Natural Product: NPC229974

Natural Product IDNPC229974
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Cordycepin
IUPAC Name (2R,3R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
Synonyms 3'-Deoxyadenosine; Cordycepin
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL305686
PubChem CID 6303
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues
      • [CHEMONTID:0000479] Purine nucleosides
        • [CHEMONTID:0002178] Purine 3'-deoxyribonucleosides

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 OFEZSBMBBKLLBJ-BAJZRUMYSA-N
Standard InCHI InChI=1S/C10H13N5O3/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(17)1-5(2-16)18-10/h3-6,10,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,10+/m0/s1
SMILES C1[C@@H](CO)O[C@H]([C@@H]1O)n1cnc2c(N)ncnc12

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   251.1 Volume:   226.656
?
Van der Waals volume.
Dense:   1.108 LogP:   -0.439
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   -0.123
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -1.617
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   2.0 Rigid Bonds:   15.0
TPSA:   119.31
?
Topological Polar Surface Area.
 H-Bond Acceptor:   8.0
H-Bond Donor:   4.0 Rings:   3.0
Heavy Atoms:   8.0

MedChem Properties

QED Drug-Likeness Score:   0.629 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.632 Fsp3:   0.5
MCE-18:   56.533
?
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:   0.111 Fluc inhibitor:   0.006
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.051
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.015
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.036 Promiscuous compounds:   0.499

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.769 MDCK Permeability:   -5.422
Pgp-inhibitor:   0.001 Pgp-substrate:   0.654
PAMPA:   0.92
?
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):   0.209
20% Bioavailability (F20%):   0.134 30% Bioavailability (F30%):   0.771
50% Bioavailability (F50%):   0.508

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.381 MRP1:   0.235
Plasma Protein Binding (PPB):   10.597% Volume Distribution (VD):   -0.034
Fu: 91.403%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.993
OATP1B3 inhibitor:   0.985 BCRP inhibitor:   0.024
BSEP inhibitor:   0.004

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.0 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   0.021 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.017 CYP2D6-substrate:   0.049
CYP3A4-inhibitor:   0.002 CYP3A4-substrate:   0.0
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.009
HLM stability:   0.039
?
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):  10.335 Half-life (T1/2):  2.02

ADMET: Toxicity

hERG Blockers:  0.06 hERG Blockers (10um):  0.208
Human Hepatotoxicity (H-HT):  0.811 Drug-induced Liver Injury (DILI):  0.977
AMES Toxicity:  0.955 Rat Oral Acute Toxicity:  0.42
Maximum Recommended Daily Dose:  0.395 Skin Sensitization:  0.951
Carcinogencity:  0.837 Eye Corrosion:  0.0
Eye Irritation:  0.608 Respiratory Toxicity:  0.599
Drug-induced Neurotoxicity:  0.977 Ototoxicity:  0.764
Hematotoxicity:  0.803 Drug-induced Nephrotoxicity:  0.779
Genotoxicity:  0.998 RPMI-8226 Immunitoxicity:  0.16
A549 Cytotoxicity:  0.311 Hek293 Cytotoxicity:  0.436
BCF:   -0.016
?
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:   1.967
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   3.599
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   2.534
?
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
NPO32693 cordyceps militaris bcc 2816 Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[15568800]
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
NPT1758 Individual protein Hepatitis C virus NS5B RNA-dependent RNA polymerase Hepatitis C virus IC50 = 22000.0 nM PMID[15084127]
NPT1758 Individual protein Hepatitis C virus NS5B RNA-dependent RNA polymerase Hepatitis C virus EC50 n.a. 46000.0 nM PMID[15084127]
NPT1315 Individual protein Adenosine A1 receptor Rattus norvegicus Ki = 7120.0 nM PMID[9371242]
NPT1315 Individual protein Adenosine A1 receptor Rattus norvegicus Ki = 15200.0 nM PMID[9371242]
NPT1315 Individual protein Adenosine A1 receptor Rattus norvegicus Ratio = 2.1 n.a. PMID[9371242]
NPT1273 Individual protein ATP-dependent molecular chaperone HSP82 Candida albicans (strain WO-1) (Yeast) EC50 > 150000.0 nM PubChem BioAssay data set
NPT1754 Individual protein Adenosine deaminase Bos taurus Stability n.a. n.a. % PMID[36417756]
NPT25484 Single protein Sterol 14-alpha demethylase Trypanosoma cruzi (strain CL Brener) IC50 > 100000.0 nM DOI[10.6019/CHEMBL3430912]
NPT20556 Single protein Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 19.48 % DOI[10.6019/CHEMBL4495564]
NPT20556 Single protein Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 16.8 % DOI[10.6019/CHEMBL4495564]
NPT692 Individual protein Histone deacetylase 6 Homo sapiens Inhibition = 4.37 % 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 = -9.63 % HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT5055 Individual protein Mitochondrial import inner membrane translocase subunit TIM23 Saccharomyces cerevisiae S288c IC50 = 14000.0 nM PubChem BioAssay data set

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT189 Cell line Vero Chlorocebus aethiops IC50 = 0.5 nM PMID[10464017]
NPT25 Cell line MT4 Homo sapiens CD50 = 45.0 uM PMID[3172142]
NPT25 Cell line MT4 Homo sapiens Selectivity index < 0.5 n.a. PMID[3172142]
NPT112 Cell line MOLT-4 Homo sapiens IC50 >= 100000.0 nM PMID[24283924]
NPT1460 Cell line L929 Mus musculus IC50 = 28700.0 nM PMID[24283924]
NPT112 Cell line MOLT-4 Homo sapiens IC50 = 100.0 nM PMID[24283924]
NPT65 Cell line HepG2 Homo sapiens IC50 > 100000.0 nM DOI[10.6019/CHEMBL3430912]
NPT886 Cell line NIH3T3 Mus musculus IC50 > 50118.72 nM DOI[10.6019/CHEMBL3430912]
NPT2186 Cell line RL Homo sapiens Imax = 17.0 % PMID[36417756]
NPT2186 Cell line RL Homo sapiens FC = 2.0 n.a. PMID[36417756]
NPT15 Cell line Jurkat Homo sapiens Imax = 20.0 % PMID[36417756]
NPT1081 Cell line BXPC-3 Homo sapiens Imax = 22.0 % PMID[36417756]
NPT783 Cell line MIA PaCa-2 Homo sapiens Imax = 35.0 % PMID[36417756]
NPT111 Cell line K562 Homo sapiens Imax = 88.0 % PMID[36417756]
NPT139 Cell line HT-29 Homo sapiens Imax = 44.0 % PMID[36417756]
NPT65 Cell line HepG2 Homo sapiens Imax = 66.0 % PMID[36417756]
NPT83 Cell line MCF7 Homo sapiens Imax = 78.0 % PMID[36417756]
NPT1649 Cell line MV4-11 Homo sapiens Imax = 1.0 % PMID[36417756]
NPT112 Cell line MOLT-4 Homo sapiens Imax = 52.0 % PMID[36417756]
NPT389 Cell line RPMI-8226 Homo sapiens Imax = 1.0 % PMID[36417756]
NPT404 Cell line CCRF-CEM Homo sapiens FC = 2.0 n.a. PMID[36417756]
NPT323 Cell line SW-620 Homo sapiens Imax = 10.0 % PMID[36417756]
NPT404 Cell line CCRF-CEM Homo sapiens Imax = 12.0 % PMID[36417756]
NPT116 Cell line HL-60 Homo sapiens Imax = 88.0 % PMID[36417756]
NPT1970 Cell line THP-1 Homo sapiens Imax = -3.0 % PMID[36417756]
NPT404 Cell line CCRF-CEM Homo sapiens FC = 16.0 n.a. PMID[36417756]
NPT335 Organism Human coxsackievirus B4 Human coxsackievirus B4 MIC > 100.0 ug.mL-1 PMID[1335077]
NPT856 Organism Semliki forest virus Semliki forest virus MIC > 100.0 ug.mL-1 PMID[1335077]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 14.13 % DOI[10.21203/rs.3.rs-23951/v1]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.0 % DOI[10.6019/CHEMBL4495565]
NPT20555 Organism SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.03 % 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]
NPT28438 Unchecked Unchecked n.a. Imax = 2.0 % PMID[36417756]
NPT30075 Cell line KG-1 Homo sapiens Imax = 78.0 % PMID[36417756]
NPT28438 Unchecked Unchecked n.a. Activity n.a. n.a. n.a. PMID[36417756]
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 MIC > 40.0 ug.mL-1 PMID[1335077]
NPT1141 Organism Human herpesvirus 2 Human herpesvirus 2 MIC > 40.0 ug.mL-1 PMID[1335077]
NPT334 Organism Vaccinia virus Vaccinia virus MIC > 100.0 ug.mL-1 PMID[1335077]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 > 50118.72 nM DOI[10.6019/CHEMBL3430912]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 5011.87 nM DOI[10.6019/CHEMBL3430912]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 1122.02 nM DOI[10.6019/CHEMBL3430912]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 1995.26 nM DOI[10.6019/CHEMBL3430912]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 1258.93 nM DOI[10.6019/CHEMBL3430912]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi EC50 = 2510.0 nM PMID[30234983]
NPT25683 Cell line Z-138 Homo sapiens Imax = 95.0 % PMID[36417756]
NPT28186 Cell line HEL 92.1.7 Homo sapiens Imax = 88.0 % PMID[36417756]
NPT1106 Organism Human poliovirus 1 Human poliovirus 1 MIC > 100.0 ug.mL-1 PMID[1335077]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 MIC > 4.0 ug.mL-1 PMID[1335077]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 ED50 > 50.0 uM PMID[3172142]
NPT1018 Organism Trypanosoma brucei Trypanosoma brucei IC50 = 42.0 nM PMID[24283924]
NPT1018 Organism Trypanosoma brucei Trypanosoma brucei IC50 = 32.0 nM PMID[24283924]
NPT1018 Organism Trypanosoma brucei Trypanosoma brucei IC50 = 1.2 nM PMID[24283924]
NPT191 Organism Hepatitis C virus Hepatitis C virus EC50 = 70000.0 nM PMID[25282652]
NPT24234 Cell line NCI-H929 Homo sapiens Imax = 24.0 % PMID[36417756]
NPT195 Organism Vesicular stomatitis virus Vesicular stomatitis virus MIC > 40.0 ug.mL-1 PMID[1335077]
NPT195 Organism Vesicular stomatitis virus Vesicular stomatitis virus MIC > 100.0 ug.mL-1 PMID[1335077]
NPT336 Organism Human parainfluenza virus 3 Human parainfluenza virus 3 MIC > 100.0 ug.mL-1 PMID[1335077]
NPT3878 Organism Mammalian orthoreovirus 1 Mammalian orthoreovirus 1 MIC > 100.0 ug.mL-1 PMID[1335077]
NPT338 Organism Sindbis virus Sindbis virus MIC > 100.0 ug.mL-1 PMID[1335077]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 4.5 ug.mL-1 PMID[15568800]
NPT2 Others Unspecified n.a. EC50 = 4100.0 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. EC50 > 150000.0 nM PubChem BioAssay data set
NPT1019 Organism Trichomonas vaginalis Trichomonas vaginalis GI = 94.1 % PMID[22579483]
NPT2 Others Unspecified n.a. Potency n.a. 44668.4 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 10000.0 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Ki = 180.0 nM PMID[24283924]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 = 30.0 nM PMID[24283924]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 = 12.59 nM DOI[10.6019/CHEMBL3430912]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 = 10.0 nM DOI[10.6019/CHEMBL3430912]
NPT2 Others Unspecified n.a. Ratio CC50/EC50 = 0.19 n.a. PMID[25282652]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT29 Organism Rattus norvegicus Rattus norvegicus GTP shift = 2.1 n.a. PMID[7562934]





 Experimental ADME

Experiment Model Experiment Tissue ADME Type ADME Relation ADME Value ADME Unit Reference
n.a. n.a. Drug metabolism = 0.012 L/mol/min PMID[34213340]
Mus musculus Plasma T1/2 = 0.4167 hr PMID[36417756]
Homo sapiens Plasma T1/2 = 1.033 hr PMID[36417756]
Homo sapiens Plasma T1/2 = 4.2 hr PMID[36417756]





 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 NPC229974 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
0.7547 Intermediate Similarity NPC156461
0.7547 Intermediate Similarity NPC107374
0.7547 Intermediate Similarity NPC600382
0.7547 Intermediate Similarity NPC612067
0.717 Intermediate Similarity NPC317821
0.6786 Remote Similarity NPC209525
0.6786 Remote Similarity NPC161659
0.6379 Remote Similarity NPC609472
0.6333 Remote Similarity NPC136349
0.6333 Remote Similarity NPC219313
0.6324 Remote Similarity NPC481375
0.6316 Remote Similarity NPC33996
0.629 Remote Similarity NPC85689
0.6271 Remote Similarity NPC309832
0.6 Remote Similarity NPC328479
0.5846 Remote Similarity NPC185991
0.5846 Remote Similarity NPC321814
0.5781 Remote Similarity NPC211025
0.5672 Remote Similarity NPC164952
0.5588 Remote Similarity NPC302778
0.5588 Remote Similarity NPC329404
0.5588 Remote Similarity NPC212551
0.5571 Remote Similarity NPC324484
0.5522 Remote Similarity NPC121222
0.5507 Remote Similarity NPC324198
0.5507 Remote Similarity NPC326529
0.5507 Remote Similarity NPC319100
0.5429 Remote Similarity NPC130586
0.5417 Remote Similarity NPC325906
0.5417 Remote Similarity NPC606116
0.541 Remote Similarity NPC604998
0.5278 Remote Similarity NPC174802
0.5205 Remote Similarity NPC606410
0.5161 Remote Similarity NPC609036
0.5147 Remote Similarity NPC239737
0.5135 Remote Similarity NPC316618
0.5135 Remote Similarity NPC323091
0.5079 Remote Similarity NPC164665
0.5067 Remote Similarity NPC607463

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC229974 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
0.7547 Intermediate Similarity NPD249 Phase 4
0.7547 Intermediate Similarity NPD250 Phase 4
0.6552 Remote Similarity NPD193 Phase 2
0.6333 Remote Similarity NPD548 Clinical (unspecified phase)
0.5846 Remote Similarity NPD283 Phase 4
0.5672 Remote Similarity NPD4171 Clinical (unspecified phase)
0.5507 Remote Similarity NPD338 Approved
0.5417 Remote Similarity NPD1777 Phase 4
0.5323 Remote Similarity NPD186 Phase 1
0.5278 Remote Similarity NPD339 Phase 2
0.527 Remote Similarity NPD1776 Approved
0.5217 Remote Similarity NPD1369 Phase 2
0.5217 Remote Similarity NPD1750 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