Structure

Physi-Chem Properties

Molecular Weight:  392.13
Volume:  392.595
LogP:  3.966
LogD:  3.414
LogS:  -5.227
# Rotatable Bonds:  2
TPSA:  67.13
# H-Bond Aceptor:  6
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.637
Synthetic Accessibility Score:  3.056
Fsp3:  0.261
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:  -4.869
MDCK Permeability:  2.8535794626805e-05
Pgp-inhibitor:  0.998
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.048
Plasma Protein Binding (PPB):  89.6941909790039%
Volume Distribution (VD):  0.629
Pgp-substrate:  8.18327522277832%

ADMET: Metabolism

CYP1A2-inhibitor:  0.363
CYP1A2-substrate:  0.963
CYP2C19-inhibitor:  0.733
CYP2C19-substrate:  0.561
CYP2C9-inhibitor:  0.859
CYP2C9-substrate:  0.912
CYP2D6-inhibitor:  0.04
CYP2D6-substrate:  0.9
CYP3A4-inhibitor:  0.553
CYP3A4-substrate:  0.566

ADMET: Excretion

Clearance (CL):  2.561
Half-life (T1/2):  0.237

ADMET: Toxicity

hERG Blockers:  0.017
Human Hepatotoxicity (H-HT):  0.995
Drug-inuced Liver Injury (DILI):  0.983
AMES Toxicity:  0.684
Rat Oral Acute Toxicity:  0.537
Maximum Recommended Daily Dose:  0.448
Skin Sensitization:  0.11
Carcinogencity:  0.883
Eye Corrosion:  0.003
Eye Irritation:  0.016
Respiratory Toxicity:  0.859

Download Data

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

  Natural Product: NPC180340

Natural Product ID:  NPC180340
Common Name*:   Dehydrodeguelin
IUPAC Name:   n.a.
Synonyms:   Dehydrodeguelin
Standard InCHIKey:  NGQVFILFHVPLFE-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C23H20O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10H,11H2,1-4H3
SMILES:  COc1cc2c(cc1OC)OCc1c2c(=O)c2c(o1)c1C=CC(Oc1cc2)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL465673
PubChem CID:   3083803
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0001607] Rotenoids
          • [CHEMONTID:0003528] Rotenones

*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
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. whole plant n.a. DOI[10.1021/np50028a032]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10814365]
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. whole plant n.a. PMID[10993241]
NPO32669 derris malaccensis plain Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[11975515]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[12350137]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota rhizome n.a. n.a. PMID[12617587]
NPO626 Indigofera tinctoria Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16644212]
NPO16886 Amorpha fruticosa Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[18841906]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[23153397]
NPO8274 Geijera parviflora Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[23848189]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. leaf n.a. PMID[23901173]
NPO6485 Spiraea japonica Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[24684844]
NPO4520 Allium macrostemon Species Amaryllidaceae Eukaryota n.a. leaf n.a. PMID[26434122]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26476665]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[28068085]
NPO16886 Amorpha fruticosa Species Fabaceae Eukaryota Fruits n.a. n.a. PMID[28075580]
NPO16886 Amorpha fruticosa Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[8326318]
NPO16886 Amorpha fruticosa Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[8350086]
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[8759159]
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. whole plant n.a. PMID[8759159]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[9322358]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9584408]
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[9834152]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9868158]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizome Essent. Oil n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO5753 Glycosmis montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4520 Allium macrostemon Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3890 Scopolia japonica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6147 Eupatorium riparium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6485 Spiraea japonica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO626 Indigofera tinctoria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16886 Amorpha fruticosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO5753 Glycosmis montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16886 Amorpha fruticosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO439 Luffa operculata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6147 Eupatorium riparium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3890 Scopolia japonica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6485 Spiraea japonica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1007 Crotalaria paniculata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4520 Allium macrostemon Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO626 Indigofera tinctoria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3890 Scopolia japonica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30657 Lndigofera tinctoria n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6147 Eupatorium riparium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16886 Amorpha fruticosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4520 Allium macrostemon Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3890 Scopolia japonica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3890 Scopolia japonica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3129 Geum japonicum Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16886 Amorpha fruticosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8274 Geijera parviflora Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4520 Allium macrostemon Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1007 Crotalaria paniculata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5368 Achillea cretica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5753 Glycosmis montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12750 Cordia americana Species Cordiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO626 Indigofera tinctoria Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15101 Tricholoma panaeolum Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO439 Luffa operculata Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6485 Spiraea japonica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2671 Pedicularis semitorta Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6147 Eupatorium riparium Species Asteraceae 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
NPT1864 Cell Line L5178Y Mus musculus IC50 = 10200.0 nM PMID[473666]
NPT319 Cell Line B16 Mus musculus IC50 = 560.0 nM PMID[473667]
NPT4264 Cell Line Lewis lung carcinoma cell line IC50 = 560.0 nM PMID[473667]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 560.0 nM PMID[473667]
NPT451 Organism Helicobacter pylori Helicobacter pylori MIC = 4.0 ug.mL-1 PMID[473663]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 500000.0 nM PMID[473664]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 1200.0 nM PMID[473665]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 80000.0 nM PMID[473665]
NPT27 Others Unspecified IC50 > 80000.0 nM PMID[473665]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI = 40.0 % PMID[473665]
NPT2 Others Unspecified IC50 = 560.0 nM PMID[473667]

☑ 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 NPC180340 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
0.9865 High Similarity NPC128961
0.9732 High Similarity NPC472408
0.9664 High Similarity NPC166201
0.9608 High Similarity NPC40037
0.9539 High Similarity NPC19097
0.953 High Similarity NPC5840
0.953 High Similarity NPC189270
0.9481 High Similarity NPC165549
0.9419 High Similarity NPC18284
0.9419 High Similarity NPC273021
0.9419 High Similarity NPC261470
0.9404 High Similarity NPC40033
0.9346 High Similarity NPC248299
0.9329 High Similarity NPC205522
0.9299 High Similarity NPC475369
0.9299 High Similarity NPC50960
0.9286 High Similarity NPC476981
0.9267 High Similarity NPC10304
0.9267 High Similarity NPC63256
0.9262 High Similarity NPC215932
0.9262 High Similarity NPC120924
0.9262 High Similarity NPC110639
0.9262 High Similarity NPC106461
0.9262 High Similarity NPC195919
0.9262 High Similarity NPC14958
0.9262 High Similarity NPC40818
0.9262 High Similarity NPC216314
0.9257 High Similarity NPC182842
0.9231 High Similarity NPC259456
0.9216 High Similarity NPC186507
0.9205 High Similarity NPC238366
0.92 High Similarity NPC85233
0.9195 High Similarity NPC179970
0.9195 High Similarity NPC165512
0.9195 High Similarity NPC136278
0.9195 High Similarity NPC471590
0.9182 High Similarity NPC8965
0.9172 High Similarity NPC194427
0.9172 High Similarity NPC83922
0.9172 High Similarity NPC472448
0.9167 High Similarity NPC476980
0.9167 High Similarity NPC298093
0.9161 High Similarity NPC78071
0.9139 High Similarity NPC476342
0.9133 High Similarity NPC302408
0.9133 High Similarity NPC283002
0.9133 High Similarity NPC231013
0.9128 High Similarity NPC113089
0.9128 High Similarity NPC23955
0.9119 High Similarity NPC120593
0.9108 High Similarity NPC167678
0.9108 High Similarity NPC29876
0.9103 High Similarity NPC113055
0.9103 High Similarity NPC187792
0.9103 High Similarity NPC74178
0.9103 High Similarity NPC184755
0.9091 High Similarity NPC280937
0.9079 High Similarity NPC69752
0.906 High Similarity NPC70853
0.906 High Similarity NPC476054
0.906 High Similarity NPC9966
0.9051 High Similarity NPC229632
0.9045 High Similarity NPC204290
0.9038 High Similarity NPC473272
0.9038 High Similarity NPC284820
0.902 High Similarity NPC201547
0.902 High Similarity NPC259058
0.9012 High Similarity NPC475669
0.9006 High Similarity NPC177480
0.9 High Similarity NPC293201
0.9 High Similarity NPC173292
0.8994 High Similarity NPC306321
0.8994 High Similarity NPC65846
0.8994 High Similarity NPC303460
0.8993 High Similarity NPC185607
0.8993 High Similarity NPC214919
0.8993 High Similarity NPC124467
0.8993 High Similarity NPC29536
0.8987 High Similarity NPC198829
0.8987 High Similarity NPC258331
0.8987 High Similarity NPC34376
0.8981 High Similarity NPC204879
0.8974 High Similarity NPC303255
0.8974 High Similarity NPC282307
0.8974 High Similarity NPC170026
0.8974 High Similarity NPC276444
0.8974 High Similarity NPC471985
0.8974 High Similarity NPC472455
0.8968 High Similarity NPC472915
0.8961 High Similarity NPC208043
0.8961 High Similarity NPC198615
0.8961 High Similarity NPC308451
0.8961 High Similarity NPC226973
0.8961 High Similarity NPC262623
0.8954 High Similarity NPC181250
0.8951 High Similarity NPC103307
0.8951 High Similarity NPC74559
0.8951 High Similarity NPC472276
0.8947 High Similarity NPC299923
0.8947 High Similarity NPC470511
0.8938 High Similarity NPC239752
0.8938 High Similarity NPC472450
0.8938 High Similarity NPC275780
0.8931 High Similarity NPC474162
0.8931 High Similarity NPC81679
0.8931 High Similarity NPC474150
0.8931 High Similarity NPC302741
0.8931 High Similarity NPC52204
0.8926 High Similarity NPC58229
0.8924 High Similarity NPC192686
0.8924 High Similarity NPC119209
0.8924 High Similarity NPC118256
0.8924 High Similarity NPC475784
0.8917 High Similarity NPC218313
0.8917 High Similarity NPC36852
0.8917 High Similarity NPC181960
0.8917 High Similarity NPC476630
0.8917 High Similarity NPC310206
0.8917 High Similarity NPC218871
0.8917 High Similarity NPC52889
0.8917 High Similarity NPC474681
0.8917 High Similarity NPC262286
0.8917 High Similarity NPC78225
0.891 High Similarity NPC134287
0.891 High Similarity NPC472280
0.891 High Similarity NPC213622
0.891 High Similarity NPC200246
0.891 High Similarity NPC37392
0.891 High Similarity NPC39184
0.891 High Similarity NPC234255
0.891 High Similarity NPC20830
0.891 High Similarity NPC256612
0.891 High Similarity NPC256925
0.891 High Similarity NPC477530
0.891 High Similarity NPC130589
0.891 High Similarity NPC478238
0.891 High Similarity NPC472909
0.8903 High Similarity NPC134677
0.8896 High Similarity NPC156953
0.8896 High Similarity NPC239363
0.8896 High Similarity NPC29056
0.8896 High Similarity NPC306821
0.8889 High Similarity NPC242395
0.8889 High Similarity NPC471287
0.8889 High Similarity NPC152477
0.8882 High Similarity NPC310259
0.8882 High Similarity NPC128293
0.8882 High Similarity NPC472449
0.8882 High Similarity NPC39091
0.8882 High Similarity NPC272502
0.8875 High Similarity NPC189473
0.8875 High Similarity NPC23298
0.8874 High Similarity NPC59522
0.8868 High Similarity NPC474187
0.8868 High Similarity NPC134783
0.8868 High Similarity NPC474038
0.8868 High Similarity NPC266314
0.8868 High Similarity NPC57715
0.8861 High Similarity NPC469658
0.8861 High Similarity NPC152904
0.8861 High Similarity NPC250214
0.8861 High Similarity NPC95936
0.8854 High Similarity NPC68093
0.8854 High Similarity NPC133970
0.8854 High Similarity NPC6633
0.8854 High Similarity NPC472916
0.8854 High Similarity NPC470600
0.8854 High Similarity NPC5322
0.8854 High Similarity NPC191146
0.8854 High Similarity NPC138243
0.8846 High Similarity NPC183878
0.8846 High Similarity NPC22519
0.8846 High Similarity NPC124714
0.8846 High Similarity NPC274327
0.8846 High Similarity NPC145379
0.8846 High Similarity NPC47781
0.8846 High Similarity NPC69394
0.8846 High Similarity NPC255350
0.8846 High Similarity NPC176775
0.8846 High Similarity NPC86485
0.8846 High Similarity NPC170492
0.8846 High Similarity NPC478213
0.8846 High Similarity NPC231018
0.8846 High Similarity NPC160951
0.8841 High Similarity NPC310794
0.8839 High Similarity NPC117579
0.8839 High Similarity NPC474663
0.8839 High Similarity NPC149614
0.8839 High Similarity NPC279061
0.8831 High Similarity NPC328119
0.8827 High Similarity NPC471288
0.8827 High Similarity NPC243877
0.882 High Similarity NPC303174
0.882 High Similarity NPC234052
0.8812 High Similarity NPC474033
0.8812 High Similarity NPC475144
0.8812 High Similarity NPC474034
0.8812 High Similarity NPC329760
0.8812 High Similarity NPC220912
0.8805 High Similarity NPC477164

  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 NPC180340 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
0.9167 High Similarity NPD5494 Approved
0.8846 High Similarity NPD2801 Approved
0.8634 High Similarity NPD1247 Approved
0.8608 High Similarity NPD2393 Clinical (unspecified phase)
0.8553 High Similarity NPD3817 Phase 2
0.8544 High Similarity NPD1934 Approved
0.8533 High Similarity NPD2796 Approved
0.8385 Intermediate Similarity NPD3882 Suspended
0.8364 Intermediate Similarity NPD6166 Phase 2
0.8364 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8364 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8302 Intermediate Similarity NPD4380 Phase 2
0.8282 Intermediate Similarity NPD919 Approved
0.8269 Intermediate Similarity NPD1511 Approved
0.8263 Intermediate Similarity NPD3818 Discontinued
0.8217 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8214 Intermediate Similarity NPD7054 Approved
0.8214 Intermediate Similarity NPD5844 Phase 1
0.821 Intermediate Similarity NPD5402 Approved
0.8199 Intermediate Similarity NPD6801 Discontinued
0.8166 Intermediate Similarity NPD7074 Phase 3
0.8166 Intermediate Similarity NPD7472 Approved
0.8165 Intermediate Similarity NPD1512 Approved
0.8148 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8148 Intermediate Similarity NPD7819 Suspended
0.8129 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8113 Intermediate Similarity NPD920 Approved
0.8084 Intermediate Similarity NPD3926 Phase 2
0.8049 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8038 Intermediate Similarity NPD6799 Approved
0.8025 Intermediate Similarity NPD7411 Suspended
0.8024 Intermediate Similarity NPD6232 Discontinued
0.8023 Intermediate Similarity NPD7808 Phase 3
0.8012 Intermediate Similarity NPD6797 Phase 2
0.8 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7075 Discontinued
0.7988 Intermediate Similarity NPD7473 Discontinued
0.7987 Intermediate Similarity NPD1510 Phase 2
0.7965 Intermediate Similarity NPD7251 Discontinued
0.7964 Intermediate Similarity NPD6959 Discontinued
0.7949 Intermediate Similarity NPD1549 Phase 2
0.7895 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7888 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7875 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD6599 Discontinued
0.7785 Intermediate Similarity NPD1243 Approved
0.7778 Intermediate Similarity NPD5403 Approved
0.7764 Intermediate Similarity NPD5401 Approved
0.7756 Intermediate Similarity NPD3748 Approved
0.775 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD1240 Approved
0.7719 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD1465 Phase 2
0.7707 Intermediate Similarity NPD2935 Discontinued
0.7701 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD1607 Approved
0.7619 Intermediate Similarity NPD7768 Phase 2
0.7564 Intermediate Similarity NPD1933 Approved
0.7562 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD2800 Approved
0.7557 Intermediate Similarity NPD6559 Discontinued
0.7556 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD3750 Approved
0.75 Intermediate Similarity NPD943 Approved
0.7484 Intermediate Similarity NPD2313 Discontinued
0.7473 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD3749 Approved
0.7457 Intermediate Similarity NPD5242 Approved
0.7452 Intermediate Similarity NPD447 Suspended
0.7439 Intermediate Similarity NPD2534 Approved
0.7439 Intermediate Similarity NPD2533 Approved
0.7439 Intermediate Similarity NPD2532 Approved
0.7429 Intermediate Similarity NPD3751 Discontinued
0.7421 Intermediate Similarity NPD2799 Discontinued
0.7399 Intermediate Similarity NPD3787 Discontinued
0.7391 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD7286 Phase 2
0.738 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD3226 Approved
0.7355 Intermediate Similarity NPD6832 Phase 2
0.7351 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD2346 Discontinued
0.7314 Intermediate Similarity NPD2403 Approved
0.7303 Intermediate Similarity NPD5953 Discontinued
0.7278 Intermediate Similarity NPD6386 Approved
0.7278 Intermediate Similarity NPD6385 Approved
0.7267 Intermediate Similarity NPD1551 Phase 2
0.7251 Intermediate Similarity NPD5353 Approved
0.7241 Intermediate Similarity NPD7199 Phase 2
0.7235 Intermediate Similarity NPD6844 Discontinued
0.7233 Intermediate Similarity NPD230 Phase 1
0.7222 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7196 Intermediate Similarity NPD6778 Approved
0.7196 Intermediate Similarity NPD6779 Approved
0.7196 Intermediate Similarity NPD6776 Approved
0.7196 Intermediate Similarity NPD6777 Approved
0.7196 Intermediate Similarity NPD6782 Approved
0.7196 Intermediate Similarity NPD6780 Approved
0.7196 Intermediate Similarity NPD6781 Approved
0.7195 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD4628 Phase 3
0.7188 Intermediate Similarity NPD6651 Approved
0.717 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD1613 Approved
0.7169 Intermediate Similarity NPD7390 Discontinued
0.7169 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD37 Approved
0.7134 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD5536 Phase 2
0.7127 Intermediate Similarity NPD7549 Discontinued
0.7117 Intermediate Similarity NPD2344 Approved
0.7115 Intermediate Similarity NPD2798 Approved
0.711 Intermediate Similarity NPD4967 Phase 2
0.711 Intermediate Similarity NPD4965 Approved
0.711 Intermediate Similarity NPD4966 Approved
0.7101 Intermediate Similarity NPD1653 Approved
0.7089 Intermediate Similarity NPD3027 Phase 3
0.7088 Intermediate Similarity NPD8312 Approved
0.7088 Intermediate Similarity NPD8313 Approved
0.7083 Intermediate Similarity NPD7697 Approved
0.7083 Intermediate Similarity NPD7435 Discontinued
0.7083 Intermediate Similarity NPD7696 Phase 3
0.7083 Intermediate Similarity NPD7698 Approved
0.7076 Intermediate Similarity NPD5890 Approved
0.7076 Intermediate Similarity NPD5889 Approved
0.707 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD8434 Phase 2
0.7065 Intermediate Similarity NPD8150 Discontinued
0.7063 Intermediate Similarity NPD4307 Phase 2
0.7059 Intermediate Similarity NPD7458 Discontinued
0.7055 Intermediate Similarity NPD6100 Approved
0.7055 Intermediate Similarity NPD6099 Approved
0.7053 Intermediate Similarity NPD8285 Discontinued
0.7048 Intermediate Similarity NPD6190 Approved
0.7047 Intermediate Similarity NPD7871 Phase 2
0.7047 Intermediate Similarity NPD7870 Phase 2
0.7044 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD2654 Approved
0.7029 Intermediate Similarity NPD6234 Discontinued
0.7021 Intermediate Similarity NPD4363 Phase 3
0.7021 Intermediate Similarity NPD4360 Phase 2
0.7019 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD5124 Phase 1
0.7018 Intermediate Similarity NPD6585 Discontinued
0.7012 Intermediate Similarity NPD1471 Phase 3
0.7011 Intermediate Similarity NPD5019 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7229 Phase 3
0.6994 Remote Similarity NPD7033 Discontinued
0.6994 Remote Similarity NPD651 Clinical (unspecified phase)
0.6988 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6978 Remote Similarity NPD7685 Pre-registration
0.6974 Remote Similarity NPD7584 Approved
0.6968 Remote Similarity NPD3972 Approved
0.6962 Remote Similarity NPD9494 Approved
0.6962 Remote Similarity NPD3018 Phase 2
0.6946 Remote Similarity NPD3887 Approved
0.6946 Remote Similarity NPD2309 Approved
0.6944 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6944 Remote Similarity NPD7228 Approved
0.6943 Remote Similarity NPD3267 Approved
0.6943 Remote Similarity NPD3266 Approved
0.6943 Remote Similarity NPD6823 Phase 2
0.6939 Remote Similarity NPD7701 Phase 2
0.6931 Remote Similarity NPD6535 Approved
0.6931 Remote Similarity NPD6534 Approved
0.6919 Remote Similarity NPD7783 Phase 2
0.6919 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6918 Remote Similarity NPD4908 Phase 1
0.691 Remote Similarity NPD5711 Approved
0.691 Remote Similarity NPD5710 Approved
0.6904 Remote Similarity NPD8151 Discontinued
0.6899 Remote Similarity NPD1019 Discontinued
0.689 Remote Similarity NPD4308 Phase 3
0.6883 Remote Similarity NPD17 Approved
0.6882 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6879 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6869 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6869 Remote Similarity NPD7874 Approved
0.6867 Remote Similarity NPD1241 Discontinued
0.6867 Remote Similarity NPD2424 Discontinued
0.686 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6859 Remote Similarity NPD2981 Phase 2
0.6857 Remote Similarity NPD4288 Approved
0.6854 Remote Similarity NPD8127 Discontinued
0.6839 Remote Similarity NPD6279 Approved
0.6839 Remote Similarity NPD6280 Approved
0.6835 Remote Similarity NPD1203 Approved
0.6834 Remote Similarity NPD7801 Approved
0.6832 Remote Similarity NPD3268 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