Natural Product: NPC227925

Natural Product IDNPC227925
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 (8Ar)-8A-Hydroxy-3,3,6,6,8,8-Hexamethyl-1,2-Benzodioxine-5,7-Dione
IUPAC Name (8aR)-8a-hydroxy-3,3,6,6,8,8-hexamethyl-1,2-benzodioxine-5,7-dione
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL34459
PubChem CID 44281346
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000129] Alcohols and polyols
          • [CHEMONTID:0001292] Cyclic alcohols 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 UBYZFUSXTLJWFM-AWEZNQCLSA-N
Standard InCHI InChI=1S/C14H20O5/c1-11(2)7-8-9(15)12(3,4)10(16)13(5,6)14(8,17)19-18-11/h7,17H,1-6H3/t14-/m0/s1
SMILES CC1(C)C=C2C(=O)C(C)(C)C(=O)C(C)(C)[C@@]2(O)OO1

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   268.13 Volume:   269.629
?
Van der Waals volume.
Dense:   0.994 LogP:   1.573
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   1.579
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.729
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   0.0 Rigid Bonds:   13.0
TPSA:   72.83
?
Topological Polar Surface Area.
 H-Bond Acceptor:   5.0
H-Bond Donor:   1.0 Rings:   2.0
Heavy Atoms:   5.0

MedChem Properties

QED Drug-Likeness Score:   0.533 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   4.251 Fsp3:   0.714
MCE-18:   49.0
?
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:   1
Chelating Alert:   1 PAINS Alert:   0
Colloidal aggregators:   0.007 Fluc inhibitor:   0.0
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.091
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.288
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.784 Promiscuous compounds:   0.401

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.567 MDCK Permeability:   -4.63
Pgp-inhibitor:   0.739 Pgp-substrate:   0.173
PAMPA:   0.971
?
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):   0.045
20% Bioavailability (F20%):   0.02 30% Bioavailability (F30%):   0.075
50% Bioavailability (F50%):   0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.005 MRP1:   0.994
Plasma Protein Binding (PPB):   61.1% Volume Distribution (VD):   0.401
Fu: 32.572%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.982
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.555
BSEP inhibitor:   0.999

ADMET: Metabolism

CYP1A2-inhibitor:   0.999 CYP1A2-substrate:   0.039
CYP2C19-inhibitor:   0.015 CYP2C19-substrate:   0.037
CYP2C9-inhibitor:   0.0 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.964
CYP3A4-inhibitor:   1.0 CYP3A4-substrate:   0.526
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.983
HLM stability:   0.629
?
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):  10.568 Half-life (T1/2):  0.647

ADMET: Toxicity

hERG Blockers:  0.101 hERG Blockers (10um):  0.45
Human Hepatotoxicity (H-HT):  0.429 Drug-induced Liver Injury (DILI):  0.575
AMES Toxicity:  0.742 Rat Oral Acute Toxicity:  0.676
Maximum Recommended Daily Dose:  0.865 Skin Sensitization:  0.98
Carcinogencity:  0.464 Eye Corrosion:  0.02
Eye Irritation:  0.601 Respiratory Toxicity:  0.285
Drug-induced Neurotoxicity:  0.416 Ototoxicity:  0.274
Hematotoxicity:  0.387 Drug-induced Nephrotoxicity:  0.275
Genotoxicity:  0.978 RPMI-8226 Immunitoxicity:  0.269
A549 Cytotoxicity:  0.011 Hek293 Cytotoxicity:  0.393
BCF:   0.425
?
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:   2.795
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.086
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.538
?
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
NPO29027 Khaya grandifoliola Species Meliaceae Eukaryota n.a. seed n.a. PMID[10661881]
NPO15077 Achyranthes bidentata Species Amaranthaceae Eukaryota n.a. n.a. n.a. PMID[11430011]
NPO12848 Carpinus cordata Species Betulaceae Eukaryota stems n.a. n.a. PMID[12350169]
NPO15915 Edgeworthia gardneri Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[15387673]
NPO13199 Syzygium jambos Species Myrtaceae Eukaryota n.a. whole plant n.a. PMID[28294414]
NPO16125 Micromonas pusilla Species Mamiellaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13199 Syzygium jambos Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15349 Acacia sparsiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15077 Achyranthes bidentata Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14936 Agave shawii Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15205 Alaria crispa Species Alariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9479 Ambrosia grayi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13139 Anatheca montagnei Species Solieriaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11808 Ania latifolia Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14807 Arenaria juncea Species Scolopacidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16642 Astrantia major Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11436 Baeomyces roseus Species Baeomycetaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5866 Bitis arietans Species Viperidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15697 Camellia sasanqua Species Theaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12848 Carpinus cordata Species Betulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26426.1 Cassia javanica subsp. nodosa Subspecies Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16884 Convallaria keiskei Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14463 Dirca occidentalis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15797 Drypetes littoralis Species Putranjivaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15915 Edgeworthia gardneri Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13442 Eucalyptus regnans Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12293 Euphorbia iberica Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24409 Evasterias troschelii Species Asteriidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5047 Evodiopanax innovans n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO820 Grindelia perennis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11002 Hopea jucunda Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29027 Khaya grandifoliola Species Meliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12490 Lecidea speirodes Species Lecideaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2038 Myrtus tomentosa Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14313 Pachybasium candidum n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO16718 Pinna nobilis Species Pinnidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16475 Plumbago pulchella Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2827 Plumeria alba Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16557 Polygala ruwenzoriensis Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8804 Raputia simulans n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO20219 Rhizobium etli Species Rhizobiaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO27733 Rosa hybrid cultivar Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16796 Rumex conglomeratus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4589 Sarcotragus spinosulus Species Irciniidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15588 Senecio desfontainei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11987 Silene inflata Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11994 Thesium humile Species Thesiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7987 Tilia vulgaris Species Malvaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16025 Werneria decora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13199 Syzygium jambos Species Myrtaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO13199 Syzygium jambos Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16884 Convallaria keiskei Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13199 Syzygium jambos Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7987 Tilia vulgaris Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16642 Astrantia major Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15077 Achyranthes bidentata Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26426.1 Cassia javanica subsp. nodosa Subspecies Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15077 Achyranthes bidentata Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16884 Convallaria keiskei Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16642 Astrantia major Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13199 Syzygium jambos Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7987 Tilia vulgaris Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15697 Camellia sasanqua Species Theaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7987 Tilia vulgaris Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15077 Achyranthes bidentata Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13199 Syzygium jambos Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16884 Convallaria keiskei Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15077 Achyranthes bidentata Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15915 Edgeworthia gardneri Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16125 Micromonas pusilla Species Mamiellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13139 Anatheca montagnei Species Solieriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11994 Thesium humile Species Thesiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14936 Agave shawii Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4589 Sarcotragus spinosulus Species Irciniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9479 Ambrosia grayi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15797 Drypetes littoralis Species Putranjivaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11002 Hopea jucunda Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11987 Silene inflata Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16718 Pinna nobilis Species Pinnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11436 Baeomyces roseus Species Baeomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16557 Polygala ruwenzoriensis Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15077 Achyranthes bidentata Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16796 Rumex conglomeratus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15588 Senecio desfontainei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16642 Astrantia major Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26426.1 Cassia javanica subsp. nodosa Subspecies Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14463 Dirca occidentalis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5866 Bitis arietans Species Viperidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27733 Rosa hybrid cultivar Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14313 Pachybasium candidum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO15205 Alaria crispa Species Alariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7987 Tilia vulgaris Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13199 Syzygium jambos Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11808 Ania latifolia Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12848 Carpinus cordata Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24409 Evasterias troschelii Species Asteriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14807 Arenaria juncea Species Scolopacidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8804 Raputia simulans n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16884 Convallaria keiskei Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16025 Werneria decora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16475 Plumbago pulchella Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12490 Lecidea speirodes Species Lecideaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15697 Camellia sasanqua Species Theaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5047 Evodiopanax innovans n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO15349 Acacia sparsiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12293 Euphorbia iberica Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13442 Eucalyptus regnans Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29027 Khaya grandifoliola Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2038 Myrtus tomentosa Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20219 Rhizobium etli Species Rhizobiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO820 Grindelia perennis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2827 Plumeria alba Species Apocynaceae 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
NPT920 Individual protein Alpha-synuclein Homo sapiens Activity n.a. n.a. n.a. PMID[37610242]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 36000.0 nM PMID[15006377]

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 NPC227925 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

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC227925 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

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