Natural Product: NPC26386

Natural Product ID:  NPC26386
Common Name:   Burmanin C
IUPAC Name:   2-(1,7-dihydroxy-4,8-dimethoxy-3-methylnaphthalen-2-yl)-5-methoxy-7-methylnaphthalene-1,4-dione
Synonyms:   Burmanin C
Molecular Formula:   C25H22O7
Standard InCHIKey:  WIPIGOWWHMKYKO-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C25H22O7/c1-11-8-14-20(18(9-11)30-3)17(27)10-15(22(14)28)19-12(2)24(31-4)13-6-7-16(26)25(32-5)21(13)23(19)29/h6-10,26,29H,1-5H3
Canonical SMILES:  COc1cc(C)cc2c1C(=O)C=C(C2=O)c1c(C)c(OC)c2c(c1O)c(OC)c(cc2)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
NPO32707 burman diospyros burmanica Species NA NA PMID[22858297]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT841 Organism Leishmania major Leishmania major IC50 = 0.15 nM 21868221
NPT2 Others Unspecified Ratio IC50 = 147 19115838
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 22000 nM 20553004

  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 NPC26386 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
0.9554 High Similarity NPC311740
0.9548 High Similarity NPC279605
0.949 High Similarity NPC84571
0.9363 High Similarity NPC37543
0.9363 High Similarity NPC199463
0.9363 High Similarity NPC178976
0.9299 High Similarity NPC5379
0.9299 High Similarity NPC77807
0.9299 High Similarity NPC14561
0.929 High Similarity NPC302783
0.929 High Similarity NPC473201
0.9231 High Similarity NPC164912
0.9193 High Similarity NPC270837
0.9172 High Similarity NPC107109
0.9167 High Similarity NPC144283
0.9167 High Similarity NPC118427
0.913 High Similarity NPC294965
0.9108 High Similarity NPC312338
0.9108 High Similarity NPC149889
0.9091 High Similarity NPC158226
0.9085 High Similarity NPC163130
0.9085 High Similarity NPC165979
0.908 High Similarity NPC37870
0.9074 High Similarity NPC101769
0.9074 High Similarity NPC236132
0.9068 High Similarity NPC66288
0.9062 High Similarity NPC245891
0.9062 High Similarity NPC45846
0.9062 High Similarity NPC104876
0.9057 High Similarity NPC474167
0.9057 High Similarity NPC470762
0.9045 High Similarity NPC78505
0.9024 High Similarity NPC234331
0.9018 High Similarity NPC275780
0.9018 High Similarity NPC472450
0.9018 High Similarity NPC239752
0.9006 High Similarity NPC56085
0.9006 High Similarity NPC14353
0.9006 High Similarity NPC228785
0.8994 High Similarity NPC134287
0.8994 High Similarity NPC130589
0.8994 High Similarity NPC226656
0.8994 High Similarity NPC66508
0.8994 High Similarity NPC39184
0.8987 High Similarity NPC3744
0.8987 High Similarity NPC137125
0.8982 High Similarity NPC245975
0.8981 High Similarity NPC294646
0.897 High Similarity NPC476637
0.897 High Similarity NPC99613
0.897 High Similarity NPC49487
0.8963 High Similarity NPC29160
0.8963 High Similarity NPC39091
0.8957 High Similarity NPC23298
0.8957 High Similarity NPC236521
0.8957 High Similarity NPC220313
0.8957 High Similarity NPC189473
0.8957 High Similarity NPC197168
0.8957 High Similarity NPC477689
0.8957 High Similarity NPC152659
0.8957 High Similarity NPC207690
0.8957 High Similarity NPC248638
0.8951 High Similarity NPC278052
0.8951 High Similarity NPC40491
0.8951 High Similarity NPC61010
0.8944 High Similarity NPC324736
0.8944 High Similarity NPC100123
0.8931 High Similarity NPC93552
0.8931 High Similarity NPC124714
0.8929 High Similarity NPC49667
0.8929 High Similarity NPC8127
0.8929 High Similarity NPC216307
0.8924 High Similarity NPC306011
0.8924 High Similarity NPC472838
0.8924 High Similarity NPC70320
0.8922 High Similarity NPC473834
0.8917 High Similarity NPC92722
0.8917 High Similarity NPC102003
0.8903 High Similarity NPC73416
0.8903 High Similarity NPC160777
0.8902 High Similarity NPC25361
0.8902 High Similarity NPC303174
0.8896 High Similarity NPC83922
0.8896 High Similarity NPC229632
0.8896 High Similarity NPC25152
0.8896 High Similarity NPC149389
0.8896 High Similarity NPC329760
0.8896 High Similarity NPC472448
0.8896 High Similarity NPC470694
0.8889 High Similarity NPC476980
0.8889 High Similarity NPC161947
0.8889 High Similarity NPC119224
0.8889 High Similarity NPC320359
0.8889 High Similarity NPC155302
0.8882 High Similarity NPC165977
0.8882 High Similarity NPC167098
0.8882 High Similarity NPC78103
0.8882 High Similarity NPC262286
0.8882 High Similarity NPC296044
0.8882 High Similarity NPC300727
0.8882 High Similarity NPC36852
0.8882 High Similarity NPC78225
0.8882 High Similarity NPC217677
0.8882 High Similarity NPC241904
0.8875 High Similarity NPC472048
0.8875 High Similarity NPC66029
0.8869 High Similarity NPC227906
0.8868 High Similarity NPC181209
0.8868 High Similarity NPC216769
0.8868 High Similarity NPC35763
0.8868 High Similarity NPC100971
0.8868 High Similarity NPC245382
0.8868 High Similarity NPC121522
0.8868 High Similarity NPC291802
0.8868 High Similarity NPC209487
0.8868 High Similarity NPC100263
0.8868 High Similarity NPC269451
0.8868 High Similarity NPC131266
0.8862 High Similarity NPC4200
0.8861 High Similarity NPC58310
0.8861 High Similarity NPC472279
0.8861 High Similarity NPC295977
0.8855 High Similarity NPC188079
0.8854 High Similarity NPC287395
0.8854 High Similarity NPC183655
0.8854 High Similarity NPC15329
0.8854 High Similarity NPC131451
0.8848 High Similarity NPC43319
0.8848 High Similarity NPC472449
0.8841 High Similarity NPC7483
0.8841 High Similarity NPC133065
0.8834 High Similarity NPC87431
0.8834 High Similarity NPC278427
0.8834 High Similarity NPC259456
0.8834 High Similarity NPC258331
0.8834 High Similarity NPC29876
0.8834 High Similarity NPC167678
0.8834 High Similarity NPC474187
0.8834 High Similarity NPC32694
0.8827 High Similarity NPC476242
0.882 High Similarity NPC138243
0.882 High Similarity NPC68093
0.882 High Similarity NPC142339
0.882 High Similarity NPC274730
0.882 High Similarity NPC191146
0.8812 High Similarity NPC250557
0.8812 High Similarity NPC273248
0.881 High Similarity NPC65885
0.881 High Similarity NPC216842
0.881 High Similarity NPC82217
0.881 High Similarity NPC310794
0.881 High Similarity NPC476640
0.8805 High Similarity NPC75377
0.8805 High Similarity NPC45291
0.8805 High Similarity NPC262623
0.8805 High Similarity NPC19980
0.8805 High Similarity NPC256406
0.8802 High Similarity NPC109827
0.8802 High Similarity NPC124470
0.8802 High Similarity NPC101107
0.8797 High Similarity NPC134293
0.8795 High Similarity NPC234497
0.8795 High Similarity NPC117854
0.8795 High Similarity NPC472058
0.8795 High Similarity NPC477154
0.8795 High Similarity NPC470341
0.8795 High Similarity NPC324522
0.8795 High Similarity NPC218226
0.8795 High Similarity NPC247973
0.8795 High Similarity NPC50394
0.8795 High Similarity NPC126204
0.8795 High Similarity NPC105414
0.8795 High Similarity NPC6588
0.879 High Similarity NPC289042
0.879 High Similarity NPC119660
0.879 High Similarity NPC118027
0.879 High Similarity NPC190648
0.879 High Similarity NPC245584
0.879 High Similarity NPC56433
0.879 High Similarity NPC312929
0.879 High Similarity NPC126767
0.879 High Similarity NPC93034
0.8788 High Similarity NPC326520
0.8788 High Similarity NPC39306
0.8788 High Similarity NPC156432
0.878 High Similarity NPC261470
0.878 High Similarity NPC84515
0.878 High Similarity NPC476247
0.878 High Similarity NPC312056
0.8774 High Similarity NPC50954
0.8773 High Similarity NPC472060
0.8773 High Similarity NPC204290
0.8773 High Similarity NPC235018
0.8773 High Similarity NPC472052
0.8773 High Similarity NPC45146
0.8773 High Similarity NPC475886
0.8773 High Similarity NPC471973
0.8773 High Similarity NPC200746
0.8773 High Similarity NPC470342
0.8773 High Similarity NPC474287

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC26386 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
0.913 High Similarity NPD6232 Discontinued
0.908 High Similarity NPD7473 Discontinued
0.8696 High Similarity NPD2801 Approved
0.8671 High Similarity NPD8397 Clinical (unspecified phase)
0.8631 High Similarity NPD5844 Phase 1
0.8466 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8405 Intermediate Similarity NPD1934 Approved
0.8343 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8343 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8343 Intermediate Similarity NPD6166 Phase 2
0.8323 Intermediate Similarity NPD5494 Approved
0.8274 Intermediate Similarity NPD6959 Discontinued
0.8253 Intermediate Similarity NPD3882 Suspended
0.8171 Intermediate Similarity NPD4380 Phase 2
0.8144 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8137 Intermediate Similarity NPD1511 Approved
0.8089 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8086 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.8056 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8038 Intermediate Similarity NPD2935 Discontinued
0.8037 Intermediate Similarity NPD1512 Approved
0.8035 Intermediate Similarity NPD3818 Discontinued
0.8025 Intermediate Similarity NPD7390 Discontinued
0.8024 Intermediate Similarity NPD1465 Phase 2
0.8 Intermediate Similarity NPD3226 Approved
0.7975 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7962 Intermediate Similarity NPD1607 Approved
0.7943 Intermediate Similarity NPD7074 Phase 3
0.7917 Intermediate Similarity NPD7819 Suspended
0.791 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7886 Intermediate Similarity NPD7054 Approved
0.787 Intermediate Similarity NPD3817 Phase 2
0.787 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7866 Intermediate Similarity NPD2532 Approved
0.7866 Intermediate Similarity NPD2534 Approved
0.7866 Intermediate Similarity NPD2533 Approved
0.7862 Intermediate Similarity NPD1510 Phase 2
0.7841 Intermediate Similarity NPD7472 Approved
0.7834 Intermediate Similarity NPD1240 Approved
0.7834 Intermediate Similarity NPD943 Approved
0.7812 Intermediate Similarity NPD5408 Approved
0.7812 Intermediate Similarity NPD5405 Approved
0.7812 Intermediate Similarity NPD5404 Approved
0.7812 Intermediate Similarity NPD5406 Approved
0.7798 Intermediate Similarity NPD7411 Suspended
0.7778 Intermediate Similarity NPD7075 Discontinued
0.7778 Intermediate Similarity NPD3749 Approved
0.7759 Intermediate Similarity NPD3926 Phase 2
0.7754 Intermediate Similarity NPD6776 Approved
0.7754 Intermediate Similarity NPD6778 Approved
0.7754 Intermediate Similarity NPD6780 Approved
0.7754 Intermediate Similarity NPD6781 Approved
0.7754 Intermediate Similarity NPD6782 Approved
0.7754 Intermediate Similarity NPD6779 Approved
0.7754 Intermediate Similarity NPD6777 Approved
0.7753 Intermediate Similarity NPD6559 Discontinued
0.7746 Intermediate Similarity NPD1247 Approved
0.7735 Intermediate Similarity NPD8150 Discontinued
0.7727 Intermediate Similarity NPD3751 Discontinued
0.7719 Intermediate Similarity NPD7768 Phase 2
0.7714 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD6797 Phase 2
0.7697 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.768 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD8313 Approved
0.7667 Intermediate Similarity NPD8312 Approved
0.7665 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD2346 Discontinued
0.7654 Intermediate Similarity NPD7251 Discontinued
0.764 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD6599 Discontinued
0.7632 Intermediate Similarity NPD7435 Discontinued
0.763 Intermediate Similarity NPD6234 Discontinued
0.7622 Intermediate Similarity NPD7003 Approved
0.7622 Intermediate Similarity NPD3750 Approved
0.7617 Intermediate Similarity NPD8151 Discontinued
0.7613 Intermediate Similarity NPD1470 Approved
0.7611 Intermediate Similarity NPD7808 Phase 3
0.7607 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD1549 Phase 2
0.7592 Intermediate Similarity NPD7871 Phase 2
0.7592 Intermediate Similarity NPD7870 Phase 2
0.7561 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD5402 Approved
0.7546 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD2344 Approved
0.7546 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD6801 Discontinued
0.7544 Intermediate Similarity NPD37 Approved
0.7539 Intermediate Similarity NPD7696 Phase 3
0.7539 Intermediate Similarity NPD7697 Approved
0.7539 Intermediate Similarity NPD7698 Approved
0.7487 Intermediate Similarity NPD6534 Approved
0.7487 Intermediate Similarity NPD6535 Approved
0.7486 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD6799 Approved
0.7485 Intermediate Similarity NPD2796 Approved
0.7485 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD7701 Phase 2
0.7471 Intermediate Similarity NPD7458 Discontinued
0.7471 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD2800 Approved
0.7449 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7449 Intermediate Similarity NPD7783 Phase 2
0.743 Intermediate Similarity NPD7228 Approved
0.7429 Intermediate Similarity NPD919 Approved
0.7414 Intermediate Similarity NPD4967 Phase 2
0.7414 Intermediate Similarity NPD4965 Approved
0.7414 Intermediate Similarity NPD4966 Approved
0.741 Intermediate Similarity NPD4628 Phase 3
0.7405 Intermediate Similarity NPD9494 Approved
0.7401 Intermediate Similarity NPD3787 Discontinued
0.7398 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7398 Intermediate Similarity NPD7874 Approved
0.7396 Intermediate Similarity NPD6823 Phase 2
0.7382 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD7700 Phase 2
0.7368 Intermediate Similarity NPD7699 Phase 2
0.7365 Intermediate Similarity NPD2309 Approved
0.736 Intermediate Similarity NPD7801 Approved
0.7355 Intermediate Similarity NPD1201 Approved
0.7346 Intermediate Similarity NPD230 Phase 1
0.7346 Intermediate Similarity NPD447 Suspended
0.7345 Intermediate Similarity NPD7199 Phase 2
0.734 Intermediate Similarity NPD6212 Phase 3
0.734 Intermediate Similarity NPD6213 Phase 3
0.734 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD2799 Discontinued
0.7317 Intermediate Similarity NPD3748 Approved
0.7312 Intermediate Similarity NPD3027 Phase 3
0.7303 Intermediate Similarity NPD5710 Approved
0.7303 Intermediate Similarity NPD5711 Approved
0.7301 Intermediate Similarity NPD6651 Approved
0.7263 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD6190 Approved
0.7258 Intermediate Similarity NPD8434 Phase 2
0.7238 Intermediate Similarity NPD7177 Discontinued
0.7235 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD3300 Phase 2
0.7202 Intermediate Similarity NPD8166 Discontinued
0.7202 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD7685 Pre-registration
0.7169 Intermediate Similarity NPD6100 Approved
0.7169 Intermediate Similarity NPD6099 Approved
0.7169 Intermediate Similarity NPD1551 Phase 2
0.7161 Intermediate Similarity NPD1651 Approved
0.716 Intermediate Similarity NPD3764 Approved
0.716 Intermediate Similarity NPD2313 Discontinued
0.7151 Intermediate Similarity NPD5403 Approved
0.7151 Intermediate Similarity NPD920 Approved
0.7143 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD2798 Approved
0.7122 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD5953 Discontinued
0.7111 Intermediate Similarity NPD7229 Phase 3
0.7107 Intermediate Similarity NPD1283 Approved
0.7101 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD4625 Phase 3
0.7097 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD3972 Approved
0.7081 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD1613 Approved
0.7073 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD8320 Phase 1
0.7056 Intermediate Similarity NPD8319 Approved
0.7055 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD1243 Approved
0.7035 Intermediate Similarity NPD5401 Approved
0.7035 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD1933 Approved
0.7024 Intermediate Similarity NPD1471 Phase 3
0.702 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD7286 Phase 2
0.6989 Remote Similarity NPD7240 Approved
0.6978 Remote Similarity NPD5242 Approved
0.6968 Remote Similarity NPD405 Clinical (unspecified phase)
0.6961 Remote Similarity NPD8127 Discontinued
0.6959 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6957 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6957 Remote Similarity NPD7907 Approved
0.6952 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6942 Remote Similarity NPD4665 Approved
0.6942 Remote Similarity NPD4111 Phase 1
0.6941 Remote Similarity NPD6674 Discontinued
0.6933 Remote Similarity NPD4908 Phase 1
0.6932 Remote Similarity NPD7028 Phase 2
0.6923 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5536 Phase 2
0.6919 Remote Similarity NPD7654 Discontinued
0.6919 Remote Similarity NPD643 Clinical (unspecified phase)
0.6918 Remote Similarity NPD1281 Approved
0.6914 Remote Similarity NPD1653 Approved
0.6911 Remote Similarity NPD4287 Approved
0.691 Remote Similarity NPD8455 Phase 2
0.6899 Remote Similarity NPD4626 Approved
0.6897 Remote Similarity NPD6273 Approved

Structure

External Identifiers

PubChem CID   66553902
ChEMBL   CHEMBL2071223
ZINC  

Physicochemical Properties

Molecular Weight:  434.14
ALogP:  -0.1541
MLogP:  3.44
XLogP:  2.041
# Rotatable Bonds:  11
Polar Surface Area:  102.29
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  32

Download Data

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