NPASS Compound

Structure

CID289432 OpenBabel06191716092D 21 24 0 0 1 0 0 0 0 0999 V2000 5.0133 -2.9285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8338 2.4471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8478 -0.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8480 -1.4458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0125 0.0014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3422 -1.9290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5064 -1.4467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0131 -1.9285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8341 1.4471 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.1778 -1.4462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1775 -0.4813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5061 -0.4818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6700 0.9648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3417 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5055 1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3414 0.9653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6703 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5053 2.4476 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2073 1.4656 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 9 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 9 1 0 0 0 0 5 12 2 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 21 1 0 0 0 0 9 11 2 0 0 0 0 10 14 1 0 0 0 0 11 12 1 0 0 0 0 12 15 1 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 17 1 0 0 0 0 16 17 1 0 0 0 0 16 19 2 0 0 0 0 17 20 2 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	278.09
Volume:	290.937
LogP:	5.327
LogD:	3.424
LogS:	-3.979
# Rotatable Bonds:	0
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.36
Synthetic Accessibility Score:	2.639
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.999
MDCK Permeability:	1.8711394659476355e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.09
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.786

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	98.0926742553711%
Volume Distribution (VD):	0.434
Pgp-substrate:	3.7846174240112305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.738
CYP2C19-inhibitor:	0.763
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.752
CYP2C9-substrate:	0.773
CYP2D6-inhibitor:	0.574
CYP2D6-substrate:	0.865
CYP3A4-inhibitor:	0.154
CYP3A4-substrate:	0.128

ADMET: Excretion

Clearance (CL):	9.253
Half-life (T1/2):	0.314

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.069
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.473
Rat Oral Acute Toxicity:	0.861
Maximum Recommended Daily Dose:	0.876
Skin Sensitization:	0.911
Carcinogencity:	0.95
Eye Corrosion:	0.008
Eye Irritation:	0.935
Respiratory Toxicity:	0.764

Download Data

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

Natural Product: NPC289432

Natural Product ID:	NPC289432
*Common Name:**	1,6-Dimethyl-1,2-Dihydronaphtho[1,2-G][1]Benzofuran-10,11-Dione
IUPAC Name:	1,6-dimethyl-1,2-dihydronaphtho[1,2-g][1]benzofuran-10,11-dione
Synonyms:
Standard InCHIKey:	HARGZZNYNSYSGJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14O3/c1-9-4-3-5-12-11(9)6-7-13-15(12)17(20)16(19)14-10(2)8-21-18(13)14/h3-7,10H,8H2,1-2H3
SMILES:	CC1COC2=C1C(=O)C(=O)c1c2ccc2c1cccc2C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1358724
PubChem CID:	5316743
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002548] Tanshinones, isotanshinones, and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473439]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141863]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17217287]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO14979	Salvia trijuga	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20515057]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27128895]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	Resinous Wood	n.a.	n.a.	PMID[29227647]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14979	Salvia trijuga	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14979	Salvia trijuga	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14979	Salvia trijuga	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30139	Salvia przewalskll	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14979	Salvia trijuga	Species	Lamiaceae	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	1
Others	2
Potency	29

Activity Type	# Activity
Cell Line	1
Individual Protein	28
Others	2
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	22387.2	nM	PMID[479527]
NPT46	Individual Protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	=	44668.4	nM	PMID[479527]
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	39810.7	nM	PMID[479527]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	19952.6	nM	PMID[479527]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	35481.3	nM	PMID[479527]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	39810.7	nM	PMID[479527]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	10000.0	nM	PMID[479527]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	7943.3	nM	PMID[479527]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	39810.7	nM	PMID[479527]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	28183.8	nM	PMID[479527]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	31622.8	nM	PMID[479527]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	3154.8	nM	PMID[479527]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	15848.9	nM	PMID[479527]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	17782.8	nM	PMID[479527]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	19952.6	nM	PMID[479527]
NPT58	Individual Protein	Bloom syndrome protein	Homo sapiens	Potency	=	28183.8	nM	PMID[479527]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	12589.3	nM	PMID[479527]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[479527]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	5623.4	nM	PMID[479527]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[479527]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[479527]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	4109.5	nM	PMID[479527]
NPT1078	Individual Protein	Indoleamine 2,3-dioxygenase	Homo sapiens	Inhibition	=	54.34	%	PMID[479528]
NPT1078	Individual Protein	Indoleamine 2,3-dioxygenase	Homo sapiens	IC50	=	1300.0	nM	PMID[479528]
NPT1229	Cell Line	Huh-7	Homo sapiens	Survival	=	94.72	%	PMID[479528]
NPT2	Others	Unspecified		Potency	=	31622.8	nM	PMID[479527]
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	39810.7	nM	PMID[479527]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	17782.8	nM	PMID[479527]
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	28183.8	nM	PMID[479527]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	28183.8	nM	PMID[479527]
NPT2	Others	Unspecified		Potency	n.a.	6309.6	nM	PMID[479527]

☑ 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 NPC289432 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	310
0.1-0.2	1394
0.2-0.3	2724
0.3-0.4	7792
0.4-0.5	12359
0.5-0.6	8906
0.6-0.7	8358
0.7-0.8	808
0.8-0.85	29
0.85-0.9	7
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC988
0.9912	High Similarity	NPC144547
0.9478	High Similarity	NPC77000
0.9478	High Similarity	NPC238861
0.9381	High Similarity	NPC135730
0.931	High Similarity	NPC232958
0.916	High Similarity	NPC51079
0.9123	High Similarity	NPC228936
0.9115	High Similarity	NPC13784
0.887	High Similarity	NPC477411
0.8793	High Similarity	NPC474095
0.8718	High Similarity	NPC226093
0.8707	High Similarity	NPC196075
0.8534	High Similarity	NPC212415
0.8475	Intermediate Similarity	NPC474408
0.8475	Intermediate Similarity	NPC470764
0.8462	Intermediate Similarity	NPC309056
0.845	Intermediate Similarity	NPC310662
0.8376	Intermediate Similarity	NPC79496
0.8291	Intermediate Similarity	NPC210089
0.8268	Intermediate Similarity	NPC428300
0.8264	Intermediate Similarity	NPC228318
0.8235	Intermediate Similarity	NPC67377
0.8231	Intermediate Similarity	NPC183103
0.8205	Intermediate Similarity	NPC273837
0.8197	Intermediate Similarity	NPC318173
0.819	Intermediate Similarity	NPC203732
0.8175	Intermediate Similarity	NPC295664
0.8106	Intermediate Similarity	NPC212207
0.8095	Intermediate Similarity	NPC318067
0.8083	Intermediate Similarity	NPC196673
0.8083	Intermediate Similarity	NPC241851
0.8083	Intermediate Similarity	NPC326664
0.8034	Intermediate Similarity	NPC470391
0.8	Intermediate Similarity	NPC57552
0.8	Intermediate Similarity	NPC128368
0.7984	Intermediate Similarity	NPC478162
0.7984	Intermediate Similarity	NPC478165
0.7983	Intermediate Similarity	NPC474057
0.7983	Intermediate Similarity	NPC291799
0.7971	Intermediate Similarity	NPC117674
0.797	Intermediate Similarity	NPC23894
0.7966	Intermediate Similarity	NPC83628
0.7966	Intermediate Similarity	NPC265407
0.7949	Intermediate Similarity	NPC37622
0.7949	Intermediate Similarity	NPC30594
0.7934	Intermediate Similarity	NPC307651
0.7907	Intermediate Similarity	NPC51292
0.7907	Intermediate Similarity	NPC177925
0.7895	Intermediate Similarity	NPC470406
0.7895	Intermediate Similarity	NPC59459
0.7886	Intermediate Similarity	NPC190298
0.7879	Intermediate Similarity	NPC279596
0.7879	Intermediate Similarity	NPC477412
0.7879	Intermediate Similarity	NPC239134
0.7869	Intermediate Similarity	NPC210092
0.7863	Intermediate Similarity	NPC471832
0.7863	Intermediate Similarity	NPC209632
0.7857	Intermediate Similarity	NPC472981
0.7857	Intermediate Similarity	NPC50872
0.7846	Intermediate Similarity	NPC51448
0.7846	Intermediate Similarity	NPC115797
0.7836	Intermediate Similarity	NPC474659
0.7833	Intermediate Similarity	NPC167504
0.7833	Intermediate Similarity	NPC137315
0.7833	Intermediate Similarity	NPC474157
0.7829	Intermediate Similarity	NPC476599
0.7829	Intermediate Similarity	NPC236405
0.7823	Intermediate Similarity	NPC222968
0.7823	Intermediate Similarity	NPC80605
0.7823	Intermediate Similarity	NPC61651
0.7823	Intermediate Similarity	NPC323440
0.7823	Intermediate Similarity	NPC45794
0.7812	Intermediate Similarity	NPC328107
0.781	Intermediate Similarity	NPC470407
0.7794	Intermediate Similarity	NPC186647
0.7786	Intermediate Similarity	NPC27798
0.7786	Intermediate Similarity	NPC93241
0.7778	Intermediate Similarity	NPC114594
0.7769	Intermediate Similarity	NPC474737
0.7769	Intermediate Similarity	NPC82899
0.7769	Intermediate Similarity	NPC186128
0.7769	Intermediate Similarity	NPC66208
0.7769	Intermediate Similarity	NPC270699
0.775	Intermediate Similarity	NPC214067
0.775	Intermediate Similarity	NPC196246
0.7746	Intermediate Similarity	NPC478163
0.7744	Intermediate Similarity	NPC164295
0.7739	Intermediate Similarity	NPC476042
0.7737	Intermediate Similarity	NPC233707
0.7727	Intermediate Similarity	NPC131684
0.7724	Intermediate Similarity	NPC221275
0.7721	Intermediate Similarity	NPC232996
0.7712	Intermediate Similarity	NPC134120
0.7705	Intermediate Similarity	NPC143768
0.7705	Intermediate Similarity	NPC272524
0.7704	Intermediate Similarity	NPC324117
0.7704	Intermediate Similarity	NPC1249
0.7698	Intermediate Similarity	NPC204784
0.7692	Intermediate Similarity	NPC89886
0.7692	Intermediate Similarity	NPC60679
0.7687	Intermediate Similarity	NPC477406
0.7687	Intermediate Similarity	NPC477407
0.7687	Intermediate Similarity	NPC472656
0.7686	Intermediate Similarity	NPC1082
0.7686	Intermediate Similarity	NPC265513
0.7686	Intermediate Similarity	NPC305912
0.7676	Intermediate Similarity	NPC281398
0.7674	Intermediate Similarity	NPC85511
0.7672	Intermediate Similarity	NPC42211
0.7672	Intermediate Similarity	NPC70624
0.7669	Intermediate Similarity	NPC27659
0.7667	Intermediate Similarity	NPC17417
0.7667	Intermediate Similarity	NPC192577
0.7667	Intermediate Similarity	NPC10251
0.7667	Intermediate Similarity	NPC269023
0.7667	Intermediate Similarity	NPC318327
0.7667	Intermediate Similarity	NPC474364
0.7667	Intermediate Similarity	NPC99846
0.7664	Intermediate Similarity	NPC119542
0.7661	Intermediate Similarity	NPC149691
0.7652	Intermediate Similarity	NPC96024
0.7652	Intermediate Similarity	NPC49994
0.7647	Intermediate Similarity	NPC119271
0.7647	Intermediate Similarity	NPC95485
0.7647	Intermediate Similarity	NPC88065
0.7647	Intermediate Similarity	NPC89504
0.7642	Intermediate Similarity	NPC308744
0.7638	Intermediate Similarity	NPC473243
0.7638	Intermediate Similarity	NPC476225
0.7638	Intermediate Similarity	NPC105709
0.763	Intermediate Similarity	NPC203486
0.763	Intermediate Similarity	NPC329913
0.7623	Intermediate Similarity	NPC280789
0.7623	Intermediate Similarity	NPC471188
0.7623	Intermediate Similarity	NPC292834
0.7615	Intermediate Similarity	NPC75432
0.7612	Intermediate Similarity	NPC472394
0.7606	Intermediate Similarity	NPC478160
0.7606	Intermediate Similarity	NPC478166
0.7603	Intermediate Similarity	NPC251854
0.7603	Intermediate Similarity	NPC93084
0.76	Intermediate Similarity	NPC158157
0.7591	Intermediate Similarity	NPC475549
0.7591	Intermediate Similarity	NPC471670
0.7589	Intermediate Similarity	NPC478164
0.7586	Intermediate Similarity	NPC118343
0.7583	Intermediate Similarity	NPC56493
0.7581	Intermediate Similarity	NPC306740
0.7581	Intermediate Similarity	NPC474685
0.7574	Intermediate Similarity	NPC274876
0.7574	Intermediate Similarity	NPC209858
0.7569	Intermediate Similarity	NPC474107
0.7565	Intermediate Similarity	NPC270654
0.7563	Intermediate Similarity	NPC172483
0.7561	Intermediate Similarity	NPC470253
0.7559	Intermediate Similarity	NPC202015
0.7557	Intermediate Similarity	NPC470765
0.7557	Intermediate Similarity	NPC294050
0.7557	Intermediate Similarity	NPC328997
0.7544	Intermediate Similarity	NPC5472
0.7542	Intermediate Similarity	NPC301943
0.7542	Intermediate Similarity	NPC474365
0.7542	Intermediate Similarity	NPC247976
0.754	Intermediate Similarity	NPC469954
0.7538	Intermediate Similarity	NPC228739
0.7538	Intermediate Similarity	NPC182646
0.7537	Intermediate Similarity	NPC470278
0.7535	Intermediate Similarity	NPC290038
0.7535	Intermediate Similarity	NPC114513
0.7535	Intermediate Similarity	NPC245522
0.7535	Intermediate Similarity	NPC308006
0.7521	Intermediate Similarity	NPC112552
0.752	Intermediate Similarity	NPC471616
0.7519	Intermediate Similarity	NPC269923
0.7519	Intermediate Similarity	NPC167323
0.7518	Intermediate Similarity	NPC217914
0.7518	Intermediate Similarity	NPC69755
0.75	Intermediate Similarity	NPC470753
0.75	Intermediate Similarity	NPC473220
0.75	Intermediate Similarity	NPC83409
0.75	Intermediate Similarity	NPC243059
0.75	Intermediate Similarity	NPC185763
0.75	Intermediate Similarity	NPC263817
0.75	Intermediate Similarity	NPC474264
0.75	Intermediate Similarity	NPC81135
0.75	Intermediate Similarity	NPC169913
0.75	Intermediate Similarity	NPC126516
0.75	Intermediate Similarity	NPC478159
0.75	Intermediate Similarity	NPC478161
0.75	Intermediate Similarity	NPC225060
0.75	Intermediate Similarity	NPC153053
0.75	Intermediate Similarity	NPC280827
0.7482	Intermediate Similarity	NPC475400
0.7482	Intermediate Similarity	NPC475104
0.7481	Intermediate Similarity	NPC199273
0.7481	Intermediate Similarity	NPC164014
0.7481	Intermediate Similarity	NPC246166
0.7481	Intermediate Similarity	NPC472693
0.7481	Intermediate Similarity	NPC111088

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 NPC289432 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	954
0.2-0.3	988
0.3-0.4	2565
0.4-0.5	2579
0.5-0.6	1338
0.6-0.7	389
0.7-0.8	39
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9478	High Similarity	NPD3412	Clinical (unspecified phase)
0.8534	High Similarity	NPD1609	Clinical (unspecified phase)
0.7983	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD1876	Approved
0.7727	Intermediate Similarity	NPD7008	Discontinued
0.7717	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD1651	Approved
0.7667	Intermediate Similarity	NPD2182	Approved
0.7656	Intermediate Similarity	NPD1281	Approved
0.7597	Intermediate Similarity	NPD3972	Approved
0.7586	Intermediate Similarity	NPD1238	Approved
0.7581	Intermediate Similarity	NPD5951	Approved
0.7482	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD2346	Discontinued
0.7481	Intermediate Similarity	NPD1283	Approved
0.7479	Intermediate Similarity	NPD164	Approved
0.7426	Intermediate Similarity	NPD2979	Phase 3
0.7414	Intermediate Similarity	NPD3495	Discontinued
0.7398	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD1930	Approved
0.7395	Intermediate Similarity	NPD1929	Approved
0.7395	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD6287	Discontinued
0.7364	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5909	Discontinued
0.7328	Intermediate Similarity	NPD1989	Approved
0.7328	Intermediate Similarity	NPD4878	Approved
0.7324	Intermediate Similarity	NPD7003	Approved
0.7252	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2798	Approved
0.7234	Intermediate Similarity	NPD1471	Phase 3
0.7222	Intermediate Similarity	NPD1241	Discontinued
0.719	Intermediate Similarity	NPD1237	Approved
0.7177	Intermediate Similarity	NPD2067	Discontinued
0.7167	Intermediate Similarity	NPD1932	Approved
0.7165	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD2438	Suspended
0.7163	Intermediate Similarity	NPD2531	Phase 2
0.7153	Intermediate Similarity	NPD3764	Approved
0.7153	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD7094	Approved
0.7143	Intermediate Similarity	NPD6858	Approved
0.7109	Intermediate Similarity	NPD3317	Approved
0.7103	Intermediate Similarity	NPD7236	Approved
0.7101	Intermediate Similarity	NPD7713	Phase 3
0.7097	Intermediate Similarity	NPD2329	Discontinued
0.7092	Intermediate Similarity	NPD2799	Discontinued
0.7075	Intermediate Similarity	NPD6273	Approved
0.7069	Intermediate Similarity	NPD7631	Approved
0.7047	Intermediate Similarity	NPD3226	Approved
0.7047	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3266	Approved
0.7037	Intermediate Similarity	NPD3267	Approved
0.7023	Intermediate Similarity	NPD5691	Approved
0.7	Intermediate Similarity	NPD2066	Phase 3
0.6993	Remote Similarity	NPD2344	Approved
0.6992	Remote Similarity	NPD1201	Approved
0.6985	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7609	Phase 3
0.698	Remote Similarity	NPD7239	Suspended
0.6978	Remote Similarity	NPD8032	Phase 2
0.6972	Remote Similarity	NPD3748	Approved
0.697	Remote Similarity	NPD17	Approved
0.697	Remote Similarity	NPD2932	Approved
0.6967	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.696	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6039	Approved
0.6949	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7458	Discontinued
0.693	Remote Similarity	NPD650	Approved
0.6929	Remote Similarity	NPD4307	Phase 2
0.6923	Remote Similarity	NPD2796	Approved
0.6917	Remote Similarity	NPD4879	Approved
0.6912	Remote Similarity	NPD1470	Approved
0.6897	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3024	Approved
0.6894	Remote Similarity	NPD3025	Approved
0.6884	Remote Similarity	NPD7055	Discontinued
0.6864	Remote Similarity	NPD1202	Approved
0.6864	Remote Similarity	NPD1563	Approved
0.6861	Remote Similarity	NPD2788	Approved
0.6849	Remote Similarity	NPD4628	Phase 3
0.6842	Remote Similarity	NPD5125	Phase 3
0.6842	Remote Similarity	NPD3019	Approved
0.6842	Remote Similarity	NPD5126	Approved
0.6818	Remote Similarity	NPD7009	Phase 2
0.6815	Remote Similarity	NPD1608	Approved
0.6803	Remote Similarity	NPD2309	Approved
0.6803	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD3023	Approved
0.6791	Remote Similarity	NPD3026	Approved
0.6788	Remote Similarity	NPD2797	Approved
0.6786	Remote Similarity	NPD3268	Approved
0.678	Remote Similarity	NPD1508	Approved
0.6769	Remote Similarity	NPD2629	Approved
0.6763	Remote Similarity	NPD6832	Phase 2
0.6759	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7819	Suspended
0.6742	Remote Similarity	NPD6065	Approved
0.6742	Remote Similarity	NPD7610	Discontinued
0.6741	Remote Similarity	NPD1611	Approved
0.6736	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4308	Phase 3
0.6735	Remote Similarity	NPD3750	Approved
0.6718	Remote Similarity	NPD4198	Discontinued
0.6716	Remote Similarity	NPD4626	Approved
0.6713	Remote Similarity	NPD1607	Approved
0.6695	Remote Similarity	NPD1239	Approved
0.6694	Remote Similarity	NPD1564	Approved
0.6694	Remote Similarity	NPD1566	Phase 3
0.6694	Remote Similarity	NPD1565	Approved
0.6692	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD9545	Approved
0.669	Remote Similarity	NPD4476	Approved
0.669	Remote Similarity	NPD4477	Approved
0.6667	Remote Similarity	NPD1693	Approved
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2532	Approved
0.6667	Remote Similarity	NPD2533	Approved
0.6667	Remote Similarity	NPD2534	Approved
0.6667	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5494	Approved
0.6646	Remote Similarity	NPD7473	Discontinued
0.6643	Remote Similarity	NPD4622	Approved
0.6643	Remote Similarity	NPD4618	Approved
0.6642	Remote Similarity	NPD5585	Approved
0.6642	Remote Similarity	NPD5327	Phase 3
0.664	Remote Similarity	NPD3046	Approved
0.664	Remote Similarity	NPD3048	Approved
0.664	Remote Similarity	NPD3047	Approved
0.6638	Remote Similarity	NPD1087	Approved
0.6622	Remote Similarity	NPD8166	Discontinued
0.6621	Remote Similarity	NPD1510	Phase 2
0.662	Remote Similarity	NPD6663	Approved
0.662	Remote Similarity	NPD7961	Discontinued
0.6619	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD6085	Phase 2
0.6617	Remote Similarity	NPD2347	Approved
0.6612	Remote Similarity	NPD1843	Approved
0.6604	Remote Similarity	NPD6959	Discontinued
0.6603	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD5977	Approved
0.6603	Remote Similarity	NPD5978	Approved
0.6599	Remote Similarity	NPD2897	Discontinued
0.6597	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD5667	Approved
0.6583	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6279	Approved
0.6581	Remote Similarity	NPD6280	Approved
0.6579	Remote Similarity	NPD3873	Phase 3
0.6579	Remote Similarity	NPD920	Approved
0.6579	Remote Similarity	NPD3869	Phase 3
0.6575	Remote Similarity	NPD2935	Discontinued
0.6575	Remote Similarity	NPD5406	Approved
0.6575	Remote Similarity	NPD5404	Approved
0.6575	Remote Similarity	NPD5405	Approved
0.6575	Remote Similarity	NPD5408	Approved
0.6573	Remote Similarity	NPD3142	Approved
0.6573	Remote Similarity	NPD3373	Approved
0.6573	Remote Similarity	NPD1240	Approved
0.6573	Remote Similarity	NPD3140	Approved
0.6571	Remote Similarity	NPD5736	Approved
0.6567	Remote Similarity	NPD7741	Discontinued
0.6567	Remote Similarity	NPD1894	Discontinued
0.6565	Remote Similarity	NPD6010	Discontinued
0.6565	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6232	Discontinued
0.6561	Remote Similarity	NPD7058	Phase 2
0.6561	Remote Similarity	NPD7057	Phase 3
0.6556	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1243	Approved
0.6552	Remote Similarity	NPD5688	Approved
0.6552	Remote Similarity	NPD9259	Approved
0.6552	Remote Similarity	NPD9257	Approved
0.6552	Remote Similarity	NPD5689	Approved
0.6549	Remote Similarity	NPD942	Approved
0.6544	Remote Similarity	NPD3897	Approved
0.6544	Remote Similarity	NPD3898	Approved
0.6544	Remote Similarity	NPD3896	Approved
0.6544	Remote Similarity	NPD3895	Approved
0.6533	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6355	Discontinued
0.6522	Remote Similarity	NPD5157	Phase 1
0.6522	Remote Similarity	NPD5159	Phase 2
0.6522	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD5239	Approved
0.6512	Remote Similarity	NPD5236	Approved
0.6512	Remote Similarity	NPD5235	Approved
0.6512	Remote Similarity	NPD5240	Approved
0.6512	Remote Similarity	NPD5237	Approved
0.6504	Remote Similarity	NPD5926	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