Natural Product: NPC9868

Natural Product ID:  NPC9868
Common Name:   Sinuflexolide
IUPAC Name:   (1S,4S,5R,8E,12R,13R)-4,5,12-trihydroxy-4,8,12-trimethyl-16-methylidene-14-oxabicyclo[11.3.1]heptadec-8-en-15-one
Synonyms:   Sinuflexolide
Molecular Formula:   C20H32O5
Standard InCHIKey:  DAMCLDLKMZAXNC-JZVIKIFUSA-N
Standard InCHI:  InChI=1S/C20H32O5/c1-13-6-5-10-20(4,24)17-12-15(14(2)18(22)25-17)9-11-19(3,23)16(21)8-7-13/h6,15-17,21,23-24H,2,5,7-12H2,1,3-4H3/b13-6+/t15-,16+,17+,19-,20+/m0/s1
Canonical SMILES:  C/C/1=CCC[C@@](C)(O)[C@H]2C[C@H](CC[C@]([C@@H](CC1)O)(C)O)C(=C)C(=O)O2
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
NPO3821 Sinularia flexibilis Species Alcyoniidae Eukaryota PMID[9644083]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT168 Cell Line P388 Mus musculus ED50 = 0.16 ug/ml 26351040
NPT81 Cell Line A549 Homo sapiens ED50 = 0.68 ug/ml 4020828
NPT91 Cell Line KB Homo sapiens ED50 = 0.46 ug/ml 11858989
NPT139 Cell Line HT-29 Homo sapiens ED50 = 0.39 ug/ml 11858989

  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 NPC9868 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
0.95 High Similarity NPC70424
0.95 High Similarity NPC72464
0.95 High Similarity NPC243618
0.9487 High Similarity NPC233377
0.9241 High Similarity NPC103634
0.9157 High Similarity NPC248602
0.9136 High Similarity NPC11620
0.8916 High Similarity NPC137033
0.8837 High Similarity NPC476004
0.8837 High Similarity NPC474761
0.8824 High Similarity NPC474471
0.8824 High Similarity NPC153805
0.8824 High Similarity NPC227379
0.8824 High Similarity NPC281516
0.878 High Similarity NPC474291
0.875 High Similarity NPC71589
0.8736 High Similarity NPC30515
0.8736 High Similarity NPC184463
0.8721 High Similarity NPC307411
0.8621 High Similarity NPC51004
0.8605 High Similarity NPC202672
0.8588 High Similarity NPC164393
0.8571 High Similarity NPC474780
0.8523 High Similarity NPC208886
0.8523 High Similarity NPC470379
0.8523 High Similarity NPC12172
0.8523 High Similarity NPC470373
0.8471 Intermediate Similarity NPC329749
0.8462 Intermediate Similarity NPC40812
0.8444 Intermediate Similarity NPC36954
0.8427 Intermediate Similarity NPC179746
0.8427 Intermediate Similarity NPC81419
0.8427 Intermediate Similarity NPC476300
0.8427 Intermediate Similarity NPC212486
0.8427 Intermediate Similarity NPC475912
0.8372 Intermediate Similarity NPC475019
0.8372 Intermediate Similarity NPC474949
0.837 Intermediate Similarity NPC187761
0.837 Intermediate Similarity NPC83895
0.8353 Intermediate Similarity NPC474776
0.8333 Intermediate Similarity NPC474035
0.8333 Intermediate Similarity NPC81386
0.8315 Intermediate Similarity NPC329952
0.8295 Intermediate Similarity NPC212598
0.8276 Intermediate Similarity NPC474765
0.8256 Intermediate Similarity NPC304509
0.8256 Intermediate Similarity NPC47958
0.8256 Intermediate Similarity NPC21469
0.8256 Intermediate Similarity NPC149725
0.8242 Intermediate Similarity NPC272050
0.8242 Intermediate Similarity NPC270013
0.8242 Intermediate Similarity NPC14961
0.8202 Intermediate Similarity NPC473448
0.8193 Intermediate Similarity NPC469617
0.8182 Intermediate Similarity NPC177629
0.8182 Intermediate Similarity NPC58219
0.8172 Intermediate Similarity NPC308567
0.8172 Intermediate Similarity NPC255592
0.8172 Intermediate Similarity NPC261377
0.8161 Intermediate Similarity NPC476015
0.8161 Intermediate Similarity NPC116575
0.8161 Intermediate Similarity NPC474762
0.8152 Intermediate Similarity NPC476315
0.814 Intermediate Similarity NPC475963
0.814 Intermediate Similarity NPC3464
0.814 Intermediate Similarity NPC151176
0.8111 Intermediate Similarity NPC475972
0.809 Intermediate Similarity NPC92974
0.809 Intermediate Similarity NPC474032
0.8085 Intermediate Similarity NPC475053
0.8068 Intermediate Similarity NPC186148
0.8046 Intermediate Similarity NPC197903
0.8046 Intermediate Similarity NPC261380
0.8046 Intermediate Similarity NPC99395
0.8025 Intermediate Similarity NPC160540
0.8023 Intermediate Similarity NPC53867
0.8022 Intermediate Similarity NPC476049
0.8021 Intermediate Similarity NPC472747
0.8021 Intermediate Similarity NPC472750
0.8 Intermediate Similarity NPC265856
0.8 Intermediate Similarity NPC77337
0.8 Intermediate Similarity NPC166554
0.7976 Intermediate Similarity NPC470244
0.7976 Intermediate Similarity NPC470239
0.7955 Intermediate Similarity NPC469483
0.7955 Intermediate Similarity NPC122502
0.7955 Intermediate Similarity NPC311163
0.7952 Intermediate Similarity NPC40049
0.7938 Intermediate Similarity NPC472748
0.7912 Intermediate Similarity NPC303697
0.7889 Intermediate Similarity NPC295312
0.7889 Intermediate Similarity NPC173926
0.7889 Intermediate Similarity NPC106040
0.7889 Intermediate Similarity NPC83423
0.7889 Intermediate Similarity NPC115179
0.7889 Intermediate Similarity NPC474951
0.7882 Intermediate Similarity NPC474981
0.7865 Intermediate Similarity NPC179659
0.7865 Intermediate Similarity NPC231889
0.7857 Intermediate Similarity NPC472751
0.7857 Intermediate Similarity NPC472749
0.7857 Intermediate Similarity NPC127526
0.7841 Intermediate Similarity NPC100921
0.7841 Intermediate Similarity NPC471494
0.7841 Intermediate Similarity NPC474369
0.7841 Intermediate Similarity NPC11804
0.7841 Intermediate Similarity NPC182383
0.7841 Intermediate Similarity NPC477018
0.7841 Intermediate Similarity NPC255307
0.7835 Intermediate Similarity NPC472755
0.7826 Intermediate Similarity NPC162205
0.7826 Intermediate Similarity NPC320089
0.7826 Intermediate Similarity NPC469692
0.7826 Intermediate Similarity NPC295204
0.7826 Intermediate Similarity NPC273579
0.7826 Intermediate Similarity NPC469645
0.7826 Intermediate Similarity NPC288240
0.7816 Intermediate Similarity NPC44261
0.7816 Intermediate Similarity NPC52609
0.7816 Intermediate Similarity NPC170377
0.7816 Intermediate Similarity NPC1761
0.7812 Intermediate Similarity NPC46998
0.7812 Intermediate Similarity NPC185141
0.7812 Intermediate Similarity NPC476270
0.7812 Intermediate Similarity NPC110443
0.7812 Intermediate Similarity NPC472753
0.7812 Intermediate Similarity NPC128733
0.7812 Intermediate Similarity NPC133907
0.7802 Intermediate Similarity NPC473619
0.7802 Intermediate Similarity NPC475748
0.7791 Intermediate Similarity NPC325031
0.7791 Intermediate Similarity NPC474894
0.7789 Intermediate Similarity NPC473326
0.7778 Intermediate Similarity NPC476704
0.7766 Intermediate Similarity NPC473859
0.7753 Intermediate Similarity NPC477010
0.7753 Intermediate Similarity NPC112685
0.7753 Intermediate Similarity NPC234038
0.7753 Intermediate Similarity NPC309211
0.7753 Intermediate Similarity NPC261721
0.7753 Intermediate Similarity NPC47937
0.7753 Intermediate Similarity NPC150755
0.7753 Intermediate Similarity NPC475461
0.7753 Intermediate Similarity NPC305475
0.775 Intermediate Similarity NPC101622
0.7742 Intermediate Similarity NPC303942
0.7742 Intermediate Similarity NPC121825
0.7742 Intermediate Similarity NPC469632
0.7742 Intermediate Similarity NPC65829
0.7742 Intermediate Similarity NPC57405
0.7738 Intermediate Similarity NPC470240
0.7738 Intermediate Similarity NPC7563
0.7738 Intermediate Similarity NPC116177
0.7738 Intermediate Similarity NPC476794
0.7738 Intermediate Similarity NPC320630
0.7732 Intermediate Similarity NPC474747
0.7732 Intermediate Similarity NPC472754
0.7732 Intermediate Similarity NPC473596
0.7727 Intermediate Similarity NPC114979
0.7727 Intermediate Similarity NPC14575
0.7727 Intermediate Similarity NPC196487
0.7727 Intermediate Similarity NPC191476
0.7717 Intermediate Similarity NPC219874
0.7717 Intermediate Similarity NPC473321
0.7708 Intermediate Similarity NPC288876
0.7701 Intermediate Similarity NPC473780
0.7701 Intermediate Similarity NPC473529
0.7701 Intermediate Similarity NPC11332
0.7701 Intermediate Similarity NPC94875
0.7701 Intermediate Similarity NPC180363
0.7701 Intermediate Similarity NPC474252
0.7701 Intermediate Similarity NPC475936
0.7701 Intermediate Similarity NPC131002
0.7701 Intermediate Similarity NPC473712
0.7701 Intermediate Similarity NPC145914
0.7701 Intermediate Similarity NPC65930
0.7701 Intermediate Similarity NPC73310
0.7701 Intermediate Similarity NPC475159
0.7701 Intermediate Similarity NPC85772
0.7701 Intermediate Similarity NPC329829
0.7692 Intermediate Similarity NPC473564
0.7692 Intermediate Similarity NPC151770
0.7684 Intermediate Similarity NPC474977
0.7674 Intermediate Similarity NPC200446
0.7674 Intermediate Similarity NPC472948
0.7667 Intermediate Similarity NPC159750
0.7667 Intermediate Similarity NPC473995
0.7667 Intermediate Similarity NPC190753
0.7667 Intermediate Similarity NPC86005
0.7667 Intermediate Similarity NPC154097
0.7667 Intermediate Similarity NPC473649
0.7667 Intermediate Similarity NPC470401
0.766 Intermediate Similarity NPC472469
0.766 Intermediate Similarity NPC107476
0.766 Intermediate Similarity NPC475659
0.7654 Intermediate Similarity NPC4299
0.7653 Intermediate Similarity NPC475945
0.7653 Intermediate Similarity NPC475871
0.7647 Intermediate Similarity NPC11796
0.7647 Intermediate Similarity NPC474341

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC9868 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
0.8202 Intermediate Similarity NPD6698 Approved
0.8202 Intermediate Similarity NPD46 Approved
0.7527 Intermediate Similarity NPD7983 Approved
0.75 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6101 Approved
0.7444 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD7838 Discovery
0.7353 Intermediate Similarity NPD6686 Approved
0.734 Intermediate Similarity NPD6411 Approved
0.7303 Intermediate Similarity NPD6435 Approved
0.7292 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD5779 Approved
0.7263 Intermediate Similarity NPD5778 Approved
0.7245 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7154 Phase 3
0.716 Intermediate Similarity NPD7331 Phase 2
0.7111 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD5368 Approved
0.7071 Intermediate Similarity NPD4225 Approved
0.7053 Intermediate Similarity NPD5785 Approved
0.7048 Intermediate Similarity NPD6371 Approved
0.7041 Intermediate Similarity NPD7839 Suspended
0.7037 Intermediate Similarity NPD7341 Phase 2
0.7033 Intermediate Similarity NPD5362 Discontinued
0.7 Intermediate Similarity NPD5369 Approved
0.6989 Remote Similarity NPD6422 Discontinued
0.6989 Remote Similarity NPD5786 Approved
0.6981 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6931 Remote Similarity NPD5344 Discontinued
0.6914 Remote Similarity NPD3197 Phase 1
0.6897 Remote Similarity NPD8039 Approved
0.6882 Remote Similarity NPD5363 Approved
0.6882 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6854 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6829 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6818 Remote Similarity NPD7115 Discovery
0.6759 Remote Similarity NPD8297 Approved
0.6759 Remote Similarity NPD6053 Discontinued
0.6739 Remote Similarity NPD4270 Approved
0.6739 Remote Similarity NPD4269 Approved
0.6733 Remote Similarity NPD7638 Approved
0.6703 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6703 Remote Similarity NPD4821 Approved
0.6703 Remote Similarity NPD4819 Approved
0.6703 Remote Similarity NPD4820 Approved
0.6703 Remote Similarity NPD4822 Approved
0.6702 Remote Similarity NPD1694 Approved
0.6698 Remote Similarity NPD6881 Approved
0.6698 Remote Similarity NPD6899 Approved
0.6698 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7639 Approved
0.6667 Remote Similarity NPD5739 Approved
0.6667 Remote Similarity NPD7748 Approved
0.6667 Remote Similarity NPD6675 Approved
0.6667 Remote Similarity NPD7640 Approved
0.6667 Remote Similarity NPD6402 Approved
0.6667 Remote Similarity NPD7128 Approved
0.6638 Remote Similarity NPD7507 Approved
0.6634 Remote Similarity NPD6083 Phase 2
0.6634 Remote Similarity NPD6084 Phase 2
0.6633 Remote Similarity NPD7515 Phase 2
0.6604 Remote Similarity NPD5697 Approved
0.6598 Remote Similarity NPD1695 Approved
0.6579 Remote Similarity NPD8513 Phase 3
0.6579 Remote Similarity NPD8516 Approved
0.6579 Remote Similarity NPD8517 Approved
0.6579 Remote Similarity NPD8515 Approved
0.6574 Remote Similarity NPD7290 Approved
0.6574 Remote Similarity NPD7102 Approved
0.6574 Remote Similarity NPD6883 Approved
0.6566 Remote Similarity NPD6399 Phase 3
0.6562 Remote Similarity NPD3573 Approved
0.6545 Remote Similarity NPD4632 Approved
0.6542 Remote Similarity NPD6011 Approved
0.6542 Remote Similarity NPD7320 Approved
0.6522 Remote Similarity NPD4252 Approved
0.6514 Remote Similarity NPD6649 Approved
0.6514 Remote Similarity NPD6847 Approved
0.6514 Remote Similarity NPD6650 Approved
0.6514 Remote Similarity NPD8130 Phase 1
0.6514 Remote Similarity NPD6617 Approved
0.6514 Remote Similarity NPD6869 Approved
0.6506 Remote Similarity NPD7909 Approved
0.6505 Remote Similarity NPD6648 Approved
0.6489 Remote Similarity NPD5332 Approved
0.6489 Remote Similarity NPD6110 Phase 1
0.6489 Remote Similarity NPD5331 Approved
0.6484 Remote Similarity NPD4271 Approved
0.6484 Remote Similarity NPD4268 Approved
0.6481 Remote Similarity NPD6014 Approved
0.6481 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6481 Remote Similarity NPD6373 Approved
0.6481 Remote Similarity NPD6013 Approved
0.6481 Remote Similarity NPD6012 Approved
0.6481 Remote Similarity NPD6372 Approved
0.6471 Remote Similarity NPD7319 Approved
0.6471 Remote Similarity NPD7902 Approved
0.6466 Remote Similarity NPD7830 Approved
0.6466 Remote Similarity NPD7642 Approved
0.6466 Remote Similarity NPD7829 Approved
0.6465 Remote Similarity NPD6079 Approved
0.646 Remote Similarity NPD7641 Discontinued
0.6458 Remote Similarity NPD7521 Approved
0.6458 Remote Similarity NPD5330 Approved
0.6458 Remote Similarity NPD6684 Approved
0.6458 Remote Similarity NPD7146 Approved
0.6458 Remote Similarity NPD7334 Approved
0.6458 Remote Similarity NPD6409 Approved
0.6455 Remote Similarity NPD6882 Approved
0.6452 Remote Similarity NPD4790 Discontinued
0.6449 Remote Similarity NPD6412 Phase 2
0.6449 Remote Similarity NPD5701 Approved
0.6436 Remote Similarity NPD5695 Phase 3
0.6429 Remote Similarity NPD5328 Approved
0.6421 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6383 Remote Similarity NPD5209 Approved
0.6383 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6374 Remote Similarity NPD4756 Discovery
0.6364 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6364 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6356 Remote Similarity NPD8451 Approved
0.6348 Remote Similarity NPD6319 Approved
0.6337 Remote Similarity NPD5282 Discontinued
0.6327 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6327 Remote Similarity NPD6672 Approved
0.6327 Remote Similarity NPD5737 Approved
0.6327 Remote Similarity NPD6903 Approved
0.6303 Remote Similarity NPD8448 Approved
0.6303 Remote Similarity NPD8074 Phase 3
0.63 Remote Similarity NPD5693 Phase 1
0.6293 Remote Similarity NPD8444 Approved
0.6279 Remote Similarity NPD4247 Clinical (unspecified phase)
0.625 Remote Similarity NPD4786 Approved
0.625 Remote Similarity NPD3665 Phase 1
0.625 Remote Similarity NPD8133 Approved
0.625 Remote Similarity NPD5696 Approved
0.625 Remote Similarity NPD3666 Approved
0.625 Remote Similarity NPD3133 Approved
0.624 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6228 Remote Similarity NPD6009 Approved
0.6226 Remote Similarity NPD5211 Phase 2
0.6224 Remote Similarity NPD4250 Approved
0.6224 Remote Similarity NPD7524 Approved
0.6224 Remote Similarity NPD4251 Approved
0.6218 Remote Similarity NPD8273 Phase 1
0.6214 Remote Similarity NPD4792 Clinical (unspecified phase)
0.6214 Remote Similarity NPD5221 Approved
0.6214 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6214 Remote Similarity NPD5222 Approved
0.6211 Remote Similarity NPD3667 Approved
0.6203 Remote Similarity NPD3195 Phase 2
0.6203 Remote Similarity NPD3728 Approved
0.6203 Remote Similarity NPD3194 Approved
0.6203 Remote Similarity NPD4266 Approved
0.6203 Remote Similarity NPD3196 Approved
0.6203 Remote Similarity NPD3730 Approved
0.619 Remote Similarity NPD5285 Approved
0.619 Remote Similarity NPD5286 Approved
0.619 Remote Similarity NPD4696 Approved
0.6186 Remote Similarity NPD8328 Phase 3
0.6186 Remote Similarity NPD7604 Phase 2
0.6176 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6176 Remote Similarity NPD7900 Approved
0.6174 Remote Similarity NPD6335 Approved
0.617 Remote Similarity NPD4695 Discontinued
0.6154 Remote Similarity NPD5173 Approved
0.6154 Remote Similarity NPD4755 Approved
0.6154 Remote Similarity NPD5983 Phase 2
0.6148 Remote Similarity NPD8392 Approved
0.6148 Remote Similarity NPD8391 Approved
0.6148 Remote Similarity NPD8390 Approved
0.6145 Remote Similarity NPD4246 Clinical (unspecified phase)
0.614 Remote Similarity NPD6274 Approved
0.614 Remote Similarity NPD6868 Approved
0.6139 Remote Similarity NPD7637 Suspended
0.6139 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6134 Remote Similarity NPD8340 Approved
0.6134 Remote Similarity NPD8341 Approved
0.6134 Remote Similarity NPD8342 Approved
0.6134 Remote Similarity NPD7492 Approved
0.6134 Remote Similarity NPD8299 Approved
0.6132 Remote Similarity NPD5223 Approved
0.6126 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6122 Remote Similarity NPD3618 Phase 1
0.6122 Remote Similarity NPD4249 Approved
0.6122 Remote Similarity NPD5279 Phase 3
0.6121 Remote Similarity NPD7100 Approved
0.6121 Remote Similarity NPD7101 Approved
0.6111 Remote Similarity NPD5141 Approved
0.61 Remote Similarity NPD6051 Approved
0.61 Remote Similarity NPD6080 Approved
0.61 Remote Similarity NPD6673 Approved
0.61 Remote Similarity NPD5370 Suspended
0.61 Remote Similarity NPD4753 Phase 2
0.61 Remote Similarity NPD6904 Approved
0.6098 Remote Similarity NPD6109 Phase 1
0.6098 Remote Similarity NPD7260 Phase 2
0.6087 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6087 Remote Similarity NPD6317 Approved

Structure

External Identifiers

PubChem CID   21774929
ChEMBL   CHEMBL470131
ZINC  

Physicochemical Properties

Molecular Weight:  352.22
ALogP:  0.9088
MLogP:  3.11
XLogP:  2.468
# Rotatable Bonds:  6
Polar Surface Area:  86.99
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  25

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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