Structure

Physi-Chem Properties

Molecular Weight:  354.11
Volume:  340.06
LogP:  3.326
LogD:  3.008
LogS:  -5.711
# Rotatable Bonds:  2
TPSA:  55.38
# H-Bond Aceptor:  6
# H-Bond Donor:  0
# Rings:  6
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.825
Synthetic Accessibility Score:  3.774
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.904
MDCK Permeability:  6.200259667821229e-05
Pgp-inhibitor:  0.813
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.001
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.042

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.177
Plasma Protein Binding (PPB):  96.76363372802734%
Volume Distribution (VD):  0.888
Pgp-substrate:  2.6137969493865967%

ADMET: Metabolism

CYP1A2-inhibitor:  0.617
CYP1A2-substrate:  0.314
CYP2C19-inhibitor:  0.949
CYP2C19-substrate:  0.211
CYP2C9-inhibitor:  0.779
CYP2C9-substrate:  0.778
CYP2D6-inhibitor:  0.959
CYP2D6-substrate:  0.917
CYP3A4-inhibitor:  0.964
CYP3A4-substrate:  0.511

ADMET: Excretion

Clearance (CL):  18.247
Half-life (T1/2):  0.062

ADMET: Toxicity

hERG Blockers:  0.243
Human Hepatotoxicity (H-HT):  0.24
Drug-inuced Liver Injury (DILI):  0.889
AMES Toxicity:  0.755
Rat Oral Acute Toxicity:  0.153
Maximum Recommended Daily Dose:  0.697
Skin Sensitization:  0.728
Carcinogencity:  0.866
Eye Corrosion:  0.003
Eye Irritation:  0.228
Respiratory Toxicity:  0.436

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC16830

Natural Product ID:  NPC16830
Common 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
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:  
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
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

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  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]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. leaf n.a. PMID[17125224]
NPO31494 Acanthopanax senticosus n.a. n.a. n.a. n.a. n.a. 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]
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]
NPO10821 Magnolia praecocissima Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3404 Magnolia mutabilis Species Magnoliaceae 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]
NPO9290 Zanthoxylum piperitum Species Rutaceae 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]
NPO31494 Acanthopanax senticosus 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]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22079 Paulownia tomentosa Species Paulowniaceae 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]
NPO14951 Zanthoxylum acanthopodium Species Rutaceae 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]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8188 Hypoestes purpurea Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9650 Zanthoxylum nitidum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17651 Bridelia retusa Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10506 Artemisia apiacea Species Asteraceae 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]
NPO6336.1 Asarum sieboldii var. seoulensis Varieties Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15460 Caulerpa sertularioides Species Caulerpaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15460 Caulerpa sertularioides Species Caulerpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8500 Acanthopanax gracilistylus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10821 Magnolia praecocissima Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22079 Paulownia tomentosa Species Paulowniaceae 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]
NPO12468.1 Asarum heterotropoides var. mandshuricum Varieties Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10574 Machilus thunbergii Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9650 Zanthoxylum nitidum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8188 Hypoestes purpurea Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26237 Piper longum Species Piperaceae 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]
NPO11387 Semen sesami 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]
NPO20362 Ruta montana 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]
NPO4617 Tanacetum cinerariifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11809 Eleutherococcus sessiliflorus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3404 Magnolia mutabilis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17651 Bridelia retusa Species Phyllanthaceae 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]
NPO3404 Magnolia mutabilis Species Magnoliaceae 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]
NPO20362 Ruta montana 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]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1382 Hyptis tomentosa Species Lamiaceae 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]
NPO9290 Zanthoxylum piperitum Species Rutaceae 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]
NPO9650 Zanthoxylum nitidum Species Rutaceae 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]
NPO26237 Piper longum Species Piperaceae Eukaryota 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]
NPO6336 Asarum sieboldii Species Aristolochiaceae 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]
NPO26237 Piper longum Species Piperaceae 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]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
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]
NPO11809 Eleutherococcus sessiliflorus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10506 Artemisia apiacea 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]
NPO20362 Ruta montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8500 Acanthopanax gracilistylus 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]
NPO4617 Tanacetum cinerariifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO542 Artemisia absinthium 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]
NPO9650 Zanthoxylum nitidum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10574 Machilus thunbergii Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14951 Zanthoxylum acanthopodium 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]
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 NP ID 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

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 PMID[500641]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 18348.9 nM PMID[500641]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 100000.0 nM PMID[500641]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 891.3 nM PMID[500641]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 15848.9 nM PMID[500641]
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 28183.8 nM PMID[500641]
NPT11 Individual Protein Guanine nucleotide-binding protein G(s), subunit alpha Homo sapiens Potency n.a. 50118.7 nM PMID[500641]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 25929.0 nM PMID[500641]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 29092.9 nM PMID[500641]
NPT160 Individual Protein TAR DNA-binding protein 43 Homo sapiens Potency n.a. 11220.2 nM PMID[500641]
NPT535 Individual Protein Parathyroid hormone receptor Homo sapiens Potency n.a. 100000.0 nM PMID[500641]
NPT2 Others Unspecified Potency n.a. 115.8 nM PMID[500641]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 31622.8 nM PMID[500641]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  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>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC129687
1.0 High Similarity NPC33611
1.0 High Similarity NPC158526
1.0 High Similarity NPC171928
1.0 High Similarity NPC100223
0.9762 High Similarity NPC227160
0.9762 High Similarity NPC82111
0.9683 High Similarity NPC233224
0.9683 High Similarity NPC271208
0.9615 High Similarity NPC101807
0.9615 High Similarity NPC469981
0.9535 High Similarity NPC47181
0.9524 High Similarity NPC158471
0.9524 High Similarity NPC57119
0.9524 High Similarity NPC226862
0.9524 High Similarity NPC165128
0.9462 High Similarity NPC189474
0.9462 High Similarity NPC18576
0.9462 High Similarity NPC474139
0.9398 High Similarity NPC312199
0.9385 High Similarity NPC31530
0.938 High Similarity NPC7744
0.9328 High Similarity NPC311057
0.9313 High Similarity NPC148893
0.9313 High Similarity NPC25333
0.9313 High Similarity NPC49235
0.9308 High Similarity NPC266848
0.9308 High Similarity NPC136750
0.9291 High Similarity NPC158737
0.9248 High Similarity NPC88640
0.9248 High Similarity NPC193666
0.9248 High Similarity NPC123526
0.9231 High Similarity NPC65183
0.9231 High Similarity NPC261812
0.9231 High Similarity NPC72046
0.9206 High Similarity NPC18449
0.9206 High Similarity NPC121783
0.9206 High Similarity NPC34902
0.9154 High Similarity NPC192255
0.9111 High Similarity NPC471908
0.9104 High Similarity NPC113550
0.9091 High Similarity NPC170779
0.9091 High Similarity NPC90083
0.9084 High Similarity NPC147616
0.9084 High Similarity NPC259742
0.9084 High Similarity NPC104077
0.9084 High Similarity NPC219671
0.9077 High Similarity NPC134764
0.9077 High Similarity NPC171550
0.9037 High Similarity NPC46591
0.9023 High Similarity NPC142547
0.9023 High Similarity NPC135777
0.8978 High Similarity NPC298317
0.8978 High Similarity NPC265154
0.8978 High Similarity NPC255566
0.8968 High Similarity NPC126935
0.8968 High Similarity NPC216929
0.8968 High Similarity NPC312713
0.8968 High Similarity NPC80241
0.8968 High Similarity NPC301641
0.8968 High Similarity NPC65933
0.8968 High Similarity NPC172676
0.8968 High Similarity NPC57268
0.8963 High Similarity NPC156376
0.8955 High Similarity NPC121651
0.8923 High Similarity NPC222127
0.8923 High Similarity NPC82862
0.8915 High Similarity NPC40352
0.8915 High Similarity NPC213711
0.8905 High Similarity NPC474295
0.8897 High Similarity NPC56091
0.8889 High Similarity NPC185908
0.8881 High Similarity NPC174191
0.8855 High Similarity NPC476748
0.8846 High Similarity NPC8050
0.8846 High Similarity NPC473093
0.8846 High Similarity NPC473092
0.8841 High Similarity NPC12728
0.8841 High Similarity NPC185071
0.8815 High Similarity NPC11453
0.881 High Similarity NPC344161
0.8797 High Similarity NPC471505
0.8786 High Similarity NPC3982
0.8779 High Similarity NPC328682
0.8779 High Similarity NPC281864
0.8779 High Similarity NPC54321
0.8777 High Similarity NPC179521
0.8777 High Similarity NPC166884
0.8777 High Similarity NPC477701
0.8777 High Similarity NPC141569
0.8769 High Similarity NPC112571
0.8769 High Similarity NPC206882
0.8769 High Similarity NPC285725
0.8769 High Similarity NPC50683
0.8768 High Similarity NPC472562
0.8768 High Similarity NPC80326
0.8768 High Similarity NPC246947
0.8759 High Similarity NPC216434
0.8759 High Similarity NPC103448
0.8759 High Similarity NPC177868
0.875 High Similarity NPC166184
0.875 High Similarity NPC283949
0.8741 High Similarity NPC184938
0.8741 High Similarity NPC150534
0.8741 High Similarity NPC101624
0.8731 High Similarity NPC1474
0.8731 High Similarity NPC196937
0.8722 High Similarity NPC161557
0.8722 High Similarity NPC7171
0.8722 High Similarity NPC27843
0.8722 High Similarity NPC115207
0.8722 High Similarity NPC228346
0.8722 High Similarity NPC158079
0.8722 High Similarity NPC40432
0.8714 High Similarity NPC469586
0.8714 High Similarity NPC205316
0.8705 High Similarity NPC477898
0.8696 High Similarity NPC300798
0.8696 High Similarity NPC58137
0.8676 High Similarity NPC143895
0.8667 High Similarity NPC19890
0.8667 High Similarity NPC110958
0.8657 High Similarity NPC181049
0.8657 High Similarity NPC207400
0.8657 High Similarity NPC106739
0.8643 High Similarity NPC177644
0.8643 High Similarity NPC191158
0.8643 High Similarity NPC84181
0.8636 High Similarity NPC470084
0.8633 High Similarity NPC287124
0.8633 High Similarity NPC302506
0.8633 High Similarity NPC174522
0.8626 High Similarity NPC186845
0.8626 High Similarity NPC88297
0.8626 High Similarity NPC9891
0.8623 High Similarity NPC226547
0.8623 High Similarity NPC278076
0.8613 High Similarity NPC14022
0.8593 High Similarity NPC169973
0.8582 High Similarity NPC22150
0.8582 High Similarity NPC180953
0.8582 High Similarity NPC38041
0.8582 High Similarity NPC279298
0.8571 High Similarity NPC474808
0.8561 High Similarity NPC472711
0.8561 High Similarity NPC177167
0.8561 High Similarity NPC98745
0.854 High Similarity NPC32189
0.8521 High Similarity NPC112861
0.8521 High Similarity NPC205796
0.8521 High Similarity NPC276753
0.8519 High Similarity NPC4940
0.8511 High Similarity NPC92693
0.8511 High Similarity NPC218841
0.8507 High Similarity NPC275950
0.8507 High Similarity NPC242807
0.8507 High Similarity NPC64201
0.8507 High Similarity NPC187998
0.8507 High Similarity NPC153739
0.8507 High Similarity NPC257582
0.8507 High Similarity NPC77040
0.8507 High Similarity NPC42300
0.8507 High Similarity NPC145305
0.8507 High Similarity NPC241522
0.8507 High Similarity NPC174495
0.8507 High Similarity NPC92164
0.85 High Similarity NPC176586
0.85 High Similarity NPC210354
0.8496 Intermediate Similarity NPC129570
0.8496 Intermediate Similarity NPC45774
0.8496 Intermediate Similarity NPC184733
0.8496 Intermediate Similarity NPC282703
0.8496 Intermediate Similarity NPC21867
0.8496 Intermediate Similarity NPC128208
0.8496 Intermediate Similarity NPC11258
0.8478 Intermediate Similarity NPC196420
0.8478 Intermediate Similarity NPC474039
0.8472 Intermediate Similarity NPC240521
0.8467 Intermediate Similarity NPC236522
0.8467 Intermediate Similarity NPC99572
0.8467 Intermediate Similarity NPC126409
0.8456 Intermediate Similarity NPC205915
0.8451 Intermediate Similarity NPC18979
0.8451 Intermediate Similarity NPC42716
0.8451 Intermediate Similarity NPC474749
0.8451 Intermediate Similarity NPC477702
0.8451 Intermediate Similarity NPC11422
0.8451 Intermediate Similarity NPC178014
0.8444 Intermediate Similarity NPC476345
0.8444 Intermediate Similarity NPC277804
0.844 Intermediate Similarity NPC470950
0.844 Intermediate Similarity NPC185307
0.8433 Intermediate Similarity NPC475875
0.8417 Intermediate Similarity NPC9068
0.8409 Intermediate Similarity NPC17348
0.8406 Intermediate Similarity NPC25695
0.8406 Intermediate Similarity NPC78047
0.8406 Intermediate Similarity NPC230968
0.8406 Intermediate Similarity NPC172818
0.8406 Intermediate Similarity NPC102260

  Chemically structural similarity: II. 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>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.8672 High Similarity NPD3705 Approved
0.8254 Intermediate Similarity NPD5283 Phase 1
0.7899 Intermediate Similarity NPD3027 Phase 3
0.7843 Intermediate Similarity NPD4966 Approved
0.7843 Intermediate Similarity NPD4965 Approved
0.7843 Intermediate Similarity NPD4967 Phase 2
0.7744 Intermediate Similarity NPD1357 Approved
0.7742 Intermediate Similarity NPD6234 Discontinued
0.7703 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD37 Approved
0.7568 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD6674 Discontinued
0.7518 Intermediate Similarity NPD2981 Phase 2
0.75 Intermediate Similarity NPD2861 Phase 2
0.7483 Intermediate Similarity NPD1613 Approved
0.7483 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7464 Intermediate Similarity NPD2983 Phase 2
0.7464 Intermediate Similarity NPD2982 Phase 2
0.7434 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD7199 Phase 2
0.7415 Intermediate Similarity NPD1375 Discontinued
0.7407 Intermediate Similarity NPD7228 Approved
0.74 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD3018 Phase 2
0.7333 Intermediate Similarity NPD5536 Phase 2
0.7333 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7319 Intermediate Similarity NPD1091 Approved
0.7297 Intermediate Similarity NPD7266 Discontinued
0.7285 Intermediate Similarity NPD5058 Phase 3
0.7254 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD7240 Approved
0.7222 Intermediate Similarity NPD5109 Approved
0.7222 Intermediate Similarity NPD5110 Phase 2
0.7222 Intermediate Similarity NPD5111 Phase 2
0.72 Intermediate Similarity NPD4237 Approved
0.72 Intermediate Similarity NPD4236 Phase 3
0.7192 Intermediate Similarity NPD3657 Discovery
0.7162 Intermediate Similarity NPD4108 Discontinued
0.7161 Intermediate Similarity NPD4210 Discontinued
0.7152 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD2978 Approved
0.7152 Intermediate Similarity NPD2977 Approved
0.7152 Intermediate Similarity NPD4110 Phase 3
0.7143 Intermediate Similarity NPD228 Approved
0.7123 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD3620 Phase 2
0.7115 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD5327 Phase 3
0.7091 Intermediate Similarity NPD3818 Discontinued
0.7089 Intermediate Similarity NPD3382 Approved
0.7089 Intermediate Similarity NPD3384 Approved
0.7089 Intermediate Similarity NPD3383 Approved
0.7083 Intermediate Similarity NPD4908 Phase 1
0.7083 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD1610 Phase 2
0.707 Intermediate Similarity NPD7028 Phase 2
0.7059 Intermediate Similarity NPD7124 Phase 2
0.7059 Intermediate Similarity NPD7157 Approved
0.7051 Intermediate Similarity NPD1653 Approved
0.705 Intermediate Similarity NPD5125 Phase 3
0.705 Intermediate Similarity NPD5126 Approved
0.7047 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD5588 Approved
0.7047 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD2684 Approved
0.7044 Intermediate Similarity NPD5563 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD6331 Phase 2
0.7037 Intermediate Similarity NPD5494 Approved
0.7019 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD4060 Phase 1
0.7 Intermediate Similarity NPD2438 Suspended
0.7 Intermediate Similarity NPD2161 Phase 2
0.6992 Remote Similarity NPD3022 Approved
0.6992 Remote Similarity NPD3021 Approved
0.6986 Remote Similarity NPD4907 Clinical (unspecified phase)
0.698 Remote Similarity NPD6895 Approved
0.698 Remote Similarity NPD6896 Approved
0.6978 Remote Similarity NPD5585 Approved
0.6974 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6972 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6963 Remote Similarity NPD7843 Approved
0.6963 Remote Similarity NPD5535 Approved
0.6959 Remote Similarity NPD6355 Discontinued
0.6959 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6959 Remote Similarity NPD5735 Approved
0.6939 Remote Similarity NPD554 Clinical (unspecified phase)
0.6939 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6929 Remote Similarity NPD17 Approved
0.6928 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6913 Remote Similarity NPD2492 Phase 1
0.6906 Remote Similarity NPD1182 Approved
0.6901 Remote Similarity NPD1840 Phase 2
0.6901 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6894 Remote Similarity NPD6374 Clinical (unspecified phase)
0.6892 Remote Similarity NPD2979 Phase 3
0.6887 Remote Similarity NPD3539 Phase 1
0.6879 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6867 Remote Similarity NPD6111 Discontinued
0.6867 Remote Similarity NPD4538 Approved
0.6867 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6867 Remote Similarity NPD4536 Approved
0.6866 Remote Similarity NPD5451 Approved
0.6863 Remote Similarity NPD3060 Approved
0.6857 Remote Similarity NPD5691 Approved
0.6853 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6842 Remote Similarity NPD3540 Phase 1
0.6842 Remote Similarity NPD5763 Approved
0.6842 Remote Similarity NPD5762 Approved
0.6842 Remote Similarity NPD1358 Approved
0.6832 Remote Similarity NPD8455 Phase 2
0.6824 Remote Similarity NPD7685 Pre-registration
0.6821 Remote Similarity NPD5960 Phase 3
0.6815 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6815 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6812 Remote Similarity NPD6387 Discontinued
0.681 Remote Similarity NPD5604 Discontinued
0.6809 Remote Similarity NPD5846 Approved
0.6809 Remote Similarity NPD6516 Phase 2
0.6806 Remote Similarity NPD8651 Approved
0.6806 Remote Similarity NPD2922 Phase 1
0.6805 Remote Similarity NPD7074 Phase 3
0.6803 Remote Similarity NPD7095 Approved
0.6786 Remote Similarity NPD1548 Phase 1
0.6783 Remote Similarity NPD1608 Approved
0.6779 Remote Similarity NPD2238 Phase 2
0.6779 Remote Similarity NPD1558 Phase 1
0.6779 Remote Similarity NPD4140 Approved
0.6772 Remote Similarity NPD5976 Discontinued
0.677 Remote Similarity NPD1934 Approved
0.677 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6767 Remote Similarity NPD3134 Approved
0.6765 Remote Similarity NPD1137 Approved
0.6765 Remote Similarity NPD1139 Approved
0.6758 Remote Similarity NPD7680 Approved
0.6757 Remote Similarity NPD5718 Phase 2
0.6755 Remote Similarity NPD7119 Phase 2
0.6755 Remote Similarity NPD7097 Phase 1
0.6753 Remote Similarity NPD4162 Approved
0.6753 Remote Similarity NPD5177 Phase 3
0.6752 Remote Similarity NPD4123 Phase 3
0.6746 Remote Similarity NPD7054 Approved
0.6738 Remote Similarity NPD1651 Approved
0.6736 Remote Similarity NPD3685 Discontinued
0.6736 Remote Similarity NPD4359 Approved
0.6732 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6715 Remote Similarity NPD1138 Approved
0.6713 Remote Similarity NPD1281 Approved
0.6711 Remote Similarity NPD6233 Phase 2
0.671 Remote Similarity NPD4628 Phase 3
0.6709 Remote Similarity NPD7526 Approved
0.6709 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6709 Remote Similarity NPD52 Approved
0.6708 Remote Similarity NPD6385 Approved
0.6708 Remote Similarity NPD6386 Approved
0.6706 Remote Similarity NPD7472 Approved
0.6691 Remote Similarity NPD709 Approved
0.6689 Remote Similarity NPD6353 Approved
0.6689 Remote Similarity NPD6653 Approved
0.6688 Remote Similarity NPD4664 Clinical (unspecified phase)
0.6688 Remote Similarity NPD1372 Clinical (unspecified phase)
0.6687 Remote Similarity NPD8127 Discontinued
0.6687 Remote Similarity NPD3817 Phase 2
0.6687 Remote Similarity NPD4005 Discontinued
0.6687 Remote Similarity NPD2563 Approved
0.6687 Remote Similarity NPD2560 Approved
0.6667 Remote Similarity NPD3454 Phase 3
0.6667 Remote Similarity NPD7296 Approved
0.6667 Remote Similarity NPD2231 Phase 2
0.6667 Remote Similarity NPD2677 Approved
0.6667 Remote Similarity NPD4481 Phase 3
0.6667 Remote Similarity NPD2235 Phase 2
0.6667 Remote Similarity NPD4420 Approved
0.6646 Remote Similarity NPD4678 Approved
0.6646 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6646 Remote Similarity NPD3882 Suspended
0.6646 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6646 Remote Similarity NPD4675 Approved
0.6644 Remote Similarity NPD6798 Discontinued
0.6644 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6643 Remote Similarity NPD3596 Phase 2
0.6642 Remote Similarity NPD968 Approved
0.663 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6626 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6626 Remote Similarity NPD5772 Approved
0.6626 Remote Similarity NPD5773 Approved
0.6625 Remote Similarity NPD3686 Approved
0.6625 Remote Similarity NPD3687 Approved
0.6623 Remote Similarity NPD6002 Phase 3
0.6623 Remote Similarity NPD1933 Approved
0.6623 Remote Similarity NPD6004 Phase 3
0.6623 Remote Similarity NPD4340 Discontinued
0.6623 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6623 Remote Similarity NPD6005 Phase 3
0.6623 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6621 Remote Similarity NPD4749 Approved
0.6607 Remote Similarity NPD5242 Approved
0.6606 Remote Similarity NPD4381 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

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