Structure

Physi-Chem Properties

Molecular Weight:  196.07
Volume:  197.575
LogP:  2.515
LogD:  1.85
LogS:  -2.129
# Rotatable Bonds:  2
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.668
Synthetic Accessibility Score:  2.233
Fsp3:  0.3
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.677
MDCK Permeability:  1.4014476619195193e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.042
30% Bioavailability (F30%):  0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.368
Plasma Protein Binding (PPB):  94.87581634521484%
Volume Distribution (VD):  0.541
Pgp-substrate:  4.8840413093566895%

ADMET: Metabolism

CYP1A2-inhibitor:  0.954
CYP1A2-substrate:  0.939
CYP2C19-inhibitor:  0.225
CYP2C19-substrate:  0.339
CYP2C9-inhibitor:  0.26
CYP2C9-substrate:  0.726
CYP2D6-inhibitor:  0.294
CYP2D6-substrate:  0.464
CYP3A4-inhibitor:  0.255
CYP3A4-substrate:  0.233

ADMET: Excretion

Clearance (CL):  14.35
Half-life (T1/2):  0.852

ADMET: Toxicity

hERG Blockers:  0.011
Human Hepatotoxicity (H-HT):  0.087
Drug-inuced Liver Injury (DILI):  0.504
AMES Toxicity:  0.18
Rat Oral Acute Toxicity:  0.056
Maximum Recommended Daily Dose:  0.635
Skin Sensitization:  0.65
Carcinogencity:  0.042
Eye Corrosion:  0.153
Eye Irritation:  0.962
Respiratory Toxicity:  0.397

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  Natural Product: NPC158481

Natural Product ID:  NPC158481
Common Name*:   Atraric Acid
IUPAC Name:   methyl 2,4-dihydroxy-3,6-dimethylbenzoate
Synonyms:   Atraric Acid; Methyl Beta-Orcinolcarboxylate; Methyl-Beta-Orcinol Carboxylate
Standard InCHIKey:  UUQHKWMIDYRWHH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H12O4/c1-5-4-7(11)6(2)9(12)8(5)10(13)14-3/h4,11-12H,1-3H3
SMILES:  COC(=O)c1c(C)cc(c(c1O)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL508287
PubChem CID:   78435
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000176] Benzoic acids and derivatives
          • [CHEMONTID:0001350] Benzoic acid esters
            • [CHEMONTID:0004701] p-Hydroxybenzoic acid esters
              • [CHEMONTID:0004702] p-Hydroxybenzoic acid alkyl esters

*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
NPO27 Gentiana dahurica Species Gentianaceae Eukaryota n.a. root n.a. PMID[22233034]
NPO40360 Stereocaulon paschale Species Stereocaulaceae Eukaryota n.a. n.a. n.a. PMID[28079378]
NPO3729 Cetraria islandica Species Parmeliaceae Eukaryota n.a. n.a. n.a. PMID[7561895]
NPO25691 Piper decurrens Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[8991948]
NPO1921 Alectoria vivens Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25809 Helleborus niger Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14975 Adenanthera pavonina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22553 Thalictrum fendleri Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27 Gentiana dahurica Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22230 Rhodiola crenulata Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21779 Umbilicaria hypococcinea Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25424 Putterlickia verrucosa Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20890 Anemone begoniifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22230 Rhodiola crenulata Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27 Gentiana dahurica Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22553 Thalictrum fendleri Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25809 Helleborus niger Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7908 Lethariella zahlbruckneri Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21779 Umbilicaria hypococcinea Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1921 Alectoria vivens Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11504 Lethariella cladonioides Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14975 Adenanthera pavonina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7908 Lethariella zahlbruckneri Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22230 Rhodiola crenulata Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11504 Lethariella cladonioides Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21779 Umbilicaria hypococcinea Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27 Gentiana dahurica Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27 Gentiana dahurica Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22230 Rhodiola crenulata Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25435 Euphorbia pulcherrima Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25809 Helleborus niger Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22230 Rhodiola crenulata Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24503 Clematis songarica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4633 Calypogeia integristipula Species Calypogeiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22010 Dasyscyphus nidulus Species Hyaloscyphaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6513 Vernonia condensata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20890 Anemone begoniifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27 Gentiana dahurica Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20804.1 Acer palmatum subsp. amoenum Subspecies Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2777 Cirsium brevistylum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24766 Lecidea macrocarpa Species Lecideaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17684 Teucrium sandrasicum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3729 Cetraria islandica Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5786 Desmodium oxyphyllum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21779 Umbilicaria hypococcinea Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23615 Ixodes ricinus Species Ixodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25424 Putterlickia verrucosa Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22172 Cosmos hybridus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21406 Pteris polypodioides Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7908 Lethariella zahlbruckneri Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5926 Panisea uniflora Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14975 Adenanthera pavonina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19958 Helichrysum tomentosulum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24375 Micrococcus luteus Species Micrococcaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO25691 Piper decurrens Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25511 Streptomyces ghanaensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17140 Clonostachys rosea f. catenulata Species Bionectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22694 Croton plumieri Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO196 Aniba lancifolia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20699 Melampodium rosei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11504 Lethariella cladonioides Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25524 Sideritis pumila Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25022 Baccharis incarum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22616 Pourthiaea lucida n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO22553 Thalictrum fendleri Species Ranunculaceae 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
NPT1195 Cell Line PMNL IC50 > 60000.0 nM PMID[476259]
NPT941 Cell Line HaCaT Homo sapiens IC50 > 5000.0 nM PMID[476260]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 89125.1 nM PMID[476262]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 12589.3 nM PMID[476262]
NPT160 Individual Protein TAR DNA-binding protein 43 Homo sapiens Potency n.a. 316.2 nM PMID[476262]
NPT466 Cell Line U-937 Homo sapiens Activity = 125.0 % PMID[476266]
NPT466 Cell Line U-937 Homo sapiens Activity = 116.0 % PMID[476266]
NPT466 Cell Line U-937 Homo sapiens Activity = 118.0 % PMID[476266]
NPT466 Cell Line U-937 Homo sapiens Activity = 112.0 % PMID[476266]
NPT466 Cell Line U-937 Homo sapiens Inhibition = 0.0 % PMID[476266]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 21872.4 nM PubChem BioAssay data set
NPT965 Organism Amaranthus hypochondriacus Amaranthus hypochondriacus IC50 = 320000.0 nM PMID[476257]
NPT117 Organism Echinochloa crus-galli Echinochloa crus-galli IC50 = 610000.0 nM PMID[476257]
NPT965 Organism Amaranthus hypochondriacus Amaranthus hypochondriacus IC50 = 760000.0 nM PMID[476257]
NPT117 Organism Echinochloa crus-galli Echinochloa crus-galli IC50 = 1100000.0 nM PMID[476257]
NPT2792 Organism Penicillium digitatum Penicillium digitatum IZ = 29.0 mm PMID[476258]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IZ = 18.0 mm PMID[476258]
NPT79 Organism Bacillus subtilis Bacillus subtilis IZ = 17.0 mm PMID[476258]
NPT4789 Organism Escherichia coli B Escherichia coli B IZ = 15.0 mm PMID[476258]
NPT2 Others Unspecified IC50 > 200000.0 nM PMID[476259]
NPT2 Others Unspecified Activity = 1.43 umol PMID[476259]
NPT1 Others Radical scavenging activity Activity = 5.95 /M/s PMID[476259]
NPT2701 Organism Pythium debaryanum Pythium debaryanum ED50 = 56.96 ug ml-1 PMID[476263]
NPT961 Organism Pythium aphanidermatum Pythium aphanidermatum ED50 = 81.5 ug ml-1 PMID[476263]
NPT2702 Organism Fusarium udum Fusarium udum ED50 = 82.31 ug ml-1 PMID[476263]
NPT2703 Organism Rhizoctonia bataticola Rhizoctonia bataticola ED50 = 77.21 ug ml-1 PMID[476263]
NPT529 Organism Rhizoctonia solani Rhizoctonia solani ED50 = 57.5 ug ml-1 PMID[476263]
NPT722 Organism Athelia rolfsii Athelia rolfsii ED50 = 80.21 ug ml-1 PMID[476263]
NPT2701 Organism Pythium debaryanum Pythium debaryanum Inhibition = 44.0 % PMID[476263]
NPT2701 Organism Pythium debaryanum Pythium debaryanum Inhibition = 72.33 % PMID[476263]
NPT2701 Organism Pythium debaryanum Pythium debaryanum Inhibition = 89.33 % PMID[476263]
NPT961 Organism Pythium aphanidermatum Pythium aphanidermatum Inhibition = 22.33 % PMID[476263]
NPT961 Organism Pythium aphanidermatum Pythium aphanidermatum Inhibition = 50.0 % PMID[476263]
NPT961 Organism Pythium aphanidermatum Pythium aphanidermatum Inhibition = 88.3 % PMID[476263]
NPT2702 Organism Fusarium udum Fusarium udum Inhibition = 26.67 % PMID[476263]
NPT2702 Organism Fusarium udum Fusarium udum Inhibition = 50.0 % PMID[476263]
NPT2702 Organism Fusarium udum Fusarium udum Inhibition = 80.46 % PMID[476263]
NPT2703 Organism Rhizoctonia bataticola Rhizoctonia bataticola Inhibition = 28.33 % PMID[476263]
NPT2703 Organism Rhizoctonia bataticola Rhizoctonia bataticola Inhibition = 50.33 % PMID[476263]
NPT2703 Organism Rhizoctonia bataticola Rhizoctonia bataticola Inhibition = 90.34 % PMID[476263]
NPT529 Organism Rhizoctonia solani Rhizoctonia solani Inhibition = 46.0 % PMID[476263]
NPT529 Organism Rhizoctonia solani Rhizoctonia solani Inhibition = 67.0 % PMID[476263]
NPT529 Organism Rhizoctonia solani Rhizoctonia solani Inhibition = 80.33 % PMID[476263]
NPT722 Organism Athelia rolfsii Athelia rolfsii Inhibition = 33.0 % PMID[476263]
NPT722 Organism Athelia rolfsii Athelia rolfsii Inhibition = 50.0 % PMID[476263]
NPT722 Organism Athelia rolfsii Athelia rolfsii Inhibition = 74.32 % PMID[476263]
NPT21912 ORGANISM Hylobius abietis Hylobius abietis AFI = 31.0 % PMID[476264]
NPT1127 Organism Porphyromonas gingivalis Porphyromonas gingivalis MIC > 80000.0 nM PMID[476265]
NPT878 Organism Streptococcus mutans Streptococcus mutans MIC > 80000.0 nM PMID[476265]
NPT1127 Organism Porphyromonas gingivalis Porphyromonas gingivalis MBC > 80.0 uM PMID[476265]
NPT878 Organism Streptococcus mutans Streptococcus mutans MBC > 80.0 uM PMID[476265]
NPT25297 SINGLE PROTEIN Toll-like receptor 4 Homo sapiens Inhibition = 25.0 % PMID[476266]
NPT25297 SINGLE PROTEIN Toll-like receptor 4 Homo sapiens Inhibition = 36.0 % PMID[476266]
NPT25297 SINGLE PROTEIN Toll-like receptor 4 Homo sapiens Inhibition = 19.0 % PMID[476266]
NPT25297 SINGLE PROTEIN Toll-like receptor 4 Homo sapiens Inhibition = 27.0 % PMID[476266]
NPT2 Others Unspecified Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61659.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 12197.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 19493.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54482.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61130.6 nM PubChem BioAssay data set

☑ 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 NPC158481 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
0.9699 High Similarity NPC165172
0.9699 High Similarity NPC99441
0.9627 High Similarity NPC37530
0.9621 High Similarity NPC194579
0.9612 High Similarity NPC219892
0.9612 High Similarity NPC189823
0.9535 High Similarity NPC296158
0.9485 High Similarity NPC159721
0.9466 High Similarity NPC153783
0.9416 High Similarity NPC42540
0.9416 High Similarity NPC151607
0.9398 High Similarity NPC50455
0.9343 High Similarity NPC471731
0.9333 High Similarity NPC88269
0.9333 High Similarity NPC275356
0.9328 High Similarity NPC70380
0.9323 High Similarity NPC180905
0.9323 High Similarity NPC182496
0.9323 High Similarity NPC278375
0.9318 High Similarity NPC37299
0.9318 High Similarity NPC180261
0.9318 High Similarity NPC48036
0.9281 High Similarity NPC163846
0.9281 High Similarity NPC225173
0.927 High Similarity NPC471733
0.9265 High Similarity NPC168471
0.9265 High Similarity NPC472601
0.9265 High Similarity NPC472600
0.9259 High Similarity NPC212693
0.9259 High Similarity NPC191835
0.9259 High Similarity NPC94248
0.9254 High Similarity NPC235115
0.9248 High Similarity NPC175943
0.9214 High Similarity NPC53362
0.9214 High Similarity NPC166583
0.9214 High Similarity NPC125801
0.9197 High Similarity NPC472605
0.9197 High Similarity NPC472604
0.9197 High Similarity NPC472603
0.9191 High Similarity NPC139634
0.9191 High Similarity NPC105456
0.9185 High Similarity NPC135837
0.9179 High Similarity NPC290803
0.9147 High Similarity NPC201728
0.9147 High Similarity NPC262671
0.913 High Similarity NPC182255
0.913 High Similarity NPC82913
0.913 High Similarity NPC94076
0.9118 High Similarity NPC472602
0.9118 High Similarity NPC478200
0.9118 High Similarity NPC33144
0.9111 High Similarity NPC291454
0.9111 High Similarity NPC118919
0.9104 High Similarity NPC474394
0.9104 High Similarity NPC475645
0.9091 High Similarity NPC62219
0.9085 High Similarity NPC233267
0.9085 High Similarity NPC291049
0.9078 High Similarity NPC471734
0.9065 High Similarity NPC472610
0.9065 High Similarity NPC84266
0.9058 High Similarity NPC313123
0.9058 High Similarity NPC1704
0.9058 High Similarity NPC53649
0.9058 High Similarity NPC478217
0.9058 High Similarity NPC67650
0.9051 High Similarity NPC92655
0.9051 High Similarity NPC32360
0.9051 High Similarity NPC268052
0.9051 High Similarity NPC471819
0.9051 High Similarity NPC52358
0.9044 High Similarity NPC71256
0.9044 High Similarity NPC245058
0.9021 High Similarity NPC119929
0.9014 High Similarity NPC105415
0.9014 High Similarity NPC37139
0.9007 High Similarity NPC473023
0.9007 High Similarity NPC471735
0.8993 High Similarity NPC322112
0.8993 High Similarity NPC250755
0.8986 High Similarity NPC155205
0.8986 High Similarity NPC158472
0.8978 High Similarity NPC221104
0.8971 High Similarity NPC472599
0.8971 High Similarity NPC156967
0.8963 High Similarity NPC474519
0.8958 High Similarity NPC133856
0.8947 High Similarity NPC247477
0.8947 High Similarity NPC17840
0.8939 High Similarity NPC41263
0.8936 High Similarity NPC75694
0.8936 High Similarity NPC473692
0.8931 High Similarity NPC95309
0.8929 High Similarity NPC51106
0.8929 High Similarity NPC478202
0.8929 High Similarity NPC472006
0.8929 High Similarity NPC469542
0.8921 High Similarity NPC478201
0.8921 High Similarity NPC149533
0.8921 High Similarity NPC158634
0.8921 High Similarity NPC90411
0.8921 High Similarity NPC244923
0.8921 High Similarity NPC475730
0.8921 High Similarity NPC470842
0.8921 High Similarity NPC472035
0.8913 High Similarity NPC247409
0.8905 High Similarity NPC474771
0.8905 High Similarity NPC65837
0.8905 High Similarity NPC149372
0.8905 High Similarity NPC474849
0.8905 High Similarity NPC178467
0.8897 High Similarity NPC273483
0.8897 High Similarity NPC175978
0.8897 High Similarity NPC271681
0.8889 High Similarity NPC267205
0.8889 High Similarity NPC150928
0.8889 High Similarity NPC158866
0.8881 High Similarity NPC2569
0.8881 High Similarity NPC172329
0.8873 High Similarity NPC260946
0.8865 High Similarity NPC193703
0.8865 High Similarity NPC48762
0.8865 High Similarity NPC21599
0.8857 High Similarity NPC474385
0.8841 High Similarity NPC475974
0.8836 High Similarity NPC472799
0.8811 High Similarity NPC137296
0.8811 High Similarity NPC126767
0.8811 High Similarity NPC7943
0.8811 High Similarity NPC56433
0.8811 High Similarity NPC312929
0.8811 High Similarity NPC8817
0.8811 High Similarity NPC289042
0.8811 High Similarity NPC190648
0.8811 High Similarity NPC22005
0.8811 High Similarity NPC118027
0.8811 High Similarity NPC34802
0.8811 High Similarity NPC245584
0.8811 High Similarity NPC123202
0.8803 High Similarity NPC134621
0.8803 High Similarity NPC34482
0.8803 High Similarity NPC28632
0.8803 High Similarity NPC83272
0.8797 High Similarity NPC293453
0.8786 High Similarity NPC220106
0.8777 High Similarity NPC474655
0.8776 High Similarity NPC149618
0.8776 High Similarity NPC89625
0.8768 High Similarity NPC301915
0.8768 High Similarity NPC261292
0.8767 High Similarity NPC217447
0.8759 High Similarity NPC142027
0.8759 High Similarity NPC325983
0.8759 High Similarity NPC27407
0.8759 High Similarity NPC205766
0.875 High Similarity NPC7025
0.875 High Similarity NPC256672
0.875 High Similarity NPC27221
0.8741 High Similarity NPC470357
0.8741 High Similarity NPC107625
0.8741 High Similarity NPC138978
0.8741 High Similarity NPC470570
0.8741 High Similarity NPC237208
0.8741 High Similarity NPC470831
0.8741 High Similarity NPC267509
0.8741 High Similarity NPC214702
0.8732 High Similarity NPC210966
0.8732 High Similarity NPC95123
0.8732 High Similarity NPC210425
0.8732 High Similarity NPC19896
0.8732 High Similarity NPC478203
0.8732 High Similarity NPC277426
0.8732 High Similarity NPC66404
0.8732 High Similarity NPC126882
0.8732 High Similarity NPC86373
0.8732 High Similarity NPC280404
0.8731 High Similarity NPC230818
0.8723 High Similarity NPC314271
0.8723 High Similarity NPC105648
0.8723 High Similarity NPC469579
0.8716 High Similarity NPC146211
0.8714 High Similarity NPC156872
0.8712 High Similarity NPC477454
0.8705 High Similarity NPC472403
0.8705 High Similarity NPC9121
0.8705 High Similarity NPC177307
0.8696 High Similarity NPC191976
0.8696 High Similarity NPC254847
0.869 High Similarity NPC97028
0.869 High Similarity NPC100985
0.869 High Similarity NPC288036
0.869 High Similarity NPC198927
0.869 High Similarity NPC97029
0.869 High Similarity NPC158338
0.869 High Similarity NPC65589
0.869 High Similarity NPC329933
0.8681 High Similarity NPC14098
0.8676 High Similarity NPC476389
0.8676 High Similarity NPC27490
0.8671 High Similarity NPC32470

  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 NPC158481 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
0.9051 High Similarity NPD970 Clinical (unspecified phase)
0.8936 High Similarity NPD2532 Approved
0.8936 High Similarity NPD2534 Approved
0.8936 High Similarity NPD2533 Approved
0.8696 High Similarity NPD1509 Clinical (unspecified phase)
0.8431 Intermediate Similarity NPD6232 Discontinued
0.8417 Intermediate Similarity NPD1607 Approved
0.8333 Intermediate Similarity NPD7819 Suspended
0.8273 Intermediate Similarity NPD1240 Approved
0.8269 Intermediate Similarity NPD7473 Discontinued
0.8219 Intermediate Similarity NPD7390 Discontinued
0.8214 Intermediate Similarity NPD230 Phase 1
0.8169 Intermediate Similarity NPD1510 Phase 2
0.8112 Intermediate Similarity NPD5406 Approved
0.8112 Intermediate Similarity NPD5405 Approved
0.8112 Intermediate Similarity NPD2935 Discontinued
0.8112 Intermediate Similarity NPD5404 Approved
0.8112 Intermediate Similarity NPD5408 Approved
0.8092 Intermediate Similarity NPD9493 Approved
0.8077 Intermediate Similarity NPD5711 Approved
0.8077 Intermediate Similarity NPD5710 Approved
0.8041 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD6959 Discontinued
0.7986 Intermediate Similarity NPD1551 Phase 2
0.797 Intermediate Similarity NPD9545 Approved
0.7931 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7931 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7891 Intermediate Similarity NPD3750 Approved
0.7887 Intermediate Similarity NPD943 Approved
0.7877 Intermediate Similarity NPD1549 Phase 2
0.7868 Intermediate Similarity NPD1201 Approved
0.7857 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7843 Intermediate Similarity NPD7411 Suspended
0.7829 Intermediate Similarity NPD3226 Approved
0.7823 Intermediate Similarity NPD2800 Approved
0.7823 Intermediate Similarity NPD1243 Approved
0.7821 Intermediate Similarity NPD7075 Discontinued
0.7778 Intermediate Similarity NPD6651 Approved
0.7778 Intermediate Similarity NPD6599 Discontinued
0.777 Intermediate Similarity NPD1164 Approved
0.777 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD1470 Approved
0.777 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD7768 Phase 2
0.7742 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD1511 Approved
0.7721 Intermediate Similarity NPD4626 Approved
0.7716 Intermediate Similarity NPD5844 Phase 1
0.7707 Intermediate Similarity NPD3749 Approved
0.7698 Intermediate Similarity NPD1283 Approved
0.7692 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7687 Intermediate Similarity NPD2346 Discontinued
0.7682 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7681 Intermediate Similarity NPD9269 Phase 2
0.7677 Intermediate Similarity NPD1934 Approved
0.7662 Intermediate Similarity NPD4380 Phase 2
0.7647 Intermediate Similarity NPD9268 Approved
0.764 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD1512 Approved
0.7622 Intermediate Similarity NPD3764 Approved
0.7622 Intermediate Similarity NPD411 Approved
0.7616 Intermediate Similarity NPD6799 Approved
0.7582 Intermediate Similarity NPD920 Approved
0.7564 Intermediate Similarity NPD6801 Discontinued
0.7554 Intermediate Similarity NPD9717 Approved
0.7551 Intermediate Similarity NPD3748 Approved
0.755 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD2801 Approved
0.7516 Intermediate Similarity NPD1465 Phase 2
0.75 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2796 Approved
0.75 Intermediate Similarity NPD6100 Approved
0.75 Intermediate Similarity NPD6099 Approved
0.7482 Intermediate Similarity NPD1281 Approved
0.7481 Intermediate Similarity NPD74 Approved
0.7481 Intermediate Similarity NPD9266 Approved
0.7468 Intermediate Similarity NPD3817 Phase 2
0.7467 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD919 Approved
0.7432 Intermediate Similarity NPD2799 Discontinued
0.7426 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD3882 Suspended
0.7417 Intermediate Similarity NPD4628 Phase 3
0.7417 Intermediate Similarity NPD7003 Approved
0.7405 Intermediate Similarity NPD9264 Approved
0.7405 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD9267 Approved
0.7405 Intermediate Similarity NPD9263 Approved
0.7394 Intermediate Similarity NPD1203 Approved
0.7391 Intermediate Similarity NPD5691 Approved
0.7379 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD6559 Discontinued
0.7357 Intermediate Similarity NPD422 Phase 1
0.7347 Intermediate Similarity NPD447 Suspended
0.7338 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD5953 Discontinued
0.7305 Intermediate Similarity NPD1608 Approved
0.7283 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD8150 Discontinued
0.7237 Intermediate Similarity NPD2654 Approved
0.7233 Intermediate Similarity NPD37 Approved
0.7212 Intermediate Similarity NPD6166 Phase 2
0.7212 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD4625 Phase 3
0.7186 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD7286 Phase 2
0.7178 Intermediate Similarity NPD5494 Approved
0.7164 Intermediate Similarity NPD4750 Phase 3
0.7153 Intermediate Similarity NPD9281 Approved
0.7152 Intermediate Similarity NPD7458 Discontinued
0.7143 Intermediate Similarity NPD7074 Phase 3
0.7143 Intermediate Similarity NPD1651 Approved
0.7143 Intermediate Similarity NPD2313 Discontinued
0.7134 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD3818 Discontinued
0.7117 Intermediate Similarity NPD6234 Discontinued
0.7115 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD2344 Approved
0.7103 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD4965 Approved
0.7099 Intermediate Similarity NPD4966 Approved
0.7099 Intermediate Similarity NPD4967 Phase 2
0.7099 Intermediate Similarity NPD9261 Approved
0.7092 Intermediate Similarity NPD17 Approved
0.7092 Intermediate Similarity NPD1778 Approved
0.7091 Intermediate Similarity NPD7229 Phase 3
0.7086 Intermediate Similarity NPD4308 Phase 3
0.7083 Intermediate Similarity NPD7054 Approved
0.7069 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD2979 Phase 3
0.7041 Intermediate Similarity NPD7472 Approved
0.7037 Intermediate Similarity NPD4288 Approved
0.7037 Intermediate Similarity NPD5402 Approved
0.703 Intermediate Similarity NPD1247 Approved
0.7027 Intermediate Similarity NPD1296 Phase 2
0.7025 Intermediate Similarity NPD5403 Approved
0.7024 Intermediate Similarity NPD7177 Discontinued
0.7023 Intermediate Similarity NPD940 Approved
0.7023 Intermediate Similarity NPD846 Approved
0.7018 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD4749 Approved
0.7007 Intermediate Similarity NPD6832 Phase 2
0.7006 Intermediate Similarity NPD5401 Approved
0.7 Intermediate Similarity NPD6797 Phase 2
0.7 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.6986 Remote Similarity NPD1019 Discontinued
0.6986 Remote Similarity NPD2798 Approved
0.6977 Remote Similarity NPD8313 Approved
0.6977 Remote Similarity NPD8312 Approved
0.6973 Remote Similarity NPD8151 Discontinued
0.6959 Remote Similarity NPD7251 Discontinued
0.6944 Remote Similarity NPD3972 Approved
0.6943 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6939 Remote Similarity NPD9494 Approved
0.6933 Remote Similarity NPD4060 Phase 1
0.6928 Remote Similarity NPD7199 Phase 2
0.6928 Remote Similarity NPD2438 Suspended
0.6923 Remote Similarity NPD2309 Approved
0.6919 Remote Similarity NPD7808 Phase 3
0.6918 Remote Similarity NPD2797 Approved
0.6913 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6913 Remote Similarity NPD3268 Approved
0.6913 Remote Similarity NPD4907 Clinical (unspecified phase)
0.691 Remote Similarity NPD6534 Approved
0.691 Remote Similarity NPD6535 Approved
0.6901 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6887 Remote Similarity NPD5124 Phase 1
0.6887 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6885 Remote Similarity NPD7435 Discontinued
0.6883 Remote Similarity NPD1471 Phase 3
0.6882 Remote Similarity NPD6020 Phase 2
0.6879 Remote Similarity NPD3300 Phase 2
0.6875 Remote Similarity NPD1610 Phase 2
0.6867 Remote Similarity NPD520 Approved
0.6867 Remote Similarity NPD6663 Approved
0.6863 Remote Similarity NPD7033 Discontinued
0.6859 Remote Similarity NPD8166 Discontinued
0.6855 Remote Similarity NPD6273 Approved
0.6853 Remote Similarity NPD2932 Approved
0.6853 Remote Similarity NPD3019 Approved
0.6848 Remote Similarity NPD8319 Approved
0.6848 Remote Similarity NPD8320 Phase 1
0.6846 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6845 Remote Similarity NPD3926 Phase 2
0.6845 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6824 Remote Similarity NPD5736 Approved
0.6824 Remote Similarity NPD7228 Approved
0.6821 Remote Similarity NPD4307 Phase 2
0.6818 Remote Similarity NPD4477 Approved
0.6818 Remote Similarity NPD4476 Approved
0.6818 Remote Similarity NPD2531 Phase 2
0.6815 Remote Similarity NPD6190 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