Structure

Physi-Chem Properties

Molecular Weight:  238.19
Volume:  265.827
LogP:  2.571
LogD:  2.711
LogS:  -4.017
# Rotatable Bonds:  1
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.69
Synthetic Accessibility Score:  4.304
Fsp3:  0.867
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:  -4.556
MDCK Permeability:  1.3472107639245223e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.058
30% Bioavailability (F30%):  0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.397
Plasma Protein Binding (PPB):  76.85464477539062%
Volume Distribution (VD):  1.11
Pgp-substrate:  19.01932716369629%

ADMET: Metabolism

CYP1A2-inhibitor:  0.068
CYP1A2-substrate:  0.57
CYP2C19-inhibitor:  0.05
CYP2C19-substrate:  0.917
CYP2C9-inhibitor:  0.115
CYP2C9-substrate:  0.322
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.167
CYP3A4-inhibitor:  0.131
CYP3A4-substrate:  0.86

ADMET: Excretion

Clearance (CL):  6.414
Half-life (T1/2):  0.22

ADMET: Toxicity

hERG Blockers:  0.033
Human Hepatotoxicity (H-HT):  0.348
Drug-inuced Liver Injury (DILI):  0.034
AMES Toxicity:  0.013
Rat Oral Acute Toxicity:  0.035
Maximum Recommended Daily Dose:  0.091
Skin Sensitization:  0.427
Carcinogencity:  0.735
Eye Corrosion:  0.313
Eye Irritation:  0.838
Respiratory Toxicity:  0.911

Download Data

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

  Natural Product: NPC283316

Natural Product ID:  NPC283316
Common Name*:   4(15)-Eudesmene-1Beta,5Alpha-Diol
IUPAC Name:   (1R,4aR,6R,8aS)-8a-methyl-4-methylidene-6-propan-2-yl-2,3,5,6,7,8-hexahydro-1H-naphthalene-1,4a-diol
Synonyms:  
Standard InCHIKey:  CKGNGZNSTIOFOY-APIJFGDWSA-N
Standard InCHI:  InChI=1S/C15H26O2/c1-10(2)12-7-8-14(4)13(16)6-5-11(3)15(14,17)9-12/h10,12-13,16-17H,3,5-9H2,1-2,4H3/t12-,13-,14+,15-/m1/s1
SMILES:  CC([C@@H]1CC[C@@]2([C@](C1)(O)C(=C)CC[C@H]2O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL484426
PubChem CID:   636618
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

*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
NPO25111 Streptomyces tanashiensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. DOI[10.1016/S0040-4039(01)84249-0]
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]
NPO22051 Litsea verticillata Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[12762792]
NPO22820 Sarcophyton glaucum Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[15332846]
NPO4501 Caragana intermedia Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[15620236]
NPO24121 Vernoniopsis caudata n.a. n.a. n.a. n.a. n.a. n.a. PMID[15921436]
NPO20815 Lindera fruticosa Species Lauraceae Eukaryota roots n.a. n.a. PMID[16724860]
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]
NPO24560 Ricinus communis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[26509914]
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 n.a. n.a. Database[FooDB]
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]
NPO22051 Litsea verticillata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21343 Eupatorium fortunei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21850 Paeonia delavayi Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21787 Betula pubescens Species Betulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22722 Ranunculus japonicus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24560 Ricinus communis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20362 Ruta montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21221 Trapa bispinosa Species Lythraceae 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]
NPO24560 Ricinus communis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15763 Huperzia lucidula Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21787 Betula pubescens Species Betulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22051 Litsea verticillata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21850 Paeonia delavayi Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21413 Armillaria tabescens Species Physalacriaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22722 Ranunculus japonicus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12807 Citrus aurantiifolia Species Rutaceae 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]
NPO21278 Lysimachia clethroides Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20362 Ruta montana 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]
NPO21343 Eupatorium fortunei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20362 Ruta montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
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]
NPO24560 Ricinus communis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22051 Litsea verticillata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24560 Ricinus communis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21343 Eupatorium fortunei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21683 Selaginella lepidophylla Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20583 Phaulopsis imbricata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20362 Ruta montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26325 Annulusmagnus triseptatus Species Annulatascaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20261 Teucrium trifidum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20021 Physcia aegialita Species Physciaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21787 Betula pubescens Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18589 Allopora californica n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO20088 Piper sintenense Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23158 Penicillium carminoviolaceum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22051 Litsea verticillata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22820 Sarcophyton glaucum Species Alcyoniidae 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]
NPO16184 Asclepias asperula Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21089 Mourera fluviatilis Species Podostemaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20381 Echites hirsuta Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28103 Erica carnea Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18123 Dichapetalum madagascariense Species Dichapetalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24560 Ricinus communis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24776 Euryops jacksonii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21599 Ricciocarpos natans Species Ricciaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24121 Vernoniopsis caudata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO22048 Pteris palmiformis Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4478 Parmelia pseudoreticulata Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20771 Thalictrum fortunei Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21121 Ips japonicus Species Curculionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20835 Medicago truncatula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23376 Genista aetnensis 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]
NPO25111 Streptomyces tanashiensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO20457 Spirastrella inconstans Species Spirastrellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21221 Trapa bispinosa Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16971 Sparassis crispa Species Sparassidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19965 Helenium alternifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19891 Diospyros crassiflora Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23676 Fleroya rubrostipulata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23445 Vernonia triflosculosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22113 Anthocercis genistoides Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17668 Artemisia gmelinii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14240 Justicia ghiesbreghtiana Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21413 Armillaria tabescens Species Physalacriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12807 Citrus aurantiifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4501 Caragana intermedia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22756 Epimedium versicolor Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20967 Doriopsilla albopunctata Species Dendrodorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22438 Asclepias speciosa Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13388 Lithophyllum incrustans Species Corallinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22953 Eupatorium pauciflorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21032 Manilkara hexandra Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14448 Laurencia venusta Species Rhodomelaceae 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]
NPO21158 Viburnum fur Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24411 Pentaspadon motleyi Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20226 Artemisia filatovae Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8115 Polyopes affinis Species Halymeniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23843 Clerodendrum grayi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27929 Aphanamixis polystachya Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22713 Aquilegia flabellata Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23948 Serratia plymuthica Species Yersiniaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO22372 Callicarpa bodinieri Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22698 Achillea pannonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21654 Cyerce cristallina Species Caliphyllidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20896 Mimosa tenuiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20707 Stillingia sanguinolenta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20203 Syringa komarowi Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22308 Stevia satureiaefolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15478 Senna sophera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20815 Lindera fruticosa Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20936 Arecastrum romanzoffianum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO27489 Alloascoidea hylecoeti Species Alloascoideaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21725 Uncaria glabrata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20522 Pyura sacciformis Species Pyuridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22722 Ranunculus japonicus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22887 Scutellaria violacea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15763 Huperzia lucidula Species Lycopodiaceae 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
NPT2219 Cell Line C2C12 Mus musculus IC50 = 10.7 ug.mL-1 PMID[550354]
NPT826 Organism Magnaporthe oryzae Magnaporthe oryzae MIC = 20.0 ug.mL-1 PMID[550354]
NPT32 Organism Mus musculus Mus musculus MIC = 100.0 mg kg-1 PMID[550354]

☑ 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 NPC283316 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
0.9692 High Similarity NPC266578
0.9545 High Similarity NPC234511
0.9394 High Similarity NPC245795
0.9242 High Similarity NPC269077
0.9242 High Similarity NPC253303
0.9231 High Similarity NPC258595
0.9104 High Similarity NPC276616
0.9077 High Similarity NPC101128
0.8788 High Similarity NPC68656
0.875 High Similarity NPC63958
0.8676 High Similarity NPC139207
0.8676 High Similarity NPC185874
0.8657 High Similarity NPC11555
0.8657 High Similarity NPC60837
0.8657 High Similarity NPC2728
0.8657 High Similarity NPC172613
0.8657 High Similarity NPC282619
0.8657 High Similarity NPC208198
0.8611 High Similarity NPC32832
0.8592 High Similarity NPC95165
0.8551 High Similarity NPC244790
0.8529 High Similarity NPC475897
0.8514 High Similarity NPC31828
0.8507 High Similarity NPC144650
0.8429 Intermediate Similarity NPC9942
0.8421 Intermediate Similarity NPC249423
0.84 Intermediate Similarity NPC476316
0.8308 Intermediate Similarity NPC474769
0.8308 Intermediate Similarity NPC189290
0.8267 Intermediate Similarity NPC472499
0.8267 Intermediate Similarity NPC472502
0.8267 Intermediate Similarity NPC472500
0.8267 Intermediate Similarity NPC472501
0.8267 Intermediate Similarity NPC475
0.8261 Intermediate Similarity NPC473929
0.8261 Intermediate Similarity NPC476406
0.8219 Intermediate Similarity NPC306727
0.8219 Intermediate Similarity NPC201048
0.8219 Intermediate Similarity NPC308440
0.8219 Intermediate Similarity NPC472503
0.8219 Intermediate Similarity NPC476366
0.8194 Intermediate Similarity NPC167706
0.8158 Intermediate Similarity NPC116119
0.8158 Intermediate Similarity NPC24504
0.8158 Intermediate Similarity NPC475727
0.8158 Intermediate Similarity NPC80297
0.8158 Intermediate Similarity NPC472742
0.8143 Intermediate Similarity NPC101307
0.8143 Intermediate Similarity NPC88454
0.8143 Intermediate Similarity NPC117607
0.8133 Intermediate Similarity NPC260301
0.8133 Intermediate Similarity NPC307336
0.8133 Intermediate Similarity NPC470711
0.8133 Intermediate Similarity NPC31037
0.8133 Intermediate Similarity NPC470758
0.8116 Intermediate Similarity NPC300442
0.8108 Intermediate Similarity NPC144075
0.8108 Intermediate Similarity NPC185536
0.8101 Intermediate Similarity NPC256567
0.8082 Intermediate Similarity NPC220939
0.8082 Intermediate Similarity NPC265485
0.8052 Intermediate Similarity NPC47149
0.8052 Intermediate Similarity NPC475679
0.8026 Intermediate Similarity NPC52755
0.8026 Intermediate Similarity NPC472342
0.8026 Intermediate Similarity NPC301707
0.8 Intermediate Similarity NPC253190
0.8 Intermediate Similarity NPC470360
0.8 Intermediate Similarity NPC265588
0.8 Intermediate Similarity NPC470749
0.8 Intermediate Similarity NPC264779
0.7975 Intermediate Similarity NPC232023
0.7975 Intermediate Similarity NPC216420
0.7975 Intermediate Similarity NPC470929
0.7975 Intermediate Similarity NPC85095
0.7975 Intermediate Similarity NPC211135
0.7975 Intermediate Similarity NPC477978
0.7973 Intermediate Similarity NPC476736
0.7971 Intermediate Similarity NPC219940
0.7949 Intermediate Similarity NPC242350
0.7949 Intermediate Similarity NPC476646
0.7945 Intermediate Similarity NPC23954
0.7945 Intermediate Similarity NPC164022
0.7922 Intermediate Similarity NPC5604
0.7917 Intermediate Similarity NPC210323
0.7901 Intermediate Similarity NPC299068
0.7901 Intermediate Similarity NPC6391
0.7895 Intermediate Similarity NPC212241
0.7895 Intermediate Similarity NPC248830
0.7895 Intermediate Similarity NPC138502
0.7895 Intermediate Similarity NPC202540
0.7895 Intermediate Similarity NPC257191
0.7895 Intermediate Similarity NPC91594
0.7895 Intermediate Similarity NPC331618
0.7895 Intermediate Similarity NPC130136
0.7895 Intermediate Similarity NPC471798
0.7895 Intermediate Similarity NPC119355
0.7875 Intermediate Similarity NPC86238
0.7867 Intermediate Similarity NPC133580
0.7867 Intermediate Similarity NPC3403
0.7857 Intermediate Similarity NPC86856
0.7848 Intermediate Similarity NPC155521
0.7838 Intermediate Similarity NPC211009
0.7838 Intermediate Similarity NPC472506
0.7831 Intermediate Similarity NPC470361
0.7821 Intermediate Similarity NPC324772
0.7821 Intermediate Similarity NPC471266
0.7821 Intermediate Similarity NPC95124
0.7821 Intermediate Similarity NPC96362
0.7808 Intermediate Similarity NPC45296
0.7808 Intermediate Similarity NPC34834
0.7808 Intermediate Similarity NPC92801
0.7792 Intermediate Similarity NPC477819
0.7792 Intermediate Similarity NPC477817
0.7778 Intermediate Similarity NPC96484
0.7778 Intermediate Similarity NPC2648
0.7778 Intermediate Similarity NPC164424
0.7763 Intermediate Similarity NPC91573
0.7763 Intermediate Similarity NPC78067
0.7763 Intermediate Similarity NPC38141
0.7763 Intermediate Similarity NPC93662
0.7763 Intermediate Similarity NPC278091
0.775 Intermediate Similarity NPC113978
0.7738 Intermediate Similarity NPC3345
0.7738 Intermediate Similarity NPC329596
0.7738 Intermediate Similarity NPC204188
0.7738 Intermediate Similarity NPC80561
0.7738 Intermediate Similarity NPC291484
0.7738 Intermediate Similarity NPC11216
0.7733 Intermediate Similarity NPC91858
0.7722 Intermediate Similarity NPC320525
0.7722 Intermediate Similarity NPC157655
0.7722 Intermediate Similarity NPC470383
0.7722 Intermediate Similarity NPC471270
0.7714 Intermediate Similarity NPC96793
0.7714 Intermediate Similarity NPC323424
0.7703 Intermediate Similarity NPC301226
0.7703 Intermediate Similarity NPC471272
0.7703 Intermediate Similarity NPC477792
0.7703 Intermediate Similarity NPC111234
0.7703 Intermediate Similarity NPC164045
0.7692 Intermediate Similarity NPC72755
0.7692 Intermediate Similarity NPC476367
0.7692 Intermediate Similarity NPC472463
0.7683 Intermediate Similarity NPC121981
0.7683 Intermediate Similarity NPC201273
0.7683 Intermediate Similarity NPC261266
0.7681 Intermediate Similarity NPC41160
0.7671 Intermediate Similarity NPC474248
0.7662 Intermediate Similarity NPC169994
0.7654 Intermediate Similarity NPC83702
0.7647 Intermediate Similarity NPC97404
0.7647 Intermediate Similarity NPC41554
0.7639 Intermediate Similarity NPC74885
0.7639 Intermediate Similarity NPC68703
0.7639 Intermediate Similarity NPC308522
0.7639 Intermediate Similarity NPC69649
0.7632 Intermediate Similarity NPC230704
0.7632 Intermediate Similarity NPC231256
0.7632 Intermediate Similarity NPC212879
0.7632 Intermediate Similarity NPC103822
0.7632 Intermediate Similarity NPC104387
0.7632 Intermediate Similarity NPC240235
0.7632 Intermediate Similarity NPC70982
0.7632 Intermediate Similarity NPC178383
0.7625 Intermediate Similarity NPC296701
0.7625 Intermediate Similarity NPC218616
0.7619 Intermediate Similarity NPC101886
0.7619 Intermediate Similarity NPC194642
0.7619 Intermediate Similarity NPC187785
0.7619 Intermediate Similarity NPC259875
0.7606 Intermediate Similarity NPC64123
0.76 Intermediate Similarity NPC182717
0.7595 Intermediate Similarity NPC236707
0.7595 Intermediate Similarity NPC71535
0.7595 Intermediate Similarity NPC295131
0.7595 Intermediate Similarity NPC78545
0.759 Intermediate Similarity NPC476948
0.759 Intermediate Similarity NPC477600
0.7576 Intermediate Similarity NPC67508
0.7576 Intermediate Similarity NPC84824
0.7564 Intermediate Similarity NPC158662
0.7564 Intermediate Similarity NPC196753
0.7564 Intermediate Similarity NPC11908
0.7564 Intermediate Similarity NPC148977
0.7564 Intermediate Similarity NPC230295
0.7564 Intermediate Similarity NPC253807
0.7564 Intermediate Similarity NPC98386
0.7564 Intermediate Similarity NPC42853
0.7564 Intermediate Similarity NPC285761
0.7558 Intermediate Similarity NPC119379
0.7538 Intermediate Similarity NPC36002
0.7538 Intermediate Similarity NPC102336
0.7534 Intermediate Similarity NPC474756
0.7534 Intermediate Similarity NPC471238
0.7532 Intermediate Similarity NPC14112
0.7532 Intermediate Similarity NPC470766
0.7532 Intermediate Similarity NPC86305
0.7531 Intermediate Similarity NPC185605
0.7531 Intermediate Similarity NPC320548

  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 NPC283316 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
0.7821 Intermediate Similarity NPD6931 Approved
0.7821 Intermediate Similarity NPD6930 Phase 2
0.7692 Intermediate Similarity NPD6929 Approved
0.7531 Intermediate Similarity NPD6695 Phase 3
0.7468 Intermediate Similarity NPD7645 Phase 2
0.7439 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD6925 Approved
0.7436 Intermediate Similarity NPD5776 Phase 2
0.7375 Intermediate Similarity NPD7514 Phase 3
0.7375 Intermediate Similarity NPD7525 Registered
0.7375 Intermediate Similarity NPD7332 Phase 2
0.7349 Intermediate Similarity NPD6893 Approved
0.7342 Intermediate Similarity NPD7145 Approved
0.7284 Intermediate Similarity NPD6898 Phase 1
0.7215 Intermediate Similarity NPD6932 Approved
0.7176 Intermediate Similarity NPD7524 Approved
0.7176 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD7750 Discontinued
0.7089 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD6902 Approved
0.7051 Intermediate Similarity NPD6924 Approved
0.7051 Intermediate Similarity NPD6926 Approved
0.7037 Intermediate Similarity NPD6683 Phase 2
0.6962 Remote Similarity NPD6942 Approved
0.6962 Remote Similarity NPD7339 Approved
0.6944 Remote Similarity NPD368 Approved
0.6875 Remote Similarity NPD6933 Approved
0.6854 Remote Similarity NPD7087 Discontinued
0.6757 Remote Similarity NPD371 Approved
0.6753 Remote Similarity NPD4267 Clinical (unspecified phase)
0.675 Remote Similarity NPD8264 Approved
0.6747 Remote Similarity NPD7509 Discontinued
0.6744 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6707 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3618 Phase 1
0.6615 Remote Similarity NPD385 Approved
0.6615 Remote Similarity NPD384 Approved
0.6588 Remote Similarity NPD3667 Approved
0.6582 Remote Similarity NPD4243 Approved
0.6548 Remote Similarity NPD4748 Discontinued
0.6538 Remote Similarity NPD6923 Approved
0.6538 Remote Similarity NPD6922 Approved
0.6526 Remote Similarity NPD7640 Approved
0.6526 Remote Similarity NPD7639 Approved
0.6512 Remote Similarity NPD4788 Approved
0.65 Remote Similarity NPD4732 Discontinued
0.6456 Remote Similarity NPD7143 Approved
0.6456 Remote Similarity NPD7144 Approved
0.6444 Remote Similarity NPD5328 Approved
0.6437 Remote Similarity NPD3133 Approved
0.6437 Remote Similarity NPD4786 Approved
0.6437 Remote Similarity NPD3665 Phase 1
0.6437 Remote Similarity NPD3666 Approved
0.6421 Remote Similarity NPD7638 Approved
0.642 Remote Similarity NPD4784 Approved
0.642 Remote Similarity NPD4785 Approved
0.6413 Remote Similarity NPD4202 Approved
0.6392 Remote Similarity NPD5211 Phase 2
0.6375 Remote Similarity NPD7150 Approved
0.6375 Remote Similarity NPD7152 Approved
0.6375 Remote Similarity NPD7151 Approved
0.6374 Remote Similarity NPD7136 Phase 2
0.6341 Remote Similarity NPD4190 Phase 3
0.6341 Remote Similarity NPD3703 Phase 2
0.6341 Remote Similarity NPD5275 Approved
0.6338 Remote Similarity NPD342 Phase 1
0.6316 Remote Similarity NPD4755 Approved
0.6304 Remote Similarity NPD7515 Phase 2
0.6304 Remote Similarity NPD7637 Suspended
0.6304 Remote Similarity NPD6079 Approved
0.6264 Remote Similarity NPD4753 Phase 2
0.6263 Remote Similarity NPD5141 Approved
0.625 Remote Similarity NPD4225 Approved
0.625 Remote Similarity NPD4787 Phase 1
0.6235 Remote Similarity NPD4195 Approved
0.6212 Remote Similarity NPD386 Approved
0.6212 Remote Similarity NPD388 Approved
0.6186 Remote Similarity NPD5285 Approved
0.6186 Remote Similarity NPD5286 Approved
0.6186 Remote Similarity NPD4700 Approved
0.6186 Remote Similarity NPD4696 Approved
0.6129 Remote Similarity NPD8035 Phase 2
0.6129 Remote Similarity NPD8034 Phase 2
0.6125 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6125 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6122 Remote Similarity NPD4159 Approved
0.6118 Remote Similarity NPD6114 Approved
0.6118 Remote Similarity NPD6697 Approved
0.6118 Remote Similarity NPD6115 Approved
0.6118 Remote Similarity NPD6118 Approved
0.6111 Remote Similarity NPD4623 Approved
0.6111 Remote Similarity NPD4519 Discontinued
0.6078 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6061 Remote Similarity NPD4633 Approved
0.6061 Remote Similarity NPD5224 Approved
0.6061 Remote Similarity NPD5225 Approved
0.6061 Remote Similarity NPD7632 Discontinued
0.6061 Remote Similarity NPD5226 Approved
0.6042 Remote Similarity NPD5221 Approved
0.6042 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6042 Remote Similarity NPD4697 Phase 3
0.6042 Remote Similarity NPD5222 Approved
0.6026 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6023 Remote Similarity NPD4221 Approved
0.6023 Remote Similarity NPD4223 Phase 3
0.6019 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6 Remote Similarity NPD5175 Approved
0.6 Remote Similarity NPD5174 Approved
0.6 Remote Similarity NPD7748 Approved
0.5979 Remote Similarity NPD5173 Approved
0.5976 Remote Similarity NPD4809 Clinical (unspecified phase)
0.5976 Remote Similarity NPD4808 Clinical (unspecified phase)
0.5962 Remote Similarity NPD4634 Approved
0.596 Remote Similarity NPD5223 Approved
0.596 Remote Similarity NPD5344 Discontinued
0.5938 Remote Similarity NPD4629 Approved
0.5938 Remote Similarity NPD5210 Approved
0.5934 Remote Similarity NPD5279 Phase 3
0.5934 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5926 Remote Similarity NPD3698 Phase 2
0.5921 Remote Similarity NPD1145 Discontinued
0.5918 Remote Similarity NPD5290 Discontinued
0.5895 Remote Similarity NPD5779 Approved
0.5895 Remote Similarity NPD5778 Approved
0.5889 Remote Similarity NPD4197 Approved
0.5889 Remote Similarity NPD3668 Phase 3
0.5882 Remote Similarity NPD6117 Approved
0.5882 Remote Similarity NPD6675 Approved
0.5882 Remote Similarity NPD4768 Approved
0.5882 Remote Similarity NPD7128 Approved
0.5882 Remote Similarity NPD4767 Approved
0.5882 Remote Similarity NPD5739 Approved
0.5882 Remote Similarity NPD6402 Approved
0.5872 Remote Similarity NPD7327 Approved
0.5872 Remote Similarity NPD7328 Approved
0.5854 Remote Similarity NPD4245 Approved
0.5854 Remote Similarity NPD4244 Approved
0.5851 Remote Similarity NPD3168 Discontinued
0.5842 Remote Similarity NPD4754 Approved
0.5833 Remote Similarity NPD1811 Approved
0.5833 Remote Similarity NPD6113 Clinical (unspecified phase)
0.5833 Remote Similarity NPD1810 Approved
0.5825 Remote Similarity NPD5697 Approved
0.5825 Remote Similarity NPD5701 Approved
0.5824 Remote Similarity NPD5329 Approved
0.5824 Remote Similarity NPD1696 Phase 3
0.5818 Remote Similarity NPD7516 Approved
0.5816 Remote Similarity NPD6084 Phase 2
0.5816 Remote Similarity NPD7902 Approved
0.5816 Remote Similarity NPD6083 Phase 2
0.5814 Remote Similarity NPD6116 Phase 1
0.581 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5795 Remote Similarity NPD4695 Discontinued
0.5795 Remote Similarity NPD6928 Phase 2
0.5794 Remote Similarity NPD8133 Approved
0.5769 Remote Similarity NPD6881 Approved
0.5769 Remote Similarity NPD5128 Approved
0.5769 Remote Similarity NPD7320 Approved
0.5769 Remote Similarity NPD6899 Approved
0.5769 Remote Similarity NPD4729 Approved
0.5769 Remote Similarity NPD4730 Approved
0.5761 Remote Similarity NPD4690 Approved
0.5761 Remote Similarity NPD4138 Approved
0.5761 Remote Similarity NPD5205 Approved
0.5761 Remote Similarity NPD4693 Phase 3
0.5761 Remote Similarity NPD4688 Approved
0.5761 Remote Similarity NPD4689 Approved
0.5747 Remote Similarity NPD3617 Approved
0.5745 Remote Similarity NPD6051 Approved
0.5729 Remote Similarity NPD6399 Phase 3
0.5728 Remote Similarity NPD6640 Phase 3
0.5714 Remote Similarity NPD8379 Approved
0.5714 Remote Similarity NPD6014 Approved
0.5714 Remote Similarity NPD6012 Approved
0.5714 Remote Similarity NPD6373 Approved
0.5714 Remote Similarity NPD8380 Approved
0.5714 Remote Similarity NPD8296 Approved
0.5714 Remote Similarity NPD6372 Approved
0.5714 Remote Similarity NPD6013 Approved
0.5714 Remote Similarity NPD8378 Approved
0.5714 Remote Similarity NPD8335 Approved
0.57 Remote Similarity NPD6648 Approved
0.5673 Remote Similarity NPD6412 Phase 2
0.5663 Remote Similarity NPD4789 Approved
0.566 Remote Similarity NPD5249 Phase 3
0.566 Remote Similarity NPD5247 Approved
0.566 Remote Similarity NPD5248 Approved
0.566 Remote Similarity NPD6883 Approved
0.566 Remote Similarity NPD7290 Approved
0.566 Remote Similarity NPD5251 Approved
0.566 Remote Similarity NPD7102 Approved
0.566 Remote Similarity NPD5250 Approved
0.5648 Remote Similarity NPD4632 Approved
0.5638 Remote Similarity NPD4723 Approved
0.5638 Remote Similarity NPD4722 Approved
0.5636 Remote Similarity NPD7115 Discovery
0.5625 Remote Similarity NPD8377 Approved
0.5625 Remote Similarity NPD8294 Approved
0.5625 Remote Similarity NPD6411 Approved
0.5619 Remote Similarity NPD6686 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