Structure

Physi-Chem Properties

Molecular Weight:  248.14
Volume:  260.788
LogP:  2.948
LogD:  3.467
LogS:  -3.903
# Rotatable Bonds:  0
TPSA:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.529
Synthetic Accessibility Score:  4.523
Fsp3:  0.667
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:  -4.666
MDCK Permeability:  1.8957747670356184e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.614
Plasma Protein Binding (PPB):  77.92601013183594%
Volume Distribution (VD):  0.884
Pgp-substrate:  22.920917510986328%

ADMET: Metabolism

CYP1A2-inhibitor:  0.264
CYP1A2-substrate:  0.699
CYP2C19-inhibitor:  0.676
CYP2C19-substrate:  0.791
CYP2C9-inhibitor:  0.454
CYP2C9-substrate:  0.074
CYP2D6-inhibitor:  0.154
CYP2D6-substrate:  0.12
CYP3A4-inhibitor:  0.847
CYP3A4-substrate:  0.311

ADMET: Excretion

Clearance (CL):  9.841
Half-life (T1/2):  0.16

ADMET: Toxicity

hERG Blockers:  0.028
Human Hepatotoxicity (H-HT):  0.105
Drug-inuced Liver Injury (DILI):  0.158
AMES Toxicity:  0.664
Rat Oral Acute Toxicity:  0.263
Maximum Recommended Daily Dose:  0.942
Skin Sensitization:  0.285
Carcinogencity:  0.836
Eye Corrosion:  0.037
Eye Irritation:  0.321
Respiratory Toxicity:  0.684

Download Data

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

  Natural Product: NPC10636

Natural Product ID:  NPC10636
Common Name*:   Atractylenolide Iii
IUPAC Name:   (4aS,8aR,9aS)-9a-hydroxy-3,8a-dimethyl-5-methylidene-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran-2-one
Synonyms:   Atractylenolide Iii
Standard InCHIKey:  FBMORZZOJSDNRQ-GLQYFDAESA-N
Standard InCHI:  InChI=1S/C15H20O3/c1-9-5-4-6-14(3)8-15(17)12(7-11(9)14)10(2)13(16)18-15/h11,17H,1,4-8H2,2-3H3/t11-,14+,15-/m0/s1
SMILES:  C=C1CCC[C@]2([C@H]1CC1=C(C)C(=O)O[C@]1(C2)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL486961
PubChem CID:   155948
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001543] Sesquiterpene lactones
            • [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits Spanish DOI[10.1021/jf00010a019]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. DOI[10.1021/jf00016a013]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota n.a. Germany DOI[10.1021/jf00016a013]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota n.a. Italy DOI[10.1021/jf00016a013]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits Turkey DOI[10.1111/j.1745-4557.2003.tb00250.x]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. DOI[10.17660/ActaHortic.2003.610.16]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[10794642]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[10820090]
NPO8063 Clerodendrum calamitosum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[11473423]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[11754554]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[15019787]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[15315387]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[16076125]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[16920856]
NPO29391 Papaver bracteatum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[17226487]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[17432574]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. rhizome n.a. PMID[18787781]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[19358604]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[21190690]
NPO14376 Stephania cephalantha Species Menispermaceae Eukaryota n.a. leaf n.a. PMID[21214233]
NPO14376 Stephania cephalantha Species Menispermaceae Eukaryota n.a. stem n.a. PMID[21214233]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[21302967]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[22029392]
NPO6674 Burkholderia ambifaria Species Burkholderiaceae Bacteria n.a. n.a. n.a. PMID[22988812]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[23394984]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota n.a. Germany PMID[23394984]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota n.a. New Zealand PMID[23394984]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[23517479]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[2413754]
NPO17386 Securidaca longepedunculata Species Polygalaceae Eukaryota n.a. n.a. n.a. PMID[24216090]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[27228227]
NPO26787 Chloranthus anhuiensis Species Chloranthaceae Eukaryota n.a. n.a. n.a. PMID[29775304]
NPO11257 Momordica dioica Species Cucurbitaceae Eukaryota n.a. n.a. n.a. PMID[30673219]
NPO40789 Atractylodes rhizomes Species Asteraceae Eukaryota Rhizomes n.a. n.a. PMID[6418860]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[9542132]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[9544564]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota Latex Exudate n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. Database[FooDB]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12584 Atractylodes chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29391 Papaver bracteatum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11097 Lepidium apetalum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12584 Atractylodes chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14959.1 Codonopsis pilosula subsp. tangshen Subspecies Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11097 Lepidium apetalum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14376 Stephania cephalantha Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11257 Momordica dioica Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29391 Papaver bracteatum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11097 Lepidium apetalum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12584 Atractylodes chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29391 Papaver bracteatum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11257 Momordica dioica Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11097 Lepidium apetalum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12584 Atractylodes chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14959.1 Codonopsis pilosula subsp. tangshen Subspecies Campanulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12192 Coronilla scorpioides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO468 Dryopteris oligophlebia Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16164 Podocarpus urbani Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7345 Ptilonia magellanica Species Bonnemaisoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29391 Papaver bracteatum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8484 Codonopsis lanceolata Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8063 Clerodendrum calamitosum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11097 Lepidium apetalum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO936 Pinalia spicata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5827 Dalea tuberculata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6674 Burkholderia ambifaria Species Burkholderiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10738 Cotoneaster horizontalis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9928 Cephalaria cilicica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5013 Loranthus spicatus Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9040 Elsinoe annonae Species Elsinoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11555 Pterocaulon purpurascens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11815 Mikania hirsutissima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12584 Atractylodes chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17386 Securidaca longepedunculata Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11257 Momordica dioica Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19898 Stevia lucida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5392 Pachycereus pecten-aboriginum Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14959.1 Codonopsis pilosula subsp. tangshen Subspecies Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10355 Echinopsis macrogona Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6256 Eucalyptus umbra Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12891 Minasia alpestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26787 Chloranthus anhuiensis Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3740 Trisetum flavescens Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10399 Manfreda virginica Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3385 Cassine transvaalensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7048 Eucalyptus rariflora Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9512 Phlomis fruticosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1185 Stereocaulon strictum Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9307 Ficus indica Species Ficidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12998 Salvia rubescens Species Lamiaceae 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
NPT1135 Cell Line Hepatocyte Rattus norvegicus Activity = 103.0 % PMID[507729]
NPT1135 Cell Line Hepatocyte Rattus norvegicus Activity = 97.0 % PMID[507729]
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens IC50 > 200000.0 nM PMID[507730]
NPT30 Individual Protein Cyclooxygenase-1 Homo sapiens IC50 > 200000.0 nM PMID[507730]
NPT542 Individual Protein Progesterone receptor Homo sapiens RLU = 1.57 n.a. PMID[507732]
NPT542 Individual Protein Progesterone receptor Homo sapiens RLU = 3.39 n.a. PMID[507732]
NPT540 Individual Protein Bile acid receptor FXR Homo sapiens FC = 1.5 n.a. PMID[507732]
NPT540 Individual Protein Bile acid receptor FXR Homo sapiens RLU = 1.7 n.a. PMID[507732]
NPT540 Individual Protein Bile acid receptor FXR Homo sapiens Inhibition = 50.0 % PMID[507732]
NPT540 Individual Protein Bile acid receptor FXR Homo sapiens RLU = 0.85 n.a. PMID[507732]
NPT681 Cell Line PC-12 Rattus norvegicus EC50 = 36300.0 nM PMID[507734]
NPT913 Cell Line CHO-K1 Cricetulus griseus IC50 > 195000.0 nM PMID[507735]
NPT913 Cell Line CHO-K1 Cricetulus griseus IC50 = 73500.0 nM PMID[507735]
NPT1214 Individual Protein Acyl coenzyme A:cholesterol acyltransferase 1 Homo sapiens IC50 = 174900.0 nM PMID[507735]
NPT2584 Individual Protein Acyl coenzyme A:cholesterol acyltransferase 2 Homo sapiens IC50 = 187300.0 nM PMID[507735]
NPT1214 Individual Protein Acyl coenzyme A:cholesterol acyltransferase 1 Homo sapiens IC50 = 55100.0 nM PMID[507735]
NPT2584 Individual Protein Acyl coenzyme A:cholesterol acyltransferase 2 Homo sapiens IC50 = 100700.0 nM PMID[507735]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 100000.0 nM PMID[507733]
NPT2 Others Unspecified IC50 = 211000.0 nM PMID[507735]

☑ 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 NPC10636 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
0.8889 High Similarity NPC253604
0.8831 High Similarity NPC189206
0.8765 High Similarity NPC474693
0.8706 High Similarity NPC289479
0.8659 High Similarity NPC474694
0.8659 High Similarity NPC473659
0.8659 High Similarity NPC475860
0.8605 High Similarity NPC472303
0.8571 High Similarity NPC242448
0.8488 Intermediate Similarity NPC472811
0.8488 Intermediate Similarity NPC329842
0.8452 Intermediate Similarity NPC473891
0.8415 Intermediate Similarity NPC311070
0.8391 Intermediate Similarity NPC472812
0.8372 Intermediate Similarity NPC472642
0.8372 Intermediate Similarity NPC182136
0.8353 Intermediate Similarity NPC472809
0.8353 Intermediate Similarity NPC472810
0.8333 Intermediate Similarity NPC131813
0.8313 Intermediate Similarity NPC32223
0.8295 Intermediate Similarity NPC470255
0.8276 Intermediate Similarity NPC78594
0.8256 Intermediate Similarity NPC50488
0.8256 Intermediate Similarity NPC474396
0.8214 Intermediate Similarity NPC473251
0.8214 Intermediate Similarity NPC42586
0.8202 Intermediate Similarity NPC472441
0.8182 Intermediate Similarity NPC472641
0.8182 Intermediate Similarity NPC472640
0.8161 Intermediate Similarity NPC280149
0.8161 Intermediate Similarity NPC78973
0.8161 Intermediate Similarity NPC477782
0.8161 Intermediate Similarity NPC221111
0.8161 Intermediate Similarity NPC310479
0.8125 Intermediate Similarity NPC54996
0.8118 Intermediate Similarity NPC329692
0.8111 Intermediate Similarity NPC165632
0.8068 Intermediate Similarity NPC477783
0.8049 Intermediate Similarity NPC268827
0.8046 Intermediate Similarity NPC251528
0.8046 Intermediate Similarity NPC470734
0.8043 Intermediate Similarity NPC476767
0.8043 Intermediate Similarity NPC16601
0.8025 Intermediate Similarity NPC184737
0.8 Intermediate Similarity NPC30984
0.8 Intermediate Similarity NPC65661
0.8 Intermediate Similarity NPC106416
0.8 Intermediate Similarity NPC471915
0.8 Intermediate Similarity NPC86316
0.7978 Intermediate Similarity NPC152778
0.7978 Intermediate Similarity NPC139692
0.7978 Intermediate Similarity NPC205034
0.7978 Intermediate Similarity NPC162615
0.7978 Intermediate Similarity NPC53555
0.7976 Intermediate Similarity NPC30502
0.7976 Intermediate Similarity NPC321385
0.7976 Intermediate Similarity NPC476927
0.7952 Intermediate Similarity NPC170303
0.7935 Intermediate Similarity NPC474440
0.7912 Intermediate Similarity NPC134072
0.7912 Intermediate Similarity NPC234993
0.7912 Intermediate Similarity NPC473153
0.7912 Intermediate Similarity NPC242848
0.7907 Intermediate Similarity NPC471219
0.7907 Intermediate Similarity NPC474062
0.7901 Intermediate Similarity NPC132542
0.7889 Intermediate Similarity NPC57117
0.7889 Intermediate Similarity NPC469697
0.7882 Intermediate Similarity NPC471302
0.7882 Intermediate Similarity NPC96055
0.7872 Intermediate Similarity NPC471914
0.7865 Intermediate Similarity NPC72845
0.7865 Intermediate Similarity NPC472814
0.7865 Intermediate Similarity NPC177037
0.7849 Intermediate Similarity NPC472826
0.7849 Intermediate Similarity NPC472644
0.7849 Intermediate Similarity NPC324841
0.7831 Intermediate Similarity NPC281880
0.7826 Intermediate Similarity NPC475709
0.7791 Intermediate Similarity NPC474013
0.7789 Intermediate Similarity NPC471938
0.7778 Intermediate Similarity NPC7349
0.7766 Intermediate Similarity NPC472643
0.7765 Intermediate Similarity NPC42476
0.7765 Intermediate Similarity NPC472377
0.7753 Intermediate Similarity NPC232426
0.7753 Intermediate Similarity NPC51486
0.7753 Intermediate Similarity NPC281942
0.7742 Intermediate Similarity NPC473154
0.7738 Intermediate Similarity NPC40228
0.7738 Intermediate Similarity NPC159148
0.7727 Intermediate Similarity NPC474629
0.7727 Intermediate Similarity NPC472378
0.7717 Intermediate Similarity NPC162346
0.7717 Intermediate Similarity NPC16967
0.7708 Intermediate Similarity NPC471937
0.7692 Intermediate Similarity NPC105490
0.7692 Intermediate Similarity NPC191521
0.7692 Intermediate Similarity NPC104925
0.7692 Intermediate Similarity NPC298973
0.7692 Intermediate Similarity NPC324078
0.7684 Intermediate Similarity NPC476769
0.7684 Intermediate Similarity NPC472815
0.7684 Intermediate Similarity NPC121423
0.7683 Intermediate Similarity NPC61952
0.7674 Intermediate Similarity NPC306951
0.7674 Intermediate Similarity NPC471301
0.7667 Intermediate Similarity NPC141831
0.7667 Intermediate Similarity NPC477122
0.7647 Intermediate Similarity NPC471218
0.7647 Intermediate Similarity NPC2524
0.7647 Intermediate Similarity NPC200513
0.7647 Intermediate Similarity NPC256112
0.7647 Intermediate Similarity NPC471298
0.764 Intermediate Similarity NPC174342
0.764 Intermediate Similarity NPC5509
0.7634 Intermediate Similarity NPC477719
0.7634 Intermediate Similarity NPC477718
0.7634 Intermediate Similarity NPC205143
0.7634 Intermediate Similarity NPC476253
0.7634 Intermediate Similarity NPC474343
0.7614 Intermediate Similarity NPC166857
0.7614 Intermediate Similarity NPC312561
0.7609 Intermediate Similarity NPC276110
0.7609 Intermediate Similarity NPC111273
0.759 Intermediate Similarity NPC198240
0.7586 Intermediate Similarity NPC471795
0.7586 Intermediate Similarity NPC472442
0.7582 Intermediate Similarity NPC115021
0.7582 Intermediate Similarity NPC472871
0.7582 Intermediate Similarity NPC38232
0.7582 Intermediate Similarity NPC110022
0.7579 Intermediate Similarity NPC303559
0.7579 Intermediate Similarity NPC198992
0.7558 Intermediate Similarity NPC471297
0.7558 Intermediate Similarity NPC472440
0.7558 Intermediate Similarity NPC79945
0.7553 Intermediate Similarity NPC275086
0.7553 Intermediate Similarity NPC325229
0.7553 Intermediate Similarity NPC159763
0.7553 Intermediate Similarity NPC278386
0.7553 Intermediate Similarity NPC124512
0.7532 Intermediate Similarity NPC116013
0.7529 Intermediate Similarity NPC229584
0.7529 Intermediate Similarity NPC14203
0.7528 Intermediate Similarity NPC93411
0.7527 Intermediate Similarity NPC29952
0.7526 Intermediate Similarity NPC472819
0.75 Intermediate Similarity NPC58329
0.75 Intermediate Similarity NPC474555
0.75 Intermediate Similarity NPC170394
0.75 Intermediate Similarity NPC475038
0.75 Intermediate Similarity NPC109195
0.75 Intermediate Similarity NPC242767
0.75 Intermediate Similarity NPC474554
0.7475 Intermediate Similarity NPC476765
0.7475 Intermediate Similarity NPC181994
0.7474 Intermediate Similarity NPC38855
0.7474 Intermediate Similarity NPC471413
0.7474 Intermediate Similarity NPC201406
0.7474 Intermediate Similarity NPC477716
0.7474 Intermediate Similarity NPC477720
0.7474 Intermediate Similarity NPC117685
0.7474 Intermediate Similarity NPC477721
0.7474 Intermediate Similarity NPC251680
0.7471 Intermediate Similarity NPC102048
0.7471 Intermediate Similarity NPC30486
0.747 Intermediate Similarity NPC316500
0.747 Intermediate Similarity NPC97377
0.747 Intermediate Similarity NPC473756
0.7449 Intermediate Similarity NPC472818
0.7447 Intermediate Similarity NPC231751
0.7447 Intermediate Similarity NPC253826
0.7447 Intermediate Similarity NPC73911
0.7447 Intermediate Similarity NPC51499
0.7447 Intermediate Similarity NPC476768
0.7444 Intermediate Similarity NPC262858
0.7444 Intermediate Similarity NPC472240
0.7444 Intermediate Similarity NPC82876
0.7423 Intermediate Similarity NPC45897
0.7423 Intermediate Similarity NPC120009
0.7423 Intermediate Similarity NPC281378
0.7423 Intermediate Similarity NPC471208
0.7419 Intermediate Similarity NPC183012
0.7419 Intermediate Similarity NPC209355
0.7416 Intermediate Similarity NPC231599
0.7416 Intermediate Similarity NPC475678
0.7416 Intermediate Similarity NPC181103
0.7416 Intermediate Similarity NPC471796
0.7412 Intermediate Similarity NPC469802
0.7396 Intermediate Similarity NPC477717
0.7396 Intermediate Similarity NPC471412
0.7391 Intermediate Similarity NPC156553
0.7391 Intermediate Similarity NPC166346
0.7386 Intermediate Similarity NPC146850
0.7386 Intermediate Similarity NPC329630
0.7386 Intermediate Similarity NPC147921
0.7386 Intermediate Similarity NPC189311
0.7386 Intermediate Similarity NPC52628
0.7386 Intermediate Similarity NPC287015

  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 NPC10636 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
0.7647 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7553 Intermediate Similarity NPD4225 Approved
0.7474 Intermediate Similarity NPD7639 Approved
0.7474 Intermediate Similarity NPD7640 Approved
0.7368 Intermediate Similarity NPD7638 Approved
0.7273 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1694 Approved
0.697 Remote Similarity NPD7632 Discontinued
0.6961 Remote Similarity NPD6686 Approved
0.6771 Remote Similarity NPD7748 Approved
0.6739 Remote Similarity NPD4519 Discontinued
0.6739 Remote Similarity NPD4623 Approved
0.6737 Remote Similarity NPD5693 Phase 1
0.6667 Remote Similarity NPD3573 Approved
0.6571 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6566 Remote Similarity NPD7902 Approved
0.6562 Remote Similarity NPD7637 Suspended
0.6562 Remote Similarity NPD7515 Phase 2
0.6559 Remote Similarity NPD3618 Phase 1
0.6559 Remote Similarity NPD7521 Approved
0.6559 Remote Similarity NPD7334 Approved
0.6559 Remote Similarity NPD5330 Approved
0.6559 Remote Similarity NPD6409 Approved
0.6559 Remote Similarity NPD7146 Approved
0.6559 Remote Similarity NPD6684 Approved
0.6545 Remote Similarity NPD7328 Approved
0.6545 Remote Similarity NPD7327 Approved
0.6526 Remote Similarity NPD6051 Approved
0.6517 Remote Similarity NPD4195 Approved
0.6509 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6495 Remote Similarity NPD6399 Phase 3
0.6486 Remote Similarity NPD7516 Approved
0.6484 Remote Similarity NPD4221 Approved
0.6484 Remote Similarity NPD4223 Phase 3
0.6455 Remote Similarity NPD7115 Discovery
0.6444 Remote Similarity NPD4695 Discontinued
0.6429 Remote Similarity NPD8294 Approved
0.6429 Remote Similarity NPD8377 Approved
0.6421 Remote Similarity NPD6672 Approved
0.6421 Remote Similarity NPD5737 Approved
0.6421 Remote Similarity NPD6903 Approved
0.6421 Remote Similarity NPD5208 Approved
0.6421 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6404 Remote Similarity NPD3617 Approved
0.64 Remote Similarity NPD6083 Phase 2
0.64 Remote Similarity NPD6084 Phase 2
0.6375 Remote Similarity NPD4192 Approved
0.6375 Remote Similarity NPD4193 Approved
0.6375 Remote Similarity NPD4191 Approved
0.6375 Remote Similarity NPD4194 Approved
0.6373 Remote Similarity NPD5344 Discontinued
0.6372 Remote Similarity NPD8296 Approved
0.6372 Remote Similarity NPD8379 Approved
0.6372 Remote Similarity NPD8378 Approved
0.6372 Remote Similarity NPD8335 Approved
0.6372 Remote Similarity NPD8033 Approved
0.6372 Remote Similarity NPD8380 Approved
0.6364 Remote Similarity NPD5695 Phase 3
0.6354 Remote Similarity NPD6673 Approved
0.6354 Remote Similarity NPD5328 Approved
0.6354 Remote Similarity NPD6080 Approved
0.6354 Remote Similarity NPD6904 Approved
0.6344 Remote Similarity NPD3666 Approved
0.6344 Remote Similarity NPD4197 Approved
0.6344 Remote Similarity NPD3665 Phase 1
0.6344 Remote Similarity NPD3133 Approved
0.6341 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6337 Remote Similarity NPD5696 Approved
0.6304 Remote Similarity NPD3667 Approved
0.6293 Remote Similarity NPD7507 Approved
0.6289 Remote Similarity NPD5785 Approved
0.6286 Remote Similarity NPD5739 Approved
0.6286 Remote Similarity NPD6675 Approved
0.6286 Remote Similarity NPD7128 Approved
0.6286 Remote Similarity NPD6402 Approved
0.6277 Remote Similarity NPD5329 Approved
0.6277 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6275 Remote Similarity NPD6648 Approved
0.6263 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6263 Remote Similarity NPD6001 Approved
0.6263 Remote Similarity NPD7900 Approved
0.625 Remote Similarity NPD8039 Approved
0.6239 Remote Similarity NPD6882 Approved
0.6237 Remote Similarity NPD6695 Phase 3
0.6226 Remote Similarity NPD5701 Approved
0.6226 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6226 Remote Similarity NPD5697 Approved
0.6224 Remote Similarity NPD8035 Phase 2
0.6224 Remote Similarity NPD6079 Approved
0.6224 Remote Similarity NPD5284 Approved
0.6224 Remote Similarity NPD8034 Phase 2
0.6224 Remote Similarity NPD5281 Approved
0.6211 Remote Similarity NPD6098 Approved
0.6211 Remote Similarity NPD4689 Approved
0.6211 Remote Similarity NPD4138 Approved
0.6211 Remote Similarity NPD4688 Approved
0.6211 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6211 Remote Similarity NPD4693 Phase 3
0.6211 Remote Similarity NPD5205 Approved
0.6211 Remote Similarity NPD4690 Approved
0.62 Remote Similarity NPD1698 Clinical (unspecified phase)
0.62 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6186 Remote Similarity NPD7285 Clinical (unspecified phase)
0.618 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6176 Remote Similarity NPD8029 Clinical (unspecified phase)
0.617 Remote Similarity NPD4786 Approved
0.617 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6168 Remote Similarity NPD7320 Approved
0.6168 Remote Similarity NPD6899 Approved
0.6168 Remote Similarity NPD6011 Approved
0.6168 Remote Similarity NPD6881 Approved
0.6162 Remote Similarity NPD5778 Approved
0.6162 Remote Similarity NPD5779 Approved
0.6162 Remote Similarity NPD4202 Approved
0.6154 Remote Similarity NPD7645 Phase 2
0.6154 Remote Similarity NPD6929 Approved
0.6136 Remote Similarity NPD6924 Approved
0.6136 Remote Similarity NPD6926 Approved
0.6134 Remote Similarity NPD7319 Approved
0.6129 Remote Similarity NPD5209 Approved
0.6122 Remote Similarity NPD5692 Phase 3
0.6122 Remote Similarity NPD5207 Approved
0.6117 Remote Similarity NPD6404 Discontinued
0.6111 Remote Similarity NPD6372 Approved
0.6111 Remote Similarity NPD6014 Approved
0.6111 Remote Similarity NPD6013 Approved
0.6111 Remote Similarity NPD6373 Approved
0.6111 Remote Similarity NPD6012 Approved
0.6105 Remote Similarity NPD1696 Phase 3
0.6105 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6092 Remote Similarity NPD4243 Approved
0.6087 Remote Similarity NPD7525 Registered
0.6087 Remote Similarity NPD6931 Approved
0.6087 Remote Similarity NPD7503 Approved
0.6087 Remote Similarity NPD6930 Phase 2
0.6067 Remote Similarity NPD7339 Approved
0.6067 Remote Similarity NPD8264 Approved
0.6067 Remote Similarity NPD6942 Approved
0.6061 Remote Similarity NPD5694 Approved
0.6061 Remote Similarity NPD6050 Approved
0.6061 Remote Similarity NPD6411 Approved
0.6055 Remote Similarity NPD7290 Approved
0.6055 Remote Similarity NPD6883 Approved
0.6055 Remote Similarity NPD7102 Approved
0.6044 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6044 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6042 Remote Similarity NPD4694 Approved
0.6042 Remote Similarity NPD5690 Phase 2
0.6042 Remote Similarity NPD5280 Approved
0.6042 Remote Similarity NPD5279 Phase 3
0.6024 Remote Similarity NPD5325 Clinical (unspecified phase)
0.602 Remote Similarity NPD4753 Phase 2
0.6 Remote Similarity NPD6869 Approved
0.6 Remote Similarity NPD5211 Phase 2
0.6 Remote Similarity NPD8130 Phase 1
0.6 Remote Similarity NPD6617 Approved
0.6 Remote Similarity NPD6650 Approved
0.6 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6 Remote Similarity NPD6933 Approved
0.6 Remote Similarity NPD6649 Approved
0.6 Remote Similarity NPD6847 Approved
0.598 Remote Similarity NPD5220 Clinical (unspecified phase)
0.598 Remote Similarity NPD4697 Phase 3
0.598 Remote Similarity NPD5221 Approved
0.598 Remote Similarity NPD5222 Approved
0.5979 Remote Similarity NPD7750 Discontinued
0.5979 Remote Similarity NPD7524 Approved
0.5979 Remote Similarity NPD4751 Clinical (unspecified phase)
0.596 Remote Similarity NPD7838 Discovery
0.596 Remote Similarity NPD6698 Approved
0.596 Remote Similarity NPD46 Approved
0.5955 Remote Similarity NPD4785 Approved
0.5955 Remote Similarity NPD4784 Approved
0.5946 Remote Similarity NPD8297 Approved
0.5934 Remote Similarity NPD5776 Phase 2
0.5934 Remote Similarity NPD6925 Approved
0.5926 Remote Similarity NPD6412 Phase 2
0.5922 Remote Similarity NPD4755 Approved
0.5922 Remote Similarity NPD5173 Approved
0.5914 Remote Similarity NPD7509 Discontinued
0.5914 Remote Similarity NPD7332 Phase 2
0.5914 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5914 Remote Similarity NPD7514 Phase 3
0.5909 Remote Similarity NPD7151 Approved
0.5909 Remote Similarity NPD7150 Approved
0.5909 Remote Similarity NPD7152 Approved
0.5895 Remote Similarity NPD7154 Phase 3
0.5895 Remote Similarity NPD5362 Discontinued
0.5893 Remote Similarity NPD8133 Approved
0.5889 Remote Similarity NPD5275 Approved
0.5889 Remote Similarity NPD4190 Phase 3
0.5888 Remote Similarity NPD5141 Approved
0.5888 Remote Similarity NPD5909 Discontinued
0.5877 Remote Similarity NPD6009 Approved
0.587 Remote Similarity NPD7145 Approved
0.5862 Remote Similarity NPD6923 Approved
0.5862 Remote Similarity NPD4137 Phase 3
0.5862 Remote Similarity NPD6922 Approved
0.5859 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5859 Remote Similarity NPD6101 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