Structure

Physi-Chem Properties

Molecular Weight:  234.16
Volume:  260.554
LogP:  2.36
LogD:  1.853
LogS:  -3.848
# Rotatable Bonds:  1
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.708
Synthetic Accessibility Score:  4.154
Fsp3:  0.667
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.716
MDCK Permeability:  1.9044304281123914e-05
Pgp-inhibitor:  0.054
Pgp-substrate:  0.014
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.058
30% Bioavailability (F30%):  0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.069
Plasma Protein Binding (PPB):  76.76305389404297%
Volume Distribution (VD):  1.388
Pgp-substrate:  23.934633255004883%

ADMET: Metabolism

CYP1A2-inhibitor:  0.041
CYP1A2-substrate:  0.241
CYP2C19-inhibitor:  0.123
CYP2C19-substrate:  0.846
CYP2C9-inhibitor:  0.045
CYP2C9-substrate:  0.398
CYP2D6-inhibitor:  0.023
CYP2D6-substrate:  0.505
CYP3A4-inhibitor:  0.051
CYP3A4-substrate:  0.307

ADMET: Excretion

Clearance (CL):  7.398
Half-life (T1/2):  0.667

ADMET: Toxicity

hERG Blockers:  0.035
Human Hepatotoxicity (H-HT):  0.209
Drug-inuced Liver Injury (DILI):  0.083
AMES Toxicity:  0.07
Rat Oral Acute Toxicity:  0.959
Maximum Recommended Daily Dose:  0.957
Skin Sensitization:  0.625
Carcinogencity:  0.712
Eye Corrosion:  0.193
Eye Irritation:  0.824
Respiratory Toxicity:  0.944

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  Natural Product: NPC178852

Natural Product ID:  NPC178852
Common Name*:   Ligucyperonol
IUPAC Name:   (4R,4aR,7R)-4-hydroxy-1,4a-dimethyl-7-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one
Synonyms:   Ligucyperonol
Standard InCHIKey:  MROVETGJOLYNJI-KCPJHIHWSA-N
Standard InCHI:  InChI=1S/C15H22O2/c1-9(2)11-5-6-15(4)12(7-11)10(3)13(16)8-14(15)17/h11,14,17H,1,5-8H2,2-4H3/t11-,14-,15-/m1/s1
SMILES:  C=C(C)[C@@H]1CC[C@]2(C)C(=C(C)C(=O)C[C@H]2O)C1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL462897
PubChem CID:   14681770
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

*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
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(81)85171-0]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. DOI[10.3987/COM-96-7609.]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/JMPR.9000078]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[10705751]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota Whole plant n.a. n.a. PMID[11141121]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[11514174]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. flower n.a. PMID[12130858]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota fruit Hainan Island, China 1998 PMID[12398545]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. seed n.a. PMID[12822897]
NPO7630 Cyperus longus Species Cyperaceae Eukaryota n.a. Egyptian herbal medicine n.a. PMID[15104485]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[16038566]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. stem n.a. PMID[16964757]
NPO22375 Saussurea salicifolia Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[18057725]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. root n.a. PMID[18064621]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[18064621]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[18081254]
NPO24900 Vladimiria muliensis n.a. n.a. n.a. n.a. n.a. n.a. PMID[18293903]
NPO24900 Vladimiria muliensis n.a. n.a. n.a. n.a. n.a. n.a. PMID[19432411]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[22277277]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. rhizome n.a. PMID[23059629]
NPO40202 Microsphaeropsis arundinis Species Eukaryota n.a. n.a. n.a. PMID[23294378]
NPO25106 Arnica parryi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[23583435]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. root n.a. PMID[24257774]
NPO27031 Methanosarcina barkeri Species Methanosarcinaceae Archaea n.a. n.a. n.a. PMID[24669201]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[25757283]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[26099993]
NPO1451 Aspergillus duricaulis Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26517152]
NPO25179 Guilandina bonduc Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26756595]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28156114]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[29400471]
NPO26787 Chloranthus anhuiensis Species Chloranthaceae Eukaryota n.a. n.a. n.a. PMID[29775304]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Aerial Parts n.a. n.a. PMID[30726671]
NPO24843 Pachygone dasycarpa Species Menispermaceae Eukaryota stem bark n.a. n.a. PMID[9157192]
NPO24843 Pachygone dasycarpa Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[9157192]
NPO1674 Dalbergia nitidula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14304 Physalis alkekengi Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23547 Strychnos amazonica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23478 Uncaria africana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24328 Gratiola officinalis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29503 Alstonia spectabilis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14304 Physalis alkekengi Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24328 Gratiola officinalis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29503 Alstonia spectabilis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23478 Uncaria africana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1674 Dalbergia nitidula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2545 Aster scaber Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23547 Strychnos amazonica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23288 Justicia betonica Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23547 Strychnos amazonica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14304 Physalis alkekengi Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24191 Drypetes tessmanniana Species Putranjivaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2545 Aster scaber Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25106 Arnica parryi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24118 Buxus hildebrandtii Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27277 Stenocarpella maydis Species Diaporthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29503 Alstonia spectabilis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23750 Escontria chiotilla Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24688 Streptomyces ramocissimus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO19716 Uvaria lucida Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24021 Eucryphia cordifolia Species Cunoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17445 Streptomyces corchorusii Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO24659 Eremurus chinensis Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18088 Euglena longa Species Euglenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1380 Phylica rogersii Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24456 Salvia lavandulifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23547 Strychnos amazonica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24328 Gratiola officinalis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13455 Hemiselmis virescens Species Hemiselmidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16880 Lupinus texensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24589 Grindelia discoidea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1451 Aspergillus duricaulis Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2343 Haplopappus arbutoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4484 Maytenus obtusifolia Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3691 Albizia mollis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3817 Chrysosporium queenslandicum Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16791 Ligularia virgaurea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21799 Bacillus litoralis Species Bacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22375 Saussurea salicifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23657 Ophiocordyceps heteropoda Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22924 Bombus terrestris Species Apidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28259 Viguiera pinnatilobata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27093 Kniphofia foliosa Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24900 Vladimiria muliensis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO27031 Methanosarcina barkeri Species Methanosarcinaceae Archaea n.a. n.a. n.a. Database[UNPD]
NPO18875 Aconitum contortum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23375 Hypericum reptans Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24813 Agardhiella tenera Species Solieriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14304 Physalis alkekengi Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10901 Tessaria dodoneaefolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24969 Ageratum mexicanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25179 Guilandina bonduc Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24493 Echinacea simulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23660 Alpinia zerumbet Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24406 Rhizophora tagal Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23149 Callistemon coccineus Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4851 Penstemon confertus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7529 Viscum multinerve Species Viscaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24843 Pachygone dasycarpa Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23478 Uncaria africana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24874 Croton geayi Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3771 Sphaeria sassafras n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO7630 Cyperus longus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23288 Justicia betonica Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18045 Holothuria atra Species Holothuriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1674 Dalbergia nitidula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4944 Bactris plumeriana Species Arecaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24937 Callicarpa acuminata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26787 Chloranthus anhuiensis Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23837 Rubus laciniatus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25226 Kalanchoe spathulata Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25031 Petunia nyctaginiflora Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25068 Zebrina pendula Species Enidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25130 Hylotrupes bajulus Species Cerambycidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21483 0nomuraea dietziae Species Streptosporangiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5035 Schistostephium heptalobum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21242 Neolitsea villosa Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24754 Tsitsikamma favus Species Latrunculiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3315 Eucalyptus hybr Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24268 Pteryxia terebinthina Species Apiaceae 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
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 5.5 % PMID[572066]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 13.9 % PMID[572066]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 12.6 % PMID[572066]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 46.7 % PMID[572066]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 12.14 ug.mL-1 PMID[572067]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 11.4 ug.mL-1 PMID[572068]

☑ 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 NPC178852 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
0.9079 High Similarity NPC281138
0.9067 High Similarity NPC197659
0.8718 High Similarity NPC172013
0.8642 High Similarity NPC15807
0.8625 High Similarity NPC64600
0.8608 High Similarity NPC14151
0.859 High Similarity NPC308038
0.8514 High Similarity NPC173321
0.85 High Similarity NPC93590
0.8481 Intermediate Similarity NPC148685
0.8481 Intermediate Similarity NPC2482
0.8481 Intermediate Similarity NPC157895
0.8481 Intermediate Similarity NPC104120
0.8462 Intermediate Similarity NPC207772
0.8442 Intermediate Similarity NPC470525
0.8442 Intermediate Similarity NPC263582
0.8421 Intermediate Similarity NPC470299
0.84 Intermediate Similarity NPC84790
0.8375 Intermediate Similarity NPC473420
0.8375 Intermediate Similarity NPC116797
0.8375 Intermediate Similarity NPC121984
0.8333 Intermediate Similarity NPC471722
0.8333 Intermediate Similarity NPC266193
0.8333 Intermediate Similarity NPC257666
0.8333 Intermediate Similarity NPC471724
0.8313 Intermediate Similarity NPC145879
0.8313 Intermediate Similarity NPC94666
0.8313 Intermediate Similarity NPC72133
0.8313 Intermediate Similarity NPC31564
0.8313 Intermediate Similarity NPC158393
0.8313 Intermediate Similarity NPC474733
0.8313 Intermediate Similarity NPC194417
0.8313 Intermediate Similarity NPC474732
0.8313 Intermediate Similarity NPC474778
0.8312 Intermediate Similarity NPC114236
0.8272 Intermediate Similarity NPC151519
0.8235 Intermediate Similarity NPC119416
0.8228 Intermediate Similarity NPC62336
0.8214 Intermediate Similarity NPC298904
0.8214 Intermediate Similarity NPC475740
0.8214 Intermediate Similarity NPC58063
0.8205 Intermediate Similarity NPC250621
0.8193 Intermediate Similarity NPC474853
0.8193 Intermediate Similarity NPC79573
0.8193 Intermediate Similarity NPC470574
0.8193 Intermediate Similarity NPC179006
0.8171 Intermediate Similarity NPC476082
0.8171 Intermediate Similarity NPC169941
0.8171 Intermediate Similarity NPC278648
0.8171 Intermediate Similarity NPC251475
0.8148 Intermediate Similarity NPC136150
0.814 Intermediate Similarity NPC473099
0.8125 Intermediate Similarity NPC229204
0.8118 Intermediate Similarity NPC328313
0.8118 Intermediate Similarity NPC473229
0.8118 Intermediate Similarity NPC131470
0.8118 Intermediate Similarity NPC143767
0.8118 Intermediate Similarity NPC206060
0.8118 Intermediate Similarity NPC472802
0.8118 Intermediate Similarity NPC328539
0.8108 Intermediate Similarity NPC96962
0.8101 Intermediate Similarity NPC203403
0.8101 Intermediate Similarity NPC74995
0.8095 Intermediate Similarity NPC472974
0.8095 Intermediate Similarity NPC472986
0.8095 Intermediate Similarity NPC472985
0.8095 Intermediate Similarity NPC222613
0.8095 Intermediate Similarity NPC118648
0.8095 Intermediate Similarity NPC179591
0.8095 Intermediate Similarity NPC470955
0.8095 Intermediate Similarity NPC475022
0.809 Intermediate Similarity NPC94337
0.8072 Intermediate Similarity NPC59453
0.8072 Intermediate Similarity NPC85774
0.8072 Intermediate Similarity NPC58841
0.8072 Intermediate Similarity NPC221758
0.8072 Intermediate Similarity NPC161423
0.8072 Intermediate Similarity NPC180834
0.8072 Intermediate Similarity NPC227064
0.8072 Intermediate Similarity NPC40687
0.8072 Intermediate Similarity NPC329043
0.8072 Intermediate Similarity NPC321187
0.8072 Intermediate Similarity NPC473246
0.8072 Intermediate Similarity NPC470812
0.8072 Intermediate Similarity NPC214043
0.8049 Intermediate Similarity NPC73882
0.8049 Intermediate Similarity NPC48362
0.8046 Intermediate Similarity NPC73457
0.8046 Intermediate Similarity NPC99380
0.8046 Intermediate Similarity NPC116726
0.8025 Intermediate Similarity NPC471514
0.8025 Intermediate Similarity NPC476809
0.8025 Intermediate Similarity NPC45495
0.8023 Intermediate Similarity NPC69627
0.8023 Intermediate Similarity NPC275740
0.8023 Intermediate Similarity NPC472970
0.8023 Intermediate Similarity NPC473999
0.8023 Intermediate Similarity NPC86319
0.8023 Intermediate Similarity NPC473100
0.8023 Intermediate Similarity NPC31985
0.8023 Intermediate Similarity NPC472971
0.8023 Intermediate Similarity NPC186688
0.8023 Intermediate Similarity NPC268406
0.8023 Intermediate Similarity NPC26959
0.8023 Intermediate Similarity NPC309603
0.8023 Intermediate Similarity NPC1015
0.8023 Intermediate Similarity NPC472489
0.8023 Intermediate Similarity NPC472983
0.8 Intermediate Similarity NPC73064
0.8 Intermediate Similarity NPC80088
0.8 Intermediate Similarity NPC272039
0.8 Intermediate Similarity NPC253561
0.8 Intermediate Similarity NPC220930
0.8 Intermediate Similarity NPC141292
0.8 Intermediate Similarity NPC109900
0.8 Intermediate Similarity NPC471916
0.8 Intermediate Similarity NPC475994
0.7978 Intermediate Similarity NPC280725
0.7978 Intermediate Similarity NPC148523
0.7976 Intermediate Similarity NPC469948
0.7976 Intermediate Similarity NPC202868
0.7976 Intermediate Similarity NPC133954
0.7976 Intermediate Similarity NPC197823
0.7975 Intermediate Similarity NPC186554
0.7975 Intermediate Similarity NPC76966
0.7975 Intermediate Similarity NPC472305
0.7955 Intermediate Similarity NPC134826
0.7955 Intermediate Similarity NPC109305
0.7952 Intermediate Similarity NPC471036
0.7952 Intermediate Similarity NPC291320
0.7952 Intermediate Similarity NPC105173
0.7931 Intermediate Similarity NPC183283
0.7931 Intermediate Similarity NPC134321
0.7931 Intermediate Similarity NPC191684
0.7931 Intermediate Similarity NPC128672
0.7931 Intermediate Similarity NPC85173
0.7931 Intermediate Similarity NPC48010
0.7927 Intermediate Similarity NPC472684
0.7927 Intermediate Similarity NPC470298
0.7927 Intermediate Similarity NPC119229
0.7927 Intermediate Similarity NPC44963
0.7907 Intermediate Similarity NPC310752
0.7907 Intermediate Similarity NPC230387
0.7907 Intermediate Similarity NPC53911
0.7907 Intermediate Similarity NPC277771
0.7907 Intermediate Similarity NPC158778
0.7907 Intermediate Similarity NPC292491
0.7907 Intermediate Similarity NPC474677
0.7901 Intermediate Similarity NPC472490
0.7901 Intermediate Similarity NPC152061
0.7901 Intermediate Similarity NPC7232
0.7889 Intermediate Similarity NPC98874
0.7889 Intermediate Similarity NPC167193
0.7889 Intermediate Similarity NPC472806
0.7882 Intermediate Similarity NPC198761
0.7882 Intermediate Similarity NPC74363
0.7882 Intermediate Similarity NPC327115
0.7882 Intermediate Similarity NPC20688
0.7882 Intermediate Similarity NPC6979
0.7882 Intermediate Similarity NPC213412
0.7882 Intermediate Similarity NPC473226
0.7882 Intermediate Similarity NPC51014
0.7882 Intermediate Similarity NPC472494
0.7882 Intermediate Similarity NPC472491
0.7882 Intermediate Similarity NPC475862
0.7875 Intermediate Similarity NPC325946
0.7865 Intermediate Similarity NPC166906
0.7865 Intermediate Similarity NPC196227
0.7865 Intermediate Similarity NPC23170
0.7865 Intermediate Similarity NPC196485
0.7865 Intermediate Similarity NPC245972
0.7857 Intermediate Similarity NPC472265
0.7857 Intermediate Similarity NPC237712
0.7841 Intermediate Similarity NPC473998
0.7841 Intermediate Similarity NPC168027
0.7841 Intermediate Similarity NPC155304
0.7841 Intermediate Similarity NPC145067
0.7841 Intermediate Similarity NPC131872
0.7841 Intermediate Similarity NPC4036
0.7841 Intermediate Similarity NPC475806
0.7841 Intermediate Similarity NPC65120
0.7841 Intermediate Similarity NPC233116
0.7841 Intermediate Similarity NPC185936
0.7841 Intermediate Similarity NPC158030
0.7841 Intermediate Similarity NPC63748
0.7841 Intermediate Similarity NPC233455
0.7841 Intermediate Similarity NPC272746
0.7838 Intermediate Similarity NPC474304
0.7838 Intermediate Similarity NPC474329
0.7831 Intermediate Similarity NPC212083
0.7831 Intermediate Similarity NPC310989
0.7831 Intermediate Similarity NPC103486
0.7831 Intermediate Similarity NPC110780
0.7821 Intermediate Similarity NPC247586
0.7816 Intermediate Similarity NPC472475
0.7816 Intermediate Similarity NPC472477
0.7816 Intermediate Similarity NPC472973
0.7805 Intermediate Similarity NPC108955
0.7805 Intermediate Similarity NPC472478
0.7802 Intermediate Similarity NPC89225

  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 NPC178852 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
0.8313 Intermediate Similarity NPD3618 Phase 1
0.8272 Intermediate Similarity NPD3667 Approved
0.8072 Intermediate Similarity NPD4786 Approved
0.8072 Intermediate Similarity NPD3666 Approved
0.8072 Intermediate Similarity NPD3133 Approved
0.8072 Intermediate Similarity NPD3665 Phase 1
0.8023 Intermediate Similarity NPD5328 Approved
0.7841 Intermediate Similarity NPD6079 Approved
0.7841 Intermediate Similarity NPD7515 Phase 2
0.7753 Intermediate Similarity NPD4202 Approved
0.7674 Intermediate Similarity NPD5279 Phase 3
0.759 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD4695 Discontinued
0.75 Intermediate Similarity NPD5222 Approved
0.75 Intermediate Similarity NPD4697 Phase 3
0.75 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5221 Approved
0.7473 Intermediate Similarity NPD7748 Approved
0.7471 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD3668 Phase 3
0.7419 Intermediate Similarity NPD4755 Approved
0.7419 Intermediate Similarity NPD5173 Approved
0.7416 Intermediate Similarity NPD4753 Phase 2
0.7412 Intermediate Similarity NPD4223 Phase 3
0.7412 Intermediate Similarity NPD4221 Approved
0.7349 Intermediate Similarity NPD3617 Approved
0.7263 Intermediate Similarity NPD4700 Approved
0.7263 Intermediate Similarity NPD4696 Approved
0.7263 Intermediate Similarity NPD5286 Approved
0.7263 Intermediate Similarity NPD5285 Approved
0.7253 Intermediate Similarity NPD6411 Approved
0.7241 Intermediate Similarity NPD4197 Approved
0.7234 Intermediate Similarity NPD7902 Approved
0.7188 Intermediate Similarity NPD5223 Approved
0.7174 Intermediate Similarity NPD6399 Phase 3
0.7159 Intermediate Similarity NPD5329 Approved
0.7143 Intermediate Similarity NPD7341 Phase 2
0.7113 Intermediate Similarity NPD4633 Approved
0.7113 Intermediate Similarity NPD5224 Approved
0.7113 Intermediate Similarity NPD5211 Phase 2
0.7113 Intermediate Similarity NPD5225 Approved
0.7113 Intermediate Similarity NPD5226 Approved
0.7108 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD4688 Approved
0.7079 Intermediate Similarity NPD7146 Approved
0.7079 Intermediate Similarity NPD6409 Approved
0.7079 Intermediate Similarity NPD6684 Approved
0.7079 Intermediate Similarity NPD5330 Approved
0.7079 Intermediate Similarity NPD4693 Phase 3
0.7079 Intermediate Similarity NPD4689 Approved
0.7079 Intermediate Similarity NPD5690 Phase 2
0.7079 Intermediate Similarity NPD4623 Approved
0.7079 Intermediate Similarity NPD5280 Approved
0.7079 Intermediate Similarity NPD4690 Approved
0.7079 Intermediate Similarity NPD5205 Approved
0.7079 Intermediate Similarity NPD4138 Approved
0.7079 Intermediate Similarity NPD4519 Discontinued
0.7079 Intermediate Similarity NPD7521 Approved
0.7079 Intermediate Similarity NPD7334 Approved
0.7079 Intermediate Similarity NPD4694 Approved
0.7051 Intermediate Similarity NPD7331 Phase 2
0.7041 Intermediate Similarity NPD5175 Approved
0.7041 Intermediate Similarity NPD5174 Approved
0.7041 Intermediate Similarity NPD4754 Approved
0.7033 Intermediate Similarity NPD6101 Approved
0.7033 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD5210 Approved
0.7021 Intermediate Similarity NPD4629 Approved
0.6988 Remote Similarity NPD6942 Approved
0.6988 Remote Similarity NPD7339 Approved
0.697 Remote Similarity NPD5141 Approved
0.6966 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6966 Remote Similarity NPD1696 Phase 3
0.6966 Remote Similarity NPD1694 Approved
0.6961 Remote Similarity NPD4634 Approved
0.6932 Remote Similarity NPD4788 Approved
0.6923 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6923 Remote Similarity NPD6903 Approved
0.6915 Remote Similarity NPD7900 Approved
0.6915 Remote Similarity NPD7901 Clinical (unspecified phase)
0.69 Remote Similarity NPD6402 Approved
0.69 Remote Similarity NPD4767 Approved
0.69 Remote Similarity NPD5739 Approved
0.69 Remote Similarity NPD7128 Approved
0.69 Remote Similarity NPD4768 Approved
0.69 Remote Similarity NPD6675 Approved
0.6875 Remote Similarity NPD6084 Phase 2
0.6875 Remote Similarity NPD6083 Phase 2
0.686 Remote Similarity NPD7645 Phase 2
0.6848 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5695 Phase 3
0.6832 Remote Similarity NPD5701 Approved
0.6832 Remote Similarity NPD5697 Approved
0.6813 Remote Similarity NPD3573 Approved
0.6809 Remote Similarity NPD5778 Approved
0.6809 Remote Similarity NPD5779 Approved
0.6804 Remote Similarity NPD4225 Approved
0.679 Remote Similarity NPD3700 Clinical (unspecified phase)
0.679 Remote Similarity NPD4137 Phase 3
0.679 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6765 Remote Similarity NPD7320 Approved
0.6765 Remote Similarity NPD4730 Approved
0.6765 Remote Similarity NPD6011 Approved
0.6765 Remote Similarity NPD5168 Approved
0.6765 Remote Similarity NPD6881 Approved
0.6765 Remote Similarity NPD6899 Approved
0.6765 Remote Similarity NPD4729 Approved
0.6765 Remote Similarity NPD5128 Approved
0.6739 Remote Similarity NPD5737 Approved
0.6739 Remote Similarity NPD4518 Approved
0.6739 Remote Similarity NPD6672 Approved
0.6737 Remote Similarity NPD5282 Discontinued
0.6729 Remote Similarity NPD7115 Discovery
0.6707 Remote Similarity NPD4747 Approved
0.6707 Remote Similarity NPD4691 Approved
0.6705 Remote Similarity NPD4139 Approved
0.6705 Remote Similarity NPD4692 Approved
0.6702 Remote Similarity NPD5284 Approved
0.6702 Remote Similarity NPD5281 Approved
0.6699 Remote Similarity NPD6013 Approved
0.6699 Remote Similarity NPD6014 Approved
0.6699 Remote Similarity NPD6373 Approved
0.6699 Remote Similarity NPD6372 Approved
0.6699 Remote Similarity NPD6012 Approved
0.6667 Remote Similarity NPD6924 Approved
0.6667 Remote Similarity NPD4195 Approved
0.6667 Remote Similarity NPD6926 Approved
0.6667 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6635 Remote Similarity NPD5135 Approved
0.6635 Remote Similarity NPD5250 Approved
0.6635 Remote Similarity NPD5248 Approved
0.6635 Remote Similarity NPD5169 Approved
0.6635 Remote Similarity NPD6883 Approved
0.6635 Remote Similarity NPD5249 Phase 3
0.6635 Remote Similarity NPD7102 Approved
0.6635 Remote Similarity NPD5247 Approved
0.6635 Remote Similarity NPD7290 Approved
0.6635 Remote Similarity NPD5251 Approved
0.6635 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6633 Remote Similarity NPD5696 Approved
0.6633 Remote Similarity NPD7638 Approved
0.6627 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6627 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6625 Remote Similarity NPD3704 Approved
0.6596 Remote Similarity NPD4096 Approved
0.6596 Remote Similarity NPD5785 Approved
0.6593 Remote Similarity NPD5363 Approved
0.6591 Remote Similarity NPD4748 Discontinued
0.6591 Remote Similarity NPD7525 Registered
0.6588 Remote Similarity NPD8264 Approved
0.6571 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6571 Remote Similarity NPD5217 Approved
0.6571 Remote Similarity NPD5215 Approved
0.6571 Remote Similarity NPD6847 Approved
0.6571 Remote Similarity NPD6649 Approved
0.6571 Remote Similarity NPD5216 Approved
0.6571 Remote Similarity NPD8130 Phase 1
0.6571 Remote Similarity NPD6650 Approved
0.6571 Remote Similarity NPD6869 Approved
0.6571 Remote Similarity NPD6617 Approved
0.6571 Remote Similarity NPD5127 Approved
0.6566 Remote Similarity NPD7639 Approved
0.6566 Remote Similarity NPD7640 Approved
0.6517 Remote Similarity NPD5369 Approved
0.6512 Remote Similarity NPD6933 Approved
0.6509 Remote Similarity NPD6882 Approved
0.6509 Remote Similarity NPD8297 Approved
0.6505 Remote Similarity NPD6412 Phase 2
0.65 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6471 Remote Similarity NPD5733 Approved
0.6471 Remote Similarity NPD4687 Approved
0.6471 Remote Similarity NPD4058 Approved
0.6465 Remote Similarity NPD5290 Discontinued
0.6458 Remote Similarity NPD5133 Approved
0.6456 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6449 Remote Similarity NPD4632 Approved
0.6444 Remote Similarity NPD4269 Approved
0.6444 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6444 Remote Similarity NPD4270 Approved
0.6429 Remote Similarity NPD5276 Approved
0.6429 Remote Similarity NPD7150 Approved
0.6429 Remote Similarity NPD7151 Approved
0.6429 Remote Similarity NPD7152 Approved
0.6408 Remote Similarity NPD6008 Approved
0.6404 Remote Similarity NPD7509 Discontinued
0.6396 Remote Similarity NPD6059 Approved
0.6396 Remote Similarity NPD6319 Approved
0.6396 Remote Similarity NPD6054 Approved
0.6395 Remote Similarity NPD3703 Phase 2
0.6389 Remote Similarity NPD5167 Approved
0.6386 Remote Similarity NPD6923 Approved
0.6386 Remote Similarity NPD3698 Phase 2
0.6386 Remote Similarity NPD6922 Approved
0.6383 Remote Similarity NPD5208 Approved
0.6364 Remote Similarity NPD287 Approved
0.6364 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6354 Remote Similarity NPD8035 Phase 2
0.6354 Remote Similarity NPD8034 Phase 2
0.6339 Remote Similarity NPD6015 Approved
0.6339 Remote Similarity NPD6016 Approved

  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