Natural Product: NPC471537

Natural Product ID:  NPC471537
Common Name:   Gibberosene D
IUPAC Name:   [(1S,4E,8S,9E,11Z,13S,14R)-8-hydroxy-4,8,14-trimethyl-11-propan-2-yl-15-oxabicyclo[12.1.0]pentadeca-4,9,11-trien-13-yl] acetate
Synonyms:   gibberosene D
Molecular Formula:   C22H34O4
Standard InCHIKey:  HVKLCFQGBOCFBB-NMBOOFCZSA-N
Standard InCHI:  InChI=1S/C22H34O4/c1-15(2)18-11-13-21(5,24)12-7-8-16(3)9-10-19-22(6,26-19)20(14-18)25-17(4)23/h8,11,13-15,19-20,24H,7,9-10,12H2,1-6H3/b13-11+,16-8+,18-14+/t19-,20-,21-,22+/m0/s1
Canonical SMILES:  CC(=O)O[C@H]1/C=C(C=C[C@@](C)(O)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 IC50 > 20 ug/ml 22989532
NPT65 Cell Line HepG2 Homo sapiens IC50 > 20 ug/ml 18468908
NPT2 Others Unspecified IC50 > 20 ug/ml 25637363
NPT81 Cell Line A549 Homo sapiens IC50 > 20 ug/ml 11421746

  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 NPC471537 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
0.9221 High Similarity NPC474894
0.9067 High Similarity NPC301525
0.8889 High Similarity NPC61527
0.8701 High Similarity NPC84360
0.8649 High Similarity NPC4299
0.8649 High Similarity NPC473361
0.8649 High Similarity NPC329904
0.8642 High Similarity NPC78673
0.8642 High Similarity NPC186155
0.8642 High Similarity NPC160517
0.8514 High Similarity NPC329656
0.8514 High Similarity NPC101622
0.8354 Intermediate Similarity NPC474005
0.8289 Intermediate Similarity NPC477084
0.8272 Intermediate Similarity NPC315731
0.8182 Intermediate Similarity NPC477085
0.8158 Intermediate Similarity NPC129630
0.8148 Intermediate Similarity NPC474739
0.8095 Intermediate Similarity NPC471494
0.8077 Intermediate Similarity NPC315843
0.8077 Intermediate Similarity NPC107654
0.8077 Intermediate Similarity NPC471525
0.8072 Intermediate Similarity NPC49208
0.8072 Intermediate Similarity NPC231601
0.8052 Intermediate Similarity NPC477086
0.8052 Intermediate Similarity NPC316185
0.8052 Intermediate Similarity NPC472254
0.8052 Intermediate Similarity NPC477087
0.8049 Intermediate Similarity NPC112868
0.8049 Intermediate Similarity NPC8538
0.8049 Intermediate Similarity NPC184208
0.8046 Intermediate Similarity NPC3952
0.8026 Intermediate Similarity NPC239373
0.8026 Intermediate Similarity NPC329989
0.8026 Intermediate Similarity NPC269841
0.8025 Intermediate Similarity NPC325869
0.8 Intermediate Similarity NPC57664
0.8 Intermediate Similarity NPC311163
0.8 Intermediate Similarity NPC476439
0.8 Intermediate Similarity NPC40049
0.7931 Intermediate Similarity NPC83423
0.7882 Intermediate Similarity NPC11804
0.7875 Intermediate Similarity NPC469880
0.7875 Intermediate Similarity NPC271070
0.7875 Intermediate Similarity NPC188860
0.7857 Intermediate Similarity NPC44261
0.7857 Intermediate Similarity NPC161045
0.7857 Intermediate Similarity NPC474809
0.7857 Intermediate Similarity NPC23748
0.7848 Intermediate Similarity NPC474280
0.7805 Intermediate Similarity NPC139712
0.7805 Intermediate Similarity NPC86971
0.7791 Intermediate Similarity NPC122502
0.7791 Intermediate Similarity NPC116575
0.7778 Intermediate Similarity NPC315394
0.7778 Intermediate Similarity NPC474278
0.7778 Intermediate Similarity NPC233071
0.7763 Intermediate Similarity NPC193029
0.7763 Intermediate Similarity NPC473357
0.7742 Intermediate Similarity NPC475053
0.7738 Intermediate Similarity NPC474252
0.7727 Intermediate Similarity NPC115179
0.7727 Intermediate Similarity NPC106040
0.7722 Intermediate Similarity NPC329890
0.7701 Intermediate Similarity NPC313658
0.7701 Intermediate Similarity NPC474765
0.7701 Intermediate Similarity NPC199382
0.7701 Intermediate Similarity NPC316138
0.7701 Intermediate Similarity NPC131329
0.7692 Intermediate Similarity NPC475310
0.7692 Intermediate Similarity NPC107476
0.7674 Intermediate Similarity NPC474369
0.7671 Intermediate Similarity NPC127824
0.7662 Intermediate Similarity NPC305698
0.7647 Intermediate Similarity NPC475989
0.764 Intermediate Similarity NPC313670
0.7625 Intermediate Similarity NPC470686
0.7619 Intermediate Similarity NPC79277
0.7619 Intermediate Similarity NPC475481
0.7619 Intermediate Similarity NPC475944
0.7614 Intermediate Similarity NPC260343
0.7609 Intermediate Similarity NPC476315
0.759 Intermediate Similarity NPC1180
0.759 Intermediate Similarity NPC477088
0.759 Intermediate Similarity NPC475210
0.7568 Intermediate Similarity NPC55376
0.7564 Intermediate Similarity NPC151481
0.7564 Intermediate Similarity NPC304690
0.7564 Intermediate Similarity NPC74722
0.7561 Intermediate Similarity NPC476703
0.7558 Intermediate Similarity NPC72464
0.7558 Intermediate Similarity NPC243618
0.7558 Intermediate Similarity NPC474776
0.7558 Intermediate Similarity NPC70424
0.7556 Intermediate Similarity NPC158061
0.7532 Intermediate Similarity NPC472266
0.7532 Intermediate Similarity NPC259299
0.7531 Intermediate Similarity NPC93213
0.7528 Intermediate Similarity NPC20946
0.7528 Intermediate Similarity NPC212598
0.7528 Intermediate Similarity NPC133450
0.75 Intermediate Similarity NPC233332
0.75 Intermediate Similarity NPC270013
0.75 Intermediate Similarity NPC329914
0.75 Intermediate Similarity NPC14961
0.75 Intermediate Similarity NPC477959
0.75 Intermediate Similarity NPC45409
0.75 Intermediate Similarity NPC86005
0.75 Intermediate Similarity NPC308844
0.7473 Intermediate Similarity NPC109406
0.7471 Intermediate Similarity NPC35933
0.747 Intermediate Similarity NPC474816
0.747 Intermediate Similarity NPC267231
0.747 Intermediate Similarity NPC477089
0.747 Intermediate Similarity NPC209135
0.7468 Intermediate Similarity NPC64234
0.7468 Intermediate Similarity NPC37929
0.7468 Intermediate Similarity NPC469660
0.7468 Intermediate Similarity NPC476037
0.7467 Intermediate Similarity NPC217940
0.7447 Intermediate Similarity NPC203627
0.7447 Intermediate Similarity NPC475653
0.7447 Intermediate Similarity NPC161855
0.7444 Intermediate Similarity NPC474761
0.7444 Intermediate Similarity NPC473448
0.7444 Intermediate Similarity NPC51653
0.7444 Intermediate Similarity NPC476004
0.7444 Intermediate Similarity NPC177668
0.7442 Intermediate Similarity NPC16488
0.7442 Intermediate Similarity NPC170377
0.7439 Intermediate Similarity NPC256720
0.7439 Intermediate Similarity NPC477202
0.7439 Intermediate Similarity NPC170148
0.7439 Intermediate Similarity NPC236228
0.7436 Intermediate Similarity NPC272961
0.7436 Intermediate Similarity NPC276290
0.7436 Intermediate Similarity NPC209327
0.7436 Intermediate Similarity NPC310210
0.7436 Intermediate Similarity NPC273508
0.7419 Intermediate Similarity NPC173329
0.7419 Intermediate Similarity NPC473291
0.7419 Intermediate Similarity NPC255410
0.7419 Intermediate Similarity NPC279621
0.7419 Intermediate Similarity NPC288350
0.7416 Intermediate Similarity NPC227379
0.7416 Intermediate Similarity NPC474471
0.7412 Intermediate Similarity NPC325031
0.7412 Intermediate Similarity NPC141810
0.7412 Intermediate Similarity NPC246621
0.7403 Intermediate Similarity NPC146811
0.7391 Intermediate Similarity NPC474035
0.7391 Intermediate Similarity NPC469491
0.7391 Intermediate Similarity NPC57405
0.7391 Intermediate Similarity NPC472467
0.7391 Intermediate Similarity NPC303942
0.7391 Intermediate Similarity NPC81386
0.7386 Intermediate Similarity NPC469483
0.7386 Intermediate Similarity NPC281316
0.7386 Intermediate Similarity NPC198314
0.7386 Intermediate Similarity NPC315395
0.7386 Intermediate Similarity NPC164393
0.7386 Intermediate Similarity NPC234038
0.7386 Intermediate Similarity NPC316426
0.7381 Intermediate Similarity NPC271632
0.7381 Intermediate Similarity NPC476701
0.7363 Intermediate Similarity NPC471324
0.7363 Intermediate Similarity NPC476075
0.7363 Intermediate Similarity NPC476084
0.7363 Intermediate Similarity NPC114172
0.7363 Intermediate Similarity NPC206679
0.7356 Intermediate Similarity NPC196487
0.7356 Intermediate Similarity NPC9868
0.7356 Intermediate Similarity NPC14575
0.7349 Intermediate Similarity NPC477203
0.7349 Intermediate Similarity NPC262747
0.7342 Intermediate Similarity NPC232812
0.7342 Intermediate Similarity NPC475004
0.734 Intermediate Similarity NPC475332
0.734 Intermediate Similarity NPC120299
0.734 Intermediate Similarity NPC205143
0.7333 Intermediate Similarity NPC49783
0.7326 Intermediate Similarity NPC474291
0.7326 Intermediate Similarity NPC477390
0.7326 Intermediate Similarity NPC85772
0.7326 Intermediate Similarity NPC477385
0.7317 Intermediate Similarity NPC113639
0.7317 Intermediate Similarity NPC329852
0.7317 Intermediate Similarity NPC199445
0.7312 Intermediate Similarity NPC272050
0.7312 Intermediate Similarity NPC300710
0.7312 Intermediate Similarity NPC36954
0.7312 Intermediate Similarity NPC220221
0.7312 Intermediate Similarity NPC475659
0.7303 Intermediate Similarity NPC72513
0.7303 Intermediate Similarity NPC245004
0.7297 Intermediate Similarity NPC122239
0.7294 Intermediate Similarity NPC190008
0.7294 Intermediate Similarity NPC233377
0.7283 Intermediate Similarity NPC159092
0.7283 Intermediate Similarity NPC472195

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC471537 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
0.8256 Intermediate Similarity NPD7838 Discovery
0.7742 Intermediate Similarity NPD6648 Approved
0.7733 Intermediate Similarity NPD2685 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD46 Approved
0.764 Intermediate Similarity NPD6698 Approved
0.7556 Intermediate Similarity NPD7983 Approved
0.7474 Intermediate Similarity NPD5344 Discontinued
0.7447 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD7154 Phase 3
0.7294 Intermediate Similarity NPD4822 Approved
0.7294 Intermediate Similarity NPD4819 Approved
0.7294 Intermediate Similarity NPD5790 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD4821 Approved
0.7294 Intermediate Similarity NPD4820 Approved
0.7097 Intermediate Similarity NPD5779 Approved
0.7097 Intermediate Similarity NPD5778 Approved
0.7059 Intermediate Similarity NPD4268 Approved
0.7059 Intermediate Similarity NPD4271 Approved
0.7045 Intermediate Similarity NPD5362 Discontinued
0.6989 Remote Similarity NPD7637 Suspended
0.6966 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6905 Remote Similarity NPD8039 Approved
0.6889 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6889 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6875 Remote Similarity NPD7839 Suspended
0.6854 Remote Similarity NPD5332 Approved
0.6854 Remote Similarity NPD5331 Approved
0.6818 Remote Similarity NPD4790 Discontinued
0.6774 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6774 Remote Similarity NPD6101 Approved
0.6753 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6742 Remote Similarity NPD4270 Approved
0.6742 Remote Similarity NPD4269 Approved
0.6742 Remote Similarity NPD5209 Approved
0.6739 Remote Similarity NPD7524 Approved
0.6739 Remote Similarity NPD4250 Approved
0.6739 Remote Similarity NPD4251 Approved
0.6735 Remote Similarity NPD4225 Approved
0.6702 Remote Similarity NPD5785 Approved
0.6701 Remote Similarity NPD4792 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6695 Phase 3
0.6632 Remote Similarity NPD6411 Approved
0.663 Remote Similarity NPD5786 Approved
0.663 Remote Similarity NPD4249 Approved
0.6629 Remote Similarity NPD5369 Approved
0.6593 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6571 Remote Similarity NPD6371 Approved
0.6556 Remote Similarity NPD6435 Approved
0.6522 Remote Similarity NPD5363 Approved
0.6517 Remote Similarity NPD7514 Phase 3
0.6517 Remote Similarity NPD4252 Approved
0.6517 Remote Similarity NPD7332 Phase 2
0.6514 Remote Similarity NPD7115 Discovery
0.6512 Remote Similarity NPD8264 Approved
0.6509 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6494 Remote Similarity NPD585 Clinical (unspecified phase)
0.6477 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6463 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6444 Remote Similarity NPD6902 Approved
0.6442 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6383 Remote Similarity NPD7750 Discontinued
0.6364 Remote Similarity NPD7505 Discontinued
0.6348 Remote Similarity NPD8273 Phase 1
0.6333 Remote Similarity NPD6931 Approved
0.6333 Remote Similarity NPD6930 Phase 2
0.6333 Remote Similarity NPD5368 Approved
0.6292 Remote Similarity NPD7145 Approved
0.6283 Remote Similarity NPD8516 Approved
0.6283 Remote Similarity NPD8517 Approved
0.6283 Remote Similarity NPD8515 Approved
0.6283 Remote Similarity NPD8513 Phase 3
0.6279 Remote Similarity NPD4732 Discontinued
0.6263 Remote Similarity NPD1698 Clinical (unspecified phase)
0.625 Remote Similarity NPD5370 Suspended
0.625 Remote Similarity NPD4194 Approved
0.625 Remote Similarity NPD1695 Approved
0.625 Remote Similarity NPD4193 Approved
0.625 Remote Similarity NPD4191 Approved
0.625 Remote Similarity NPD368 Approved
0.625 Remote Similarity NPD4192 Approved
0.625 Remote Similarity NPD6051 Approved
0.625 Remote Similarity NPD6933 Approved
0.6222 Remote Similarity NPD6929 Approved
0.6207 Remote Similarity NPD6926 Approved
0.6207 Remote Similarity NPD6924 Approved
0.618 Remote Similarity NPD4756 Discovery
0.618 Remote Similarity NPD6925 Approved
0.618 Remote Similarity NPD6932 Approved
0.618 Remote Similarity NPD5776 Phase 2
0.6176 Remote Similarity NPD7640 Approved
0.6176 Remote Similarity NPD7639 Approved
0.6122 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6122 Remote Similarity NPD7087 Discontinued
0.6098 Remote Similarity NPD3197 Phase 1
0.6087 Remote Similarity NPD6898 Phase 1
0.6078 Remote Similarity NPD7638 Approved
0.6076 Remote Similarity NPD6109 Phase 1
0.6075 Remote Similarity NPD6686 Approved
0.6055 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6047 Remote Similarity NPD7143 Approved
0.6047 Remote Similarity NPD7144 Approved
0.6038 Remote Similarity NPD6640 Phase 3
0.6034 Remote Similarity NPD7829 Approved
0.6034 Remote Similarity NPD7830 Approved
0.6022 Remote Similarity NPD4752 Clinical (unspecified phase)
0.602 Remote Similarity NPD3168 Discontinued
0.6017 Remote Similarity NPD8074 Phase 3
0.6 Remote Similarity NPD7503 Approved
0.6 Remote Similarity NPD6927 Phase 3
0.6 Remote Similarity NPD6647 Phase 2
0.6 Remote Similarity NPD6893 Approved
0.5977 Remote Similarity NPD7150 Approved
0.5977 Remote Similarity NPD7151 Approved
0.5977 Remote Similarity NPD7152 Approved
0.5938 Remote Similarity NPD6422 Discontinued
0.593 Remote Similarity NPD6922 Approved
0.593 Remote Similarity NPD6923 Approved
0.59 Remote Similarity NPD6399 Phase 3
0.5897 Remote Similarity NPD342 Phase 1
0.5872 Remote Similarity NPD4061 Clinical (unspecified phase)
0.587 Remote Similarity NPD6683 Phase 2
0.5862 Remote Similarity NPD8444 Approved
0.5856 Remote Similarity NPD6053 Discontinued
0.5849 Remote Similarity NPD5738 Clinical (unspecified phase)
0.5833 Remote Similarity NPD1694 Approved
0.5823 Remote Similarity NPD4219 Approved
0.5818 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5806 Remote Similarity NPD7509 Discontinued
0.5806 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5798 Remote Similarity NPD8451 Approved
0.5789 Remote Similarity NPD6110 Phase 1
0.5789 Remote Similarity NPD4198 Discontinued
0.5789 Remote Similarity NPD7500 Approved
0.5769 Remote Similarity NPD3194 Approved
0.5769 Remote Similarity NPD3196 Approved
0.5769 Remote Similarity NPD3195 Phase 2
0.5769 Remote Similarity NPD4266 Approved
0.5765 Remote Similarity NPD7331 Phase 2
0.5763 Remote Similarity NPD7642 Approved
0.5755 Remote Similarity NPD3653 Clinical (unspecified phase)
0.575 Remote Similarity NPD8448 Approved
0.5741 Remote Similarity NPD4211 Phase 1
0.5739 Remote Similarity NPD7327 Approved
0.5739 Remote Similarity NPD7328 Approved
0.5733 Remote Similarity NPD4220 Pre-registration
0.5727 Remote Similarity NPD6413 Approved
0.5726 Remote Similarity NPD8033 Approved
0.5714 Remote Similarity NPD8341 Approved
0.5714 Remote Similarity NPD8340 Approved
0.5714 Remote Similarity NPD8299 Approved
0.5714 Remote Similarity NPD8342 Approved
0.5702 Remote Similarity NPD2629 Approved
0.57 Remote Similarity NPD7136 Phase 2
0.569 Remote Similarity NPD7516 Approved
0.5688 Remote Similarity NPD6685 Approved
0.5686 Remote Similarity NPD5282 Discontinued
0.5686 Remote Similarity NPD7748 Approved
0.5676 Remote Similarity NPD6421 Discontinued
0.5676 Remote Similarity NPD2067 Discontinued
0.5673 Remote Similarity NPD6084 Phase 2
0.5673 Remote Similarity NPD6083 Phase 2
0.567 Remote Similarity NPD1696 Phase 3
0.5641 Remote Similarity NPD8377 Approved
0.5641 Remote Similarity NPD8294 Approved
0.5641 Remote Similarity NPD3172 Approved
0.5631 Remote Similarity NPD5695 Phase 3
0.561 Remote Similarity NPD8392 Approved
0.561 Remote Similarity NPD8390 Approved
0.561 Remote Similarity NPD8391 Approved
0.5607 Remote Similarity NPD7632 Discontinued
0.5603 Remote Similarity NPD694 Clinical (unspecified phase)
0.5603 Remote Similarity NPD7641 Discontinued

Structure

External Identifiers

PubChem CID   24801756
ChEMBL   CHEMBL255514
ZINC  

Physicochemical Properties

Molecular Weight:  362.25
ALogP:  2.0255
MLogP:  3.44
XLogP:  4.077
# Rotatable Bonds:  10
Polar Surface Area:  59.06
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  26

Download Data

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Similar NPs/Drugs