Structure

Physi-Chem Properties

Molecular Weight:  150.03
Volume:  145.636
LogP:  1.329
LogD:  1.379
LogS:  -2.277
# Rotatable Bonds:  1
TPSA:  35.53
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.565
Synthetic Accessibility Score:  1.984
Fsp3:  0.125
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.53
MDCK Permeability:  2.3154960217652842e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.057

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.914
Plasma Protein Binding (PPB):  85.814453125%
Volume Distribution (VD):  1.597
Pgp-substrate:  11.46889877319336%

ADMET: Metabolism

CYP1A2-inhibitor:  0.993
CYP1A2-substrate:  0.237
CYP2C19-inhibitor:  0.588
CYP2C19-substrate:  0.342
CYP2C9-inhibitor:  0.096
CYP2C9-substrate:  0.758
CYP2D6-inhibitor:  0.779
CYP2D6-substrate:  0.562
CYP3A4-inhibitor:  0.498
CYP3A4-substrate:  0.188

ADMET: Excretion

Clearance (CL):  11.23
Half-life (T1/2):  0.666

ADMET: Toxicity

hERG Blockers:  0.055
Human Hepatotoxicity (H-HT):  0.029
Drug-inuced Liver Injury (DILI):  0.043
AMES Toxicity:  0.049
Rat Oral Acute Toxicity:  0.01
Maximum Recommended Daily Dose:  0.034
Skin Sensitization:  0.415
Carcinogencity:  0.927
Eye Corrosion:  0.95
Eye Irritation:  0.987
Respiratory Toxicity:  0.971

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Similar NPs/Drugs  

  Natural Product: NPC120066

Natural Product ID:  NPC120066
Common Name*:   Piperonal
IUPAC Name:   1,3-benzodioxole-5-carbaldehyde
Synonyms:   Benzo[D][1,3]Dioxole-5-Carbaldehyde; Piperonal
Standard InCHIKey:  SATCULPHIDQDRE-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H2
SMILES:  c1cc2c(cc1C=O)OCO2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL271663
PubChem CID:   8438
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000296] Benzodioxoles

*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
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. fruit n.a. DOI[10.1016/S0040-4039(01)00209-X]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[10575373]
NPO10274 Pothomorphe peltata n.a. n.a. n.a. n.a. Dominican Republic n.a. PMID[11430019]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[11551759]
NPO6544 Carpesium longifolium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[14695795]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. leaf n.a. PMID[15467205]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. whole plant n.a. PMID[16808005]
NPO3968 Dracontium loretense Species Araceae Eukaryota n.a. n.a. n.a. PMID[19341262]
NPO3968 Dracontium loretense Species Araceae Eukaryota corms Iquitos, Peru 2005-MAY PMID[19341262]
NPO10666 Verbesina virginica Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[19485332]
NPO10742 Galium verum Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[20209910]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. whole plant n.a. PMID[21214467]
NPO4251 Photorhabdus luminescens Species Morganellaceae Bacteria n.a. n.a. n.a. PMID[22909174]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[23102654]
NPO12125 Pseudomonas stutzeri Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[23149469]
NPO6648 Piper retrofractum Species Piperaceae Eukaryota Fruits n.a. n.a. PMID[23506561]
NPO6648 Piper retrofractum Species Piperaceae Eukaryota leaves n.a. n.a. PMID[25127165]
NPO4251 Photorhabdus luminescens Species Morganellaceae Bacteria n.a. n.a. n.a. PMID[25988621]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[31103896]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. Database[FooDB]
NPO28928 Piper nigrum Species Piperaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. Database[FooDB]
NPO6544 Carpesium longifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7158 Schefflera venulosa Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10742 Galium verum Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28036 Distemonanthus benthamianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7158 Schefflera venulosa Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10742 Galium verum Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6648 Piper retrofractum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6544 Carpesium longifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28036 Distemonanthus benthamianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12383 Frullania brasiliensis Species Frullaniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27487 Silene banksia Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28036 Distemonanthus benthamianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10742 Galium verum Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO43 Leifsonia aquatica Species Microbacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12488 Bupleurum rigidum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23642 Penicillium tardum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28036 Distemonanthus benthamianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6544 Carpesium longifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6880 Crocus corsicus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2393 Matsumurella chinensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12125 Pseudomonas stutzeri Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12383 Frullania brasiliensis Species Frullaniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10742 Galium verum Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7536 Mycoplasma mycoides Species Mycoplasmataceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO4251 Photorhabdus luminescens Species Morganellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6648 Piper retrofractum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6428 Euphorbia wangii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10459 Brickellia longifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8639 Agaricus xanthodermus Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3968 Dracontium loretense Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13059 Abies webbiana Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2840 Podocarpus minor Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10666 Verbesina virginica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10274 Pothomorphe peltata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO27487 Silene banksia Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO964 Homalium laurifolium Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9166 Monascus rubropunctatus Species Fellodistomidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28392 Macrosiphum liriodendri Species Aphididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9950 Coelogyne nitida Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28218 Asplenium adiantum-nigrum Species Aspleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO876 Didymosphaeria enalia Species Didymosphaeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11137 Dichotomanthes tristaniicarpa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO230 Palisota barteri Species Commelinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11511 Cochlearia officinalis Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7158 Schefflera venulosa Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28510 Aspergillus pseudodeflectus Species Aspergillaceae 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
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 4835 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 2694.5 nM PubChem BioAssay data set
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 20.0 % PMID[520172]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 23.0 % PMID[520172]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 39.0 % PMID[520172]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 11.0 % PMID[520173]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 20.0 % PMID[520173]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = -3.0 % PMID[520173]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 39.0 % PMID[520173]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 4.0 % PMID[520173]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 23.0 % PMID[520173]
NPT1460 Cell Line L929 Mus musculus Inhibition = -4.0 % PMID[520173]
NPT1460 Cell Line L929 Mus musculus Inhibition = 10.0 % PMID[520173]
NPT1460 Cell Line L929 Mus musculus Inhibition = 0.0 % PMID[520173]
NPT1460 Cell Line L929 Mus musculus Inhibition = 1.0 % PMID[520173]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 0.0 % PMID[520173]
NPT149 Individual Protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 39810.7 nM PMID[520174]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency = 2818.4 nM PMID[520174]
NPT3175 Individual Protein Collagen Meloidogyne javanica Activity = 30.0 % PMID[520176]
NPT3175 Individual Protein Collagen Meloidogyne javanica Activity = 5.0 % PMID[520176]
NPT65 Cell Line HepG2 Homo sapiens CC50 = 1289310.0 nM PMID[520179]
NPT2 Others Unspecified Potency n.a. 1.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Inhibition = 1.0 % PMID[520173]
NPT2 Others Unspecified Inhibition = 2.0 % PMID[520173]
NPT2 Others Unspecified Inhibition = 7.0 % PMID[520173]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 14125.4 nM PMID[520174]
NPT734 Organism Musca domestica Musca domestica LD50 = 36.1 ug PMID[520175]
NPT735 Individual Protein GABA receptor subunit Musca domestica Activity = 93.0 % PMID[520175]
NPT450 Organism Meloidogyne incognita Meloidogyne incognita EC100 > 100.0 mg/L PMID[520176]
NPT450 Organism Meloidogyne incognita Meloidogyne incognita EC50 = 44.0 ug.mL-1 PMID[520176]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 3330000.0 nM PMID[520177]
NPT19 Organism Escherichia coli Escherichia coli MIC = 3330000.0 nM PMID[520177]
NPT20 Organism Candida albicans Candida albicans MIC = 830000.0 nM PMID[520177]
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 3330000.0 nM PMID[520177]
NPT187 Organism Issatchenkia orientalis Pichia kudriavzevii MIC = 830000.0 nM PMID[520177]
NPT21 Organism Aspergillus niger Aspergillus niger MIC = 3330000.0 nM PMID[520177]
NPT1262 Organism Aspergillus parasiticus Aspergillus parasiticus MIC = 3330000.0 nM PMID[520177]
NPT1263 Organism Aspergillus sydowii Aspergillus sydowii MIC = 3330000.0 nM PMID[520177]
NPT329 Organism Trichophyton rubrum Trichophyton rubrum MIC = 830000.0 nM PMID[520177]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 830000.0 nM PMID[520177]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 6660000.0 nM PMID[520177]
NPT1033 Organism Enterobacter cloacae Enterobacter cloacae MIC = 3330000.0 nM PMID[520177]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae MIC = 3330000.0 nM PMID[520177]
NPT35 Others n.a. IC50 = 906943000.0 nM PMID[520178]
NPT813 Individual Protein GABA transporter 1 Mus musculus Activity = 81.0 % PMID[520180]

☑ 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 NPC120066 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
0.935 High Similarity NPC286683
0.925 High Similarity NPC295317
0.907 High Similarity NPC38101
0.8992 High Similarity NPC111225
0.888 High Similarity NPC473626
0.8846 High Similarity NPC45404
0.878 High Similarity NPC225245
0.874 High Similarity NPC117237
0.874 High Similarity NPC203719
0.8571 High Similarity NPC474691
0.8538 High Similarity NPC298268
0.8527 High Similarity NPC304747
0.8516 High Similarity NPC154275
0.8455 Intermediate Similarity NPC212643
0.8455 Intermediate Similarity NPC199209
0.8417 Intermediate Similarity NPC57879
0.8417 Intermediate Similarity NPC54626
0.8359 Intermediate Similarity NPC30216
0.8346 Intermediate Similarity NPC256167
0.8345 Intermediate Similarity NPC327052
0.8333 Intermediate Similarity NPC179309
0.8333 Intermediate Similarity NPC137920
0.8333 Intermediate Similarity NPC125134
0.8333 Intermediate Similarity NPC86455
0.8321 Intermediate Similarity NPC28398
0.832 Intermediate Similarity NPC57501
0.832 Intermediate Similarity NPC69670
0.831 Intermediate Similarity NPC227980
0.8308 Intermediate Similarity NPC16651
0.8308 Intermediate Similarity NPC32163
0.8284 Intermediate Similarity NPC144662
0.8273 Intermediate Similarity NPC469978
0.8273 Intermediate Similarity NPC46880
0.8268 Intermediate Similarity NPC114845
0.8258 Intermediate Similarity NPC477694
0.8258 Intermediate Similarity NPC285776
0.8258 Intermediate Similarity NPC477705
0.825 Intermediate Similarity NPC127326
0.8227 Intermediate Similarity NPC153620
0.8227 Intermediate Similarity NPC24257
0.8214 Intermediate Similarity NPC229787
0.8211 Intermediate Similarity NPC252004
0.8195 Intermediate Similarity NPC477706
0.8194 Intermediate Similarity NPC289438
0.8182 Intermediate Similarity NPC31279
0.8162 Intermediate Similarity NPC102260
0.8162 Intermediate Similarity NPC230968
0.8156 Intermediate Similarity NPC224687
0.8148 Intermediate Similarity NPC237330
0.8134 Intermediate Similarity NPC50763
0.8134 Intermediate Similarity NPC111888
0.8125 Intermediate Similarity NPC193484
0.812 Intermediate Similarity NPC299010
0.8088 Intermediate Similarity NPC274613
0.808 Intermediate Similarity NPC316062
0.8074 Intermediate Similarity NPC283823
0.8074 Intermediate Similarity NPC159418
0.8074 Intermediate Similarity NPC288743
0.8045 Intermediate Similarity NPC261759
0.8042 Intermediate Similarity NPC470088
0.8033 Intermediate Similarity NPC183648
0.803 Intermediate Similarity NPC64948
0.8028 Intermediate Similarity NPC296575
0.8 Intermediate Similarity NPC278102
0.8 Intermediate Similarity NPC153453
0.7986 Intermediate Similarity NPC470855
0.7985 Intermediate Similarity NPC66905
0.7971 Intermediate Similarity NPC474274
0.7971 Intermediate Similarity NPC157944
0.7967 Intermediate Similarity NPC23332
0.7956 Intermediate Similarity NPC139519
0.7943 Intermediate Similarity NPC27220
0.7941 Intermediate Similarity NPC205915
0.7931 Intermediate Similarity NPC37220
0.7891 Intermediate Similarity NPC148497
0.7891 Intermediate Similarity NPC153008
0.7891 Intermediate Similarity NPC308555
0.7883 Intermediate Similarity NPC155098
0.7883 Intermediate Similarity NPC19890
0.7883 Intermediate Similarity NPC110958
0.7879 Intermediate Similarity NPC85830
0.7874 Intermediate Similarity NPC39793
0.7872 Intermediate Similarity NPC104956
0.7862 Intermediate Similarity NPC127827
0.7862 Intermediate Similarity NPC24193
0.7857 Intermediate Similarity NPC220540
0.7838 Intermediate Similarity NPC478213
0.7826 Intermediate Similarity NPC89504
0.7826 Intermediate Similarity NPC212729
0.7826 Intermediate Similarity NPC95485
0.7826 Intermediate Similarity NPC88065
0.7823 Intermediate Similarity NPC118332
0.7823 Intermediate Similarity NPC288316
0.7823 Intermediate Similarity NPC470708
0.7817 Intermediate Similarity NPC299154
0.7817 Intermediate Similarity NPC472564
0.7812 Intermediate Similarity NPC205502
0.7808 Intermediate Similarity NPC205054
0.7801 Intermediate Similarity NPC51681
0.7801 Intermediate Similarity NPC250597
0.7795 Intermediate Similarity NPC268317
0.7793 Intermediate Similarity NPC181464
0.7786 Intermediate Similarity NPC114298
0.7786 Intermediate Similarity NPC325625
0.7786 Intermediate Similarity NPC233780
0.7785 Intermediate Similarity NPC254163
0.7778 Intermediate Similarity NPC294941
0.777 Intermediate Similarity NPC104728
0.777 Intermediate Similarity NPC68882
0.777 Intermediate Similarity NPC35544
0.7769 Intermediate Similarity NPC471877
0.7763 Intermediate Similarity NPC109238
0.7762 Intermediate Similarity NPC15743
0.7761 Intermediate Similarity NPC223807
0.7734 Intermediate Similarity NPC240664
0.7734 Intermediate Similarity NPC185738
0.7734 Intermediate Similarity NPC33271
0.7733 Intermediate Similarity NPC261484
0.7733 Intermediate Similarity NPC261090
0.7727 Intermediate Similarity NPC242372
0.7727 Intermediate Similarity NPC141252
0.7727 Intermediate Similarity NPC4181
0.7727 Intermediate Similarity NPC11799
0.7727 Intermediate Similarity NPC257976
0.7727 Intermediate Similarity NPC164778
0.7718 Intermediate Similarity NPC244371
0.7718 Intermediate Similarity NPC57211
0.7714 Intermediate Similarity NPC110899
0.7714 Intermediate Similarity NPC125417
0.7714 Intermediate Similarity NPC14022
0.7714 Intermediate Similarity NPC25305
0.7714 Intermediate Similarity NPC95679
0.7714 Intermediate Similarity NPC112068
0.7708 Intermediate Similarity NPC213900
0.7704 Intermediate Similarity NPC50583
0.7703 Intermediate Similarity NPC220577
0.7703 Intermediate Similarity NPC36130
0.7703 Intermediate Similarity NPC134905
0.7703 Intermediate Similarity NPC279061
0.7698 Intermediate Similarity NPC208760
0.7698 Intermediate Similarity NPC53953
0.7698 Intermediate Similarity NPC204592
0.7687 Intermediate Similarity NPC475722
0.7682 Intermediate Similarity NPC226759
0.7682 Intermediate Similarity NPC82733
0.7682 Intermediate Similarity NPC76458
0.7676 Intermediate Similarity NPC326065
0.7674 Intermediate Similarity NPC277460
0.7669 Intermediate Similarity NPC312404
0.7669 Intermediate Similarity NPC273686
0.7667 Intermediate Similarity NPC310905
0.7667 Intermediate Similarity NPC478238
0.7667 Intermediate Similarity NPC12714
0.7667 Intermediate Similarity NPC3273
0.766 Intermediate Similarity NPC470962
0.7656 Intermediate Similarity NPC470860
0.7655 Intermediate Similarity NPC9370
0.7655 Intermediate Similarity NPC473867
0.7655 Intermediate Similarity NPC287495
0.7655 Intermediate Similarity NPC30890
0.7651 Intermediate Similarity NPC292460
0.7651 Intermediate Similarity NPC52623
0.7651 Intermediate Similarity NPC137813
0.7647 Intermediate Similarity NPC226855
0.7643 Intermediate Similarity NPC160425
0.7643 Intermediate Similarity NPC90431
0.7639 Intermediate Similarity NPC469615
0.7639 Intermediate Similarity NPC473090
0.7635 Intermediate Similarity NPC234152
0.7634 Intermediate Similarity NPC158949
0.7632 Intermediate Similarity NPC215375
0.7632 Intermediate Similarity NPC62518
0.7632 Intermediate Similarity NPC15764
0.7632 Intermediate Similarity NPC68619
0.763 Intermediate Similarity NPC158654
0.763 Intermediate Similarity NPC281020
0.7626 Intermediate Similarity NPC311339
0.7616 Intermediate Similarity NPC301897
0.7616 Intermediate Similarity NPC109765
0.7615 Intermediate Similarity NPC37858
0.7615 Intermediate Similarity NPC61779
0.7615 Intermediate Similarity NPC299406
0.7615 Intermediate Similarity NPC119949
0.7612 Intermediate Similarity NPC470858
0.7606 Intermediate Similarity NPC223336
0.7606 Intermediate Similarity NPC4796
0.7603 Intermediate Similarity NPC88345
0.76 Intermediate Similarity NPC194095
0.76 Intermediate Similarity NPC327032
0.76 Intermediate Similarity NPC191046
0.76 Intermediate Similarity NPC54179
0.76 Intermediate Similarity NPC279930
0.7597 Intermediate Similarity NPC469954
0.7589 Intermediate Similarity NPC166184
0.7586 Intermediate Similarity NPC474158
0.7586 Intermediate Similarity NPC27106
0.7586 Intermediate Similarity NPC275278
0.7586 Intermediate Similarity NPC469683
0.7584 Intermediate Similarity NPC104353
0.7583 Intermediate Similarity NPC13755

  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 NPC120066 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
0.874 High Similarity NPD9494 Approved
0.7917 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7752 Intermediate Similarity NPD1357 Approved
0.7734 Intermediate Similarity NPD5536 Phase 2
0.7708 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD3705 Approved
0.7429 Intermediate Similarity NPD1933 Approved
0.7429 Intermediate Similarity NPD447 Suspended
0.7422 Intermediate Similarity NPD1241 Discontinued
0.7376 Intermediate Similarity NPD2492 Phase 1
0.736 Intermediate Similarity NPD1358 Approved
0.7333 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD230 Phase 1
0.7296 Intermediate Similarity NPD3818 Discontinued
0.729 Intermediate Similarity NPD919 Approved
0.7273 Intermediate Similarity NPD9545 Approved
0.7259 Intermediate Similarity NPD3972 Approved
0.7237 Intermediate Similarity NPD6386 Approved
0.7237 Intermediate Similarity NPD6385 Approved
0.7197 Intermediate Similarity NPD1247 Approved
0.7171 Intermediate Similarity NPD1337 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD3882 Suspended
0.7153 Intermediate Similarity NPD1876 Approved
0.7143 Intermediate Similarity NPD3134 Approved
0.7132 Intermediate Similarity NPD228 Approved
0.7105 Intermediate Similarity NPD824 Approved
0.7101 Intermediate Similarity NPD1049 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD9268 Approved
0.7067 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7028 Phase 2
0.7047 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD5494 Approved
0.7023 Intermediate Similarity NPD5283 Phase 1
0.7012 Intermediate Similarity NPD7685 Pre-registration
0.7007 Intermediate Similarity NPD9269 Phase 2
0.6993 Remote Similarity NPD7458 Discontinued
0.6987 Remote Similarity NPD5977 Approved
0.6987 Remote Similarity NPD5978 Approved
0.6987 Remote Similarity NPD5353 Approved
0.6953 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6934 Remote Similarity NPD1281 Approved
0.6934 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6929 Remote Similarity NPD2798 Approved
0.6923 Remote Similarity NPD1006 Clinical (unspecified phase)
0.6923 Remote Similarity NPD554 Clinical (unspecified phase)
0.6913 Remote Similarity NPD4628 Phase 3
0.6912 Remote Similarity NPD17 Approved
0.6879 Remote Similarity NPD3817 Phase 2
0.6875 Remote Similarity NPD3142 Approved
0.6875 Remote Similarity NPD3140 Approved
0.6863 Remote Similarity NPD920 Approved
0.6859 Remote Similarity NPD37 Approved
0.6859 Remote Similarity NPD1934 Approved
0.6849 Remote Similarity NPD743 Approved
0.6842 Remote Similarity NPD3688 Clinical (unspecified phase)
0.6842 Remote Similarity NPD3146 Approved
0.6838 Remote Similarity NPD1651 Approved
0.6835 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6829 Remote Similarity NPD7054 Approved
0.6828 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6824 Remote Similarity NPD2344 Approved
0.6824 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6815 Remote Similarity NPD2801 Approved
0.6809 Remote Similarity NPD1019 Discontinued
0.6803 Remote Similarity NPD1510 Phase 2
0.68 Remote Similarity NPD4109 Clinical (unspecified phase)
0.68 Remote Similarity NPD4110 Phase 3
0.6795 Remote Similarity NPD6873 Phase 2
0.679 Remote Similarity NPD5242 Approved
0.679 Remote Similarity NPD3926 Phase 2
0.6788 Remote Similarity NPD7472 Approved
0.6788 Remote Similarity NPD7074 Phase 3
0.6786 Remote Similarity NPD1283 Approved
0.6776 Remote Similarity NPD1511 Approved
0.677 Remote Similarity NPD7199 Phase 2
0.6766 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6763 Remote Similarity NPD1608 Approved
0.6763 Remote Similarity NPD9717 Approved
0.6759 Remote Similarity NPD1240 Approved
0.6757 Remote Similarity NPD2935 Discontinued
0.6757 Remote Similarity NPD2796 Approved
0.6755 Remote Similarity NPD3887 Approved
0.6741 Remote Similarity NPD9493 Approved
0.6736 Remote Similarity NPD411 Approved
0.673 Remote Similarity NPD4967 Phase 2
0.673 Remote Similarity NPD4966 Approved
0.673 Remote Similarity NPD4965 Approved
0.6715 Remote Similarity NPD5691 Approved
0.6713 Remote Similarity NPD6832 Phase 2
0.6711 Remote Similarity NPD1471 Phase 3
0.6711 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6711 Remote Similarity NPD2353 Approved
0.6709 Remote Similarity NPD1465 Phase 2
0.6689 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6688 Remote Similarity NPD1512 Approved
0.6687 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6687 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1238 Approved
0.6667 Remote Similarity NPD1607 Approved
0.6667 Remote Similarity NPD1778 Approved
0.6667 Remote Similarity NPD9697 Approved
0.6667 Remote Similarity NPD2822 Clinical (unspecified phase)
0.6667 Remote Similarity NPD970 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6799 Approved
0.6667 Remote Similarity NPD7808 Phase 3
0.6667 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6647 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6647 Remote Similarity NPD6797 Phase 2
0.6646 Remote Similarity NPD6234 Discontinued
0.6645 Remote Similarity NPD2309 Approved
0.6645 Remote Similarity NPD6190 Approved
0.6644 Remote Similarity NPD1551 Phase 2
0.6644 Remote Similarity NPD943 Approved
0.6642 Remote Similarity NPD1894 Discontinued
0.6641 Remote Similarity NPD9261 Approved
0.6626 Remote Similarity NPD6232 Discontinued
0.6623 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6623 Remote Similarity NPD1243 Approved
0.6621 Remote Similarity NPD3764 Approved
0.662 Remote Similarity NPD1203 Approved
0.6607 Remote Similarity NPD7251 Discontinued
0.6607 Remote Similarity NPD6559 Discontinued
0.6604 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6603 Remote Similarity NPD1653 Approved
0.6594 Remote Similarity NPD5585 Approved
0.6581 Remote Similarity NPD6273 Approved
0.6577 Remote Similarity NPD2799 Discontinued
0.6569 Remote Similarity NPD9092 Discovery
0.6558 Remote Similarity NPD4357 Discontinued
0.6556 Remote Similarity NPD1549 Phase 2
0.6547 Remote Similarity NPD4626 Approved
0.6538 Remote Similarity NPD6662 Clinical (unspecified phase)
0.6536 Remote Similarity NPD2354 Approved
0.6533 Remote Similarity NPD2438 Suspended
0.6531 Remote Similarity NPD2979 Phase 3
0.6527 Remote Similarity NPD5844 Phase 1
0.6525 Remote Similarity NPD2981 Phase 2
0.6516 Remote Similarity NPD2533 Approved
0.6516 Remote Similarity NPD2534 Approved
0.6516 Remote Similarity NPD2532 Approved
0.6515 Remote Similarity NPD2684 Approved
0.6507 Remote Similarity NPD2313 Discontinued
0.6506 Remote Similarity NPD7473 Discontinued
0.6497 Remote Similarity NPD957 Approved
0.6496 Remote Similarity NPD405 Clinical (unspecified phase)
0.6494 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6493 Remote Similarity NPD1609 Clinical (unspecified phase)
0.649 Remote Similarity NPD1552 Clinical (unspecified phase)
0.649 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6488 Remote Similarity NPD2325 Approved
0.6486 Remote Similarity NPD6355 Discontinued
0.6479 Remote Similarity NPD2982 Phase 2
0.6479 Remote Similarity NPD2983 Phase 2
0.6467 Remote Similarity NPD3748 Approved
0.6467 Remote Similarity NPD2163 Approved
0.6467 Remote Similarity NPD651 Clinical (unspecified phase)
0.6463 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6463 Remote Similarity NPD2821 Approved
0.6462 Remote Similarity NPD164 Approved
0.6456 Remote Similarity NPD3455 Phase 2
0.6446 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6446 Remote Similarity NPD6166 Phase 2
0.6446 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6439 Remote Similarity NPD9267 Approved
0.6439 Remote Similarity NPD9263 Approved
0.6439 Remote Similarity NPD9264 Approved
0.6438 Remote Similarity NPD6280 Approved
0.6438 Remote Similarity NPD6279 Approved
0.6437 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6433 Remote Similarity NPD1670 Discontinued
0.6429 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6419 Remote Similarity NPD4307 Phase 2
0.6415 Remote Similarity NPD4380 Phase 2
0.6415 Remote Similarity NPD6599 Discontinued
0.6414 Remote Similarity NPD454 Approved
0.6408 Remote Similarity NPD1481 Phase 2
0.6405 Remote Similarity NPD2654 Approved
0.6403 Remote Similarity NPD1182 Approved
0.6398 Remote Similarity NPD7819 Suspended
0.6398 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6398 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6395 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6395 Remote Similarity NPD6798 Discontinued
0.6391 Remote Similarity NPD74 Approved
0.6391 Remote Similarity NPD9266 Approved
0.6391 Remote Similarity NPD2182 Approved
0.6384 Remote Similarity NPD2745 Approved
0.6384 Remote Similarity NPD2746 Clinical (unspecified phase)
0.6383 Remote Similarity NPD3496 Discontinued
0.6382 Remote Similarity NPD1375 Discontinued
0.6382 Remote Similarity NPD2346 Discontinued
0.6382 Remote Similarity NPD7266 Discontinued
0.6375 Remote Similarity NPD958 Approved
0.6375 Remote Similarity NPD7109 Clinical (unspecified phase)
0.6375 Remote Similarity NPD7110 Phase 1
0.637 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6369 Remote Similarity NPD2186 Approved
0.6369 Remote Similarity NPD7228 Approved
0.6364 Remote Similarity NPD4359 Approved
0.6364 Remote Similarity NPD7003 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