NPASS Compound

Natural Product: NPC295643

Natural Product ID	NPC295643
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Methyl Glycyrrhetinate
IUPAC Name	methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1271483
PubChem CID	102135
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 83 87 0 0 0 0 0 0 0 0999 V2000 -6.9654 2.3509 -2.7351 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5420 1.6582 -1.5715 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2230 1.6312 -1.1448 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3821 2.2604 -1.8428 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8220 0.8826 0.0963 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5927 1.4920 1.2487 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3150 -0.5375 -0.0809 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5962 -1.4324 0.8882 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1088 -1.5318 0.5693 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7415 -0.3234 -0.2245 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3412 0.9494 0.3169 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2700 -0.2391 -0.3697 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7860 0.2073 -1.5454 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6486 0.3250 -1.7809 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0298 0.4274 -2.9630 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4830 0.3071 -0.5590 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0547 -0.9161 0.1792 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3449 -0.6272 0.7303 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8522 -1.7983 1.5142 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3035 -1.7128 1.8310 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3084 0.5669 1.6783 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8435 -2.1286 -0.7431 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9401 -1.3952 1.2669 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3508 -1.4502 0.6592 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6841 0.0099 0.4048 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9284 0.5955 -0.7422 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4352 0.2599 -2.1054 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1546 2.1167 -0.6110 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3047 2.5136 0.2000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5070 1.6435 0.2059 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1589 0.2054 0.4451 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9680 -0.7692 -0.3542 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5337 -0.0785 1.9213 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3285 1.8256 -0.9329 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9116 -2.7459 -0.3073 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7745 3.0594 -2.4118 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1392 2.9661 -3.1765 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4077 1.6571 -3.4707 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5946 1.0319 1.3748 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7917 2.5825 1.0644 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0249 1.4065 2.1930 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2573 -0.8839 -1.1212 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3875 -0.5482 0.2011 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0899 -2.4271 0.8537 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7634 -1.0388 1.9090 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2086 -0.4626 -1.2451 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9480 1.7795 -0.3140 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1459 1.1099 1.3786 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4965 0.4791 -2.3218 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0794 1.1718 0.0631 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2860 -1.7715 2.4950 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6342 -2.7784 1.0947 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6142 -2.6985 2.2614 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5529 -0.9609 2.6025 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9825 0.3871 2.5418 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6835 0.7702 2.0759 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6279 1.5122 1.1473 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5979 -2.2252 -1.5168 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9436 -3.0804 -0.1398 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1583 -2.1453 -1.1771 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6811 -2.4304 1.5172 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0137 -0.7724 2.1509 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2613 -1.9594 -0.3263 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0746 -1.9072 1.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2988 0.5792 1.3111 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5324 0.1775 -2.1671 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0511 -0.6702 -2.5509 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2192 1.1522 -2.7698 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1957 2.6058 -1.6068 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2277 2.5546 -0.1305 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9889 2.6956 1.2691 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6399 3.5348 -0.1486 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1663 2.0536 1.0347 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6286 -0.2677 -1.1229 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3602 -1.5930 -0.7985 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7329 -1.3313 0.2664 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7082 0.2177 2.5924 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4321 0.5269 2.1630 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8338 -1.1406 2.0351 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2802 1.6889 -0.7109 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5191 -2.4536 -1.3268 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2640 -3.5204 0.1520 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9095 -3.1753 -0.5258 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 1 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 18 21 1 1 17 22 1 6 17 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 26 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 30 34 1 0 9 35 1 6 11 5 1 0 18 12 1 0 31 25 1 0 20 9 1 0 26 16 1 0 1 36 1 0 1 37 1 0 1 38 1 0 6 39 1 0 6 40 1 0 6 41 1 0 7 42 1 0 7 43 1 0 8 44 1 0 8 45 1 0 10 46 1 6 11 47 1 0 11 48 1 0 13 49 1 0 16 50 1 1 19 51 1 0 19 52 1 0 20 53 1 0 20 54 1 0 21 55 1 0 21 56 1 0 21 57 1 0 22 58 1 0 22 59 1 0 22 60 1 0 23 61 1 0 23 62 1 0 24 63 1 0 24 64 1 0 25 65 1 1 27 66 1 0 27 67 1 0 27 68 1 0 28 69 1 0 28 70 1 0 29 71 1 0 29 72 1 0 30 73 1 1 32 74 1 0 32 75 1 0 32 76 1 0 33 77 1 0 33 78 1 0 33 79 1 0 34 80 1 0 35 81 1 0 35 82 1 0 35 83 1 0 M END

Standard InCHIKey	RMIVRCBSQPCSCQ-BDANYOJNSA-N
Standard InCHI	InChI=1S/C31H48O4/c1-26(2)22-9-12-31(7)24(29(22,5)11-10-23(26)33)21(32)17-19-20-18-28(4,25(34)35-8)14-13-27(20,3)15-16-30(19,31)6/h17,20,22-24,33H,9-16,18H2,1-8H3/t20-,22-,23-,24+,27+,28-,29-,30+,31+/m0/s1
SMILES	COC(=O)[C@@]1(C)CC[C@]2([C@@H](C1)C1=CC(=O)[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)C

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11164-015-2099-x]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1134/S1021443711030101]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO10026	Mitracarpus scaber	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7786	Lentinus tigrinus	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7786	Lentinus tigrinus	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10026	Mitracarpus scaber	Species	Rubiaceae	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	Organism Name	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
Ki	1
IC50	48
EC50	5
Ratio IC50	1

Activity Type	# Activity
Individual protein	3
Cell line	35
Organism	3
Non-molecular	13
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1218	Individual protein	Carbonic anhydrase II	Bos taurus	Ki	>	10000.0	nM	PMID[25147151]
NPT203	Individual protein	Carboxylesterase 2	Homo sapiens	IC50	=	5610.0	nM	PMID[26900660]
NPT166	Individual protein	Acyl coenzyme A:cholesterol acyltransferase	Homo sapiens	IC50	=	22360.0	nM	PMID[26900660]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1215	Cell line	8505C	Homo sapiens	IC50	=	26070.0	nM	PMID[24361520]
NPT179	Cell line	A2780	Homo sapiens	IC50	=	25540.0	nM	PMID[20884085]
NPT762	Cell line	A-431	Homo sapiens	IC50	=	25280.0	nM	PMID[20932766]
NPT81	Cell line	A549	Homo sapiens	IC50	=	23500.0	nM	PMID[20884085]
NPT579	Cell line	DLD-1	Homo sapiens	IC50	=	26120.0	nM	PMID[20884085]
NPT1216	Cell line	FaDu	Homo sapiens	IC50	=	23410.0	nM	PMID[20884085]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	22100.0	nM	PMID[20884085]
NPT180	Cell line	HCT-8	Homo sapiens	IC50	=	24360.0	nM	PMID[20884085]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	27540.0	nM	PMID[20884085]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	22140.0	nM	PMID[24361520]
NPT763	Cell line	SW-1736	Homo sapiens	IC50	=	34870.0	nM	PMID[20884085]
NPT660	Cell line	SW480	Homo sapiens	IC50	=	16080.0	nM	PMID[20884085]
NPT1886	Cell line	J774	Mus musculus	IC50	>	100000.0	nM	PMID[24268542]
NPT886	Cell line	NIH3T3	Mus musculus	IC50	=	22810.0	nM	PMID[24361520]
NPT1215	Cell line	8505C	Homo sapiens	EC50	>	30000.0	nM	PMID[26177446]
NPT81	Cell line	A549	Homo sapiens	EC50	>	30000.0	nM	PMID[26177446]
NPT139	Cell line	HT-29	Homo sapiens	EC50	>	30000.0	nM	PMID[26177446]
NPT83	Cell line	MCF7	Homo sapiens	EC50	>	30000.0	nM	PMID[26177446]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[26343825]
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[26343825]
NPT81	Cell line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[26343825]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	27540.0	nM	PMID[20932766]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	19420.0	nM	PMID[20884085]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	20470.0	nM	PMID[20932766]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[24268542]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	26120.0	nM	PMID[24361520]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	34870.0	nM	PMID[24361520]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	>	30000.0	nM	PMID[26177446]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	1744290.0	nM	PMID[22520261]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	443570.0	nM	PMID[22520261]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	4.0	n.a.	PMID[26900660]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC295643 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	17007
0.1-0.2	26649
0.2-0.3	5484
0.3-0.4	613
0.4-0.5	80
0.5-0.6	11
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.746	Intermediate Similarity	NPC214756
0.6923	Remote Similarity	NPC272075
0.6825	Remote Similarity	NPC602872
0.6618	Remote Similarity	NPC98874
0.6522	Remote Similarity	NPC4036
0.6522	Remote Similarity	NPC65120
0.6522	Remote Similarity	NPC145067
0.6522	Remote Similarity	NPC233455
0.6522	Remote Similarity	NPC158030
0.6111	Remote Similarity	NPC471966
0.6029	Remote Similarity	NPC479748
0.5588	Remote Similarity	NPC470588
0.5507	Remote Similarity	NPC480944
0.5455	Remote Similarity	NPC190035
0.5429	Remote Similarity	NPC246708
0.5405	Remote Similarity	NPC610635
0.5333	Remote Similarity	NPC476879
0.5303	Remote Similarity	NPC290598
0.5303	Remote Similarity	NPC30590
0.5067	Remote Similarity	NPC49776
0.5067	Remote Similarity	NPC63118
0.5067	Remote Similarity	NPC474436

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC295643 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6717
0.1-0.2	2307
0.2-0.3	118
0.3-0.4	2
0.4-0.5	5
0.5-0.6	0
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6522	Remote Similarity	NPD7515	Phase 2

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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