NPASS Compound

Natural Product: NPC174251

Natural Product ID	NPC174251
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Sid24841469
IUPAC Name	(3S,4S)-5-[(3S,4S)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-5-yl]-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromene-4,10-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL399293
PubChem CID	10257591
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001610] Arylnaphthalene lignans

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 76 81 0 0 0 0 0 0 0 0999 V2000 3.0373 -3.7890 3.4905 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0626 -3.1833 2.6625 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3409 -2.0234 1.9341 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6053 -1.4777 2.0447 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8969 -0.3244 1.3263 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1411 0.2504 1.4077 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1607 -0.2934 2.2093 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9226 0.2453 0.5242 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6573 -0.3134 0.4226 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3777 -1.4510 1.1344 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6918 0.2758 -0.3904 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0145 1.4153 -1.0863 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2698 1.9710 -0.9862 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2418 1.3797 -0.1695 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5118 1.9794 -0.0957 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6446 3.2036 -1.7182 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6146 3.6804 -2.4548 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3457 3.5378 -1.9613 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0413 2.0387 -1.9422 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1613 1.6062 -3.2530 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6146 4.1744 -2.9574 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6497 -0.2688 -0.5032 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0010 -1.2532 -1.3690 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0385 -1.8977 -2.2783 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2699 -1.3974 -3.5779 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5220 -3.3693 -2.3034 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5328 -4.2670 -2.8603 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6880 -3.3393 -3.0633 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7210 -2.7895 -2.3456 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2974 -1.7020 -1.4118 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2649 -1.1707 -0.5860 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9177 -0.1694 0.2982 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6208 0.2785 0.3401 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2937 1.2830 1.2361 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2282 1.8398 2.0792 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9003 2.8510 2.9814 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8382 3.4309 3.8486 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5197 1.3674 2.0111 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8964 0.3762 1.1439 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1930 -0.1242 1.0496 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2518 0.3410 1.8405 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5869 -1.6094 -0.6114 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9889 -3.9101 2.8936 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3205 -3.1336 4.3421 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7418 -4.7927 3.8108 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3745 -1.9213 2.6738 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1415 0.1728 1.9532 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9707 -0.1849 3.2821 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2472 -1.3856 1.9830 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3781 -1.8670 1.0359 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1854 1.6147 -0.7836 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0483 3.9783 -1.0014 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4885 2.9723 -2.4101 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1939 3.9264 -0.9407 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0501 1.9376 -1.5676 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0822 1.2691 -3.3872 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3774 3.6915 -3.9438 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6645 4.0037 -2.6731 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3544 5.2449 -3.0194 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0031 -1.8240 -1.9781 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2046 -1.1237 -3.6916 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8253 -3.6525 -1.2728 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8710 -4.9677 -2.0683 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1874 -4.8706 -3.7115 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4451 -3.7173 -3.1904 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4844 -2.3569 -3.0263 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1715 -3.5970 -1.7174 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2852 1.6232 1.2607 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1199 2.7173 4.6549 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7538 3.6822 3.2767 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4047 4.3692 4.2641 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2779 1.7943 2.6702 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0497 -0.4362 1.9678 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8839 0.5585 2.8830 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7083 1.2535 1.4185 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9288 -2.3805 -0.0468 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 4 5 1 0 5 6 1 0 6 7 1 0 5 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 13 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 18 21 1 0 11 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 35 38 1 0 38 39 2 0 39 40 1 0 40 41 1 0 31 42 1 0 10 3 1 0 19 12 1 0 33 22 1 0 14 8 1 0 30 23 1 0 39 32 1 0 1 43 1 0 1 44 1 0 1 45 1 0 4 46 1 0 7 47 1 0 7 48 1 0 7 49 1 0 10 50 1 0 15 51 1 0 16 52 1 0 16 53 1 0 18 54 1 1 19 55 1 1 20 56 1 0 21 57 1 0 21 58 1 0 21 59 1 0 24 60 1 1 25 61 1 0 26 62 1 1 27 63 1 0 27 64 1 0 27 65 1 0 29 66 1 0 29 67 1 0 34 68 1 0 37 69 1 0 37 70 1 0 37 71 1 0 38 72 1 0 41 73 1 0 41 74 1 0 41 75 1 0 42 76 1 0 M END

Standard InCHIKey	AVAQRWVGWWNBIN-CUAUGLLKSA-N
Standard InCHI	InChI=1S/C32H34O10/c1-13-29(33)27-19(11-41-13)31(35)23-17(7-15(37-3)9-21(23)39-5)25(27)26-18-8-16(38-4)10-22(40-6)24(18)32(36)20-12-42-14(2)30(34)28(20)26/h7-10,13-14,29-30,33-36H,11-12H2,1-6H3/t13-,14-,29+,30+/m0/s1
SMILES	COc1cc(OC)c2c(c1)c(c1c(c2O)CO[C@H]([C@H]1O)C)c1c2[C@H](O)[C@H](C)OCc2c(c2c1cc(OC)cc2OC)O

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
NPO32515	Cordyceps sp.	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17887724]
NPO32514	Cordyceps sp.	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17887724]
NPO32515	Cordyceps sp.	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]

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
Potency	38
EC50	3
IC50	9
Inhibition	1

Activity Type	# Activity
Individual protein	38
Cell line	1
Protein complex	2
Organism	3
Protein-protein interaction	4
Others	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1038	Individual protein	Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	50118.7	nM	PMID[19888756]
NPT3	Individual protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	3548.1	nM	PMID[18625769]
NPT1039	Individual protein	Envelope glycoprotein gp160	Human immunodeficiency virus 1	IC50	=	10100.0	nM	PMID[19035792]
NPT135	Individual protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[12762801]
NPT199	Individual protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[18500841]
NPT100	Individual protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	28183.8	nM	DrugMatrix in vitro pharmacology data
NPT11	Individual protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	3981.1	nM	PMID[22583079]
NPT1417	Individual protein	Transcriptional regulator ERG	Homo sapiens	Potency	n.a.	35481.3	nM	Open TG-GATES in vivo data: Biochemistry
NPT1040	Individual protein	Human immunodeficiency virus type 1 Tat protein	Human immunodeficiency virus type 1 group M subtype B (isolate HXB2)(HIV-1)	IC50	n.a.	30829.0	nM	DrugMatrix in vitro pharmacology data
NPT55	Individual protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	1990.5	nM	PMID[18646829]
NPT58	Individual protein	Bloom syndrome protein	Homo sapiens	Potency	=	31622.8	nM	PMID[8277313]
NPT797	Individual protein	Cytoplasmic zinc-finger protein	Caenorhabditis elegans	EC50	>	300000.0	nM	PMID[11311065]
NPT4214	Protein complex	SUMO-activating enzyme	Homo sapiens	IC50	=	17090.0	nM	PMID[22871217]
NPT4214	Protein complex	SUMO-activating enzyme	Homo sapiens	IC50	=	6030.0	nM	PMID[10869208]
NPT803	Individual protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[24900611]
NPT9	Individual protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[18177008]
NPT48	Individual protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	25118.9	nM	PMID[26034885]
NPT94	Individual protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	44668.4	nM	PMID[15730251]
NPT795	Individual protein	Zinc finger protein mex-5	Caenorhabditis elegans	EC50	>	300000.0	nM	PMID[11325244]
NPT3937	Protein-protein interaction	Voltage-gated N-type calcium channel alpha-1B subunit/Amyloid beta A4 precursor protein-binding family A member 1	Homo sapiens	IC50	=	4270.0	nM	PMID[9917313]
NPT57	Individual protein	Induced myeloid leukemia cell differentiation protein Mcl-1	Homo sapiens	IC50	=	2507.45	nM	PMID[25278237]
NPT3937	Protein-protein interaction	Voltage-gated N-type calcium channel alpha-1B subunit/Amyloid beta A4 precursor protein-binding family A member 1	Homo sapiens	IC50	=	20300.0	nM	DrugMatrix in vitro pharmacology data
NPT698	Individual protein	Regulator of G-protein signaling 4	Homo sapiens	Potency	n.a.	39810.7	nM	PubChem BioAssay data set
NPT444	Individual protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	44668.4	nM	PubChem BioAssay data set
NPT446	Individual protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[19654408]
NPT831	Individual protein	Serine/threonine-protein kinase PLK1	Homo sapiens	Potency	n.a.	21192.3	nM	PMID[18293924]
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	35481.3	nM	PMID[26331426]
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	316.2	nM	PMID[22437114]
NPT59	Individual protein	DNA polymerase beta	Homo sapiens	Potency	=	35481.3	nM	PMID[22194678]
NPT63	Individual protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[22652254]
NPT8	Individual protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[17665951]
NPT821	Individual protein	Werner syndrome ATP-dependent helicase	Homo sapiens	Potency	n.a.	50118.7	nM	Open TG-GATES in vivo data: Hematology
NPT755	Individual protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[22487595]
NPT920	Individual protein	Alpha-synuclein	Homo sapiens	Potency	n.a.	5623.4	nM	PMID[25028062]
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	31622.8	nM	PMID[17665951]
NPT47	Individual protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	25118.9	nM	DrugMatrix in vivo data: Hematology
NPT53	Individual protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	25118.9	nM	PMID[25310730]
NPT442	Individual protein	Ferritin light chain	Equus caballus	Potency	=	50118.7	nM	PMID[23336337]
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	17782.8	nM	PMID[15084123]
NPT864	Individual protein	Lethal(3)malignant brain tumor-like protein 1	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT532	Individual protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	50118.7	nM	DrugMatrix in vitro pharmacology data
NPT443	Individual protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[11405287]
NPT49	Individual protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[19640616]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell line	HepG2	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[19013823]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Inhibition	<	50.0	%	PMID[26711149]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	8100.0	nM	PMID[15189040]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PMID[18183025]
NPT2	Others	Unspecified	n.a.	EC50	>	110000.0	nM	PMID[18161942]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	10000.0	nM	PMID[15165138]
NPT2	Others	Unspecified	n.a.	IC50	n.a.	4610.0	nM	PMID[21441032]

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 NPC174251 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	18436
0.1-0.2	29494
0.2-0.3	1902
0.3-0.4	18
0.4-0.5	1
0.5-0.6	3
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC274454
0.7833	Intermediate Similarity	NPC153182
0.7705	Intermediate Similarity	NPC215678
0.5968	Remote Similarity	NPC118000
0.5357	Remote Similarity	NPC488351
0.5286	Remote Similarity	NPC205501

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC174251 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4528
0.1-0.2	4592
0.2-0.3	30
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
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
		NPD

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