NPASS Compound

Structure

CID309056 OpenBabel06191716112D 25 28 0 0 1 0 0 0 0 0999 V2000 1.6812 -3.9153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5214 1.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3582 2.0826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5202 -1.4541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5205 -2.4244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6803 -0.9692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0008 -2.9102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8396 -2.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8396 0.4851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3601 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6809 -2.9098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5211 0.4844 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6377 1.4335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8410 -2.4249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8407 -1.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8399 -1.4551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6806 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6804 -0.9702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8405 0.4849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2846 1.7329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8407 1.4849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3598 -0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 3 13 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 11 1 0 0 0 0 6 15 2 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 25 1 0 0 0 0 11 14 2 0 0 0 0 12 2 1 6 0 0 0 12 17 1 0 0 0 0 13 22 2 0 0 0 0 14 15 1 0 0 0 0 15 18 1 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 25 1 0 0 0 0 20 21 1 0 0 0 0 20 23 2 0 0 0 0 21 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.14
Volume:	351.616
LogP:	3.537
LogD:	3.099
LogS:	-4.888
# Rotatable Bonds:	2
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.914
Synthetic Accessibility Score:	3.847
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.814
MDCK Permeability:	3.058738002437167e-05
Pgp-inhibitor:	0.075
Pgp-substrate:	0.08
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.08
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.314
Plasma Protein Binding (PPB):	96.6848373413086%
Volume Distribution (VD):	1.246
Pgp-substrate:	1.7457373142242432%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.854
CYP2C19-inhibitor:	0.958
CYP2C19-substrate:	0.599
CYP2C9-inhibitor:	0.856
CYP2C9-substrate:	0.158
CYP2D6-inhibitor:	0.958
CYP2D6-substrate:	0.207
CYP3A4-inhibitor:	0.898
CYP3A4-substrate:	0.672

ADMET: Excretion

Clearance (CL):	1.472
Half-life (T1/2):	0.05

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.746
Drug-inuced Liver Injury (DILI):	0.864
AMES Toxicity:	0.775
Rat Oral Acute Toxicity:	0.363
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.475
Carcinogencity:	0.916
Eye Corrosion:	0.003
Eye Irritation:	0.138
Respiratory Toxicity:	0.85

Download Data

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

Natural Product: NPC309056

Natural Product ID:	NPC309056
*Common Name:**	(1R,10S)-10-Hydroxy-1,6-Dimethyl-10-(2-Oxopropyl)-1,2-Dihydronaphtho[1,2-G][1]Benzofuran-11-One
IUPAC Name:	(1R,10S)-10-hydroxy-1,6-dimethyl-10-(2-oxopropyl)-1,2-dihydronaphtho[1,2-g][1]benzofuran-11-one
Synonyms:
Standard InCHIKey:	WQYKPUPMMFGHQW-QKVFXAPYSA-N
Standard InCHI:	InChI=1S/C21H20O4/c1-11-5-4-6-15-14(11)7-8-16-18(15)21(24,9-13(3)22)20(23)17-12(2)10-25-19(16)17/h4-8,12,24H,9-10H2,1-3H3/t12-,21-/m0/s1
SMILES:	CC(=O)C[C@@]1(O)C(=O)C2=C(c3c1c1cccc(c1cc3)C)OC[C@@H]2C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2261306
PubChem CID:	3083514
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]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24740	Uvaria klaineana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28257	Dioscorea communis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25813	Salvia przewalskii	Species	Lamiaceae	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]
NPO11003	Euphorbia sancta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26223	Cladonia bellidiflora	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28257	Dioscorea communis	Species	Dioscoreaceae	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]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6346	Phallusia fumigata	Species	Ascidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11985	Glycyrrhiza triphylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12476	Delphinium cyphoplectrum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25974	Streptomyces lateritius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11487	Senecio madagascariensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27437	Camptothecium lutescens	Species	Brachytheciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO415	Deguelia hatschbachii	Species	Fabaceae	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]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24988	Viburnum sieboldi	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10155	Stauntonia obovatifoliola	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6321	Agathosma thymifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28189	Metzgeria pubescens	Species	Metzgeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO191	Amaranthus hybr	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4009	Allochromatium minutissimum	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26316	Pleurophycus gardneri	Species	Alariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14253	Bothriocline longipes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10497	Hydrolithon reinboldii	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22016	0tholaena dealbata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13164	Iris hoogiana	Species	Iridaceae	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]
NPO12800	Glycine falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26087	Euphorbia retusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22758	Picradeniopsis pringlei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23960	Artemisia siversiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11814	Asphodeline tenuior	Species	Asphodelaceae	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

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	100.0	nM	PMID[530018]

☑ 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 NPC309056 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	296
0.1-0.2	1231
0.2-0.3	2382
0.3-0.4	6015
0.4-0.5	12344
0.5-0.6	8147
0.6-0.7	10349
0.7-0.8	1915
0.8-0.85	13
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC212207
0.8623	High Similarity	NPC475549
0.854	High Similarity	NPC310662
0.85	High Similarity	NPC475104
0.8462	Intermediate Similarity	NPC988
0.8462	Intermediate Similarity	NPC289432
0.8397	Intermediate Similarity	NPC144547
0.8209	Intermediate Similarity	NPC51079
0.8182	Intermediate Similarity	NPC77000
0.8182	Intermediate Similarity	NPC232958
0.8182	Intermediate Similarity	NPC238861
0.8095	Intermediate Similarity	NPC474630
0.8042	Intermediate Similarity	NPC156888
0.8042	Intermediate Similarity	NPC470722
0.8042	Intermediate Similarity	NPC470721
0.8042	Intermediate Similarity	NPC6100
0.803	Intermediate Similarity	NPC318173
0.8015	Intermediate Similarity	NPC295664
0.8	Intermediate Similarity	NPC136649
0.7986	Intermediate Similarity	NPC49272
0.7959	Intermediate Similarity	NPC476473
0.7958	Intermediate Similarity	NPC23894
0.7956	Intermediate Similarity	NPC236405
0.7945	Intermediate Similarity	NPC283292
0.7941	Intermediate Similarity	NPC318067
0.7939	Intermediate Similarity	NPC135730
0.7931	Intermediate Similarity	NPC213567
0.7905	Intermediate Similarity	NPC477409
0.7905	Intermediate Similarity	NPC29932
0.7891	Intermediate Similarity	NPC474300
0.7863	Intermediate Similarity	NPC228936
0.7863	Intermediate Similarity	NPC474408
0.7862	Intermediate Similarity	NPC476643
0.7857	Intermediate Similarity	NPC471832
0.7842	Intermediate Similarity	NPC51448
0.7842	Intermediate Similarity	NPC115797
0.7832	Intermediate Similarity	NPC474659
0.7823	Intermediate Similarity	NPC124365
0.7815	Intermediate Similarity	NPC306799
0.7815	Intermediate Similarity	NPC101043
0.7808	Intermediate Similarity	NPC1268
0.78	Intermediate Similarity	NPC300540
0.7793	Intermediate Similarity	NPC119542
0.7785	Intermediate Similarity	NPC471451
0.7778	Intermediate Similarity	NPC230848
0.7771	Intermediate Similarity	NPC284495
0.777	Intermediate Similarity	NPC5486
0.777	Intermediate Similarity	NPC201297
0.777	Intermediate Similarity	NPC253681
0.777	Intermediate Similarity	NPC81135
0.7756	Intermediate Similarity	NPC67197
0.7755	Intermediate Similarity	NPC32749
0.7755	Intermediate Similarity	NPC327916
0.7755	Intermediate Similarity	NPC42262
0.7755	Intermediate Similarity	NPC220496
0.7755	Intermediate Similarity	NPC183540
0.7755	Intermediate Similarity	NPC37992
0.7755	Intermediate Similarity	NPC241349
0.7755	Intermediate Similarity	NPC147542
0.7742	Intermediate Similarity	NPC3898
0.7737	Intermediate Similarity	NPC65627
0.7733	Intermediate Similarity	NPC474309
0.7733	Intermediate Similarity	NPC475923
0.7727	Intermediate Similarity	NPC474095
0.7718	Intermediate Similarity	NPC127857
0.7718	Intermediate Similarity	NPC469885
0.7718	Intermediate Similarity	NPC143898
0.7712	Intermediate Similarity	NPC11588
0.7712	Intermediate Similarity	NPC134685
0.7712	Intermediate Similarity	NPC229545
0.7712	Intermediate Similarity	NPC248265
0.771	Intermediate Similarity	NPC13784
0.7703	Intermediate Similarity	NPC257003
0.7702	Intermediate Similarity	NPC473094
0.7697	Intermediate Similarity	NPC471103
0.7697	Intermediate Similarity	NPC51602
0.7692	Intermediate Similarity	NPC477407
0.7692	Intermediate Similarity	NPC312560
0.7692	Intermediate Similarity	NPC476644
0.7692	Intermediate Similarity	NPC309430
0.7692	Intermediate Similarity	NPC477406
0.7692	Intermediate Similarity	NPC165612
0.7692	Intermediate Similarity	NPC58685
0.7687	Intermediate Similarity	NPC477408
0.7687	Intermediate Similarity	NPC471602
0.7687	Intermediate Similarity	NPC299405
0.7687	Intermediate Similarity	NPC306835
0.7687	Intermediate Similarity	NPC29771
0.7687	Intermediate Similarity	NPC323440
0.7687	Intermediate Similarity	NPC111422
0.7687	Intermediate Similarity	NPC476477
0.7687	Intermediate Similarity	NPC216312
0.7687	Intermediate Similarity	NPC470407
0.7687	Intermediate Similarity	NPC80605
0.7687	Intermediate Similarity	NPC256463
0.7687	Intermediate Similarity	NPC222968
0.7682	Intermediate Similarity	NPC136878
0.7682	Intermediate Similarity	NPC147250
0.7681	Intermediate Similarity	NPC328107
0.7681	Intermediate Similarity	NPC307139
0.7677	Intermediate Similarity	NPC84721
0.7676	Intermediate Similarity	NPC60825
0.7676	Intermediate Similarity	NPC253488
0.7676	Intermediate Similarity	NPC27659
0.7676	Intermediate Similarity	NPC291419
0.7671	Intermediate Similarity	NPC305060
0.7667	Intermediate Similarity	NPC89664
0.7667	Intermediate Similarity	NPC274085
0.7667	Intermediate Similarity	NPC475813
0.7662	Intermediate Similarity	NPC282239
0.7662	Intermediate Similarity	NPC114357
0.7662	Intermediate Similarity	NPC155329
0.7662	Intermediate Similarity	NPC259144
0.7658	Intermediate Similarity	NPC472781
0.7658	Intermediate Similarity	NPC472782
0.7654	Intermediate Similarity	NPC473095
0.7654	Intermediate Similarity	NPC473096
0.7647	Intermediate Similarity	NPC80370
0.7647	Intermediate Similarity	NPC329933
0.7643	Intermediate Similarity	NPC44199
0.7639	Intermediate Similarity	NPC254603
0.7639	Intermediate Similarity	NPC136994
0.7639	Intermediate Similarity	NPC59459
0.7639	Intermediate Similarity	NPC88255
0.7634	Intermediate Similarity	NPC292834
0.7632	Intermediate Similarity	NPC112216
0.7632	Intermediate Similarity	NPC165260
0.7632	Intermediate Similarity	NPC161239
0.7632	Intermediate Similarity	NPC478163
0.7632	Intermediate Similarity	NPC198455
0.7632	Intermediate Similarity	NPC119767
0.763	Intermediate Similarity	NPC254233
0.7628	Intermediate Similarity	NPC471456
0.7616	Intermediate Similarity	NPC478160
0.7613	Intermediate Similarity	NPC106895
0.761	Intermediate Similarity	NPC472261
0.761	Intermediate Similarity	NPC472783
0.761	Intermediate Similarity	NPC472780
0.7609	Intermediate Similarity	NPC223351
0.7606	Intermediate Similarity	NPC262819
0.7606	Intermediate Similarity	NPC131684
0.7606	Intermediate Similarity	NPC278928
0.7603	Intermediate Similarity	NPC232996
0.7603	Intermediate Similarity	NPC38158
0.7603	Intermediate Similarity	NPC141934
0.7603	Intermediate Similarity	NPC272268
0.76	Intermediate Similarity	NPC478164
0.76	Intermediate Similarity	NPC471100
0.76	Intermediate Similarity	NPC471107
0.7597	Intermediate Similarity	NPC77719
0.7597	Intermediate Similarity	NPC219419
0.7594	Intermediate Similarity	NPC470764
0.7594	Intermediate Similarity	NPC93181
0.7589	Intermediate Similarity	NPC478165
0.7589	Intermediate Similarity	NPC478162
0.7586	Intermediate Similarity	NPC1249
0.7584	Intermediate Similarity	NPC471444
0.7582	Intermediate Similarity	NPC94781
0.7582	Intermediate Similarity	NPC197037
0.7582	Intermediate Similarity	NPC470153
0.7582	Intermediate Similarity	NPC474107
0.7582	Intermediate Similarity	NPC470479
0.758	Intermediate Similarity	NPC478223
0.7578	Intermediate Similarity	NPC314653
0.7578	Intermediate Similarity	NPC316262
0.7574	Intermediate Similarity	NPC204784
0.7571	Intermediate Similarity	NPC100402
0.7571	Intermediate Similarity	NPC9180
0.7569	Intermediate Similarity	NPC70622
0.7569	Intermediate Similarity	NPC88864
0.7568	Intermediate Similarity	NPC295339
0.7568	Intermediate Similarity	NPC103337
0.7568	Intermediate Similarity	NPC114620
0.7566	Intermediate Similarity	NPC211565
0.7566	Intermediate Similarity	NPC60389
0.7566	Intermediate Similarity	NPC250046
0.7566	Intermediate Similarity	NPC470570
0.7566	Intermediate Similarity	NPC285122
0.7566	Intermediate Similarity	NPC60509
0.7566	Intermediate Similarity	NPC81698
0.7564	Intermediate Similarity	NPC290927
0.7564	Intermediate Similarity	NPC135522
0.7564	Intermediate Similarity	NPC472393
0.7564	Intermediate Similarity	NPC169990
0.7564	Intermediate Similarity	NPC477691
0.7564	Intermediate Similarity	NPC210942
0.7557	Intermediate Similarity	NPC474057
0.7556	Intermediate Similarity	NPC45794
0.7554	Intermediate Similarity	NPC77691
0.7554	Intermediate Similarity	NPC472704
0.7552	Intermediate Similarity	NPC470725
0.7552	Intermediate Similarity	NPC55949
0.7552	Intermediate Similarity	NPC198305
0.7551	Intermediate Similarity	NPC290601
0.7551	Intermediate Similarity	NPC245923
0.7551	Intermediate Similarity	NPC301341
0.755	Intermediate Similarity	NPC193703
0.755	Intermediate Similarity	NPC477913
0.755	Intermediate Similarity	NPC469385
0.755	Intermediate Similarity	NPC21599

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 NPC309056 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	841
0.2-0.3	1254
0.3-0.4	2576
0.4-0.5	2514
0.5-0.6	1257
0.6-0.7	415
0.7-0.8	33
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
0.8182	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3226	Approved
0.7483	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2346	Discontinued
0.7368	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7236	Approved
0.7241	Intermediate Similarity	NPD7008	Discontinued
0.7212	Intermediate Similarity	NPD7473	Discontinued
0.7206	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1470	Approved
0.7193	Intermediate Similarity	NPD8150	Discontinued
0.7193	Intermediate Similarity	NPD8434	Phase 2
0.7192	Intermediate Similarity	NPD3764	Approved
0.7161	Intermediate Similarity	NPD2532	Approved
0.7161	Intermediate Similarity	NPD2534	Approved
0.7161	Intermediate Similarity	NPD2533	Approved
0.7153	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5125	Phase 3
0.7143	Intermediate Similarity	NPD5126	Approved
0.7134	Intermediate Similarity	NPD6232	Discontinued
0.7134	Intermediate Similarity	NPD7239	Suspended
0.7133	Intermediate Similarity	NPD1283	Approved
0.7095	Intermediate Similarity	NPD2979	Phase 3
0.708	Intermediate Similarity	NPD5951	Approved
0.7073	Intermediate Similarity	NPD6959	Discontinued
0.7071	Intermediate Similarity	NPD1651	Approved
0.7051	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1201	Approved
0.7039	Intermediate Similarity	NPD1471	Phase 3
0.7039	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3300	Phase 2
0.7029	Intermediate Similarity	NPD3317	Approved
0.7029	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7819	Suspended
0.7015	Intermediate Similarity	NPD2182	Approved
0.7	Intermediate Similarity	NPD7741	Discontinued
0.6981	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5909	Discontinued
0.6964	Remote Similarity	NPD3751	Discontinued
0.6964	Remote Similarity	NPD7799	Discontinued
0.6963	Remote Similarity	NPD2067	Discontinued
0.6959	Remote Similarity	NPD2313	Discontinued
0.6957	Remote Similarity	NPD2629	Approved
0.6948	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1281	Approved
0.6914	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7961	Discontinued
0.6912	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2799	Discontinued
0.6906	Remote Similarity	NPD4198	Discontinued
0.6903	Remote Similarity	NPD4628	Phase 3
0.6903	Remote Similarity	NPD7003	Approved
0.6901	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2932	Approved
0.6879	Remote Similarity	NPD7390	Discontinued
0.6875	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4878	Approved
0.6875	Remote Similarity	NPD1608	Approved
0.6871	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2935	Discontinued
0.6863	Remote Similarity	NPD5404	Approved
0.6863	Remote Similarity	NPD5408	Approved
0.6863	Remote Similarity	NPD5405	Approved
0.6863	Remote Similarity	NPD5406	Approved
0.6863	Remote Similarity	NPD6099	Approved
0.6863	Remote Similarity	NPD6100	Approved
0.6854	Remote Similarity	NPD6534	Approved
0.6854	Remote Similarity	NPD6535	Approved
0.6853	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1237	Approved
0.6839	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4380	Phase 2
0.6824	Remote Similarity	NPD5844	Phase 1
0.6818	Remote Similarity	NPD2344	Approved
0.681	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5494	Approved
0.6803	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2798	Approved
0.6803	Remote Similarity	NPD6085	Phase 2
0.6802	Remote Similarity	NPD8368	Discontinued
0.6797	Remote Similarity	NPD7033	Discontinued
0.6797	Remote Similarity	NPD1510	Phase 2
0.6795	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7075	Discontinued
0.6783	Remote Similarity	NPD3019	Approved
0.6782	Remote Similarity	NPD8407	Phase 2
0.6781	Remote Similarity	NPD1876	Approved
0.6779	Remote Similarity	NPD4625	Phase 3
0.6776	Remote Similarity	NPD1607	Approved
0.6772	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD6778	Approved
0.6758	Remote Similarity	NPD6776	Approved
0.6758	Remote Similarity	NPD6781	Approved
0.6758	Remote Similarity	NPD6780	Approved
0.6758	Remote Similarity	NPD6782	Approved
0.6758	Remote Similarity	NPD6777	Approved
0.6758	Remote Similarity	NPD6779	Approved
0.6753	Remote Similarity	NPD2438	Suspended
0.6753	Remote Similarity	NPD2531	Phase 2
0.6752	Remote Similarity	NPD6190	Approved
0.674	Remote Similarity	NPD7700	Phase 2
0.674	Remote Similarity	NPD7699	Phase 2
0.6736	Remote Similarity	NPD4879	Approved
0.6733	Remote Similarity	NPD3268	Approved
0.6731	Remote Similarity	NPD2800	Approved
0.6728	Remote Similarity	NPD6599	Discontinued
0.6727	Remote Similarity	NPD7057	Phase 3
0.6727	Remote Similarity	NPD7058	Phase 2
0.6727	Remote Similarity	NPD3882	Suspended
0.6726	Remote Similarity	NPD3787	Discontinued
0.6724	Remote Similarity	NPD8313	Approved
0.6724	Remote Similarity	NPD8312	Approved
0.6723	Remote Similarity	NPD8360	Approved
0.6723	Remote Similarity	NPD8361	Approved
0.6716	Remote Similarity	NPD164	Approved
0.671	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.671	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5761	Phase 2
0.6707	Remote Similarity	NPD2801	Approved
0.6707	Remote Similarity	NPD5760	Phase 2
0.6691	Remote Similarity	NPD7635	Approved
0.6689	Remote Similarity	NPD2788	Approved
0.6688	Remote Similarity	NPD8166	Discontinued
0.6688	Remote Similarity	NPD3750	Approved
0.6688	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6273	Approved
0.6687	Remote Similarity	NPD3749	Approved
0.6687	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD5048	Discontinued
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD7177	Discontinued
0.6667	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2066	Phase 3
0.6649	Remote Similarity	NPD7697	Approved
0.6649	Remote Similarity	NPD7698	Approved
0.6649	Remote Similarity	NPD7696	Phase 3
0.6649	Remote Similarity	NPD7435	Discontinued
0.6646	Remote Similarity	NPD6801	Discontinued
0.6646	Remote Similarity	NPD37	Approved
0.6646	Remote Similarity	NPD1934	Approved
0.6646	Remote Similarity	NPD2309	Approved
0.6645	Remote Similarity	NPD2796	Approved
0.6645	Remote Similarity	NPD1240	Approved
0.6645	Remote Similarity	NPD4060	Phase 1
0.6644	Remote Similarity	NPD3972	Approved
0.6643	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1929	Approved
0.6642	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1930	Approved
0.6642	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD8435	Approved
0.6627	Remote Similarity	NPD5710	Approved
0.6627	Remote Similarity	NPD4966	Approved
0.6627	Remote Similarity	NPD4967	Phase 2
0.6627	Remote Similarity	NPD4965	Approved
0.6627	Remote Similarity	NPD7768	Phase 2
0.6627	Remote Similarity	NPD5711	Approved
0.6627	Remote Similarity	NPD7229	Phase 3
0.6622	Remote Similarity	NPD2797	Approved
0.662	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7871	Phase 2
0.6613	Remote Similarity	NPD7870	Phase 2
0.6609	Remote Similarity	NPD6559	Discontinued
0.6603	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6004	Phase 3
0.6603	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6002	Phase 3
0.6603	Remote Similarity	NPD6005	Phase 3
0.6601	Remote Similarity	NPD6355	Discontinued
0.6584	Remote Similarity	NPD1512	Approved
0.6579	Remote Similarity	NPD6663	Approved
0.6575	Remote Similarity	NPD6287	Discontinued
0.6567	Remote Similarity	NPD1932	Approved
0.6566	Remote Similarity	NPD3817	Phase 2
0.6565	Remote Similarity	NPD1989	Approved
0.6562	Remote Similarity	NPD6799	Approved
0.6554	Remote Similarity	NPD6696	Suspended
0.6552	Remote Similarity	NPD5306	Approved
0.6552	Remote Similarity	NPD5305	Approved
0.6552	Remote Similarity	NPD4626	Approved
0.655	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.655	Remote Similarity	NPD6166	Phase 2
0.655	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.655	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6234	Discontinued
0.6538	Remote Similarity	NPD1551	Phase 2
0.6533	Remote Similarity	NPD5736	Approved
0.6533	Remote Similarity	NPD2861	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data