Natural Product: NPC99659

Natural Product IDNPC99659
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Glaucine
IUPAC Name (6aS)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
Synonyms Glaucine
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL228082
PubChem CID 16754
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0000381] Aporphines

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 RUZIUYOSRDWYQF-HNNXBMFYSA-N
Standard InCHI InChI=1S/C21H25NO4/c1-22-7-6-12-9-18(25-4)21(26-5)20-14-11-17(24-3)16(23-2)10-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3/t15-/m0/s1
SMILES COc1cc2c(cc1OC)C[C@H]1c3c2c(OC)c(OC)cc3CCN1C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   355.18 Volume:   367.885
?
Van der Waals volume.
Dense:   0.965 LogP:   2.258
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.479
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.284
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   4.0 Rigid Bonds:   20.0
TPSA:   40.16
?
Topological Polar Surface Area.
 H-Bond Acceptor:   5.0
H-Bond Donor:   0.0 Rings:   4.0
Heavy Atoms:   5.0

MedChem Properties

QED Drug-Likeness Score:   0.84 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   2.929 Fsp3:   0.429
MCE-18:   75.133
?
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:   0 PAINS Alert:   0
Colloidal aggregators:   0.265 Fluc inhibitor:   0.046
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.649
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.248
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.004 Promiscuous compounds:   0.967

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.613 MDCK Permeability:   -4.627
Pgp-inhibitor:   0.444 Pgp-substrate:   0.797
PAMPA:   0.003
?
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):   0.134
20% Bioavailability (F20%):   0.559 30% Bioavailability (F30%):   0.433
50% Bioavailability (F50%):   0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.192 MRP1:   0.933
Plasma Protein Binding (PPB):   64.843% Volume Distribution (VD):   0.283
Fu: 30.923%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.935
OATP1B3 inhibitor:   0.986 BCRP inhibitor:   0.944
BSEP inhibitor:   0.973

ADMET: Metabolism

CYP1A2-inhibitor:   1.0 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   1.0 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   0.626 CYP2C9-substrate:   0.004
CYP2D6-inhibitor:   0.999 CYP2D6-substrate:   0.003
CYP3A4-inhibitor:   1.0 CYP3A4-substrate:   0.37
CYP2B6-substrate:   0.999 CYP2C8-inhibitor:   0.013
HLM stability:   0.273
?
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):  9.878 Half-life (T1/2):  3.101

ADMET: Toxicity

hERG Blockers:  0.455 hERG Blockers (10um):  0.716
Human Hepatotoxicity (H-HT):  0.531 Drug-induced Liver Injury (DILI):  0.046
AMES Toxicity:  0.54 Rat Oral Acute Toxicity:  0.735
Maximum Recommended Daily Dose:  0.911 Skin Sensitization:  0.521
Carcinogencity:  0.737 Eye Corrosion:  0.001
Eye Irritation:  0.076 Respiratory Toxicity:  0.934
Drug-induced Neurotoxicity:  0.898 Ototoxicity:  0.342
Hematotoxicity:  0.202 Drug-induced Nephrotoxicity:  0.297
Genotoxicity:  0.752 RPMI-8226 Immunitoxicity:  0.082
A549 Cytotoxicity:  0.203 Hek293 Cytotoxicity:  0.324
BCF:   2.295
?
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:   4.134
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.273
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.644
?
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
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. DOI[10.1042/BA20020118]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. DOI[10.1556/abot.45.2003.3-4.15]
NPO18509 Fissistigma oldhamii Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10978218]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[15019787]
NPO18509 Fissistigma oldhamii Species Annonaceae Eukaryota stem n.a. n.a. PMID[17081761]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota tubers n.a. n.a. PMID[20594848]
NPO28410 Nandina domestica Species Berberidaceae Eukaryota n.a. n.a. n.a. PMID[22029392]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[22029392]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[22737858]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[23194502]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[23517479]
NPO20441 Glaucium flavum Species Papaveraceae Eukaryota n.a. root n.a. PMID[24317429]
NPO28410 Nandina domestica Species Berberidaceae Eukaryota n.a. fruit n.a. PMID[24897106]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. rhizome n.a. PMID[25277281]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. tuber n.a. PMID[25670016]
NPO31526 Xylopia laevigata Species Annonaceae Eukaryota n.a. stem n.a. PMID[27399666]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[32058719]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[37685099]
NPO20441 Glaucium flavum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[38415909]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2466 Aloe microstigma Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7312 Aplidium multiplicatum Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10176 Chrozophora prostrata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20441 Glaucium flavum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28410 Nandina domestica Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29272 Paronychia argentea Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18509 Fissistigma oldhamii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29249 Prunus humilis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1005 Pycnarrhena novoguineensis Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota Latex Exudate n.a. n.a. Database[FooDB]
NPO20441 Glaucium flavum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28410 Nandina domestica Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29249 Prunus humilis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29514 Stizolobium capitatum n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29514 Stizolobium capitatum n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO28410 Nandina domestica Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20441 Glaucium flavum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29249 Prunus humilis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20441 Glaucium flavum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28410 Nandina domestica Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29249 Prunus humilis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29272 Paronychia argentea Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28410 Nandina domestica Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7312 Aplidium multiplicatum Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5075 Balaenoptera borealis Species Balaenopteridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2466 Aloe microstigma Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1005 Pycnarrhena novoguineensis Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15671 Iris decora Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10176 Chrozophora prostrata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2556 Platytaenia dasycarpa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO18509 Fissistigma oldhamii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28458 Coccoloba dugandiana Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29249 Prunus humilis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28873 Epinetrum mangenotii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO29514 Stizolobium capitatum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3020 Brickellia paniculata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1518 Pedicularis chinensis Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29235 Musca autumnalis Species Muscidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29520 Curculigo breviscapa Species Hypoxidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20441 Glaucium flavum Species Papaveraceae 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
NPO20441 Glaucium flavum n.a. n.a. 52.15 n.a. n.a. % PMID[38415909]
NPO20441 Glaucium flavum n.a. n.a. 13.67 n.a. n.a. % PMID[38415909]
NPO20441 Glaucium flavum n.a. n.a. 82.75 n.a. n.a. % PMID[38415909]

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
NPT1857 Individual protein Dopamine D1 receptor Rattus norvegicus Ki = 2900.0 nM PMID[17228858]
NPT1858 Individual protein Dopamine D2 receptor Rattus norvegicus Ki = 2800.0 nM PMID[17228858]
NPT290 Individual protein Serotonin 2a (5-HT2a) receptor Homo sapiens Ki = 966.0 nM PMID[25695425]
NPT1785 Individual protein Serotonin 7 (5-HT7) receptor Homo sapiens Ki = 43.0 nM PMID[25695425]
NPT1594 Individual protein Multidrug resistance-associated protein 1 Homo sapiens FC = 22.0 n.a. PMID[28675836]
NPT291 Individual protein Serotonin 2b (5-HT2b) receptor Homo sapiens Ki = 119.0 nM PMID[36001775]
NPT290 Individual protein Serotonin 2a (5-HT2a) receptor Homo sapiens Ki = 966.0 nM PMID[36001775]
NPT292 Individual protein Serotonin 2c (5-HT2c) receptor Homo sapiens Ki = 328.0 nM PMID[36001775]
NPT4163 Individual protein Protein tyrosine phosphatase receptor type C-associated protein Homo sapiens IC50 = 88000.0 nM DOI[10.1016/0960-894X(95)00250-W]
NPT92 Individual protein Serotonin 1a (5-HT1a) receptor Homo sapiens Ki = 171.0 nM PMID[25695425]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1076 Cell line B-cells n.a. IC50 > 100000.0 nM PMID[17081761]
NPT1833 Organism Human coxsackievirus B1 Human coxsackievirus B1 IC50 = 21000.0 nM PMID[18590964]
NPT28438 Unchecked Unchecked n.a. Ratio Ki = 0.4 n.a. PMID[36001775]
NPT28438 Unchecked Unchecked n.a. Ratio Ki = 8.1 n.a. PMID[36001775]
NPT1832 Organism Human rhinovirus 14 Human rhinovirus 14 CC50 = 182000.0 nM PMID[18590964]
NPT1 Others Radical scavenging activity n.a. Activity = 0.8 % PMID[18590964]
NPT1 Others Radical scavenging activity n.a. Activity = 1.2 % PMID[18590964]
NPT1 Others Radical scavenging activity n.a. Activity = 1.1 % PMID[18590964]
NPT1 Others Radical scavenging activity n.a. Activity = 1.3 % PMID[18590964]
NPT1 Others Radical scavenging activity n.a. Activity = 1.4 % PMID[18590964]
NPT1 Others Radical scavenging activity n.a. Activity = 1.6 % PMID[18590964]
NPT1831 Organism Human echovirus 13 Human echovirus 13 IC50 = 60000.0 nM PMID[18590964]
NPT1106 Organism Human poliovirus 1 Human poliovirus 1 IC50 = 60000.0 nM PMID[18590964]
NPT2 Others Unspecified n.a. IC50 > 100000.0 nM PMID[17081761]
NPT2 Others Unspecified n.a. Ratio CC50/IC50 = 1.9 n.a. PMID[18590964]
NPT2 Others Unspecified n.a. Ratio CC50/IC50 = 8.3 n.a. PMID[18590964]
NPT2 Others Unspecified n.a. Ratio CC50/IC50 = 5.5 n.a. PMID[18590964]
NPT2 Others Unspecified n.a. IC50 = 96900.0 nM PMID[25277281]
NPT2 Others Unspecified n.a. Ratio Ki = 4.0 n.a. PMID[25695425]
NPT2 Others Unspecified n.a. Ratio Ki = 22.0 n.a. PMID[25695425]
NPT22130 Selectivity group Serotonin 2 receptors; 5-HT2a & 5-HT2c Homo sapiens Ratio Ki = 2.9 n.a. PMID[36001775]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 50.0 % PMID[17228858]





 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 NPC99659 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
1.0 High Similarity NPC325871
0.8182 Intermediate Similarity NPC63997
0.8182 Intermediate Similarity NPC16805
0.8182 Intermediate Similarity NPC167546
0.7368 Intermediate Similarity NPC136508
0.7143 Intermediate Similarity NPC326316
0.7143 Intermediate Similarity NPC81733
0.7069 Intermediate Similarity NPC253043
0.678 Remote Similarity NPC239775
0.6618 Remote Similarity NPC606311
0.619 Remote Similarity NPC266753
0.619 Remote Similarity NPC160298
0.6154 Remote Similarity NPC229166
0.6129 Remote Similarity NPC205421
0.6129 Remote Similarity NPC474931
0.6129 Remote Similarity NPC607722
0.5938 Remote Similarity NPC19520
0.5909 Remote Similarity NPC128560
0.5873 Remote Similarity NPC247389
0.5846 Remote Similarity NPC199465
0.5625 Remote Similarity NPC306902
0.5625 Remote Similarity NPC232924
0.5616 Remote Similarity NPC112248
0.5484 Remote Similarity NPC13504
0.5469 Remote Similarity NPC117188
0.5469 Remote Similarity NPC145832
0.5455 Remote Similarity NPC219341
0.5455 Remote Similarity NPC476432
0.5455 Remote Similarity NPC24264
0.5325 Remote Similarity NPC47077
0.5323 Remote Similarity NPC470925
0.5312 Remote Similarity NPC212794
0.5312 Remote Similarity NPC606254
0.5294 Remote Similarity NPC298979
0.5294 Remote Similarity NPC320223
0.5294 Remote Similarity NPC600118
0.5294 Remote Similarity NPC610764
0.5231 Remote Similarity NPC600388
0.5224 Remote Similarity NPC226102
0.5143 Remote Similarity NPC114364

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC99659 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