NPASS Compound

Natural Product: NPC45849

Natural Product ID	NPC45849
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3'-O-Methyl-5'-Hydroxydiplacone
IUPAC Name	(2S)-2-(3,4-dihydroxy-5-methoxyphenyl)-6-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL463675
PubChem CID	24824762
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003646] 6-prenylated flavans [CHEMONTID:0003507] 6-prenylated flavanones

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 63 65 0 0 0 0 0 0 0 0999 V2000 -7.4135 0.2867 3.0450 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8569 -0.7001 2.1082 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7201 -0.4921 1.4284 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1760 -1.4809 0.4994 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0774 -1.1083 -0.9289 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2381 0.0569 -1.2660 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1714 -0.0945 -2.0515 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2456 0.9541 -2.4745 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8620 0.6232 -2.0019 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1068 -0.3394 -2.6319 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1651 -0.6556 -2.2121 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7150 0.0056 -1.1253 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9882 0.9734 -0.4720 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6065 1.6381 0.6612 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8999 2.4334 1.3393 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0224 1.4342 1.0658 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7938 0.7446 -0.0484 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0102 0.0590 0.4589 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9629 -1.1318 1.1490 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0902 -1.7703 1.6210 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3242 -1.2223 1.4105 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4017 -0.0270 0.7204 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2720 0.6072 0.2507 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6660 0.5148 0.5163 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7747 1.7469 -0.1928 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4996 -1.8303 1.8689 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9855 -2.9759 2.3149 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9828 -0.2675 -0.6592 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2939 1.2708 -0.9193 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9970 2.2521 -0.2364 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6369 -1.0120 -3.7194 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5649 1.3930 -0.7868 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5680 -1.9968 1.8859 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4714 0.0407 3.2532 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3822 1.3177 2.5926 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8335 0.3587 3.9921 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2292 0.4596 1.6354 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8651 -2.3815 0.5421 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1782 -1.8609 0.8374 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1101 -0.9094 -1.3647 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7452 -2.0290 -1.4846 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9775 -1.1041 -2.4099 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5187 1.9822 -2.2722 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1723 0.8793 -3.6014 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7722 -1.4079 -2.6941 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4797 2.4323 1.1865 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1076 0.8636 2.0052 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0574 1.4898 -0.8225 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9751 -1.5805 1.3235 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3267 1.5375 -0.2871 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1912 2.4830 0.3736 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2857 1.5762 -1.1859 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8386 1.9776 -0.2879 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3005 -1.7456 1.2505 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7545 -3.6002 2.4393 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5976 2.0932 0.5446 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0573 -1.0473 -4.5565 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9232 1.6493 0.0752 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3663 2.2002 -1.5313 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6271 1.4252 -0.4486 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4674 -2.0437 2.5654 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8574 -2.0780 0.8296 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9419 -2.8673 2.1988 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 21 26 1 0 20 27 1 0 17 28 1 0 13 29 2 0 29 30 1 0 10 31 1 0 6 32 1 0 2 33 1 0 29 9 1 0 28 12 1 0 23 18 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 4 38 1 0 4 39 1 0 5 40 1 0 5 41 1 0 7 42 1 0 8 43 1 0 8 44 1 0 11 45 1 0 16 46 1 0 16 47 1 0 17 48 1 6 19 49 1 0 23 50 1 0 25 51 1 0 25 52 1 0 25 53 1 0 26 54 1 0 27 55 1 0 30 56 1 0 31 57 1 0 32 58 1 0 32 59 1 0 32 60 1 0 33 61 1 0 33 62 1 0 33 63 1 0 M END

Standard InCHIKey	UKCODVXNYJFPIN-OMKLEDIQSA-N
Standard InCHI	InChI=1S/C26H30O7/c1-14(2)6-5-7-15(3)8-9-17-18(27)12-22-24(25(17)30)19(28)13-21(33-22)16-10-20(29)26(31)23(11-16)32-4/h6,8,10-12,21,27,29-31H,5,7,9,13H2,1-4H3/b15-8+/t21-/m0/s1
SMILES	CC(=CCC/C(=C/Cc1c(cc2c(C(=O)C[C@@H](c3cc(c(c(c3)OC)O)O)O2)c1O)O)/C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	454.2	Volume:	470.386 ? Van der Waals volume.
Dense:	0.966	LogP:	5.738 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.783 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.345 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	20.0
TPSA:	116.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.324	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.57	Fsp³:	0.346
MCE-18:	68.514 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.898	Fluc inhibitor:	0.639 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.455 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.782 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.353	Promiscuous compounds:	0.162

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.049	MDCK Permeability:	-4.764
Pgp-inhibitor:	0.993	Pgp-substrate:	0.0
PAMPA:	0.008 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.184	30% Bioavailability (F30%):	0.88
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.909
Plasma Protein Binding (PPB):	96.873%	Volume Distribution (VD):	-0.016
Fu:	2.785% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.907
BSEP inhibitor:	0.972

ADMET: Metabolism

CYP1A2-inhibitor:	0.009	CYP1A2-substrate:	0.919
CYP2C19-inhibitor:	0.252	CYP2C19-substrate:	0.87
CYP2C9-inhibitor:	0.066	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.005	CYP2D6-substrate:	0.595
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.997 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

6.515

Half-life (T1/2):

1.484

ADMET: Toxicity

hERG Blockers:	0.071	hERG Blockers (10um):	0.572
Human Hepatotoxicity (H-HT):	0.863	Drug-induced Liver Injury (DILI):	0.93
AMES Toxicity:	0.399	Rat Oral Acute Toxicity:	0.744
Maximum Recommended Daily Dose:	0.694	Skin Sensitization:	0.993
Carcinogencity:	0.332	Eye Corrosion:	0.0
Eye Irritation:	0.876	Respiratory Toxicity:	0.983
Drug-induced Neurotoxicity:	0.336	Ototoxicity:	0.689
Hematotoxicity:	0.259	Drug-induced Nephrotoxicity:	0.757
Genotoxicity:	0.981	RPMI-8226 Immunitoxicity:	0.235
A549 Cytotoxicity:	0.956	Hek293 Cytotoxicity:	0.577
BCF:	2.097 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	5.066 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.679 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.09 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[17625893]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[18293924]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192247]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21319773]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[22445674]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23623680]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25735399]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28322565]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28968119]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	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
IC50	3
Ratio IC50	1
MIC	10
EC50	7

Activity Type	# Activity
Individual protein	4
Cell line	7
Organism	10

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual protein	Cyclooxygenase-1	Ovis aries	IC50	=	3300.0	nM	PMID[28322565]
NPT31	Individual protein	Cyclooxygenase-2	Homo sapiens	IC50	=	10600.0	nM	PMID[28322565]
NPT570	Individual protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	60.0	nM	PMID[28322565]
NPT570	Individual protein	Arachidonate 5-lipoxygenase	Homo sapiens	Ratio IC50	=	10.0	n.a.	PMID[28322565]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell line	MCF7	Homo sapiens	EC50	<	10000.0	nM	PMID[17049255]
NPT404	Cell line	CCRF-CEM	Homo sapiens	EC50	<	10000.0	nM	PMID[17049255]
NPT389	Cell line	RPMI-8226	Homo sapiens	EC50	=	7300.0	nM	PMID[17049255]
NPT2015	Cell line	U-266	Homo sapiens	EC50	=	5500.0	nM	PMID[17908946]
NPT165	Cell line	HeLa	Homo sapiens	EC50	=	7400.0	nM	PMID[17908946]
NPT1160	Cell line	BJ	Homo sapiens	EC50	=	4700.0	nM	PMID[19275174]
NPT1970	Cell line	THP-1	Homo sapiens	EC50	<	10000.0	nM	PMID[17908946]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	32.0	ug.mL-1	PMID[8258833]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	4.0	ug.mL-1	PMID[20153644]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	MIC	=	4.0	ug.mL-1	PMID[19651906]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	32.0	ug.mL-1	PMID[20594858]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	32.0	ug.mL-1	DrugMatrix in vitro pharmacology data
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	4.0	ug.mL-1	PMID[19651906]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2.0	ug.mL-1	PMID[19651906]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	4.0	ug.mL-1	PMID[19651906]
NPT3608	Organism	Salmonella enteritidis	Salmonella enterica subsp. enterica serovar Enteritidis	MIC	>	32.0	ug.mL-1	PMID[8105084]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	4.0	ug.mL-1	PMID[8145236]

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 NPC45849 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	20330
0.1-0.2	25391
0.2-0.3	3532
0.3-0.4	482
0.4-0.5	68
0.5-0.6	26
0.6-0.7	14
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8261	Intermediate Similarity	NPC470328
0.8261	Intermediate Similarity	NPC209614
0.8082	Intermediate Similarity	NPC488555
0.8082	Intermediate Similarity	NPC484418
0.7857	Intermediate Similarity	NPC213896
0.7808	Intermediate Similarity	NPC472626
0.7808	Intermediate Similarity	NPC195796
0.7778	Intermediate Similarity	NPC278778
0.7746	Intermediate Similarity	NPC164272
0.7746	Intermediate Similarity	NPC470327
0.7606	Intermediate Similarity	NPC64915
0.7534	Intermediate Similarity	NPC226025
0.7534	Intermediate Similarity	NPC298692
0.7465	Intermediate Similarity	NPC290133
0.7222	Intermediate Similarity	NPC228504
0.6933	Remote Similarity	NPC185276
0.6623	Remote Similarity	NPC488558
0.6538	Remote Similarity	NPC472630
0.6486	Remote Similarity	NPC35038
0.6456	Remote Similarity	NPC210459
0.6456	Remote Similarity	NPC472631
0.6375	Remote Similarity	NPC472598
0.6282	Remote Similarity	NPC261063
0.625	Remote Similarity	NPC488557
0.622	Remote Similarity	NPC474055
0.6203	Remote Similarity	NPC321779
0.6145	Remote Similarity	NPC472634
0.6125	Remote Similarity	NPC488554
0.6071	Remote Similarity	NPC321399
0.5976	Remote Similarity	NPC27337
0.5972	Remote Similarity	NPC1089
0.5921	Remote Similarity	NPC223787
0.5904	Remote Similarity	NPC287328
0.5875	Remote Similarity	NPC22192
0.5854	Remote Similarity	NPC282009
0.5823	Remote Similarity	NPC472629
0.5802	Remote Similarity	NPC470326
0.575	Remote Similarity	NPC488556
0.5733	Remote Similarity	NPC125855
0.5732	Remote Similarity	NPC472628
0.5679	Remote Similarity	NPC472627
0.5679	Remote Similarity	NPC58805
0.5625	Remote Similarity	NPC279650
0.5595	Remote Similarity	NPC484417
0.5422	Remote Similarity	NPC201800
0.5366	Remote Similarity	NPC262039
0.5325	Remote Similarity	NPC223500
0.5325	Remote Similarity	NPC166689
0.525	Remote Similarity	NPC477242
0.5122	Remote Similarity	NPC484416
0.5122	Remote Similarity	NPC96408
0.5122	Remote Similarity	NPC610511
0.5119	Remote Similarity	NPC299436
0.5062	Remote Similarity	NPC24136
0.5059	Remote Similarity	NPC67396

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC45849 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4638
0.1-0.2	4462
0.2-0.3	43
0.3-0.4	6
0.4-0.5	1
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