Natural Product: NPC30991

Natural Product IDNPC30991
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 DBPLRLXFFUKDDB-JBLDHEPKSA-N
IUPAC Name n.a.
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier n.a.
PubChem CID n.a.
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001564] Bicyclic monoterpenoids

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 DBPLRLXFFUKDDB-JBLDHEPKSA-N
Standard InCHI InChI=1S/C12H20O/c1-8(13)10-7-9-5-6-12(10,4)11(9,2)3/h9-10H,5-7H2,1-4H3/t9-,10-,12+/m0/s1
SMILES CC(=O)[C@@H]1C[C@@H]2CC[C@@]1(C)C2(C)C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   180.15 Volume:   205.149
?
Van der Waals volume.
Dense:   0.878 LogP:   2.93
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.909
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.542
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   1.0 Rigid Bonds:   9.0
TPSA:   17.07
?
Topological Polar Surface Area.
 H-Bond Acceptor:   1.0
H-Bond Donor:   0.0 Rings:   2.0
Heavy Atoms:   1.0

MedChem Properties

QED Drug-Likeness Score:   0.606 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   4.346 Fsp3:   0.917
MCE-18:   39.13
?
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:   Accepted BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.138 Fluc inhibitor:   0.063
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.003
?
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:   0.916 Promiscuous compounds:   0.607

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.606 MDCK Permeability:   -4.562
Pgp-inhibitor:   0.81 Pgp-substrate:   0.406
PAMPA:   0.174
?
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):   0.01
20% Bioavailability (F20%):   0.237 30% Bioavailability (F30%):   0.141
50% Bioavailability (F50%):   0.726

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.624 MRP1:   0.907
Plasma Protein Binding (PPB):   74.881% Volume Distribution (VD):   0.365
Fu: 24.759%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.728
OATP1B3 inhibitor:   0.653 BCRP inhibitor:   0.206
BSEP inhibitor:   0.759

ADMET: Metabolism

CYP1A2-inhibitor:   0.664 CYP1A2-substrate:   0.542
CYP2C19-inhibitor:   1.0 CYP2C19-substrate:   0.753
CYP2C9-inhibitor:   0.734 CYP2C9-substrate:   0.037
CYP2D6-inhibitor:   0.631 CYP2D6-substrate:   0.001
CYP3A4-inhibitor:   0.162 CYP3A4-substrate:   0.876
CYP2B6-substrate:   0.009 CYP2C8-inhibitor:   0.947
HLM stability:   0.846
?
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):  11.206 Half-life (T1/2):  0.651

ADMET: Toxicity

hERG Blockers:  0.085 hERG Blockers (10um):  0.336
Human Hepatotoxicity (H-HT):  0.572 Drug-induced Liver Injury (DILI):  0.524
AMES Toxicity:  0.5 Rat Oral Acute Toxicity:  0.455
Maximum Recommended Daily Dose:  0.397 Skin Sensitization:  0.736
Carcinogencity:  0.686 Eye Corrosion:  0.878
Eye Irritation:  0.99 Respiratory Toxicity:  0.771
Drug-induced Neurotoxicity:  0.456 Ototoxicity:  0.27
Hematotoxicity:  0.536 Drug-induced Nephrotoxicity:  0.521
Genotoxicity:  0.344 RPMI-8226 Immunitoxicity:  0.049
A549 Cytotoxicity:  0.131 Hek293 Cytotoxicity:  0.165
BCF:   2.042
?
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:   3.599
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.503
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.127
?
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
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jep.2005.01.054]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. root n.a. DOI[10.1016/S0031-9422(01)00459-9]
NPO27847 Suillus granulatus Species Suillaceae Eukaryota n.a. n.a. n.a. PMID[11575963]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. stem n.a. PMID[12770595]
NPO27847 Suillus granulatus Species Suillaceae Eukaryota n.a. n.a. n.a. PMID[1294697]
NPO27878 Viola hondoensis Species Violaceae Eukaryota n.a. whole plant n.a. PMID[15356999]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1800637]
NPO20443 Cratoxylum pruniflorum Species Hypericaceae Eukaryota roots n.a. n.a. PMID[24940955]
NPO27847 Suillus granulatus Species Suillaceae Eukaryota n.a. n.a. n.a. PMID[2607355]
NPO27847 Suillus granulatus Species Suillaceae Eukaryota n.a. n.a. n.a. PMID[2809609]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota Seeds n.a. n.a. PMID[28134521]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[31181920]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[31418264]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[32415726]
NPO27689 Mentha pulegium Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[33502110]
NPO27689 Mentha pulegium Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[34328036]
NPO27689 Mentha pulegium Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[37084277]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[37667613]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[37917799]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[38005226]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[38067590]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[38754641]
NPO27689 Mentha pulegium Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[38987699]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[39588261]
NPO27689 Mentha pulegium Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[39633960]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8158155]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8277307]
NPO20443 Cratoxylum pruniflorum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28006 Pinus pumila Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28049 Piper callosum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28174 Poterium sanguisorba Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16983 Persea obovatifolia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28191 Hardwickia pinnata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17152 Pittocaulon bombycophole Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27532 Lamprolobium fruticosum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28124 Tamarix gallica Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20121 Afraegle paniculata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27480 Pinna muricata Species Pinnidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28305 Daphnandra johnsonii Species Atherospermataceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28534 Athrixia elata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27894 Rubus pungens Species Rosaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4094 Aspergillus ruber Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28262 Marasmius graminum Species Marasmiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28512 Astragalus glycyphyllos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27681 Mikania grazielae Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27861 Laggera aurita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28074 Dianella revoluta Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27689 Mentha pulegium Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27847 Suillus granulatus Species Suillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20443 Cratoxylum pruniflorum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota Stem Bark n.a. n.a. Database[FooDB]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28124 Tamarix gallica Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27689 Mentha pulegium Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14888 Pelargonium x hortorum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28433 Russula queletii Species Russulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28124 Tamarix gallica Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27689 Mentha pulegium Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4266 Botryotrichum murorum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27861 Laggera aurita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28174 Poterium sanguisorba Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27480 Pinna muricata Species Pinnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28499 Aethalium septicum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO20121 Afraegle paniculata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28074 Dianella revoluta Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27220 Centaurea cheiranthifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27681 Mikania grazielae Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28330 Colchicum arenarium Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23272 Cassinia subtropica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28321 Cortinellus berkeleyanus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO28168 Armina maculata Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27334 Siphula roccellaeformis Species Icmadophilaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9367 Jacobaea argunensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28208 Salvia dichroa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28191 Hardwickia pinnata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14888 Pelargonium x hortorum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4094 Aspergillus ruber Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28555 Adina trichotoma Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28305 Daphnandra johnsonii Species Atherospermataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28061 Gyrothyra underwoodiana Species Gyrothyraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27318 Sideritis lanata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20443 Cratoxylum pruniflorum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28124 Tamarix gallica Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16983 Persea obovatifolia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27350 Scytalidium uredinicola Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28006 Pinus pumila Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27847 Suillus granulatus Species Suillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28345 Cladanthus arabicus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28262 Marasmius graminum Species Marasmiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28253 Ceratiomyxa fruticulosa Species Ceratiomyxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27878 Viola hondoensis Species Violaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28512 Astragalus glycyphyllos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27532 Lamprolobium fruticosum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28433 Russula queletii Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27894 Rubus pungens Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28534 Athrixia elata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28049 Piper callosum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17152 Pittocaulon bombycophole Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16927 Erodendrum neriifolium n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO28568 Hippeastrum aulicum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27689 Mentha pulegium Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15295 Polyachyrus sphaerocephalus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28139 Umbilicaria pustulata Species Umbilicariaceae 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

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 NPC30991 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
0.5909 Remote Similarity NPC131981
0.5909 Remote Similarity NPC173996
0.5909 Remote Similarity NPC40249

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC30991 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
0.5909 Remote Similarity NPD343 Approved
0.5909 Remote Similarity NPD344 Approved
0.5909 Remote Similarity NPD345 Phase 4

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