Natural Product: NPC469690

Natural Product ID:  NPC469690
Common Name:   3R*-Acetoxy-13-Keto-1R*,11S*-Dolabell-4(16),7E,12(18)-Triene
IUPAC Name:   [(3aR,5S,9E,12aS)-3a,10-dimethyl-6-methylidene-2-oxo-1-propan-2-ylidene-3,4,5,7,8,11,12,12a-octahydrocyclopenta[11]annulen-5-yl] acetate
Synonyms:  
Molecular Formula:   C22H32O3
Standard InCHIKey:  WYZJBWCWBBQHFF-YLKJAGNESA-N
Standard InCHI:  InChI=1S/C22H32O3/c1-14(2)21-18-11-10-15(3)8-7-9-16(4)20(25-17(5)23)13-22(18,6)12-19(21)24/h8,18,20H,4,7,9-13H2,1-3,5-6H3/b15-8+/t18-,20+,22+/m1/s1
Canonical SMILES:  CC(=O)O[C@H]1C[C@]2(C)CC(=O)C(=C(C)C)[C@H]2CC/C(=C/CCC1=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
NPO32701 Eunicea Genus Plexauridae Eukaryota Southwestern Caribbean PMID[20384296]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 20300 nM 18183025
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis Inhibition <= 50 % 20121165

  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 NPC469690 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
0.973 High Similarity NPC469620
0.8889 High Similarity NPC469676
0.8659 High Similarity NPC261253
0.8659 High Similarity NPC474045
0.859 High Similarity NPC471220
0.8588 High Similarity NPC221282
0.8434 Intermediate Similarity NPC220478
0.8375 Intermediate Similarity NPC47747
0.8354 Intermediate Similarity NPC128276
0.8333 Intermediate Similarity NPC469646
0.8313 Intermediate Similarity NPC161957
0.8312 Intermediate Similarity NPC469691
0.8312 Intermediate Similarity NPC167049
0.8293 Intermediate Similarity NPC475622
0.8293 Intermediate Similarity NPC193198
0.8293 Intermediate Similarity NPC108045
0.8272 Intermediate Similarity NPC471325
0.8228 Intermediate Similarity NPC57744
0.8193 Intermediate Similarity NPC475100
0.8193 Intermediate Similarity NPC149869
0.8193 Intermediate Similarity NPC238197
0.8161 Intermediate Similarity NPC290651
0.8148 Intermediate Similarity NPC290508
0.8148 Intermediate Similarity NPC73052
0.8148 Intermediate Similarity NPC293418
0.8125 Intermediate Similarity NPC299235
0.8101 Intermediate Similarity NPC226242
0.8101 Intermediate Similarity NPC27205
0.8072 Intermediate Similarity NPC39588
0.8072 Intermediate Similarity NPC54468
0.8049 Intermediate Similarity NPC35089
0.8049 Intermediate Similarity NPC10276
0.8046 Intermediate Similarity NPC253144
0.8046 Intermediate Similarity NPC471818
0.8025 Intermediate Similarity NPC182550
0.8025 Intermediate Similarity NPC178277
0.8025 Intermediate Similarity NPC471299
0.8 Intermediate Similarity NPC195640
0.8 Intermediate Similarity NPC472266
0.8 Intermediate Similarity NPC122264
0.7978 Intermediate Similarity NPC148463
0.7976 Intermediate Similarity NPC474359
0.7975 Intermediate Similarity NPC244166
0.7975 Intermediate Similarity NPC155587
0.7975 Intermediate Similarity NPC226669
0.7975 Intermediate Similarity NPC138408
0.7975 Intermediate Similarity NPC469678
0.7975 Intermediate Similarity NPC193351
0.7975 Intermediate Similarity NPC469669
0.7975 Intermediate Similarity NPC475771
0.7975 Intermediate Similarity NPC474011
0.7955 Intermediate Similarity NPC123177
0.7955 Intermediate Similarity NPC150978
0.7955 Intermediate Similarity NPC74103
0.7955 Intermediate Similarity NPC472953
0.7955 Intermediate Similarity NPC70595
0.7955 Intermediate Similarity NPC218301
0.7955 Intermediate Similarity NPC284185
0.7952 Intermediate Similarity NPC35556
0.7952 Intermediate Similarity NPC173609
0.7949 Intermediate Similarity NPC92909
0.7949 Intermediate Similarity NPC470237
0.7949 Intermediate Similarity NPC107783
0.7927 Intermediate Similarity NPC74673
0.7927 Intermediate Similarity NPC223904
0.7927 Intermediate Similarity NPC302426
0.7927 Intermediate Similarity NPC69271
0.7922 Intermediate Similarity NPC469660
0.7907 Intermediate Similarity NPC478144
0.7901 Intermediate Similarity NPC222210
0.7901 Intermediate Similarity NPC472960
0.7901 Intermediate Similarity NPC253749
0.7901 Intermediate Similarity NPC474056
0.7901 Intermediate Similarity NPC63445
0.7895 Intermediate Similarity NPC469688
0.7889 Intermediate Similarity NPC470974
0.7889 Intermediate Similarity NPC470978
0.7889 Intermediate Similarity NPC474490
0.7882 Intermediate Similarity NPC33570
0.7882 Intermediate Similarity NPC78089
0.7882 Intermediate Similarity NPC323765
0.7882 Intermediate Similarity NPC189311
0.7882 Intermediate Similarity NPC110405
0.7882 Intermediate Similarity NPC21471
0.7875 Intermediate Similarity NPC40353
0.7875 Intermediate Similarity NPC472959
0.7865 Intermediate Similarity NPC202824
0.7865 Intermediate Similarity NPC477361
0.7857 Intermediate Similarity NPC170377
0.7857 Intermediate Similarity NPC215294
0.7849 Intermediate Similarity NPC310981
0.7848 Intermediate Similarity NPC476355
0.7848 Intermediate Similarity NPC294434
0.7848 Intermediate Similarity NPC117746
0.7848 Intermediate Similarity NPC140287
0.7848 Intermediate Similarity NPC259599
0.7848 Intermediate Similarity NPC15499
0.7848 Intermediate Similarity NPC474758
0.7841 Intermediate Similarity NPC152467
0.7831 Intermediate Similarity NPC42470
0.7826 Intermediate Similarity NPC176845
0.7821 Intermediate Similarity NPC163003
0.7821 Intermediate Similarity NPC129665
0.7805 Intermediate Similarity NPC63649
0.7805 Intermediate Similarity NPC264227
0.7805 Intermediate Similarity NPC472965
0.7792 Intermediate Similarity NPC22301
0.7792 Intermediate Similarity NPC469677
0.7792 Intermediate Similarity NPC144511
0.7792 Intermediate Similarity NPC296522
0.7791 Intermediate Similarity NPC107787
0.7791 Intermediate Similarity NPC238593
0.7778 Intermediate Similarity NPC208223
0.7778 Intermediate Similarity NPC470240
0.7778 Intermediate Similarity NPC41780
0.7778 Intermediate Similarity NPC15975
0.7778 Intermediate Similarity NPC187568
0.7778 Intermediate Similarity NPC195785
0.7778 Intermediate Similarity NPC65603
0.7778 Intermediate Similarity NPC476794
0.7765 Intermediate Similarity NPC115786
0.7753 Intermediate Similarity NPC472705
0.7753 Intermediate Similarity NPC219874
0.775 Intermediate Similarity NPC216791
0.7738 Intermediate Similarity NPC200513
0.7727 Intermediate Similarity NPC284561
0.7722 Intermediate Similarity NPC135703
0.7717 Intermediate Similarity NPC69385
0.7717 Intermediate Similarity NPC110937
0.7711 Intermediate Similarity NPC304795
0.7711 Intermediate Similarity NPC233377
0.7711 Intermediate Similarity NPC276356
0.7711 Intermediate Similarity NPC6823
0.7711 Intermediate Similarity NPC474510
0.7701 Intermediate Similarity NPC478145
0.7701 Intermediate Similarity NPC312561
0.7692 Intermediate Similarity NPC476488
0.7692 Intermediate Similarity NPC473369
0.7692 Intermediate Similarity NPC33473
0.7692 Intermediate Similarity NPC476487
0.7684 Intermediate Similarity NPC470954
0.7683 Intermediate Similarity NPC474341
0.7674 Intermediate Similarity NPC197903
0.7674 Intermediate Similarity NPC99395
0.7674 Intermediate Similarity NPC474547
0.7674 Intermediate Similarity NPC177932
0.7667 Intermediate Similarity NPC476598
0.7667 Intermediate Similarity NPC476597
0.7662 Intermediate Similarity NPC218477
0.766 Intermediate Similarity NPC477950
0.7654 Intermediate Similarity NPC279537
0.7654 Intermediate Similarity NPC473223
0.7654 Intermediate Similarity NPC266159
0.7654 Intermediate Similarity NPC472967
0.7654 Intermediate Similarity NPC235906
0.7654 Intermediate Similarity NPC123360
0.7647 Intermediate Similarity NPC470046
0.7647 Intermediate Similarity NPC53867
0.7647 Intermediate Similarity NPC222358
0.7647 Intermediate Similarity NPC470047
0.7647 Intermediate Similarity NPC475947
0.7647 Intermediate Similarity NPC272814
0.764 Intermediate Similarity NPC8062
0.764 Intermediate Similarity NPC161638
0.764 Intermediate Similarity NPC475965
0.764 Intermediate Similarity NPC49946
0.764 Intermediate Similarity NPC474842
0.764 Intermediate Similarity NPC306168
0.7634 Intermediate Similarity NPC252295
0.7634 Intermediate Similarity NPC470188
0.7634 Intermediate Similarity NPC471932
0.7634 Intermediate Similarity NPC222011
0.7632 Intermediate Similarity NPC304665
0.7632 Intermediate Similarity NPC126899
0.7632 Intermediate Similarity NPC154728
0.7625 Intermediate Similarity NPC469643
0.7625 Intermediate Similarity NPC469641
0.7619 Intermediate Similarity NPC475665
0.7619 Intermediate Similarity NPC301477
0.7619 Intermediate Similarity NPC281949
0.7619 Intermediate Similarity NPC25684
0.7619 Intermediate Similarity NPC325031
0.7619 Intermediate Similarity NPC255580
0.7619 Intermediate Similarity NPC39411
0.7614 Intermediate Similarity NPC469653
0.7614 Intermediate Similarity NPC469631
0.7614 Intermediate Similarity NPC471047
0.7614 Intermediate Similarity NPC469628
0.7614 Intermediate Similarity NPC215831
0.7614 Intermediate Similarity NPC475906
0.7614 Intermediate Similarity NPC226863
0.7609 Intermediate Similarity NPC185553
0.7609 Intermediate Similarity NPC477354
0.7609 Intermediate Similarity NPC111684
0.7609 Intermediate Similarity NPC58052
0.7595 Intermediate Similarity NPC84038
0.7595 Intermediate Similarity NPC257618
0.759 Intermediate Similarity NPC150646
0.759 Intermediate Similarity NPC270126
0.759 Intermediate Similarity NPC617

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC469690 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
0.8 Intermediate Similarity NPD5330 Approved
0.8 Intermediate Similarity NPD6409 Approved
0.8 Intermediate Similarity NPD7146 Approved
0.8 Intermediate Similarity NPD7334 Approved
0.8 Intermediate Similarity NPD6684 Approved
0.8 Intermediate Similarity NPD7521 Approved
0.7841 Intermediate Similarity NPD5785 Approved
0.7816 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD6903 Approved
0.7738 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD6435 Approved
0.7683 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD1694 Approved
0.7614 Intermediate Similarity NPD6672 Approved
0.7614 Intermediate Similarity NPD5737 Approved
0.7531 Intermediate Similarity NPD8039 Approved
0.7529 Intermediate Similarity NPD5209 Approved
0.75 Intermediate Similarity NPD5368 Approved
0.75 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD5786 Approved
0.7363 Intermediate Similarity NPD5693 Phase 1
0.7273 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD5363 Approved
0.7273 Intermediate Similarity NPD2685 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD5362 Discontinued
0.7209 Intermediate Similarity NPD5369 Approved
0.7143 Intermediate Similarity NPD5328 Approved
0.7143 Intermediate Similarity NPD6080 Approved
0.7143 Intermediate Similarity NPD6904 Approved
0.7143 Intermediate Similarity NPD6673 Approved
0.7126 Intermediate Similarity NPD4269 Approved
0.7126 Intermediate Similarity NPD4270 Approved
0.7097 Intermediate Similarity NPD6399 Phase 3
0.7083 Intermediate Similarity NPD7638 Approved
0.7079 Intermediate Similarity NPD6082 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD7154 Phase 3
0.7033 Intermediate Similarity NPD5208 Approved
0.701 Intermediate Similarity NPD7639 Approved
0.701 Intermediate Similarity NPD7640 Approved
0.7 Intermediate Similarity NPD6098 Approved
0.7 Intermediate Similarity NPD5739 Approved
0.7 Intermediate Similarity NPD7128 Approved
0.7 Intermediate Similarity NPD6402 Approved
0.7 Intermediate Similarity NPD6675 Approved
0.6989 Remote Similarity NPD6079 Approved
0.6989 Remote Similarity NPD6050 Approved
0.6979 Remote Similarity NPD6083 Phase 2
0.6979 Remote Similarity NPD6084 Phase 2
0.6966 Remote Similarity NPD3665 Phase 1
0.6966 Remote Similarity NPD3666 Approved
0.6966 Remote Similarity NPD3133 Approved
0.6962 Remote Similarity NPD7331 Phase 2
0.6957 Remote Similarity NPD1695 Approved
0.6947 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6947 Remote Similarity NPD5695 Phase 3
0.6923 Remote Similarity NPD3573 Approved
0.6897 Remote Similarity NPD4252 Approved
0.6897 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6882 Remote Similarity NPD5207 Approved
0.6882 Remote Similarity NPD5692 Phase 3
0.6882 Remote Similarity NPD46 Approved
0.6882 Remote Similarity NPD6698 Approved
0.6863 Remote Similarity NPD6881 Approved
0.6863 Remote Similarity NPD6899 Approved
0.6863 Remote Similarity NPD7320 Approved
0.6842 Remote Similarity NPD7748 Approved
0.6842 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6842 Remote Similarity NPD7900 Approved
0.6832 Remote Similarity NPD6008 Approved
0.6813 Remote Similarity NPD3618 Phase 1
0.6813 Remote Similarity NPD5279 Phase 3
0.6809 Remote Similarity NPD6411 Approved
0.6809 Remote Similarity NPD5694 Approved
0.6796 Remote Similarity NPD6373 Approved
0.6796 Remote Similarity NPD6372 Approved
0.6778 Remote Similarity NPD4786 Approved
0.6774 Remote Similarity NPD6051 Approved
0.6765 Remote Similarity NPD5697 Approved
0.6765 Remote Similarity NPD5701 Approved
0.6742 Remote Similarity NPD3667 Approved
0.6735 Remote Similarity NPD5696 Approved
0.6731 Remote Similarity NPD7102 Approved
0.6731 Remote Similarity NPD6883 Approved
0.6731 Remote Similarity NPD7290 Approved
0.6707 Remote Similarity NPD4137 Phase 3
0.6705 Remote Similarity NPD4820 Approved
0.6705 Remote Similarity NPD4821 Approved
0.6705 Remote Similarity NPD4822 Approved
0.6705 Remote Similarity NPD4819 Approved
0.6699 Remote Similarity NPD6011 Approved
0.6667 Remote Similarity NPD5332 Approved
0.6667 Remote Similarity NPD6001 Approved
0.6667 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4271 Approved
0.6667 Remote Similarity NPD6649 Approved
0.6667 Remote Similarity NPD6650 Approved
0.6667 Remote Similarity NPD5331 Approved
0.6667 Remote Similarity NPD6847 Approved
0.6667 Remote Similarity NPD6617 Approved
0.6667 Remote Similarity NPD6869 Approved
0.6667 Remote Similarity NPD4268 Approved
0.6667 Remote Similarity NPD8130 Phase 1
0.6635 Remote Similarity NPD6013 Approved
0.6635 Remote Similarity NPD6014 Approved
0.6635 Remote Similarity NPD6012 Approved
0.6633 Remote Similarity NPD7902 Approved
0.6632 Remote Similarity NPD7515 Phase 2
0.6629 Remote Similarity NPD4790 Discontinued
0.6627 Remote Similarity NPD4691 Approved
0.6627 Remote Similarity NPD4747 Approved
0.6625 Remote Similarity NPD7341 Phase 2
0.6604 Remote Similarity NPD8297 Approved
0.6604 Remote Similarity NPD6882 Approved
0.6604 Remote Similarity NPD6053 Discontinued
0.6596 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6596 Remote Similarity NPD6101 Approved
0.6593 Remote Similarity NPD3668 Phase 3
0.6588 Remote Similarity NPD5733 Approved
0.6571 Remote Similarity NPD6371 Approved
0.6562 Remote Similarity NPD5778 Approved
0.6562 Remote Similarity NPD5779 Approved
0.6556 Remote Similarity NPD4223 Phase 3
0.6556 Remote Similarity NPD4221 Approved
0.6548 Remote Similarity NPD5276 Approved
0.6538 Remote Similarity NPD6686 Approved
0.6531 Remote Similarity NPD4697 Phase 3
0.6531 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6531 Remote Similarity NPD5222 Approved
0.6531 Remote Similarity NPD5221 Approved
0.6522 Remote Similarity NPD5329 Approved
0.6514 Remote Similarity NPD7115 Discovery
0.65 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6465 Remote Similarity NPD5173 Approved
0.6465 Remote Similarity NPD4755 Approved
0.6458 Remote Similarity NPD5281 Approved
0.6458 Remote Similarity NPD5284 Approved
0.6458 Remote Similarity NPD7637 Suspended
0.6458 Remote Similarity NPD7983 Approved
0.6452 Remote Similarity NPD6422 Discontinued
0.6442 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6429 Remote Similarity NPD5654 Approved
0.6422 Remote Similarity NPD6868 Approved
0.6421 Remote Similarity NPD4753 Phase 2
0.6413 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6413 Remote Similarity NPD4197 Approved
0.64 Remote Similarity NPD4225 Approved
0.6395 Remote Similarity NPD4687 Approved
0.6395 Remote Similarity NPD4058 Approved
0.6392 Remote Similarity NPD4202 Approved
0.6383 Remote Similarity NPD4250 Approved
0.6383 Remote Similarity NPD4251 Approved
0.6373 Remote Similarity NPD5211 Phase 2
0.6373 Remote Similarity NPD7632 Discontinued
0.6353 Remote Similarity NPD5777 Approved
0.6344 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6337 Remote Similarity NPD4696 Approved
0.6337 Remote Similarity NPD5285 Approved
0.6337 Remote Similarity NPD5286 Approved
0.6337 Remote Similarity NPD4700 Approved
0.6327 Remote Similarity NPD5282 Discontinued
0.6311 Remote Similarity NPD6052 Approved
0.6306 Remote Similarity NPD6335 Approved
0.63 Remote Similarity NPD5959 Approved
0.6292 Remote Similarity NPD3617 Approved
0.6289 Remote Similarity NPD8035 Phase 2
0.6289 Remote Similarity NPD8034 Phase 2
0.6286 Remote Similarity NPD6412 Phase 2
0.6277 Remote Similarity NPD4690 Approved
0.6277 Remote Similarity NPD5280 Approved
0.6277 Remote Similarity NPD4688 Approved
0.6277 Remote Similarity NPD4693 Phase 3
0.6277 Remote Similarity NPD4249 Approved
0.6277 Remote Similarity NPD5205 Approved
0.6277 Remote Similarity NPD4694 Approved
0.6277 Remote Similarity NPD4689 Approved
0.6277 Remote Similarity NPD4138 Approved
0.6277 Remote Similarity NPD5690 Phase 2
0.6275 Remote Similarity NPD5223 Approved
0.6273 Remote Similarity NPD6274 Approved
0.625 Remote Similarity NPD7100 Approved
0.625 Remote Similarity NPD5141 Approved
0.625 Remote Similarity NPD7101 Approved
0.6239 Remote Similarity NPD6858 Approved
0.6239 Remote Similarity NPD7094 Approved
0.6239 Remote Similarity NPD4632 Approved
0.6216 Remote Similarity NPD6927 Phase 3
0.6216 Remote Similarity NPD29 Approved
0.6216 Remote Similarity NPD6317 Approved
0.6216 Remote Similarity NPD28 Approved
0.6214 Remote Similarity NPD5225 Approved
0.6214 Remote Similarity NPD5226 Approved
0.6214 Remote Similarity NPD5224 Approved
0.6214 Remote Similarity NPD4633 Approved
0.6207 Remote Similarity NPD7507 Approved
0.6203 Remote Similarity NPD3198 Approved
0.62 Remote Similarity NPD7732 Phase 3
0.62 Remote Similarity NPD7839 Suspended
0.619 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6186 Remote Similarity NPD7838 Discovery
0.6161 Remote Similarity NPD6313 Approved

Structure

External Identifiers

PubChem CID   46833125
ChEMBL   CHEMBL1099120
ZINC  

Physicochemical Properties

Molecular Weight:  344.24
ALogP:  3.2658
MLogP:  3.55
XLogP:  4.368
# Rotatable Bonds:  7
Polar Surface Area:  43.37
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  25

Download Data

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