Natural Product: NPC469526

Natural Product ID:  NPC469526
Common Name:   (E)-3,2',4'-Trihydroxy-3'-Methoxychalcone
IUPAC Name:   (E)-3-(3-hydroxyphenyl)-1-(2,3,4-trihydroxyphenyl)prop-2-en-1-one
Synonyms:  
Molecular Formula:   C15H12O5
Standard InCHIKey:  GADGMUTUOCVUJQ-GQCTYLIASA-N
Standard InCHI:  InChI=1S/C15H12O5/c16-10-3-1-2-9(8-10)4-6-12(17)11-5-7-13(18)15(20)14(11)19/h1-8,16,18-20H/b6-4+
Canonical SMILES:  Oc1cccc(c1)/C=C/C(=O)c1ccc(c(c1O)O)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
NPO26507 Galenia africana Species Aizoaceae Eukaryota Leaves PMID[20035557]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis Inhibition = 99.5 % 17488128
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 174800 nM 20951582
NPT466 Cell Line U-937 Homo sapiens IC50 = 333200 nM 23738539
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 104800 nM 23558238
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MBC = 183.7 nM 23558238

  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 NPC469526 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 NPC34070
0.992 High Similarity NPC135801
0.9919 High Similarity NPC26697
0.976 High Similarity NPC233056
0.952 High Similarity NPC107672
0.9462 High Similarity NPC264112
0.9462 High Similarity NPC194764
0.9462 High Similarity NPC65005
0.9449 High Similarity NPC244441
0.944 High Similarity NPC8745
0.9435 High Similarity NPC13238
0.9389 High Similarity NPC290030
0.936 High Similarity NPC10926
0.9323 High Similarity NPC203063
0.9318 High Similarity NPC175552
0.9248 High Similarity NPC472903
0.9194 High Similarity NPC19174
0.9194 High Similarity NPC73532
0.9194 High Similarity NPC143427
0.9194 High Similarity NPC267552
0.9194 High Similarity NPC115159
0.9194 High Similarity NPC224273
0.9194 High Similarity NPC45438
0.912 High Similarity NPC32032
0.912 High Similarity NPC133909
0.9118 High Similarity NPC287722
0.9118 High Similarity NPC238629
0.9113 High Similarity NPC297186
0.9111 High Similarity NPC472904
0.9098 High Similarity NPC170742
0.9062 High Similarity NPC214620
0.9051 High Similarity NPC142165
0.9044 High Similarity NPC284556
0.9044 High Similarity NPC301178
0.904 High Similarity NPC156139
0.904 High Similarity NPC242895
0.9023 High Similarity NPC223836
0.8978 High Similarity NPC254659
0.8978 High Similarity NPC471417
0.896 High Similarity NPC248363
0.8952 High Similarity NPC158222
0.8947 High Similarity NPC72918
0.8915 High Similarity NPC156539
0.8913 High Similarity NPC38065
0.8913 High Similarity NPC242893
0.888 High Similarity NPC159525
0.8872 High Similarity NPC282780
0.8872 High Similarity NPC166480
0.8872 High Similarity NPC44437
0.8857 High Similarity NPC125449
0.8857 High Similarity NPC188074
0.8857 High Similarity NPC168803
0.8849 High Similarity NPC70136
0.8806 High Similarity NPC129752
0.88 High Similarity NPC161617
0.8797 High Similarity NPC294226
0.8794 High Similarity NPC287395
0.8794 High Similarity NPC43669
0.8794 High Similarity NPC183655
0.8794 High Similarity NPC12367
0.8794 High Similarity NPC272721
0.8794 High Similarity NPC196277
0.8794 High Similarity NPC218490
0.8794 High Similarity NPC118726
0.8779 High Similarity NPC109123
0.8779 High Similarity NPC92624
0.8779 High Similarity NPC474998
0.8777 High Similarity NPC279121
0.8769 High Similarity NPC105157
0.8769 High Similarity NPC162612
0.8769 High Similarity NPC190043
0.8769 High Similarity NPC266689
0.8769 High Similarity NPC98254
0.8769 High Similarity NPC169250
0.8769 High Similarity NPC103356
0.8769 High Similarity NPC23126
0.8769 High Similarity NPC100067
0.8769 High Similarity NPC72158
0.8769 High Similarity NPC30501
0.8768 High Similarity NPC312256
0.8759 High Similarity NPC50823
0.875 High Similarity NPC416
0.875 High Similarity NPC61398
0.874 High Similarity NPC196976
0.8732 High Similarity NPC69430
0.8732 High Similarity NPC92722
0.8732 High Similarity NPC40290
0.8732 High Similarity NPC139293
0.8732 High Similarity NPC333691
0.8732 High Similarity NPC142876
0.8732 High Similarity NPC200060
0.8732 High Similarity NPC264550
0.8732 High Similarity NPC264289
0.8732 High Similarity NPC195763
0.8732 High Similarity NPC102003
0.8723 High Similarity NPC77378
0.8723 High Similarity NPC140840
0.8723 High Similarity NPC86847
0.8723 High Similarity NPC275772
0.8723 High Similarity NPC239312
0.8723 High Similarity NPC74881
0.8723 High Similarity NPC51443
0.8723 High Similarity NPC130230
0.8723 High Similarity NPC95864
0.872 High Similarity NPC40649
0.872 High Similarity NPC209486
0.8712 High Similarity NPC259942
0.8712 High Similarity NPC117609
0.8712 High Similarity NPC147757
0.8705 High Similarity NPC175013
0.8705 High Similarity NPC119663
0.8702 High Similarity NPC21305
0.8702 High Similarity NPC179898
0.8702 High Similarity NPC221777
0.8702 High Similarity NPC473017
0.8696 High Similarity NPC110419
0.8692 High Similarity NPC62952
0.8692 High Similarity NPC267846
0.8676 High Similarity NPC147418
0.8676 High Similarity NPC53206
0.8676 High Similarity NPC53414
0.8672 High Similarity NPC225710
0.8671 High Similarity NPC472279
0.8671 High Similarity NPC10467
0.8671 High Similarity NPC45873
0.8671 High Similarity NPC260582
0.8671 High Similarity NPC29231
0.8662 High Similarity NPC254702
0.8662 High Similarity NPC19545
0.8662 High Similarity NPC80710
0.8662 High Similarity NPC15329
0.8662 High Similarity NPC276930
0.8662 High Similarity NPC131451
0.8662 High Similarity NPC194856
0.8662 High Similarity NPC194653
0.8662 High Similarity NPC471907
0.8662 High Similarity NPC139364
0.8662 High Similarity NPC203747
0.8661 High Similarity NPC146642
0.8652 High Similarity NPC20791
0.8652 High Similarity NPC179271
0.8643 High Similarity NPC105213
0.8643 High Similarity NPC257025
0.8643 High Similarity NPC207732
0.864 High Similarity NPC150919
0.8636 High Similarity NPC120488
0.8636 High Similarity NPC102829
0.8633 High Similarity NPC291078
0.8626 High Similarity NPC116513
0.8613 High Similarity NPC123714
0.8611 High Similarity NPC31363
0.8611 High Similarity NPC227485
0.8611 High Similarity NPC251110
0.8603 High Similarity NPC254847
0.8601 High Similarity NPC216318
0.8601 High Similarity NPC183959
0.8601 High Similarity NPC105512
0.8601 High Similarity NPC17286
0.8601 High Similarity NPC1612
0.8601 High Similarity NPC296197
0.8601 High Similarity NPC195351
0.8601 High Similarity NPC259713
0.8601 High Similarity NPC38545
0.8601 High Similarity NPC171916
0.8592 High Similarity NPC108406
0.8592 High Similarity NPC93034
0.8592 High Similarity NPC207729
0.8592 High Similarity NPC119660
0.8583 High Similarity NPC294037
0.8582 High Similarity NPC17843
0.8582 High Similarity NPC478190
0.8561 High Similarity NPC247250
0.8561 High Similarity NPC767
0.8552 High Similarity NPC35763
0.8552 High Similarity NPC245382
0.8552 High Similarity NPC60972
0.8552 High Similarity NPC100263
0.8552 High Similarity NPC257648
0.8552 High Similarity NPC291802
0.8552 High Similarity NPC100971
0.8552 High Similarity NPC269451
0.8552 High Similarity NPC477231
0.8552 High Similarity NPC121522
0.8552 High Similarity NPC149889
0.8552 High Similarity NPC181209
0.8552 High Similarity NPC312338
0.8552 High Similarity NPC39732
0.8552 High Similarity NPC209487
0.8552 High Similarity NPC131266
0.8552 High Similarity NPC216769
0.8551 High Similarity NPC471819
0.8551 High Similarity NPC242994
0.8551 High Similarity NPC138099
0.8542 High Similarity NPC62042
0.8542 High Similarity NPC248102
0.8542 High Similarity NPC85131
0.8542 High Similarity NPC77858
0.8542 High Similarity NPC184136
0.8542 High Similarity NPC61620
0.854 High Similarity NPC471905

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC469526 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
0.992 High Similarity NPD943 Approved
0.9167 High Similarity NPD651 Clinical (unspecified phase)
0.8777 High Similarity NPD1511 Approved
0.8672 High Similarity NPD9269 Phase 2
0.8652 High Similarity NPD1512 Approved
0.8603 High Similarity NPD1509 Clinical (unspecified phase)
0.8378 Intermediate Similarity NPD3882 Suspended
0.8367 Intermediate Similarity NPD2801 Approved
0.8359 Intermediate Similarity NPD9268 Approved
0.8333 Intermediate Similarity NPD1510 Phase 2
0.8309 Intermediate Similarity NPD1240 Approved
0.8299 Intermediate Similarity NPD1934 Approved
0.8248 Intermediate Similarity NPD230 Phase 1
0.8243 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8195 Intermediate Similarity NPD1470 Approved
0.8188 Intermediate Similarity NPD1607 Approved
0.803 Intermediate Similarity NPD1201 Approved
0.8028 Intermediate Similarity NPD1549 Phase 2
0.7984 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7958 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7958 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD3818 Discontinued
0.7877 Intermediate Similarity NPD7390 Discontinued
0.78 Intermediate Similarity NPD4380 Phase 2
0.7794 Intermediate Similarity NPD1164 Approved
0.7778 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD6166 Phase 2
0.7771 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7712 Intermediate Similarity NPD3817 Phase 2
0.7703 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD1465 Phase 2
0.7643 Intermediate Similarity NPD6232 Discontinued
0.7639 Intermediate Similarity NPD5405 Approved
0.7639 Intermediate Similarity NPD5406 Approved
0.7639 Intermediate Similarity NPD5404 Approved
0.7639 Intermediate Similarity NPD5408 Approved
0.7638 Intermediate Similarity NPD9266 Approved
0.7638 Intermediate Similarity NPD74 Approved
0.7635 Intermediate Similarity NPD6799 Approved
0.7625 Intermediate Similarity NPD7054 Approved
0.761 Intermediate Similarity NPD7473 Discontinued
0.7584 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD7472 Approved
0.7578 Intermediate Similarity NPD7074 Phase 3
0.7559 Intermediate Similarity NPD9264 Approved
0.7559 Intermediate Similarity NPD9263 Approved
0.7559 Intermediate Similarity NPD9267 Approved
0.7559 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD9494 Approved
0.7546 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD6797 Phase 2
0.7517 Intermediate Similarity NPD1551 Phase 2
0.7517 Intermediate Similarity NPD2796 Approved
0.7517 Intermediate Similarity NPD2935 Discontinued
0.75 Intermediate Similarity NPD7075 Discontinued
0.75 Intermediate Similarity NPD6190 Approved
0.75 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1242 Phase 1
0.7485 Intermediate Similarity NPD7251 Discontinued
0.7483 Intermediate Similarity NPD447 Suspended
0.7444 Intermediate Similarity NPD9493 Approved
0.7432 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD3750 Approved
0.7419 Intermediate Similarity NPD7819 Suspended
0.7419 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD1203 Approved
0.7405 Intermediate Similarity NPD5494 Approved
0.7389 Intermediate Similarity NPD3749 Approved
0.7376 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD2344 Approved
0.7338 Intermediate Similarity NPD6599 Discontinued
0.7333 Intermediate Similarity NPD7808 Phase 3
0.7317 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD3021 Approved
0.7308 Intermediate Similarity NPD3022 Approved
0.7305 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD9281 Approved
0.729 Intermediate Similarity NPD7411 Suspended
0.7267 Intermediate Similarity NPD3926 Phase 2
0.7266 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD5402 Approved
0.7255 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD1247 Approved
0.7248 Intermediate Similarity NPD2800 Approved
0.7244 Intermediate Similarity NPD6801 Discontinued
0.7244 Intermediate Similarity NPD9261 Approved
0.7233 Intermediate Similarity NPD919 Approved
0.7219 Intermediate Similarity NPD3300 Phase 2
0.7206 Intermediate Similarity NPD9545 Approved
0.7172 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD1613 Approved
0.7165 Intermediate Similarity NPD940 Approved
0.7165 Intermediate Similarity NPD846 Approved
0.7153 Intermediate Similarity NPD3764 Approved
0.7153 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD2309 Approved
0.7143 Intermediate Similarity NPD5403 Approved
0.7133 Intermediate Similarity NPD1243 Approved
0.7124 Intermediate Similarity NPD2532 Approved
0.7124 Intermediate Similarity NPD2534 Approved
0.7124 Intermediate Similarity NPD2533 Approved
0.7124 Intermediate Similarity NPD5401 Approved
0.7095 Intermediate Similarity NPD2799 Discontinued
0.7095 Intermediate Similarity NPD3748 Approved
0.7083 Intermediate Similarity NPD3027 Phase 3
0.7075 Intermediate Similarity NPD6651 Approved
0.7071 Intermediate Similarity NPD9717 Approved
0.7037 Intermediate Similarity NPD6959 Discontinued
0.7034 Intermediate Similarity NPD2313 Discontinued
0.7034 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD920 Approved
0.7013 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7768 Phase 2
0.6993 Remote Similarity NPD643 Clinical (unspecified phase)
0.6993 Remote Similarity NPD2798 Approved
0.6988 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6988 Remote Similarity NPD5844 Phase 1
0.6964 Remote Similarity NPD6559 Discontinued
0.6943 Remote Similarity NPD3226 Approved
0.6933 Remote Similarity NPD9570 Approved
0.6918 Remote Similarity NPD411 Approved
0.6917 Remote Similarity NPD4750 Phase 3
0.6908 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6905 Remote Similarity NPD5953 Discontinued
0.6892 Remote Similarity NPD1933 Approved
0.6887 Remote Similarity NPD2346 Discontinued
0.6879 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6875 Remote Similarity NPD257 Approved
0.6875 Remote Similarity NPD258 Approved
0.6871 Remote Similarity NPD520 Approved
0.6863 Remote Similarity NPD8166 Discontinued
0.6863 Remote Similarity NPD4628 Phase 3
0.6839 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6835 Remote Similarity NPD3455 Phase 2
0.6828 Remote Similarity NPD9569 Approved
0.6826 Remote Similarity NPD3751 Discontinued
0.6821 Remote Similarity NPD6100 Approved
0.6821 Remote Similarity NPD6099 Approved
0.6816 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6797 Remote Similarity NPD2654 Approved
0.6794 Remote Similarity NPD1237 Approved
0.6786 Remote Similarity NPD7286 Phase 2
0.6782 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6781 Remote Similarity NPD6832 Phase 2
0.6779 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6776 Remote Similarity NPD7266 Discontinued
0.6763 Remote Similarity NPD5536 Phase 2
0.6761 Remote Similarity NPD422 Phase 1
0.6755 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6741 Remote Similarity NPD9280 Clinical (unspecified phase)
0.6738 Remote Similarity NPD2932 Approved
0.6738 Remote Similarity NPD3019 Approved
0.6731 Remote Similarity NPD4357 Discontinued
0.6714 Remote Similarity NPD1548 Phase 1
0.6713 Remote Similarity NPD3972 Approved
0.6713 Remote Similarity NPD1608 Approved
0.6707 Remote Similarity NPD1220 Phase 1
0.6707 Remote Similarity NPD6234 Discontinued
0.6693 Remote Similarity NPD2934 Approved
0.6693 Remote Similarity NPD2933 Approved
0.6691 Remote Similarity NPD228 Approved
0.6686 Remote Similarity NPD6020 Phase 2
0.6667 Remote Similarity NPD1471 Phase 3
0.6667 Remote Similarity NPD8150 Discontinued
0.6667 Remote Similarity NPD1653 Approved
0.6647 Remote Similarity NPD5242 Approved
0.6645 Remote Similarity NPD4308 Phase 3
0.6645 Remote Similarity NPD1196 Approved
0.6645 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6644 Remote Similarity NPD259 Phase 1
0.6643 Remote Similarity NPD1610 Phase 2
0.6642 Remote Similarity NPD9379 Approved
0.6642 Remote Similarity NPD9377 Approved
0.6641 Remote Similarity NPD2860 Approved
0.6641 Remote Similarity NPD2859 Approved
0.6628 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6627 Remote Similarity NPD7199 Phase 2
0.6626 Remote Similarity NPD2296 Approved
0.6624 Remote Similarity NPD1543 Discontinued
0.6622 Remote Similarity NPD9537 Phase 1
0.6622 Remote Similarity NPD9536 Phase 1
0.6615 Remote Similarity NPD3020 Approved
0.6613 Remote Similarity NPD9094 Approved
0.661 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6609 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6605 Remote Similarity NPD37 Approved
0.66 Remote Similarity NPD825 Approved
0.66 Remote Similarity NPD826 Approved
0.6599 Remote Similarity NPD3018 Phase 2
0.6588 Remote Similarity NPD1221 Approved
0.6587 Remote Similarity NPD5710 Approved
0.6587 Remote Similarity NPD5711 Approved
0.6587 Remote Similarity NPD3787 Discontinued
0.6581 Remote Similarity NPD1195 Approved
0.6577 Remote Similarity NPD3268 Approved

Structure

External Identifiers

PubChem CID   45279391
ChEMBL   CHEMBL1082538
ZINC  

Physicochemical Properties

Molecular Weight:  272.07
ALogP:  -1.7439
MLogP:  2.56
XLogP:  2.659
# Rotatable Bonds:  7
Polar Surface Area:  97.99
# H-Bond Aceptor:  1
# H-Bond Donor:  4
# Rings:  2
# Heavy Atoms:  20

Download Data

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