Natural Product: NPC477396

Natural Product ID:  NPC477396
Common Name:   Kopsimaline D
IUPAC Name:  
Synonyms:   Kopsimaline D
Molecular Formula:   C24H26N2O10
Standard InCHIKey:  XMKHYZHGKGQZTD-FFPJCSTLSA-N
Standard InCHI:  InChI=1S/C24H26N2O10/c1-32-19(29)24(31)18(28)23-13(27)7-22(24)21(5-6-25(17(21)23)8-12-16(23)36-12)10-3-4-11-15(35-9-34-11)14(10)26(22)20(30)33-2/h3-4,12-13,16-18,27-28,31H,5-9H2,1-2H3/t12-,13-,16-,17+,18+,21+,22-,23+,24+/m0/s1
Canonical SMILES:  COC(=O)N1c2c3OCOc3ccc2[C@]23[C@@]41C[C@H](O)[C@]1([C@H]([C@@]4(O)C(=O)OC)O)[C@@H]3N(CC2)C[C@H]2[C@@H]1O2
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
NPO19270 Kopsia singapurensis Species Apocynaceae Eukaryota leaf and stem-bark Pahang, Malaysia 1996-JUL PMID[18078327]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT91 Cell Line KB Homo sapiens IC50 = 9.2 ug/ml 18078327
NPT2 Others Unspecified IC50 = 25 ug/ml 18078327

  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 NPC477396 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
0.9908 High Similarity NPC477393
0.9457 High Similarity NPC477395
0.9174 High Similarity NPC471513
0.9005 High Similarity NPC477397
0.8914 High Similarity NPC473458
0.8682 High Similarity NPC222046
0.8597 High Similarity NPC288110
0.8571 High Similarity NPC477394
0.8162 Intermediate Similarity NPC291173
0.8161 Intermediate Similarity NPC127996
0.8095 Intermediate Similarity NPC470480
0.807 Intermediate Similarity NPC10653
0.807 Intermediate Similarity NPC318525
0.8009 Intermediate Similarity NPC19175
0.7955 Intermediate Similarity NPC471512
0.7939 Intermediate Similarity NPC195636
0.7895 Intermediate Similarity NPC234772
0.789 Intermediate Similarity NPC160113
0.789 Intermediate Similarity NPC476220
0.7879 Intermediate Similarity NPC128476
0.7854 Intermediate Similarity NPC231924
0.7835 Intermediate Similarity NPC476069
0.7833 Intermediate Similarity NPC476258
0.7833 Intermediate Similarity NPC304837
0.7763 Intermediate Similarity NPC159815
0.7749 Intermediate Similarity NPC77777
0.7748 Intermediate Similarity NPC474427
0.7708 Intermediate Similarity NPC154922
0.7695 Intermediate Similarity NPC113455
0.7682 Intermediate Similarity NPC221687
0.7673 Intermediate Similarity NPC120239
0.7655 Intermediate Similarity NPC246140
0.7655 Intermediate Similarity NPC195787
0.765 Intermediate Similarity NPC46259
0.7617 Intermediate Similarity NPC148124
0.7613 Intermediate Similarity NPC475713
0.7613 Intermediate Similarity NPC474432
0.7574 Intermediate Similarity NPC99724
0.7568 Intermediate Similarity NPC473375
0.7568 Intermediate Similarity NPC97100
0.7563 Intermediate Similarity NPC248903
0.7534 Intermediate Similarity NPC161804
0.7522 Intermediate Similarity NPC475747
0.7521 Intermediate Similarity NPC26928
0.748 Intermediate Similarity NPC469452
0.7457 Intermediate Similarity NPC10732
0.7446 Intermediate Similarity NPC269449
0.7419 Intermediate Similarity NPC329932
0.7409 Intermediate Similarity NPC469722
0.7398 Intermediate Similarity NPC469450
0.7378 Intermediate Similarity NPC66909
0.7358 Intermediate Similarity NPC301501
0.7357 Intermediate Similarity NPC127178
0.7357 Intermediate Similarity NPC67904
0.7339 Intermediate Similarity NPC469451
0.7331 Intermediate Similarity NPC126556
0.7325 Intermediate Similarity NPC254045
0.7325 Intermediate Similarity NPC201055
0.7325 Intermediate Similarity NPC64576
0.7325 Intermediate Similarity NPC151470
0.7317 Intermediate Similarity NPC131977
0.7308 Intermediate Similarity NPC470481
0.7308 Intermediate Similarity NPC119722
0.7308 Intermediate Similarity NPC470482
0.7304 Intermediate Similarity NPC470484
0.7304 Intermediate Similarity NPC87714
0.73 Intermediate Similarity NPC87560
0.7293 Intermediate Similarity NPC1464
0.7281 Intermediate Similarity NPC138830
0.7269 Intermediate Similarity NPC193906
0.7269 Intermediate Similarity NPC23080
0.726 Intermediate Similarity NPC15919
0.7238 Intermediate Similarity NPC157983
0.7238 Intermediate Similarity NPC118154
0.7231 Intermediate Similarity NPC266994
0.7229 Intermediate Similarity NPC475147
0.7227 Intermediate Similarity NPC195120
0.7213 Intermediate Similarity NPC223242
0.7207 Intermediate Similarity NPC474746
0.7207 Intermediate Similarity NPC475981
0.7205 Intermediate Similarity NPC120671
0.7205 Intermediate Similarity NPC226652
0.7205 Intermediate Similarity NPC72788
0.7205 Intermediate Similarity NPC314100
0.7191 Intermediate Similarity NPC82541
0.7179 Intermediate Similarity NPC475133
0.7175 Intermediate Similarity NPC9867
0.7173 Intermediate Similarity NPC189661
0.7172 Intermediate Similarity NPC74216
0.7168 Intermediate Similarity NPC470485
0.716 Intermediate Similarity NPC476436
0.716 Intermediate Similarity NPC285254
0.7155 Intermediate Similarity NPC268077
0.7154 Intermediate Similarity NPC139373
0.7143 Intermediate Similarity NPC202771
0.7143 Intermediate Similarity NPC2173
0.7143 Intermediate Similarity NPC230098
0.7143 Intermediate Similarity NPC119818
0.7143 Intermediate Similarity NPC328700
0.7138 Intermediate Similarity NPC260909
0.7137 Intermediate Similarity NPC76478
0.7136 Intermediate Similarity NPC474470
0.7131 Intermediate Similarity NPC13249
0.7125 Intermediate Similarity NPC219397
0.7124 Intermediate Similarity NPC80472
0.7118 Intermediate Similarity NPC14622
0.7118 Intermediate Similarity NPC73020
0.7118 Intermediate Similarity NPC46744
0.7118 Intermediate Similarity NPC215098
0.7118 Intermediate Similarity NPC124302
0.7118 Intermediate Similarity NPC70290
0.7116 Intermediate Similarity NPC195788
0.7116 Intermediate Similarity NPC237901
0.7111 Intermediate Similarity NPC237579
0.7107 Intermediate Similarity NPC250960
0.7107 Intermediate Similarity NPC71539
0.7106 Intermediate Similarity NPC477160
0.7105 Intermediate Similarity NPC162653
0.71 Intermediate Similarity NPC471489
0.7094 Intermediate Similarity NPC11708
0.7085 Intermediate Similarity NPC476429
0.708 Intermediate Similarity NPC470483
0.7078 Intermediate Similarity NPC65403
0.7072 Intermediate Similarity NPC474745
0.7069 Intermediate Similarity NPC286135
0.7066 Intermediate Similarity NPC7560
0.7066 Intermediate Similarity NPC118189
0.7059 Intermediate Similarity NPC114468
0.7054 Intermediate Similarity NPC108826
0.7054 Intermediate Similarity NPC156576
0.7051 Intermediate Similarity NPC476500
0.7049 Intermediate Similarity NPC122886
0.7043 Intermediate Similarity NPC17677
0.7039 Intermediate Similarity NPC207971
0.7032 Intermediate Similarity NPC311991
0.7031 Intermediate Similarity NPC33256
0.7029 Intermediate Similarity NPC148391
0.7027 Intermediate Similarity NPC118633
0.7027 Intermediate Similarity NPC474325
0.7027 Intermediate Similarity NPC294790
0.7027 Intermediate Similarity NPC148693
0.7018 Intermediate Similarity NPC302001
0.7018 Intermediate Similarity NPC94499
0.7016 Intermediate Similarity NPC475316
0.7016 Intermediate Similarity NPC473486
0.7014 Intermediate Similarity NPC304675
0.7012 Intermediate Similarity NPC134702
0.7009 Intermediate Similarity NPC248642
0.7004 Intermediate Similarity NPC470821
0.6987 Remote Similarity NPC268223
0.6982 Remote Similarity NPC237044
0.6976 Remote Similarity NPC470631
0.6976 Remote Similarity NPC35390
0.6976 Remote Similarity NPC473781
0.6974 Remote Similarity NPC319549
0.6962 Remote Similarity NPC168250
0.696 Remote Similarity NPC474059
0.696 Remote Similarity NPC141440
0.696 Remote Similarity NPC105055
0.696 Remote Similarity NPC22689
0.6958 Remote Similarity NPC2905
0.6957 Remote Similarity NPC470646
0.6944 Remote Similarity NPC151171
0.6942 Remote Similarity NPC182853
0.6923 Remote Similarity NPC470739
0.6923 Remote Similarity NPC225597
0.6923 Remote Similarity NPC477640
0.692 Remote Similarity NPC126284
0.692 Remote Similarity NPC99179
0.692 Remote Similarity NPC244554
0.6916 Remote Similarity NPC214116
0.6909 Remote Similarity NPC266176
0.6909 Remote Similarity NPC158148
0.6909 Remote Similarity NPC290759
0.6909 Remote Similarity NPC82533
0.69 Remote Similarity NPC196231
0.69 Remote Similarity NPC63152
0.6898 Remote Similarity NPC251071
0.6897 Remote Similarity NPC218733
0.6897 Remote Similarity NPC138615
0.6897 Remote Similarity NPC132874
0.6897 Remote Similarity NPC265642
0.6891 Remote Similarity NPC46990
0.6889 Remote Similarity NPC115906
0.6878 Remote Similarity NPC474475
0.6878 Remote Similarity NPC474708
0.687 Remote Similarity NPC78284
0.6867 Remote Similarity NPC267414
0.6867 Remote Similarity NPC5374
0.6861 Remote Similarity NPC287152
0.6861 Remote Similarity NPC187678
0.6853 Remote Similarity NPC90967
0.6846 Remote Similarity NPC321166
0.6846 Remote Similarity NPC217903
0.6846 Remote Similarity NPC30749
0.6844 Remote Similarity NPC149285
0.6844 Remote Similarity NPC220961
0.6844 Remote Similarity NPC37957
0.6833 Remote Similarity NPC475845
0.6833 Remote Similarity NPC58766

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC477396 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
0.7699 Intermediate Similarity NPD6625 Approved
0.7378 Intermediate Similarity NPD2975 Approved
0.7378 Intermediate Similarity NPD2973 Approved
0.7378 Intermediate Similarity NPD2974 Approved
0.7357 Intermediate Similarity NPD4580 Approved
0.7333 Intermediate Similarity NPD5582 Discontinued
0.7325 Intermediate Similarity NPD2493 Approved
0.7325 Intermediate Similarity NPD3452 Approved
0.7325 Intermediate Similarity NPD3450 Approved
0.7325 Intermediate Similarity NPD2494 Approved
0.7304 Intermediate Similarity NPD4583 Approved
0.7304 Intermediate Similarity NPD4582 Approved
0.7261 Intermediate Similarity NPD4002 Approved
0.7261 Intermediate Similarity NPD4004 Approved
0.7197 Intermediate Similarity NPD2899 Discontinued
0.7178 Intermediate Similarity NPD6997 Phase 2
0.7143 Intermediate Similarity NPD5005 Approved
0.7143 Intermediate Similarity NPD5006 Approved
0.7138 Intermediate Similarity NPD8459 Approved
0.7138 Intermediate Similarity NPD8460 Approved
0.7118 Intermediate Similarity NPD4420 Approved
0.7116 Intermediate Similarity NPD8466 Approved
0.7116 Intermediate Similarity NPD8465 Approved
0.7116 Intermediate Similarity NPD8467 Approved
0.7108 Intermediate Similarity NPD7048 Phase 3
0.7056 Intermediate Similarity NPD6723 Discontinued
0.704 Intermediate Similarity NPD4846 Phase 2
0.7011 Intermediate Similarity NPD8426 Approved
0.7011 Intermediate Similarity NPD8425 Approved
0.6989 Remote Similarity NPD8428 Approved
0.6989 Remote Similarity NPD8429 Approved
0.6989 Remote Similarity NPD8427 Approved
0.6974 Remote Similarity NPD7296 Approved
0.693 Remote Similarity NPD2490 Approved
0.693 Remote Similarity NPD2488 Approved
0.6929 Remote Similarity NPD7047 Phase 3
0.6926 Remote Similarity NPD7907 Approved
0.6916 Remote Similarity NPD7906 Approved
0.6914 Remote Similarity NPD4111 Phase 1
0.6889 Remote Similarity NPD2968 Approved
0.6889 Remote Similarity NPD2971 Approved
0.687 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6864 Remote Similarity NPD4040 Phase 1
0.6851 Remote Similarity NPD956 Clinical (unspecified phase)
0.6849 Remote Similarity NPD4859 Phase 1
0.6844 Remote Similarity NPD4665 Approved
0.6828 Remote Similarity NPD8363 Approved
0.6828 Remote Similarity NPD8364 Approved
0.6815 Remote Similarity NPD7186 Phase 3
0.6806 Remote Similarity NPD8461 Discontinued
0.6805 Remote Similarity NPD7827 Phase 1
0.6798 Remote Similarity NPD4663 Approved
0.6794 Remote Similarity NPD8492 Approved
0.6778 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6751 Remote Similarity NPD7497 Discontinued
0.674 Remote Similarity NPD4578 Approved
0.674 Remote Similarity NPD4577 Approved
0.6738 Remote Similarity NPD8489 Phase 1
0.6721 Remote Similarity NPD7805 Phase 3
0.6705 Remote Similarity NPD8367 Approved
0.6681 Remote Similarity NPD6211 Clinical (unspecified phase)
0.668 Remote Similarity NPD3437 Discontinued
0.668 Remote Similarity NPD7223 Discontinued
0.668 Remote Similarity NPD7224 Discontinued
0.6667 Remote Similarity NPD5312 Approved
0.6667 Remote Similarity NPD5313 Approved
0.6667 Remote Similarity NPD7280 Phase 3
0.6667 Remote Similarity NPD7281 Phase 3
0.6667 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6654 Remote Similarity NPD7955 Approved
0.6654 Remote Similarity NPD7803 Approved
0.6654 Remote Similarity NPD7956 Approved
0.6653 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6638 Remote Similarity NPD6621 Clinical (unspecified phase)
0.6626 Remote Similarity NPD683 Approved
0.6626 Remote Similarity NPD5676 Approved
0.6616 Remote Similarity NPD6503 Clinical (unspecified phase)
0.66 Remote Similarity NPD3912 Discontinued
0.6592 Remote Similarity NPD3051 Approved
0.6575 Remote Similarity NPD8067 Phase 3
0.6569 Remote Similarity NPD3057 Approved
0.6559 Remote Similarity NPD8404 Phase 2
0.6557 Remote Similarity NPD1945 Phase 1
0.6556 Remote Similarity NPD7174 Clinical (unspecified phase)
0.6555 Remote Similarity NPD4107 Approved
0.6533 Remote Similarity NPD4481 Phase 3
0.6533 Remote Similarity NPD6365 Clinical (unspecified phase)
0.6522 Remote Similarity NPD3534 Clinical (unspecified phase)
0.652 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6515 Remote Similarity NPD8153 Approved
0.6515 Remote Similarity NPD8152 Approved
0.6506 Remote Similarity NPD7708 Approved
0.6502 Remote Similarity NPD7701 Phase 2
0.65 Remote Similarity NPD3533 Approved
0.65 Remote Similarity NPD2972 Approved
0.6498 Remote Similarity NPD7238 Clinical (unspecified phase)
0.6494 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6492 Remote Similarity NPD3940 Clinical (unspecified phase)
0.6489 Remote Similarity NPD2969 Approved
0.6489 Remote Similarity NPD2970 Approved
0.648 Remote Similarity NPD5433 Clinical (unspecified phase)
0.648 Remote Similarity NPD7858 Clinical (unspecified phase)
0.6475 Remote Similarity NPD6517 Phase 3
0.6463 Remote Similarity NPD7178 Clinical (unspecified phase)
0.6462 Remote Similarity NPD7025 Clinical (unspecified phase)
0.6462 Remote Similarity NPD7560 Approved
0.6461 Remote Similarity NPD4596 Phase 1
0.6461 Remote Similarity NPD7263 Phase 2
0.6458 Remote Similarity NPD4482 Phase 3
0.645 Remote Similarity NPD7313 Approved
0.645 Remote Similarity NPD7311 Approved
0.645 Remote Similarity NPD7312 Approved
0.645 Remote Similarity NPD7310 Approved
0.6446 Remote Similarity NPD3298 Approved
0.6446 Remote Similarity NPD6644 Discontinued
0.6446 Remote Similarity NPD5102 Clinical (unspecified phase)
0.6443 Remote Similarity NPD7821 Clinical (unspecified phase)
0.6437 Remote Similarity NPD4455 Discontinued
0.6435 Remote Similarity NPD7149 Clinical (unspecified phase)
0.6434 Remote Similarity NPD2906 Approved
0.6434 Remote Similarity NPD2907 Approved
0.6432 Remote Similarity NPD2491 Approved
0.6432 Remote Similarity NPD3448 Approved
0.6423 Remote Similarity NPD4493 Discontinued
0.6422 Remote Similarity NPD7309 Approved
0.6422 Remote Similarity NPD6851 Approved
0.6422 Remote Similarity NPD6853 Approved
0.6421 Remote Similarity NPD7862 Clinical (unspecified phase)
0.642 Remote Similarity NPD7999 Approved
0.6412 Remote Similarity NPD6716 Phase 1
0.6405 Remote Similarity NPD7597 Clinical (unspecified phase)
0.6403 Remote Similarity NPD7278 Phase 2
0.6403 Remote Similarity NPD7279 Phase 2
0.6397 Remote Similarity NPD4492 Approved
0.6397 Remote Similarity NPD4494 Approved
0.6393 Remote Similarity NPD7583 Approved
0.6391 Remote Similarity NPD6496 Clinical (unspecified phase)
0.639 Remote Similarity NPD6238 Discontinued
0.6388 Remote Similarity NPD2489 Approved
0.6388 Remote Similarity NPD27 Approved
0.6383 Remote Similarity NPD7235 Clinical (unspecified phase)
0.6382 Remote Similarity NPD5860 Discontinued
0.6379 Remote Similarity NPD4456 Clinical (unspecified phase)
0.6367 Remote Similarity NPD7585 Approved
0.6367 Remote Similarity NPD4082 Approved
0.6356 Remote Similarity NPD4206 Approved
0.6352 Remote Similarity NPD7607 Clinical (unspecified phase)
0.6349 Remote Similarity NPD7255 Clinical (unspecified phase)
0.6345 Remote Similarity NPD7930 Approved
0.634 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6339 Remote Similarity NPD7820 Phase 3
0.6337 Remote Similarity NPD7064 Clinical (unspecified phase)
0.6331 Remote Similarity NPD7682 Approved
0.6331 Remote Similarity NPD7684 Approved
0.6331 Remote Similarity NPD3888 Discontinued
0.6327 Remote Similarity NPD6773 Clinical (unspecified phase)
0.632 Remote Similarity NPD6297 Approved
0.6316 Remote Similarity NPD3893 Discontinued
0.6307 Remote Similarity NPD6874 Approved
0.6307 Remote Similarity NPD3297 Approved
0.6303 Remote Similarity NPD7125 Discontinued
0.6301 Remote Similarity NPD3472 Approved
0.6301 Remote Similarity NPD4022 Approved
0.6293 Remote Similarity NPD4885 Approved
0.6288 Remote Similarity NPD5938 Phase 3
0.6287 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6285 Remote Similarity NPD3783 Clinical (unspecified phase)
0.6281 Remote Similarity NPD5457 Discontinued
0.628 Remote Similarity NPD7559 Phase 2
0.6275 Remote Similarity NPD3591 Approved
0.6275 Remote Similarity NPD3592 Approved
0.6269 Remote Similarity NPD7922 Phase 1
0.6267 Remote Similarity NPD7690 Clinical (unspecified phase)
0.6266 Remote Similarity NPD4668 Phase 2
0.6266 Remote Similarity NPD5071 Phase 2
0.6261 Remote Similarity NPD4498 Clinical (unspecified phase)
0.626 Remote Similarity NPD7584 Approved
0.625 Remote Similarity NPD3372 Discontinued
0.6245 Remote Similarity NPD8320 Phase 1
0.6245 Remote Similarity NPD2845 Phase 2
0.6245 Remote Similarity NPD2843 Phase 2
0.6245 Remote Similarity NPD5496 Approved
0.6245 Remote Similarity NPD8319 Approved
0.624 Remote Similarity NPD5609 Approved
0.624 Remote Similarity NPD5608 Approved
0.6234 Remote Similarity NPD5600 Discontinued
0.6234 Remote Similarity NPD7262 Phase 1
0.623 Remote Similarity NPD5980 Discovery
0.6228 Remote Similarity NPD6071 Discontinued
0.6224 Remote Similarity NPD4604 Approved
0.6224 Remote Similarity NPD4605 Approved
0.6221 Remote Similarity NPD8357 Approved
0.6216 Remote Similarity NPD6199 Discontinued
0.6214 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6206 Remote Similarity NPD7292 Approved
0.6205 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6203 Remote Similarity NPD6608 Clinical (unspecified phase)
0.6201 Remote Similarity NPD5242 Approved
0.619 Remote Similarity NPD7169 Suspended
0.6186 Remote Similarity NPD8055 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   24770358
ChEMBL   CHEMBL401675
ZINC  

Physicochemical Properties

Molecular Weight:  502.16
ALogP:  -2.822
MLogP:  2.78
XLogP:  -0.95
# Rotatable Bonds:  9
Polar Surface Area:  150.76
# H-Bond Aceptor:  10
# H-Bond Donor:  3
# Rings:  6
# Heavy Atoms:  36

Download Data

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Biological Activities  
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