Natural Product: NPC260343

Natural Product ID:  NPC260343
Common Name:   Glaucolide M
IUPAC Name:   [(4S,6S,7S,10R,11E)-7-acetyloxy-3-(acetyloxymethyl)-10-hydroxy-6,10-dimethyl-2-oxo-4,5,6,7,8,9-hexahydrocyclodeca[b]furan-4-yl] 2-methylprop-2-enoate
Synonyms:   Glaucolide M
Molecular Formula:   C23H30O9
Standard InCHIKey:  ICDFEPLJXGFLMV-QIQGQPBLSA-N
Standard InCHI:  InChI=1S/C23H30O9/c1-12(2)21(26)31-18-9-13(3)17(30-15(5)25)7-8-23(6,28)10-19-20(18)16(22(27)32-19)11-29-14(4)24/h10,13,17-18,28H,1,7-9,11H2,2-6H3/b19-10+/t13-,17-,18-,23+/m0/s1
Canonical SMILES:  CC(=O)OCC1=C2[C@H](C[C@H](C)[C@H](CC[C@@](/C=C2/OC1=O)(C)O)OC(=O)C)OC(=O)C(=C)C
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
NPO22460 Vernonia pachyclada Species Asteraceae Eukaryota Madagascar rainforest PMID[16180816]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT179 Cell Line A2780 Homo sapiens IC50 = 3300 nM 20815366

  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 NPC260343 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
0.8977 High Similarity NPC32494
0.8977 High Similarity NPC175842
0.8876 High Similarity NPC59646
0.8778 High Similarity NPC470521
0.8652 High Similarity NPC3436
0.8556 High Similarity NPC470520
0.8539 High Similarity NPC225283
0.8539 High Similarity NPC242877
0.8539 High Similarity NPC64913
0.8352 Intermediate Similarity NPC158061
0.8298 Intermediate Similarity NPC471490
0.8222 Intermediate Similarity NPC475819
0.8222 Intermediate Similarity NPC476805
0.8202 Intermediate Similarity NPC305475
0.8202 Intermediate Similarity NPC475461
0.8191 Intermediate Similarity NPC230800
0.8105 Intermediate Similarity NPC2666
0.809 Intermediate Similarity NPC255307
0.809 Intermediate Similarity NPC470755
0.809 Intermediate Similarity NPC261380
0.8085 Intermediate Similarity NPC471492
0.8 Intermediate Similarity NPC315394
0.8 Intermediate Similarity NPC469483
0.8 Intermediate Similarity NPC473333
0.8 Intermediate Similarity NPC204048
0.7979 Intermediate Similarity NPC474247
0.7978 Intermediate Similarity NPC158756
0.7978 Intermediate Similarity NPC191476
0.7978 Intermediate Similarity NPC114979
0.7955 Intermediate Similarity NPC85772
0.7889 Intermediate Similarity NPC130030
0.7889 Intermediate Similarity NPC471185
0.7872 Intermediate Similarity NPC475838
0.7872 Intermediate Similarity NPC228451
0.7872 Intermediate Similarity NPC125674
0.7865 Intermediate Similarity NPC169575
0.7865 Intermediate Similarity NPC40746
0.7865 Intermediate Similarity NPC473390
0.7865 Intermediate Similarity NPC116543
0.7865 Intermediate Similarity NPC131669
0.7857 Intermediate Similarity NPC470686
0.7857 Intermediate Similarity NPC469851
0.7849 Intermediate Similarity NPC144133
0.7849 Intermediate Similarity NPC475855
0.7849 Intermediate Similarity NPC474232
0.7849 Intermediate Similarity NPC179394
0.7841 Intermediate Similarity NPC112868
0.7841 Intermediate Similarity NPC325031
0.7841 Intermediate Similarity NPC315731
0.7826 Intermediate Similarity NPC476803
0.7812 Intermediate Similarity NPC279621
0.7805 Intermediate Similarity NPC232812
0.7802 Intermediate Similarity NPC261721
0.7802 Intermediate Similarity NPC469910
0.7802 Intermediate Similarity NPC150755
0.7778 Intermediate Similarity NPC140591
0.7778 Intermediate Similarity NPC476804
0.7778 Intermediate Similarity NPC291500
0.7778 Intermediate Similarity NPC197835
0.7778 Intermediate Similarity NPC96259
0.7778 Intermediate Similarity NPC303653
0.7778 Intermediate Similarity NPC189609
0.7778 Intermediate Similarity NPC141193
0.7765 Intermediate Similarity NPC329852
0.7755 Intermediate Similarity NPC288876
0.7753 Intermediate Similarity NPC229825
0.7732 Intermediate Similarity NPC471462
0.7711 Intermediate Similarity NPC37929
0.7711 Intermediate Similarity NPC64234
0.7708 Intermediate Similarity NPC471142
0.7692 Intermediate Similarity NPC11804
0.7684 Intermediate Similarity NPC475302
0.7667 Intermediate Similarity NPC474809
0.7667 Intermediate Similarity NPC44261
0.766 Intermediate Similarity NPC469368
0.766 Intermediate Similarity NPC473448
0.764 Intermediate Similarity NPC78677
0.764 Intermediate Similarity NPC184208
0.764 Intermediate Similarity NPC59994
0.764 Intermediate Similarity NPC8538
0.764 Intermediate Similarity NPC474894
0.764 Intermediate Similarity NPC24417
0.7634 Intermediate Similarity NPC473658
0.7629 Intermediate Similarity NPC16967
0.7619 Intermediate Similarity NPC66108
0.7614 Intermediate Similarity NPC471537
0.7604 Intermediate Similarity NPC191521
0.7604 Intermediate Similarity NPC469632
0.7604 Intermediate Similarity NPC140543
0.76 Intermediate Similarity NPC149371
0.7579 Intermediate Similarity NPC261607
0.7579 Intermediate Similarity NPC111114
0.7579 Intermediate Similarity NPC300312
0.7579 Intermediate Similarity NPC2882
0.7553 Intermediate Similarity NPC212598
0.7553 Intermediate Similarity NPC307092
0.7549 Intermediate Similarity NPC469852
0.7549 Intermediate Similarity NPC81630
0.7527 Intermediate Similarity NPC476600
0.7527 Intermediate Similarity NPC160138
0.7526 Intermediate Similarity NPC471141
0.7526 Intermediate Similarity NPC475659
0.75 Intermediate Similarity NPC93763
0.75 Intermediate Similarity NPC38154
0.75 Intermediate Similarity NPC47880
0.75 Intermediate Similarity NPC67081
0.75 Intermediate Similarity NPC315285
0.75 Intermediate Similarity NPC471223
0.75 Intermediate Similarity NPC152778
0.75 Intermediate Similarity NPC164598
0.75 Intermediate Similarity NPC108816
0.75 Intermediate Similarity NPC472954
0.75 Intermediate Similarity NPC4299
0.75 Intermediate Similarity NPC474339
0.75 Intermediate Similarity NPC162615
0.75 Intermediate Similarity NPC315597
0.75 Intermediate Similarity NPC205034
0.75 Intermediate Similarity NPC469692
0.75 Intermediate Similarity NPC316029
0.75 Intermediate Similarity NPC165162
0.75 Intermediate Similarity NPC469645
0.7476 Intermediate Similarity NPC469853
0.7475 Intermediate Similarity NPC471144
0.7474 Intermediate Similarity NPC182136
0.7473 Intermediate Similarity NPC161045
0.7473 Intermediate Similarity NPC16488
0.7473 Intermediate Similarity NPC474193
0.7473 Intermediate Similarity NPC59097
0.7473 Intermediate Similarity NPC12283
0.7471 Intermediate Similarity NPC68819
0.7471 Intermediate Similarity NPC301525
0.7471 Intermediate Similarity NPC469880
0.7451 Intermediate Similarity NPC309190
0.7449 Intermediate Similarity NPC299396
0.7449 Intermediate Similarity NPC172998
0.7449 Intermediate Similarity NPC288350
0.7449 Intermediate Similarity NPC473859
0.7449 Intermediate Similarity NPC173329
0.7449 Intermediate Similarity NPC301596
0.7447 Intermediate Similarity NPC475902
0.7447 Intermediate Similarity NPC26078
0.7447 Intermediate Similarity NPC471956
0.7447 Intermediate Similarity NPC287089
0.7444 Intermediate Similarity NPC475944
0.7444 Intermediate Similarity NPC52861
0.7444 Intermediate Similarity NPC141810
0.7442 Intermediate Similarity NPC474758
0.7423 Intermediate Similarity NPC121825
0.7423 Intermediate Similarity NPC474338
0.7423 Intermediate Similarity NPC476267
0.7423 Intermediate Similarity NPC167219
0.7423 Intermediate Similarity NPC477241
0.7419 Intermediate Similarity NPC315395
0.7419 Intermediate Similarity NPC50637
0.7419 Intermediate Similarity NPC316426
0.7419 Intermediate Similarity NPC122502
0.7416 Intermediate Similarity NPC270126
0.7416 Intermediate Similarity NPC86971
0.7416 Intermediate Similarity NPC98557
0.7416 Intermediate Similarity NPC167881
0.7416 Intermediate Similarity NPC325869
0.7412 Intermediate Similarity NPC316185
0.7412 Intermediate Similarity NPC472254
0.74 Intermediate Similarity NPC469864
0.74 Intermediate Similarity NPC469872
0.7396 Intermediate Similarity NPC472814
0.7396 Intermediate Similarity NPC177037
0.7391 Intermediate Similarity NPC82297
0.7386 Intermediate Similarity NPC476439
0.7386 Intermediate Similarity NPC471225
0.7386 Intermediate Similarity NPC171204
0.7386 Intermediate Similarity NPC141789
0.7386 Intermediate Similarity NPC476028
0.7381 Intermediate Similarity NPC475004
0.7381 Intermediate Similarity NPC265574
0.7381 Intermediate Similarity NPC101622
0.7381 Intermediate Similarity NPC470693
0.7374 Intermediate Similarity NPC53844
0.7368 Intermediate Similarity NPC106040
0.7368 Intermediate Similarity NPC295312
0.7368 Intermediate Similarity NPC115179
0.7368 Intermediate Similarity NPC51358
0.7368 Intermediate Similarity NPC166919
0.7356 Intermediate Similarity NPC329826
0.7356 Intermediate Similarity NPC469414
0.7353 Intermediate Similarity NPC472755
0.7349 Intermediate Similarity NPC472266
0.7347 Intermediate Similarity NPC477922
0.7347 Intermediate Similarity NPC36954
0.7347 Intermediate Similarity NPC209355
0.7347 Intermediate Similarity NPC304886
0.7347 Intermediate Similarity NPC273197
0.7347 Intermediate Similarity NPC234339
0.734 Intermediate Similarity NPC72513
0.734 Intermediate Similarity NPC191283
0.7333 Intermediate Similarity NPC281132
0.7327 Intermediate Similarity NPC469657
0.7327 Intermediate Similarity NPC46998
0.7327 Intermediate Similarity NPC110443
0.7327 Intermediate Similarity NPC244456

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC260343 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
0.766 Intermediate Similarity NPD7838 Discovery
0.7129 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD4225 Approved
0.7097 Intermediate Similarity NPD7154 Phase 3
0.7041 Intermediate Similarity NPD7983 Approved
0.7 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.6989 Remote Similarity NPD5209 Approved
0.6981 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6939 Remote Similarity NPD46 Approved
0.6939 Remote Similarity NPD6698 Approved
0.6939 Remote Similarity NPD5785 Approved
0.6905 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6893 Remote Similarity NPD6648 Approved
0.6842 Remote Similarity NPD6400 Clinical (unspecified phase)
0.68 Remote Similarity NPD5778 Approved
0.68 Remote Similarity NPD5779 Approved
0.6789 Remote Similarity NPD6371 Approved
0.6774 Remote Similarity NPD4819 Approved
0.6774 Remote Similarity NPD4821 Approved
0.6774 Remote Similarity NPD4820 Approved
0.6774 Remote Similarity NPD4822 Approved
0.6774 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6771 Remote Similarity NPD5363 Approved
0.6701 Remote Similarity NPD4249 Approved
0.67 Remote Similarity NPD7637 Suspended
0.6667 Remote Similarity NPD5344 Discontinued
0.6633 Remote Similarity NPD4250 Approved
0.6633 Remote Similarity NPD4251 Approved
0.6632 Remote Similarity NPD4752 Clinical (unspecified phase)
0.663 Remote Similarity NPD4756 Discovery
0.6602 Remote Similarity NPD7839 Suspended
0.6598 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6598 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6569 Remote Similarity NPD5282 Discontinued
0.6559 Remote Similarity NPD4271 Approved
0.6559 Remote Similarity NPD4268 Approved
0.65 Remote Similarity NPD6101 Approved
0.65 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6458 Remote Similarity NPD4269 Approved
0.6458 Remote Similarity NPD4270 Approved
0.6455 Remote Similarity NPD6686 Approved
0.6392 Remote Similarity NPD5362 Discontinued
0.6373 Remote Similarity NPD6411 Approved
0.6372 Remote Similarity NPD6053 Discontinued
0.6364 Remote Similarity NPD5786 Approved
0.6354 Remote Similarity NPD5369 Approved
0.6337 Remote Similarity NPD1695 Approved
0.6327 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6293 Remote Similarity NPD7115 Discovery
0.6293 Remote Similarity NPD7505 Discontinued
0.6262 Remote Similarity NPD7640 Approved
0.6262 Remote Similarity NPD7639 Approved
0.625 Remote Similarity NPD4252 Approved
0.6224 Remote Similarity NPD6695 Phase 3
0.6224 Remote Similarity NPD5332 Approved
0.6224 Remote Similarity NPD5331 Approved
0.6218 Remote Similarity NPD7503 Approved
0.6186 Remote Similarity NPD4790 Discontinued
0.6168 Remote Similarity NPD7638 Approved
0.614 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6122 Remote Similarity NPD6435 Approved
0.61 Remote Similarity NPD1694 Approved
0.6083 Remote Similarity NPD8516 Approved
0.6083 Remote Similarity NPD8513 Phase 3
0.6083 Remote Similarity NPD8515 Approved
0.6083 Remote Similarity NPD8517 Approved
0.6064 Remote Similarity NPD8039 Approved
0.6042 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6019 Remote Similarity NPD5370 Suspended
0.598 Remote Similarity NPD7524 Approved
0.598 Remote Similarity NPD7750 Discontinued
0.5946 Remote Similarity NPD6647 Phase 2
0.5918 Remote Similarity NPD6930 Phase 2
0.5918 Remote Similarity NPD5368 Approved
0.5918 Remote Similarity NPD6931 Approved
0.5913 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5913 Remote Similarity NPD2067 Discontinued
0.5905 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5888 Remote Similarity NPD5695 Phase 3
0.5887 Remote Similarity NPD8273 Phase 1
0.5882 Remote Similarity NPD7500 Approved
0.5865 Remote Similarity NPD6051 Approved
0.5862 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5854 Remote Similarity NPD7830 Approved
0.5854 Remote Similarity NPD7829 Approved
0.5849 Remote Similarity NPD6399 Phase 3
0.5843 Remote Similarity NPD5325 Clinical (unspecified phase)
0.584 Remote Similarity NPD8074 Phase 3
0.5833 Remote Similarity NPD7327 Approved
0.5833 Remote Similarity NPD7328 Approved
0.5826 Remote Similarity NPD4061 Clinical (unspecified phase)
0.582 Remote Similarity NPD8033 Approved
0.5816 Remote Similarity NPD6929 Approved
0.5795 Remote Similarity NPD4194 Approved
0.5795 Remote Similarity NPD4191 Approved
0.5795 Remote Similarity NPD4193 Approved
0.5795 Remote Similarity NPD4192 Approved
0.5795 Remote Similarity NPD368 Approved
0.5789 Remote Similarity NPD5697 Approved
0.5789 Remote Similarity NPD6926 Approved
0.5789 Remote Similarity NPD6924 Approved
0.5785 Remote Similarity NPD7516 Approved
0.5784 Remote Similarity NPD1696 Phase 3
0.578 Remote Similarity NPD6083 Phase 2
0.578 Remote Similarity NPD6084 Phase 2
0.5758 Remote Similarity NPD7332 Phase 2
0.5758 Remote Similarity NPD7514 Phase 3
0.5755 Remote Similarity NPD5284 Approved
0.5755 Remote Similarity NPD7087 Discontinued
0.5755 Remote Similarity NPD5281 Approved
0.5748 Remote Similarity NPD7319 Approved
0.5739 Remote Similarity NPD6899 Approved
0.5739 Remote Similarity NPD6881 Approved
0.5738 Remote Similarity NPD8294 Approved
0.5738 Remote Similarity NPD8377 Approved
0.5727 Remote Similarity NPD5696 Approved
0.5726 Remote Similarity NPD6649 Approved
0.5726 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5726 Remote Similarity NPD6650 Approved
0.5714 Remote Similarity NPD7632 Discontinued
0.5714 Remote Similarity NPD7322 Clinical (unspecified phase)
0.5702 Remote Similarity NPD6402 Approved
0.5702 Remote Similarity NPD7128 Approved
0.5702 Remote Similarity NPD6675 Approved
0.5702 Remote Similarity NPD5739 Approved
0.5702 Remote Similarity NPD4211 Phase 1
0.5691 Remote Similarity NPD8296 Approved
0.5691 Remote Similarity NPD8380 Approved
0.5691 Remote Similarity NPD8378 Approved
0.5691 Remote Similarity NPD8335 Approved
0.5691 Remote Similarity NPD8379 Approved
0.569 Remote Similarity NPD6014 Approved
0.569 Remote Similarity NPD6372 Approved
0.569 Remote Similarity NPD6013 Approved
0.569 Remote Similarity NPD6373 Approved
0.569 Remote Similarity NPD6012 Approved
0.5688 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5682 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5678 Remote Similarity NPD8297 Approved
0.5678 Remote Similarity NPD6882 Approved
0.567 Remote Similarity NPD6933 Approved
0.5659 Remote Similarity NPD7260 Phase 2
0.5652 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5652 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5652 Remote Similarity NPD5701 Approved
0.5648 Remote Similarity NPD7748 Approved
0.5644 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5641 Remote Similarity NPD7290 Approved
0.5641 Remote Similarity NPD6883 Approved
0.5641 Remote Similarity NPD7102 Approved
0.5636 Remote Similarity NPD7902 Approved
0.5635 Remote Similarity NPD7507 Approved
0.5635 Remote Similarity NPD8451 Approved
0.5631 Remote Similarity NPD6893 Approved
0.5614 Remote Similarity NPD5909 Discontinued
0.5612 Remote Similarity NPD6925 Approved
0.5612 Remote Similarity NPD5776 Phase 2
0.561 Remote Similarity NPD6319 Approved
0.5607 Remote Similarity NPD5693 Phase 1
0.5603 Remote Similarity NPD6011 Approved
0.5603 Remote Similarity NPD7320 Approved
0.56 Remote Similarity NPD4695 Discontinued
0.56 Remote Similarity NPD7509 Discontinued
0.56 Remote Similarity NPD7642 Approved

Structure

External Identifiers

PubChem CID   11612119
ChEMBL   CHEMBL465358
ZINC  

Physicochemical Properties

Molecular Weight:  450.19
ALogP:  0.8686
MLogP:  3
XLogP:  2.094
# Rotatable Bonds:  14
Polar Surface Area:  125.43
# H-Bond Aceptor:  9
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  32

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