Structure

Physi-Chem Properties

Molecular Weight:  152.12
Volume:  170.557
LogP:  2.594
LogD:  2.401
LogS:  -2.862
# Rotatable Bonds:  1
TPSA:  17.07
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.563
Synthetic Accessibility Score:  4.208
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:  -4.546
MDCK Permeability:  2.2534975869348273e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.049
30% Bioavailability (F30%):  0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.924
Plasma Protein Binding (PPB):  78.70320892333984%
Volume Distribution (VD):  0.859
Pgp-substrate:  32.31488800048828%

ADMET: Metabolism

CYP1A2-inhibitor:  0.513
CYP1A2-substrate:  0.595
CYP2C19-inhibitor:  0.124
CYP2C19-substrate:  0.91
CYP2C9-inhibitor:  0.074
CYP2C9-substrate:  0.158
CYP2D6-inhibitor:  0.024
CYP2D6-substrate:  0.438
CYP3A4-inhibitor:  0.253
CYP3A4-substrate:  0.342

ADMET: Excretion

Clearance (CL):  13.905
Half-life (T1/2):  0.756

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.241
Drug-inuced Liver Injury (DILI):  0.381
AMES Toxicity:  0.021
Rat Oral Acute Toxicity:  0.366
Maximum Recommended Daily Dose:  0.032
Skin Sensitization:  0.178
Carcinogencity:  0.27
Eye Corrosion:  0.839
Eye Irritation:  0.976
Respiratory Toxicity:  0.115

Download Data

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

  Natural Product: NPC83187

Natural Product ID:  NPC83187
Common Name*:   Thujone
IUPAC Name:   (1S,4R,5R)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one
Synonyms:  
Standard InCHIKey:  USMNOWBWPHYOEA-MRTMQBJTSA-N
Standard InCHI:  InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8-,10+/m1/s1
SMILES:  O=C1C[C@]2([C@@H]([C@H]1C)C2)C(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1444078
PubChem CID:   261491
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
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2009.03.042]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jep.2005.01.054]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.3136/fstr.15.499]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB10.140]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB2010.000-3252]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/JMPR.9000078]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[10096857]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. flower n.a. PMID[12130858]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota leaves n.a. n.a. PMID[14738379]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota dried aerial organs n.a. n.a. PMID[14738379]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota underground organs n.a. n.a. PMID[14738379]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota dried aerial organs n.a. n.a. PMID[14738379]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota roots and stolons n.a. n.a. PMID[14738379]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[17996677]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23507152]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers Tongxiang, China n.a. PMID[24621197]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[26099993]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28156114]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28248102]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[29400471]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Aerial Parts n.a. n.a. PMID[30726671]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[31181920]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[31418264]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[31815461]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO23226 Satureja montana Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO8545 Hyssopus officinalis Species Lamiaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8545 Hyssopus officinalis Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO8545 Hyssopus officinalis Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota Tissue Culture n.a. n.a. Database[FooDB]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO8545 Hyssopus officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8545 Hyssopus officinalis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23226 Satureja montana Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO8545 Hyssopus officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10492 Artemisia montana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6098 Salvia officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8545 Hyssopus officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10492 Artemisia montana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23226 Satureja montana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22258 Chrysanthemum indicum 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
NPO6098 NPC83187 Other Leaf 641.8 20 1263.6 mg/100g Database [DUKE]
NPO42012 NPC83187 Other Plant 24.15 8.4 39.9 mg/100g Database [DUKE]
NPO6098 NPC83187 Other Plant 775 250 1300 mg/100g Database [DUKE]
NPO23226 NPC83187 n.a. Plant 19.75 1 38.5 mg/100g Database [DUKE]
NPO21334 NPC83187 Other Shoot 33 6 60 mg/100g Database [DUKE]
NPO8545 NPC83187 Other Shoot 1.005 0.01 2 mg/100g Database [DUKE]

☑ 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
NPT210 Individual Protein Thyroid stimulating hormone receptor Homo sapiens Potency = 39810.7 nM PMID[450068]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 63095.7 nM PMID[450069]
NPT446 Individual Protein Rap guanine nucleotide exchange factor 3 Homo sapiens Potency n.a. 100000.0 nM PMID[450069]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 9466.2 nM PMID[450069]
NPT2 Others Unspecified Potency n.a. 23574.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 10919.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 3359.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 47448.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 66441.7 nM PubChem BioAssay data set
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 16511.3 nM PMID[450069]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 4147.5 nM PMID[450069]
NPT2 Others Unspecified Ki = 707945.78 nM PMID[450070]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. pAH50 = 3.0 n.a. PMID[450070]
NPT35 Others n.a. Vm = 1.132 10'-4m3/mol PMID[450070]
NPT32 Organism Mus musculus Mus musculus ED50 = 6.5 mg.kg-1 PMID[450071]
NPT32 Organism Mus musculus Mus musculus ED50 = 14.1 mg.kg-1 PMID[450071]
NPT32 Organism Mus musculus Mus musculus LD50 = 87.5 mg.kg-1 PMID[450071]

☑ 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 NPC83187 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 NPC285814
1.0 High Similarity NPC98246
0.9111 High Similarity NPC173996
0.9111 High Similarity NPC40249
0.9111 High Similarity NPC131981
0.8723 High Similarity NPC293343
0.8723 High Similarity NPC258672
0.8723 High Similarity NPC247786
0.8636 High Similarity NPC18397
0.8511 High Similarity NPC294440
0.8511 High Similarity NPC20017
0.8367 Intermediate Similarity NPC274182
0.8269 Intermediate Similarity NPC474105
0.814 Intermediate Similarity NPC223315
0.7778 Intermediate Similarity NPC59570
0.7778 Intermediate Similarity NPC45270
0.7778 Intermediate Similarity NPC215118
0.7778 Intermediate Similarity NPC135077
0.7736 Intermediate Similarity NPC184819
0.7593 Intermediate Similarity NPC143597
0.7593 Intermediate Similarity NPC151464
0.7556 Intermediate Similarity NPC141634
0.7547 Intermediate Similarity NPC288296
0.7547 Intermediate Similarity NPC53245
0.7292 Intermediate Similarity NPC171783
0.7288 Intermediate Similarity NPC128608
0.7143 Intermediate Similarity NPC49575
0.7143 Intermediate Similarity NPC55004
0.7143 Intermediate Similarity NPC267626
0.7069 Intermediate Similarity NPC270042
0.7049 Intermediate Similarity NPC168824
0.7049 Intermediate Similarity NPC189917
0.7049 Intermediate Similarity NPC39462
0.7049 Intermediate Similarity NPC107704
0.7049 Intermediate Similarity NPC96812
0.6842 Remote Similarity NPC230823
0.6833 Remote Similarity NPC165695
0.6833 Remote Similarity NPC472306
0.678 Remote Similarity NPC25853
0.6724 Remote Similarity NPC30215
0.6724 Remote Similarity NPC266295
0.6724 Remote Similarity NPC94991
0.6719 Remote Similarity NPC474962
0.6719 Remote Similarity NPC477857
0.6667 Remote Similarity NPC236623
0.6615 Remote Similarity NPC477856
0.6615 Remote Similarity NPC214770
0.661 Remote Similarity NPC259261
0.6607 Remote Similarity NPC319589
0.6552 Remote Similarity NPC192427
0.6515 Remote Similarity NPC473267
0.6515 Remote Similarity NPC5701
0.6512 Remote Similarity NPC321646
0.6508 Remote Similarity NPC43300
0.6491 Remote Similarity NPC200258
0.6491 Remote Similarity NPC307063
0.6452 Remote Similarity NPC473902
0.6444 Remote Similarity NPC248190
0.6418 Remote Similarity NPC474123
0.6406 Remote Similarity NPC478180
0.6406 Remote Similarity NPC474221
0.6406 Remote Similarity NPC130459
0.6393 Remote Similarity NPC475795
0.6393 Remote Similarity NPC213152
0.6383 Remote Similarity NPC69245
0.6324 Remote Similarity NPC255021
0.6308 Remote Similarity NPC473225
0.6308 Remote Similarity NPC20610
0.6304 Remote Similarity NPC121215
0.6296 Remote Similarity NPC127997
0.6296 Remote Similarity NPC95969
0.6279 Remote Similarity NPC79887
0.6279 Remote Similarity NPC153439
0.6279 Remote Similarity NPC196434
0.6279 Remote Similarity NPC222997
0.6279 Remote Similarity NPC42403
0.6279 Remote Similarity NPC4962
0.6279 Remote Similarity NPC221192
0.6279 Remote Similarity NPC29561
0.6271 Remote Similarity NPC115385
0.625 Remote Similarity NPC323005
0.6232 Remote Similarity NPC255650
0.6232 Remote Similarity NPC273366
0.6212 Remote Similarity NPC182815
0.619 Remote Similarity NPC285371
0.619 Remote Similarity NPC212210
0.6182 Remote Similarity NPC116906
0.6167 Remote Similarity NPC127798
0.6143 Remote Similarity NPC69408
0.6136 Remote Similarity NPC168982
0.6119 Remote Similarity NPC307176
0.6119 Remote Similarity NPC151045
0.6119 Remote Similarity NPC477850
0.6119 Remote Similarity NPC40574
0.6119 Remote Similarity NPC159577
0.6119 Remote Similarity NPC246722
0.6119 Remote Similarity NPC35734
0.6119 Remote Similarity NPC108131
0.6119 Remote Similarity NPC282593
0.6102 Remote Similarity NPC20603
0.6094 Remote Similarity NPC157518
0.6066 Remote Similarity NPC143834
0.6056 Remote Similarity NPC264602
0.6056 Remote Similarity NPC475031
0.6047 Remote Similarity NPC295442
0.6047 Remote Similarity NPC38859
0.6047 Remote Similarity NPC198118
0.6032 Remote Similarity NPC32285
0.6029 Remote Similarity NPC115023
0.6029 Remote Similarity NPC311102
0.6029 Remote Similarity NPC234707
0.6029 Remote Similarity NPC304983
0.6029 Remote Similarity NPC156277
0.6029 Remote Similarity NPC223187
0.6029 Remote Similarity NPC151018
0.6029 Remote Similarity NPC305501
0.6029 Remote Similarity NPC110615
0.6029 Remote Similarity NPC197701
0.6029 Remote Similarity NPC320549
0.6029 Remote Similarity NPC58057
0.6029 Remote Similarity NPC470078
0.6 Remote Similarity NPC268596
0.6 Remote Similarity NPC225318
0.6 Remote Similarity NPC16578
0.6 Remote Similarity NPC76608
0.6 Remote Similarity NPC42060
0.6 Remote Similarity NPC72444
0.6 Remote Similarity NPC149101
0.6 Remote Similarity NPC477931
0.6 Remote Similarity NPC268736
0.5972 Remote Similarity NPC478128
0.597 Remote Similarity NPC321732
0.597 Remote Similarity NPC6120
0.597 Remote Similarity NPC196197
0.597 Remote Similarity NPC324607
0.597 Remote Similarity NPC469677
0.597 Remote Similarity NPC61702
0.597 Remote Similarity NPC327728
0.597 Remote Similarity NPC162867
0.597 Remote Similarity NPC131892
0.597 Remote Similarity NPC213178
0.597 Remote Similarity NPC139397
0.5957 Remote Similarity NPC218357
0.5942 Remote Similarity NPC107783
0.5942 Remote Similarity NPC92909
0.5942 Remote Similarity NPC248567
0.5942 Remote Similarity NPC52667
0.5942 Remote Similarity NPC232112
0.5942 Remote Similarity NPC303613
0.5942 Remote Similarity NPC310766
0.5942 Remote Similarity NPC470044
0.5942 Remote Similarity NPC470045
0.5942 Remote Similarity NPC251705
0.5942 Remote Similarity NPC474228
0.5915 Remote Similarity NPC20466
0.5909 Remote Similarity NPC475523
0.5902 Remote Similarity NPC27610
0.5902 Remote Similarity NPC56905
0.589 Remote Similarity NPC52951
0.5882 Remote Similarity NPC265782
0.5882 Remote Similarity NPC260040
0.5882 Remote Similarity NPC251929
0.5882 Remote Similarity NPC2634
0.5882 Remote Similarity NPC476731
0.5873 Remote Similarity NPC60565
0.5873 Remote Similarity NPC253204
0.5873 Remote Similarity NPC97322
0.5862 Remote Similarity NPC474141
0.5857 Remote Similarity NPC254340
0.5857 Remote Similarity NPC159497
0.5857 Remote Similarity NPC472854
0.5846 Remote Similarity NPC470329
0.5821 Remote Similarity NPC474954
0.5818 Remote Similarity NPC13105
0.5814 Remote Similarity NPC100997
0.5806 Remote Similarity NPC96551
0.5806 Remote Similarity NPC285594
0.5797 Remote Similarity NPC89310
0.5797 Remote Similarity NPC126642
0.5797 Remote Similarity NPC54123
0.5797 Remote Similarity NPC472309
0.5789 Remote Similarity NPC27438
0.5781 Remote Similarity NPC167256
0.5775 Remote Similarity NPC472311
0.5775 Remote Similarity NPC125767
0.5775 Remote Similarity NPC293803
0.5775 Remote Similarity NPC132064
0.5775 Remote Similarity NPC21220
0.5775 Remote Similarity NPC195155
0.5775 Remote Similarity NPC97534
0.5775 Remote Similarity NPC174964
0.5763 Remote Similarity NPC63396
0.5763 Remote Similarity NPC202850
0.5758 Remote Similarity NPC473899
0.5753 Remote Similarity NPC321690
0.5741 Remote Similarity NPC314679
0.5735 Remote Similarity NPC476734
0.5735 Remote Similarity NPC319671
0.5735 Remote Similarity NPC252032
0.5735 Remote Similarity NPC64466

  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 NPC83187 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
0.9111 High Similarity NPD344 Approved
0.9111 High Similarity NPD345 Approved
0.9111 High Similarity NPD343 Approved
0.6613 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6308 Remote Similarity NPD5360 Phase 3
0.6308 Remote Similarity NPD5361 Clinical (unspecified phase)
0.625 Remote Similarity NPD4224 Phase 2
0.6119 Remote Similarity NPD4747 Approved
0.6119 Remote Similarity NPD4789 Approved
0.6078 Remote Similarity NPD387 Clinical (unspecified phase)
0.6061 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6029 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6029 Remote Similarity NPD4758 Discontinued
0.6029 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6029 Remote Similarity NPD6081 Approved
0.597 Remote Similarity NPD3698 Phase 2
0.597 Remote Similarity NPD4137 Phase 3
0.597 Remote Similarity NPD3700 Clinical (unspecified phase)
0.597 Remote Similarity NPD3699 Clinical (unspecified phase)
0.5882 Remote Similarity NPD4245 Approved
0.5882 Remote Similarity NPD4244 Approved
0.5882 Remote Similarity NPD4691 Approved
0.5857 Remote Similarity NPD4687 Approved
0.5857 Remote Similarity NPD5733 Approved
0.5806 Remote Similarity NPD3198 Approved
0.5797 Remote Similarity NPD5777 Approved
0.5797 Remote Similarity NPD5276 Approved
0.5763 Remote Similarity NPD615 Clinical (unspecified phase)
0.5741 Remote Similarity NPD634 Phase 3
0.569 Remote Similarity NPD3186 Phase 1
0.5634 Remote Similarity NPD4058 Approved
0.5634 Remote Similarity NPD6113 Clinical (unspecified phase)

  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