Structure

Physi-Chem Properties

Molecular Weight:  150.07
Volume:  162.698
LogP:  1.975
LogD:  2.027
LogS:  -1.588
# Rotatable Bonds:  2
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.498
Synthetic Accessibility Score:  2.166
Fsp3:  0.111
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.45
MDCK Permeability:  2.600467632873915e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.957
30% Bioavailability (F30%):  0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.053
Plasma Protein Binding (PPB):  91.71810913085938%
Volume Distribution (VD):  0.593
Pgp-substrate:  4.389400959014893%

ADMET: Metabolism

CYP1A2-inhibitor:  0.719
CYP1A2-substrate:  0.644
CYP2C19-inhibitor:  0.283
CYP2C19-substrate:  0.088
CYP2C9-inhibitor:  0.271
CYP2C9-substrate:  0.836
CYP2D6-inhibitor:  0.729
CYP2D6-substrate:  0.879
CYP3A4-inhibitor:  0.138
CYP3A4-substrate:  0.228

ADMET: Excretion

Clearance (CL):  18.398
Half-life (T1/2):  0.918

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.046
Drug-inuced Liver Injury (DILI):  0.036
AMES Toxicity:  0.467
Rat Oral Acute Toxicity:  0.645
Maximum Recommended Daily Dose:  0.095
Skin Sensitization:  0.935
Carcinogencity:  0.719
Eye Corrosion:  0.794
Eye Irritation:  0.983
Respiratory Toxicity:  0.274

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC109955

Natural Product ID:  NPC109955
Common Name*:   Hydroxychavicol
IUPAC Name:   4-prop-2-enylbenzene-1,2-diol
Synonyms:   Hydroxychavicol
Standard InCHIKey:  FHEHIXJLCWUPCZ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H10O2/c1-2-3-7-4-5-8(10)9(11)6-7/h2,4-6,10-11H,1,3H2
SMILES:  C=CCc1ccc(c(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL111134
PubChem CID:   70775
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0001286] Benzenediols
          • [CHEMONTID:0000135] Catechols

*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
NPO26872 Piper betle Species Piperaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(98)00208-8]
NPO31092 Tupistra chinensis Species Asparagaceae Eukaryota n.a. n.a. n.a. PMID[12608845]
NPO3545 Dracaena draco Species Asparagaceae Eukaryota bark n.a. n.a. PMID[12828464]
NPO26872 Piper betle Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[12951092]
NPO26094 Stolonica socialis Species Styelidae Eukaryota n.a. At a depth between 3 and 15 m in Las Lajas (Cdiz, Spain) (3606'11'' N, 525'47'' W) 2003-SEP PMID[20014800]
NPO6648 Piper retrofractum Species Piperaceae Eukaryota Fruits n.a. n.a. PMID[23506561]
NPO22437 Eurya japonica Species Pentaphylacaceae Eukaryota n.a. n.a. n.a. PMID[23540981]
NPO11313 Juniperus formosana Species Cupressaceae Eukaryota n.a. leaf n.a. PMID[24273878]
NPO11313 Juniperus formosana Species Cupressaceae Eukaryota n.a. fruit n.a. PMID[24273878]
NPO6648 Piper retrofractum Species Piperaceae Eukaryota leaves n.a. n.a. PMID[25127165]
NPO3545 Dracaena draco Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26872 Piper betle Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22437 Eurya japonica Species Pentaphylacaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19964 Stephania sasakii Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31092 Tupistra chinensis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19964 Stephania sasakii Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3545 Dracaena draco Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17951 Styrax japonicus Species Styracaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26872 Piper betle Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22437 Eurya japonica Species Pentaphylacaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6648 Piper retrofractum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26195 Tephrosia crassifolia Species Geometridae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26872 Piper betle Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3545 Dracaena draco Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11320 Benkara malabarica Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26094 Stolonica socialis Species Styelidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20138 Gasterosteus aculeatus Species Gasterosteidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20380 Tanacetum balsamitoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22437 Eurya japonica Species Pentaphylacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11313 Juniperus formosana Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20644 Mucuna urens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6648 Piper retrofractum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28240 0tholaena lemmonii Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8482 Piper marginatum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26872 Piper betle Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21781 Eucalyptus kitsoni Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20020 Murdannia triquetra Species Commelinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21031 Dracocephalum moldavica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19964 Stephania sasakii Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15900 Diaphus coeruleus Species Myctophidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10722 Viburnum furcatum Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17951 Styrax japonicus Species Styracaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25742 Rhinella icterica Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20834 Artemisia pedemontana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10188 Verbascum spinosum Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8512 Helichrysum dendroideum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3545 Dracaena draco Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20966 Phlomis nissolii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21277 Eucalyptus rubida Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26195 Tephrosia crassifolia Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21598 Hypselodoris porterae Species Chromodorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22630 Calea cuneifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21531 Pseudocyphellaria aurata Species Lobariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28938 Artemisia coerulescens Species Asteraceae 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
NPT521 Cell Line RBL-2H3 Rattus norvegicus IC50 > 100000.0 nM PMID[466167]
NPT521 Cell Line RBL-2H3 Rattus norvegicus Inhibition = 17.0 % PMID[466167]
NPT1460 Cell Line L929 Mus musculus Survival = 96.2 % PMID[466169]
NPT1460 Cell Line L929 Mus musculus Survival = 96.5 % PMID[466169]
NPT1460 Cell Line L929 Mus musculus Survival = 75.7 % PMID[466169]
NPT1460 Cell Line L929 Mus musculus Survival = 94.2 % PMID[466169]
NPT1460 Cell Line L929 Mus musculus Survival = 92.2 % PMID[466169]
NPT1460 Cell Line L929 Mus musculus Survival = 82.9 % PMID[466169]
NPT1460 Cell Line L929 Mus musculus Survival = 89.1 % PMID[466169]
NPT1460 Cell Line L929 Mus musculus Survival = 88.3 % PMID[466169]
NPT1460 Cell Line L929 Mus musculus Survival = 85.4 % PMID[466169]
NPT1460 Cell Line L929 Mus musculus Activity = 6.0 % PMID[466169]
NPT4162 Cell Line NUGC Homo sapiens Inhibition = 96.0 % PMID[466170]
NPT165 Cell Line HeLa Homo sapiens IC50 = 83000.0 nM PMID[466174]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 55000.0 nM PMID[466174]
NPT60 Individual Protein Lysosomal alpha-glucosidase Homo sapiens Inhibition = 9.08 % PMID[466175]
NPT65 Cell Line HepG2 Homo sapiens GI = 29.3 % PMID[466176]
NPT65 Cell Line HepG2 Homo sapiens GI = 27.2 % PMID[466176]
NPT83 Cell Line MCF7 Homo sapiens GI = 44.1 % PMID[466176]
NPT83 Cell Line MCF7 Homo sapiens GI = 36.9 % PMID[466176]
NPT116 Cell Line HL-60 Homo sapiens Activity = 42.0 % PMID[466176]
NPT116 Cell Line HL-60 Homo sapiens Activity = 26.0 % PMID[466176]
NPT116 Cell Line HL-60 Homo sapiens Activity = 22.0 % PMID[466176]
NPT116 Cell Line HL-60 Homo sapiens Activity = 17.0 % PMID[466176]
NPT136 Cell Line SK-N-SH Homo sapiens IC50 > 30000.0 nM PMID[466176]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 30000.0 nM PMID[466176]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 30000.0 nM PMID[466176]
NPT136 Cell Line SK-N-SH Homo sapiens GI = 71.7 % PMID[466176]
NPT136 Cell Line SK-N-SH Homo sapiens GI = 34.2 % PMID[466176]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 4800.0 nM PMID[466178]
NPT32 Organism Mus musculus Mus musculus IC50 = 15000.0 nM PMID[466168]
NPT1593 Tissue Liver Rattus norvegicus Activity = 32.0 % PMID[466169]
NPT1593 Tissue Liver Rattus norvegicus Activity = 48.0 % PMID[466169]
NPT1593 Tissue Liver Rattus norvegicus Activity = 86.0 % PMID[466169]
NPT1593 Tissue Liver Rattus norvegicus Activity = 87.0 % PMID[466169]
NPT878 Organism Streptococcus mutans Streptococcus mutans MIC = 250.0 ug.mL-1 PMID[466172]
NPT1531 Organism Enterococcus faecium Enterococcus faecium MIC = 250.0 ug.mL-1 PMID[466172]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MIC = 250.0 ug.mL-1 PMID[466172]
NPT1172 Organism Streptococcus sanguinis Streptococcus sanguinis MIC = 125.0 ug.mL-1 PMID[466172]
NPT1129 Organism Actinomyces viscosus Actinomyces viscosus MIC = 250.0 ug.mL-1 PMID[466172]
NPT1655 Organism Actinobacillus actinomycetemcomitans Aggregatibacter actinomycetemcomitans MIC = 250.0 ug.mL-1 PMID[466172]
NPT1128 Organism Prevotella intermedia Prevotella intermedia MIC = 125.0 ug.mL-1 PMID[466172]
NPT1484 Organism Fusobacterium nucleatum Fusobacterium nucleatum MIC = 125.0 ug.mL-1 PMID[466172]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC = 62.5 ug.mL-1 PMID[466172]
NPT878 Organism Streptococcus mutans Streptococcus mutans MBC = 500.0 ug ml-1 PMID[466172]
NPT1531 Organism Enterococcus faecium Enterococcus faecium MBC = 500.0 ug ml-1 PMID[466172]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MBC = 250.0 ug ml-1 PMID[466172]
NPT1172 Organism Streptococcus sanguinis Streptococcus sanguinis MBC = 125.0 ug ml-1 PMID[466172]
NPT1129 Organism Actinomyces viscosus Actinomyces viscosus MBC = 500.0 ug ml-1 PMID[466172]
NPT1655 Organism Actinobacillus actinomycetemcomitans Aggregatibacter actinomycetemcomitans MBC = 500.0 ug ml-1 PMID[466172]
NPT1128 Organism Prevotella intermedia Prevotella intermedia MBC = 125.0 ug ml-1 PMID[466172]
NPT1484 Organism Fusobacterium nucleatum Fusobacterium nucleatum MBC = 125.0 ug ml-1 PMID[466172]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MBC = 62.5 ug ml-1 PMID[466172]
NPT878 Organism Streptococcus mutans Streptococcus mutans logMIC = 3.0 n.a. PMID[466172]
NPT878 Organism Streptococcus mutans Streptococcus mutans log10cfu > 50.0 n.a. PMID[466172]
NPT1129 Organism Actinomyces viscosus Actinomyces viscosus PAE = 4.0 hr PMID[466172]
NPT878 Organism Streptococcus mutans Streptococcus mutans PAE = 6.0 hr PMID[466172]
NPT1129 Organism Actinomyces viscosus Actinomyces viscosus PAE = 7.0 hr PMID[466172]
NPT878 Organism Streptococcus mutans Streptococcus mutans PAE = 3.5 hr PMID[466172]
NPT878 Organism Streptococcus mutans Streptococcus mutans IC50 = 500.0 ug.mL-1 PMID[466172]
NPT1129 Organism Actinomyces viscosus Actinomyces viscosus IC50 = 500.0 ug.mL-1 PMID[466172]
NPT1129 Organism Actinomyces viscosus Actinomyces viscosus IC50 = 1000.0 ug.mL-1 PMID[466172]
NPT1084 Subcellular Liver microsomes Rattus norvegicus Inhibition = 15.0 % PMID[466172]
NPT530 Organism Caenorhabditis elegans Caenorhabditis elegans MEC = 300.0 ug ml-1 PMID[466173]
NPT35 Others n.a. Activity = 2.55 uM PMID[466175]
NPT35 Others n.a. Activity = 16.26 uM PMID[466175]
NPT35 Others n.a. Activity = 1.55 uM PMID[466175]
NPT35 Others n.a. Activity = 22.77 uM PMID[466175]
NPT35 Others n.a. Activity = 20.48 % PMID[466175]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI = 42.8 % PMID[466176]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI = 41.7 % PMID[466176]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI = 92.4 % PMID[466176]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI = 88.8 % PMID[466176]
NPT610 Others Molecular identity unknown Activity = 6.0 % PMID[466176]
NPT610 Others Molecular identity unknown Activity = 67.0 % PMID[466176]
NPT610 Others Molecular identity unknown Activity = 27.0 % PMID[466176]
NPT610 Others Molecular identity unknown Activity = 10.0 % PMID[466176]
NPT610 Others Molecular identity unknown Activity = 22.0 % PMID[466176]
NPT610 Others Molecular identity unknown Activity = 61.0 % PMID[466176]
NPT610 Others Molecular identity unknown Activity = 17.0 % PMID[466176]
NPT610 Others Molecular identity unknown Activity = 9.0 % PMID[466176]
NPT610 Others Molecular identity unknown Activity = 54.0 % PMID[466176]
NPT610 Others Molecular identity unknown Activity = 37.0 % PMID[466176]
NPT610 Others Molecular identity unknown Activity = 8.0 % PMID[466176]
NPT610 Others Molecular identity unknown Activity = 57.0 % PMID[466176]
NPT610 Others Molecular identity unknown Activity = 35.0 % PMID[466176]
NPT610 Others Molecular identity unknown Activity = 5.0 % PMID[466176]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 50000.0 nM PMID[466176]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 30000.0 nM PMID[466176]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 3000.0 nM PMID[466176]
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens Ratio IC50 = 1.84 n.a. PMID[466177]
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 16700.0 nM PMID[466177]

☑ 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 NPC109955 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
0.9681 High Similarity NPC110764
0.9579 High Similarity NPC196479
0.9565 High Similarity NPC107522
0.9479 High Similarity NPC12278
0.9479 High Similarity NPC471511
0.9479 High Similarity NPC120719
0.9468 High Similarity NPC131587
0.9381 High Similarity NPC239291
0.9368 High Similarity NPC223393
0.9286 High Similarity NPC477814
0.91 High Similarity NPC233835
0.9082 High Similarity NPC79672
0.9082 High Similarity NPC52087
0.901 High Similarity NPC62258
0.901 High Similarity NPC254833
0.901 High Similarity NPC55617
0.901 High Similarity NPC228343
0.898 High Similarity NPC477802
0.898 High Similarity NPC477801
0.8947 High Similarity NPC274678
0.8922 High Similarity NPC120982
0.8922 High Similarity NPC174096
0.8922 High Similarity NPC79793
0.8922 High Similarity NPC222084
0.8922 High Similarity NPC226401
0.8922 High Similarity NPC147634
0.8913 High Similarity NPC27974
0.89 High Similarity NPC1786
0.89 High Similarity NPC294902
0.89 High Similarity NPC19149
0.89 High Similarity NPC1075
0.8835 High Similarity NPC257124
0.8835 High Similarity NPC297657
0.8835 High Similarity NPC187583
0.8835 High Similarity NPC156840
0.8835 High Similarity NPC257430
0.8835 High Similarity NPC8547
0.8835 High Similarity NPC179002
0.8835 High Similarity NPC268032
0.8835 High Similarity NPC173746
0.8812 High Similarity NPC176527
0.8804 High Similarity NPC23167
0.8791 High Similarity NPC175313
0.875 High Similarity NPC146422
0.8725 High Similarity NPC58427
0.8725 High Similarity NPC34864
0.8725 High Similarity NPC114392
0.8725 High Similarity NPC105727
0.8723 High Similarity NPC300017
0.8723 High Similarity NPC192
0.871 High Similarity NPC25493
0.871 High Similarity NPC113460
0.8696 High Similarity NPC197783
0.8681 High Similarity NPC265146
0.8667 High Similarity NPC471485
0.8667 High Similarity NPC264558
0.8667 High Similarity NPC148969
0.866 High Similarity NPC202986
0.8641 High Similarity NPC7097
0.8641 High Similarity NPC246358
0.8641 High Similarity NPC233731
0.8641 High Similarity NPC36108
0.8632 High Similarity NPC304541
0.8632 High Similarity NPC45040
0.8617 High Similarity NPC123273
0.8617 High Similarity NPC177420
0.8617 High Similarity NPC242240
0.8617 High Similarity NPC258219
0.8617 High Similarity NPC280347
0.8617 High Similarity NPC318325
0.8587 High Similarity NPC150837
0.8587 High Similarity NPC248817
0.8585 High Similarity NPC142599
0.8585 High Similarity NPC120280
0.8571 High Similarity NPC32674
0.8542 High Similarity NPC325292
0.8542 High Similarity NPC147284
0.8542 High Similarity NPC55903
0.8542 High Similarity NPC138117
0.8542 High Similarity NPC210497
0.8542 High Similarity NPC162314
0.8542 High Similarity NPC3358
0.8542 High Similarity NPC94139
0.8542 High Similarity NPC306884
0.8526 High Similarity NPC312304
0.8526 High Similarity NPC55561
0.8511 High Similarity NPC104216
0.8505 High Similarity NPC4665
0.8495 Intermediate Similarity NPC155393
0.8478 Intermediate Similarity NPC124436
0.8476 Intermediate Similarity NPC139617
0.8476 Intermediate Similarity NPC78918
0.8476 Intermediate Similarity NPC195873
0.8476 Intermediate Similarity NPC226250
0.8462 Intermediate Similarity NPC71266
0.8454 Intermediate Similarity NPC316301
0.8454 Intermediate Similarity NPC151715
0.8454 Intermediate Similarity NPC128062
0.8454 Intermediate Similarity NPC245187
0.8454 Intermediate Similarity NPC76938
0.8454 Intermediate Similarity NPC27323
0.8438 Intermediate Similarity NPC231150
0.8438 Intermediate Similarity NPC155908
0.8426 Intermediate Similarity NPC277394
0.8426 Intermediate Similarity NPC221049
0.8426 Intermediate Similarity NPC299252
0.8426 Intermediate Similarity NPC61062
0.8404 Intermediate Similarity NPC184169
0.8404 Intermediate Similarity NPC307235
0.8404 Intermediate Similarity NPC407
0.8396 Intermediate Similarity NPC51698
0.8396 Intermediate Similarity NPC471179
0.8396 Intermediate Similarity NPC131530
0.8384 Intermediate Similarity NPC152097
0.8384 Intermediate Similarity NPC474073
0.8367 Intermediate Similarity NPC32714
0.8367 Intermediate Similarity NPC26244
0.8367 Intermediate Similarity NPC313650
0.8351 Intermediate Similarity NPC29373
0.8349 Intermediate Similarity NPC200988
0.8349 Intermediate Similarity NPC86947
0.8349 Intermediate Similarity NPC145023
0.8349 Intermediate Similarity NPC293619
0.8349 Intermediate Similarity NPC164386
0.8349 Intermediate Similarity NPC150919
0.8349 Intermediate Similarity NPC278652
0.8349 Intermediate Similarity NPC175799
0.8349 Intermediate Similarity NPC610
0.8333 Intermediate Similarity NPC30506
0.8333 Intermediate Similarity NPC300478
0.8333 Intermediate Similarity NPC472893
0.8318 Intermediate Similarity NPC95381
0.8316 Intermediate Similarity NPC19680
0.8302 Intermediate Similarity NPC280382
0.83 Intermediate Similarity NPC260775
0.83 Intermediate Similarity NPC92730
0.8283 Intermediate Similarity NPC132271
0.8283 Intermediate Similarity NPC82664
0.8283 Intermediate Similarity NPC216520
0.8283 Intermediate Similarity NPC473388
0.8283 Intermediate Similarity NPC312132
0.8283 Intermediate Similarity NPC292730
0.8283 Intermediate Similarity NPC259512
0.8273 Intermediate Similarity NPC203124
0.8273 Intermediate Similarity NPC86198
0.8273 Intermediate Similarity NPC255675
0.8273 Intermediate Similarity NPC63126
0.8273 Intermediate Similarity NPC144343
0.8273 Intermediate Similarity NPC85276
0.8273 Intermediate Similarity NPC309434
0.8273 Intermediate Similarity NPC470626
0.8247 Intermediate Similarity NPC204210
0.8247 Intermediate Similarity NPC270547
0.8242 Intermediate Similarity NPC204932
0.8241 Intermediate Similarity NPC328593
0.8241 Intermediate Similarity NPC217472
0.8241 Intermediate Similarity NPC261453
0.8241 Intermediate Similarity NPC33749
0.8229 Intermediate Similarity NPC98772
0.8218 Intermediate Similarity NPC10588
0.8218 Intermediate Similarity NPC166761
0.8218 Intermediate Similarity NPC275053
0.8218 Intermediate Similarity NPC130103
0.8218 Intermediate Similarity NPC72729
0.8218 Intermediate Similarity NPC174911
0.8218 Intermediate Similarity NPC248396
0.8218 Intermediate Similarity NPC130756
0.8218 Intermediate Similarity NPC248573
0.8218 Intermediate Similarity NPC211885
0.8218 Intermediate Similarity NPC12931
0.8218 Intermediate Similarity NPC294741
0.8218 Intermediate Similarity NPC129373
0.8218 Intermediate Similarity NPC48730
0.8218 Intermediate Similarity NPC161571
0.8218 Intermediate Similarity NPC70677
0.8208 Intermediate Similarity NPC137685
0.82 Intermediate Similarity NPC156313
0.82 Intermediate Similarity NPC475078
0.82 Intermediate Similarity NPC77492
0.82 Intermediate Similarity NPC260000
0.82 Intermediate Similarity NPC107619
0.82 Intermediate Similarity NPC6597
0.82 Intermediate Similarity NPC225464
0.82 Intermediate Similarity NPC79241
0.8198 Intermediate Similarity NPC109371
0.8198 Intermediate Similarity NPC217174
0.8198 Intermediate Similarity NPC310338
0.8198 Intermediate Similarity NPC470214
0.8198 Intermediate Similarity NPC20674
0.8198 Intermediate Similarity NPC263386
0.8198 Intermediate Similarity NPC281298
0.8198 Intermediate Similarity NPC470215
0.8198 Intermediate Similarity NPC299406
0.8198 Intermediate Similarity NPC181969
0.8198 Intermediate Similarity NPC70084
0.8198 Intermediate Similarity NPC477803
0.8198 Intermediate Similarity NPC320987
0.8198 Intermediate Similarity NPC268572
0.8198 Intermediate Similarity NPC311595
0.8198 Intermediate Similarity NPC141791

  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 NPC109955 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
0.901 High Similarity NPD3021 Approved
0.901 High Similarity NPD3022 Approved
0.8835 High Similarity NPD228 Approved
0.875 High Similarity NPD9377 Approved
0.875 High Similarity NPD9379 Approved
0.8478 Intermediate Similarity NPD111 Approved
0.8454 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.8454 Intermediate Similarity NPD2933 Approved
0.8454 Intermediate Similarity NPD2934 Approved
0.8381 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.8367 Intermediate Similarity NPD2859 Approved
0.8367 Intermediate Similarity NPD2860 Approved
0.8367 Intermediate Similarity NPD844 Approved
0.83 Intermediate Similarity NPD3020 Approved
0.8283 Intermediate Similarity NPD288 Approved
0.8218 Intermediate Similarity NPD1242 Phase 1
0.8218 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD9381 Approved
0.8125 Intermediate Similarity NPD9384 Approved
0.7961 Intermediate Similarity NPD940 Approved
0.7961 Intermediate Similarity NPD846 Approved
0.7845 Intermediate Similarity NPD9622 Approved
0.7822 Intermediate Similarity NPD1809 Phase 2
0.78 Intermediate Similarity NPD845 Approved
0.7778 Intermediate Similarity NPD5311 Approved
0.7778 Intermediate Similarity NPD5310 Approved
0.7778 Intermediate Similarity NPD9634 Clinical (unspecified phase)
0.7712 Intermediate Similarity NPD3053 Approved
0.7712 Intermediate Similarity NPD3055 Approved
0.7664 Intermediate Similarity NPD1445 Approved
0.7664 Intermediate Similarity NPD1444 Approved
0.7653 Intermediate Similarity NPD9094 Approved
0.7647 Intermediate Similarity NPD257 Approved
0.7647 Intermediate Similarity NPD9620 Approved
0.7647 Intermediate Similarity NPD9621 Approved
0.7647 Intermediate Similarity NPD258 Approved
0.7647 Intermediate Similarity NPD9619 Approved
0.7642 Intermediate Similarity NPD9608 Approved
0.7642 Intermediate Similarity NPD9610 Approved
0.7607 Intermediate Similarity NPD2337 Clinical (unspecified phase)
0.7583 Intermediate Similarity NPD9569 Approved
0.7542 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7521 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5283 Phase 1
0.7473 Intermediate Similarity NPD9087 Approved
0.7459 Intermediate Similarity NPD3027 Phase 3
0.7455 Intermediate Similarity NPD4750 Phase 3
0.7455 Intermediate Similarity NPD1792 Phase 2
0.7455 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD2342 Discontinued
0.7414 Intermediate Similarity NPD1357 Approved
0.7398 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7398 Intermediate Similarity NPD598 Approved
0.7398 Intermediate Similarity NPD601 Approved
0.7398 Intermediate Similarity NPD597 Approved
0.7383 Intermediate Similarity NPD9500 Approved
0.7379 Intermediate Similarity NPD9296 Approved
0.7373 Intermediate Similarity NPD3092 Approved
0.7364 Intermediate Similarity NPD2684 Approved
0.7358 Intermediate Similarity NPD3028 Approved
0.7345 Intermediate Similarity NPD2228 Approved
0.7345 Intermediate Similarity NPD2229 Approved
0.7345 Intermediate Similarity NPD2234 Approved
0.734 Intermediate Similarity NPD9088 Approved
0.7339 Intermediate Similarity NPD1130 Approved
0.7339 Intermediate Similarity NPD1136 Approved
0.7339 Intermediate Similarity NPD1132 Approved
0.7339 Intermediate Similarity NPD2674 Phase 3
0.7339 Intermediate Similarity NPD259 Phase 1
0.7333 Intermediate Similarity NPD9273 Approved
0.7328 Intermediate Similarity NPD3091 Approved
0.7317 Intermediate Similarity NPD9537 Phase 1
0.7317 Intermediate Similarity NPD9536 Phase 1
0.7311 Intermediate Similarity NPD9269 Phase 2
0.7295 Intermediate Similarity NPD9494 Approved
0.7281 Intermediate Similarity NPD9614 Approved
0.7281 Intermediate Similarity NPD9618 Approved
0.728 Intermediate Similarity NPD1613 Approved
0.728 Intermediate Similarity NPD3061 Approved
0.728 Intermediate Similarity NPD826 Approved
0.728 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.728 Intermediate Similarity NPD825 Approved
0.728 Intermediate Similarity NPD3059 Approved
0.728 Intermediate Similarity NPD943 Approved
0.728 Intermediate Similarity NPD1558 Phase 1
0.728 Intermediate Similarity NPD3062 Approved
0.7257 Intermediate Similarity NPD7635 Approved
0.7234 Intermediate Similarity NPD9294 Approved
0.7222 Intermediate Similarity NPD555 Phase 2
0.7222 Intermediate Similarity NPD275 Approved
0.7222 Intermediate Similarity NPD274 Approved
0.7217 Intermediate Similarity NPD6671 Approved
0.7203 Intermediate Similarity NPD2932 Approved
0.7203 Intermediate Similarity NPD4059 Approved
0.7203 Intermediate Similarity NPD2286 Discontinued
0.7203 Intermediate Similarity NPD3019 Approved
0.7182 Intermediate Similarity NPD968 Approved
0.7165 Intermediate Similarity NPD817 Approved
0.7165 Intermediate Similarity NPD823 Approved
0.7165 Intermediate Similarity NPD5314 Approved
0.7143 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3620 Phase 2
0.7131 Intermediate Similarity NPD3094 Phase 2
0.713 Intermediate Similarity NPD1791 Approved
0.713 Intermediate Similarity NPD1793 Approved
0.712 Intermediate Similarity NPD3144 Approved
0.712 Intermediate Similarity NPD3145 Approved
0.7119 Intermediate Similarity NPD4093 Discontinued
0.7117 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD290 Approved
0.7105 Intermediate Similarity NPD7843 Approved
0.7094 Intermediate Similarity NPD9615 Approved
0.7094 Intermediate Similarity NPD9613 Approved
0.7094 Intermediate Similarity NPD9616 Approved
0.7069 Intermediate Similarity NPD255 Approved
0.7069 Intermediate Similarity NPD7157 Approved
0.7069 Intermediate Similarity NPD256 Approved
0.7059 Intermediate Similarity NPD1751 Approved
0.7054 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD9089 Approved
0.7034 Intermediate Similarity NPD316 Approved
0.7018 Intermediate Similarity NPD6124 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD9568 Approved
0.7 Intermediate Similarity NPD9570 Approved
0.7 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.6983 Remote Similarity NPD475 Phase 2
0.6975 Remote Similarity NPD9268 Approved
0.6967 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6957 Remote Similarity NPD821 Approved
0.6953 Remote Similarity NPD230 Phase 1
0.6949 Remote Similarity NPD317 Approved
0.6949 Remote Similarity NPD5536 Phase 2
0.6949 Remote Similarity NPD856 Approved
0.6949 Remote Similarity NPD16 Approved
0.6949 Remote Similarity NPD318 Approved
0.6947 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6947 Remote Similarity NPD7266 Discontinued
0.6939 Remote Similarity NPD9093 Approved
0.6917 Remote Similarity NPD3095 Discontinued
0.6917 Remote Similarity NPD4626 Approved
0.6897 Remote Similarity NPD7159 Clinical (unspecified phase)
0.6891 Remote Similarity NPD1548 Phase 1
0.6891 Remote Similarity NPD2226 Clinical (unspecified phase)
0.6855 Remote Similarity NPD4339 Clinical (unspecified phase)
0.6852 Remote Similarity NPD9495 Approved
0.6838 Remote Similarity NPD1476 Clinical (unspecified phase)
0.6803 Remote Similarity NPD3705 Approved
0.6803 Remote Similarity NPD5350 Clinical (unspecified phase)
0.6803 Remote Similarity NPD5351 Clinical (unspecified phase)
0.6803 Remote Similarity NPD1610 Phase 2
0.6803 Remote Similarity NPD1201 Approved
0.68 Remote Similarity NPD6584 Phase 3
0.6791 Remote Similarity NPD8166 Discontinued
0.678 Remote Similarity NPD709 Approved
0.6777 Remote Similarity NPD5238 Clinical (unspecified phase)
0.6777 Remote Similarity NPD4589 Approved
0.6754 Remote Similarity NPD74 Approved
0.6754 Remote Similarity NPD9266 Approved
0.675 Remote Similarity NPD5303 Approved
0.675 Remote Similarity NPD9545 Approved
0.675 Remote Similarity NPD5304 Approved
0.6746 Remote Similarity NPD2861 Phase 2
0.6746 Remote Similarity NPD5736 Approved
0.6744 Remote Similarity NPD4060 Phase 1
0.6731 Remote Similarity NPD9295 Approved
0.6696 Remote Similarity NPD5451 Approved
0.6696 Remote Similarity NPD9244 Approved
0.6695 Remote Similarity NPD497 Approved
0.6694 Remote Similarity NPD2982 Phase 2
0.6694 Remote Similarity NPD1755 Approved
0.6694 Remote Similarity NPD2983 Phase 2
0.6691 Remote Similarity NPD3845 Phase 1
0.6691 Remote Similarity NPD2422 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9267 Approved
0.6667 Remote Similarity NPD9264 Approved
0.6667 Remote Similarity NPD291 Approved
0.6667 Remote Similarity NPD1358 Approved
0.6667 Remote Similarity NPD9263 Approved
0.6667 Remote Similarity NPD2195 Approved
0.6667 Remote Similarity NPD9073 Approved
0.6667 Remote Similarity NPD2194 Approved
0.6667 Remote Similarity NPD422 Phase 1
0.6667 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1535 Discovery
0.6642 Remote Similarity NPD2420 Approved
0.6642 Remote Similarity NPD1511 Approved
0.6642 Remote Similarity NPD2421 Approved
0.6641 Remote Similarity NPD7095 Approved
0.664 Remote Similarity NPD1283 Approved
0.6639 Remote Similarity NPD2667 Approved
0.6639 Remote Similarity NPD6516 Phase 2
0.6639 Remote Similarity NPD2668 Approved
0.6639 Remote Similarity NPD5846 Approved
0.6618 Remote Similarity NPD6190 Approved
0.6618 Remote Similarity NPD302 Approved
0.6614 Remote Similarity NPD3636 Approved
0.6614 Remote Similarity NPD3018 Phase 2
0.6614 Remote Similarity NPD3637 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