Natural Product: NPC469538

Natural Product ID:  NPC469538
Common Name:   Caespitenone
IUPAC Name:   (2S)-2-[(1R,3R,4R)-3-bromo-4-chloro-4-methylcyclohexyl]-2,6,6-trimethylpyran-3-one
Synonyms:  
Molecular Formula:   C15H22BrClO2
Standard InCHIKey:  PXPRNVNJRBIVSF-FKGLVLAHSA-N
Standard InCHI:  InChI=1S/C15H22BrClO2/c1-13(2)7-6-12(18)15(4,19-13)10-5-8-14(3,17)11(16)9-10/h6-7,10-11H,5,8-9H2,1-4H3/t10-,11-,14-,15+/m1/s1
Canonical SMILES:  Br[C@@H]1C[C@@H](CC[C@@]1(C)Cl)[C@]1(C)OC(C)(C)C=CC1=O
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO29486 Laurencia catarinensis Species Rhodomelaceae Eukaryota Brazil PMID[20039643]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT83 Cell Line MCF7 Homo sapiens IC50 = 19700 nM 17548494
NPT762 Cell Line A-431 Homo sapiens IC50 = 21600 nM 1336040
NPT139 Cell Line HT-29 Homo sapiens IC50 = 18900 nM 1336040

  Similar Natural Products 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 NPC469538 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
0.7083 Intermediate Similarity NPC469570
0.7083 Intermediate Similarity NPC48210
0.6939 Remote Similarity NPC280810
0.6907 Remote Similarity NPC33663
0.6667 Remote Similarity NPC134083
0.6604 Remote Similarity NPC166770
0.6569 Remote Similarity NPC224270
0.6566 Remote Similarity NPC96621
0.6542 Remote Similarity NPC185253
0.6542 Remote Similarity NPC215253
0.6535 Remote Similarity NPC241507
0.6514 Remote Similarity NPC473144
0.6514 Remote Similarity NPC297281
0.6495 Remote Similarity NPC474353
0.6471 Remote Similarity NPC329643
0.6436 Remote Similarity NPC109900
0.6421 Remote Similarity NPC180290
0.64 Remote Similarity NPC177932
0.64 Remote Similarity NPC137493
0.6373 Remote Similarity NPC478259
0.6373 Remote Similarity NPC478261
0.6373 Remote Similarity NPC478260
0.6364 Remote Similarity NPC288281
0.6346 Remote Similarity NPC303697
0.6337 Remote Similarity NPC472863
0.6327 Remote Similarity NPC474085
0.6321 Remote Similarity NPC474602
0.6321 Remote Similarity NPC12727
0.6316 Remote Similarity NPC40353
0.6311 Remote Similarity NPC285982
0.63 Remote Similarity NPC30486
0.63 Remote Similarity NPC60951
0.6286 Remote Similarity NPC242637
0.6263 Remote Similarity NPC186276
0.625 Remote Similarity NPC280592
0.625 Remote Similarity NPC213636
0.625 Remote Similarity NPC476608
0.625 Remote Similarity NPC253177
0.625 Remote Similarity NPC223093
0.6238 Remote Similarity NPC133652
0.6238 Remote Similarity NPC189311
0.6226 Remote Similarity NPC143210
0.6214 Remote Similarity NPC215831
0.62 Remote Similarity NPC474703
0.62 Remote Similarity NPC22611
0.62 Remote Similarity NPC222358
0.619 Remote Similarity NPC471329
0.619 Remote Similarity NPC166110
0.619 Remote Similarity NPC32944
0.619 Remote Similarity NPC193396
0.619 Remote Similarity NPC296114
0.6168 Remote Similarity NPC295347
0.6154 Remote Similarity NPC173042
0.6154 Remote Similarity NPC280833
0.6154 Remote Similarity NPC73995
0.6154 Remote Similarity NPC284561
0.6146 Remote Similarity NPC472305
0.6139 Remote Similarity NPC282598
0.6134 Remote Similarity NPC243298
0.6132 Remote Similarity NPC229976
0.6132 Remote Similarity NPC248193
0.6122 Remote Similarity NPC469617
0.6111 Remote Similarity NPC94337
0.61 Remote Similarity NPC221231
0.61 Remote Similarity NPC471326
0.6095 Remote Similarity NPC38952
0.6092 Remote Similarity NPC308569
0.6092 Remote Similarity NPC469572
0.6092 Remote Similarity NPC469582
0.6091 Remote Similarity NPC472012
0.6082 Remote Similarity NPC34110
0.6078 Remote Similarity NPC132228
0.6078 Remote Similarity NPC241512
0.6078 Remote Similarity NPC476678
0.6078 Remote Similarity NPC8518
0.6078 Remote Similarity NPC263997
0.6078 Remote Similarity NPC6185
0.6078 Remote Similarity NPC469993
0.6075 Remote Similarity NPC38830
0.6071 Remote Similarity NPC25666
0.6071 Remote Similarity NPC271059
0.6061 Remote Similarity NPC47747
0.6061 Remote Similarity NPC108955
0.6055 Remote Similarity NPC38530
0.6055 Remote Similarity NPC84335
0.6055 Remote Similarity NPC208094
0.6042 Remote Similarity NPC244166
0.604 Remote Similarity NPC193198
0.604 Remote Similarity NPC53867
0.6038 Remote Similarity NPC26865
0.6038 Remote Similarity NPC45579
0.6038 Remote Similarity NPC190442
0.6036 Remote Similarity NPC207885
0.6033 Remote Similarity NPC245320
0.6022 Remote Similarity NPC265574
0.602 Remote Similarity NPC275494
0.602 Remote Similarity NPC207772
0.602 Remote Similarity NPC471409
0.6019 Remote Similarity NPC127197
0.6019 Remote Similarity NPC279859
0.6019 Remote Similarity NPC234038
0.6019 Remote Similarity NPC33473
0.6019 Remote Similarity NPC470974
0.6019 Remote Similarity NPC220478
0.6019 Remote Similarity NPC470978
0.6019 Remote Similarity NPC38576
0.6018 Remote Similarity NPC272528
0.6 Remote Similarity NPC316598
0.6 Remote Similarity NPC5509
0.6 Remote Similarity NPC282293
0.6 Remote Similarity NPC264378
0.6 Remote Similarity NPC142159
0.6 Remote Similarity NPC95364
0.6 Remote Similarity NPC325031
0.6 Remote Similarity NPC55869
0.5984 Remote Similarity NPC476815
0.5984 Remote Similarity NPC473145
0.5984 Remote Similarity NPC31641
0.598 Remote Similarity NPC196487
0.598 Remote Similarity NPC469569
0.598 Remote Similarity NPC14575
0.598 Remote Similarity NPC474359
0.5979 Remote Similarity NPC7629
0.5979 Remote Similarity NPC151622
0.5979 Remote Similarity NPC186554
0.5979 Remote Similarity NPC30575
0.5979 Remote Similarity NPC198473
0.5979 Remote Similarity NPC76966
0.5979 Remote Similarity NPC473223
0.5962 Remote Similarity NPC181327
0.5962 Remote Similarity NPC477228
0.596 Remote Similarity NPC150646
0.5946 Remote Similarity NPC469551
0.5943 Remote Similarity NPC152467
0.5943 Remote Similarity NPC474209
0.5943 Remote Similarity NPC212369
0.5943 Remote Similarity NPC469372
0.5943 Remote Similarity NPC212679
0.5943 Remote Similarity NPC113393
0.5943 Remote Similarity NPC475823
0.5943 Remote Similarity NPC469595
0.5943 Remote Similarity NPC220454
0.5943 Remote Similarity NPC471818
0.5941 Remote Similarity NPC200513
0.5926 Remote Similarity NPC477129
0.5926 Remote Similarity NPC148463
0.5926 Remote Similarity NPC477130
0.5926 Remote Similarity NPC470697
0.5926 Remote Similarity NPC476596
0.5922 Remote Similarity NPC474680
0.5918 Remote Similarity NPC283087
0.5918 Remote Similarity NPC187568
0.5918 Remote Similarity NPC316500
0.5918 Remote Similarity NPC257666
0.5918 Remote Similarity NPC266193
0.5918 Remote Similarity NPC53581
0.5918 Remote Similarity NPC316324
0.5918 Remote Similarity NPC65603
0.5918 Remote Similarity NPC103987
0.5918 Remote Similarity NPC41780
0.5913 Remote Similarity NPC475294
0.5909 Remote Similarity NPC151488
0.5909 Remote Similarity NPC471916
0.5905 Remote Similarity NPC471047
0.5905 Remote Similarity NPC475906
0.5905 Remote Similarity NPC226863
0.5905 Remote Similarity NPC475902
0.5905 Remote Similarity NPC469628
0.5905 Remote Similarity NPC469631
0.5905 Remote Similarity NPC307298
0.5905 Remote Similarity NPC469653
0.5905 Remote Similarity NPC58271
0.59 Remote Similarity NPC304795
0.59 Remote Similarity NPC195424
0.59 Remote Similarity NPC472301
0.59 Remote Similarity NPC469637
0.59 Remote Similarity NPC476809
0.5893 Remote Similarity NPC310981
0.5893 Remote Similarity NPC469851
0.5893 Remote Similarity NPC112613
0.5893 Remote Similarity NPC224172
0.5888 Remote Similarity NPC219874
0.5888 Remote Similarity NPC252433
0.5882 Remote Similarity NPC105803
0.5882 Remote Similarity NPC297398
0.5882 Remote Similarity NPC39588
0.5882 Remote Similarity NPC118423
0.5877 Remote Similarity NPC133921
0.5872 Remote Similarity NPC171395
0.5872 Remote Similarity NPC209355
0.587 Remote Similarity NPC197089
0.5865 Remote Similarity NPC203795
0.5865 Remote Similarity NPC261721
0.5859 Remote Similarity NPC231739
0.5859 Remote Similarity NPC222210
0.5859 Remote Similarity NPC63445
0.5859 Remote Similarity NPC23778
0.5859 Remote Similarity NPC128276
0.5859 Remote Similarity NPC19443
0.5856 Remote Similarity NPC98868

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC469538 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
0.64 Remote Similarity NPD1694 Approved
0.6321 Remote Similarity NPD5654 Approved
0.6204 Remote Similarity NPD5959 Approved
0.619 Remote Similarity NPD5693 Phase 1
0.6053 Remote Similarity NPD6614 Approved
0.5981 Remote Similarity NPD5133 Approved
0.5941 Remote Similarity NPD4752 Clinical (unspecified phase)
0.59 Remote Similarity NPD4695 Discontinued
0.5888 Remote Similarity NPD5694 Approved
0.5865 Remote Similarity NPD5690 Phase 2
0.5849 Remote Similarity NPD6673 Approved
0.5849 Remote Similarity NPD6904 Approved
0.5849 Remote Similarity NPD6080 Approved
0.5841 Remote Similarity NPD5091 Approved
0.581 Remote Similarity NPD3573 Approved
0.5794 Remote Similarity NPD5692 Phase 3
0.5755 Remote Similarity NPD5737 Approved
0.5755 Remote Similarity NPD6672 Approved
0.5741 Remote Similarity NPD6050 Approved
0.5714 Remote Similarity NPD4519 Discontinued
0.5714 Remote Similarity NPD6098 Approved
0.5714 Remote Similarity NPD4623 Approved
0.5699 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5673 Remote Similarity NPD4197 Approved
0.5656 Remote Similarity NPD6868 Approved
0.5645 Remote Similarity NPD7100 Approved
0.5645 Remote Similarity NPD7101 Approved
0.5619 Remote Similarity NPD5329 Approved

Structure

External Identifiers

PubChem CID   46881080
ChEMBL   CHEMBL1086596
ZINC  

Physicochemical Properties

Molecular Weight:  348.05
ALogP:  2.8899
MLogP:  2.67
XLogP:  3.687
# Rotatable Bonds:  7
Polar Surface Area:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  19

Download Data

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Structure MOL file  
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Biological Activities  
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