NPASS Compound

Structure

CID10051 OpenBabel06191715332D 23 26 0 0 1 0 0 0 0 0999 V2000 -0.8338 -2.4471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0133 2.9285 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 -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 -5.8478 0.4808 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 -0.8341 -1.4471 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 -4.1778 1.4462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8480 1.4458 0.0000 C 0 0 2 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 -5.0131 1.9285 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7143 1.9454 0.0000 O 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 -5.8791 2.4285 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 8 1 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 6 1 0 0 0 0 4 9 1 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 8 2 0 0 0 0 7 23 1 0 0 0 0 8 13 1 0 0 0 0 9 11 2 0 0 0 0 9 14 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 18 1 1 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 17 2 0 0 0 0 14 16 1 0 0 0 0 15 16 1 0 0 0 0 15 20 2 0 0 0 0 16 21 2 0 0 0 0 17 23 1 0 0 0 0 18 2 1 1 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.1
Volume:	311.154
LogP:	2.013
LogD:	2.108
LogS:	-4.567
# Rotatable Bonds:	0
TPSA:	87.74
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.728
Synthetic Accessibility Score:	3.921
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.066
MDCK Permeability:	1.1043871381843928e-05
Pgp-inhibitor:	0.214
Pgp-substrate:	0.515
Human Intestinal Absorption (HIA):	0.062
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	96.5273666381836%
Volume Distribution (VD):	1.877
Pgp-substrate:	1.8107918500900269%

ADMET: Metabolism

CYP1A2-inhibitor:	0.869
CYP1A2-substrate:	0.209
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.348
CYP2C9-substrate:	0.207
CYP2D6-inhibitor:	0.111
CYP2D6-substrate:	0.282
CYP3A4-inhibitor:	0.337
CYP3A4-substrate:	0.169

ADMET: Excretion

Clearance (CL):	4.608
Half-life (T1/2):	0.106

ADMET: Toxicity

hERG Blockers:	0.123
Human Hepatotoxicity (H-HT):	0.377
Drug-inuced Liver Injury (DILI):	0.886
AMES Toxicity:	0.833
Rat Oral Acute Toxicity:	0.938
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.296
Carcinogencity:	0.792
Eye Corrosion:	0.003
Eye Irritation:	0.081
Respiratory Toxicity:	0.771

Download Data

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

Natural Product: NPC10051

Natural Product ID:	NPC10051
*Common Name:**	Tanshindiol C
IUPAC Name:	(6R,7R)-6,7-dihydroxy-1,6-dimethyl-8,9-dihydro-7H-naphtho[1,2-g][1]benzofuran-10,11-dione
Synonyms:
Standard InCHIKey:	RTKDBIDPGKCZJS-KZULUSFZSA-N
Standard InCHI:	InChI=1S/C18H16O5/c1-8-7-23-17-10-3-5-11-9(4-6-12(19)18(11,2)22)14(10)16(21)15(20)13(8)17/h3,5,7,12,19,22H,4,6H2,1-2H3/t12-,18-/m1/s1
SMILES:	O[C@@H]1CCc2c([C@@]1(C)O)ccc1c2C(=O)C(=O)c2c1occ2C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3287734
PubChem CID:	126072
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]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880325]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1567426]
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]
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]
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]
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]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO24740	Uvaria klaineana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28257	Dioscorea communis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12476	Delphinium cyphoplectrum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26223	Cladonia bellidiflora	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23417	Rhabdia lycioides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6346	Phallusia fumigata	Species	Ascidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25974	Streptomyces lateritius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10497	Hydrolithon reinboldii	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO415	Deguelia hatschbachii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24988	Viburnum sieboldi	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4009	Allochromatium minutissimum	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22016	0tholaena dealbata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23960	Artemisia siversiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26054	Palmaria palmata	Species	Palmariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24740	Uvaria klaineana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25868	Decachaeta ovatifolia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26087	Euphorbia retusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27437	Camptothecium lutescens	Species	Brachytheciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25212	Ritterella rubra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10155	Stauntonia obovatifoliola	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28257	Dioscorea communis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26316	Pleurophycus gardneri	Species	Alariaceae	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	7
IC50	1
Ki	2
Others	14

Activity Type	# Activity
Cell Line	4
Individual Protein	2
NON-MOLECULAR	3
Others	13
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT464	Cell Line	Daudi	Homo sapiens	GI50	=	10600.0	nM	PMID[526684]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	4000.0	nM	PMID[526684]
NPT1125	Cell Line	T98G	Homo sapiens	GI50	=	6000.0	nM	PMID[526684]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	4200.0	nM	PMID[526684]
NPT1126	Individual Protein	Histone-lysine N-methyltransferase EZH2	Homo sapiens	Inhibition	=	50.0	%	PMID[526684]
NPT1123	Protein Complex	EZH2/SUZ12/EED complex	Homo sapiens	IC50	=	550.0	nM	PMID[526684]
NPT1124	Protein Complex	EZH2/SUZ12/EED/RBBP7/RBBP4	Homo sapiens	Ki	=	194.0	nM	PMID[526684]
NPT2	Others	Unspecified		Ki	=	176.0	nM	PMID[526684]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	1500.0	nM	PMID[526684]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	9500.0	nM	PMID[526684]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	5700.0	nM	PMID[526684]
NPT610	Others	Molecular identity unknown		Activity	=	11.0	%	PMID[526684]
NPT610	Others	Molecular identity unknown		Activity	=	13.0	%	PMID[526684]
NPT610	Others	Molecular identity unknown		Activity	=	21.0	%	PMID[526684]
NPT610	Others	Molecular identity unknown		Activity	=	58.0	%	PMID[526684]
NPT610	Others	Molecular identity unknown		Activity	=	51.0	%	PMID[526684]
NPT610	Others	Molecular identity unknown		Activity	=	41.0	%	PMID[526684]
NPT610	Others	Molecular identity unknown		Activity	=	20.0	%	PMID[526684]
NPT610	Others	Molecular identity unknown		Activity	=	24.0	%	PMID[526684]
NPT610	Others	Molecular identity unknown		Activity	=	29.0	%	PMID[526684]
NPT610	Others	Molecular identity unknown		Activity	=	7.0	%	PMID[526684]

☑ 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 NPC10051 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	362
0.1-0.2	1507
0.2-0.3	3213
0.3-0.4	8309
0.4-0.5	10777
0.5-0.6	5048
0.6-0.7	7173
0.7-0.8	6170
0.8-0.85	107
0.85-0.9	20
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC299094
0.9536	High Similarity	NPC179170
0.9404	High Similarity	NPC145830
0.9286	High Similarity	NPC221992
0.9156	High Similarity	NPC88958
0.9073	High Similarity	NPC281398
0.9067	High Similarity	NPC93241
0.9067	High Similarity	NPC27798
0.9	High Similarity	NPC117674
0.8961	High Similarity	NPC144010
0.8889	High Similarity	NPC44602
0.8782	High Similarity	NPC471613
0.8645	High Similarity	NPC478018
0.8625	High Similarity	NPC217602
0.8625	High Similarity	NPC317900
0.8625	High Similarity	NPC473282
0.8625	High Similarity	NPC104380
0.8625	High Similarity	NPC294300
0.8625	High Similarity	NPC476404
0.859	High Similarity	NPC280025
0.859	High Similarity	NPC192069
0.858	High Similarity	NPC472780
0.858	High Similarity	NPC472783
0.858	High Similarity	NPC269117
0.8571	High Similarity	NPC287559
0.8553	High Similarity	NPC290927
0.8537	High Similarity	NPC472784
0.8537	High Similarity	NPC136641
0.8519	High Similarity	NPC472781
0.8519	High Similarity	NPC472782
0.8519	High Similarity	NPC18986
0.8509	High Similarity	NPC140952
0.8506	High Similarity	NPC53016
0.8497	Intermediate Similarity	NPC52412
0.8485	Intermediate Similarity	NPC255787
0.8476	Intermediate Similarity	NPC121995
0.8447	Intermediate Similarity	NPC81405
0.8447	Intermediate Similarity	NPC478223
0.8438	Intermediate Similarity	NPC475770
0.8438	Intermediate Similarity	NPC474000
0.8424	Intermediate Similarity	NPC41689
0.8415	Intermediate Similarity	NPC56358
0.8408	Intermediate Similarity	NPC252208
0.8397	Intermediate Similarity	NPC478019
0.8397	Intermediate Similarity	NPC233763
0.8387	Intermediate Similarity	NPC158871
0.8375	Intermediate Similarity	NPC44606
0.8366	Intermediate Similarity	NPC18904
0.8363	Intermediate Similarity	NPC104682
0.8344	Intermediate Similarity	NPC476349
0.8344	Intermediate Similarity	NPC476350
0.8344	Intermediate Similarity	NPC472299
0.8333	Intermediate Similarity	NPC114513
0.8333	Intermediate Similarity	NPC245522
0.8323	Intermediate Similarity	NPC42458
0.8323	Intermediate Similarity	NPC158261
0.8323	Intermediate Similarity	NPC186392
0.8313	Intermediate Similarity	NPC270312
0.8302	Intermediate Similarity	NPC226578
0.8301	Intermediate Similarity	NPC265181
0.8293	Intermediate Similarity	NPC470810
0.8282	Intermediate Similarity	NPC260902
0.8282	Intermediate Similarity	NPC296957
0.8282	Intermediate Similarity	NPC123153
0.828	Intermediate Similarity	NPC478166
0.8263	Intermediate Similarity	NPC296558
0.8263	Intermediate Similarity	NPC191012
0.8261	Intermediate Similarity	NPC164912
0.8261	Intermediate Similarity	NPC24232
0.8253	Intermediate Similarity	NPC100849
0.8253	Intermediate Similarity	NPC308156
0.8246	Intermediate Similarity	NPC295914
0.8242	Intermediate Similarity	NPC24761
0.8242	Intermediate Similarity	NPC283209
0.8221	Intermediate Similarity	NPC160015
0.8221	Intermediate Similarity	NPC247677
0.8221	Intermediate Similarity	NPC213401
0.8221	Intermediate Similarity	NPC7059
0.8217	Intermediate Similarity	NPC79627
0.8214	Intermediate Similarity	NPC473945
0.821	Intermediate Similarity	NPC469966
0.821	Intermediate Similarity	NPC208806
0.821	Intermediate Similarity	NPC23559
0.8205	Intermediate Similarity	NPC69755
0.8199	Intermediate Similarity	NPC121615
0.8199	Intermediate Similarity	NPC294511
0.8199	Intermediate Similarity	NPC118427
0.8187	Intermediate Similarity	NPC228842
0.8187	Intermediate Similarity	NPC472298
0.8182	Intermediate Similarity	NPC233707
0.8182	Intermediate Similarity	NPC68848
0.8182	Intermediate Similarity	NPC79571
0.8176	Intermediate Similarity	NPC469425
0.8171	Intermediate Similarity	NPC246647
0.8171	Intermediate Similarity	NPC96342
0.8171	Intermediate Similarity	NPC212967
0.8171	Intermediate Similarity	NPC164110
0.816	Intermediate Similarity	NPC478159
0.816	Intermediate Similarity	NPC478161
0.8155	Intermediate Similarity	NPC53640
0.8155	Intermediate Similarity	NPC291742
0.8153	Intermediate Similarity	NPC163948
0.8148	Intermediate Similarity	NPC263676
0.8148	Intermediate Similarity	NPC154683
0.8148	Intermediate Similarity	NPC40356
0.8148	Intermediate Similarity	NPC282793
0.8148	Intermediate Similarity	NPC10429
0.8144	Intermediate Similarity	NPC101769
0.8144	Intermediate Similarity	NPC472581
0.8141	Intermediate Similarity	NPC263337
0.8133	Intermediate Similarity	NPC288602
0.8133	Intermediate Similarity	NPC45124
0.8133	Intermediate Similarity	NPC74854
0.8133	Intermediate Similarity	NPC88841
0.8133	Intermediate Similarity	NPC30655
0.8133	Intermediate Similarity	NPC285567
0.8129	Intermediate Similarity	NPC470407
0.8129	Intermediate Similarity	NPC98776
0.8125	Intermediate Similarity	NPC474107
0.8125	Intermediate Similarity	NPC95526
0.8121	Intermediate Similarity	NPC8389
0.8121	Intermediate Similarity	NPC472877
0.8114	Intermediate Similarity	NPC472662
0.8114	Intermediate Similarity	NPC472663
0.8113	Intermediate Similarity	NPC302987
0.811	Intermediate Similarity	NPC304692
0.811	Intermediate Similarity	NPC194499
0.811	Intermediate Similarity	NPC180924
0.8103	Intermediate Similarity	NPC475996
0.8098	Intermediate Similarity	NPC84721
0.8098	Intermediate Similarity	NPC472786
0.8098	Intermediate Similarity	NPC122365
0.8095	Intermediate Similarity	NPC38914
0.8089	Intermediate Similarity	NPC476946
0.8089	Intermediate Similarity	NPC329493
0.8086	Intermediate Similarity	NPC149526
0.8086	Intermediate Similarity	NPC473201
0.8086	Intermediate Similarity	NPC156244
0.8086	Intermediate Similarity	NPC470569
0.8086	Intermediate Similarity	NPC144283
0.8086	Intermediate Similarity	NPC302783
0.8086	Intermediate Similarity	NPC474417
0.8084	Intermediate Similarity	NPC478229
0.8084	Intermediate Similarity	NPC219861
0.8081	Intermediate Similarity	NPC472665
0.8075	Intermediate Similarity	NPC478219
0.8072	Intermediate Similarity	NPC188649
0.8072	Intermediate Similarity	NPC49009
0.807	Intermediate Similarity	NPC472584
0.8061	Intermediate Similarity	NPC268360
0.8059	Intermediate Similarity	NPC294512
0.8059	Intermediate Similarity	NPC53252
0.8057	Intermediate Similarity	NPC228209
0.805	Intermediate Similarity	NPC73416
0.805	Intermediate Similarity	NPC160777
0.8049	Intermediate Similarity	NPC41880
0.8049	Intermediate Similarity	NPC104736
0.8049	Intermediate Similarity	NPC148938
0.8039	Intermediate Similarity	NPC324117
0.8037	Intermediate Similarity	NPC285623
0.8037	Intermediate Similarity	NPC67654
0.8037	Intermediate Similarity	NPC137125
0.8037	Intermediate Similarity	NPC3744
0.8035	Intermediate Similarity	NPC475233
0.8025	Intermediate Similarity	NPC290954
0.8025	Intermediate Similarity	NPC470568
0.8025	Intermediate Similarity	NPC255641
0.8024	Intermediate Similarity	NPC478222
0.8024	Intermediate Similarity	NPC14822
0.8024	Intermediate Similarity	NPC472346
0.8023	Intermediate Similarity	NPC277510
0.8023	Intermediate Similarity	NPC199357
0.8013	Intermediate Similarity	NPC1268
0.8012	Intermediate Similarity	NPC470998
0.8012	Intermediate Similarity	NPC228501
0.8012	Intermediate Similarity	NPC226287
0.8012	Intermediate Similarity	NPC120220
0.8012	Intermediate Similarity	NPC131866
0.8	Intermediate Similarity	NPC241820
0.8	Intermediate Similarity	NPC88007
0.8	Intermediate Similarity	NPC476459
0.8	Intermediate Similarity	NPC300540
0.8	Intermediate Similarity	NPC150131
0.8	Intermediate Similarity	NPC472660
0.8	Intermediate Similarity	NPC177262
0.8	Intermediate Similarity	NPC50394
0.8	Intermediate Similarity	NPC473094
0.8	Intermediate Similarity	NPC39361
0.7989	Intermediate Similarity	NPC60848
0.7988	Intermediate Similarity	NPC169990
0.7988	Intermediate Similarity	NPC1477
0.7988	Intermediate Similarity	NPC210942
0.7988	Intermediate Similarity	NPC213608
0.7988	Intermediate Similarity	NPC25351
0.7988	Intermediate Similarity	NPC291110
0.7988	Intermediate Similarity	NPC214632
0.7988	Intermediate Similarity	NPC235333
0.7988	Intermediate Similarity	NPC329844
0.7988	Intermediate Similarity	NPC279768
0.7987	Intermediate Similarity	NPC469385

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 NPC10051 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	940
0.2-0.3	1496
0.3-0.4	2630
0.4-0.5	2159
0.5-0.6	1105
0.6-0.7	390
0.7-0.8	110
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
0.8301	Intermediate Similarity	NPD1471	Phase 3
0.8182	Intermediate Similarity	NPD2344	Approved
0.8075	Intermediate Similarity	NPD3226	Approved
0.8	Intermediate Similarity	NPD8434	Phase 2
0.7975	Intermediate Similarity	NPD2309	Approved
0.7949	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD2346	Discontinued
0.7816	Intermediate Similarity	NPD6559	Discontinued
0.7736	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD4628	Phase 3
0.7688	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD5760	Phase 2
0.7665	Intermediate Similarity	NPD5761	Phase 2
0.7665	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD3749	Approved
0.7619	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6959	Discontinued
0.7595	Intermediate Similarity	NPD2799	Discontinued
0.756	Intermediate Similarity	NPD7819	Suspended
0.7558	Intermediate Similarity	NPD6232	Discontinued
0.7548	Intermediate Similarity	NPD2313	Discontinued
0.7545	Intermediate Similarity	NPD7411	Suspended
0.7543	Intermediate Similarity	NPD5844	Phase 1
0.7529	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4380	Phase 2
0.7471	Intermediate Similarity	NPD3882	Suspended
0.7457	Intermediate Similarity	NPD6808	Phase 2
0.7456	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6273	Approved
0.7442	Intermediate Similarity	NPD5494	Approved
0.7432	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7075	Discontinued
0.7412	Intermediate Similarity	NPD2296	Approved
0.7412	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD920	Approved
0.7396	Intermediate Similarity	NPD6801	Discontinued
0.7396	Intermediate Similarity	NPD6280	Approved
0.7396	Intermediate Similarity	NPD6279	Approved
0.7396	Intermediate Similarity	NPD1934	Approved
0.7394	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2533	Approved
0.7394	Intermediate Similarity	NPD2532	Approved
0.7394	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2534	Approved
0.7386	Intermediate Similarity	NPD3818	Discontinued
0.7384	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7003	Approved
0.7346	Intermediate Similarity	NPD1549	Phase 2
0.7333	Intermediate Similarity	NPD8313	Approved
0.7333	Intermediate Similarity	NPD8312	Approved
0.7329	Intermediate Similarity	NPD2796	Approved
0.7322	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7458	Discontinued
0.7314	Intermediate Similarity	NPD3926	Phase 2
0.7303	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD3751	Discontinued
0.7284	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD919	Approved
0.7278	Intermediate Similarity	NPD6599	Discontinued
0.7273	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6166	Phase 2
0.7273	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3972	Approved
0.7251	Intermediate Similarity	NPD2801	Approved
0.7226	Intermediate Similarity	NPD1470	Approved
0.7225	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6765	Approved
0.7222	Intermediate Similarity	NPD2935	Discontinued
0.7222	Intermediate Similarity	NPD6764	Approved
0.7195	Intermediate Similarity	NPD2800	Approved
0.7186	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2798	Approved
0.7168	Intermediate Similarity	NPD7768	Phase 2
0.7161	Intermediate Similarity	NPD1876	Approved
0.716	Intermediate Similarity	NPD1510	Phase 2
0.7158	Intermediate Similarity	NPD6778	Approved
0.7158	Intermediate Similarity	NPD6781	Approved
0.7158	Intermediate Similarity	NPD6776	Approved
0.7158	Intermediate Similarity	NPD6782	Approved
0.7158	Intermediate Similarity	NPD6780	Approved
0.7158	Intermediate Similarity	NPD6777	Approved
0.7158	Intermediate Similarity	NPD6779	Approved
0.7152	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1607	Approved
0.7126	Intermediate Similarity	NPD6799	Approved
0.7126	Intermediate Similarity	NPD1511	Approved
0.712	Intermediate Similarity	NPD8150	Discontinued
0.7117	Intermediate Similarity	NPD1551	Phase 2
0.7107	Intermediate Similarity	NPD3764	Approved
0.7107	Intermediate Similarity	NPD3268	Approved
0.7105	Intermediate Similarity	NPD1651	Approved
0.7095	Intermediate Similarity	NPD7177	Discontinued
0.7091	Intermediate Similarity	NPD1243	Approved
0.7079	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6784	Approved
0.7065	Intermediate Similarity	NPD6785	Approved
0.7062	Intermediate Similarity	NPD3787	Discontinued
0.7056	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7033	Discontinued
0.7055	Intermediate Similarity	NPD4308	Phase 3
0.7051	Intermediate Similarity	NPD1283	Approved
0.7047	Intermediate Similarity	NPD7435	Discontinued
0.7041	Intermediate Similarity	NPD1512	Approved
0.7025	Intermediate Similarity	NPD9494	Approved
0.7019	Intermediate Similarity	NPD1240	Approved
0.7017	Intermediate Similarity	NPD7074	Phase 3
0.7012	Intermediate Similarity	NPD5405	Approved
0.7012	Intermediate Similarity	NPD5404	Approved
0.7012	Intermediate Similarity	NPD5406	Approved
0.7012	Intermediate Similarity	NPD5408	Approved
0.7011	Intermediate Similarity	NPD5402	Approved
0.7011	Intermediate Similarity	NPD3817	Phase 2
0.7	Intermediate Similarity	NPD5403	Approved
0.7	Intermediate Similarity	NPD6798	Discontinued
0.6994	Remote Similarity	NPD6844	Discontinued
0.6984	Remote Similarity	NPD6535	Approved
0.6984	Remote Similarity	NPD6534	Approved
0.6982	Remote Similarity	NPD4662	Approved
0.6982	Remote Similarity	NPD4661	Approved
0.6981	Remote Similarity	NPD6832	Phase 2
0.6975	Remote Similarity	NPD6355	Discontinued
0.6973	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1201	Approved
0.6961	Remote Similarity	NPD7054	Approved
0.6959	Remote Similarity	NPD7696	Phase 3
0.6959	Remote Similarity	NPD7698	Approved
0.6959	Remote Similarity	NPD7697	Approved
0.6948	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD3750	Approved
0.6928	Remote Similarity	NPD2424	Discontinued
0.6927	Remote Similarity	NPD8285	Discontinued
0.6923	Remote Similarity	NPD7390	Discontinued
0.6923	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7472	Approved
0.6923	Remote Similarity	NPD7870	Phase 2
0.6923	Remote Similarity	NPD7871	Phase 2
0.6919	Remote Similarity	NPD2651	Approved
0.6919	Remote Similarity	NPD2649	Approved
0.6914	Remote Similarity	NPD2979	Phase 3
0.6914	Remote Similarity	NPD4060	Phase 1
0.6909	Remote Similarity	NPD2438	Suspended
0.6906	Remote Similarity	NPD2163	Approved
0.6904	Remote Similarity	NPD7701	Phase 2
0.6902	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1203	Approved
0.6897	Remote Similarity	NPD37	Approved
0.6891	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6797	Phase 2
0.6885	Remote Similarity	NPD3823	Discontinued
0.6882	Remote Similarity	NPD5401	Approved
0.6881	Remote Similarity	NPD8404	Phase 2
0.6875	Remote Similarity	NPD7700	Phase 2
0.6875	Remote Similarity	NPD7699	Phase 2
0.6875	Remote Similarity	NPD4967	Phase 2
0.6875	Remote Similarity	NPD4966	Approved
0.6875	Remote Similarity	NPD4965	Approved
0.6872	Remote Similarity	NPD5710	Approved
0.6872	Remote Similarity	NPD5711	Approved
0.6871	Remote Similarity	NPD447	Suspended
0.6869	Remote Similarity	NPD8151	Discontinued
0.6862	Remote Similarity	NPD4287	Approved
0.6859	Remote Similarity	NPD1281	Approved
0.6855	Remote Similarity	NPD5647	Approved
0.6848	Remote Similarity	NPD7251	Discontinued
0.6842	Remote Similarity	NPD6213	Phase 3
0.6842	Remote Similarity	NPD6212	Phase 3
0.6842	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5049	Phase 3
0.6839	Remote Similarity	NPD5890	Approved
0.6839	Remote Similarity	NPD5889	Approved
0.6834	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD7874	Approved
0.6832	Remote Similarity	NPD7008	Discontinued
0.6826	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6823	Phase 2
0.6816	Remote Similarity	NPD8127	Discontinued
0.6816	Remote Similarity	NPD7199	Phase 2
0.6815	Remote Similarity	NPD9717	Approved
0.6811	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD7808	Phase 3
0.681	Remote Similarity	NPD4307	Phase 2
0.681	Remote Similarity	NPD4140	Approved
0.6807	Remote Similarity	NPD6099	Approved
0.6807	Remote Similarity	NPD4477	Approved
0.6807	Remote Similarity	NPD6100	Approved
0.6807	Remote Similarity	NPD4476	Approved
0.6805	Remote Similarity	NPD3887	Approved
0.6805	Remote Similarity	NPD2354	Approved
0.68	Remote Similarity	NPD7783	Phase 2
0.68	Remote Similarity	NPD7577	Discontinued
0.68	Remote Similarity	NPD7801	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