Natural Product: NPC195832

Natural Product ID:  NPC195832
Common Name:   3',4',Dihydroxy4,5,6-Trimethoxyaurone
IUPAC Name:   (2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-4,5,6-trimethoxy-1-benzofuran-3-one
Synonyms:   3',4',-Dihydroxy4,5,6-Trimethoxyaurone
Molecular Formula:   C18H16O7
Standard InCHIKey:  KDAHPBGYDUMHRL-QPEQYQDCSA-N
Standard InCHI:  InChI=1S/C18H16O7/c1-22-14-8-12-15(18(24-3)17(14)23-2)16(21)13(25-12)7-9-4-5-10(19)11(20)6-9/h4-8,19-20H,1-3H3/b13-7-
Canonical SMILES:  COc1c(OC)cc2c(c1OC)C(=O)/C(=C/c1ccc(c(c1)O)O)/O2
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
NPO24252 Uvaria hamiltonii Species Annonaceae Eukaryota PMID[14552774]
NPO24252 Uvaria hamiltonii Species Annonaceae Eukaryota leaf and stem PMID[9584399]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified Activity = 10 17325223
NPT2 Others Unspecified Activity = 83 % 17325223
NPT111 Cell Line K562 Homo sapiens IC50 = 12000 nM 23398362
NPT111 Cell Line K562 Homo sapiens Activity = 57 8350085
NPT781 Individual Protein Tubulin alpha chain Sus scrofa IC50 > 50000 nM 17210775
NPT111 Cell Line K562 Homo sapiens Activity = 25 17261620
NPT111 Cell Line K562 Homo sapiens Activity = 18 17261620
NPT2 Others Unspecified IC50 > 20 ug/ml DrugMatrix in vitro pharmacology data

  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 NPC195832 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
0.9677 High Similarity NPC36320
0.9671 High Similarity NPC110070
0.9671 High Similarity NPC101830
0.9671 High Similarity NPC203891
0.9667 High Similarity NPC304954
0.9608 High Similarity NPC18607
0.9608 High Similarity NPC300943
0.9608 High Similarity NPC143828
0.9608 High Similarity NPC253634
0.9608 High Similarity NPC204854
0.9608 High Similarity NPC191459
0.9608 High Similarity NPC22472
0.9608 High Similarity NPC19687
0.9608 High Similarity NPC7846
0.9608 High Similarity NPC193842
0.9608 High Similarity NPC105242
0.9608 High Similarity NPC288669
0.9608 High Similarity NPC115798
0.9608 High Similarity NPC18772
0.9608 High Similarity NPC176300
0.9608 High Similarity NPC25495
0.9608 High Similarity NPC261004
0.9608 High Similarity NPC4481
0.9608 High Similarity NPC9609
0.9608 High Similarity NPC130894
0.9608 High Similarity NPC152166
0.9605 High Similarity NPC245546
0.9605 High Similarity NPC49824
0.9605 High Similarity NPC265511
0.9605 High Similarity NPC43243
0.9605 High Similarity NPC266960
0.9605 High Similarity NPC292107
0.9551 High Similarity NPC45449
0.9548 High Similarity NPC272722
0.9542 High Similarity NPC305663
0.9542 High Similarity NPC93376
0.9542 High Similarity NPC78302
0.9542 High Similarity NPC472438
0.9542 High Similarity NPC176665
0.9542 High Similarity NPC75215
0.9542 High Similarity NPC224137
0.9542 High Similarity NPC189179
0.9542 High Similarity NPC163524
0.9542 High Similarity NPC235215
0.9542 High Similarity NPC227192
0.9542 High Similarity NPC7973
0.9542 High Similarity NPC29841
0.9542 High Similarity NPC287979
0.9539 High Similarity NPC20830
0.9539 High Similarity NPC44079
0.9539 High Similarity NPC256612
0.9539 High Similarity NPC189960
0.9539 High Similarity NPC32557
0.9539 High Similarity NPC201451
0.9539 High Similarity NPC26227
0.9533 High Similarity NPC260582
0.9487 High Similarity NPC1755
0.9487 High Similarity NPC39305
0.9487 High Similarity NPC263092
0.9487 High Similarity NPC1706
0.9487 High Similarity NPC59295
0.9477 High Similarity NPC474520
0.9477 High Similarity NPC178854
0.9477 High Similarity NPC100916
0.9477 High Similarity NPC472916
0.9477 High Similarity NPC55619
0.9477 High Similarity NPC98661
0.9477 High Similarity NPC268161
0.9477 High Similarity NPC200388
0.9477 High Similarity NPC247017
0.9474 High Similarity NPC236223
0.9474 High Similarity NPC231018
0.9474 High Similarity NPC145379
0.9474 High Similarity NPC255350
0.9474 High Similarity NPC183878
0.9474 High Similarity NPC176775
0.9474 High Similarity NPC86485
0.9474 High Similarity NPC78326
0.9474 High Similarity NPC69394
0.9474 High Similarity NPC179126
0.9474 High Similarity NPC47781
0.9474 High Similarity NPC22519
0.9474 High Similarity NPC270620
0.9474 High Similarity NPC274327
0.9474 High Similarity NPC160951
0.9467 High Similarity NPC92722
0.9467 High Similarity NPC102003
0.943 High Similarity NPC76482
0.9423 High Similarity NPC312056
0.9423 High Similarity NPC238995
0.9423 High Similarity NPC84515
0.9419 High Similarity NPC246478
0.9412 High Similarity NPC183597
0.9412 High Similarity NPC163780
0.9412 High Similarity NPC196439
0.9412 High Similarity NPC227325
0.9412 High Similarity NPC167815
0.9412 High Similarity NPC50715
0.9412 High Similarity NPC201136
0.9412 High Similarity NPC2928
0.9412 High Similarity NPC146165
0.9412 High Similarity NPC4455
0.9412 High Similarity NPC92659
0.9412 High Similarity NPC208197
0.9412 High Similarity NPC213622
0.9412 High Similarity NPC2476
0.9412 High Similarity NPC214138
0.9412 High Similarity NPC138360
0.9412 High Similarity NPC280339
0.9412 High Similarity NPC128863
0.9408 High Similarity NPC71334
0.9408 High Similarity NPC301123
0.9408 High Similarity NPC188203
0.9408 High Similarity NPC60972
0.9408 High Similarity NPC131624
0.9408 High Similarity NPC100887
0.9408 High Similarity NPC241498
0.9408 High Similarity NPC39732
0.9408 High Similarity NPC120163
0.9408 High Similarity NPC83508
0.9408 High Similarity NPC198826
0.9408 High Similarity NPC301323
0.9408 High Similarity NPC275836
0.9408 High Similarity NPC275722
0.9408 High Similarity NPC212678
0.9408 High Similarity NPC162313
0.9408 High Similarity NPC25270
0.9408 High Similarity NPC293183
0.9408 High Similarity NPC279989
0.9408 High Similarity NPC156222
0.9408 High Similarity NPC55205
0.9408 High Similarity NPC239128
0.9408 High Similarity NPC256283
0.9408 High Similarity NPC187498
0.9408 High Similarity NPC222830
0.9408 High Similarity NPC57030
0.9408 High Similarity NPC82325
0.94 High Similarity NPC131451
0.94 High Similarity NPC19545
0.94 High Similarity NPC15329
0.9359 High Similarity NPC188486
0.9359 High Similarity NPC308992
0.9355 High Similarity NPC16935
0.9355 High Similarity NPC196879
0.9355 High Similarity NPC152904
0.9346 High Similarity NPC206238
0.9346 High Similarity NPC58382
0.9346 High Similarity NPC246204
0.9346 High Similarity NPC292214
0.9346 High Similarity NPC75279
0.9346 High Similarity NPC88645
0.9346 High Similarity NPC167091
0.9346 High Similarity NPC162351
0.9346 High Similarity NPC271779
0.9346 High Similarity NPC472915
0.9346 High Similarity NPC189130
0.9346 High Similarity NPC276409
0.9346 High Similarity NPC250822
0.9342 High Similarity NPC54394
0.9342 High Similarity NPC252933
0.9342 High Similarity NPC260895
0.9342 High Similarity NPC200740
0.9342 High Similarity NPC236769
0.9342 High Similarity NPC308451
0.9342 High Similarity NPC226973
0.9342 High Similarity NPC208043
0.9342 High Similarity NPC125062
0.9342 High Similarity NPC225731
0.9333 High Similarity NPC140840
0.9333 High Similarity NPC86847
0.9333 High Similarity NPC93034
0.9333 High Similarity NPC119660
0.9333 High Similarity NPC117463
0.9317 High Similarity NPC216842
0.9317 High Similarity NPC476640
0.9317 High Similarity NPC82217
0.9299 High Similarity NPC81679
0.9295 High Similarity NPC476980
0.9295 High Similarity NPC263449
0.929 High Similarity NPC475267
0.929 High Similarity NPC471479
0.929 High Similarity NPC210084
0.929 High Similarity NPC222814
0.929 High Similarity NPC472911
0.929 High Similarity NPC67876
0.929 High Similarity NPC36852
0.929 High Similarity NPC472913
0.929 High Similarity NPC472914
0.929 High Similarity NPC474208
0.929 High Similarity NPC470402
0.929 High Similarity NPC474836
0.929 High Similarity NPC48208
0.929 High Similarity NPC96167
0.929 High Similarity NPC262286
0.929 High Similarity NPC245758
0.929 High Similarity NPC78225
0.929 High Similarity NPC162869
0.929 High Similarity NPC156057
0.929 High Similarity NPC99597
0.929 High Similarity NPC471515

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC195832 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
0.9735 High Similarity NPD3882 Suspended
0.9474 High Similarity NPD2801 Approved
0.9032 High Similarity NPD1934 Approved
0.9013 High Similarity NPD1512 Approved
0.8917 High Similarity NPD3817 Phase 2
0.8882 High Similarity NPD1511 Approved
0.8854 High Similarity NPD2393 Clinical (unspecified phase)
0.8834 High Similarity NPD3818 Discontinued
0.8827 High Similarity NPD6166 Phase 2
0.8827 High Similarity NPD6168 Clinical (unspecified phase)
0.8827 High Similarity NPD6167 Clinical (unspecified phase)
0.8795 High Similarity NPD4338 Clinical (unspecified phase)
0.8696 High Similarity NPD5494 Approved
0.8642 High Similarity NPD1247 Approved
0.8636 High Similarity NPD6799 Approved
0.8581 High Similarity NPD4378 Clinical (unspecified phase)
0.8563 High Similarity NPD6797 Phase 2
0.8512 High Similarity NPD7251 Discontinued
0.8462 Intermediate Similarity NPD7808 Phase 3
0.8457 Intermediate Similarity NPD7075 Discontinued
0.8447 Intermediate Similarity NPD5402 Approved
0.8443 Intermediate Similarity NPD7054 Approved
0.8424 Intermediate Similarity NPD3926 Phase 2
0.8395 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8393 Intermediate Similarity NPD7074 Phase 3
0.8393 Intermediate Similarity NPD7472 Approved
0.8385 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD6599 Discontinued
0.8293 Intermediate Similarity NPD919 Approved
0.8212 Intermediate Similarity NPD943 Approved
0.8212 Intermediate Similarity NPD1240 Approved
0.821 Intermediate Similarity NPD6801 Discontinued
0.8199 Intermediate Similarity NPD4380 Phase 2
0.8194 Intermediate Similarity NPD1549 Phase 2
0.8144 Intermediate Similarity NPD6232 Discontinued
0.8129 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8129 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8129 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8121 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8117 Intermediate Similarity NPD1510 Phase 2
0.8107 Intermediate Similarity NPD7473 Discontinued
0.8105 Intermediate Similarity NPD1607 Approved
0.8065 Intermediate Similarity NPD2796 Approved
0.8049 Intermediate Similarity NPD1465 Phase 2
0.8012 Intermediate Similarity NPD5403 Approved
0.8012 Intermediate Similarity NPD5844 Phase 1
0.8012 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7949 Intermediate Similarity NPD2935 Discontinued
0.7939 Intermediate Similarity NPD7819 Suspended
0.7922 Intermediate Similarity NPD447 Suspended
0.7922 Intermediate Similarity NPD230 Phase 1
0.7911 Intermediate Similarity NPD2800 Approved
0.7901 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7888 Intermediate Similarity NPD5401 Approved
0.7874 Intermediate Similarity NPD6559 Discontinued
0.7848 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7818 Intermediate Similarity NPD7411 Suspended
0.7812 Intermediate Similarity NPD6190 Approved
0.7798 Intermediate Similarity NPD3749 Approved
0.7785 Intermediate Similarity NPD2344 Approved
0.7784 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD2534 Approved
0.7778 Intermediate Similarity NPD2533 Approved
0.7778 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD2532 Approved
0.7746 Intermediate Similarity NPD3751 Discontinued
0.7722 Intermediate Similarity NPD1551 Phase 2
0.7712 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7683 Intermediate Similarity NPD920 Approved
0.7662 Intermediate Similarity NPD3027 Phase 3
0.7661 Intermediate Similarity NPD6959 Discontinued
0.7647 Intermediate Similarity NPD9494 Approved
0.7647 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD3750 Approved
0.7628 Intermediate Similarity NPD1613 Approved
0.7628 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD3787 Discontinued
0.7616 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD2309 Approved
0.7582 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD1243 Approved
0.7569 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD7199 Phase 2
0.7544 Intermediate Similarity NPD6234 Discontinued
0.7531 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD4628 Phase 3
0.753 Intermediate Similarity NPD1653 Approved
0.7529 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD2403 Approved
0.7529 Intermediate Similarity NPD7768 Phase 2
0.7469 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD1933 Approved
0.7459 Intermediate Similarity NPD8434 Phase 2
0.7439 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD2799 Discontinued
0.7416 Intermediate Similarity NPD5953 Discontinued
0.7403 Intermediate Similarity NPD1203 Approved
0.7401 Intermediate Similarity NPD7286 Phase 2
0.7394 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD3226 Approved
0.7353 Intermediate Similarity NPD37 Approved
0.7346 Intermediate Similarity NPD1471 Phase 3
0.7345 Intermediate Similarity NPD2163 Approved
0.7342 Intermediate Similarity NPD6233 Phase 2
0.7333 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD3748 Approved
0.7329 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD4965 Approved
0.7326 Intermediate Similarity NPD4966 Approved
0.7326 Intermediate Similarity NPD4967 Phase 2
0.732 Intermediate Similarity NPD9269 Phase 2
0.7312 Intermediate Similarity NPD6651 Approved
0.7289 Intermediate Similarity NPD4357 Discontinued
0.7284 Intermediate Similarity NPD6099 Approved
0.7284 Intermediate Similarity NPD6100 Approved
0.7278 Intermediate Similarity NPD7685 Pre-registration
0.7278 Intermediate Similarity NPD2313 Discontinued
0.7273 Intermediate Similarity NPD5242 Approved
0.7261 Intermediate Similarity NPD6832 Phase 2
0.7256 Intermediate Similarity NPD2654 Approved
0.725 Intermediate Similarity NPD6355 Discontinued
0.725 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7247 Intermediate Similarity NPD7228 Approved
0.7239 Intermediate Similarity NPD2346 Discontinued
0.7234 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD5711 Approved
0.7216 Intermediate Similarity NPD5710 Approved
0.7211 Intermediate Similarity NPD6780 Approved
0.7211 Intermediate Similarity NPD6776 Approved
0.7211 Intermediate Similarity NPD6778 Approved
0.7211 Intermediate Similarity NPD6779 Approved
0.7211 Intermediate Similarity NPD6777 Approved
0.7211 Intermediate Similarity NPD6782 Approved
0.7211 Intermediate Similarity NPD6781 Approved
0.7208 Intermediate Similarity NPD9717 Approved
0.7193 Intermediate Similarity NPD6386 Approved
0.7193 Intermediate Similarity NPD6385 Approved
0.7188 Intermediate Similarity NPD7435 Discontinued
0.717 Intermediate Similarity NPD6798 Discontinued
0.7169 Intermediate Similarity NPD2354 Approved
0.7168 Intermediate Similarity NPD5353 Approved
0.7152 Intermediate Similarity NPD5536 Phase 2
0.7151 Intermediate Similarity NPD6844 Discontinued
0.7108 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD3018 Phase 2
0.7083 Intermediate Similarity NPD7390 Discontinued
0.7081 Intermediate Similarity NPD4060 Phase 1
0.7081 Intermediate Similarity NPD8150 Discontinued
0.7069 Intermediate Similarity NPD2296 Approved
0.7063 Intermediate Similarity NPD411 Approved
0.7059 Intermediate Similarity NPD9268 Approved
0.7044 Intermediate Similarity NPD4908 Phase 1
0.7044 Intermediate Similarity NPD7907 Approved
0.7039 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD422 Phase 1
0.7025 Intermediate Similarity NPD2798 Approved
0.7022 Intermediate Similarity NPD7229 Phase 3
0.7012 Intermediate Similarity NPD7033 Discontinued
0.7011 Intermediate Similarity NPD8313 Approved
0.7011 Intermediate Similarity NPD8312 Approved
0.701 Intermediate Similarity NPD7698 Approved
0.701 Intermediate Similarity NPD7696 Phase 3
0.701 Intermediate Similarity NPD7697 Approved
0.7 Intermediate Similarity NPD5049 Phase 3
0.6995 Remote Similarity NPD2494 Approved
0.6995 Remote Similarity NPD2493 Approved
0.6993 Remote Similarity NPD1548 Phase 1
0.6987 Remote Similarity NPD1608 Approved
0.6981 Remote Similarity NPD2861 Phase 2
0.6978 Remote Similarity NPD1729 Discontinued
0.6974 Remote Similarity NPD7871 Phase 2
0.6974 Remote Similarity NPD7870 Phase 2
0.697 Remote Similarity NPD7874 Approved
0.697 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6964 Remote Similarity NPD3887 Approved
0.6957 Remote Similarity NPD3764 Approved
0.6957 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6957 Remote Similarity NPD3268 Approved
0.6954 Remote Similarity NPD7701 Phase 2
0.6947 Remote Similarity NPD6534 Approved
0.6947 Remote Similarity NPD6535 Approved
0.6946 Remote Similarity NPD2899 Discontinued
0.6946 Remote Similarity NPD4111 Phase 1
0.6946 Remote Similarity NPD4665 Approved
0.6944 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6943 Remote Similarity NPD2982 Phase 2
0.6943 Remote Similarity NPD2983 Phase 2
0.6941 Remote Similarity NPD3146 Approved
0.6941 Remote Similarity NPD3688 Clinical (unspecified phase)
0.6941 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6941 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6932 Remote Similarity NPD5019 Clinical (unspecified phase)
0.6928 Remote Similarity NPD2343 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   642382
ChEMBL   CHEMBL124392
ZINC  

Physicochemical Properties

Molecular Weight:  344.09
ALogP:  -1.4729
MLogP:  2.67
XLogP:  1.96
# Rotatable Bonds:  9
Polar Surface Area:  94.45
# H-Bond Aceptor:  1
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  25

Download Data

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