPD1535	Discovery
0.7219	Intermediate Similarity	NPD230	Phase 1
0.7215	Intermediate Similarity	NPD4662	Approved
0.7215	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4661	Approved
0.7203	Intermediate Similarity	NPD17	Approved
0.7202	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1876	Approved
0.7186	Intermediate Similarity	NPD7229	Phase 3
0.7161	Intermediate Similarity	NPD2424	Discontinued
0.7152	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3140	Approved
0.7152	Intermediate Similarity	NPD1613	Approved
0.7152	Intermediate Similarity	NPD3142	Approved
0.7143	Intermediate Similarity	NPD4476	Approved
0.7143	Intermediate Similarity	NPD4477	Approved
0.7134	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5535	Approved
0.7118	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3751	Discontinued
0.7117	Intermediate Similarity	NPD6280	Approved
0.7117	Intermediate Similarity	NPD6279	Approved
0.7114	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6355	Discontinued
0.7101	Intermediate Similarity	NPD2403	Approved
0.7093	Intermediate Similarity	NPD3823	Discontinued
0.7089	Intermediate Similarity	NPD7440	Discontinued
0.7086	Intermediate Similarity	NPD6233	Phase 2

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