Natural Product: NPC285371

Natural Product IDNPC285371
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Aristolone
IUPAC Name (1aR,7R,7aR,7bS)-1,1,7,7a-tetramethyl-1a,4,5,6,7,7b-hexahydrocyclopropa[a]naphthalen-2-one
Synonyms Aristolone
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL512374
PubChem CID 165536
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0003565] Aristolane sesquiterpenoids

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 UGVIZCBJCSXBCJ-JWFUOXDNSA-N
Standard InCHI InChI=1S/C15H22O/c1-9-6-5-7-10-8-11(16)12-13(14(12,2)3)15(9,10)4/h8-9,12-13H,5-7H2,1-4H3/t9-,12-,13+,15+/m1/s1
SMILES O=C1C=C2CCC[C@H]([C@@]2([C@H]2[C@@H]1C2(C)C)C)C

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   218.17 Volume:   245.844
?
Van der Waals volume.
Dense:   0.887 LogP:   3.672
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.372
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.673
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   0.0 Rigid Bonds:   14.0
TPSA:   17.07
?
Topological Polar Surface Area.
 H-Bond Acceptor:   1.0
H-Bond Donor:   0.0 Rings:   3.0
Heavy Atoms:   1.0

MedChem Properties

QED Drug-Likeness Score:   0.607 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   4.193 Fsp3:   0.8
MCE-18:   51.852
?
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:   Rejected
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.068 Fluc inhibitor:   0.094
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.1
?
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:   0.694 Promiscuous compounds:   0.33

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.817 MDCK Permeability:   -4.581
Pgp-inhibitor:   0.987 Pgp-substrate:   0.018
PAMPA:   0.037
?
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):   0.006
20% Bioavailability (F20%):   0.159 30% Bioavailability (F30%):   0.089
50% Bioavailability (F50%):   0.389

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.603 MRP1:   0.908
Plasma Protein Binding (PPB):   82.436% Volume Distribution (VD):   -0.139
Fu: 18.601%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.978
OATP1B3 inhibitor:   0.792 BCRP inhibitor:   0.051
BSEP inhibitor:   0.995

ADMET: Metabolism

CYP1A2-inhibitor:   0.059 CYP1A2-substrate:   0.994
CYP2C19-inhibitor:   0.935 CYP2C19-substrate:   0.753
CYP2C9-inhibitor:   0.136 CYP2C9-substrate:   0.237
CYP2D6-inhibitor:   0.43 CYP2D6-substrate:   0.189
CYP3A4-inhibitor:   0.733 CYP3A4-substrate:   0.99
CYP2B6-substrate:   0.779 CYP2C8-inhibitor:   0.988
HLM stability:   0.901
?
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):  10.647 Half-life (T1/2):  0.773

ADMET: Toxicity

hERG Blockers:  0.05 hERG Blockers (10um):  0.344
Human Hepatotoxicity (H-HT):  0.568 Drug-induced Liver Injury (DILI):  0.557
AMES Toxicity:  0.413 Rat Oral Acute Toxicity:  0.318
Maximum Recommended Daily Dose:  0.537 Skin Sensitization:  0.77
Carcinogencity:  0.794 Eye Corrosion:  0.672
Eye Irritation:  0.968 Respiratory Toxicity:  0.74
Drug-induced Neurotoxicity:  0.485 Ototoxicity:  0.291
Hematotoxicity:  0.536 Drug-induced Nephrotoxicity:  0.476
Genotoxicity:  0.376 RPMI-8226 Immunitoxicity:  0.065
A549 Cytotoxicity:  0.053 Hek293 Cytotoxicity:  0.131
BCF:   2.475
?
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:   4.061
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.95
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.747
?
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
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. DOI[10.1016/0045-6535(91)90110-Y]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.abb.2017.09.009]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2004.07.004]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2005.08.001]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. retail stores, supermarkets and market stalls in Forssa and in the Helsinki area 2003–2005 DOI[10.1016/j.jfca.2006.05.007]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(99)00119-3]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(01)90945-1]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0885-5765(05)80069-4]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. 1996-Sep PMID[10352947]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15877880]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[17703773]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. Northeastern Regional Plant Introduction Station at Geneva 1966, 1967, and 1968 crop seasons PMID[18460139]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. PMID[20476749]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. rhizome n.a. PMID[21563811]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21800857]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. root n.a. PMID[21800857]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. exocarp n.a. PMID[21800857]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota n.a. rhizome n.a. PMID[21936523]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota Rhizomes n.a. n.a. PMID[21936523]
NPO25682 Acorus calamus Species Acoraceae Eukaryota rhizomes n.a. n.a. PMID[22671987]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota rhizomes n.a. n.a. PMID[22951040]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. n.a. n.a. PMID[23373216]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. rhizome n.a. PMID[23713285]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[24704449]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota rhizomes n.a. n.a. PMID[26296476]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. PMID[26305406]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[26967731]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[2831703]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota Rhizomes n.a. n.a. PMID[29116780]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. PMID[32807141]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[35143705]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. n.a. n.a. PMID[35872238]
NPO48641 Jambosa caryophyllus n.a. n.a. n.a. n.a. n.a. n.a. PMID[36310621]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[36378844]
NPO57639 Cuscuta campestris Species Convolvulaceae Eukaryota n.a. n.a. n.a. PMID[37183783]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[38139796]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[38498554]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. PMID[38821245]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[38830452]
NPO1942 Piper philippinum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[39771253]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[6821187]
NPO33499 porella cordeana Species Porellaceae Eukaryota n.a. n.a. n.a. PMID[8350093]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1942 Piper philippinum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6444 Humulus scandens Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1821 Kopsia albiflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2741 Ribes sanguineum Species Grossulariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5497 Stachys chinensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14809 Talaromyces avellaneus Species Trichocomaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14108 Nardostachys jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Tissue Culture n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Roots n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14108 Nardostachys jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO319 Citrus limon Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14108 Nardostachys jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14108 Nardostachys jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14108 Nardostachys jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16755 Saposhnikovia divaricata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6444 Humulus scandens Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1821 Kopsia albiflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14809 Talaromyces avellaneus Species Trichocomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5497 Stachys chinensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14108 Nardostachys jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2741 Ribes sanguineum Species Grossulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1942 Piper philippinum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8666 Acorus tatarinowii Species Acoraceae 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
NPO16755 Saposhnikovia divaricata n.a. Roots 177.05455, 121.06506, 91.05492 n.a. n.a. % PMID[38830452]
NPO16755 Saposhnikovia divaricata n.a. Roots 0.10 n.a. n.a. % PMID[38830452]
NPO1942 Piper philippinum Oil Aerial parts 0.127 ± 0.009 n.a. n.a. % PMID[39771253]
NPO319 Citrus limon Oil Leaves 0.81 n.a. n.a. % PMID[36378844]
NPO48641 Jambosa caryophyllus Oil n.a. 3.33 n.a. n.a. % PMID[36310621]
NPO57639 Cuscuta campestris Oil Stems 0.94±0.04 n.a. n.a. % PMID[37183783]
NPO8666 Acorus tatarinowii Oil n.a. 8.96±2.95 n.a. n.a. % PMID[32807141]
NPO8666 Acorus tatarinowii Oil n.a. 14.15±2.37 n.a. n.a. % PMID[32807141]
NPO8666 Acorus tatarinowii Oil n.a. 2.90±0.63 n.a. n.a. % PMID[32807141]
NPO8666 Acorus tatarinowii Oil n.a. 5.31±1.04 n.a. n.a. % PMID[32807141]
NPO8666 Acorus tatarinowii Oil n.a. 3.10±1.12 n.a. n.a. % PMID[32807141]

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
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IC12 = 390.0 ug ml-1 PMID[8350093]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IC12 > 1000.0 ug ml-1 PMID[8350093]

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 NPC285371 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
NPC

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC285371 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