NPASS Compound

Structure

CID317572 OpenBabel06191716142D 25 26 0 0 1 0 0 0 0 0999 V2000 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 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 4.3301 0.5000 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 3.4641 -0.0000 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 2.5981 -2.5000 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 -3.0000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 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 -0.8660 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 3 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 2.0000 0.0000 C 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 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 11 2 0 0 0 0 7 11 1 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 11 16 1 0 0 0 0 12 16 1 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 21 2 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 25 1 0 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	345.12
Volume:	345.418
LogP:	1.791
LogD:	1.166
LogS:	-3.658
# Rotatable Bonds:	7
TPSA:	116.69
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.692
Synthetic Accessibility Score:	3.189
Fsp3:	0.278
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:	-5.818
MDCK Permeability:	7.755508704576641e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	90.92607116699219%
Volume Distribution (VD):	0.221
Pgp-substrate:	6.086365699768066%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.058
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.467
CYP2C9-substrate:	0.757
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	0.992
Half-life (T1/2):	0.674

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.331
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.096
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.074
Carcinogencity:	0.103
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.819

Download Data

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

Natural Product: NPC317572

Natural Product ID:	NPC317572
*Common Name:**	4-Hydroxy-6-[3-Methylbutanoyloxy(Phenyl)Methyl]-2-Oxo-1H-Pyridine-3-Carboxylic Acid
IUPAC Name:	4-hydroxy-6-[3-methylbutanoyloxy(phenyl)methyl]-2-oxo-1H-pyridine-3-carboxylic acid
Synonyms:
Standard InCHIKey:	RQSUJBPFSUWQSA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H19NO6/c1-10(2)8-14(21)25-16(11-6-4-3-5-7-11)12-9-13(20)15(18(23)24)17(22)19-12/h3-7,9-10,16H,8H2,1-2H3,(H,23,24)(H2,19,20,22)
SMILES:	CC(C)CC(=O)OC(C1=CC=CC=C1)C2=CC(=C(C(=O)N2)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1771115
PubChem CID:	54684614
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0001097] Benzyloxycarbonyls

*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
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10724005]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10724008]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11099218]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332861]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387518]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16568716]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7649881]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8002401]
NPO31059	Penicillium	Genus	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9711252]

☑ 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	3
MIC	10
Others	25

Activity Type	# Activity
Cell Line	6
Individual Protein	1
Organism	30
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5013	Individual Protein	Chymase	Homo sapiens	IC50	=	0.42	ug.mL-1	PMID[485695]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	7.07	%	PMID[485695]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	21.53	%	PMID[485695]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	44.0	%	PMID[485695]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	71.07	%	PMID[485695]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	81.53	%	PMID[485695]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	11000.0	nM	PMID[485695]
NPT2	Others	Unspecified		IC50	=	4.5	ug.mL-1	PMID[485695]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	8.0	mm	PMID[485695]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	15.0	mm	PMID[485695]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	7.0	mm	PMID[485695]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	13.0	mm	PMID[485695]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IZ	=	8.0	mm	PMID[485695]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IZ	=	17.0	mm	PMID[485695]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	12.0	mm	PMID[485695]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	21.0	mm	PMID[485695]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	IZ	=	11.0	mm	PMID[485695]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	IZ	=	20.0	mm	PMID[485695]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	IZ	=	9.0	mm	PMID[485695]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	IZ	=	20.0	mm	PMID[485695]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	7.0	mm	PMID[485695]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	15.0	mm	PMID[485695]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	5.0	mm	PMID[485695]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	10.0	mm	PMID[485695]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	12.0	mm	PMID[485695]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	6.0	mm	PMID[485695]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	50.0	ug.mL-1	PMID[485695]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	25.0	ug.mL-1	PMID[485695]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	100.0	ug.mL-1	PMID[485695]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	50.0	ug.mL-1	PMID[485695]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	MIC	=	50.0	ug.mL-1	PMID[485695]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[485695]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[485695]

☑ 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 NPC317572 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	306
0.1-0.2	1821
0.2-0.3	6992
0.3-0.4	9932
0.4-0.5	11048
0.5-0.6	10570
0.6-0.7	1735
0.7-0.8	289
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9056	High Similarity	NPC320394
0.8063	Intermediate Similarity	NPC194040
0.8011	Intermediate Similarity	NPC191310
0.7882	Intermediate Similarity	NPC315545
0.7882	Intermediate Similarity	NPC314297
0.7857	Intermediate Similarity	NPC56170
0.7833	Intermediate Similarity	NPC313796
0.7833	Intermediate Similarity	NPC315638
0.7833	Intermediate Similarity	NPC472287
0.7833	Intermediate Similarity	NPC472286
0.7833	Intermediate Similarity	NPC314855
0.7833	Intermediate Similarity	NPC313345
0.7817	Intermediate Similarity	NPC230403
0.7816	Intermediate Similarity	NPC220337
0.78	Intermediate Similarity	NPC280714
0.7783	Intermediate Similarity	NPC314648
0.7767	Intermediate Similarity	NPC314834
0.7723	Intermediate Similarity	NPC155792
0.7678	Intermediate Similarity	NPC314270
0.7667	Intermediate Similarity	NPC3207
0.766	Intermediate Similarity	NPC470894
0.7628	Intermediate Similarity	NPC97746
0.7604	Intermediate Similarity	NPC283152
0.7596	Intermediate Similarity	NPC269367
0.7592	Intermediate Similarity	NPC303225
0.7581	Intermediate Similarity	NPC205372
0.7576	Intermediate Similarity	NPC144381
0.7574	Intermediate Similarity	NPC472284
0.7568	Intermediate Similarity	NPC116573
0.7563	Intermediate Similarity	NPC206186
0.7551	Intermediate Similarity	NPC42591
0.7523	Intermediate Similarity	NPC174760
0.7523	Intermediate Similarity	NPC469439
0.7511	Intermediate Similarity	NPC316224
0.75	Intermediate Similarity	NPC39679
0.75	Intermediate Similarity	NPC94842
0.75	Intermediate Similarity	NPC207851
0.7465	Intermediate Similarity	NPC312645
0.7461	Intermediate Similarity	NPC84347
0.7453	Intermediate Similarity	NPC16066
0.7453	Intermediate Similarity	NPC118228
0.7446	Intermediate Similarity	NPC153769
0.7444	Intermediate Similarity	NPC477589
0.7444	Intermediate Similarity	NPC477587
0.7437	Intermediate Similarity	NPC44354
0.743	Intermediate Similarity	NPC131885
0.7411	Intermediate Similarity	NPC62069
0.7406	Intermediate Similarity	NPC232225
0.7403	Intermediate Similarity	NPC471598
0.7395	Intermediate Similarity	NPC298436
0.7383	Intermediate Similarity	NPC169402
0.7378	Intermediate Similarity	NPC477588
0.7378	Intermediate Similarity	NPC477585
0.7378	Intermediate Similarity	NPC477590
0.7378	Intermediate Similarity	NPC477586
0.7376	Intermediate Similarity	NPC474701
0.7368	Intermediate Similarity	NPC321428
0.7368	Intermediate Similarity	NPC107123
0.7366	Intermediate Similarity	NPC123395
0.7361	Intermediate Similarity	NPC150239
0.7357	Intermediate Similarity	NPC291609
0.735	Intermediate Similarity	NPC183805
0.7349	Intermediate Similarity	NPC184408
0.7339	Intermediate Similarity	NPC51388
0.7339	Intermediate Similarity	NPC314633
0.7333	Intermediate Similarity	NPC245657
0.7324	Intermediate Similarity	NPC89508
0.7313	Intermediate Similarity	NPC124300
0.7311	Intermediate Similarity	NPC23294
0.7311	Intermediate Similarity	NPC87413
0.73	Intermediate Similarity	NPC66083
0.729	Intermediate Similarity	NPC116238
0.7286	Intermediate Similarity	NPC241025
0.7282	Intermediate Similarity	NPC194724
0.7282	Intermediate Similarity	NPC288943
0.7278	Intermediate Similarity	NPC280853
0.7269	Intermediate Similarity	NPC174576
0.7269	Intermediate Similarity	NPC247803
0.7268	Intermediate Similarity	NPC90229
0.7264	Intermediate Similarity	NPC309845
0.7264	Intermediate Similarity	NPC303951
0.726	Intermediate Similarity	NPC250807
0.726	Intermediate Similarity	NPC57797
0.7248	Intermediate Similarity	NPC253314
0.7241	Intermediate Similarity	NPC67401
0.724	Intermediate Similarity	NPC140296
0.724	Intermediate Similarity	NPC122968
0.724	Intermediate Similarity	NPC477787
0.724	Intermediate Similarity	NPC228377
0.724	Intermediate Similarity	NPC328186
0.7238	Intermediate Similarity	NPC285016
0.7235	Intermediate Similarity	NPC313804
0.7235	Intermediate Similarity	NPC315804
0.723	Intermediate Similarity	NPC146418
0.7228	Intermediate Similarity	NPC161292
0.7227	Intermediate Similarity	NPC473850
0.7222	Intermediate Similarity	NPC471596
0.7217	Intermediate Similarity	NPC58209
0.7217	Intermediate Similarity	NPC310618
0.7216	Intermediate Similarity	NPC249614
0.7211	Intermediate Similarity	NPC322644
0.7208	Intermediate Similarity	NPC67659
0.7207	Intermediate Similarity	NPC274640
0.7206	Intermediate Similarity	NPC45850
0.7206	Intermediate Similarity	NPC279401
0.7206	Intermediate Similarity	NPC79293
0.7205	Intermediate Similarity	NPC160100
0.7205	Intermediate Similarity	NPC188400
0.7198	Intermediate Similarity	NPC165964
0.7196	Intermediate Similarity	NPC476467
0.7193	Intermediate Similarity	NPC475844
0.7192	Intermediate Similarity	NPC469390
0.719	Intermediate Similarity	NPC132539
0.719	Intermediate Similarity	NPC137929
0.719	Intermediate Similarity	NPC164374
0.7177	Intermediate Similarity	NPC66815
0.7171	Intermediate Similarity	NPC135950
0.717	Intermediate Similarity	NPC86834
0.717	Intermediate Similarity	NPC210828
0.7168	Intermediate Similarity	NPC473187
0.7167	Intermediate Similarity	NPC473800
0.7166	Intermediate Similarity	NPC284348
0.7163	Intermediate Similarity	NPC250448
0.7163	Intermediate Similarity	NPC39500
0.7162	Intermediate Similarity	NPC146824
0.7157	Intermediate Similarity	NPC141915
0.7157	Intermediate Similarity	NPC114335
0.7157	Intermediate Similarity	NPC280964
0.7143	Intermediate Similarity	NPC292416
0.7143	Intermediate Similarity	NPC316841
0.7143	Intermediate Similarity	NPC473689
0.7143	Intermediate Similarity	NPC134848
0.7143	Intermediate Similarity	NPC316065
0.7143	Intermediate Similarity	NPC289905
0.7143	Intermediate Similarity	NPC165599
0.7143	Intermediate Similarity	NPC474688
0.7136	Intermediate Similarity	NPC109922
0.7136	Intermediate Similarity	NPC477788
0.7136	Intermediate Similarity	NPC478141
0.7136	Intermediate Similarity	NPC472752
0.713	Intermediate Similarity	NPC475362
0.7127	Intermediate Similarity	NPC471594
0.7123	Intermediate Similarity	NPC54066
0.7123	Intermediate Similarity	NPC4687
0.7123	Intermediate Similarity	NPC53344
0.7121	Intermediate Similarity	NPC164340
0.7117	Intermediate Similarity	NPC473506
0.7115	Intermediate Similarity	NPC103361
0.7113	Intermediate Similarity	NPC471978
0.7111	Intermediate Similarity	NPC244839
0.7111	Intermediate Similarity	NPC319880
0.7111	Intermediate Similarity	NPC320324
0.7104	Intermediate Similarity	NPC76565
0.7097	Intermediate Similarity	NPC74969
0.7097	Intermediate Similarity	NPC257142
0.7097	Intermediate Similarity	NPC330009
0.7087	Intermediate Similarity	NPC146724
0.7087	Intermediate Similarity	NPC166712
0.7085	Intermediate Similarity	NPC475631
0.7085	Intermediate Similarity	NPC476110
0.7085	Intermediate Similarity	NPC475600
0.7085	Intermediate Similarity	NPC87152
0.7081	Intermediate Similarity	NPC214428
0.708	Intermediate Similarity	NPC237702
0.7079	Intermediate Similarity	NPC90415
0.7078	Intermediate Similarity	NPC216428
0.7074	Intermediate Similarity	NPC253482
0.7072	Intermediate Similarity	NPC179287
0.7072	Intermediate Similarity	NPC473449
0.7072	Intermediate Similarity	NPC475137
0.7072	Intermediate Similarity	NPC475498
0.7067	Intermediate Similarity	NPC306376
0.7067	Intermediate Similarity	NPC217176
0.7061	Intermediate Similarity	NPC15801
0.7059	Intermediate Similarity	NPC144452
0.7054	Intermediate Similarity	NPC475644
0.7054	Intermediate Similarity	NPC471977
0.7054	Intermediate Similarity	NPC471190
0.7054	Intermediate Similarity	NPC470486
0.7051	Intermediate Similarity	NPC477979
0.7051	Intermediate Similarity	NPC134637
0.7048	Intermediate Similarity	NPC475406
0.7048	Intermediate Similarity	NPC34770
0.7048	Intermediate Similarity	NPC182222
0.7045	Intermediate Similarity	NPC128115
0.7042	Intermediate Similarity	NPC244741
0.7042	Intermediate Similarity	NPC193238
0.7039	Intermediate Similarity	NPC192306
0.7037	Intermediate Similarity	NPC308137
0.7037	Intermediate Similarity	NPC264176
0.7037	Intermediate Similarity	NPC472098
0.7037	Intermediate Similarity	NPC310211
0.7037	Intermediate Similarity	NPC244856
0.7032	Intermediate Similarity	NPC62367
0.7028	Intermediate Similarity	NPC289086
0.7025	Intermediate Similarity	NPC471979
0.7018	Intermediate Similarity	NPC152768
0.7018	Intermediate Similarity	NPC477909
0.7018	Intermediate Similarity	NPC42678
0.7018	Intermediate Similarity	NPC477907

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 NPC317572 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	580
0.2-0.3	800
0.3-0.4	1361
0.4-0.5	2849
0.5-0.6	2571
0.6-0.7	697
0.7-0.8	60
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8392	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.8048	Intermediate Similarity	NPD3925	Approved
0.7961	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7729	Intermediate Similarity	NPD5416	Discontinued
0.7696	Intermediate Similarity	NPD6641	Approved
0.7696	Intermediate Similarity	NPD6642	Approved
0.765	Intermediate Similarity	NPD5512	Phase 3
0.756	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5003	Discontinued
0.7421	Intermediate Similarity	NPD7031	Phase 1
0.7418	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1483	Discontinued
0.7368	Intermediate Similarity	NPD5429	Discontinued
0.7358	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7395	Discontinued
0.7323	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD2565	Phase 2
0.7313	Intermediate Similarity	NPD2564	Approved
0.7299	Intermediate Similarity	NPD4506	Discontinued
0.7296	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD5866	Approved
0.7254	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6974	Phase 3
0.7235	Intermediate Similarity	NPD6770	Approved
0.723	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD6962	Phase 2
0.722	Intermediate Similarity	NPD6550	Discontinued
0.7209	Intermediate Similarity	NPD4667	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7417	Discontinued
0.7189	Intermediate Similarity	NPD1926	Approved
0.7171	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3259	Approved
0.7143	Intermediate Similarity	NPD5488	Discontinued
0.7136	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD3263	Phase 3
0.7116	Intermediate Similarity	NPD7069	Discontinued
0.711	Intermediate Similarity	NPD5632	Approved
0.7087	Intermediate Similarity	NPD6716	Phase 1
0.7085	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4373	Phase 2
0.7079	Intermediate Similarity	NPD5256	Discontinued
0.7078	Intermediate Similarity	NPD3258	Approved
0.7074	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8356	Approved
0.7045	Intermediate Similarity	NPD8479	Phase 2
0.7041	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6874	Approved
0.7028	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD4952	Phase 3
0.7019	Intermediate Similarity	NPD1229	Phase 2
0.7018	Intermediate Similarity	NPD7853	Phase 2
0.7	Intermediate Similarity	NPD9510	Approved
0.7	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD1867	Approved
0.6987	Remote Similarity	NPD4368	Phase 2
0.6986	Remote Similarity	NPD4668	Phase 2
0.6986	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4897	Phase 2
0.6968	Remote Similarity	NPD7180	Phase 3
0.6964	Remote Similarity	NPD5640	Discontinued
0.6955	Remote Similarity	NPD4429	Discontinued
0.6953	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD3947	Discontinued
0.6947	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5022	Discontinued
0.6941	Remote Similarity	NPD8160	Phase 2
0.6938	Remote Similarity	NPD6988	Phase 1
0.6937	Remote Similarity	NPD7556	Discontinued
0.6934	Remote Similarity	NPD2779	Approved
0.6933	Remote Similarity	NPD8430	Approved
0.6933	Remote Similarity	NPD4086	Phase 1
0.6933	Remote Similarity	NPD4328	Approved
0.6927	Remote Similarity	NPD3243	Approved
0.6927	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD2792	Approved
0.6927	Remote Similarity	NPD3794	Approved
0.6927	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3795	Approved
0.6923	Remote Similarity	NPD6590	Discontinued
0.6916	Remote Similarity	NPD3507	Phase 2
0.6907	Remote Similarity	NPD5482	Discontinued
0.6907	Remote Similarity	NPD3986	Discontinued
0.6901	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2920	Discontinued
0.6901	Remote Similarity	NPD5513	Phase 2
0.6897	Remote Similarity	NPD6790	Phase 1
0.6895	Remote Similarity	NPD3257	Approved
0.6895	Remote Similarity	NPD5293	Phase 2
0.6891	Remote Similarity	NPD8463	Approved
0.6882	Remote Similarity	NPD3525	Discontinued
0.6881	Remote Similarity	NPD4204	Approved
0.6881	Remote Similarity	NPD4203	Approved
0.6878	Remote Similarity	NPD7878	Phase 2
0.6878	Remote Similarity	NPD9364	Phase 2
0.6878	Remote Similarity	NPD9363	Approved
0.6872	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4889	Approved
0.6842	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7777	Approved
0.6825	Remote Similarity	NPD7778	Approved
0.6825	Remote Similarity	NPD53	Approved
0.682	Remote Similarity	NPD6529	Discontinued
0.6816	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6159	Phase 2
0.6812	Remote Similarity	NPD8063	Discontinued
0.6812	Remote Similarity	NPD5316	Approved
0.681	Remote Similarity	NPD6722	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3006	Discontinued
0.6796	Remote Similarity	NPD2383	Phase 1
0.6796	Remote Similarity	NPD4948	Discontinued
0.6794	Remote Similarity	NPD4529	Approved
0.6794	Remote Similarity	NPD4528	Approved
0.6794	Remote Similarity	NPD4526	Approved
0.6792	Remote Similarity	NPD2778	Approved
0.6791	Remote Similarity	NPD2831	Approved
0.6788	Remote Similarity	NPD2672	Discontinued
0.6786	Remote Similarity	NPD1631	Approved
0.6786	Remote Similarity	NPD5507	Approved
0.6786	Remote Similarity	NPD5506	Approved
0.6783	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2336	Approved
0.6776	Remote Similarity	NPD7803	Approved
0.6774	Remote Similarity	NPD2510	Approved
0.6774	Remote Similarity	NPD2916	Discontinued
0.6774	Remote Similarity	NPD2509	Approved
0.6767	Remote Similarity	NPD5805	Approved
0.6763	Remote Similarity	NPD4334	Discontinued
0.6761	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD4417	Approved
0.6757	Remote Similarity	NPD1976	Approved
0.6756	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD820	Phase 3
0.675	Remote Similarity	NPD43	Approved
0.675	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6182	Approved
0.6749	Remote Similarity	NPD7708	Approved
0.6746	Remote Similarity	NPD6569	Phase 2
0.6735	Remote Similarity	NPD1685	Approved
0.6735	Remote Similarity	NPD1684	Approved
0.6732	Remote Similarity	NPD721	Approved
0.6731	Remote Similarity	NPD5928	Phase 1
0.6729	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7222	Phase 2
0.6716	Remote Similarity	NPD9362	Approved
0.6711	Remote Similarity	NPD6298	Discontinued
0.6711	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7994	Phase 2
0.6709	Remote Similarity	NPD7886	Phase 2
0.6709	Remote Similarity	NPD7885	Phase 2
0.6708	Remote Similarity	NPD7956	Approved
0.6708	Remote Similarity	NPD7955	Approved
0.67	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.67	Remote Similarity	NPD3920	Phase 2
0.67	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7467	Discontinued
0.6697	Remote Similarity	NPD6376	Discontinued
0.6696	Remote Similarity	NPD1466	Phase 3
0.6696	Remote Similarity	NPD1467	Approved
0.6683	Remote Similarity	NPD2844	Phase 3
0.6683	Remote Similarity	NPD2821	Approved
0.6682	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5475	Discontinued
0.6681	Remote Similarity	NPD3328	Phase 2
0.6667	Remote Similarity	NPD4950	Approved
0.6667	Remote Similarity	NPD2582	Approved
0.6667	Remote Similarity	NPD1638	Discovery
0.6667	Remote Similarity	NPD7426	Phase 1
0.6667	Remote Similarity	NPD3280	Approved
0.6667	Remote Similarity	NPD2581	Approved
0.6667	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD8102	Discontinued
0.6652	Remote Similarity	NPD8097	Phase 3
0.6652	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD8096	Phase 3
0.6652	Remote Similarity	NPD6198	Phase 1
0.6651	Remote Similarity	NPD2307	Discontinued
0.6651	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD3321	Discontinued
0.665	Remote Similarity	NPD1575	Approved
0.665	Remote Similarity	NPD1573	Approved
0.6649	Remote Similarity	NPD3684	Discontinued
0.664	Remote Similarity	NPD5450	Discontinued
0.664	Remote Similarity	NPD5922	Phase 3
0.6637	Remote Similarity	NPD3389	Approved
0.6637	Remote Similarity	NPD3393	Approved
0.6637	Remote Similarity	NPD3394	Approved
0.6636	Remote Similarity	NPD2177	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