NPASS Compound

Natural Product: NPC318599

Natural Product ID	NPC318599
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MXFPFNSSZYNJGX-HNNGNKQASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	24892783
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues [CHEMONTID:0001506] Purine nucleotides [CHEMONTID:0001544] Purine ribonucleotides [CHEMONTID:0001618] Purine ribonucleoside diphosphates

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 56 58 0 0 0 0 0 0 0 0999 V2000 7.7540 0.1247 -0.3963 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2709 1.5525 -0.3443 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1106 1.8067 0.2226 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2804 0.7160 0.8055 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0074 0.6899 0.1257 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0408 -0.2775 0.5156 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8043 -0.3596 -0.0907 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8877 -1.3093 0.3101 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1933 -2.1712 1.3037 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3968 -2.0842 1.8869 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2966 -1.1573 1.4986 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2383 -1.2011 -0.4168 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0216 -0.1846 -1.2690 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2082 0.3220 -1.0726 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4281 -2.0240 -0.2888 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9962 -2.0228 1.0967 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4484 -2.3529 0.8438 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6400 -2.0229 -0.5935 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4445 -1.5299 -1.0922 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7091 -0.9815 -0.8414 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3918 0.2148 -0.2015 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5411 1.3998 -0.4421 P 0 0 0 0 0 0 0 0 0 0 0 0 -4.9629 2.4057 -1.4402 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9304 2.1929 1.0023 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9597 0.8054 -1.1268 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2647 1.6703 -0.4906 P 0 0 0 0 0 0 0 0 0 0 0 0 -9.5681 1.0230 -0.9666 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2750 1.5813 1.2093 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2372 3.2903 -0.9404 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6033 -3.7399 1.0327 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9012 -0.7802 1.7166 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0603 2.6638 -0.9091 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3175 2.7853 -0.3069 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8539 -0.3039 0.6157 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0142 -0.4747 -0.9607 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7261 0.1211 -0.9490 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7230 2.8289 0.2816 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7808 -0.2637 0.6500 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1601 0.9507 1.8826 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8003 1.3683 -0.6378 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6296 -2.7794 2.6808 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7622 0.1536 -2.0025 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1817 -3.0547 -0.5744 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5368 -2.8241 1.7276 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1279 -1.8032 1.5260 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9749 -2.9389 -1.1608 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7098 -1.3557 -0.5880 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6985 -0.7734 -1.9408 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3892 1.8899 1.7581 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0717 0.6653 1.5205 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8587 3.4471 -1.8255 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8392 -3.9348 1.9582 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3114 -0.1853 1.1949 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2571 2.4375 -1.9859 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4798 3.5946 -0.8946 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9698 2.1893 -0.7470 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 2 0 9 10 1 0 10 11 2 0 8 12 1 0 12 13 1 0 13 14 2 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 26 29 1 0 17 30 1 0 16 31 1 0 2 32 1 0 32 33 1 0 11 6 1 0 14 7 1 0 19 15 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 10 41 1 0 13 42 1 0 15 43 1 0 16 44 1 0 17 45 1 0 18 46 1 0 20 47 1 0 20 48 1 0 24 49 1 0 28 50 1 0 29 51 1 0 30 52 1 0 31 53 1 0 32 54 1 0 32 55 1 0 33 56 1 0 M END

Standard InCHIKey	MXFPFNSSZYNJGX-HNNGNKQASA-N
Standard InCHI	InChI=1S/C15H23N5O11P2/c1-8(4-21)2-3-16-13-10-14(18-6-17-13)20(7-19-10)15-12(23)11(22)9(30-15)5-29-33(27,28)31-32(24,25)26/h2,6-7,9,11-12,15,21-23H,3-5H2,1H3,(H,27,28)(H,16,17,18)(H2,24,25,26)/b8-2+/t9-,11-,12-,15-/m1/s1
SMILES	CC(=CCNC1=C2C(=NC=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)OP(=O)(O)O)O)O)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	511.09	Volume:	420.475 ? Van der Waals volume.
Dense:	1.216	LogP:	-1.486 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.2 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.455 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	18.0
TPSA:	238.84 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	7.0	Rings:	3.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.15	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.459	Fsp³:	0.533
MCE-18:	80.348 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.024	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.225 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.089	Promiscuous compounds:	0.002

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.835	MDCK Permeability:	-5.204
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	1.0 ? 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):	0.999
20% Bioavailability (F20%):	0.707	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.561
Plasma Protein Binding (PPB):	23.754%	Volume Distribution (VD):	-0.541
Fu:	68.63% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.114
OATP1B3 inhibitor:	0.981	BCRP inhibitor:	0.009
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.938	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
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):

2.172

Half-life (T1/2):

1.864

ADMET: Toxicity

hERG Blockers:	0.047	hERG Blockers (10um):	0.048
Human Hepatotoxicity (H-HT):	0.062	Drug-induced Liver Injury (DILI):	0.949
AMES Toxicity:	0.065	Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.985	Skin Sensitization:	0.999
Carcinogencity:	0.75	Eye Corrosion:	0.0
Eye Irritation:	0.287	Respiratory Toxicity:	0.989
Drug-induced Neurotoxicity:	0.139	Ototoxicity:	0.24
Hematotoxicity:	0.016	Drug-induced Nephrotoxicity:	0.973
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.107
A549 Cytotoxicity:	0.001	Hek293 Cytotoxicity:	0.113
BCF:	0.075 ? 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:	2.427 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.041 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.429 ? 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
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0014-5793(03)00033-4]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ac991142i]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1034/j.1399-3054.2003.00030.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1046/j.1365-3040.2001.00686.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.274.1.397]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M302362200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M314195200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M411109200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1104/pp.103.022368]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11005203]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12637544]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12805618]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14745019]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15280363]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15820655]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15834012]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[15844959]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1684022]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17611796]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18057039]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18235971]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18318836]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19521717]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21193570]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21194489]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21395888]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800258]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23370715]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23950498]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[24163311]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24285094]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[25457500]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[27363486]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27432888]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8278506]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	Database[MetaboLights]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	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

Molecular-level activity

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

In vitro activity

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

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 NPC318599 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	22765
0.1-0.2	26892
0.2-0.3	92
0.3-0.4	57
0.4-0.5	31
0.5-0.6	8
0.6-0.7	11
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
0.7089	Intermediate Similarity	NPC130586
0.6707	Remote Similarity	NPC174802
0.6627	Remote Similarity	NPC606410
0.6456	Remote Similarity	NPC239737
0.6282	Remote Similarity	NPC605318
0.622	Remote Similarity	NPC324033
0.6145	Remote Similarity	NPC324198
0.6145	Remote Similarity	NPC326529
0.6145	Remote Similarity	NPC319100
0.6049	Remote Similarity	NPC185991
0.6049	Remote Similarity	NPC321814
0.6	Remote Similarity	NPC321458
0.5977	Remote Similarity	NPC323091
0.5581	Remote Similarity	NPC195140
0.5444	Remote Similarity	NPC316618
0.5432	Remote Similarity	NPC136349
0.5432	Remote Similarity	NPC219313
0.5238	Remote Similarity	NPC261595
0.5057	Remote Similarity	NPC328479
0.5047	Remote Similarity	NPC90902

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC318599 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5480
0.1-0.2	3524
0.2-0.3	87
0.3-0.4	34
0.4-0.5	17
0.5-0.6	5
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	Drug ID	Developmental Stage
0.6707	Remote Similarity	NPD339	Phase 2
0.6049	Remote Similarity	NPD283	Phase 4
0.5432	Remote Similarity	NPD548	Clinical (unspecified phase)
0.5238	Remote Similarity	NPD247	Clinical (unspecified phase)
0.5172	Remote Similarity	NPD4171	Clinical (unspecified phase)
0.5056	Remote Similarity	NPD338	Approved
0.5047	Remote Similarity	NPD4716	Approved

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