Structure

Physi-Chem Properties

Molecular Weight:  230.09
Volume:  244.139
LogP:  3.539
LogD:  3.226
LogS:  -4.714
# Rotatable Bonds:  3
TPSA:  39.44
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.755
Synthetic Accessibility Score:  2.489
Fsp3:  0.214
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.679
MDCK Permeability:  1.4591988474421669e-05
Pgp-inhibitor:  0.136
Pgp-substrate:  0.009
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.101

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.101
Plasma Protein Binding (PPB):  82.19805908203125%
Volume Distribution (VD):  1.352
Pgp-substrate:  18.8078670501709%

ADMET: Metabolism

CYP1A2-inhibitor:  0.98
CYP1A2-substrate:  0.938
CYP2C19-inhibitor:  0.858
CYP2C19-substrate:  0.29
CYP2C9-inhibitor:  0.593
CYP2C9-substrate:  0.852
CYP2D6-inhibitor:  0.116
CYP2D6-substrate:  0.854
CYP3A4-inhibitor:  0.13
CYP3A4-substrate:  0.272

ADMET: Excretion

Clearance (CL):  7.997
Half-life (T1/2):  0.512

ADMET: Toxicity

hERG Blockers:  0.025
Human Hepatotoxicity (H-HT):  0.285
Drug-inuced Liver Injury (DILI):  0.848
AMES Toxicity:  0.206
Rat Oral Acute Toxicity:  0.077
Maximum Recommended Daily Dose:  0.634
Skin Sensitization:  0.19
Carcinogencity:  0.497
Eye Corrosion:  0.042
Eye Irritation:  0.85
Respiratory Toxicity:  0.345

Download Data

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

  Natural Product: NPC29638

Natural Product ID:  NPC29638
Common Name*:   Methyleuparin
IUPAC Name:   1-(6-methoxy-2-prop-1-en-2-yl-1-benzofuran-5-yl)ethanone
Synonyms:   6-Methoxyeuparin
Standard InCHIKey:  XFSSPJGVPRWHLS-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H14O3/c1-8(2)12-6-10-5-11(9(3)15)14(16-4)7-13(10)17-12/h5-7H,1H2,2-4H3
SMILES:  COc1cc2oc(cc2cc1C(=O)C)C(=C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL451121
PubChem CID:   182181
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000301] Benzofurans

*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
NPO19965 Helenium alternifolium Species Asteraceae Eukaryota n.a. aerial part n.a. DOI[10.1021/jo01271a036]
NPO21850 Paeonia delavayi Species Paeoniaceae Eukaryota n.a. root n.a. PMID[10945272]
NPO23006 Moringa stenopetala Species Moringaceae Eukaryota n.a. n.a. n.a. PMID[12709911]
NPO22820 Sarcophyton glaucum Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[15332846]
NPO22820 Sarcophyton glaucum Species Alcyoniidae Eukaryota n.a. Amami Oshima, Kagoshima Prefecture, Japan n.a. PMID[16933862]
NPO22820 Sarcophyton glaucum Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[19331379]
NPO22820 Sarcophyton glaucum Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[21563811]
NPO20835 Medicago truncatula Species Fabaceae Eukaryota n.a. root n.a. PMID[21615146]
NPO21278 Lysimachia clethroides Species Primulaceae Eukaryota n.a. aerial part n.a. PMID[21928797]
NPO21850 Paeonia delavayi Species Paeoniaceae Eukaryota n.a. seed n.a. PMID[23497864]
NPO22372 Callicarpa bodinieri Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[29578342]
NPO14240 Justicia ghiesbreghtiana Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[9748395]
NPO12807 Citrus aurantiifolia Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO12807 Citrus aurantiifolia Species Rutaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO12807 Citrus aurantiifolia Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO12807 Citrus aurantiifolia Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO21221 Trapa bispinosa Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21850 Paeonia delavayi Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21343 Eupatorium fortunei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12807 Citrus aurantiifolia Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO12807 Citrus aurantiifolia Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO21413 Armillaria tabescens Species Physalacriaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21278 Lysimachia clethroides Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12807 Citrus aurantiifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21221 Trapa bispinosa Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15763 Huperzia lucidula Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21850 Paeonia delavayi Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21343 Eupatorium fortunei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15478 Senna sophera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22438 Asclepias speciosa Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21343 Eupatorium fortunei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21221 Trapa bispinosa Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22113 Anthocercis genistoides Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19965 Helenium alternifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20771 Thalictrum fortunei Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14240 Justicia ghiesbreghtiana Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21221 Trapa bispinosa Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22953 Eupatorium pauciflorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22756 Epimedium versicolor Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12807 Citrus aurantiifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21158 Viburnum fur Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21032 Manilkara hexandra Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22438 Asclepias speciosa Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22698 Achillea pannonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27929 Aphanamixis polystachya Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8115 Polyopes affinis Species Halymeniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21850 Paeonia delavayi Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13409 Crocus asturicus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22308 Stevia satureiaefolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20896 Mimosa tenuiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22372 Callicarpa bodinieri Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7123 Aria intermedia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20522 Pyura sacciformis Species Pyuridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20203 Syringa komarowi Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21654 Cyerce cristallina Species Caliphyllidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15763 Huperzia lucidula Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27489 Alloascoidea hylecoeti Species Alloascoideaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15478 Senna sophera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20261 Teucrium trifidum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22887 Scutellaria violacea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21725 Uncaria glabrata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20707 Stillingia sanguinolenta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4478 Parmelia pseudoreticulata Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20583 Phaulopsis imbricata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21343 Eupatorium fortunei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20457 Spirastrella inconstans Species Spirastrellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20088 Piper sintenense Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26325 Annulusmagnus triseptatus Species Annulatascaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19891 Diospyros crassiflora Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21278 Lysimachia clethroides Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22499 Corydalis flabellata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21413 Armillaria tabescens Species Physalacriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20021 Physcia aegialita Species Physciaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21089 Mourera fluviatilis Species Podostemaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28103 Erica carnea Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20967 Doriopsilla albopunctata Species Dendrodorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22820 Sarcophyton glaucum Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20381 Echites hirsuta Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21599 Ricciocarpos natans Species Ricciaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22048 Pteris palmiformis Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20835 Medicago truncatula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23006 Moringa stenopetala Species Moringaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18123 Dichapetalum madagascariense Species Dichapetalaceae 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
NPT1175 Organism Spodoptera litura Spodoptera litura pED50 = 7.21 n.a. PMID[517869]
NPT35 Others n.a. Rf = 0.66 n.a. PMID[517869]
NPT1175 Organism Spodoptera litura Spodoptera litura ED50 = 6.1 10'-8mol/cm2 PMID[517869]

☑ 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 NPC29638 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
0.9556 High Similarity NPC28337
0.9353 High Similarity NPC190572
0.9338 High Similarity NPC262635
0.9323 High Similarity NPC247743
0.9286 High Similarity NPC198427
0.9209 High Similarity NPC17262
0.9203 High Similarity NPC254010
0.9137 High Similarity NPC313036
0.9091 High Similarity NPC472406
0.9091 High Similarity NPC135303
0.9091 High Similarity NPC148423
0.9085 High Similarity NPC306788
0.9078 High Similarity NPC51641
0.9078 High Similarity NPC300267
0.9071 High Similarity NPC225884
0.9014 High Similarity NPC130581
0.9014 High Similarity NPC12148
0.9 High Similarity NPC53192
0.9 High Similarity NPC166858
0.9 High Similarity NPC51146
0.8966 High Similarity NPC130015
0.8966 High Similarity NPC38361
0.8966 High Similarity NPC263676
0.8963 High Similarity NPC229646
0.8951 High Similarity NPC135325
0.8951 High Similarity NPC266743
0.8944 High Similarity NPC210826
0.8936 High Similarity NPC302181
0.8921 High Similarity NPC37206
0.8921 High Similarity NPC137009
0.8904 High Similarity NPC41719
0.8897 High Similarity NPC116604
0.8897 High Similarity NPC472407
0.8897 High Similarity NPC292998
0.8889 High Similarity NPC226644
0.8889 High Similarity NPC88445
0.8889 High Similarity NPC39929
0.8889 High Similarity NPC296030
0.8889 High Similarity NPC37226
0.8881 High Similarity NPC74539
0.8881 High Similarity NPC304443
0.8873 High Similarity NPC246903
0.8873 High Similarity NPC230943
0.8857 High Similarity NPC470856
0.8844 High Similarity NPC233776
0.8836 High Similarity NPC253872
0.8828 High Similarity NPC191104
0.8819 High Similarity NPC272194
0.8797 High Similarity NPC475496
0.8797 High Similarity NPC49852
0.8794 High Similarity NPC171870
0.8767 High Similarity NPC170169
0.8767 High Similarity NPC98028
0.8759 High Similarity NPC221868
0.8759 High Similarity NPC178202
0.8759 High Similarity NPC37208
0.875 High Similarity NPC17816
0.875 High Similarity NPC284424
0.8731 High Similarity NPC473907
0.8731 High Similarity NPC50583
0.8714 High Similarity NPC36414
0.8707 High Similarity NPC5871
0.8705 High Similarity NPC161196
0.8705 High Similarity NPC254741
0.8705 High Similarity NPC268081
0.8699 High Similarity NPC78335
0.8699 High Similarity NPC230713
0.8696 High Similarity NPC125920
0.8667 High Similarity NPC473894
0.8662 High Similarity NPC22467
0.8652 High Similarity NPC11566
0.8649 High Similarity NPC213608
0.8649 High Similarity NPC122365
0.8649 High Similarity NPC131725
0.8649 High Similarity NPC1477
0.8649 High Similarity NPC473194
0.8649 High Similarity NPC183874
0.8647 High Similarity NPC65041
0.8643 High Similarity NPC157855
0.8643 High Similarity NPC253616
0.8643 High Similarity NPC259685
0.8633 High Similarity NPC46869
0.8633 High Similarity NPC60667
0.8633 High Similarity NPC151113
0.8623 High Similarity NPC93756
0.8623 High Similarity NPC108113
0.8613 High Similarity NPC278556
0.8611 High Similarity NPC98926
0.8611 High Similarity NPC155144
0.8611 High Similarity NPC208584
0.8592 High Similarity NPC16455
0.8592 High Similarity NPC307990
0.8592 High Similarity NPC472409
0.8591 High Similarity NPC148938
0.8591 High Similarity NPC198490
0.8582 High Similarity NPC237868
0.8582 High Similarity NPC131130
0.8582 High Similarity NPC17848
0.8571 High Similarity NPC156910
0.8571 High Similarity NPC472516
0.8571 High Similarity NPC174999
0.8571 High Similarity NPC222633
0.8562 High Similarity NPC168085
0.8561 High Similarity NPC125269
0.8553 High Similarity NPC264293
0.8551 High Similarity NPC101294
0.8551 High Similarity NPC473655
0.8551 High Similarity NPC182428
0.8542 High Similarity NPC189650
0.8542 High Similarity NPC106985
0.8542 High Similarity NPC18585
0.8542 High Similarity NPC166138
0.8533 High Similarity NPC160015
0.8533 High Similarity NPC180924
0.8533 High Similarity NPC247677
0.8531 High Similarity NPC3188
0.8531 High Similarity NPC110969
0.8531 High Similarity NPC103362
0.8529 High Similarity NPC230818
0.8529 High Similarity NPC211120
0.8523 High Similarity NPC235333
0.8523 High Similarity NPC472462
0.8521 High Similarity NPC18260
0.8521 High Similarity NPC136095
0.8521 High Similarity NPC78913
0.8521 High Similarity NPC472515
0.8514 High Similarity NPC106372
0.8514 High Similarity NPC156244
0.8514 High Similarity NPC58668
0.8514 High Similarity NPC115324
0.8511 High Similarity NPC103001
0.8511 High Similarity NPC228661
0.8503 High Similarity NPC317492
0.85 High Similarity NPC163029
0.85 High Similarity NPC99854
0.8497 Intermediate Similarity NPC193998
0.8497 Intermediate Similarity NPC219861
0.8496 Intermediate Similarity NPC141252
0.8496 Intermediate Similarity NPC11799
0.8493 Intermediate Similarity NPC471285
0.8489 Intermediate Similarity NPC223354
0.8483 Intermediate Similarity NPC297788
0.8483 Intermediate Similarity NPC234629
0.8483 Intermediate Similarity NPC470857
0.8483 Intermediate Similarity NPC179970
0.8483 Intermediate Similarity NPC311741
0.8478 Intermediate Similarity NPC473584
0.8478 Intermediate Similarity NPC475589
0.8478 Intermediate Similarity NPC313618
0.8478 Intermediate Similarity NPC27490
0.8478 Intermediate Similarity NPC31872
0.8478 Intermediate Similarity NPC470859
0.8477 Intermediate Similarity NPC164110
0.8477 Intermediate Similarity NPC269495
0.8477 Intermediate Similarity NPC246647
0.8477 Intermediate Similarity NPC212967
0.8477 Intermediate Similarity NPC96342
0.8477 Intermediate Similarity NPC296957
0.8477 Intermediate Similarity NPC260902
0.8477 Intermediate Similarity NPC65504
0.8472 Intermediate Similarity NPC144499
0.8472 Intermediate Similarity NPC11561
0.8472 Intermediate Similarity NPC147145
0.8472 Intermediate Similarity NPC226636
0.8467 Intermediate Similarity NPC297531
0.8467 Intermediate Similarity NPC213936
0.8467 Intermediate Similarity NPC295608
0.8467 Intermediate Similarity NPC473193
0.8467 Intermediate Similarity NPC250769
0.8467 Intermediate Similarity NPC84772
0.8467 Intermediate Similarity NPC278010
0.8462 Intermediate Similarity NPC305355
0.8462 Intermediate Similarity NPC150522
0.8462 Intermediate Similarity NPC69769
0.8462 Intermediate Similarity NPC172986
0.8462 Intermediate Similarity NPC241100
0.8462 Intermediate Similarity NPC171094
0.8462 Intermediate Similarity NPC475680
0.8462 Intermediate Similarity NPC270883
0.8462 Intermediate Similarity NPC159275
0.8462 Intermediate Similarity NPC261227
0.8456 Intermediate Similarity NPC80694
0.8456 Intermediate Similarity NPC125887
0.8456 Intermediate Similarity NPC207624
0.8456 Intermediate Similarity NPC186098
0.8456 Intermediate Similarity NPC67654
0.8451 Intermediate Similarity NPC474504
0.8451 Intermediate Similarity NPC21350
0.8451 Intermediate Similarity NPC470672
0.8451 Intermediate Similarity NPC474487
0.8451 Intermediate Similarity NPC201395
0.8451 Intermediate Similarity NPC124269
0.8451 Intermediate Similarity NPC470671
0.8446 Intermediate Similarity NPC167576
0.8446 Intermediate Similarity NPC155882
0.8446 Intermediate Similarity NPC472421
0.8442 Intermediate Similarity NPC65846
0.8442 Intermediate Similarity NPC109180
0.8442 Intermediate Similarity NPC472581
0.844 Intermediate Similarity NPC12165

  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 NPC29638 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
0.9338 High Similarity NPD1243 Approved
0.9 High Similarity NPD643 Clinical (unspecified phase)
0.8881 High Similarity NPD920 Approved
0.8873 High Similarity NPD642 Clinical (unspecified phase)
0.8705 High Similarity NPD2796 Approved
0.8553 High Similarity NPD1247 Approved
0.8478 Intermediate Similarity NPD1240 Approved
0.8421 Intermediate Similarity NPD919 Approved
0.8357 Intermediate Similarity NPD1607 Approved
0.8356 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8322 Intermediate Similarity NPD1549 Phase 2
0.8267 Intermediate Similarity NPD7411 Suspended
0.8252 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8252 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8239 Intermediate Similarity NPD1510 Phase 2
0.8138 Intermediate Similarity NPD2800 Approved
0.8125 Intermediate Similarity NPD2344 Approved
0.8108 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8105 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8041 Intermediate Similarity NPD6799 Approved
0.8039 Intermediate Similarity NPD7819 Suspended
0.8039 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD5494 Approved
0.8 Intermediate Similarity NPD1471 Phase 3
0.8 Intermediate Similarity NPD3749 Approved
0.7975 Intermediate Similarity NPD3926 Phase 2
0.7925 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7922 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7905 Intermediate Similarity NPD2309 Approved
0.7891 Intermediate Similarity NPD2654 Approved
0.7891 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD7075 Discontinued
0.7862 Intermediate Similarity NPD3748 Approved
0.7857 Intermediate Similarity NPD6801 Discontinued
0.7843 Intermediate Similarity NPD4380 Phase 2
0.7843 Intermediate Similarity NPD6599 Discontinued
0.7823 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD3882 Suspended
0.781 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.78 Intermediate Similarity NPD1511 Approved
0.7748 Intermediate Similarity NPD2533 Approved
0.7748 Intermediate Similarity NPD2532 Approved
0.7748 Intermediate Similarity NPD2534 Approved
0.7742 Intermediate Similarity NPD1934 Approved
0.7716 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7707 Intermediate Similarity NPD7768 Phase 2
0.7697 Intermediate Similarity NPD1512 Approved
0.7687 Intermediate Similarity NPD1551 Phase 2
0.7636 Intermediate Similarity NPD6559 Discontinued
0.7625 Intermediate Similarity NPD6959 Discontinued
0.7619 Intermediate Similarity NPD2799 Discontinued
0.7603 Intermediate Similarity NPD6651 Approved
0.76 Intermediate Similarity NPD3750 Approved
0.758 Intermediate Similarity NPD2801 Approved
0.7569 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7552 Intermediate Similarity NPD6832 Phase 2
0.7547 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7537 Intermediate Similarity NPD1241 Discontinued
0.7532 Intermediate Similarity NPD3817 Phase 2
0.7517 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD6279 Approved
0.7516 Intermediate Similarity NPD6280 Approved
0.7515 Intermediate Similarity NPD1729 Discontinued
0.75 Intermediate Similarity NPD9717 Approved
0.7485 Intermediate Similarity NPD2403 Approved
0.7469 Intermediate Similarity NPD6808 Phase 2
0.745 Intermediate Similarity NPD2935 Discontinued
0.7448 Intermediate Similarity NPD2313 Discontinued
0.7436 Intermediate Similarity NPD3226 Approved
0.7419 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD1019 Discontinued
0.7403 Intermediate Similarity NPD5401 Approved
0.7394 Intermediate Similarity NPD3818 Discontinued
0.7383 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD3972 Approved
0.7368 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD5953 Discontinued
0.7349 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD1203 Approved
0.7343 Intermediate Similarity NPD3267 Approved
0.7343 Intermediate Similarity NPD3266 Approved
0.7329 Intermediate Similarity NPD1296 Phase 2
0.7312 Intermediate Similarity NPD2296 Approved
0.7308 Intermediate Similarity NPD5403 Approved
0.7297 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD2798 Approved
0.7286 Intermediate Similarity NPD17 Approved
0.7273 Intermediate Similarity NPD1876 Approved
0.7273 Intermediate Similarity NPD6166 Phase 2
0.7273 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD6232 Discontinued
0.7246 Intermediate Similarity NPD7286 Phase 2
0.723 Intermediate Similarity NPD943 Approved
0.7229 Intermediate Similarity NPD7473 Discontinued
0.7183 Intermediate Similarity NPD422 Phase 1
0.7181 Intermediate Similarity NPD1933 Approved
0.7171 Intermediate Similarity NPD2346 Discontinued
0.716 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD9545 Approved
0.7143 Intermediate Similarity NPD5844 Phase 1
0.7143 Intermediate Similarity NPD4628 Phase 3
0.7133 Intermediate Similarity NPD1608 Approved
0.7125 Intermediate Similarity NPD5890 Approved
0.7125 Intermediate Similarity NPD5889 Approved
0.7122 Intermediate Similarity NPD9493 Approved
0.7114 Intermediate Similarity NPD4307 Phase 2
0.7105 Intermediate Similarity NPD6100 Approved
0.7105 Intermediate Similarity NPD6099 Approved
0.7101 Intermediate Similarity NPD7074 Phase 3
0.7099 Intermediate Similarity NPD5402 Approved
0.7095 Intermediate Similarity NPD3268 Approved
0.7095 Intermediate Similarity NPD411 Approved
0.7092 Intermediate Similarity NPD1651 Approved
0.7067 Intermediate Similarity NPD230 Phase 1
0.7067 Intermediate Similarity NPD447 Suspended
0.7063 Intermediate Similarity NPD6585 Discontinued
0.7063 Intermediate Similarity NPD1610 Phase 2
0.7048 Intermediate Similarity NPD5710 Approved
0.7048 Intermediate Similarity NPD5711 Approved
0.7041 Intermediate Similarity NPD7054 Approved
0.7037 Intermediate Similarity NPD1465 Phase 2
0.7032 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD4287 Approved
0.7021 Intermediate Similarity NPD1548 Phase 1
0.7006 Intermediate Similarity NPD7390 Discontinued
0.7 Intermediate Similarity NPD3140 Approved
0.7 Intermediate Similarity NPD3142 Approved
0.7 Intermediate Similarity NPD7472 Approved
0.6986 Remote Similarity NPD1164 Approved
0.698 Remote Similarity NPD4907 Clinical (unspecified phase)
0.697 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6959 Remote Similarity NPD1008 Clinical (unspecified phase)
0.6959 Remote Similarity NPD6797 Phase 2
0.6946 Remote Similarity NPD7229 Phase 3
0.6944 Remote Similarity NPD1281 Approved
0.6928 Remote Similarity NPD4308 Phase 3
0.6928 Remote Similarity NPD7033 Discontinued
0.6927 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6927 Remote Similarity NPD4361 Phase 2
0.6919 Remote Similarity NPD7251 Discontinued
0.6919 Remote Similarity NPD3658 Clinical (unspecified phase)
0.689 Remote Similarity NPD4288 Approved
0.6882 Remote Similarity NPD2163 Approved
0.6879 Remote Similarity NPD7808 Phase 3
0.6871 Remote Similarity NPD2797 Approved
0.6848 Remote Similarity NPD4947 Clinical (unspecified phase)
0.6846 Remote Similarity NPD4908 Phase 1
0.6839 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6839 Remote Similarity NPD2353 Approved
0.6821 Remote Similarity NPD6104 Discontinued
0.6818 Remote Similarity NPD8434 Phase 2
0.6818 Remote Similarity NPD651 Clinical (unspecified phase)
0.6815 Remote Similarity NPD7003 Approved
0.6803 Remote Similarity NPD3225 Approved
0.6803 Remote Similarity NPD1283 Approved
0.68 Remote Similarity NPD4625 Phase 3
0.6791 Remote Similarity NPD9261 Approved
0.6788 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6782 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6778 Remote Similarity NPD4360 Phase 2
0.6778 Remote Similarity NPD4363 Phase 3
0.6776 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6772 Remote Similarity NPD3295 Clinical (unspecified phase)
0.6772 Remote Similarity NPD3887 Approved
0.677 Remote Similarity NPD3873 Phase 3
0.677 Remote Similarity NPD3869 Phase 3
0.6765 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6765 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6763 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6755 Remote Similarity NPD3764 Approved
0.6755 Remote Similarity NPD1699 Clinical (unspecified phase)
0.675 Remote Similarity NPD4661 Approved
0.675 Remote Similarity NPD4662 Approved
0.675 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6746 Remote Similarity NPD5668 Clinical (unspecified phase)
0.6736 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6736 Remote Similarity NPD5691 Approved
0.6732 Remote Similarity NPD5124 Phase 1
0.6732 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6731 Remote Similarity NPD6005 Phase 3
0.6731 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6731 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6731 Remote Similarity NPD6004 Phase 3
0.6731 Remote Similarity NPD6002 Phase 3
0.6727 Remote Similarity NPD5760 Phase 2
0.6727 Remote Similarity NPD5761 Phase 2
0.6712 Remote Similarity NPD1201 Approved
0.6707 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6703 Remote Similarity NPD8090 Clinical (unspecified phase)
0.669 Remote Similarity NPD1778 Approved
0.6688 Remote Similarity NPD2424 Discontinued
0.6687 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6687 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6687 Remote Similarity NPD7458 Discontinued
0.6686 Remote Similarity NPD7199 Phase 2
0.6667 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4476 Approved
0.6667 Remote Similarity NPD4477 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