Natural Product: NPC469688

Natural Product ID:  NPC469688
Common Name:   7R*-Hydroperoxy-13-Keto-1R*,11S*-Dolabell-3E,8E,12(18)-Triene
IUPAC Name:   (3aR,5E,9R,10E,12aS)-9-hydroperoxy-3a,6,10-trimethyl-1-propan-2-ylidene-4,7,8,9,12,12a-hexahydro-3H-cyclopenta[11]annulen-2-one
Synonyms:  
Molecular Formula:   C20H30O3
Standard InCHIKey:  XIWBBVNJGMKOMD-CBDHSLHVSA-N
Standard InCHI:  InChI=1S/C20H30O3/c1-13(2)19-16-8-7-15(4)18(23-22)9-6-14(3)10-11-20(16,5)12-17(19)21/h7,10,16,18,22H,6,8-9,11-12H2,1-5H3/b14-10+,15-7+/t16-,18-,20-/m1/s1
Canonical SMILES:  OO[C@@H]1CC/C(=C/C[C@]2([C@H](C/C=C/1C)C(=C(C)C)C(=O)C2)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 = 36400 nM 17125236
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis Inhibition <= 50 % 17708655

  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 NPC469688 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
0.9385 High Similarity NPC469679
0.9242 High Similarity NPC469677
0.8472 Intermediate Similarity NPC469646
0.8438 Intermediate Similarity NPC259261
0.8281 Intermediate Similarity NPC266295
0.8281 Intermediate Similarity NPC94991
0.8194 Intermediate Similarity NPC167049
0.8194 Intermediate Similarity NPC469691
0.8082 Intermediate Similarity NPC216791
0.8082 Intermediate Similarity NPC474011
0.803 Intermediate Similarity NPC25853
0.7941 Intermediate Similarity NPC473902
0.7895 Intermediate Similarity NPC469690
0.7846 Intermediate Similarity NPC49575
0.7846 Intermediate Similarity NPC267626
0.7846 Intermediate Similarity NPC55004
0.7846 Intermediate Similarity NPC230823
0.7838 Intermediate Similarity NPC469678
0.7838 Intermediate Similarity NPC475771
0.7838 Intermediate Similarity NPC469669
0.7808 Intermediate Similarity NPC107783
0.7808 Intermediate Similarity NPC92909
0.7763 Intermediate Similarity NPC475994
0.7727 Intermediate Similarity NPC30215
0.7692 Intermediate Similarity NPC136150
0.7681 Intermediate Similarity NPC212210
0.7671 Intermediate Similarity NPC474884
0.7662 Intermediate Similarity NPC469620
0.7662 Intermediate Similarity NPC229204
0.7647 Intermediate Similarity NPC260573
0.7647 Intermediate Similarity NPC97322
0.7647 Intermediate Similarity NPC475795
0.7639 Intermediate Similarity NPC61702
0.7639 Intermediate Similarity NPC162867
0.7632 Intermediate Similarity NPC86917
0.7632 Intermediate Similarity NPC276769
0.7625 Intermediate Similarity NPC230527
0.7625 Intermediate Similarity NPC7927
0.76 Intermediate Similarity NPC251435
0.7571 Intermediate Similarity NPC474329
0.7571 Intermediate Similarity NPC474304
0.7568 Intermediate Similarity NPC186042
0.7564 Intermediate Similarity NPC45495
0.7561 Intermediate Similarity NPC287079
0.7536 Intermediate Similarity NPC32285
0.7536 Intermediate Similarity NPC165695
0.7534 Intermediate Similarity NPC286154
0.75 Intermediate Similarity NPC226242
0.75 Intermediate Similarity NPC215481
0.75 Intermediate Similarity NPC279537
0.7439 Intermediate Similarity NPC474045
0.7439 Intermediate Similarity NPC261253
0.7436 Intermediate Similarity NPC308038
0.7436 Intermediate Similarity NPC181195
0.7436 Intermediate Similarity NPC261125
0.7436 Intermediate Similarity NPC7232
0.7412 Intermediate Similarity NPC473998
0.7407 Intermediate Similarity NPC85774
0.7407 Intermediate Similarity NPC214043
0.7407 Intermediate Similarity NPC321187
0.7407 Intermediate Similarity NPC161423
0.7407 Intermediate Similarity NPC227064
0.7407 Intermediate Similarity NPC58841
0.7407 Intermediate Similarity NPC473246
0.7407 Intermediate Similarity NPC329043
0.7397 Intermediate Similarity NPC139397
0.7391 Intermediate Similarity NPC213152
0.7381 Intermediate Similarity NPC123912
0.7381 Intermediate Similarity NPC473999
0.7381 Intermediate Similarity NPC170775
0.7381 Intermediate Similarity NPC309603
0.7375 Intermediate Similarity NPC279186
0.7375 Intermediate Similarity NPC256750
0.7375 Intermediate Similarity NPC20262
0.7375 Intermediate Similarity NPC145963
0.7368 Intermediate Similarity NPC77501
0.7368 Intermediate Similarity NPC114236
0.7368 Intermediate Similarity NPC474885
0.7361 Intermediate Similarity NPC106613
0.7361 Intermediate Similarity NPC269985
0.7361 Intermediate Similarity NPC475523
0.7333 Intermediate Similarity NPC275098
0.7333 Intermediate Similarity NPC201562
0.7333 Intermediate Similarity NPC323437
0.7333 Intermediate Similarity NPC29542
0.7317 Intermediate Similarity NPC474853
0.7317 Intermediate Similarity NPC474083
0.7317 Intermediate Similarity NPC470574
0.7317 Intermediate Similarity NPC179006
0.7317 Intermediate Similarity NPC471224
0.7308 Intermediate Similarity NPC253749
0.7308 Intermediate Similarity NPC192006
0.7308 Intermediate Similarity NPC474056
0.7308 Intermediate Similarity NPC128276
0.7308 Intermediate Similarity NPC471220
0.7308 Intermediate Similarity NPC478122
0.7297 Intermediate Similarity NPC2634
0.7297 Intermediate Similarity NPC251929
0.7297 Intermediate Similarity NPC265782
0.7297 Intermediate Similarity NPC260040
0.7297 Intermediate Similarity NPC307176
0.7294 Intermediate Similarity NPC48010
0.7284 Intermediate Similarity NPC193198
0.7284 Intermediate Similarity NPC108045
0.7284 Intermediate Similarity NPC41539
0.7284 Intermediate Similarity NPC470047
0.7284 Intermediate Similarity NPC475622
0.7284 Intermediate Similarity NPC470046
0.7273 Intermediate Similarity NPC27205
0.7273 Intermediate Similarity NPC469796
0.7273 Intermediate Similarity NPC469793
0.7273 Intermediate Similarity NPC263582
0.726 Intermediate Similarity NPC155198
0.7241 Intermediate Similarity NPC8993
0.7237 Intermediate Similarity NPC294434
0.7237 Intermediate Similarity NPC206875
0.7237 Intermediate Similarity NPC215050
0.7237 Intermediate Similarity NPC15499
0.7237 Intermediate Similarity NPC117746
0.7237 Intermediate Similarity NPC259599
0.7231 Intermediate Similarity NPC474141
0.7231 Intermediate Similarity NPC296311
0.7229 Intermediate Similarity NPC474732
0.7229 Intermediate Similarity NPC194417
0.7229 Intermediate Similarity NPC145879
0.7229 Intermediate Similarity NPC222613
0.7229 Intermediate Similarity NPC475022
0.7229 Intermediate Similarity NPC474778
0.7229 Intermediate Similarity NPC118648
0.7229 Intermediate Similarity NPC474733
0.7229 Intermediate Similarity NPC327115
0.7229 Intermediate Similarity NPC31564
0.7215 Intermediate Similarity NPC471299
0.7215 Intermediate Similarity NPC19900
0.7209 Intermediate Similarity NPC475806
0.72 Intermediate Similarity NPC181204
0.72 Intermediate Similarity NPC67076
0.72 Intermediate Similarity NPC54123
0.72 Intermediate Similarity NPC319163
0.72 Intermediate Similarity NPC133253
0.7195 Intermediate Similarity NPC237712
0.7195 Intermediate Similarity NPC475100
0.7195 Intermediate Similarity NPC238197
0.7179 Intermediate Similarity NPC476007
0.7179 Intermediate Similarity NPC197659
0.7179 Intermediate Similarity NPC203403
0.7179 Intermediate Similarity NPC74995
0.7179 Intermediate Similarity NPC211279
0.7179 Intermediate Similarity NPC57744
0.7176 Intermediate Similarity NPC477215
0.7176 Intermediate Similarity NPC476388
0.7176 Intermediate Similarity NPC214387
0.7164 Intermediate Similarity NPC20603
0.7162 Intermediate Similarity NPC477448
0.7162 Intermediate Similarity NPC10758
0.7162 Intermediate Similarity NPC477449
0.7162 Intermediate Similarity NPC250928
0.716 Intermediate Similarity NPC93590
0.716 Intermediate Similarity NPC151519
0.716 Intermediate Similarity NPC133844
0.7143 Intermediate Similarity NPC263698
0.7143 Intermediate Similarity NPC136548
0.7143 Intermediate Similarity NPC141292
0.7143 Intermediate Similarity NPC329852
0.7143 Intermediate Similarity NPC58063
0.7143 Intermediate Similarity NPC317590
0.7143 Intermediate Similarity NPC294304
0.7143 Intermediate Similarity NPC475740
0.7143 Intermediate Similarity NPC228574
0.7126 Intermediate Similarity NPC472930
0.7126 Intermediate Similarity NPC474736
0.7126 Intermediate Similarity NPC37816
0.7126 Intermediate Similarity NPC69454
0.7126 Intermediate Similarity NPC109305
0.7125 Intermediate Similarity NPC172013
0.7125 Intermediate Similarity NPC472478
0.7125 Intermediate Similarity NPC471514
0.7123 Intermediate Similarity NPC477791
0.7108 Intermediate Similarity NPC469948
0.7108 Intermediate Similarity NPC470048
0.7108 Intermediate Similarity NPC472931
0.7108 Intermediate Similarity NPC476426
0.7108 Intermediate Similarity NPC472940
0.7108 Intermediate Similarity NPC323765
0.7105 Intermediate Similarity NPC130016
0.7105 Intermediate Similarity NPC303613
0.7105 Intermediate Similarity NPC56747
0.7105 Intermediate Similarity NPC109576
0.7105 Intermediate Similarity NPC300940
0.7105 Intermediate Similarity NPC474228
0.7105 Intermediate Similarity NPC180015
0.7101 Intermediate Similarity NPC143834
0.7101 Intermediate Similarity NPC285594
0.7101 Intermediate Similarity NPC96551
0.7093 Intermediate Similarity NPC49946
0.7093 Intermediate Similarity NPC477149
0.7093 Intermediate Similarity NPC320026
0.7093 Intermediate Similarity NPC477147
0.7093 Intermediate Similarity NPC306168
0.7089 Intermediate Similarity NPC82635

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC469688 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
0.7763 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD3133 Approved
0.7407 Intermediate Similarity NPD3665 Phase 1
0.7407 Intermediate Similarity NPD3666 Approved
0.7397 Intermediate Similarity NPD4137 Phase 3
0.7297 Intermediate Similarity NPD4747 Approved
0.7297 Intermediate Similarity NPD4691 Approved
0.7229 Intermediate Similarity NPD5279 Phase 3
0.7229 Intermediate Similarity NPD3618 Phase 1
0.72 Intermediate Similarity NPD5276 Approved
0.716 Intermediate Similarity NPD3667 Approved
0.7108 Intermediate Similarity NPD5363 Approved
0.7093 Intermediate Similarity NPD5785 Approved
0.7024 Intermediate Similarity NPD7521 Approved
0.7024 Intermediate Similarity NPD7334 Approved
0.7024 Intermediate Similarity NPD5330 Approved
0.7024 Intermediate Similarity NPD6409 Approved
0.7024 Intermediate Similarity NPD6684 Approved
0.7024 Intermediate Similarity NPD7146 Approved
0.7013 Intermediate Similarity NPD5733 Approved
0.7013 Intermediate Similarity NPD4058 Approved
0.7013 Intermediate Similarity NPD4687 Approved
0.6988 Remote Similarity NPD4786 Approved
0.6988 Remote Similarity NPD3668 Phase 3
0.6977 Remote Similarity NPD5328 Approved
0.6951 Remote Similarity NPD4269 Approved
0.6951 Remote Similarity NPD4270 Approved
0.6951 Remote Similarity NPD4221 Approved
0.6951 Remote Similarity NPD4223 Phase 3
0.6951 Remote Similarity NPD5209 Approved
0.6914 Remote Similarity NPD4252 Approved
0.6867 Remote Similarity NPD5362 Discontinued
0.686 Remote Similarity NPD7513 Clinical (unspecified phase)
0.686 Remote Similarity NPD6903 Approved
0.6818 Remote Similarity NPD6079 Approved
0.68 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6786 Remote Similarity NPD4197 Approved
0.6782 Remote Similarity NPD4753 Phase 2
0.6757 Remote Similarity NPD7331 Phase 2
0.6747 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6742 Remote Similarity NPD4202 Approved
0.6714 Remote Similarity NPD287 Approved
0.6707 Remote Similarity NPD4820 Approved
0.6707 Remote Similarity NPD4821 Approved
0.6707 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6707 Remote Similarity NPD4819 Approved
0.6707 Remote Similarity NPD5368 Approved
0.6707 Remote Similarity NPD4822 Approved
0.6706 Remote Similarity NPD5329 Approved
0.6706 Remote Similarity NPD1694 Approved
0.6667 Remote Similarity NPD5331 Approved
0.6667 Remote Similarity NPD3617 Approved
0.6667 Remote Similarity NPD4271 Approved
0.6667 Remote Similarity NPD5737 Approved
0.6667 Remote Similarity NPD5332 Approved
0.6667 Remote Similarity NPD4268 Approved
0.6667 Remote Similarity NPD6672 Approved
0.6628 Remote Similarity NPD4138 Approved
0.6628 Remote Similarity NPD4519 Discontinued
0.6628 Remote Similarity NPD5205 Approved
0.6628 Remote Similarity NPD4689 Approved
0.6628 Remote Similarity NPD5280 Approved
0.6628 Remote Similarity NPD4693 Phase 3
0.6628 Remote Similarity NPD4694 Approved
0.6628 Remote Similarity NPD4690 Approved
0.6628 Remote Similarity NPD5690 Phase 2
0.6628 Remote Similarity NPD4623 Approved
0.6628 Remote Similarity NPD5786 Approved
0.6628 Remote Similarity NPD4688 Approved
0.6627 Remote Similarity NPD5369 Approved
0.6627 Remote Similarity NPD4790 Discontinued
0.6622 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6548 Remote Similarity NPD6435 Approved
0.6522 Remote Similarity NPD5221 Approved
0.6522 Remote Similarity NPD4697 Phase 3
0.6522 Remote Similarity NPD5222 Approved
0.6522 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6506 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6506 Remote Similarity NPD4695 Discontinued
0.6494 Remote Similarity NPD6923 Approved
0.6494 Remote Similarity NPD6922 Approved
0.6477 Remote Similarity NPD4518 Approved
0.6471 Remote Similarity NPD7154 Phase 3
0.6452 Remote Similarity NPD5173 Approved
0.6452 Remote Similarity NPD4755 Approved
0.6437 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6413 Remote Similarity NPD5695 Phase 3
0.6413 Remote Similarity NPD5210 Approved
0.6413 Remote Similarity NPD4629 Approved
0.641 Remote Similarity NPD7143 Approved
0.641 Remote Similarity NPD7144 Approved
0.64 Remote Similarity NPD7341 Phase 2
0.6386 Remote Similarity NPD4195 Approved
0.6383 Remote Similarity NPD7638 Approved
0.6375 Remote Similarity NPD6926 Approved
0.6375 Remote Similarity NPD6924 Approved
0.6374 Remote Similarity NPD6399 Phase 3
0.6354 Remote Similarity NPD5211 Phase 2
0.6341 Remote Similarity NPD5776 Phase 2
0.6341 Remote Similarity NPD6925 Approved
0.6333 Remote Similarity NPD4096 Approved
0.6329 Remote Similarity NPD7151 Approved
0.6329 Remote Similarity NPD7152 Approved
0.6329 Remote Similarity NPD7150 Approved
0.6322 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6322 Remote Similarity NPD1696 Phase 3
0.6316 Remote Similarity NPD4700 Approved
0.6316 Remote Similarity NPD4696 Approved
0.6316 Remote Similarity NPD7640 Approved
0.6316 Remote Similarity NPD5285 Approved
0.6316 Remote Similarity NPD7639 Approved
0.6316 Remote Similarity NPD5286 Approved
0.631 Remote Similarity NPD7514 Phase 3
0.6304 Remote Similarity NPD5282 Discontinued
0.6296 Remote Similarity NPD8039 Approved
0.6292 Remote Similarity NPD5208 Approved
0.6279 Remote Similarity NPD3527 Clinical (unspecified phase)
0.6279 Remote Similarity NPD4788 Approved
0.6277 Remote Similarity NPD6084 Phase 2
0.6277 Remote Similarity NPD6083 Phase 2
0.6265 Remote Similarity NPD7145 Approved
0.6265 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6264 Remote Similarity NPD5281 Approved
0.6264 Remote Similarity NPD5693 Phase 1
0.6264 Remote Similarity NPD7515 Phase 2
0.6264 Remote Similarity NPD5284 Approved
0.6264 Remote Similarity NPD7637 Suspended
0.625 Remote Similarity NPD5223 Approved
0.6237 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6235 Remote Similarity NPD6902 Approved
0.6224 Remote Similarity NPD5141 Approved
0.6222 Remote Similarity NPD6904 Approved
0.6222 Remote Similarity NPD6673 Approved
0.6222 Remote Similarity NPD6080 Approved
0.622 Remote Similarity NPD3701 Clinical (unspecified phase)
0.622 Remote Similarity NPD6933 Approved
0.6216 Remote Similarity NPD4194 Approved
0.6216 Remote Similarity NPD4193 Approved
0.6216 Remote Similarity NPD368 Approved
0.6216 Remote Similarity NPD4192 Approved
0.6216 Remote Similarity NPD4191 Approved
0.6211 Remote Similarity NPD5696 Approved
0.619 Remote Similarity NPD6929 Approved
0.6186 Remote Similarity NPD5224 Approved
0.6186 Remote Similarity NPD5225 Approved
0.6186 Remote Similarity NPD5226 Approved
0.6186 Remote Similarity NPD4633 Approved
0.6154 Remote Similarity NPD5207 Approved
0.6154 Remote Similarity NPD5692 Phase 3
0.6145 Remote Similarity NPD6932 Approved
0.6129 Remote Similarity NPD7748 Approved
0.6122 Remote Similarity NPD5175 Approved
0.6122 Remote Similarity NPD5174 Approved
0.6122 Remote Similarity NPD4754 Approved
0.6118 Remote Similarity NPD6931 Approved
0.6118 Remote Similarity NPD6930 Phase 2
0.6118 Remote Similarity NPD7332 Phase 2
0.6098 Remote Similarity NPD8264 Approved
0.6098 Remote Similarity NPD6942 Approved
0.6098 Remote Similarity NPD7339 Approved
0.6092 Remote Similarity NPD6110 Phase 1
0.6087 Remote Similarity NPD5694 Approved
0.6087 Remote Similarity NPD6050 Approved
0.6067 Remote Similarity NPD4249 Approved
0.6067 Remote Similarity NPD6098 Approved
0.6064 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6056 Remote Similarity NPD4627 Clinical (unspecified phase)
0.6047 Remote Similarity NPD4139 Approved
0.6047 Remote Similarity NPD4692 Approved
0.6023 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6023 Remote Similarity NPD5766 Clinical (unspecified phase)
0.6022 Remote Similarity NPD5133 Approved
0.6 Remote Similarity NPD6683 Phase 2
0.6 Remote Similarity NPD6675 Approved
0.6 Remote Similarity NPD4250 Approved
0.6 Remote Similarity NPD5739 Approved
0.6 Remote Similarity NPD4768 Approved
0.6 Remote Similarity NPD7128 Approved
0.6 Remote Similarity NPD6402 Approved
0.6 Remote Similarity NPD4767 Approved
0.6 Remote Similarity NPD4251 Approved
0.5978 Remote Similarity NPD46 Approved
0.5978 Remote Similarity NPD6698 Approved
0.5977 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5972 Remote Similarity NPD4219 Approved
0.5957 Remote Similarity NPD6001 Approved
0.5957 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5957 Remote Similarity NPD7900 Approved
0.5955 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5941 Remote Similarity NPD6412 Phase 2
0.5941 Remote Similarity NPD5697 Approved
0.5941 Remote Similarity NPD5701 Approved
0.5938 Remote Similarity NPD7902 Approved
0.593 Remote Similarity NPD7525 Registered
0.5921 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5909 Remote Similarity NPD6695 Phase 3
0.5897 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5882 Remote Similarity NPD6881 Approved
0.5882 Remote Similarity NPD4730 Approved
0.5882 Remote Similarity NPD7320 Approved

Structure

External Identifiers

PubChem CID   46833128
ChEMBL   CHEMBL1098810
ZINC  

Physicochemical Properties

Molecular Weight:  318.22
ALogP:  3.1651
MLogP:  3.33
XLogP:  3.422
# Rotatable Bonds:  7
Polar Surface Area:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  23

Download Data

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Biological Activities  
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