Natural Product: NPC329656

Natural Product ID:  NPC329656
Common Name:   Gibberosene B
IUPAC Name:   [(1S,4E,8Z,10Z,13S,14R)-4,8,14-trimethyl-11-propan-2-yl-15-oxabicyclo[12.1.0]pentadeca-4,8,10-trien-13-yl] acetate
Synonyms:   gibberosene B
Molecular Formula:   C22H34O3
Standard InCHIKey:  DGDSKYGEKMVUCF-AZVOUQKQSA-N
Standard InCHI:  InChI=1S/C22H34O3/c1-15(2)19-12-10-16(3)8-7-9-17(4)11-13-20-22(6,25-20)21(14-19)24-18(5)23/h9-10,12,15,20-21H,7-8,11,13-14H2,1-6H3/b16-10-,17-9+,19-12-/t20-,21-,22+/m0/s1
Canonical SMILES:  CC(=O)O[C@H]1C/C(=C/C=C(/C)CC/C=C(/CC[C@H]2[C@@]1(C)O2)C)/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
NPO25026 Sinularia gibberosa Species Alcyoniidae Eukaryota PMID[18198839]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT83 Cell Line MCF7 Homo sapiens GI = 21.5 % DrugMatrix in vitro pharmacology data
NPT65 Cell Line HepG2 Homo sapiens GI = 24 % DrugMatrix in vitro pharmacology data
NPT81 Cell Line A549 Homo sapiens IC50 > 20 ug/ml 23434131
NPT2 Others Unspecified IC50 > 20 ug/ml 12828479
NPT83 Cell Line MCF7 Homo sapiens IC50 > 20 ug/ml 18359631
NPT65 Cell Line HepG2 Homo sapiens IC50 > 20 ug/ml 20427099

  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 NPC329656 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
0.9143 High Similarity NPC301525
0.8696 High Similarity NPC475310
0.8533 High Similarity NPC474894
0.8514 High Similarity NPC471537
0.8472 Intermediate Similarity NPC93213
0.8158 Intermediate Similarity NPC474739
0.8133 Intermediate Similarity NPC474005
0.8056 Intermediate Similarity NPC477084
0.8028 Intermediate Similarity NPC269841
0.7969 Intermediate Similarity NPC223604
0.7848 Intermediate Similarity NPC475622
0.7848 Intermediate Similarity NPC108045
0.7778 Intermediate Similarity NPC239373
0.7778 Intermediate Similarity NPC329989
0.7746 Intermediate Similarity NPC193029
0.7746 Intermediate Similarity NPC473357
0.7733 Intermediate Similarity NPC475861
0.7647 Intermediate Similarity NPC127824
0.7625 Intermediate Similarity NPC475989
0.76 Intermediate Similarity NPC471525
0.7564 Intermediate Similarity NPC617
0.7561 Intermediate Similarity NPC61527
0.7534 Intermediate Similarity NPC22301
0.7534 Intermediate Similarity NPC101622
0.7532 Intermediate Similarity NPC84360
0.7532 Intermediate Similarity NPC40049
0.7532 Intermediate Similarity NPC186109
0.75 Intermediate Similarity NPC472266
0.75 Intermediate Similarity NPC113639
0.7468 Intermediate Similarity NPC233332
0.7467 Intermediate Similarity NPC476709
0.7432 Intermediate Similarity NPC37929
0.7432 Intermediate Similarity NPC64234
0.7432 Intermediate Similarity NPC473361
0.7432 Intermediate Similarity NPC4299
0.7432 Intermediate Similarity NPC329904
0.7429 Intermediate Similarity NPC217940
0.7407 Intermediate Similarity NPC231601
0.7397 Intermediate Similarity NPC276290
0.7375 Intermediate Similarity NPC207188
0.7375 Intermediate Similarity NPC475481
0.7375 Intermediate Similarity NPC79277
0.7375 Intermediate Similarity NPC141810
0.7368 Intermediate Similarity NPC474551
0.7342 Intermediate Similarity NPC325869
0.7324 Intermediate Similarity NPC287744
0.7324 Intermediate Similarity NPC140233
0.7317 Intermediate Similarity NPC78673
0.7317 Intermediate Similarity NPC160517
0.7317 Intermediate Similarity NPC186155
0.7297 Intermediate Similarity NPC232812
0.725 Intermediate Similarity NPC469920
0.725 Intermediate Similarity NPC103634
0.7237 Intermediate Similarity NPC474543
0.7237 Intermediate Similarity NPC472018
0.7237 Intermediate Similarity NPC238425
0.7215 Intermediate Similarity NPC3852
0.7215 Intermediate Similarity NPC474341
0.7209 Intermediate Similarity NPC475748
0.7209 Intermediate Similarity NPC51653
0.72 Intermediate Similarity NPC469660
0.72 Intermediate Similarity NPC129630
0.7195 Intermediate Similarity NPC49208
0.7195 Intermediate Similarity NPC170377
0.7195 Intermediate Similarity NPC475842
0.7188 Intermediate Similarity NPC289388
0.7188 Intermediate Similarity NPC142103
0.7179 Intermediate Similarity NPC271070
0.7179 Intermediate Similarity NPC239127
0.7176 Intermediate Similarity NPC233997
0.7162 Intermediate Similarity NPC305698
0.7162 Intermediate Similarity NPC273508
0.7162 Intermediate Similarity NPC209327
0.7143 Intermediate Similarity NPC214315
0.7143 Intermediate Similarity NPC204048
0.7143 Intermediate Similarity NPC471480
0.7143 Intermediate Similarity NPC104644
0.7143 Intermediate Similarity NPC330016
0.7143 Intermediate Similarity NPC160540
0.7125 Intermediate Similarity NPC471740
0.7125 Intermediate Similarity NPC271632
0.7108 Intermediate Similarity NPC72464
0.7105 Intermediate Similarity NPC472254
0.7101 Intermediate Similarity NPC240206
0.7093 Intermediate Similarity NPC151770
0.7089 Intermediate Similarity NPC476703
0.7089 Intermediate Similarity NPC476325
0.7089 Intermediate Similarity NPC476439
0.7089 Intermediate Similarity NPC476264
0.7089 Intermediate Similarity NPC283619
0.7083 Intermediate Similarity NPC469723
0.7077 Intermediate Similarity NPC244452
0.7073 Intermediate Similarity NPC475936
0.7067 Intermediate Similarity NPC477449
0.7067 Intermediate Similarity NPC74722
0.7067 Intermediate Similarity NPC477448
0.7067 Intermediate Similarity NPC304690
0.7059 Intermediate Similarity NPC471739
0.7059 Intermediate Similarity NPC96663
0.7059 Intermediate Similarity NPC141699
0.7059 Intermediate Similarity NPC231889
0.7059 Intermediate Similarity NPC474765
0.7051 Intermediate Similarity NPC255060
0.7051 Intermediate Similarity NPC324762
0.7042 Intermediate Similarity NPC328776
0.7042 Intermediate Similarity NPC320305
0.7027 Intermediate Similarity NPC259299
0.7024 Intermediate Similarity NPC319795
0.7024 Intermediate Similarity NPC50362
0.7024 Intermediate Similarity NPC197903
0.7024 Intermediate Similarity NPC99395
0.7024 Intermediate Similarity NPC38468
0.7013 Intermediate Similarity NPC92909
0.7013 Intermediate Similarity NPC107783
0.7013 Intermediate Similarity NPC470237
0.7013 Intermediate Similarity NPC477085
0.7013 Intermediate Similarity NPC167145
0.7011 Intermediate Similarity NPC3952
0.7 Intermediate Similarity NPC83838
0.7 Intermediate Similarity NPC477089
0.7 Intermediate Similarity NPC11796
0.7 Intermediate Similarity NPC218817
0.7 Intermediate Similarity NPC143810
0.7 Intermediate Similarity NPC57664
0.6988 Remote Similarity NPC23748
0.6988 Remote Similarity NPC272814
0.6988 Remote Similarity NPC53867
0.6977 Remote Similarity NPC201046
0.6977 Remote Similarity NPC309656
0.6974 Remote Similarity NPC472955
0.6974 Remote Similarity NPC69462
0.697 Remote Similarity NPC170167
0.6962 Remote Similarity NPC474527
0.6962 Remote Similarity NPC170148
0.6962 Remote Similarity NPC471726
0.6962 Remote Similarity NPC469880
0.6962 Remote Similarity NPC474447
0.6957 Remote Similarity NPC165808
0.6951 Remote Similarity NPC184208
0.6951 Remote Similarity NPC286229
0.6951 Remote Similarity NPC315731
0.6951 Remote Similarity NPC112868
0.6951 Remote Similarity NPC8538
0.6951 Remote Similarity NPC25554
0.6944 Remote Similarity NPC54925
0.6941 Remote Similarity NPC137253
0.6941 Remote Similarity NPC311163
0.6941 Remote Similarity NPC50637
0.6923 Remote Similarity NPC190859
0.6923 Remote Similarity NPC167049
0.6923 Remote Similarity NPC469691
0.6923 Remote Similarity NPC107654
0.6923 Remote Similarity NPC474758
0.6914 Remote Similarity NPC622
0.6914 Remote Similarity NPC100906
0.6914 Remote Similarity NPC44083
0.6914 Remote Similarity NPC276647
0.6914 Remote Similarity NPC153987
0.6914 Remote Similarity NPC158565
0.6905 Remote Similarity NPC9868
0.6905 Remote Similarity NPC306951
0.6897 Remote Similarity NPC115179
0.6897 Remote Similarity NPC83423
0.6897 Remote Similarity NPC106040
0.6892 Remote Similarity NPC477982
0.6889 Remote Similarity NPC107476
0.6883 Remote Similarity NPC477087
0.6883 Remote Similarity NPC477086
0.6875 Remote Similarity NPC470240
0.6875 Remote Similarity NPC476794
0.6867 Remote Similarity NPC35556
0.6867 Remote Similarity NPC474291
0.6866 Remote Similarity NPC165755
0.686 Remote Similarity NPC476600
0.6854 Remote Similarity NPC212486
0.6849 Remote Similarity NPC328089
0.6849 Remote Similarity NPC68343
0.6849 Remote Similarity NPC34883
0.6848 Remote Similarity NPC471582
0.6842 Remote Similarity NPC296522
0.6842 Remote Similarity NPC144511
0.6842 Remote Similarity NPC265574
0.6842 Remote Similarity NPC473772
0.6842 Remote Similarity NPC261398
0.6842 Remote Similarity NPC16964
0.6842 Remote Similarity NPC107130
0.6842 Remote Similarity NPC199557
0.6835 Remote Similarity NPC475771
0.6835 Remote Similarity NPC469678
0.6835 Remote Similarity NPC199445
0.6835 Remote Similarity NPC469669
0.6835 Remote Similarity NPC12696
0.6835 Remote Similarity NPC474419
0.6829 Remote Similarity NPC233377
0.6829 Remote Similarity NPC474510
0.6829 Remote Similarity NPC269791
0.6829 Remote Similarity NPC472470
0.6829 Remote Similarity NPC473685
0.6824 Remote Similarity NPC474369
0.6824 Remote Similarity NPC471494

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC329656 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
0.7714 Intermediate Similarity NPD2685 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD7838 Discovery
0.7024 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.6957 Remote Similarity NPD6648 Approved
0.6818 Remote Similarity NPD46 Approved
0.6818 Remote Similarity NPD6698 Approved
0.6742 Remote Similarity NPD7983 Approved
0.6705 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6705 Remote Similarity NPD6101 Approved
0.6625 Remote Similarity NPD8039 Approved
0.6622 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6588 Remote Similarity NPD7154 Phase 3
0.6556 Remote Similarity NPD6411 Approved
0.6543 Remote Similarity NPD6933 Approved
0.6526 Remote Similarity NPD5344 Discontinued
0.6517 Remote Similarity NPD1695 Approved
0.65 Remote Similarity NPD6926 Approved
0.65 Remote Similarity NPD6924 Approved
0.6484 Remote Similarity NPD5778 Approved
0.6484 Remote Similarity NPD5779 Approved
0.6477 Remote Similarity NPD7524 Approved
0.6438 Remote Similarity NPD1145 Discontinued
0.6429 Remote Similarity NPD4822 Approved
0.6429 Remote Similarity NPD4820 Approved
0.6429 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6429 Remote Similarity NPD4821 Approved
0.6429 Remote Similarity NPD4819 Approved
0.6395 Remote Similarity NPD6695 Phase 3
0.6353 Remote Similarity NPD5369 Approved
0.6322 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6316 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6279 Remote Similarity NPD5209 Approved
0.6279 Remote Similarity NPD6435 Approved
0.6264 Remote Similarity NPD3168 Discontinued
0.6235 Remote Similarity NPD6931 Approved
0.6235 Remote Similarity NPD6930 Phase 2
0.6207 Remote Similarity NPD5362 Discontinued
0.6196 Remote Similarity NPD7637 Suspended
0.619 Remote Similarity NPD4271 Approved
0.619 Remote Similarity NPD4268 Approved
0.618 Remote Similarity NPD5330 Approved
0.618 Remote Similarity NPD7334 Approved
0.618 Remote Similarity NPD7146 Approved
0.618 Remote Similarity NPD6409 Approved
0.618 Remote Similarity NPD6684 Approved
0.618 Remote Similarity NPD7521 Approved
0.6154 Remote Similarity NPD6051 Approved
0.6118 Remote Similarity NPD6929 Approved
0.6111 Remote Similarity NPD7750 Discontinued
0.6105 Remote Similarity NPD7839 Suspended
0.6071 Remote Similarity NPD6932 Approved
0.6067 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6047 Remote Similarity NPD7509 Discontinued
0.6047 Remote Similarity NPD5368 Approved
0.6044 Remote Similarity NPD6903 Approved
0.6044 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6023 Remote Similarity NPD5331 Approved
0.6023 Remote Similarity NPD5332 Approved
0.6 Remote Similarity NPD6922 Approved
0.6 Remote Similarity NPD6923 Approved
0.6 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6 Remote Similarity NPD6422 Discontinued
0.5979 Remote Similarity NPD4225 Approved
0.5977 Remote Similarity NPD4790 Discontinued
0.5974 Remote Similarity NPD3197 Phase 1
0.596 Remote Similarity NPD3653 Clinical (unspecified phase)
0.5957 Remote Similarity NPD6399 Phase 3
0.5955 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5946 Remote Similarity NPD6109 Phase 1
0.5934 Remote Similarity NPD4250 Approved
0.5934 Remote Similarity NPD4251 Approved
0.593 Remote Similarity NPD6683 Phase 2
0.5926 Remote Similarity NPD7144 Approved
0.5926 Remote Similarity NPD7143 Approved
0.5909 Remote Similarity NPD4270 Approved
0.5909 Remote Similarity NPD4269 Approved
0.5909 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5889 Remote Similarity NPD6893 Approved
0.5882 Remote Similarity NPD5343 Approved
0.5882 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5882 Remote Similarity NPD5776 Phase 2
0.5882 Remote Similarity NPD6925 Approved
0.587 Remote Similarity NPD5737 Approved
0.587 Remote Similarity NPD6672 Approved
0.5865 Remote Similarity NPD6371 Approved
0.5862 Remote Similarity NPD7514 Phase 3
0.5862 Remote Similarity NPD7332 Phase 2
0.5857 Remote Similarity NPD6927 Phase 3
0.5857 Remote Similarity NPD29 Approved
0.5857 Remote Similarity NPD28 Approved
0.5854 Remote Similarity NPD7150 Approved
0.5854 Remote Similarity NPD7151 Approved
0.5854 Remote Similarity NPD7152 Approved
0.5851 Remote Similarity NPD7087 Discontinued
0.5851 Remote Similarity NPD6050 Approved
0.5833 Remote Similarity NPD8264 Approved
0.5824 Remote Similarity NPD4249 Approved
0.5824 Remote Similarity NPD5786 Approved
0.5824 Remote Similarity NPD6098 Approved
0.5823 Remote Similarity NPD7331 Phase 2
0.5814 Remote Similarity NPD7322 Clinical (unspecified phase)
0.5814 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5814 Remote Similarity NPD7145 Approved
0.5797 Remote Similarity NPD9410 Clinical (unspecified phase)
0.5795 Remote Similarity NPD6898 Phase 1
0.5795 Remote Similarity NPD6902 Approved
0.5758 Remote Similarity NPD7798 Approved
0.5747 Remote Similarity NPD7645 Phase 2
0.5745 Remote Similarity NPD5207 Approved
0.5745 Remote Similarity NPD5692 Phase 3
0.5729 Remote Similarity NPD7900 Approved
0.5729 Remote Similarity NPD7748 Approved
0.5729 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5714 Remote Similarity NPD6083 Phase 2
0.5714 Remote Similarity NPD4191 Approved
0.5714 Remote Similarity NPD4193 Approved
0.5714 Remote Similarity NPD1694 Approved
0.5714 Remote Similarity NPD368 Approved
0.5714 Remote Similarity NPD4194 Approved
0.5714 Remote Similarity NPD5363 Approved
0.5714 Remote Similarity NPD4192 Approved
0.5714 Remote Similarity NPD6084 Phase 2
0.5696 Remote Similarity NPD7341 Phase 2
0.5688 Remote Similarity NPD7115 Discovery
0.5684 Remote Similarity NPD5694 Approved
0.5682 Remote Similarity NPD4252 Approved
0.5672 Remote Similarity NPD6097 Approved
0.5672 Remote Similarity NPD6096 Approved
0.567 Remote Similarity NPD5695 Phase 3
0.567 Remote Similarity NPD6356 Clinical (unspecified phase)
0.567 Remote Similarity NPD1698 Clinical (unspecified phase)
0.566 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5647 Remote Similarity NPD6942 Approved
0.5647 Remote Similarity NPD7339 Approved
0.5638 Remote Similarity NPD6904 Approved
0.5638 Remote Similarity NPD6673 Approved
0.5638 Remote Similarity NPD6080 Approved
0.5631 Remote Similarity NPD5357 Phase 1
0.5631 Remote Similarity NPD6008 Approved
0.5616 Remote Similarity NPD4266 Approved
0.5616 Remote Similarity NPD3196 Approved
0.5616 Remote Similarity NPD3194 Approved
0.5616 Remote Similarity NPD3195 Phase 2
0.5612 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5604 Remote Similarity NPD4786 Approved

Structure

External Identifiers

PubChem CID   44448197
ChEMBL   CHEMBL404665
ZINC  

Physicochemical Properties

Molecular Weight:  346.25
ALogP:  2.6468
MLogP:  3.55
XLogP:  5.252
# Rotatable Bonds:  9
Polar Surface Area:  38.83
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  25

Download Data

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