Structure

Physi-Chem Properties

Molecular Weight:  273.14
Volume:  289.728
LogP:  2.962
LogD:  3.559
LogS:  -4.339
# Rotatable Bonds:  6
TPSA:  47.56
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.663
Synthetic Accessibility Score:  2.399
Fsp3:  0.312
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.776
MDCK Permeability:  1.734812576614786e-05
Pgp-inhibitor:  0.995
Pgp-substrate:  0.042
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.641
Plasma Protein Binding (PPB):  94.95687103271484%
Volume Distribution (VD):  0.68
Pgp-substrate:  5.430474281311035%

ADMET: Metabolism

CYP1A2-inhibitor:  0.968
CYP1A2-substrate:  0.142
CYP2C19-inhibitor:  0.915
CYP2C19-substrate:  0.442
CYP2C9-inhibitor:  0.655
CYP2C9-substrate:  0.978
CYP2D6-inhibitor:  0.888
CYP2D6-substrate:  0.902
CYP3A4-inhibitor:  0.917
CYP3A4-substrate:  0.19

ADMET: Excretion

Clearance (CL):  13.046
Half-life (T1/2):  0.315

ADMET: Toxicity

hERG Blockers:  0.39
Human Hepatotoxicity (H-HT):  0.276
Drug-inuced Liver Injury (DILI):  0.533
AMES Toxicity:  0.028
Rat Oral Acute Toxicity:  0.006
Maximum Recommended Daily Dose:  0.022
Skin Sensitization:  0.538
Carcinogencity:  0.89
Eye Corrosion:  0.026
Eye Irritation:  0.632
Respiratory Toxicity:  0.368

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Similar NPs/Drugs  

  Natural Product: NPC207541

Natural Product ID:  NPC207541
Common Name*:   Piperlonguminine
IUPAC Name:   (2E,4E)-5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienamide
Synonyms:   Piperlonguminine
Standard InCHIKey:  WHAAPCGHVWVUEX-GGWOSOGESA-N
Standard InCHI:  InChI=1S/C16H19NO3/c1-12(2)10-17-16(18)6-4-3-5-13-7-8-14-15(9-13)20-11-19-14/h3-9,12H,10-11H2,1-2H3,(H,17,18)/b5-3+,6-4+
SMILES:  CC(C)CN=C(/C=C/C=C/c1ccc2c(c1)OCO2)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL253973
PubChem CID:   5320621
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]
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]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[1659613]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. whole plant n.a. PMID[16808005]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[16872768]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota stem bark n.a. n.a. PMID[17918910]
NPO33260 piper hoffmanseggianum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[18031016]
NPO7781 Piper scutifolium Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[18031016]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota Stems; Barks n.a. n.a. PMID[19086868]
NPO3968 Dracontium loretense Species Araceae Eukaryota corms Iquitos, Peru 2005-MAY PMID[19341262]
NPO3968 Dracontium loretense Species Araceae Eukaryota n.a. n.a. n.a. PMID[19341262]
NPO10666 Verbesina virginica Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[19485332]
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]
NPO26237 Piper longum Species Piperaceae Eukaryota fruits n.a. n.a. PMID[20839888]
NPO16665 Tephrosia semiglabra Species Geometridae Eukaryota n.a. n.a. n.a. PMID[2089123]
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]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[23434420]
NPO6648 Piper retrofractum Species Piperaceae Eukaryota Fruits n.a. n.a. PMID[23506561]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. bark n.a. PMID[23823874]
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]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[28485933]
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]
NPO31534 Piper chaba Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7158 Schefflera venulosa Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6544 Carpesium longifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22661 Pinus aristata Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27487 Silene banksia Species Caryophyllaceae 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]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7158 Schefflera venulosa Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26195 Tephrosia crassifolia Species Geometridae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12383 Frullania brasiliensis Species Frullaniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22661 Pinus aristata Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7536 Mycoplasma mycoides Species Mycoplasmataceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26195 Tephrosia crassifolia Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17401 Kopsia lapidilecta Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28938 Artemisia coerulescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26094 Stolonica socialis Species Styelidae 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]
NPO4251 Photorhabdus luminescens Species Morganellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12125 Pseudomonas stutzeri Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO10459 Brickellia longifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16665 Tephrosia semiglabra Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12383 Frullania brasiliensis Species Frullaniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3968 Dracontium loretense Species Araceae Eukaryota 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]
NPO7781 Piper scutifolium Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13059 Abies webbiana Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8639 Agaricus xanthodermus Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10666 Verbesina virginica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2840 Podocarpus minor Species Podocarpaceae 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]
NPO9166 Monascus rubropunctatus Species Fellodistomidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO964 Homalium laurifolium Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9950 Coelogyne nitida Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO984 Hippocrepis emerus 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]
NPO7158 Schefflera venulosa Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18852 Plenckia populnea Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12488 Bupleurum rigidum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO230 Palisota barteri Species Commelinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11024 Bellardia viscosa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11511 Cochlearia officinalis Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23642 Penicillium tardum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22661 Pinus aristata Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO43 Leifsonia aquatica Species Microbacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13234 Gyalolechia fulgida Species Teloschistaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6544 Carpesium longifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11137 Dichotomanthes tristaniicarpa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17547 Dryopteris arguta Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 27.0 % PMID[525404]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 50.0 % PMID[525404]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 54.0 % PMID[525404]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 66.0 % PMID[525404]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 19.5 % PMID[525405]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 28.1 % PMID[525405]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 31.8 % PMID[525405]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 20.4 % PMID[525405]
NPT2794 Individual Protein Quinolone resistance protein norA Staphylococcus aureus FC = 2.0 n.a. PMID[525406]
NPT2794 Individual Protein Quinolone resistance protein norA Staphylococcus aureus FC = 0.0 n.a. PMID[525406]
NPT2794 Individual Protein Quinolone resistance protein norA Staphylococcus aureus MIC > 100.0 ug.mL-1 PMID[525407]
NPT2794 Individual Protein Quinolone resistance protein norA Staphylococcus aureus MEC = 25.0 ug ml-1 PMID[525407]
NPT2794 Individual Protein Quinolone resistance protein norA Staphylococcus aureus PF = 60.0 n.a. PMID[525407]
NPT2794 Individual Protein Quinolone resistance protein norA Staphylococcus aureus logPF = 1.78 n.a. PMID[525407]
NPT2794 Individual Protein Quinolone resistance protein norA Staphylococcus aureus FC = 2.0 n.a. PMID[525407]
NPT1460 Cell Line L929 Mus musculus Inhibition = 25.0 % PMID[525408]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = -14.0 % PMID[525408]
NPT1460 Cell Line L929 Mus musculus Inhibition = 16.0 % PMID[525408]
NPT1460 Cell Line L929 Mus musculus Inhibition = 23.0 % PMID[525408]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 7.0 % PMID[525408]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 10.0 % PMID[525408]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 66.0 % PMID[525408]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 27.0 % PMID[525408]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 50.0 % PMID[525408]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 54.0 % PMID[525408]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 13.0 % PMID[525408]
NPT472 Individual Protein Vanilloid receptor Homo sapiens EC50 = 6.31 nM PMID[525410]
NPT472 Individual Protein Vanilloid receptor Homo sapiens Emax = 94.0 % PMID[525410]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 18348.9 nM PMID[525411]
NPT393 Cell Line HCT-116 Homo sapiens IC50 > 20000.0 nM PMID[525412]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 23109.3 nM PMID[525411]
NPT157 Individual Protein Breast cancer type 1 susceptibility protein Homo sapiens Potency n.a. 17782.8 nM PMID[525411]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 25929.0 nM PMID[525411]
NPT160 Individual Protein TAR DNA-binding protein 43 Homo sapiens Potency n.a. 8912.5 nM PMID[525411]
NPT487 Organism Cladosporium cladosporioides Cladosporium cladosporioides MIC = 1.0 ug PMID[525403]
NPT488 Organism Cladosporium sphaerospermum Cladosporium sphaerospermum MIC = 1.0 ug PMID[525403]
NPT2 Others Unspecified Activity = -10.0 % PMID[525409]
NPT2 Others Unspecified Potency n.a. 20596.2 nM PMID[525411]
NPT692 Individual Protein Histone deacetylase 6 Homo sapiens Inhibition < 50.0 % PMID[525412]
NPT963 Organism Hepatitis B virus Hepatitis B virus IC50 > 4510000.0 nM PMID[525413]
NPT27 Others Unspecified CC50 = 320000.0 nM PMID[525413]
NPT2 Others Unspecified Potency n.a. 14125.4 nM PMID[525411]

☑ 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 NPC207541 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC170583
1.0 High Similarity NPC182147
1.0 High Similarity NPC246133
1.0 High Similarity NPC152186
1.0 High Similarity NPC71105
0.9916 High Similarity NPC251466
0.9916 High Similarity NPC156944
0.9915 High Similarity NPC300955
0.9833 High Similarity NPC157740
0.9833 High Similarity NPC99798
0.9833 High Similarity NPC291449
0.9833 High Similarity NPC41331
0.9752 High Similarity NPC147247
0.9752 High Similarity NPC246974
0.9508 High Similarity NPC191302
0.9355 High Similarity NPC470706
0.9274 High Similarity NPC469977
0.9213 High Similarity NPC473463
0.9213 High Similarity NPC284855
0.9213 High Similarity NPC282477
0.8661 High Similarity NPC301713
0.8657 High Similarity NPC275150
0.8594 High Similarity NPC186898
0.8594 High Similarity NPC153990
0.8571 High Similarity NPC254610
0.8571 High Similarity NPC166837
0.8559 High Similarity NPC127326
0.8527 High Similarity NPC155838
0.8462 Intermediate Similarity NPC35961
0.8462 Intermediate Similarity NPC195749
0.8462 Intermediate Similarity NPC52029
0.8425 Intermediate Similarity NPC249788
0.8406 Intermediate Similarity NPC327623
0.8397 Intermediate Similarity NPC255550
0.8397 Intermediate Similarity NPC308885
0.8333 Intermediate Similarity NPC31279
0.8333 Intermediate Similarity NPC214869
0.831 Intermediate Similarity NPC474560
0.8308 Intermediate Similarity NPC251571
0.8258 Intermediate Similarity NPC114102
0.8254 Intermediate Similarity NPC344161
0.8231 Intermediate Similarity NPC274356
0.8209 Intermediate Similarity NPC218530
0.8195 Intermediate Similarity NPC130595
0.8195 Intermediate Similarity NPC93882
0.8175 Intermediate Similarity NPC69670
0.8175 Intermediate Similarity NPC57501
0.8175 Intermediate Similarity NPC77572
0.8145 Intermediate Similarity NPC303370
0.8134 Intermediate Similarity NPC285078
0.8134 Intermediate Similarity NPC313737
0.8134 Intermediate Similarity NPC6854
0.8125 Intermediate Similarity NPC114845
0.8125 Intermediate Similarity NPC301641
0.8125 Intermediate Similarity NPC80241
0.8083 Intermediate Similarity NPC227894
0.806 Intermediate Similarity NPC318862
0.8049 Intermediate Similarity NPC165646
0.8047 Intermediate Similarity NPC183262
0.8029 Intermediate Similarity NPC41473
0.8029 Intermediate Similarity NPC312770
0.8029 Intermediate Similarity NPC14600
0.8029 Intermediate Similarity NPC204848
0.8029 Intermediate Similarity NPC470707
0.8029 Intermediate Similarity NPC160607
0.8016 Intermediate Similarity NPC199209
0.8016 Intermediate Similarity NPC212643
0.8016 Intermediate Similarity NPC33271
0.7985 Intermediate Similarity NPC275950
0.7971 Intermediate Similarity NPC299583
0.7971 Intermediate Similarity NPC296898
0.7967 Intermediate Similarity NPC55300
0.7966 Intermediate Similarity NPC12714
0.7966 Intermediate Similarity NPC310905
0.7955 Intermediate Similarity NPC213711
0.7955 Intermediate Similarity NPC40352
0.7951 Intermediate Similarity NPC233731
0.7951 Intermediate Similarity NPC246358
0.7951 Intermediate Similarity NPC7097
0.7951 Intermediate Similarity NPC36108
0.7941 Intermediate Similarity NPC94280
0.7941 Intermediate Similarity NPC159150
0.7941 Intermediate Similarity NPC328419
0.7941 Intermediate Similarity NPC193673
0.7941 Intermediate Similarity NPC45783
0.7941 Intermediate Similarity NPC103947
0.7937 Intermediate Similarity NPC111225
0.7926 Intermediate Similarity NPC476345
0.7923 Intermediate Similarity NPC256167
0.791 Intermediate Similarity NPC470633
0.791 Intermediate Similarity NPC228769
0.7907 Intermediate Similarity NPC83279
0.7891 Intermediate Similarity NPC256369
0.7891 Intermediate Similarity NPC119949
0.7886 Intermediate Similarity NPC137685
0.7883 Intermediate Similarity NPC136330
0.7883 Intermediate Similarity NPC196609
0.7883 Intermediate Similarity NPC255817
0.7883 Intermediate Similarity NPC230698
0.7883 Intermediate Similarity NPC251454
0.7883 Intermediate Similarity NPC96406
0.7883 Intermediate Similarity NPC205178
0.7883 Intermediate Similarity NPC73883
0.7883 Intermediate Similarity NPC180647
0.7883 Intermediate Similarity NPC277042
0.7879 Intermediate Similarity NPC17348
0.7868 Intermediate Similarity NPC219671
0.7868 Intermediate Similarity NPC471505
0.7868 Intermediate Similarity NPC227002
0.7868 Intermediate Similarity NPC147616
0.7868 Intermediate Similarity NPC104077
0.7868 Intermediate Similarity NPC106739
0.7868 Intermediate Similarity NPC259742
0.7852 Intermediate Similarity NPC173308
0.7852 Intermediate Similarity NPC63574
0.7852 Intermediate Similarity NPC181079
0.7833 Intermediate Similarity NPC292792
0.7829 Intermediate Similarity NPC263835
0.7826 Intermediate Similarity NPC145446
0.7826 Intermediate Similarity NPC99078
0.7826 Intermediate Similarity NPC137172
0.7823 Intermediate Similarity NPC173746
0.7823 Intermediate Similarity NPC257124
0.7823 Intermediate Similarity NPC78918
0.7823 Intermediate Similarity NPC139617
0.7823 Intermediate Similarity NPC156840
0.7823 Intermediate Similarity NPC8547
0.781 Intermediate Similarity NPC167096
0.781 Intermediate Similarity NPC169973
0.7795 Intermediate Similarity NPC258992
0.7794 Intermediate Similarity NPC217574
0.7787 Intermediate Similarity NPC258171
0.7778 Intermediate Similarity NPC294941
0.777 Intermediate Similarity NPC220923
0.777 Intermediate Similarity NPC28641
0.777 Intermediate Similarity NPC95366
0.777 Intermediate Similarity NPC248505
0.777 Intermediate Similarity NPC194359
0.777 Intermediate Similarity NPC252107
0.777 Intermediate Similarity NPC225745
0.7761 Intermediate Similarity NPC158737
0.7761 Intermediate Similarity NPC64948
0.7761 Intermediate Similarity NPC177167
0.7752 Intermediate Similarity NPC310338
0.7752 Intermediate Similarity NPC43275
0.7752 Intermediate Similarity NPC281298
0.7737 Intermediate Similarity NPC252833
0.7737 Intermediate Similarity NPC97316
0.7734 Intermediate Similarity NPC120075
0.7734 Intermediate Similarity NPC164386
0.7734 Intermediate Similarity NPC280001
0.773 Intermediate Similarity NPC195814
0.7727 Intermediate Similarity NPC31344
0.7727 Intermediate Similarity NPC13020
0.7727 Intermediate Similarity NPC317769
0.7727 Intermediate Similarity NPC140359
0.7724 Intermediate Similarity NPC146530
0.7721 Intermediate Similarity NPC184814
0.7721 Intermediate Similarity NPC134764
0.7721 Intermediate Similarity NPC171550
0.771 Intermediate Similarity NPC193484
0.7704 Intermediate Similarity NPC226862
0.7704 Intermediate Similarity NPC158471
0.7704 Intermediate Similarity NPC57119
0.7704 Intermediate Similarity NPC165128
0.7698 Intermediate Similarity NPC184938
0.7698 Intermediate Similarity NPC165106
0.7698 Intermediate Similarity NPC135777
0.7698 Intermediate Similarity NPC101624
0.7698 Intermediate Similarity NPC174191
0.7698 Intermediate Similarity NPC142547
0.7692 Intermediate Similarity NPC53596
0.7692 Intermediate Similarity NPC227217
0.7692 Intermediate Similarity NPC289330
0.7692 Intermediate Similarity NPC17388
0.7692 Intermediate Similarity NPC471308
0.7692 Intermediate Similarity NPC117780
0.7692 Intermediate Similarity NPC95614
0.7692 Intermediate Similarity NPC165133
0.7692 Intermediate Similarity NPC160120
0.7692 Intermediate Similarity NPC232316
0.7692 Intermediate Similarity NPC56214
0.7692 Intermediate Similarity NPC242885
0.7687 Intermediate Similarity NPC473960
0.7681 Intermediate Similarity NPC471390
0.7681 Intermediate Similarity NPC25821
0.7681 Intermediate Similarity NPC471391
0.7681 Intermediate Similarity NPC196937
0.7681 Intermediate Similarity NPC6836
0.7676 Intermediate Similarity NPC100478
0.7676 Intermediate Similarity NPC222039
0.7674 Intermediate Similarity NPC470626
0.7674 Intermediate Similarity NPC474040
0.7652 Intermediate Similarity NPC298486
0.7647 Intermediate Similarity NPC307110
0.7647 Intermediate Similarity NPC476748
0.7647 Intermediate Similarity NPC248355
0.7643 Intermediate Similarity NPC193528
0.7639 Intermediate Similarity NPC5462
0.763 Intermediate Similarity NPC100129

  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 NPC207541 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
0.8468 Intermediate Similarity NPD1357 Approved
0.8397 Intermediate Similarity NPD3144 Approved
0.8397 Intermediate Similarity NPD3145 Approved
0.8195 Intermediate Similarity NPD2674 Phase 3
0.7971 Intermediate Similarity NPD2161 Phase 2
0.7939 Intermediate Similarity NPD2922 Phase 1
0.7926 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7883 Intermediate Similarity NPD2492 Phase 1
0.7846 Intermediate Similarity NPD3705 Approved
0.7838 Intermediate Similarity NPD5563 Clinical (unspecified phase)
0.7823 Intermediate Similarity NPD228 Approved
0.7794 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD1375 Discontinued
0.7778 Intermediate Similarity NPD4739 Approved
0.777 Intermediate Similarity NPD4108 Discontinued
0.7746 Intermediate Similarity NPD6331 Phase 2
0.771 Intermediate Similarity NPD776 Approved
0.7698 Intermediate Similarity NPD5283 Phase 1
0.7682 Intermediate Similarity NPD5604 Discontinued
0.7651 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7606 Intermediate Similarity NPD7153 Discontinued
0.7594 Intermediate Similarity NPD3685 Discontinued
0.7594 Intermediate Similarity NPD1669 Approved
0.7594 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.7591 Intermediate Similarity NPD5109 Approved
0.7591 Intermediate Similarity NPD5110 Phase 2
0.7591 Intermediate Similarity NPD5111 Phase 2
0.7569 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1712 Approved
0.75 Intermediate Similarity NPD2157 Approved
0.7448 Intermediate Similarity NPD2219 Phase 1
0.7445 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD709 Approved
0.7415 Intermediate Similarity NPD4123 Phase 3
0.7397 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD2978 Approved
0.7368 Intermediate Similarity NPD2977 Approved
0.7365 Intermediate Similarity NPD7526 Approved
0.7365 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD52 Approved
0.7347 Intermediate Similarity NPD4357 Discontinued
0.7344 Intermediate Similarity NPD821 Approved
0.7338 Intermediate Similarity NPD5718 Phase 2
0.7333 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7328 Intermediate Similarity NPD5536 Phase 2
0.7315 Intermediate Similarity NPD2122 Discontinued
0.731 Intermediate Similarity NPD4236 Phase 3
0.731 Intermediate Similarity NPD4237 Approved
0.7293 Intermediate Similarity NPD2668 Approved
0.7293 Intermediate Similarity NPD2667 Approved
0.7259 Intermediate Similarity NPD2233 Approved
0.7259 Intermediate Similarity NPD2230 Approved
0.7259 Intermediate Similarity NPD2232 Approved
0.7255 Intermediate Similarity NPD5772 Approved
0.7255 Intermediate Similarity NPD5773 Approved
0.7254 Intermediate Similarity NPD2653 Approved
0.7248 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD4993 Discontinued
0.7246 Intermediate Similarity NPD2040 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD1558 Phase 1
0.7226 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD6895 Approved
0.7203 Intermediate Similarity NPD6896 Approved
0.7192 Intermediate Similarity NPD3060 Approved
0.7174 Intermediate Similarity NPD6584 Phase 3
0.7171 Intermediate Similarity NPD4675 Approved
0.7171 Intermediate Similarity NPD4678 Approved
0.7165 Intermediate Similarity NPD2684 Approved
0.7153 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD1772 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD1044 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD5241 Discontinued
0.7092 Intermediate Similarity NPD1048 Approved
0.7083 Intermediate Similarity NPD6111 Discontinued
0.708 Intermediate Similarity NPD2982 Phase 2
0.708 Intermediate Similarity NPD2983 Phase 2
0.7075 Intermediate Similarity NPD4162 Approved
0.7075 Intermediate Similarity NPD5177 Phase 3
0.7067 Intermediate Similarity NPD1771 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD3656 Approved
0.7042 Intermediate Similarity NPD839 Approved
0.7042 Intermediate Similarity NPD840 Approved
0.7027 Intermediate Similarity NPD4110 Phase 3
0.7027 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD1024 Discontinued
0.7021 Intermediate Similarity NPD3027 Phase 3
0.7014 Intermediate Similarity NPD4097 Suspended
0.7008 Intermediate Similarity NPD3134 Approved
0.7007 Intermediate Similarity NPD2337 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD2981 Phase 2
0.7007 Intermediate Similarity NPD2231 Phase 2
0.7007 Intermediate Similarity NPD1372 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD2808 Discontinued
0.7007 Intermediate Similarity NPD2235 Phase 2
0.6993 Remote Similarity NPD3620 Phase 2
0.6993 Remote Similarity NPD3111 Phase 1
0.6993 Remote Similarity NPD4005 Discontinued
0.6993 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6987 Remote Similarity NPD2358 Clinical (unspecified phase)
0.6977 Remote Similarity NPD556 Approved
0.6964 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6957 Remote Similarity NPD6583 Phase 3
0.6957 Remote Similarity NPD6582 Phase 2
0.6953 Remote Similarity NPD1358 Approved
0.6947 Remote Similarity NPD7843 Approved
0.6928 Remote Similarity NPD4210 Discontinued
0.6928 Remote Similarity NPD3687 Approved
0.6928 Remote Similarity NPD3686 Approved
0.6923 Remote Similarity NPD1423 Approved
0.6917 Remote Similarity NPD7157 Approved
0.6912 Remote Similarity NPD2423 Clinical (unspecified phase)
0.6912 Remote Similarity NPD4626 Approved
0.6903 Remote Similarity NPD5089 Approved
0.6903 Remote Similarity NPD5090 Approved
0.6901 Remote Similarity NPD3166 Approved
0.6901 Remote Similarity NPD3164 Approved
0.6901 Remote Similarity NPD3165 Approved
0.6901 Remote Similarity NPD3167 Approved
0.6897 Remote Similarity NPD4579 Clinical (unspecified phase)
0.6892 Remote Similarity NPD4664 Clinical (unspecified phase)
0.6889 Remote Similarity NPD1182 Approved
0.6887 Remote Similarity NPD5297 Approved
0.6885 Remote Similarity NPD9296 Approved
0.6879 Remote Similarity NPD9494 Approved
0.6879 Remote Similarity NPD2250 Discontinued
0.6879 Remote Similarity NPD3018 Phase 2
0.6875 Remote Similarity NPD2238 Phase 2
0.6866 Remote Similarity NPD3596 Phase 2
0.6857 Remote Similarity NPD1817 Approved
0.6857 Remote Similarity NPD1819 Approved
0.6857 Remote Similarity NPD1820 Approved
0.6857 Remote Similarity NPD1818 Approved
0.6853 Remote Similarity NPD1039 Discontinued
0.6846 Remote Similarity NPD3021 Approved
0.6846 Remote Similarity NPD3022 Approved
0.6839 Remote Similarity NPD7028 Phase 2
0.6839 Remote Similarity NPD1642 Discontinued
0.6821 Remote Similarity NPD7124 Phase 2
0.6818 Remote Similarity NPD9379 Approved
0.6818 Remote Similarity NPD9377 Approved
0.6813 Remote Similarity NPD2644 Approved
0.6806 Remote Similarity NPD3058 Clinical (unspecified phase)
0.6794 Remote Similarity NPD9280 Clinical (unspecified phase)
0.6792 Remote Similarity NPD4055 Discovery
0.679 Remote Similarity NPD4083 Discontinued
0.6783 Remote Similarity NPD3179 Approved
0.6783 Remote Similarity NPD3180 Approved
0.6779 Remote Similarity NPD4149 Clinical (unspecified phase)
0.6779 Remote Similarity NPD7037 Approved
0.6772 Remote Similarity NPD2560 Approved
0.6772 Remote Similarity NPD2563 Approved
0.677 Remote Similarity NPD2821 Approved
0.6765 Remote Similarity NPD6580 Approved
0.6765 Remote Similarity NPD6581 Approved
0.6761 Remote Similarity NPD2407 Clinical (unspecified phase)
0.6752 Remote Similarity NPD37 Approved
0.6752 Remote Similarity NPD5722 Discontinued
0.6744 Remote Similarity NPD1445 Approved
0.6744 Remote Similarity NPD1444 Approved
0.6739 Remote Similarity NPD3847 Discontinued
0.6735 Remote Similarity NPD7119 Phase 2
0.6732 Remote Similarity NPD1754 Clinical (unspecified phase)
0.6732 Remote Similarity NPD3688 Clinical (unspecified phase)
0.6732 Remote Similarity NPD3146 Approved
0.6725 Remote Similarity NPD3408 Clinical (unspecified phase)
0.6715 Remote Similarity NPD6830 Clinical (unspecified phase)
0.6714 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6712 Remote Similarity NPD3657 Discovery
0.6711 Remote Similarity NPD5756 Phase 2
0.6708 Remote Similarity NPD7201 Clinical (unspecified phase)
0.6707 Remote Similarity NPD5602 Clinical (unspecified phase)
0.6692 Remote Similarity NPD290 Approved
0.6692 Remote Similarity NPD1138 Approved
0.6691 Remote Similarity NPD1091 Approved
0.669 Remote Similarity NPD3163 Approved
0.669 Remote Similarity NPD3530 Approved
0.669 Remote Similarity NPD3532 Approved
0.669 Remote Similarity NPD558 Phase 2
0.669 Remote Similarity NPD3531 Approved
0.669 Remote Similarity NPD3162 Approved
0.669 Remote Similarity NPD7477 Discontinued
0.6689 Remote Similarity NPD5481 Discontinued
0.6689 Remote Similarity NPD3693 Clinical (unspecified phase)
0.6688 Remote Similarity NPD1351 Approved
0.6688 Remote Similarity NPD3647 Clinical (unspecified phase)
0.6688 Remote Similarity NPD1349 Approved
0.6688 Remote Similarity NPD1350 Approved
0.6687 Remote Similarity NPD7833 Phase 2
0.6687 Remote Similarity NPD7831 Phase 2
0.6687 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6667 Remote Similarity NPD824 Approved
0.6667 Remote Similarity NPD6387 Discontinued
0.6667 Remote Similarity NPD2557 Approved
0.6667 Remote Similarity NPD3655 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7258 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data