Natural Product: NPC46674

Natural Product IDNPC46674
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 BBPXZLJCPUPNGH-CMKODMSKSA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID 443470
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids

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 BBPXZLJCPUPNGH-CMKODMSKSA-N
Standard InCHI InChI=1S/C20H32/c1-14(2)15-7-9-17-16(13-15)8-10-18-19(3,4)11-6-12-20(17,18)5/h8,13-14,17-18H,6-7,9-12H2,1-5H3/t17-,18-,20+/m0/s1
SMILES CC(C)C1=CC2=CC[C@H]3C(C)(C)CCC[C@]3(C)[C@H]2CC1

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   272.25 Volume:   323.534
?
Van der Waals volume.
Dense:   0.841 LogP:   6.131
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   4.336
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -6.67
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   1.0 Rigid Bonds:   16.0
TPSA:   0.0
?
Topological Polar Surface Area.
 H-Bond Acceptor:   0.0
H-Bond Donor:   0.0 Rings:   3.0
Heavy Atoms:   0.0

MedChem Properties

QED Drug-Likeness Score:   0.537 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.997 Fsp3:   0.8
MCE-18:   51.111
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Accepted GSK Rule:   Accepted
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.6 Fluc inhibitor:   0.605
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.007
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.0
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.932 Promiscuous compounds:   0.109

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.468 MDCK Permeability:   -4.784
Pgp-inhibitor:   0.954 Pgp-substrate:   0.002
PAMPA:   0.007
?
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):   0.0
20% Bioavailability (F20%):   0.077 30% Bioavailability (F30%):   0.188
50% Bioavailability (F50%):   0.913

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.255 MRP1:   0.799
Plasma Protein Binding (PPB):   98.138% Volume Distribution (VD):   0.554
Fu: 2.172%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.999
OATP1B3 inhibitor:   0.99 BCRP inhibitor:   0.638
BSEP inhibitor:   0.998

ADMET: Metabolism

CYP1A2-inhibitor:   0.714 CYP1A2-substrate:   0.956
CYP2C19-inhibitor:   1.0 CYP2C19-substrate:   0.945
CYP2C9-inhibitor:   0.111 CYP2C9-substrate:   0.692
CYP2D6-inhibitor:   0.053 CYP2D6-substrate:   0.993
CYP3A4-inhibitor:   1.0 CYP3A4-substrate:   1.0
CYP2B6-substrate:   0.997 CYP2C8-inhibitor:   1.0
HLM stability:   0.994
?
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):  9.663 Half-life (T1/2):  0.214

ADMET: Toxicity

hERG Blockers:  0.148 hERG Blockers (10um):  0.563
Human Hepatotoxicity (H-HT):  0.571 Drug-induced Liver Injury (DILI):  0.251
AMES Toxicity:  0.155 Rat Oral Acute Toxicity:  0.226
Maximum Recommended Daily Dose:  0.644 Skin Sensitization:  0.902
Carcinogencity:  0.783 Eye Corrosion:  0.811
Eye Irritation:  0.98 Respiratory Toxicity:  0.797
Drug-induced Neurotoxicity:  0.359 Ototoxicity:  0.364
Hematotoxicity:  0.443 Drug-induced Nephrotoxicity:  0.554
Genotoxicity:  0.054 RPMI-8226 Immunitoxicity:  0.055
A549 Cytotoxicity:  0.123 Hek293 Cytotoxicity:  0.443
BCF:   3.778
?
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:   5.071
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.81
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   6.437
?
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
NPO25880 Sarcococca coriacea Species Buxaceae Eukaryota leaves Nepalese n.a. PMID[11421762]
NPO9829 Arnica chamissonis Species Asteraceae Eukaryota n.a. rhizome n.a. PMID[16644542]
NPO9829 Arnica chamissonis Species Asteraceae Eukaryota n.a. root n.a. PMID[16644542]
NPO13135 Campylotropis hirtella Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[19481938]
NPO14077 Chamaecyparis lawsoniana Species Cupressaceae Eukaryota n.a. stem n.a. PMID[23157017]
NPO14077 Chamaecyparis lawsoniana Species Cupressaceae Eukaryota n.a. leaf n.a. PMID[23157017]
NPO9829 Arnica chamissonis Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[28294615]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[31291099]
NPO18735 Pinus mugo Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[31475763]
NPO11882 Cedrus libani Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[32092041]
NPO45866 Taiwania flousiana Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[32093424]
NPO46696 Araucaria brasiliensis Species Araucariaceae Eukaryota n.a. n.a. n.a. PMID[35744919]
NPO14077 Chamaecyparis lawsoniana Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[37447036]
NPO45102 Cupressus arizonica Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[37482262]
NPO43369 Cupressus torulosa Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[38157454]
NPO14077 Chamaecyparis lawsoniana Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[38794396]
NPO19162 Tsuga heterophylla Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[38794396]
NPO1257 Distephanus angulifolius Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10922 Pentaclethra macrophylla Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18735 Pinus mugo Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7773 Crinum moorei Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11882 Cedrus libani Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9704 Sonneratia caseolaris Species Lythraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO45102 Cupressus arizonica Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9829 Arnica chamissonis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19162 Tsuga heterophylla Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25880 Sarcococca coriacea Species Buxaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9319 Pterocaulon virgatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO43369 Cupressus torulosa Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14077 Chamaecyparis lawsoniana Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6851 Aplysilla pallida Species Darwinellidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20800 Pholiota nameko Species Strophariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12205 Eucalyptus apodophylla Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7773 Crinum moorei Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19162 Tsuga heterophylla Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13135 Campylotropis hirtella Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6731 Ononis spinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24299 Litsea laurifolia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6731 Ononis spinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7773 Crinum moorei Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24299 Litsea laurifolia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19162 Tsuga heterophylla Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13135 Campylotropis hirtella Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6731 Ononis spinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1815 Breonia chinensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9704 Sonneratia caseolaris Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23384 Rhodiola semenovii Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10638 Plectranthus myrianthus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3873 Crotalaria candicans Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11843 Stephania zippeliana Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12565 Hypericum polyanthemum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11190 Veronica polita Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25880 Sarcococca coriacea Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10922 Pentaclethra macrophylla Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6851 Aplysilla pallida Species Darwinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18735 Pinus mugo Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5043 Eria japonica Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8934 Gypsophila perfoliata Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9532 Vernonia cistifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13135 Campylotropis hirtella Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6289 Ceropegia dichotoma Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5456 Juniperus drupacea Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7773 Crinum moorei Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1257 Distephanus angulifolius Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9319 Pterocaulon virgatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21720 Talaromyces variabilis Species Trichocomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7822.1 Eucalyptus globulus subsp. bicostata Subspecies Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10310 Cutaneotrichosporon cutaneum Species Trichosporonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12091 Martensia denticulata Species Delesseriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11882 Cedrus libani Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO526 Salvia sessei Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6731 Ononis spinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12205 Eucalyptus apodophylla Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11576 Glycosmis macrophylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24299 Litsea laurifolia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20800 Pholiota nameko Species Strophariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10605 Tristania conferta Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22691 Mentha cardiaca Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6478 Tubifera ferruginosa Species Reticulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14077 Chamaecyparis lawsoniana Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24479 Phaseolus atropurpureus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17593.1 Pinus sylvestris var. hamata Varieties Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25483 Croton cortesianus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24568 Spongia zimocca Species Spongiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26279 Premna schimperi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9829 Arnica chamissonis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26582 Erigeron sumatrensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26464 Macaranga indica Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26799 Vitis heyneana Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25421 Stemodia viscosa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19162 Tsuga heterophylla Species Pinaceae 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
NPO11882 Cedrus libani Oil n.a. 3.4±0.0 n.a. n.a. % PMID[32092041]
NPO11882 Cedrus libani Oil n.a. 1.9±0.1 n.a. n.a. % PMID[32092041]
NPO11882 Cedrus libani Oil n.a. 7.5±0.3 n.a. n.a. % PMID[32092041]
NPO11882 Cedrus libani Oil n.a. 3.2±0.1 n.a. n.a. % PMID[32092041]
NPO11882 Cedrus libani Oil n.a. 4.7±0.8 n.a. n.a. % PMID[32092041]
NPO14077 Chamaecyparis lawsoniana Oil Leaves 0.07 n.a. n.a. % PMID[37447036]
NPO18735 Pinus mugo Oil n.a. 0.2 n.a. n.a. % PMID[31475763]
NPO18735 Pinus mugo Oil n.a. 0.1 n.a. n.a. % PMID[31475763]
NPO18735 Pinus mugo Oil n.a. 0.6 n.a. n.a. % PMID[31475763]
NPO19162 Tsuga heterophylla Oil Leaves 0.1 n.a. n.a. % PMID[38794396]
NPO43369 Cupressus torulosa Oil n.a. 0.82±0.2 n.a. n.a. % PMID[38157454]
NPO45102 Cupressus arizonica Oil n.a. 0.11 n.a. n.a. % PMID[37482262]
NPO45866 Taiwania flousiana Oil n.a. 0.04 n.a. n.a. % PMID[32093424]
NPO46696 Araucaria brasiliensis Oil n.a. 0.14 ± 0.02 n.a. n.a. % PMID[35744919]
NPO46696 Araucaria brasiliensis Oil n.a. 0.14 ± 0.01 n.a. n.a. % PMID[35744919]

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

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 NPC46674 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
0.7381 Intermediate Similarity NPC216460
0.7209 Intermediate Similarity NPC193770
0.6596 Remote Similarity NPC899
0.6327 Remote Similarity NPC4827
0.5652 Remote Similarity NPC604452
0.5517 Remote Similarity NPC15910
0.5294 Remote Similarity NPC309399
0.5208 Remote Similarity NPC54407
0.52 Remote Similarity NPC259156

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC46674 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