Natural Product: NPC237635

Natural Product IDNPC237635
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Warangalone
IUPAC Name 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one
Synonyms Warangalone
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL458134
PubChem CID 5379679
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0001612] Isoflavans
          • [CHEMONTID:0001827] Isoflavanones
            • [CHEMONTID:0003526] 6-prenylated isoflavanones

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 HGHOPAZIUPORIN-UHFFFAOYSA-N
Standard InCHI InChI=1S/C25H24O5/c1-14(2)5-10-18-23-17(11-12-25(3,4)30-23)21(27)20-22(28)19(13-29-24(18)20)15-6-8-16(26)9-7-15/h5-9,11-13,26-27H,10H2,1-4H3
SMILES CC(=CCc1c2c(C=CC(C)(C)O2)c(c2c(=O)c(coc12)c1ccc(cc1)O)O)C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   404.16 Volume:   424.317
?
Van der Waals volume.
Dense:   0.952 LogP:   4.389
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.64
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -5.097
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   3.0 Rigid Bonds:   24.0
TPSA:   79.9
?
Topological Polar Surface Area.
 H-Bond Acceptor:   5.0
H-Bond Donor:   2.0 Rings:   4.0
Heavy Atoms:   5.0

MedChem Properties

QED Drug-Likeness Score:   0.558 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.141 Fsp3:   0.24
MCE-18:   53.677
?
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:   0.988 Fluc inhibitor:   0.394
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.852
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.714
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.23 Promiscuous compounds:   0.117

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -5.031 MDCK Permeability:   -4.689
Pgp-inhibitor:   0.675 Pgp-substrate:   0.006
PAMPA:   0.935
?
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):   0.006
20% Bioavailability (F20%):   0.91 30% Bioavailability (F30%):   0.985
50% Bioavailability (F50%):   0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.129 MRP1:   0.928
Plasma Protein Binding (PPB):   95.593% Volume Distribution (VD):   0.139
Fu: 3.806%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   1.0
OATP1B3 inhibitor:   0.687 BCRP inhibitor:   0.826
BSEP inhibitor:   0.995

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   1.0
CYP2C19-inhibitor:   0.994 CYP2C19-substrate:   1.0
CYP2C9-inhibitor:   0.577 CYP2C9-substrate:   0.047
CYP2D6-inhibitor:   0.345 CYP2D6-substrate:   0.174
CYP3A4-inhibitor:   0.147 CYP3A4-substrate:   1.0
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   1.0
?
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):  4.04 Half-life (T1/2):  1.276

ADMET: Toxicity

hERG Blockers:  0.104 hERG Blockers (10um):  0.584
Human Hepatotoxicity (H-HT):  0.602 Drug-induced Liver Injury (DILI):  0.573
AMES Toxicity:  0.622 Rat Oral Acute Toxicity:  0.815
Maximum Recommended Daily Dose:  0.746 Skin Sensitization:  0.824
Carcinogencity:  0.73 Eye Corrosion:  0.0
Eye Irritation:  0.553 Respiratory Toxicity:  0.877
Drug-induced Neurotoxicity:  0.529 Ototoxicity:  0.456
Hematotoxicity:  0.179 Drug-induced Nephrotoxicity:  0.385
Genotoxicity:  0.881 RPMI-8226 Immunitoxicity:  0.054
A549 Cytotoxicity:  0.208 Hek293 Cytotoxicity:  0.621
BCF:   1.9
?
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:   5.112
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   6.833
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   6.307
?
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
NPO27553 Derris scandens Species Fabaceae Eukaryota n.a. stem n.a. DOI[10.1016/S0031-9422(99)00103-X]
NPO29113 Erythrina vogelii Species Fabaceae Eukaryota root bark n.a. n.a. PMID[11908991]
NPO27387 Erythrina addisoniae Species Fabaceae Eukaryota Stems; Barks n.a. n.a. PMID[12828487]
NPO28587 Axinella weltneri Species n.a. n.a. n.a. n.a. n.a. PMID[16124780]
NPO27387 Erythrina addisoniae Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[17517504]
NPO27387 Erythrina addisoniae Species Fabaceae Eukaryota Barks n.a. n.a. PMID[18302333]
NPO27553 Derris scandens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[19969457]
NPO27387 Erythrina addisoniae Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[20934335]
NPO27553 Derris scandens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21314138]
NPO27387 Erythrina addisoniae Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23022281]
NPO28764 Phyllidia ocellata Species Phyllidiidae Eukaryota n.a. n.a. n.a. PMID[26056748]
NPO40204 Millettia extensa Species Fabaceae Eukaryota Stems n.a. n.a. PMID[30106294]
NPO40204 Millettia extensa Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[31403786]
NPO28587 Axinella weltneri Species n.a. n.a. n.a. n.a. n.a. PMID[9249974]
NPO28640 Alsidium corallinum Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12908 Euchresta japonica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17368 Erythrina senegalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28764 Phyllidia ocellata Species Phyllidiidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28553 Nannoglottis ravida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7845 Tephrosia elata Species Geometridae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27387 Erythrina addisoniae Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25617 Lactococcus lactis Species Streptococcaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO5436 Absidia caerulea Species Cunninghamellaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29181 Galdieria sulphuraria Species Cyanidiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28517 Hypericum caprifoliatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28399 Anthotroche myoporoides Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28535 Astragalus flexus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28944 Heliotropium digynum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28436 Helenium virginicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28587 Axinella weltneri Species n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO29056 Dactynotus ambrosiae n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO27553 Derris scandens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29113 Erythrina vogelii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17368 Erythrina senegalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12908 Euchresta japonica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27553 Derris scandens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7845 Tephrosia elata Species Geometridae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29113 Erythrina vogelii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27553 Derris scandens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7845 Tephrosia elata Species Geometridae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17368 Erythrina senegalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12908 Euchresta japonica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29113 Erythrina vogelii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28553 Nannoglottis ravida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7845 Tephrosia elata Species Geometridae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30362 Erythrina variegate Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5436 Absidia caerulea Species Cunninghamellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25617 Lactococcus lactis Species Streptococcaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17368 Erythrina senegalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29056 Dactynotus ambrosiae n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12908 Euchresta japonica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28436 Helenium virginicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28587 Axinella weltneri Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO7845 Tephrosia elata Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28944 Heliotropium digynum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28764 Phyllidia ocellata Species Phyllidiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29181 Galdieria sulphuraria Species Cyanidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28535 Astragalus flexus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28517 Hypericum caprifoliatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27553 Derris scandens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28553 Nannoglottis ravida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28399 Anthotroche myoporoides Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27387 Erythrina addisoniae Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29113 Erythrina vogelii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28640 Alsidium corallinum Species Rhodomelaceae 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
NPT113 Cell line RAW264.7 Mus musculus IC50 = 8500.0 nM PMID[31403786]
NPT113 Cell line RAW264.7 Mus musculus Activity = 86.5 % PMID[31403786]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium MIC = 128.0 ug.mL-1 PMID[30106294]
NPT2747 Organism Achaea janata Achaea janata Activity = 63.6 % PMID[19969457]
NPT2747 Organism Achaea janata Achaea janata Activity = 50.3 % PMID[19969457]
NPT2747 Organism Achaea janata Achaea janata Activity = 5.5 % PMID[19969457]
NPT2747 Organism Achaea janata Achaea janata Activity = 11.8 % PMID[19969457]
NPT2747 Organism Achaea janata Achaea janata Activity = 633.2 mg PMID[19969457]
NPT2747 Organism Achaea janata Achaea janata Activity = 572.6 mg PMID[19969457]
NPT2747 Organism Achaea janata Achaea janata TIME = 280.8 hr PMID[19969457]
NPT2747 Organism Achaea janata Achaea janata TIME = 285.6 hr PMID[19969457]
NPT2747 Organism Achaea janata Achaea janata TIME = 225.6 hr PMID[19969457]
NPT2747 Organism Achaea janata Achaea janata TIME = 235.2 hr PMID[19969457]
NPT2747 Organism Achaea janata Achaea janata Activity = 6.8 % PMID[19969457]
NPT2747 Organism Achaea janata Achaea janata AFI = 6.2 % PMID[19969457]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 2.0 ug.mL-1 PMID[30106294]
NPT20967 Cell line Platelet n.a. Inhibition < 20.0 % PMID[12828487]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 2.0 ug.mL-1 PMID[30106294]
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis MIC = 4.0 ug.mL-1 PMID[30106294]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 128.0 ug.mL-1 PMID[30106294]
NPT2 Others Unspecified n.a. IC50 = 3500.0 nM PMID[12828487]
NPT2 Others Unspecified n.a. Inhibition < 20.0 % PMID[12828487]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT32 Organism Mus musculus Mus musculus Inhibition = 21.0 % PMID[12828487]
NPT32 Organism Mus musculus Mus musculus ID50 = 0.54 umol PMID[12828487]
NPT32 Organism Mus musculus Mus musculus Inhibition = 68.0 % PMID[12828487]
NPT32 Organism Mus musculus Mus musculus Inhibition = 78.0 % PMID[12828487]
NPT32 Organism Mus musculus Mus musculus Inhibition = 41.0 % PMID[12828487]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 63.4 % PMID[21314138]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 60.0 % PMID[21314138]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 50.1 % PMID[21314138]
NPT2745 Organism Rhyzopertha dominica Rhyzopertha dominica mortality = 21.8 % PMID[21314138]
NPT2745 Organism Rhyzopertha dominica Rhyzopertha dominica mortality = 18.6 % PMID[21314138]
NPT2745 Organism Rhyzopertha dominica Rhyzopertha dominica mortality = 15.8 % PMID[21314138]
NPT2747 Organism Achaea janata Achaea janata mortality = 17.8 % PMID[19969457]
NPT2747 Organism Achaea janata Achaea janata mortality = 27.6 % PMID[19969457]
NPT2747 Organism Achaea janata Achaea janata mortality = 0.0 % PMID[19969457]
NPT1419 Organism Tribolium castaneum Tribolium castaneum mortality = 37.2 % PMID[21314138]
NPT1419 Organism Tribolium castaneum Tribolium castaneum mortality = 32.8 % PMID[21314138]
NPT1419 Organism Tribolium castaneum Tribolium castaneum mortality = 30.7 % PMID[21314138]
NPT2721 Organism Callosobruchus chinensis Callosobruchus chinensis mortality = 31.4 % PMID[21314138]
NPT2721 Organism Callosobruchus chinensis Callosobruchus chinensis mortality = 29.1 % PMID[21314138]
NPT2721 Organism Callosobruchus chinensis Callosobruchus chinensis mortality = 27.9 % PMID[21314138]





 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
- Tribolium castaneum LC50 > 1.0 ug.mL-1 PMID[21314138]
- Callosobruchus chinensis LC50 > 1.0 ug.mL-1 PMID[21314138]
- Rhyzopertha dominica LC50 > 1.0 ug.mL-1 PMID[21314138]
- Sitophilus oryzae LC50 = 0.84 ug.mL-1 PMID[21314138]

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 NPC237635 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
0.8769 High Similarity NPC170026
0.8382 Intermediate Similarity NPC200625
0.7746 Intermediate Similarity NPC188403
0.7681 Intermediate Similarity NPC201731
0.7612 Intermediate Similarity NPC6511
0.7324 Intermediate Similarity NPC484044
0.6849 Remote Similarity NPC327269
0.6757 Remote Similarity NPC79469
0.6757 Remote Similarity NPC282307
0.6711 Remote Similarity NPC470681
0.6711 Remote Similarity NPC28241
0.6575 Remote Similarity NPC214236
0.6494 Remote Similarity NPC91701
0.6486 Remote Similarity NPC31627
0.6486 Remote Similarity NPC14001
0.6429 Remote Similarity NPC97716
0.6143 Remote Similarity NPC204985
0.5972 Remote Similarity NPC24673
0.5789 Remote Similarity NPC29876
0.5775 Remote Similarity NPC144118
0.5769 Remote Similarity NPC244407
0.575 Remote Similarity NPC476238
0.5714 Remote Similarity NPC220418
0.5714 Remote Similarity NPC103238
0.5676 Remote Similarity NPC219917
0.5652 Remote Similarity NPC483565
0.5625 Remote Similarity NPC201829
0.5616 Remote Similarity NPC600644
0.5584 Remote Similarity NPC117836
0.5584 Remote Similarity NPC51887
0.557 Remote Similarity NPC204879
0.557 Remote Similarity NPC328102
0.5556 Remote Similarity NPC259166
0.5513 Remote Similarity NPC608569
0.5405 Remote Similarity NPC488812
0.5385 Remote Similarity NPC84124
0.5309 Remote Similarity NPC233502
0.5238 Remote Similarity NPC302762
0.5217 Remote Similarity NPC295384
0.52 Remote Similarity NPC171916
0.519 Remote Similarity NPC219861
0.5185 Remote Similarity NPC484043
0.5181 Remote Similarity NPC238064
0.5181 Remote Similarity NPC218871
0.5135 Remote Similarity NPC478987
0.5125 Remote Similarity NPC256406
0.5119 Remote Similarity NPC278968
0.5062 Remote Similarity NPC184755
0.506 Remote Similarity NPC604503

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC237635 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
NPD

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