Structure

Physi-Chem Properties

Molecular Weight:  152.12
Volume:  170.557
LogP:  2.269
LogD:  2.255
LogS:  -1.98
# Rotatable Bonds:  0
TPSA:  17.07
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.521
Synthetic Accessibility Score:  4.468
Fsp3:  0.9
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.618
MDCK Permeability:  2.3614458768861368e-05
Pgp-inhibitor:  0.007
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.027
30% Bioavailability (F30%):  0.091

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.357
Plasma Protein Binding (PPB):  69.97142028808594%
Volume Distribution (VD):  0.821
Pgp-substrate:  46.22468185424805%

ADMET: Metabolism

CYP1A2-inhibitor:  0.036
CYP1A2-substrate:  0.895
CYP2C19-inhibitor:  0.465
CYP2C19-substrate:  0.915
CYP2C9-inhibitor:  0.1
CYP2C9-substrate:  0.545
CYP2D6-inhibitor:  0.011
CYP2D6-substrate:  0.274
CYP3A4-inhibitor:  0.261
CYP3A4-substrate:  0.609

ADMET: Excretion

Clearance (CL):  13.149
Half-life (T1/2):  0.487

ADMET: Toxicity

hERG Blockers:  0.004
Human Hepatotoxicity (H-HT):  0.339
Drug-inuced Liver Injury (DILI):  0.095
AMES Toxicity:  0.015
Rat Oral Acute Toxicity:  0.264
Maximum Recommended Daily Dose:  0.467
Skin Sensitization:  0.124
Carcinogencity:  0.749
Eye Corrosion:  0.939
Eye Irritation:  0.923
Respiratory Toxicity:  0.978

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  Natural Product: NPC247786

Natural Product ID:  NPC247786
Common Name*:   (+)-Fenchone
IUPAC Name:   (4S)-2,2,4-trimethylbicyclo[2.2.1]heptan-3-one
Synonyms:  
Standard InCHIKey:  LHXDLQBQYFFVNW-MHPPCMCBSA-N
Standard InCHI:  InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3/t7?,10-/m0/s1
SMILES:  O=C1[C@@]2(C)CCC(C1(C)C)C2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2269328
PubChem CID:   12049113
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. fruit n.a. DOI[10.1007/s00217-007-0799-1]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. flower n.a. DOI[10.1016/j.foodchem.2011.01.077]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. leaf n.a. DOI[10.1016/S0031-9422(00)94055-X]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. flower n.a. DOI[10.3390/70200245]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[11520216]
NPO21349 Punica granatum Species Lythraceae Eukaryota Seeds n.a. n.a. PMID[15620261]
NPO28260 Senna alexandrina Species Fabaceae Eukaryota n.a. seed n.a. PMID[17345316]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. flower bud n.a. PMID[17628872]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[19370929]
NPO25197 Magnolia sprengeri Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[22080044]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota roots n.a. n.a. PMID[22381047]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[24617303]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. flower bud n.a. PMID[7779269]
NPO21349 Punica granatum Species Lythraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Root Bark n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Stem Bark n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Twig n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO11820 Amomum villosum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1479 Amomum longiligulare Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1918 Magnolia kobus Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1631 Amomum xanthioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15064 Magnolia denudata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25197 Magnolia sprengeri Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO21349 Punica granatum Species Lythraceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15064 Magnolia denudata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1631 Amomum xanthioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11820 Amomum villosum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25197 Magnolia sprengeri Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12322 Amomum krervanh Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1918 Magnolia kobus Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28260 Senna alexandrina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1479 Amomum longiligulare Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1631 Amomum xanthioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15064 Magnolia denudata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12468 Asarum heterotropoides Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1918 Magnolia kobus Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15064 Magnolia denudata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1479 Amomum longiligulare Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28260 Senna alexandrina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29078 Asiasarum sieboldii n.a. n.a. n.a. n.a. n.a. n.a. Database[TM-MC]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1631 Amomum xanthioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11820 Amomum villosum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12322 Amomum krervanh Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4659 Asiasarum heterotropoides n.a. n.a. n.a. n.a. n.a. n.a. Database[TM-MC]
NPO29010 Amomum compactum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12468 Asarum heterotropoides Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25197 Magnolia sprengeri Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4659 Asiasarum heterotropoides n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11820 Amomum villosum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15064 Magnolia denudata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1631 Amomum xanthioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25197 Magnolia sprengeri Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28260 Senna alexandrina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12468 Asarum heterotropoides Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12322 Amomum krervanh Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1918 Magnolia kobus Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29078 Asiasarum sieboldii n.a. n.a. n.a. 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
NPT2557 Organism Dermatophagoides pteronyssinus Dermatophagoides pteronyssinus Ratio = 1.6 n.a. PMID[495138]
NPT2525 Organism Dermatophagoides farinae Dermatophagoides farinae Ratio = 2.3 n.a. PMID[495138]
NPT2557 Organism Dermatophagoides pteronyssinus Dermatophagoides pteronyssinus LD50 = 43.2 mg/m2 PMID[495138]
NPT2525 Organism Dermatophagoides farinae Dermatophagoides farinae LD50 = 38.9 mg/m2 PMID[495138]

☑ 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 NPC247786 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC258672
1.0 High Similarity NPC293343
0.9778 High Similarity NPC294440
0.9574 High Similarity NPC274182
0.9556 High Similarity NPC173996
0.9556 High Similarity NPC40249
0.9556 High Similarity NPC131981
0.8936 High Similarity NPC20017
0.8723 High Similarity NPC98246
0.8723 High Similarity NPC83187
0.8723 High Similarity NPC285814
0.8113 Intermediate Similarity NPC184819
0.8036 Intermediate Similarity NPC270042
0.7963 Intermediate Similarity NPC143597
0.7963 Intermediate Similarity NPC151464
0.7963 Intermediate Similarity NPC474105
0.7925 Intermediate Similarity NPC53245
0.7925 Intermediate Similarity NPC288296
0.7778 Intermediate Similarity NPC223315
0.75 Intermediate Similarity NPC18397
0.7458 Intermediate Similarity NPC472306
0.7447 Intermediate Similarity NPC59570
0.7447 Intermediate Similarity NPC135077
0.7447 Intermediate Similarity NPC215118
0.7447 Intermediate Similarity NPC45270
0.7347 Intermediate Similarity NPC171783
0.7234 Intermediate Similarity NPC141634
0.7049 Intermediate Similarity NPC128608
0.6897 Remote Similarity NPC267626
0.6897 Remote Similarity NPC49575
0.6897 Remote Similarity NPC55004
0.6842 Remote Similarity NPC307063
0.6842 Remote Similarity NPC200258
0.6825 Remote Similarity NPC43300
0.6825 Remote Similarity NPC168824
0.6825 Remote Similarity NPC96812
0.6825 Remote Similarity NPC39462
0.6825 Remote Similarity NPC189917
0.6825 Remote Similarity NPC107704
0.6727 Remote Similarity NPC236623
0.6721 Remote Similarity NPC213152
0.6716 Remote Similarity NPC248567
0.6716 Remote Similarity NPC52667
0.6615 Remote Similarity NPC473225
0.6615 Remote Similarity NPC20610
0.6613 Remote Similarity NPC165695
0.661 Remote Similarity NPC230823
0.6567 Remote Similarity NPC197701
0.6562 Remote Similarity NPC323005
0.6557 Remote Similarity NPC25853
0.6522 Remote Similarity NPC132064
0.6515 Remote Similarity NPC477857
0.6515 Remote Similarity NPC474962
0.6515 Remote Similarity NPC182815
0.6508 Remote Similarity NPC212210
0.65 Remote Similarity NPC94991
0.65 Remote Similarity NPC266295
0.65 Remote Similarity NPC127798
0.65 Remote Similarity NPC30215
0.6418 Remote Similarity NPC35734
0.6418 Remote Similarity NPC307176
0.6418 Remote Similarity NPC214770
0.6418 Remote Similarity NPC40574
0.6418 Remote Similarity NPC477856
0.6418 Remote Similarity NPC282593
0.6418 Remote Similarity NPC108131
0.6418 Remote Similarity NPC159577
0.6393 Remote Similarity NPC259261
0.6379 Remote Similarity NPC319589
0.6379 Remote Similarity NPC202146
0.6379 Remote Similarity NPC32222
0.6338 Remote Similarity NPC169389
0.6338 Remote Similarity NPC475932
0.6338 Remote Similarity NPC74685
0.6324 Remote Similarity NPC110615
0.6324 Remote Similarity NPC234707
0.6324 Remote Similarity NPC58057
0.6324 Remote Similarity NPC305501
0.6324 Remote Similarity NPC5701
0.6324 Remote Similarity NPC320549
0.6324 Remote Similarity NPC151018
0.6324 Remote Similarity NPC473267
0.6324 Remote Similarity NPC470078
0.6324 Remote Similarity NPC223187
0.6324 Remote Similarity NPC115023
0.6324 Remote Similarity NPC156277
0.6308 Remote Similarity NPC42060
0.6308 Remote Similarity NPC268736
0.6308 Remote Similarity NPC477931
0.629 Remote Similarity NPC84218
0.6286 Remote Similarity NPC155441
0.6269 Remote Similarity NPC213178
0.6269 Remote Similarity NPC196197
0.6269 Remote Similarity NPC139397
0.6269 Remote Similarity NPC324607
0.6269 Remote Similarity NPC321732
0.6269 Remote Similarity NPC131892
0.6269 Remote Similarity NPC327728
0.6269 Remote Similarity NPC6120
0.625 Remote Similarity NPC228911
0.625 Remote Similarity NPC116906
0.625 Remote Similarity NPC473902
0.6232 Remote Similarity NPC474123
0.6232 Remote Similarity NPC470044
0.6232 Remote Similarity NPC474228
0.6232 Remote Similarity NPC310766
0.6232 Remote Similarity NPC470045
0.6232 Remote Similarity NPC303613
0.6232 Remote Similarity NPC251705
0.6232 Remote Similarity NPC232112
0.6222 Remote Similarity NPC321646
0.6212 Remote Similarity NPC474221
0.6212 Remote Similarity NPC478180
0.6212 Remote Similarity NPC475523
0.6212 Remote Similarity NPC130459
0.619 Remote Similarity NPC475795
0.619 Remote Similarity NPC60565
0.619 Remote Similarity NPC83088
0.6176 Remote Similarity NPC251929
0.6176 Remote Similarity NPC2634
0.6176 Remote Similarity NPC265782
0.6176 Remote Similarity NPC260040
0.6176 Remote Similarity NPC476731
0.617 Remote Similarity NPC248190
0.6154 Remote Similarity NPC157518
0.6143 Remote Similarity NPC255021
0.6143 Remote Similarity NPC472854
0.6143 Remote Similarity NPC159497
0.6143 Remote Similarity NPC254340
0.6122 Remote Similarity NPC69245
0.6087 Remote Similarity NPC472309
0.6087 Remote Similarity NPC89310
0.6087 Remote Similarity NPC54123
0.6087 Remote Similarity NPC126642
0.6066 Remote Similarity NPC115385
0.6066 Remote Similarity NPC192427
0.6066 Remote Similarity NPC150713
0.6066 Remote Similarity NPC29976
0.6061 Remote Similarity NPC176171
0.6056 Remote Similarity NPC255650
0.6056 Remote Similarity NPC472311
0.6056 Remote Similarity NPC174964
0.6056 Remote Similarity NPC97534
0.6056 Remote Similarity NPC21220
0.6056 Remote Similarity NPC195155
0.6056 Remote Similarity NPC273366
0.6056 Remote Similarity NPC72444
0.6056 Remote Similarity NPC293803
0.6056 Remote Similarity NPC125767
0.6042 Remote Similarity NPC121215
0.6038 Remote Similarity NPC141777
0.6038 Remote Similarity NPC166362
0.6038 Remote Similarity NPC227670
0.6032 Remote Similarity NPC66145
0.6032 Remote Similarity NPC127582
0.6032 Remote Similarity NPC478126
0.6029 Remote Similarity NPC252032
0.6029 Remote Similarity NPC469941
0.6029 Remote Similarity NPC319671
0.6029 Remote Similarity NPC64466
0.6029 Remote Similarity NPC476734
0.6 Remote Similarity NPC469662
0.6 Remote Similarity NPC79887
0.6 Remote Similarity NPC285371
0.6 Remote Similarity NPC475124
0.6 Remote Similarity NPC196434
0.6 Remote Similarity NPC42403
0.6 Remote Similarity NPC221192
0.6 Remote Similarity NPC222997
0.6 Remote Similarity NPC6697
0.6 Remote Similarity NPC29561
0.6 Remote Similarity NPC4962
0.6 Remote Similarity NPC153439
0.5972 Remote Similarity NPC475742
0.5972 Remote Similarity NPC5767
0.5972 Remote Similarity NPC69408
0.5972 Remote Similarity NPC472487
0.5972 Remote Similarity NPC472486
0.5968 Remote Similarity NPC27610
0.5968 Remote Similarity NPC56905
0.5946 Remote Similarity NPC31302
0.5946 Remote Similarity NPC245029
0.5942 Remote Similarity NPC246722
0.5942 Remote Similarity NPC151045
0.5942 Remote Similarity NPC477929
0.5942 Remote Similarity NPC477850
0.5938 Remote Similarity NPC306750
0.5915 Remote Similarity NPC474796
0.5915 Remote Similarity NPC280026
0.5915 Remote Similarity NPC474797
0.5915 Remote Similarity NPC167702
0.5915 Remote Similarity NPC133922
0.5915 Remote Similarity NPC309852
0.5915 Remote Similarity NPC329866
0.5909 Remote Similarity NPC469791
0.5902 Remote Similarity NPC20603
0.589 Remote Similarity NPC23884
0.589 Remote Similarity NPC264602
0.589 Remote Similarity NPC477918
0.589 Remote Similarity NPC471151

  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 NPC247786 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
0.9556 High Similarity NPD345 Approved
0.9556 High Similarity NPD343 Approved
0.9556 High Similarity NPD344 Approved
0.6935 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6615 Remote Similarity NPD5360 Phase 3
0.6615 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6562 Remote Similarity NPD4224 Phase 2
0.6418 Remote Similarity NPD4747 Approved
0.6418 Remote Similarity NPD4789 Approved
0.6364 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6324 Remote Similarity NPD6081 Approved
0.6324 Remote Similarity NPD4758 Discontinued
0.6324 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6324 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6269 Remote Similarity NPD3698 Phase 2
0.6269 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6269 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6269 Remote Similarity NPD4137 Phase 3
0.6176 Remote Similarity NPD4244 Approved
0.6176 Remote Similarity NPD4691 Approved
0.6176 Remote Similarity NPD4245 Approved
0.6143 Remote Similarity NPD5733 Approved
0.6143 Remote Similarity NPD4687 Approved
0.6087 Remote Similarity NPD5777 Approved
0.6087 Remote Similarity NPD5276 Approved
0.5915 Remote Similarity NPD6113 Clinical (unspecified phase)
0.5915 Remote Similarity NPD4058 Approved
0.5849 Remote Similarity NPD387 Clinical (unspecified phase)
0.5833 Remote Similarity NPD3703 Phase 2
0.5833 Remote Similarity NPD3702 Approved
0.5811 Remote Similarity NPD5364 Discontinued
0.5753 Remote Similarity NPD6117 Approved
0.5714 Remote Similarity NPD287 Approved
0.5676 Remote Similarity NPD6116 Phase 1
0.5625 Remote Similarity NPD3198 Approved
0.56 Remote Similarity NPD6115 Approved
0.56 Remote Similarity NPD3671 Phase 1
0.56 Remote Similarity NPD4777 Suspended
0.56 Remote Similarity NPD6118 Approved
0.56 Remote Similarity NPD6114 Approved
0.56 Remote Similarity NPD3617 Approved
0.56 Remote Similarity NPD6697 Approved
0.56 Remote Similarity NPD4776 Phase 2

  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