Natural Product: NPC78363

Natural Product IDNPC78363
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Plantasioside
IUPAC Name [(2S,4aR,6R,7S,8S,8aR)-2-(3,4-dihydroxyphenyl)-7,8-dihydroxy-3,4a,6,7,8,8a-hexahydro-2H-pyrano[2,3-b][1,4]dioxin-6-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms Plantasioside
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL228185
PubChem CID 44423103
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives
          • [CHEMONTID:0000059] Coumaric acids and derivatives

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 PAPHRQZMDUSBBD-CILOSVJESA-N
Standard InCHI InChI=1S/C23H24O11/c24-13-4-1-11(7-15(13)26)2-6-19(28)31-10-18-20(29)21(30)22-23(34-18)32-9-17(33-22)12-3-5-14(25)16(27)8-12/h1-8,17-18,20-27,29-30H,9-10H2/b6-2+/t17-,18-,20-,21+,22-,23-/m1/s1
SMILES c1cc(c(cc1/C=C/C(=O)OC[C@@H]1[C@H]([C@@H]([C@@H]2[C@H](OC[C@H](c3ccc(c(c3)O)O)O2)O1)O)O)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   476.13 Volume:   447.739
?
Van der Waals volume.
Dense:   1.063 LogP:   0.849
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.151
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.876
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   6.0 Rigid Bonds:   25.0
TPSA:   175.37
?
Topological Polar Surface Area.
 H-Bond Acceptor:   11.0
H-Bond Donor:   6.0 Rings:   4.0
Heavy Atoms:   11.0

MedChem Properties

QED Drug-Likeness Score:   0.203 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   4.302 Fsp3:   0.348
MCE-18:   86.29
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Accepted
Pfizer Rule:   Rejected GSK Rule:   Accepted
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   1 PAINS Alert:   1
Colloidal aggregators:   0.755 Fluc inhibitor:   0.986
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.076
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.589
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.411 Promiscuous compounds:   0.447

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -6.243 MDCK Permeability:   -5.29
Pgp-inhibitor:   0.0 Pgp-substrate:   0.054
PAMPA:   0.943
?
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):   0.124
20% Bioavailability (F20%):   0.998 30% Bioavailability (F30%):   0.999
50% Bioavailability (F50%):   1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.002 MRP1:   0.054
Plasma Protein Binding (PPB):   73.078% Volume Distribution (VD):   -0.233
Fu: 22.821%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.999
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.018
BSEP inhibitor:   0.006

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.0 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   0.0 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.001 CYP2D6-substrate:   0.023
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.999
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   0.762
?
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):  7.785 Half-life (T1/2):  2.326

ADMET: Toxicity

hERG Blockers:  0.04 hERG Blockers (10um):  0.596
Human Hepatotoxicity (H-HT):  0.704 Drug-induced Liver Injury (DILI):  0.971
AMES Toxicity:  0.934 Rat Oral Acute Toxicity:  0.107
Maximum Recommended Daily Dose:  0.442 Skin Sensitization:  1.0
Carcinogencity:  0.106 Eye Corrosion:  0.002
Eye Irritation:  0.965 Respiratory Toxicity:  0.036
Drug-induced Neurotoxicity:  0.009 Ototoxicity:  0.827
Hematotoxicity:  0.033 Drug-induced Nephrotoxicity:  0.191
Genotoxicity:  0.99 RPMI-8226 Immunitoxicity:  0.031
A549 Cytotoxicity:  0.955 Hek293 Cytotoxicity:  0.282
BCF:   0.823
?
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:   3.54
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.881
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.593
?
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
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[11858748]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[1367520]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15974609]
NPO30984 Fraxinus sieboldiana Species Oleaceae Eukaryota stem bark n.a. n.a. PMID[17461599]
NPO13010 Allium stipitatum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[19093848]
NPO13010 Allium stipitatum Species Amaryllidaceae Eukaryota n.a. bulb n.a. PMID[19093848]
NPO30984 Fraxinus sieboldiana Species Oleaceae Eukaryota n.a. stem n.a. PMID[20961093]
NPO30984 Fraxinus sieboldiana Species Oleaceae Eukaryota Stem bark Lu Mountain, Jiangxi Province, China 2004-AUG PMID[20961093]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. mycelium n.a. PMID[21381678]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21667925]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22118684]
NPO27031 Methanosarcina barkeri Species Methanosarcinaceae Archaea n.a. n.a. n.a. PMID[24669201]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[24840014]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[2488968]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. seed n.a. PMID[2610694]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26692349]
NPO30984 Fraxinus sieboldiana Species Oleaceae Eukaryota n.a. n.a. n.a. PMID[26697686]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota Stems n.a. n.a. PMID[31180680]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[33089690]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[8626236]
NPO5995 Spartium junceum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14327 Scabiosa comosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22203 Tapinella panuoides Species Tapinellaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15404 Streptomyces erythrochromogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO15898 Streptomyces noursei Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO15108 Angiopteris evecta Species Marattiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14454 Plectranthus lanuginosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27031 Methanosarcina barkeri Species Methanosarcinaceae Archaea n.a. n.a. n.a. Database[COCONUT]
NPO30984 Fraxinus sieboldiana Species Oleaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14965 Lepidophorum repandum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15621 Lethasterias fusca Species Asteriidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11584 Artemisia argentea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12480 Brodiaea californica Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9917 Plagiomnium cuspidatum Species Mniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28240 Notholaena lemmonii Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14614 Kopsia longiflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5137 Myristica malabarica Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13743 Populus yunnanensis Species Salicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15087 Alstonia pittieri Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16161 Stephania aculeata Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12777 Laurencia pacifica Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1124 Scapania aequiloba Species Scapaniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5995 Spartium junceum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14327 Scabiosa comosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5137 Myristica malabarica Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14614 Kopsia longiflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14614 Kopsia longiflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14327 Scabiosa comosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5995 Spartium junceum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5137 Myristica malabarica Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9917 Plagiomnium cuspidatum Species Mniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14327 Scabiosa comosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5995 Spartium junceum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13477 Cyberlindnera jadinii Species Phaffomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22203 Tapinella panuoides Species Tapinellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13225 Spergula japonica Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO255 Solanum pseudopersicum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16161 Stephania aculeata Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15087 Alstonia pittieri Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28240 Notholaena lemmonii Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13010 Allium stipitatum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14614 Kopsia longiflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14454 Plectranthus lanuginosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11584 Artemisia argentea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2667 Acacia lasiopetala Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27134 Euphrasia rubra Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8556 Eucalyptus kitsoniana Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5995 Spartium junceum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10527 Cyathula tomentosa Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26381 Bombus pascuorum Species Apidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15513 Pseudocyphellaria rubella Species Lobariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15806 Rhododendron campylocarpum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1777 Toddalia aculeata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9299.3 Hordeum vulgare var. distichon Varieties Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15718 Lindera sericea Species Tineidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1124 Scapania aequiloba Species Scapaniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5137 Myristica malabarica Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15108 Angiopteris evecta Species Marattiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13460 Asphodeline damascena Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16076 Penicillium chrysogenum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9917 Plagiomnium cuspidatum Species Mniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27031 Methanosarcina barkeri Species Methanosarcinaceae Archaea n.a. n.a. n.a. Database[UNPD]
NPO15898 Streptomyces noursei Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO22101 Himantoglossum hircinum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15404 Streptomyces erythrochromogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26951 Gymnopus androsaceus Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13743 Populus yunnanensis Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11243 Exochorda giraldii Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14327 Scabiosa comosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12777 Laurencia pacifica Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12480 Brodiaea californica Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21851 Chaetomella raphigera Species Chaetomellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14965 Lepidophorum repandum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29322 Rhodanthe maryonii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15621 Lethasterias fusca Species Asteriidae 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
NPT180 Cell line HCT-8 Homo sapiens IC50 = 3400.0 nM PMID[17461599]

In vivo activity

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





 Experimental ADME

Experiment Model Experiment Tissue ADME Type ADME Relation ADME Value ADME Unit Reference





 Experimental Toxicity

Quantitative toxicity

Experiment Model Experiment Organism Toxicity Type Toxicity Relation Toxicity Value Toxicity Unit Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption
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 NPC78363 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
0.65 Remote Similarity NPC265648
0.5732 Remote Similarity NPC321638
0.5541 Remote Similarity NPC470572
0.5429 Remote Similarity NPC476873
0.5395 Remote Similarity NPC229784
0.5366 Remote Similarity NPC471883
0.5325 Remote Similarity NPC287597
0.5233 Remote Similarity NPC222433
0.519 Remote Similarity NPC157898
0.5062 Remote Similarity NPC219677

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC78363 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