Structure

Physi-Chem Properties

Molecular Weight:  352.13
Volume:  366.326
LogP:  4.268
LogD:  3.563
LogS:  -4.948
# Rotatable Bonds:  3
TPSA:  64.99
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.637
Synthetic Accessibility Score:  2.993
Fsp3:  0.19
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.957
MDCK Permeability:  1.6626701835775748e-05
Pgp-inhibitor:  0.009
Pgp-substrate:  0.076
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.069
Plasma Protein Binding (PPB):  99.44820404052734%
Volume Distribution (VD):  0.484
Pgp-substrate:  1.53543221950531%

ADMET: Metabolism

CYP1A2-inhibitor:  0.959
CYP1A2-substrate:  0.822
CYP2C19-inhibitor:  0.922
CYP2C19-substrate:  0.224
CYP2C9-inhibitor:  0.822
CYP2C9-substrate:  0.931
CYP2D6-inhibitor:  0.756
CYP2D6-substrate:  0.89
CYP3A4-inhibitor:  0.62
CYP3A4-substrate:  0.403

ADMET: Excretion

Clearance (CL):  7.96
Half-life (T1/2):  0.562

ADMET: Toxicity

hERG Blockers:  0.031
Human Hepatotoxicity (H-HT):  0.016
Drug-inuced Liver Injury (DILI):  0.347
AMES Toxicity:  0.853
Rat Oral Acute Toxicity:  0.82
Maximum Recommended Daily Dose:  0.912
Skin Sensitization:  0.878
Carcinogencity:  0.937
Eye Corrosion:  0.004
Eye Irritation:  0.927
Respiratory Toxicity:  0.782

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  Natural Product: NPC298802

Natural Product ID:  NPC298802
Common Name*:   Delta-1',3'-1'-Dehydroxypenicillide
IUPAC Name:   6-hydroxy-1-methoxy-8-methyl-2-[(1E)-3-methylbuta-1,3-dienyl]-10H-benzo[b][1,5]benzodioxocin-12-one
Synonyms:  
Standard InCHIKey:  XBAIUNZIMJALOJ-AATRIKPKSA-N
Standard InCHI:  InChI=1S/C21H20O5/c1-12(2)5-6-14-7-8-17-18(20(14)24-4)21(23)25-11-15-9-13(3)10-16(22)19(15)26-17/h5-10,22H,1,11H2,2-4H3/b6-5+
SMILES:  COc1c(/C=C/C(=C)C)ccc2c1C(=O)OCc1c(O2)c(O)cc(c1)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2164945
PubChem CID:   71451577
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000254] Ethers
          • [CHEMONTID:0002463] Diarylethers

*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
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. twig n.a. DOI[10.1021/np50063a031]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. stem n.a. DOI[10.1021/np50063a031]
NPO16456 Mirabilis jalapa Species Nyctaginaceae Eukaryota n.a. n.a. n.a. PMID[11277746]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[15165134]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. stem n.a. PMID[16254827]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. twig n.a. PMID[16254827]
NPO16566 Cinnamosma madagascariensis Species Canellaceae Eukaryota n.a. n.a. n.a. PMID[18179176]
NPO17999 Sonneratia alba Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[19835393]
NPO22097 Plakinastrella clathrata Species Plakinidae Eukaryota n.a. n.a. n.a. PMID[21261297]
NPO16812 Ajuga bracteosa Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[21539300]
NPO9189 Streptomyces atratus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21868221]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[22316191]
NPO40990 Penicillium sp. MA-37 Strain Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23148724]
NPO5119 Pseudomonas chlororaphis Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[25679537]
NPO5119 Pseudomonas chlororaphis Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[25901993]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[2778454]
NPO15599 Daldinia concentrica Species n.a. Eukaryota Fruiting Bodies n.a. n.a. PMID[29715021]
NPO16455 Xylopia aethiopica Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[8158166]
NPO15004 Artemisia taurica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16456 Mirabilis jalapa Species Nyctaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26788 Sophora viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14575 Periploca forrestii Species Cosmopterigidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8010 Otostegia fruticosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16456 Mirabilis jalapa Species Nyctaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15004 Artemisia taurica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26788 Sophora viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14575 Periploca forrestii Species Cosmopterigidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4507 Bruguiera gymnorhiza Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21437 Rhododendron aureum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11760 Teucrium orientale Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15004 Artemisia taurica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15599 Daldinia concentrica Species n.a. Eukaryota n.a. n.a. n.a. Database[Title]
NPO9189 Streptomyces atratus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO15545 Veltheimia viridifolia Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO84 Isoberlinia angolensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15004 Artemisia taurica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17304 Sipunculus nudus Species Sipunculidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13789 Paranephelius uniflorus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14575 Periploca forrestii Species Cosmopterigidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22097 Plakinastrella clathrata Species Plakinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10770 Ptilota pectinata Species Ceramiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14002 Petalostemon purpureum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11408 Podocarpus amarus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17921 Allium monspessulanum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17145 Aegiceras corniculatum Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16215 Umbilicaria cinereorufescens Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26788 Sophora viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15919 Streptomyces caelestis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO21437 Rhododendron aureum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16923 Cereus chrysacanthus Species Sagartiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17071 Coeloseira pacifica Species Champiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17999 Sonneratia alba Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16566 Cinnamosma madagascariensis Species Canellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17375 Ceramium botryocarpum Species Ceramiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28319 Ulva prolifera Species Ulvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17339 Macaranga sinensis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16456 Mirabilis jalapa Species Nyctaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16455 Xylopia aethiopica Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4336 Echiochilon pauciflorum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28868 Pardachirus pavoninus Species Soleidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17218 Helichrysum nudifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15599 Daldinia concentrica Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5119 Pseudomonas chlororaphis Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO25550 Buchenavia tetraphylla Species Combretaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16052 Chromodoris obsoleta Species Chromodorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2155 Tephroseris integrifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14813 Agaricus silvaticus Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15748 Hypoxis nyasica Species Hypoxidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16812 Ajuga bracteosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28821 Stichopus horrens Species Stichopodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17844 Agaricus integer Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17602 Arbutus menziesii Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13013 Saccharothrix mutabilis Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO16695 Fumaria kraliki Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4507 Bruguiera gymnorhiza Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16329 Potebniamyces gallicola Species Phacidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7905 Lepista irina Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8010 Otostegia fruticosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2550 Trichoderma citrinum Species Hypocreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9951 Hyella caespitosa Species Hyellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11760 Teucrium orientale Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18073 Justicia trinervia Species Acanthaceae 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
NPT140 Organism Artemia Artemia LD50 = 135.9 uM PMID[540509]

☑ 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 NPC298802 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
0.9932 High Similarity NPC286052
0.9796 High Similarity NPC199773
0.9669 High Similarity NPC292415
0.9605 High Similarity NPC103201
0.9605 High Similarity NPC349525
0.9605 High Similarity NPC473106
0.9221 High Similarity NPC83763
0.9221 High Similarity NPC168616
0.9216 High Similarity NPC278778
0.9216 High Similarity NPC35038
0.9216 High Similarity NPC291878
0.9216 High Similarity NPC195796
0.9156 High Similarity NPC474055
0.9156 High Similarity NPC27337
0.9156 High Similarity NPC291508
0.9156 High Similarity NPC472598
0.915 High Similarity NPC470327
0.915 High Similarity NPC45849
0.915 High Similarity NPC477503
0.915 High Similarity NPC200761
0.9145 High Similarity NPC471982
0.9145 High Similarity NPC289968
0.9139 High Similarity NPC225129
0.9108 High Similarity NPC234004
0.9091 High Similarity NPC209614
0.9091 High Similarity NPC472456
0.9091 High Similarity NPC472626
0.9091 High Similarity NPC470328
0.9085 High Similarity NPC192083
0.9085 High Similarity NPC475895
0.9085 High Similarity NPC18727
0.9085 High Similarity NPC213896
0.9045 High Similarity NPC8300
0.9038 High Similarity NPC36217
0.9038 High Similarity NPC118256
0.9038 High Similarity NPC282009
0.9038 High Similarity NPC119209
0.9038 High Similarity NPC472624
0.9038 High Similarity NPC192686
0.9038 High Similarity NPC287328
0.9032 High Similarity NPC222689
0.9032 High Similarity NPC223787
0.9032 High Similarity NPC108456
0.9032 High Similarity NPC78225
0.9032 High Similarity NPC35598
0.9026 High Similarity NPC321779
0.9026 High Similarity NPC234255
0.9026 High Similarity NPC226025
0.9026 High Similarity NPC152951
0.9026 High Similarity NPC117992
0.9026 High Similarity NPC230149
0.9026 High Similarity NPC57674
0.9026 High Similarity NPC168247
0.902 High Similarity NPC236637
0.902 High Similarity NPC302950
0.902 High Similarity NPC472912
0.902 High Similarity NPC106976
0.902 High Similarity NPC219582
0.9013 High Similarity NPC88804
0.9013 High Similarity NPC3825
0.8981 High Similarity NPC472634
0.8981 High Similarity NPC471499
0.8981 High Similarity NPC26326
0.8981 High Similarity NPC474038
0.8981 High Similarity NPC472632
0.8981 High Similarity NPC112418
0.8981 High Similarity NPC266314
0.8981 High Similarity NPC471210
0.8974 High Similarity NPC74178
0.8974 High Similarity NPC184755
0.8974 High Similarity NPC250214
0.8974 High Similarity NPC95936
0.8974 High Similarity NPC22192
0.8968 High Similarity NPC227062
0.8968 High Similarity NPC471985
0.8968 High Similarity NPC472455
0.8968 High Similarity NPC54928
0.8968 High Similarity NPC191146
0.8968 High Similarity NPC68093
0.8961 High Similarity NPC49402
0.8961 High Similarity NPC298692
0.8961 High Similarity NPC33051
0.8961 High Similarity NPC70433
0.8961 High Similarity NPC227337
0.8961 High Similarity NPC74924
0.8961 High Similarity NPC273462
0.8954 High Similarity NPC256406
0.8947 High Similarity NPC223579
0.8947 High Similarity NPC287101
0.8947 High Similarity NPC177298
0.8947 High Similarity NPC48479
0.8947 High Similarity NPC183950
0.8947 High Similarity NPC137062
0.8947 High Similarity NPC52005
0.8931 High Similarity NPC85057
0.8931 High Similarity NPC130920
0.8924 High Similarity NPC472635
0.8924 High Similarity NPC471745
0.8924 High Similarity NPC201800
0.8924 High Similarity NPC474034
0.8924 High Similarity NPC474162
0.8924 High Similarity NPC476247
0.8924 High Similarity NPC474150
0.8924 High Similarity NPC474033
0.8917 High Similarity NPC471744
0.8917 High Similarity NPC475784
0.8917 High Similarity NPC470326
0.8917 High Similarity NPC476980
0.8917 High Similarity NPC472631
0.8917 High Similarity NPC472630
0.8917 High Similarity NPC174953
0.8917 High Similarity NPC328102
0.8917 High Similarity NPC130955
0.891 High Similarity NPC284820
0.891 High Similarity NPC474208
0.891 High Similarity NPC156057
0.891 High Similarity NPC67876
0.891 High Similarity NPC474836
0.891 High Similarity NPC471515
0.891 High Similarity NPC471479
0.891 High Similarity NPC129684
0.891 High Similarity NPC471209
0.891 High Similarity NPC472910
0.891 High Similarity NPC48208
0.891 High Similarity NPC36852
0.891 High Similarity NPC472914
0.891 High Similarity NPC299520
0.891 High Similarity NPC262286
0.891 High Similarity NPC475267
0.891 High Similarity NPC96167
0.891 High Similarity NPC472911
0.891 High Similarity NPC52889
0.891 High Similarity NPC222814
0.891 High Similarity NPC162869
0.891 High Similarity NPC472913
0.891 High Similarity NPC245758
0.891 High Similarity NPC473272
0.8903 High Similarity NPC256925
0.8903 High Similarity NPC472280
0.8903 High Similarity NPC133392
0.8903 High Similarity NPC213622
0.8896 High Similarity NPC157784
0.8896 High Similarity NPC477231
0.8896 High Similarity NPC237994
0.8896 High Similarity NPC39732
0.8896 High Similarity NPC257648
0.8896 High Similarity NPC63187
0.8896 High Similarity NPC60972
0.8896 High Similarity NPC474656
0.8896 High Similarity NPC37684
0.8896 High Similarity NPC260979
0.8889 High Similarity NPC338131
0.8889 High Similarity NPC213382
0.8889 High Similarity NPC472279
0.8889 High Similarity NPC164527
0.8882 High Similarity NPC195202
0.8882 High Similarity NPC120464
0.8875 High Similarity NPC207575
0.8875 High Similarity NPC13481
0.8875 High Similarity NPC472452
0.8868 High Similarity NPC156082
0.8868 High Similarity NPC124038
0.8868 High Similarity NPC186686
0.8868 High Similarity NPC472625
0.8861 High Similarity NPC142252
0.8861 High Similarity NPC471212
0.8861 High Similarity NPC134783
0.8861 High Similarity NPC471211
0.8861 High Similarity NPC258331
0.8854 High Similarity NPC204879
0.8854 High Similarity NPC210459
0.8854 High Similarity NPC117418
0.8854 High Similarity NPC473990
0.8854 High Similarity NPC53545
0.8854 High Similarity NPC238381
0.8846 High Similarity NPC320825
0.8846 High Similarity NPC235165
0.8846 High Similarity NPC170026
0.8846 High Similarity NPC255106
0.8846 High Similarity NPC326037
0.8846 High Similarity NPC138243
0.8846 High Similarity NPC13858
0.8846 High Similarity NPC471500
0.8846 High Similarity NPC472916
0.8846 High Similarity NPC282307
0.8839 High Similarity NPC69394
0.8839 High Similarity NPC47781
0.8839 High Similarity NPC231018
0.8839 High Similarity NPC183878
0.8839 High Similarity NPC176775
0.8839 High Similarity NPC236223
0.8839 High Similarity NPC255350
0.8839 High Similarity NPC78326
0.8839 High Similarity NPC170492
0.8839 High Similarity NPC160951
0.8839 High Similarity NPC469550
0.8839 High Similarity NPC270620
0.8839 High Similarity NPC22519
0.8839 High Similarity NPC179126
0.8839 High Similarity NPC274327

  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 NPC298802 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
0.9085 High Similarity NPD2393 Clinical (unspecified phase)
0.902 High Similarity NPD1934 Approved
0.8839 High Similarity NPD2801 Approved
0.8782 High Similarity NPD3817 Phase 2
0.8726 High Similarity NPD3882 Suspended
0.8618 High Similarity NPD1511 Approved
0.8608 High Similarity NPD4868 Clinical (unspecified phase)
0.858 High Similarity NPD6166 Phase 2
0.858 High Similarity NPD6168 Clinical (unspecified phase)
0.858 High Similarity NPD6167 Clinical (unspecified phase)
0.8571 High Similarity NPD6232 Discontinued
0.8553 High Similarity NPD7075 Discontinued
0.8506 High Similarity NPD1512 Approved
0.8485 Intermediate Similarity NPD7074 Phase 3
0.8481 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8476 Intermediate Similarity NPD3818 Discontinued
0.8442 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8424 Intermediate Similarity NPD7054 Approved
0.8415 Intermediate Similarity NPD7473 Discontinued
0.84 Intermediate Similarity NPD2935 Discontinued
0.8377 Intermediate Similarity NPD6799 Approved
0.8373 Intermediate Similarity NPD7472 Approved
0.8365 Intermediate Similarity NPD7819 Suspended
0.8333 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD5844 Phase 1
0.8302 Intermediate Similarity NPD6801 Discontinued
0.8291 Intermediate Similarity NPD4380 Phase 2
0.8278 Intermediate Similarity NPD1551 Phase 2
0.8261 Intermediate Similarity NPD7768 Phase 2
0.8255 Intermediate Similarity NPD447 Suspended
0.8239 Intermediate Similarity NPD7411 Suspended
0.8221 Intermediate Similarity NPD5494 Approved
0.8214 Intermediate Similarity NPD6797 Phase 2
0.8176 Intermediate Similarity NPD6599 Discontinued
0.8166 Intermediate Similarity NPD6559 Discontinued
0.8166 Intermediate Similarity NPD7251 Discontinued
0.816 Intermediate Similarity NPD919 Approved
0.8137 Intermediate Similarity NPD1465 Phase 2
0.8133 Intermediate Similarity NPD230 Phase 1
0.8118 Intermediate Similarity NPD7808 Phase 3
0.8105 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8105 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8098 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8089 Intermediate Similarity NPD2532 Approved
0.8089 Intermediate Similarity NPD2533 Approved
0.8089 Intermediate Similarity NPD2534 Approved
0.8086 Intermediate Similarity NPD5402 Approved
0.8052 Intermediate Similarity NPD1549 Phase 2
0.8052 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7988 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD3027 Phase 3
0.7987 Intermediate Similarity NPD5403 Approved
0.7975 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7974 Intermediate Similarity NPD1510 Phase 2
0.7949 Intermediate Similarity NPD3750 Approved
0.7947 Intermediate Similarity NPD1240 Approved
0.7947 Intermediate Similarity NPD1613 Approved
0.7947 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD6234 Discontinued
0.7933 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7922 Intermediate Similarity NPD2796 Approved
0.7919 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD1933 Approved
0.7885 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7862 Intermediate Similarity NPD5401 Approved
0.7857 Intermediate Similarity NPD2799 Discontinued
0.7852 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7844 Intermediate Similarity NPD1247 Approved
0.7844 Intermediate Similarity NPD6959 Discontinued
0.7843 Intermediate Similarity NPD1607 Approved
0.7838 Intermediate Similarity NPD1203 Approved
0.7834 Intermediate Similarity NPD4628 Phase 3
0.7829 Intermediate Similarity NPD943 Approved
0.7826 Intermediate Similarity NPD1653 Approved
0.7778 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7764 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7764 Intermediate Similarity NPD920 Approved
0.7744 Intermediate Similarity NPD37 Approved
0.774 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD7199 Phase 2
0.7722 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD4967 Phase 2
0.7711 Intermediate Similarity NPD4966 Approved
0.7711 Intermediate Similarity NPD4965 Approved
0.7697 Intermediate Similarity NPD2313 Discontinued
0.7688 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD5953 Discontinued
0.7682 Intermediate Similarity NPD6832 Phase 2
0.7674 Intermediate Similarity NPD7286 Phase 2
0.7669 Intermediate Similarity NPD3226 Approved
0.7658 Intermediate Similarity NPD2800 Approved
0.7658 Intermediate Similarity NPD1243 Approved
0.7647 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD3926 Phase 2
0.7643 Intermediate Similarity NPD2346 Discontinued
0.764 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7635 Intermediate Similarity NPD9717 Approved
0.7628 Intermediate Similarity NPD3748 Approved
0.7625 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD7228 Approved
0.761 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD4060 Phase 1
0.7584 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD6190 Approved
0.756 Intermediate Similarity NPD3749 Approved
0.75 Intermediate Similarity NPD9494 Approved
0.7485 Intermediate Similarity NPD5711 Approved
0.7485 Intermediate Similarity NPD5710 Approved
0.747 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD411 Approved
0.7468 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD6798 Discontinued
0.7458 Intermediate Similarity NPD8313 Approved
0.7458 Intermediate Similarity NPD8312 Approved
0.745 Intermediate Similarity NPD422 Phase 1
0.7442 Intermediate Similarity NPD5242 Approved
0.7436 Intermediate Similarity NPD6355 Discontinued
0.74 Intermediate Similarity NPD9269 Phase 2
0.7389 Intermediate Similarity NPD6651 Approved
0.7374 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD2797 Approved
0.7366 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD7685 Pre-registration
0.7338 Intermediate Similarity NPD4908 Phase 1
0.7337 Intermediate Similarity NPD5353 Approved
0.7325 Intermediate Similarity NPD5124 Phase 1
0.7325 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD1019 Discontinued
0.7317 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD6233 Phase 2
0.7303 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD4308 Phase 3
0.7296 Intermediate Similarity NPD7033 Discontinued
0.7296 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD1608 Approved
0.7284 Intermediate Similarity NPD4110 Phase 3
0.7284 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD7229 Phase 3
0.7279 Intermediate Similarity NPD9493 Approved
0.7278 Intermediate Similarity NPD8455 Phase 2
0.7273 Intermediate Similarity NPD3018 Phase 2
0.7262 Intermediate Similarity NPD6385 Approved
0.7262 Intermediate Similarity NPD6386 Approved
0.725 Intermediate Similarity NPD5406 Approved
0.725 Intermediate Similarity NPD5408 Approved
0.725 Intermediate Similarity NPD5405 Approved
0.725 Intermediate Similarity NPD5404 Approved
0.7244 Intermediate Similarity NPD3268 Approved
0.7238 Intermediate Similarity NPD8434 Phase 2
0.7225 Intermediate Similarity NPD8127 Discontinued
0.7222 Intermediate Similarity NPD1652 Phase 2
0.7219 Intermediate Similarity NPD1610 Phase 2
0.7212 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD2344 Approved
0.7205 Intermediate Similarity NPD7266 Discontinued
0.7205 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD3225 Approved
0.7188 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD9545 Approved
0.7181 Intermediate Similarity NPD1548 Phase 1
0.7179 Intermediate Similarity NPD4625 Phase 3
0.7169 Intermediate Similarity NPD5049 Phase 3
0.7152 Intermediate Similarity NPD4357 Discontinued
0.7152 Intermediate Similarity NPD7390 Discontinued
0.7151 Intermediate Similarity NPD7240 Approved
0.7151 Intermediate Similarity NPD7038 Approved
0.7151 Intermediate Similarity NPD7039 Approved
0.7143 Intermediate Similarity NPD1164 Approved
0.7143 Intermediate Similarity NPD4476 Approved
0.7143 Intermediate Similarity NPD3455 Phase 2
0.7143 Intermediate Similarity NPD4477 Approved
0.7143 Intermediate Similarity NPD6099 Approved
0.7143 Intermediate Similarity NPD7458 Discontinued
0.7143 Intermediate Similarity NPD6100 Approved
0.7135 Intermediate Similarity NPD4288 Approved
0.7134 Intermediate Similarity NPD1296 Phase 2
0.7133 Intermediate Similarity NPD9268 Approved
0.7127 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD2983 Phase 2
0.7124 Intermediate Similarity NPD2982 Phase 2
0.7119 Intermediate Similarity NPD3751 Discontinued
0.7114 Intermediate Similarity NPD5536 Phase 2
0.7111 Intermediate Similarity NPD7549 Discontinued
0.7105 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD6005 Phase 3
0.7099 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD6002 Phase 3
0.7099 Intermediate Similarity NPD6004 Phase 3
0.7099 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD2798 Approved
0.7089 Intermediate Similarity NPD4062 Phase 3
0.7086 Intermediate Similarity NPD17 Approved
0.7086 Intermediate Similarity NPD3787 Discontinued
0.7086 Intermediate Similarity NPD1778 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