NPASS Compound

Structure

CID66252 OpenBabel06191715402D 32 33 0 0 0 0 0 0 0 0999 V2000 5.8839 2.4265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6811 -2.9118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0433 -2.9118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4853 0.8406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8839 1.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8406 -2.4265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7244 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5217 0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0433 -1.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2028 -0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6811 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7244 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 -2.4265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8839 -0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 -1.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2028 -1.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8839 -1.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0433 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6811 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5650 -0.4853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6811 -2.9118 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3622 -1.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7244 -1.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0433 0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5217 -1.4559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 1.4559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8406 -1.4559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 11 1 0 0 0 0 4 24 1 0 0 0 0 5 24 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 13 1 0 0 0 0 11 18 2 0 0 0 0 11 19 1 0 0 0 0 12 18 1 0 0 0 0 12 20 2 0 0 0 0 13 21 1 0 0 0 0 13 22 2 0 0 0 0 14 16 1 0 0 0 0 14 25 2 0 0 0 0 15 17 1 0 0 0 0 15 26 2 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 27 1 0 0 0 0 19 28 1 0 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 22 24 1 0 0 0 0 22 31 1 0 0 0 0 23 24 1 0 0 0 0 23 32 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.19
Volume:	455.777
LogP:	3.548
LogD:	0.54
LogS:	-2.02
# Rotatable Bonds:	8
TPSA:	146.04
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.408
Synthetic Accessibility Score:	4.082
Fsp3:	0.542
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.893
MDCK Permeability:	1.4788050066272262e-05
Pgp-inhibitor:	0.807
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.551
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	93.51185607910156%
Volume Distribution (VD):	0.648
Pgp-substrate:	2.96625018119812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.863
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.584
CYP2C9-inhibitor:	0.284
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.657
CYP3A4-substrate:	0.456

ADMET: Excretion

Clearance (CL):	13.075
Half-life (T1/2):	0.338

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.099
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.917
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.172
Carcinogencity:	0.224
Eye Corrosion:	0.007
Eye Irritation:	0.642
Respiratory Toxicity:	0.302

Download Data

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

Natural Product: NPC66252

Natural Product ID:	NPC66252
*Common Name:**	2-Butanoyl-4-[(3-Butanoyl-2,4,6-Trihydroxy-5-Methylphenyl)Methyl]-3,5-Dihydroxy-6,6-Dimethylcyclohexa-2,4-Dien-1-One
IUPAC Name:	2-butanoyl-4-[(3-butanoyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one
Synonyms:	NSC-115497
Standard InCHIKey:	NHVQLOCTXSMKIX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H30O8/c1-6-8-14(25)16-19(28)11(3)18(27)12(20(16)29)10-13-21(30)17(15(26)9-7-2)23(32)24(4,5)22(13)31/h27-31H,6-10H2,1-5H3
SMILES:	CCCC(=O)c1c(c(C)c(c(CC2=C(C(C)(C)C(=O)C(=C2O)C(=O)CCC)O)c1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL291819
PubChem CID:	8237
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.foodchem.2013.08.121]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[12951487]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[16180814]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	seeds	Shizuoka prefecture, Japan	n.a.	PMID[16499314]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16870425]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18068204]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21434603]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	flower	n.a.	PMID[21922925]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[21925888]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22377672]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265489]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaves	Bandung, West Java, Indonesia		PMID[23621359]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24013342]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31037	Alhagi pseudalhagi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22283	Alhagi maurorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO493	Dryopteris filix- mas	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27921	Dryopteris chrysocoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18414	Dryopteris caucasica	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27921	Dryopteris chrysocoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22283	Alhagi maurorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18414	Dryopteris caucasica	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	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
GI50	54
Others	1

Activity Type	# Activity
Cell Line	54
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT609	Individual Protein	Human immunodeficiency virus type 1 protease	Human immunodeficiency virus 1	ID50	=	26.0	uM	PMID[518794]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518795]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518795]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	15776.11	nM	PMID[518795]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	15595.53	nM	PMID[518795]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518795]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	10209.39	nM	PMID[518795]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518795]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518795]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	46773.51	nM	PMID[518795]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	15417.0	nM	PMID[518795]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518795]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	10964.78	nM	PMID[518795]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	31768.74	nM	PMID[518795]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	22855.99	nM	PMID[518795]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	11939.88	nM	PMID[518795]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518795]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	20701.41	nM	PMID[518795]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518795]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	14655.48	nM	PMID[518795]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	30619.63	nM	PMID[518795]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	13931.57	nM	PMID[518795]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	23823.19	nM	PMID[518795]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518795]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	22233.1	nM	PMID[518795]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	16982.44	nM	PMID[518795]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	43551.19	nM	PMID[518795]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	18967.06	nM	PMID[518795]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518795]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	22438.82	nM	PMID[518795]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	25176.77	nM	PMID[518795]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	10914.4	nM	PMID[518795]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	29444.22	nM	PMID[518795]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	19952.62	nM	PMID[518795]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	12560.3	nM	PMID[518795]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	34833.73	nM	PMID[518795]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	21928.05	nM	PMID[518795]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518795]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	19054.61	nM	PMID[518795]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	22646.44	nM	PMID[518795]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	14288.94	nM	PMID[518795]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	49203.95	nM	PMID[518795]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518795]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518795]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518795]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	36982.82	nM	PMID[518795]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	16865.53	nM	PMID[518795]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	40644.33	nM	PMID[518795]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518795]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518795]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	420.73	nM	PMID[518795]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	16180.8	nM	PMID[518795]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	20370.42	nM	PMID[518795]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	17021.59	nM	PMID[518795]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	19408.86	nM	PMID[518795]

☑ 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 NPC66252 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	316
0.1-0.2	1564
0.2-0.3	4202
0.3-0.4	11676
0.4-0.5	8983
0.5-0.6	7200
0.6-0.7	6184
0.7-0.8	2307
0.8-0.85	179
0.85-0.9	65
0.9-0.95	13
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9664	High Similarity	NPC328983
0.9583	High Similarity	NPC329205
0.9583	High Similarity	NPC316625
0.958	High Similarity	NPC290466
0.9487	High Similarity	NPC229649
0.9426	High Similarity	NPC73203
0.9328	High Similarity	NPC232708
0.9187	High Similarity	NPC164894
0.9187	High Similarity	NPC475553
0.9008	High Similarity	NPC91105
0.8934	High Similarity	NPC65761
0.8934	High Similarity	NPC472029
0.8926	High Similarity	NPC215392
0.8906	High Similarity	NPC475088
0.888	High Similarity	NPC221777
0.8871	High Similarity	NPC267846
0.8843	High Similarity	NPC149246
0.88	High Similarity	NPC190043
0.88	High Similarity	NPC98254
0.88	High Similarity	NPC103356
0.88	High Similarity	NPC169250
0.88	High Similarity	NPC105157
0.88	High Similarity	NPC23126
0.88	High Similarity	NPC116513
0.88	High Similarity	NPC72158
0.88	High Similarity	NPC162612
0.88	High Similarity	NPC30501
0.88	High Similarity	NPC266689
0.88	High Similarity	NPC100067
0.879	High Similarity	NPC475733
0.878	High Similarity	NPC306288
0.877	High Similarity	NPC303737
0.877	High Similarity	NPC226275
0.874	High Similarity	NPC186628
0.873	High Similarity	NPC21305
0.873	High Similarity	NPC470981
0.873	High Similarity	NPC473017
0.872	High Similarity	NPC62952
0.8712	High Similarity	NPC477056
0.8712	High Similarity	NPC477055
0.8699	High Similarity	NPC218333
0.8699	High Similarity	NPC309765
0.8672	High Similarity	NPC279566
0.8661	High Similarity	NPC474998
0.8636	High Similarity	NPC473622
0.8607	High Similarity	NPC294037
0.8605	High Similarity	NPC474109
0.8595	High Similarity	NPC209486
0.8595	High Similarity	NPC40649
0.8594	High Similarity	NPC21378
0.8594	High Similarity	NPC470987
0.8571	High Similarity	NPC268178
0.8571	High Similarity	NPC180501
0.8571	High Similarity	NPC54820
0.8538	High Similarity	NPC215875
0.8538	High Similarity	NPC15834
0.8537	High Similarity	NPC146642
0.8527	High Similarity	NPC275504
0.8527	High Similarity	NPC475042
0.8519	High Similarity	NPC316560
0.8519	High Similarity	NPC316911
0.8516	High Similarity	NPC476119
0.8507	High Similarity	NPC270913
0.8473	Intermediate Similarity	NPC474117
0.8473	Intermediate Similarity	NPC474224
0.8473	Intermediate Similarity	NPC16197
0.8468	Intermediate Similarity	NPC196976
0.8468	Intermediate Similarity	NPC242895
0.8462	Intermediate Similarity	NPC185624
0.8462	Intermediate Similarity	NPC175738
0.8456	Intermediate Similarity	NPC325346
0.8456	Intermediate Similarity	NPC321148
0.8456	Intermediate Similarity	NPC321629
0.8456	Intermediate Similarity	NPC323884
0.8456	Intermediate Similarity	NPC326193
0.8444	Intermediate Similarity	NPC82920
0.8444	Intermediate Similarity	NPC164697
0.8444	Intermediate Similarity	NPC289660
0.8409	Intermediate Similarity	NPC475917
0.84	Intermediate Similarity	NPC133909
0.84	Intermediate Similarity	NPC32032
0.8397	Intermediate Similarity	NPC139074
0.8397	Intermediate Similarity	NPC470988
0.8397	Intermediate Similarity	NPC213485
0.8397	Intermediate Similarity	NPC40524
0.8382	Intermediate Similarity	NPC111201
0.8374	Intermediate Similarity	NPC161617
0.8361	Intermediate Similarity	NPC121259
0.8346	Intermediate Similarity	NPC477454
0.8333	Intermediate Similarity	NPC282780
0.8333	Intermediate Similarity	NPC470984
0.8333	Intermediate Similarity	NPC166480
0.832	Intermediate Similarity	NPC267552
0.832	Intermediate Similarity	NPC115159
0.832	Intermediate Similarity	NPC45438
0.832	Intermediate Similarity	NPC156139
0.832	Intermediate Similarity	NPC224273
0.832	Intermediate Similarity	NPC73532
0.832	Intermediate Similarity	NPC143427
0.832	Intermediate Similarity	NPC19174
0.8308	Intermediate Similarity	NPC84772
0.8284	Intermediate Similarity	NPC147691
0.8284	Intermediate Similarity	NPC53001
0.8284	Intermediate Similarity	NPC470985
0.8284	Intermediate Similarity	NPC470989
0.8281	Intermediate Similarity	NPC473691
0.8271	Intermediate Similarity	NPC130899
0.8271	Intermediate Similarity	NPC70859
0.8271	Intermediate Similarity	NPC244640
0.8271	Intermediate Similarity	NPC290803
0.8271	Intermediate Similarity	NPC279291
0.8271	Intermediate Similarity	NPC61153
0.8271	Intermediate Similarity	NPC283590
0.8271	Intermediate Similarity	NPC470210
0.8271	Intermediate Similarity	NPC474076
0.8271	Intermediate Similarity	NPC103842
0.8258	Intermediate Similarity	NPC285054
0.8258	Intermediate Similarity	NPC114183
0.8244	Intermediate Similarity	NPC324482
0.8244	Intermediate Similarity	NPC250057
0.824	Intermediate Similarity	NPC297186
0.8231	Intermediate Similarity	NPC92624
0.8231	Intermediate Similarity	NPC230818
0.8226	Intermediate Similarity	NPC188814
0.8226	Intermediate Similarity	NPC195262
0.8222	Intermediate Similarity	NPC255801
0.8222	Intermediate Similarity	NPC322301
0.8222	Intermediate Similarity	NPC87723
0.8209	Intermediate Similarity	NPC131039
0.8209	Intermediate Similarity	NPC299734
0.8209	Intermediate Similarity	NPC156092
0.8209	Intermediate Similarity	NPC101752
0.8209	Intermediate Similarity	NPC65005
0.8209	Intermediate Similarity	NPC191976
0.8209	Intermediate Similarity	NPC194764
0.8209	Intermediate Similarity	NPC264112
0.8209	Intermediate Similarity	NPC13575
0.8203	Intermediate Similarity	NPC10926
0.8195	Intermediate Similarity	NPC12070
0.8195	Intermediate Similarity	NPC270899
0.8182	Intermediate Similarity	NPC27490
0.8175	Intermediate Similarity	NPC92079
0.8175	Intermediate Similarity	NPC11056
0.8168	Intermediate Similarity	NPC259942
0.8162	Intermediate Similarity	NPC254168
0.8162	Intermediate Similarity	NPC248995
0.8162	Intermediate Similarity	NPC272844
0.816	Intermediate Similarity	NPC159525
0.8148	Intermediate Similarity	NPC25287
0.8148	Intermediate Similarity	NPC470983
0.8148	Intermediate Similarity	NPC249606
0.8148	Intermediate Similarity	NPC44960
0.8148	Intermediate Similarity	NPC274109
0.8148	Intermediate Similarity	NPC12165
0.8148	Intermediate Similarity	NPC150399
0.8148	Intermediate Similarity	NPC66349
0.8148	Intermediate Similarity	NPC98115
0.8148	Intermediate Similarity	NPC1486
0.8148	Intermediate Similarity	NPC174999
0.8148	Intermediate Similarity	NPC477243
0.8148	Intermediate Similarity	NPC168105
0.8148	Intermediate Similarity	NPC474110
0.8148	Intermediate Similarity	NPC477244
0.8148	Intermediate Similarity	NPC470982
0.8148	Intermediate Similarity	NPC477242
0.8148	Intermediate Similarity	NPC186838
0.8148	Intermediate Similarity	NPC41461
0.814	Intermediate Similarity	NPC8745
0.8134	Intermediate Similarity	NPC249272
0.8125	Intermediate Similarity	NPC13238
0.812	Intermediate Similarity	NPC267205
0.812	Intermediate Similarity	NPC180261
0.812	Intermediate Similarity	NPC103105
0.812	Intermediate Similarity	NPC37299
0.8115	Intermediate Similarity	NPC276111
0.8115	Intermediate Similarity	NPC118288
0.8102	Intermediate Similarity	NPC275903
0.8102	Intermediate Similarity	NPC240305
0.8092	Intermediate Similarity	NPC109123
0.8088	Intermediate Similarity	NPC138047
0.8088	Intermediate Similarity	NPC317119
0.8088	Intermediate Similarity	NPC131782
0.8088	Intermediate Similarity	NPC474624
0.8088	Intermediate Similarity	NPC472419
0.8088	Intermediate Similarity	NPC153979
0.808	Intermediate Similarity	NPC158222
0.8077	Intermediate Similarity	NPC83572
0.8074	Intermediate Similarity	NPC118919
0.806	Intermediate Similarity	NPC93756
0.806	Intermediate Similarity	NPC18877
0.806	Intermediate Similarity	NPC82225
0.806	Intermediate Similarity	NPC294593
0.806	Intermediate Similarity	NPC159623
0.806	Intermediate Similarity	NPC28753
0.806	Intermediate Similarity	NPC108113
0.806	Intermediate Similarity	NPC20560
0.806	Intermediate Similarity	NPC144051
0.806	Intermediate Similarity	NPC204960
0.8047	Intermediate Similarity	NPC174991
0.803	Intermediate Similarity	NPC17840

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 NPC66252 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	296
0.1-0.2	1073
0.2-0.3	2076
0.3-0.4	3053
0.4-0.5	1763
0.5-0.6	697
0.6-0.7	163
0.7-0.8	27
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9055	High Similarity	NPD6651	Approved
0.837	Intermediate Similarity	NPD2800	Approved
0.7941	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD7390	Discontinued
0.7817	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD943	Approved
0.7778	Intermediate Similarity	NPD1240	Approved
0.7692	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1607	Approved
0.7554	Intermediate Similarity	NPD1510	Phase 2
0.7448	Intermediate Similarity	NPD2534	Approved
0.7448	Intermediate Similarity	NPD2533	Approved
0.7448	Intermediate Similarity	NPD2532	Approved
0.7447	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4380	Phase 2
0.7394	Intermediate Similarity	NPD1549	Phase 2
0.7383	Intermediate Similarity	NPD7411	Suspended
0.7351	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD1164	Approved
0.7255	Intermediate Similarity	NPD7075	Discontinued
0.7254	Intermediate Similarity	NPD5405	Approved
0.7254	Intermediate Similarity	NPD5404	Approved
0.7254	Intermediate Similarity	NPD5408	Approved
0.7254	Intermediate Similarity	NPD5406	Approved
0.7219	Intermediate Similarity	NPD6801	Discontinued
0.7218	Intermediate Similarity	NPD1201	Approved
0.7171	Intermediate Similarity	NPD7819	Suspended
0.7133	Intermediate Similarity	NPD2935	Discontinued
0.7133	Intermediate Similarity	NPD2796	Approved
0.7132	Intermediate Similarity	NPD1470	Approved
0.7131	Intermediate Similarity	NPD846	Approved
0.7131	Intermediate Similarity	NPD940	Approved
0.7115	Intermediate Similarity	NPD6959	Discontinued
0.7086	Intermediate Similarity	NPD6599	Discontinued
0.7063	Intermediate Similarity	NPD9266	Approved
0.7063	Intermediate Similarity	NPD74	Approved
0.7059	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6799	Approved
0.7027	Intermediate Similarity	NPD1511	Approved
0.7023	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD9493	Approved
0.6993	Remote Similarity	NPD1934	Approved
0.6986	Remote Similarity	NPD1243	Approved
0.6984	Remote Similarity	NPD9264	Approved
0.6984	Remote Similarity	NPD9267	Approved
0.6984	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD9263	Approved
0.6981	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6232	Discontinued
0.6948	Remote Similarity	NPD2801	Approved
0.6939	Remote Similarity	NPD3750	Approved
0.6939	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7473	Discontinued
0.6933	Remote Similarity	NPD1512	Approved
0.6929	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD9269	Phase 2
0.6875	Remote Similarity	NPD4750	Phase 3
0.6871	Remote Similarity	NPD2654	Approved
0.6871	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD9268	Approved
0.686	Remote Similarity	NPD1809	Phase 2
0.6859	Remote Similarity	NPD3882	Suspended
0.6859	Remote Similarity	NPD7768	Phase 2
0.6855	Remote Similarity	NPD5711	Approved
0.6855	Remote Similarity	NPD5710	Approved
0.6852	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD2344	Approved
0.6828	Remote Similarity	NPD2799	Discontinued
0.6824	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2932	Approved
0.6791	Remote Similarity	NPD9545	Approved
0.6788	Remote Similarity	NPD3972	Approved
0.6781	Remote Similarity	NPD6099	Approved
0.6781	Remote Similarity	NPD6100	Approved
0.6776	Remote Similarity	NPD920	Approved
0.677	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6166	Phase 2
0.677	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5953	Discontinued
0.6761	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7286	Phase 2
0.6742	Remote Similarity	NPD9281	Approved
0.6736	Remote Similarity	NPD230	Phase 1
0.6709	Remote Similarity	NPD3749	Approved
0.6691	Remote Similarity	NPD3019	Approved
0.6688	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD9717	Approved
0.6667	Remote Similarity	NPD2309	Approved
0.6667	Remote Similarity	NPD9261	Approved
0.6667	Remote Similarity	NPD1551	Phase 2
0.6643	Remote Similarity	NPD2313	Discontinued
0.6643	Remote Similarity	NPD1203	Approved
0.6623	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3300	Phase 2
0.6606	Remote Similarity	NPD7074	Phase 3
0.6599	Remote Similarity	NPD3748	Approved
0.6596	Remote Similarity	NPD2798	Approved
0.6587	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3818	Discontinued
0.6582	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD5403	Approved
0.6545	Remote Similarity	NPD6020	Phase 2
0.6545	Remote Similarity	NPD7054	Approved
0.6541	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD6559	Discontinued
0.6522	Remote Similarity	NPD5494	Approved
0.6515	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD5124	Phase 1
0.6506	Remote Similarity	NPD7472	Approved
0.6503	Remote Similarity	NPD6832	Phase 2
0.649	Remote Similarity	NPD4628	Phase 3
0.6486	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD422	Phase 1
0.6474	Remote Similarity	NPD3226	Approved
0.6474	Remote Similarity	NPD7458	Discontinued
0.6467	Remote Similarity	NPD6797	Phase 2
0.6452	Remote Similarity	NPD2860	Approved
0.6452	Remote Similarity	NPD2859	Approved
0.6434	Remote Similarity	NPD4208	Discontinued
0.6429	Remote Similarity	NPD6104	Discontinued
0.6429	Remote Similarity	NPD5401	Approved
0.6429	Remote Similarity	NPD7251	Discontinued
0.6423	Remote Similarity	NPD845	Approved
0.6418	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD3268	Approved
0.6414	Remote Similarity	NPD3764	Approved
0.6407	Remote Similarity	NPD1729	Discontinued
0.6402	Remote Similarity	NPD3926	Phase 2
0.64	Remote Similarity	NPD2346	Discontinued
0.6391	Remote Similarity	NPD7808	Phase 3
0.6383	Remote Similarity	NPD1755	Approved
0.6382	Remote Similarity	NPD7003	Approved
0.6382	Remote Similarity	NPD3400	Discontinued
0.6378	Remote Similarity	NPD1242	Phase 1
0.6371	Remote Similarity	NPD2933	Approved
0.6371	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD2934	Approved
0.637	Remote Similarity	NPD520	Approved
0.637	Remote Similarity	NPD5951	Approved
0.6358	Remote Similarity	NPD919	Approved
0.6346	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD1465	Phase 2
0.6301	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD3020	Approved
0.6294	Remote Similarity	NPD2797	Approved
0.6294	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD3023	Approved
0.6286	Remote Similarity	NPD3026	Approved
0.628	Remote Similarity	NPD1247	Approved
0.6276	Remote Similarity	NPD4207	Discontinued
0.6273	Remote Similarity	NPD5402	Approved
0.6265	Remote Similarity	NPD2403	Approved
0.6259	Remote Similarity	NPD3025	Approved
0.6259	Remote Similarity	NPD3024	Approved
0.625	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5844	Phase 1
0.6241	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD1237	Approved
0.6215	Remote Similarity	NPD4363	Phase 3
0.6215	Remote Similarity	NPD4360	Phase 2
0.6214	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.619	Remote Similarity	NPD411	Approved
0.619	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.619	Remote Similarity	NPD1296	Phase 2
0.619	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD1759	Phase 1
0.618	Remote Similarity	NPD4361	Phase 2
0.618	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD1241	Discontinued
0.6176	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD447	Suspended
0.6173	Remote Similarity	NPD2296	Approved
0.6169	Remote Similarity	NPD8166	Discontinued
0.6164	Remote Similarity	NPD4908	Phase 1
0.6159	Remote Similarity	NPD7033	Discontinued
0.6159	Remote Similarity	NPD4308	Phase 3
0.6159	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4749	Approved
0.6154	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1929	Approved
0.6154	Remote Similarity	NPD1930	Approved
0.6149	Remote Similarity	NPD8150	Discontinued
0.6138	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD1758	Phase 1
0.6111	Remote Similarity	NPD1876	Approved
0.6102	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD4212	Discontinued

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