Natural Product: NPC16830

Natural Product IDNPC16830
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 5-[(3S,6S)-3-(1,3-Benzodioxol-5-Yl)-1,3,3A,4,6,6A-Hexahydrofuro[3,4-C]Furan-6-Yl]-1,3-Benzodioxole
IUPAC Name 5-[(3S,6S)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-1,3-benzodioxole
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL1708854
PubChem CID 25245913
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003686] Furanoid lignans

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 PEYUIKBAABKQKQ-XGMIPLPHSA-N
Standard InCHI InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13?,14?,19-,20-/m1/s1
SMILES c1cc2c(cc1[C@@H]1C3CO[C@H](c4ccc5c(c4)OCO5)C3CO1)OCO2

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   354.11 Volume:   340.06
?
Van der Waals volume.
Dense:   1.041 LogP:   2.262
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.488
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.004
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   2.0 Rigid Bonds:   29.0
TPSA:   55.38
?
Topological Polar Surface Area.
 H-Bond Acceptor:   6.0
H-Bond Donor:   0.0 Rings:   6.0
Heavy Atoms:   6.0

MedChem Properties

QED Drug-Likeness Score:   0.825 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.774 Fsp3:   0.4
MCE-18:   100.0
?
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:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.51 Fluc inhibitor:   0.866
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.047
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.051
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.291 Promiscuous compounds:   0.568

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.818 MDCK Permeability:   -4.662
Pgp-inhibitor:   0.238 Pgp-substrate:   0.003
PAMPA:   0.09
?
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%):   0.006 30% Bioavailability (F30%):   0.0
50% Bioavailability (F50%):   0.217

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.98 MRP1:   0.83
Plasma Protein Binding (PPB):   94.585% Volume Distribution (VD):   0.189
Fu: 7.879%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.338
OATP1B3 inhibitor:   0.393 BCRP inhibitor:   0.006
BSEP inhibitor:   1.0

ADMET: Metabolism

CYP1A2-inhibitor:   0.989 CYP1A2-substrate:   0.988
CYP2C19-inhibitor:   1.0 CYP2C19-substrate:   0.474
CYP2C9-inhibitor:   0.999 CYP2C9-substrate:   1.0
CYP2D6-inhibitor:   1.0 CYP2D6-substrate:   1.0
CYP3A4-inhibitor:   0.406 CYP3A4-substrate:   0.961
CYP2B6-substrate:   0.999 CYP2C8-inhibitor:   0.0
HLM stability:   0.587
?
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):  3.135 Half-life (T1/2):  1.229

ADMET: Toxicity

hERG Blockers:  0.237 hERG Blockers (10um):  0.466
Human Hepatotoxicity (H-HT):  0.757 Drug-induced Liver Injury (DILI):  0.962
AMES Toxicity:  0.847 Rat Oral Acute Toxicity:  0.512
Maximum Recommended Daily Dose:  0.674 Skin Sensitization:  0.289
Carcinogencity:  0.875 Eye Corrosion:  0.001
Eye Irritation:  0.679 Respiratory Toxicity:  0.473
Drug-induced Neurotoxicity:  0.647 Ototoxicity:  0.442
Hematotoxicity:  0.304 Drug-induced Nephrotoxicity:  0.307
Genotoxicity:  0.932 RPMI-8226 Immunitoxicity:  0.129
A549 Cytotoxicity:  0.162 Hek293 Cytotoxicity:  0.482
BCF:   1.968
?
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:   4.092
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   6.249
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   5.347
?
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
NPO10574 Machilus thunbergii Species Lauraceae Eukaryota n.a. bark n.a. PMID[11045899]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. seed n.a. PMID[11540412]
NPO31494 Acanthopanax senticosus n.a. n.a. n.a. n.a. leaf n.a. PMID[11816040]
NPO17651 Bridelia retusa Species Phyllanthaceae Eukaryota n.a. stem n.a. PMID[12560039]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. leaf n.a. PMID[15388977]
NPO8188 Hypoestes purpurea Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[15568798]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[16872768]
NPO31494 Acanthopanax senticosus n.a. n.a. n.a. n.a. n.a. n.a. PMID[17125224]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. leaf n.a. PMID[17125224]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. stem n.a. PMID[17202689]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota fruits n.a. n.a. PMID[17625893]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota Fruits n.a. n.a. PMID[18293924]
NPO9650 Zanthoxylum nitidum Species Rutaceae Eukaryota Stems; Barks n.a. n.a. PMID[18303853]
NPO9650 Zanthoxylum nitidum Species Rutaceae Eukaryota stem bark n.a. n.a. PMID[18303853]
NPO10574 Machilus thunbergii Species Lauraceae Eukaryota n.a. bark n.a. PMID[19555186]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. n.a. n.a. PMID[20192247]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. pericarp n.a. PMID[20628994]
NPO26237 Piper longum Species Piperaceae Eukaryota fruits n.a. n.a. PMID[20839888]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. fruit n.a. PMID[21319773]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota roots n.a. n.a. PMID[22381047]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota fruits n.a. n.a. PMID[22445674]
NPO30633 Acanthopanax sessiliflorus n.a. n.a. n.a. Fruits n.a. n.a. PMID[22691179]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[23434420]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota fruits n.a. n.a. PMID[23623680]
NPO4617 Tanacetum cinerariifolium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24253739]
NPO29744 Acanthopanax gracilistylus n.a. n.a. n.a. Root Bark n.a. n.a. PMID[25338180]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota fruits n.a. n.a. PMID[25735399]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota leaves n.a. n.a. PMID[27400231]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota Fruits n.a. n.a. PMID[28322565]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota Fruits n.a. n.a. PMID[28968119]
NPO31494 Acanthopanax senticosus n.a. n.a. n.a. Barks Iksan, Chunbuk, Korea n.a. PMID[3127544]
NPO8500 Acanthopanax gracilistylus Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[32319765]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[33588649]
NPO14951 Zanthoxylum acanthopodium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[36014481]
NPO14951 Zanthoxylum acanthopodium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[37471031]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[38538562]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[38606448]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[39598372]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12468.1 Asarum heterotropoides var. mandshuricum Varieties Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO9650 Zanthoxylum nitidum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8188 Hypoestes purpurea Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11809 Eleutherococcus sessiliflorus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10821 Magnolia praecocissima Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6280 Fagara xanthoxyloides n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO29744 Acanthopanax gracilistylus n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO31494 Acanthopanax senticosus n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO14951 Zanthoxylum acanthopodium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO30633 Acanthopanax sessiliflorus n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO10574 Machilus thunbergii Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4617 Tanacetum cinerariifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20362 Ruta montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17651 Bridelia retusa Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. Database[FooDB]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. Database[FooDB]
NPO31494 Acanthopanax senticosus n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30633 Acanthopanax sessiliflorus n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO12468.1 Asarum heterotropoides var. mandshuricum Varieties Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9650 Zanthoxylum nitidum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6280 Fagara xanthoxyloides n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO29744 Acanthopanax gracilistylus n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO8188 Hypoestes purpurea Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10821 Magnolia praecocissima Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14951 Zanthoxylum acanthopodium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10574 Machilus thunbergii Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20362 Ruta montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3404 Magnolia mutabilis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17651 Bridelia retusa Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15460 Caulerpa sertularioides Species Caulerpaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11387 Semen sesami n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6336.1 Asarum sieboldii var. seoulensis Varieties Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29729 Fagara sp n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO11809 Eleutherococcus sessiliflorus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11387 Semen sesami n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO4617 Tanacetum cinerariifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12468.1 Asarum heterotropoides var. mandshuricum Varieties Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8500 Acanthopanax gracilistylus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10574 Machilus thunbergii Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20362 Ruta montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6280 Fagara xanthoxyloides n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO14951 Zanthoxylum acanthopodium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9650 Zanthoxylum nitidum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17651 Bridelia retusa Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8188 Hypoestes purpurea Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25911 Fagara sp. Species n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO10821 Magnolia praecocissima Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6336.1 Asarum sieboldii var. seoulensis Varieties Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15460 Caulerpa sertularioides Species Caulerpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3404 Magnolia mutabilis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30633 Acanthopanax sessiliflorus n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31494 Acanthopanax senticosus n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20362 Ruta montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9650 Zanthoxylum nitidum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29744 Acanthopanax gracilistylus n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3404 Magnolia mutabilis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9650 Zanthoxylum nitidum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8500 Acanthopanax gracilistylus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4617 Tanacetum cinerariifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15460 Caulerpa sertularioides Species Caulerpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10574 Machilus thunbergii Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14951 Zanthoxylum acanthopodium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20362 Ruta montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11809 Eleutherococcus sessiliflorus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10821 Magnolia praecocissima Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8188 Hypoestes purpurea Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17651 Bridelia retusa Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3404 Magnolia mutabilis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8500 Acanthopanax gracilistylus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9650 Zanthoxylum nitidum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26237 Piper longum Species Piperaceae 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
NPT152 Individual protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 29092.9 nM PubChem BioAssay data set
NPT135 Individual protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 100000.0 nM PubChem BioAssay data set
NPT154 Individual protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 15848.9 nM PubChem BioAssay data set
NPT101 Individual protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 28183.8 nM PubChem BioAssay data set
NPT11 Individual protein Guanine nucleotide-binding protein G(s), subunit alpha Homo sapiens Potency n.a. 50118.7 nM PubChem BioAssay data set
NPT160 Individual protein TAR DNA-binding protein 43 Homo sapiens Potency n.a. 11220.2 nM PubChem BioAssay data set
NPT8 Individual protein DNA polymerase iota Homo sapiens Potency n.a. 31622.8 nM PubChem BioAssay data set
NPT535 Individual protein Parathyroid hormone receptor Homo sapiens Potency n.a. 100000.0 nM PubChem BioAssay data set
NPT64 Individual protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 18348.9 nM PubChem BioAssay data set

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT65 Cell line HepG2 Homo sapiens Potency n.a. 891.3 nM PubChem BioAssay data set
NPT2 Others Unspecified n.a. Potency n.a. 115.8 nM PubChem BioAssay data set

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 NPC16830 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
1.0 High Similarity NPC171928
1.0 High Similarity NPC158526
1.0 High Similarity NPC129687
1.0 High Similarity NPC33611
1.0 High Similarity NPC100223
0.8974 High Similarity NPC227160
0.8974 High Similarity NPC82111
0.8537 High Similarity NPC189474
0.7609 Intermediate Similarity NPC298317
0.7609 Intermediate Similarity NPC255566
0.7333 Intermediate Similarity NPC14022
0.7333 Intermediate Similarity NPC601703
0.7292 Intermediate Similarity NPC88640
0.7292 Intermediate Similarity NPC101153
0.7292 Intermediate Similarity NPC193666
0.7292 Intermediate Similarity NPC123526
0.7292 Intermediate Similarity NPC608725
0.7179 Intermediate Similarity NPC121783
0.7179 Intermediate Similarity NPC34902
0.7179 Intermediate Similarity NPC18449
0.7021 Intermediate Similarity NPC469981
0.6735 Remote Similarity NPC474139
0.6735 Remote Similarity NPC483653
0.6585 Remote Similarity NPC271208
0.6585 Remote Similarity NPC233224
0.6585 Remote Similarity NPC610263
0.6512 Remote Similarity NPC148893
0.6512 Remote Similarity NPC222127
0.6512 Remote Similarity NPC25333
0.6512 Remote Similarity NPC49235
0.6512 Remote Similarity NPC82862
0.6364 Remote Similarity NPC606146
0.6136 Remote Similarity NPC480478
0.6111 Remote Similarity NPC311057
0.6 Remote Similarity NPC57119
0.6 Remote Similarity NPC158471
0.6 Remote Similarity NPC226862
0.5962 Remote Similarity NPC47181
0.5882 Remote Similarity NPC101807
0.587 Remote Similarity NPC312199
0.58 Remote Similarity NPC165128
0.5745 Remote Similarity NPC483654
0.5652 Remote Similarity NPC137487
0.5625 Remote Similarity NPC487685
0.561 Remote Similarity NPC281864
0.561 Remote Similarity NPC328682
0.561 Remote Similarity NPC54321
0.56 Remote Similarity NPC185071
0.56 Remote Similarity NPC27843
0.56 Remote Similarity NPC7171
0.5536 Remote Similarity NPC600032
0.5345 Remote Similarity NPC265154
0.5306 Remote Similarity NPC488505
0.5217 Remote Similarity NPC600801
0.5147 Remote Similarity NPC486098
0.5094 Remote Similarity NPC135777
0.5094 Remote Similarity NPC7744
0.5091 Remote Similarity NPC12728
0.5088 Remote Similarity NPC254163

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC16830 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