NPASS Compound

Natural Product: NPC120075

Natural Product ID	NPC120075
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-(3,4-Dimethoxyphenyl)Ethanamine
IUPAC Name	2-(3,4-dimethoxyphenyl)ethanamine
Synonyms	2-(3,4-Dimethoxyphenyl)Ethanamine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL26019
PubChem CID	8421
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004113] Methoxybenzenes [CHEMONTID:0004111] Dimethoxybenzenes

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 28 28 0 0 0 0 0 0 0 0999 V2000 3.0336 0.5771 0.8840 N 0 0 0 0 0 0 0 0 0 0 0 0 3.2624 -0.5067 -0.0492 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3957 -0.3971 -1.2735 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9471 -0.4232 -0.9393 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2505 -1.6140 -0.8829 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0947 -1.6412 -0.5729 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8019 -0.4868 -0.3065 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1128 0.7073 -0.3609 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2322 0.7266 -0.6716 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8375 1.8571 -0.0909 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3015 3.1550 -0.1004 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1615 -0.5020 0.0080 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8615 -1.7131 0.0634 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4436 1.4596 0.4654 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5389 0.3704 1.7657 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0696 -1.4709 0.4671 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3132 -0.5200 -0.3794 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -1.2690 -1.9230 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6818 0.5026 -1.8586 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8184 -2.5225 -1.0952 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6355 -2.5798 -0.5303 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7694 1.6637 -0.7135 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4728 3.6508 -1.1005 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2300 3.1934 0.1918 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8218 3.8218 0.6480 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9516 -1.4946 0.1345 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6309 -2.2867 -0.8637 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4879 -2.2579 0.9719 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 7 12 1 0 12 13 1 0 9 4 1 0 1 14 1 0 1 15 1 0 2 16 1 0 2 17 1 0 3 18 1 0 3 19 1 0 5 20 1 0 6 21 1 0 9 22 1 0 11 23 1 0 11 24 1 0 11 25 1 0 13 26 1 0 13 27 1 0 13 28 1 0 M END

Standard InCHIKey	ANOUKFYBOAKOIR-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C10H15NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5-6,11H2,1-2H3
SMILES	NCCc1ccc(c(c1)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	181.11	Volume:	193.628 ? Van der Waals volume.
Dense:	0.935	LogP:	0.752 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.709 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-0.384 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	6.0
TPSA:	44.48 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	1.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.759	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	1.56	Fsp³:	0.4
MCE-18:	6.0 ? 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:	Rejected
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.107	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.032 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.252 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.364	Promiscuous compounds:	0.369

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.982	MDCK Permeability:	-5.026
Pgp-inhibitor:	0.054	Pgp-substrate:	0.984
PAMPA:	0.146 ? 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):	0.477
20% Bioavailability (F20%):	0.058	30% Bioavailability (F30%):	0.008
50% Bioavailability (F50%):	0.217

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.139	MRP1:	0.541
Plasma Protein Binding (PPB):	7.808%	Volume Distribution (VD):	0.026
Fu:	78.847% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.878
OATP1B3 inhibitor:	0.856	BCRP inhibitor:	0.059
BSEP inhibitor:	0.855

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	0.16	CYP3A4-substrate:	0.004
CYP2B6-substrate:	0.897	CYP2C8-inhibitor:	0.195
HLM stability:	0.0 ? 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):

6.082

Half-life (T1/2):

2.159

ADMET: Toxicity

hERG Blockers:	0.352	hERG Blockers (10um):	0.605
Human Hepatotoxicity (H-HT):	0.45	Drug-induced Liver Injury (DILI):	0.107
AMES Toxicity:	0.473	Rat Oral Acute Toxicity:	0.385
Maximum Recommended Daily Dose:	0.396	Skin Sensitization:	0.836
Carcinogencity:	0.361	Eye Corrosion:	0.984
Eye Irritation:	0.92	Respiratory Toxicity:	0.824
Drug-induced Neurotoxicity:	0.696	Ototoxicity:	0.32
Hematotoxicity:	0.23	Drug-induced Nephrotoxicity:	0.222
Genotoxicity:	0.066	RPMI-8226 Immunitoxicity:	0.071
A549 Cytotoxicity:	0.08	Hek293 Cytotoxicity:	0.15
BCF:	0.305 ? 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:	2.531 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.621 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.002 ? 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
NPO22998	Caloncoba echinata	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502310]
NPO25087	Hofmeisteria schaffneri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974630]
NPO22970	Monodora myristica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36400870]
NPO18600	Evasterias echinosoma	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25087	Hofmeisteria schaffneri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22256	Pegolettia senegalensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22195	Teucrium maghrebinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20971	Ritterella tokioka	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22516	Cyperus scaber	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20069	Solanum stenotomum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22896	Blakeslea trispora	Species	Choanephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17361	Delphinium iliense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17361	Delphinium iliense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23100	Leandra chaetodon	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20706	Euphorbia canescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18600	Evasterias echinosoma	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22068	Solanum polyadenium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25087	Hofmeisteria schaffneri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22256	Pegolettia senegalensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24277	Centaurea eriophora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23100	Leandra chaetodon	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20069	Solanum stenotomum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22461	Solidago multiradiata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17361	Delphinium iliense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22516	Cyperus scaber	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22195	Teucrium maghrebinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22998	Caloncoba echinata	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22896	Blakeslea trispora	Species	Choanephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20971	Ritterella tokioka	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO24919	Suttonia australis	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21379	Arthrophytum scoparium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4688	Lophozonia cunninghamii	Species	Nothofagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22970	Monodora myristica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26865	Vachellia caven	Species	Fabaceae	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
Kd	1
Activity	3
Potency	7
Inhibition	11
MAO deamination	2
MIC	1
IC50	2
Log activity	1
Human potency	1
Ratio	1

Activity Type	# Activity
Individual protein	10
Protein family	3
Organism	16
Single protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1530	Protein family	Serotonin (5-HT) receptor	Rattus norvegicus	Kd	=	4365.16	nM	PMID[7365744]
NPT4106	Individual protein	Amine oxidase, copper containing	Homo sapiens	Activity	=	0.0	%	PMID[17034126]
NPT4369	Individual protein	Amine oxidase, copper containing	Mus musculus	Activity	=	3.8	%	PMID[17034126]
NPT48	Individual protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT524	Individual protein	Serine-protein kinase ATM	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT20556	Single protein	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	1.946	%	DOI[10.6019/CHEMBL4495564]
NPT692	Individual protein	Histone deacetylase 6	Homo sapiens	Inhibition	=	-4.5	%	HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT692	Individual protein	Histone deacetylase 6	Homo sapiens	Inhibition	=	12.8	%	HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT442	Individual protein	Ferritin light chain	Equus caballus	Potency	=	11220.2	nM	PubChem BioAssay data set
NPT443	Individual protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	3162.3	nM	PubChem BioAssay data set
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	50118.7	nM	PubChem BioAssay data set
NPT49	Individual protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	8912.5	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT26852	Protein family	Monoamine oxidase	Bos taurus	MAO deamination	=	64.0	%	PMID[7310812]
NPT26852	Protein family	Monoamine oxidase	Bos taurus	MAO deamination	=	16.0	%	PMID[7310812]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	4147.5	nM	PubChem BioAssay data set
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	30.1	%	DOI[10.21203/rs.3.rs-23951/v1]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.15	%	DOI[10.6019/CHEMBL4495565]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	DOI[10.6019/CHEMBL4651402]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	DOI[10.6019/CHEMBL4651402]
NPT20	Organism	Candida albicans	Candida albicans	Inhibition	=	2.72	%	DOI[10.6019/CHEMBL4513141]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Inhibition	=	8.69	%	DOI[10.6019/CHEMBL4513141]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	256.0	ug.mL-1	PMID[23473681]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	-3.33	%	DOI[10.6019/CHEMBL4513141]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	4.73	%	DOI[10.6019/CHEMBL4513141]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	=	24.31	%	DOI[10.6019/CHEMBL4513141]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT605	Organism	Homo sapiens	Homo sapiens	Activity	<	0.2	MU	PMID[2299636]
NPT605	Organism	Homo sapiens	Homo sapiens	Log activity	=	-1.0	n.a.	PMID[2299636]
NPT605	Organism	Homo sapiens	Homo sapiens	Human potency	<	1.0	MU	PMID[7310812]
NPT605	Organism	Homo sapiens	Homo sapiens	Ratio	=	0.2	n.a.	PMID[592329]

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 NPC120075 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	27528
0.1-0.2	18339
0.2-0.3	3490
0.3-0.4	409
0.4-0.5	68
0.5-0.6	16
0.6-0.7	2
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
0.7273	Intermediate Similarity	NPC298486
0.7	Intermediate Similarity	NPC42383
0.6452	Remote Similarity	NPC105513
0.625	Remote Similarity	NPC292792
0.5882	Remote Similarity	NPC254625
0.5882	Remote Similarity	NPC165106
0.5556	Remote Similarity	NPC475961
0.5556	Remote Similarity	NPC13020
0.5556	Remote Similarity	NPC137685
0.5526	Remote Similarity	NPC251855
0.5405	Remote Similarity	NPC140359
0.5385	Remote Similarity	NPC470626
0.5385	Remote Similarity	NPC608982
0.5333	Remote Similarity	NPC488695
0.5263	Remote Similarity	NPC81067
0.5263	Remote Similarity	NPC477886
0.5263	Remote Similarity	NPC602945
0.5263	Remote Similarity	NPC609746
0.5143	Remote Similarity	NPC609310
0.5128	Remote Similarity	NPC205502

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC120075 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3973
0.1-0.2	4725
0.2-0.3	397
0.3-0.4	49
0.4-0.5	4
0.5-0.6	2
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
0.5882	Remote Similarity	NPD5283	Phase 2
0.5532	Remote Similarity	NPD3060	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