NPASS Compound

Natural Product: NPC203424

Natural Product ID	NPC203424
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Tamsulosin Hydrochloride
IUPAC Name	5-[(2R)-2-[2-(2-ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide;hydron;chloride
Synonyms	Alphacard MR; Bazetham MR; Contiflo XL; Cositam XL; Diffundox; Faramsil; Flectone XL; Flomax; Flomax MR; Flomax Relief MR; Flomaxtra XL; Galebon; Losinate MR; LY-253351; Maxtron; Morvesin XL; Omnic MR; Pamsvax XL; Petyme; Pinexel PR; Prosurin XL; R-(-)-YM-12617; Stronazon; Tabphyn MR; Tamfrex XL; Tamsulosin HCl; Tamurex; YM-12617-1; YM-617
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1200914
PubChem CID	25137847 5362376
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000186] Phenethylamines [CHEMONTID:0000188] Amphetamines and derivatives

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 58 58 0 0 0 0 0 0 0 0999 V2000 7.8057 0.7385 0.9389 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2561 0.8151 -0.4469 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8681 0.7244 -0.5339 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0844 -0.3187 -0.1209 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6049 -1.4368 0.4457 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8422 -2.5008 0.8702 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4846 -2.3902 0.6955 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9297 -1.2601 0.1208 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6898 -0.1956 -0.3055 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1985 0.9484 -0.8876 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8730 1.2026 -1.1897 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3587 0.2823 -2.2435 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0285 0.5213 -2.5773 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9625 0.1967 -1.5461 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3469 0.5688 -2.0492 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4215 0.2815 -1.0747 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -0.8950 -1.0805 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1376 -1.1394 -0.1355 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4436 -0.2170 0.8309 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7287 0.9673 0.8418 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7452 1.1954 -0.0947 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1320 2.1388 2.0854 S 0 0 0 0 0 0 0 0 0 0 0 0 -6.5669 2.5395 2.0311 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8580 1.5722 3.4515 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0954 3.5034 1.8709 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.4445 -0.4407 1.7902 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1326 -1.6742 1.7160 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8611 -1.1725 -0.9777 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6892 0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 7.0523 0.5987 1.7253 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5373 -0.1039 1.0404 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3768 1.6593 1.1962 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5617 1.7852 -0.9374 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7316 0.0199 -1.0712 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6906 -1.5695 0.6067 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3033 -3.3800 1.3200 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8519 -3.2018 1.0149 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8474 -1.1768 0.0169 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6904 2.2579 -1.5003 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2863 1.1026 -0.2324 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9234 0.6012 -3.1964 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5395 -0.7677 -2.1531 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2328 -0.0837 -3.4230 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7389 0.9165 -0.6990 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 1.6451 -2.3152 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5326 0.0285 -3.0218 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9677 -1.6693 -1.8079 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6925 -2.0817 -0.1593 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1891 2.1456 -0.0666 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1241 3.2267 1.6927 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2439 4.2187 2.5917 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4026 -2.5085 1.7424 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6077 -1.6988 0.7078 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8971 -1.7663 2.5116 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0487 -1.8005 -1.4532 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7562 -1.7911 -1.0132 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5460 -1.1617 0.1110 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6892 0.0000 0.0000 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 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 2 0 22 24 2 0 22 25 1 0 19 26 1 0 26 27 1 0 14 28 1 0 9 4 1 0 21 16 1 0 1 30 1 0 1 31 1 0 1 32 1 0 2 33 1 0 2 34 1 0 5 35 1 0 6 36 1 0 7 37 1 0 8 38 1 0 11 39 1 0 11 40 1 0 12 41 1 0 12 42 1 0 13 43 1 0 14 44 1 1 15 45 1 0 15 46 1 0 17 47 1 0 18 48 1 0 21 49 1 0 25 50 1 0 25 51 1 0 27 52 1 0 27 53 1 0 27 54 1 0 28 55 1 0 28 56 1 0 28 57 1 0 29 58 1 0 M END

Standard InCHIKey	ZZIZZTHXZRDOFM-XFULWGLBSA-N
Standard InCHI	InChI=1S/C20H28N2O5S.ClH/c1-4-26-17-7-5-6-8-18(17)27-12-11-22-15(2)13-16-9-10-19(25-3)20(14-16)28(21,23)24;/h5-10,14-15,22H,4,11-13H2,1-3H3,(H2,21,23,24);1H/t15-;/m1./s1
SMILES	CCOc1ccccc1OCCN[C@@H](Cc1ccc(c(c1)S(=O)(=O)N)OC)C.Cl

Calculated Properties

Physi-Chem Properties

Molecular Weight:	408.17	Volume:	405.998 ? Van der Waals volume.
Dense:	1.005	LogP:	1.791 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.545 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.455 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	14.0
TPSA:	99.88 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	3.0	Rings:	2.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.554	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.594	Fsp³:	0.4
MCE-18:	30.0 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.057	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.015 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.454 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.889

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.7	MDCK Permeability:	-5.117
Pgp-inhibitor:	0.031	Pgp-substrate:	0.823
PAMPA:	0.066 ? 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):	0.0
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.672
Plasma Protein Binding (PPB):	97.094%	Volume Distribution (VD):	-0.808
Fu:	2.084% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.001
OATP1B3 inhibitor:	0.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.584

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.013 ? 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):

0.004

Half-life (T1/2):

2.538

ADMET: Toxicity

hERG Blockers:	0.824	hERG Blockers (10um):	0.342
Human Hepatotoxicity (H-HT):	0.975	Drug-induced Liver Injury (DILI):	0.975
AMES Toxicity:	0.229	Rat Oral Acute Toxicity:	0.834
Maximum Recommended Daily Dose:	0.997	Skin Sensitization:	0.004
Carcinogencity:	0.043	Eye Corrosion:	0.0
Eye Irritation:	0.009	Respiratory Toxicity:	0.818
Drug-induced Neurotoxicity:	0.747	Ototoxicity:	0.316
Hematotoxicity:	0.027	Drug-induced Nephrotoxicity:	0.032
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.044
A549 Cytotoxicity:	0.009	Hek293 Cytotoxicity:	0.441
BCF:	0.326 ? 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:	2.949 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.407 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.631 ? 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
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	roots	n.a.	n.a.	PMID[22381047]
NPO4659	Asiasarum heterotropoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29078	Asiasarum sieboldii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29078	Asiasarum sieboldii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4659	Asiasarum heterotropoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4659	Asiasarum heterotropoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29078	Asiasarum sieboldii	n.a.	n.a.	n.a.	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
Potency	7
Inhibition	4
AC50	6
Inhibition index	1

Activity Type	# Activity
Individual protein	2
Organism	4
Single protein	1
Others	11

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	23914.5	nM	PubChem BioAssay data set
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	10590.9	nM	PubChem BioAssay data set
NPT20556	Single protein	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	12.91	%	DOI[10.6019/CHEMBL4495564]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition index	=	0.7987	n.a.	DOI[10.1101/2020.04.03.023846]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.74	%	DOI[10.21203/rs.3.rs-23951/v1]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.06	%	DOI[10.6019/CHEMBL4495565]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	2984.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	24791	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	11985.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	29849.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	15089	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	n.a.	28190.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	n.a.	5623.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	n.a.	25118.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	n.a.	1995.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	n.a.	39810.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	n.a.	44668.4	nM	PubChem BioAssay data set

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
-	Rattus norvegicus	LD50	=	650.0	mg/kg	ToxVal
-	Mus musculus	LD50	=	1023.0	mg/kg	ToxVal

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 NPC203424 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	27454
0.1-0.2	21608
0.2-0.3	783
0.3-0.4	12
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	1

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC206372

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC203424 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2810
0.1-0.2	5838
0.2-0.3	465
0.3-0.4	32
0.4-0.5	3
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	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4179	Approved
0.98	High Similarity	NPD4180	Phase 4

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