Natural Product: NPC269827

Natural Product IDNPC269827
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 (2R,3R,4S,5R)-2-(6-Amino-2-Chloropurin-9-Yl)-5-(Hydroxymethyl)Oxolane-3,4-Diol
IUPAC Name (2R,3R,4S,5R)-2-(6-amino-2-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Synonyms 2-Chloroadenosine
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL285819
PubChem CID 8974
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues
      • [CHEMONTID:0000479] Purine nucleosides

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

  Chemical Representations

Standard InCHIKey BIXYYZIIJIXVFW-UUOKFMHZSA-N
Standard InCHI InChI=1S/C10H12ClN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6-,9-/m1/s1
SMILES OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(Cl)nc2N

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   301.06 Volume:   250.657
?
Van der Waals volume.
Dense:   1.201 LogP:   -0.538
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   -0.07
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -1.708
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   2.0 Rigid Bonds:   15.0
TPSA:   139.54
?
Topological Polar Surface Area.
 H-Bond Acceptor:   9.0
H-Bond Donor:   5.0 Rings:   3.0
Heavy Atoms:   10.0

MedChem Properties

QED Drug-Likeness Score:   0.5 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.67 Fsp3:   0.5
MCE-18:   63.6
?
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:   Rejected BMS Rule:   0
Chelating Alert:   1 PAINS Alert:   0
Colloidal aggregators:   0.126 Fluc inhibitor:   0.001
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.328
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.011
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.056 Promiscuous compounds:   0.138

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.781 MDCK Permeability:   -4.959
Pgp-inhibitor:   0.0 Pgp-substrate:   0.403
PAMPA:   0.846
?
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):   0.098
20% Bioavailability (F20%):   0.013 30% Bioavailability (F30%):   0.423
50% Bioavailability (F50%):   0.154

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.808 MRP1:   0.158
Plasma Protein Binding (PPB):   40.086% Volume Distribution (VD):   0.491
Fu: 55.911%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.997
OATP1B3 inhibitor:   0.998 BCRP inhibitor:   0.006
BSEP inhibitor:   0.0

ADMET: Metabolism

CYP1A2-inhibitor:   0.002 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.0 CYP2C19-substrate:   0.001
CYP2C9-inhibitor:   0.0 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.008
CYP3A4-inhibitor:   0.232 CYP3A4-substrate:   0.478
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.126
HLM stability:   0.102
?
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):  10.975 Half-life (T1/2):  2.14

ADMET: Toxicity

hERG Blockers:  0.035 hERG Blockers (10um):  0.2
Human Hepatotoxicity (H-HT):  0.899 Drug-induced Liver Injury (DILI):  0.971
AMES Toxicity:  0.88 Rat Oral Acute Toxicity:  0.162
Maximum Recommended Daily Dose:  0.292 Skin Sensitization:  0.95
Carcinogencity:  0.624 Eye Corrosion:  0.0
Eye Irritation:  0.443 Respiratory Toxicity:  0.356
Drug-induced Neurotoxicity:  0.859 Ototoxicity:  0.908
Hematotoxicity:  0.758 Drug-induced Nephrotoxicity:  0.868
Genotoxicity:  0.983 RPMI-8226 Immunitoxicity:  0.147
A549 Cytotoxicity:  0.128 Hek293 Cytotoxicity:  0.322
BCF:   0.004
?
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:   2.538
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.128
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.212
?
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
NPO27451 Ophiocordyceps sinensis Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27451 Ophiocordyceps sinensis Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27451 Ophiocordyceps sinensis Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO27451 Ophiocordyceps sinensis Species Ophiocordycipitaceae 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
NPT1315 Individual protein Adenosine A1 receptor Rattus norvegicus Ki = 9.3 nM PMID[7707320]
NPT1315 Individual protein Adenosine A1 receptor Rattus norvegicus Ki = 6.7 nM PMID[1766003]
NPT1316 Individual protein Adenosine A2a receptor Rattus norvegicus Ki = 76.0 nM PMID[1766003]
NPT216 Individual protein Adenosine A1 receptor Homo sapiens Affinity constant = 0.01 uM PMID[6279840]
NPT1315 Individual protein Adenosine A1 receptor Rattus norvegicus EC25 = 170.0 nM PMID[3336027]
NPT1316 Individual protein Adenosine A2a receptor Rattus norvegicus Ki = 63.0 nM PMID[7707320]
NPT1760 Individual protein Adenosine A3 receptor Rattus norvegicus Ki = 1890.0 nM PMID[7707320]
NPT217 Individual protein Adenosine A2a receptor Homo sapiens Ki = 120.0 nM PMID[9572897]
NPT1760 Individual protein Adenosine A3 receptor Rattus norvegicus Ki = 3200.0 nM PMID[9572897]
NPT218 Individual protein Adenosine A3 receptor Homo sapiens EC50 = 1630.0 nM PMID[12238926]
NPT218 Individual protein Adenosine A3 receptor Homo sapiens Efficacy = 100.0 % PMID[12238926]
NPT218 Individual protein Adenosine A3 receptor Homo sapiens Ki = 87.0 nM PMID[12238926]
NPT218 Individual protein Adenosine A3 receptor Homo sapiens Ki = 650.0 nM PMID[11708915]
NPT218 Individual protein Adenosine A3 receptor Homo sapiens Ki = 11600.0 nM PMID[11708915]
NPT1315 Individual protein Adenosine A1 receptor Rattus norvegicus IC50 = 37.0 nM PMID[1875349]
NPT2811 Individual protein Adenosine A1 receptor Cavia porcellus EC50 = 190.55 nM PMID[2016707]
NPT1315 Individual protein Adenosine A1 receptor Rattus norvegicus Ki = 8.74 nM PMID[2995663]
NPT216 Individual protein Adenosine A1 receptor Homo sapiens Ki = 18.4 nM PMID[8496700]
NPT216 Individual protein Adenosine A1 receptor Homo sapiens Activity = 90.0 % PMID[8496700]
NPT211 Individual protein Hypoxia-inducible factor 1 alpha Homo sapiens Potency = 6309.6 nM PubChem BioAssay data set
NPT282 Individual protein MAP kinase ERK2 Homo sapiens Potency = 10000.0 nM PubChem BioAssay data set
NPT282 Individual protein MAP kinase ERK2 Homo sapiens Potency = 14125.4 nM PubChem BioAssay data set
NPT2944 Individual protein Relaxin receptor 1 Homo sapiens Potency = 3981.1 nM PubChem BioAssay data set
NPT1754 Individual protein Adenosine deaminase Bos taurus Ki = 54500.0 nM PMID[21138280]
NPT152 Individual protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 20596.2 nM PubChem BioAssay data set
NPT2944 Individual protein Relaxin receptor 1 Homo sapiens Potency n.a. 2181.0 nM PubChem BioAssay data set
NPT154 Individual protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 22387.2 nM PubChem BioAssay data set
NPT2944 Individual protein Relaxin receptor 1 Homo sapiens Potency n.a. 21810.3 nM PubChem BioAssay data set
NPT10 Individual protein Geminin Homo sapiens Potency n.a. 29092.9 nM PubChem BioAssay data set
NPT101 Individual protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 7079.5 nM PubChem BioAssay data set
NPT217 Individual protein Adenosine A2a receptor Homo sapiens Ki = 180.0 nM PMID[24164628]
NPT216 Individual protein Adenosine A1 receptor Homo sapiens Ki = 1.39 nM PMID[24164628]
NPT218 Individual protein Adenosine A3 receptor Homo sapiens Ki = 19.0 nM PMID[24164628]
NPT2776 Individual protein Serotonin 1e (5-HT1e) receptor Homo sapiens Inhibition < 50.0 % PMID[27933810]
NPT294 Individual protein Serotonin 6 (5-HT6) receptor Homo sapiens Inhibition < 50.0 % PMID[27933810]
NPT1785 Individual protein Serotonin 7 (5-HT7) receptor Homo sapiens Inhibition < 50.0 % PMID[27933810]
NPT290 Individual protein Serotonin 2a (5-HT2a) receptor Homo sapiens Ki > 10000.0 nM PMID[27933810]
NPT290 Individual protein Serotonin 2a (5-HT2a) receptor Homo sapiens Inhibition = 46.0 % PMID[27933810]
NPT291 Individual protein Serotonin 2b (5-HT2b) receptor Homo sapiens Inhibition < 10.0 % PMID[27933810]
NPT292 Individual protein Serotonin 2c (5-HT2c) receptor Homo sapiens Inhibition < 10.0 % PMID[27933810]
NPT216 Individual protein Adenosine A1 receptor Homo sapiens Ki = 2.8 nM PMID[27933810]
NPT1784 Individual protein Serotonin 5a (5-HT5a) receptor Homo sapiens Inhibition < 50.0 % PMID[27933810]
NPT2812 Protein family Adenosine A2 receptor Homo sapiens Affinity constant = 5.0 uM PMID[6279840]
NPT2812 Protein family Adenosine A2 receptor Homo sapiens EC50 = 25.12 nM PMID[2016707]
NPT483 Individual protein Prelamin-A/C Homo sapiens Potency = 10000.0 nM PubChem BioAssay data set
NPT483 Individual protein Prelamin-A/C Homo sapiens Potency = 35481.3 nM PubChem BioAssay data set
NPT4624 Individual protein Relaxin receptor 2 Homo sapiens Potency n.a. 17324.5 nM PubChem BioAssay data set
NPT803 Individual protein Flap endonuclease 1 Homo sapiens Potency n.a. 8436.8 nM PubChem BioAssay data set
NPT4504 Individual protein Endoplasmin Homo sapiens Kd = 8600.0 nM PMID[33738064]
NPT4504 Individual protein Endoplasmin Homo sapiens Ki = 1800.0 nM PMID[33738064]
NPT5049 Individual protein Adenosine A1 receptor Bos taurus Ki = 25.0 nM PMID[6279840]
NPT5049 Individual protein Adenosine A1 receptor Bos taurus Ki = 20.2 nM PMID[9572897]
NPT484 Individual protein Luciferin 4-monooxygenase Photinus pyralis EC50 > 112219.0 nM PubChem BioAssay data set
NPT4770 Individual protein High-affinity choline transporter Homo sapiens IC50 n.a. 739.9 nM PubChem BioAssay data set
NPT4770 Individual protein High-affinity choline transporter Homo sapiens IC50 n.a. 335.52 nM PubChem BioAssay data set
NPT973 Individual protein Serotonin 1b (5-HT1b) receptor Homo sapiens Inhibition < 50.0 % PMID[27933810]
NPT20556 Single protein Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 21.24 % DOI[10.6019/CHEMBL4495564]
NPT20556 Single protein Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.3454 % DOI[10.6019/CHEMBL4495564]
NPT692 Individual protein Histone deacetylase 6 Homo sapiens Inhibition = 0.98 % 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 = -11.41 % HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT2554 Protein family Adenosine A2 receptor Rattus norvegicus Ki = 63.0 nM PMID[3336027]
NPT2554 Protein family Adenosine A2 receptor Rattus norvegicus EC25 = 13.0 nM PMID[3336027]
NPT1774 Protein family Sodium channel alpha subunits; brain (Types I, II, III) Homo sapiens Inhibition = 1.3 % PMID[2579237]
NPT1774 Protein family Sodium channel alpha subunits; brain (Types I, II, III) Homo sapiens Inhibition = 3.5 % PMID[2579237]
NPT2554 Protein family Adenosine A2 receptor Rattus norvegicus Ratio = 63.0 nM PMID[1738138]
NPT2554 Protein family Adenosine A2 receptor Rattus norvegicus IC50 = 160.0 nM PMID[1875349]
NPT2554 Protein family Adenosine A2 receptor Rattus norvegicus Ki = 63.1 nM PMID[2995663]
NPT4059 Individual protein Adenosine A2b receptor Homo sapiens logEC50 = -3.724 n.a. PMID[18321038]
NPT4059 Individual protein Adenosine A2b receptor Homo sapiens Activity = -0.889 n.a. PMID[18321038]
NPT4059 Individual protein Adenosine A2b receptor Homo sapiens Ki = 21400.0 nM PMID[19569717]
NPT4059 Individual protein Adenosine A2b receptor Homo sapiens Ki = 25500.0 nM PMID[19569717]
NPT93 Individual protein Survival motor neuron protein Homo sapiens Potency = 35481.3 nM PubChem BioAssay data set
NPT4446 Individual protein Eukaryotic translation initiation factor 2-alpha kinase 3 Homo sapiens EC50 > 55700.0 nM PubChem BioAssay data set
NPT4625 Individual protein Vasopressin V1b receptor Homo sapiens Potency n.a. 19438.4 nM PubChem BioAssay data set
NPT478 Individual protein Ataxin-2 Homo sapiens Potency n.a. 28183.8 nM PubChem BioAssay data set
NPT8 Individual protein DNA polymerase iota Homo sapiens Potency n.a. 25118.9 nM PubChem BioAssay data set
NPT861 Individual protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 18356.4 nM PubChem BioAssay data set
NPT92 Individual protein Serotonin 1a (5-HT1a) receptor Homo sapiens Inhibition < 50.0 % PMID[27933810]
NPT918 Individual protein Heat shock protein HSP 90-alpha Homo sapiens Inhibition > 45.0 % PMID[28933546]
NPT918 Individual protein Heat shock protein HSP 90-alpha Homo sapiens IC50 <= 1250000.0 nM PMID[28933546]
NPT918 Individual protein Heat shock protein HSP 90-alpha Homo sapiens Kd = 38000.0 nM PMID[33738064]
NPT918 Individual protein Heat shock protein HSP 90-alpha Homo sapiens Ki = 2200.0 nM PMID[33738064]
NPT4262 Individual protein Adenosine A2a receptor Cavia porcellus Ki = 8.0 nM PMID[6279840]
NPT5444 Protein family Adenosine receptor Rattus norvegicus Ki = 920.0 nM PMID[6279840]
NPT5444 Protein family Adenosine receptor Rattus norvegicus Ki = 9.0 nM PMID[6279840]
NPT5444 Protein family Adenosine receptor Rattus norvegicus Ki = 1.3 nM PMID[6279840]
NPT5444 Protein family Adenosine receptor Rattus norvegicus Ki = 10.0 nM PMID[6279840]
NPT4262 Individual protein Adenosine A2a receptor Cavia porcellus EC50 = 8000.0 nM PMID[2984420]
NPT536 Nucleic acid microRNA 21 Homo sapiens Potency = 116.7 nM PubChem BioAssay data set
NPT56 Individual protein Beta-lactamase AmpC Escherichia coli K-12 Potency = 70794.6 nM PubChem BioAssay data set
NPT539 Individual protein Cellular tumor antigen p53 Homo sapiens Potency = 19952.6 nM PubChem BioAssay data set
NPT539 Individual protein Cellular tumor antigen p53 Homo sapiens Potency = 15848.9 nM PubChem BioAssay data set
NPT49 Individual protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 31622.8 nM PubChem BioAssay data set
NPT49 Individual protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 5011.9 nM PubChem BioAssay data set
NPT974 Individual protein Serotonin 1d (5-HT1d) receptor Homo sapiens Inhibition < 50.0 % PMID[27933810]
NPT4011 Individual protein Serotonin 4 (5-HT4) receptor Homo sapiens Inhibition < 50.0 % PMID[27933810]
NPT425 Individual protein Serotonin 3a (5-HT3a) receptor Homo sapiens Inhibition < 50.0 % PMID[27933810]
NPT5100 Individual protein Phosphodiesterase 2A Homo sapiens IC50 > 10000.0 nM PMID[29174506]
NPT5100 Individual protein Phosphodiesterase 2A Homo sapiens Inhibition = 1.83 % PMID[29174506]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1171 Cell line HEp-2 Homo sapiens IC50 = 3000.0 nM PMID[1732556]
NPT137 Cell line L1210 Mus musculus IC50 < 3000.0 nM PMID[1732556]
NPT404 Cell line CCRF-CEM Homo sapiens IC50 = 10000.0 nM PMID[1732556]
NPT111 Cell line K562 Homo sapiens IC50 = 15400.0 nM PMID[16033277]
NPT111 Cell line K562 Homo sapiens IC50 = 19500.0 nM PMID[16033277]
NPT139 Cell line HT-29 Homo sapiens IC50 = 85600.0 nM PMID[16033277]
NPT83 Cell line MCF7 Homo sapiens IC50 = 72600.0 nM PMID[16033277]
NPT65 Cell line HepG2 Homo sapiens Potency n.a. 35481.3 nM PubChem BioAssay data set
NPT71 Cell line HEK293 Homo sapiens Potency n.a. 29092.9 nM PubChem BioAssay data set
NPT5443 Others Adenosine receptors; A1 & A2a Rattus norvegicus Ratio = 1.1 n.a. PMID[1766003]
NPT4757 Others Adenosine receptors; A1 & A2 Homo sapiens Ratio = 9.1 n.a. PMID[2016707]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 7943.28 nM PMID[19734910]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 10000.0 nM PMID[19734910]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 6309.57 nM PMID[19734910]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 6573.3 nM PubChem BioAssay data set
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 9285.0 nM PubChem BioAssay data set
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 72.48 % DOI[10.21203/rs.3.rs-23951/v1]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC37 = 11.0 uM PMID[30964283]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.35 % DOI[10.6019/CHEMBL4495565]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.16 % DOI[10.6019/CHEMBL4495565]
NPT2687 Others Adenosine receptor A2a and A3 Rattus norvegicus Ratio = 0.033 n.a. PMID[7932588]
NPT20 Organism Candida albicans Candida albicans Inhibition = 4.78 % DOI[10.6019/CHEMBL4513141]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae Inhibition = 2.26 % DOI[10.6019/CHEMBL4513141]
NPT4749 Others Adenosine receptors; A1 & A2 Rattus norvegicus Ratio = 6.8 n.a. PMID[1738138]
NPT4749 Others Adenosine receptors; A1 & A2 Rattus norvegicus Ratio = 0.23 n.a. PMID[1875349]
NPT4749 Others Adenosine receptors; A1 & A2 Rattus norvegicus Ratio = 7.22 n.a. PMID[2995663]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 3.01 % DOI[10.6019/CHEMBL4513141]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 14.41 % DOI[10.6019/CHEMBL4513141]
NPT2555 Others Adenosine receptors; A1 & A3 Rattus norvegicus Ratio = 0.0049 n.a. PMID[7932588]
NPT2 Others Unspecified n.a. IC50 = 460.0 nM PMID[1766003]
NPT2 Others Unspecified n.a. Ki > 100000.0 nM PMID[19731917]
NPT2 Others Unspecified n.a. Inhibition = 1.0 % PMID[19731917]
NPT2 Others Unspecified n.a. EC50 < 701.0 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 7307.8 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 366.3 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 4466.8 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 920.0 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 20596.2 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Ki = 9650.0 nM PMID[24283924]
NPT2 Others Unspecified n.a. Potency n.a. 22387.2 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 31622.8 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 14125.4 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 35481.3 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 39810.7 nM PubChem BioAssay data set
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii Inhibition = 9.97 % DOI[10.6019/CHEMBL4513141]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT29 Organism Rattus norvegicus Rattus norvegicus IC50 = 620.0 nM PMID[1433217]
NPT29 Organism Rattus norvegicus Rattus norvegicus ED25 = 0.015 mg kg-1 PMID[1875349]
NPT29 Organism Rattus norvegicus Rattus norvegicus Delta HR = -25.0 % PMID[1875349]





 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
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 NPC269827 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score Similarity Level Natural Product ID
0.7258 Intermediate Similarity NPC472816
0.7258 Intermediate Similarity NPC600171
0.7069 Intermediate Similarity NPC599876
0.6667 Remote Similarity NPC156461
0.6667 Remote Similarity NPC107374
0.6667 Remote Similarity NPC600382
0.6667 Remote Similarity NPC612067
0.6552 Remote Similarity NPC609036
0.6441 Remote Similarity NPC164665
0.6338 Remote Similarity NPC611003
0.6333 Remote Similarity NPC189068
0.5556 Remote Similarity NPC608983
0.55 Remote Similarity NPC317821
0.5385 Remote Similarity NPC136349
0.5385 Remote Similarity NPC219313
0.5161 Remote Similarity NPC54320
0.5156 Remote Similarity NPC321052
0.5079 Remote Similarity NPC311197

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC269827 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
1.0 High Similarity NPD195 Approved
0.7258 Intermediate Similarity NPD242 Phase 4
0.7069 Intermediate Similarity NPD185 Phase 4
0.6949 Remote Similarity NPD166 Phase 4
0.6667 Remote Similarity NPD249 Phase 4
0.6667 Remote Similarity NPD250 Phase 4
0.5397 Remote Similarity NPD186 Phase 1
0.5385 Remote Similarity NPD548 Clinical (unspecified phase)
0.5342 Remote Similarity NPD2647 Phase 3
0.5278 Remote Similarity NPD3107 Discontinued
0.5195 Remote Similarity NPD2902 Phase 2
0.5195 Remote Similarity NPD2903 Clinical (unspecified phase)
0.5161 Remote Similarity NPD219 Phase 4
0.5161 Remote Similarity NPD220 Clinical (unspecified phase)

Bioactivity similarity

  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