Natural Product: NPC469645

Natural Product ID:  NPC469645
Common Name:   Gyrosanolide B
IUPAC Name:  
Synonyms:  
Molecular Formula:   C19H24O6
Standard InCHIKey:  GXIMRISCJWUCIN-YIHVGUCGSA-N
Standard InCHI:  InChI=1S/C19H24O6/c1-10(2)12-4-5-14-18(23)17(25-19(14)24)7-11(3)6-15(21)16(22)9-13(20)8-12/h5-6,12,16-18,22-23H,1,4,7-9H2,2-3H3/b11-6-,14-5-/t12-,16-,17+,18-/m0/s1
Canonical SMILES:  O=C1C[C@H](C/C=C/2C(=O)O[C@@H]([C@H]2O)C/C(=CC(=O)[C@H](C1)O)/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
NPO23707 Sinularia gyrosa Species Alcyoniidae Eukaryota PMID[20430633]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1750 Organism Human herpesvirus 5 Human herpesvirus 5 ED50 > 50 ug/ml 14518939
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 18.6 % 12398531
NPT81 Cell Line A549 Homo sapiens ED50 > 20 ug/ml 9214729
NPT139 Cell Line HT-29 Homo sapiens ED50 > 20 ug/ml 26200131
NPT168 Cell Line P388 Mus musculus ED50 > 20 ug/ml 21966980

  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 NPC469645 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
1.0 High Similarity NPC469692
0.9885 High Similarity NPC121825
0.9247 High Similarity NPC128733
0.9247 High Similarity NPC185141
0.9247 High Similarity NPC110443
0.9247 High Similarity NPC46998
0.9247 High Similarity NPC133907
0.908 High Similarity NPC261721
0.8804 High Similarity NPC469632
0.8696 High Similarity NPC475302
0.8667 High Similarity NPC476803
0.866 High Similarity NPC475871
0.866 High Similarity NPC472755
0.866 High Similarity NPC475945
0.8652 High Similarity NPC469910
0.8652 High Similarity NPC475461
0.8652 High Similarity NPC305475
0.8646 High Similarity NPC474339
0.8646 High Similarity NPC474742
0.8646 High Similarity NPC164598
0.8557 High Similarity NPC149371
0.8557 High Similarity NPC474747
0.8539 High Similarity NPC165162
0.8539 High Similarity NPC470755
0.8539 High Similarity NPC255307
0.8495 Intermediate Similarity NPC273579
0.8495 Intermediate Similarity NPC295204
0.8495 Intermediate Similarity NPC162205
0.8495 Intermediate Similarity NPC475912
0.8495 Intermediate Similarity NPC288240
0.8478 Intermediate Similarity NPC474232
0.8469 Intermediate Similarity NPC475873
0.8462 Intermediate Similarity NPC476805
0.8454 Intermediate Similarity NPC47880
0.8454 Intermediate Similarity NPC472753
0.8444 Intermediate Similarity NPC279859
0.8444 Intermediate Similarity NPC38576
0.8444 Intermediate Similarity NPC469483
0.8438 Intermediate Similarity NPC471144
0.8427 Intermediate Similarity NPC158756
0.8427 Intermediate Similarity NPC114979
0.8427 Intermediate Similarity NPC141193
0.8427 Intermediate Similarity NPC191476
0.8427 Intermediate Similarity NPC96259
0.8387 Intermediate Similarity NPC111114
0.8387 Intermediate Similarity NPC261607
0.8387 Intermediate Similarity NPC300312
0.8384 Intermediate Similarity NPC474741
0.8384 Intermediate Similarity NPC472756
0.8384 Intermediate Similarity NPC100487
0.8372 Intermediate Similarity NPC93763
0.8372 Intermediate Similarity NPC108816
0.8367 Intermediate Similarity NPC471148
0.8367 Intermediate Similarity NPC472754
0.8352 Intermediate Similarity NPC472007
0.8351 Intermediate Similarity NPC288876
0.8333 Intermediate Similarity NPC261380
0.8333 Intermediate Similarity NPC21469
0.8316 Intermediate Similarity NPC471142
0.8316 Intermediate Similarity NPC36954
0.8316 Intermediate Similarity NPC270013
0.8316 Intermediate Similarity NPC14961
0.8315 Intermediate Similarity NPC475947
0.8315 Intermediate Similarity NPC473390
0.8315 Intermediate Similarity NPC40746
0.8315 Intermediate Similarity NPC131669
0.8315 Intermediate Similarity NPC169575
0.828 Intermediate Similarity NPC129419
0.828 Intermediate Similarity NPC476004
0.828 Intermediate Similarity NPC474761
0.8265 Intermediate Similarity NPC201718
0.8265 Intermediate Similarity NPC476270
0.8261 Intermediate Similarity NPC469628
0.8261 Intermediate Similarity NPC471047
0.8261 Intermediate Similarity NPC469653
0.8261 Intermediate Similarity NPC475819
0.8261 Intermediate Similarity NPC469631
0.8261 Intermediate Similarity NPC475906
0.8256 Intermediate Similarity NPC320630
0.8256 Intermediate Similarity NPC116177
0.8256 Intermediate Similarity NPC7563
0.8247 Intermediate Similarity NPC141191
0.8247 Intermediate Similarity NPC187268
0.8242 Intermediate Similarity NPC150755
0.8242 Intermediate Similarity NPC472009
0.8235 Intermediate Similarity NPC38154
0.8229 Intermediate Similarity NPC477921
0.8229 Intermediate Similarity NPC279621
0.8229 Intermediate Similarity NPC230800
0.8222 Intermediate Similarity NPC476804
0.8218 Intermediate Similarity NPC477513
0.8211 Intermediate Similarity NPC167219
0.8211 Intermediate Similarity NPC474035
0.8211 Intermediate Similarity NPC81386
0.8202 Intermediate Similarity NPC229825
0.8202 Intermediate Similarity NPC474291
0.82 Intermediate Similarity NPC203659
0.8191 Intermediate Similarity NPC476705
0.8191 Intermediate Similarity NPC473321
0.8191 Intermediate Similarity NPC30515
0.8191 Intermediate Similarity NPC184463
0.8172 Intermediate Similarity NPC295312
0.8172 Intermediate Similarity NPC268298
0.8172 Intermediate Similarity NPC474032
0.8152 Intermediate Similarity NPC179659
0.8152 Intermediate Similarity NPC72513
0.8144 Intermediate Similarity NPC169205
0.8132 Intermediate Similarity NPC11804
0.8132 Intermediate Similarity NPC125290
0.8125 Intermediate Similarity NPC477922
0.8105 Intermediate Similarity NPC125674
0.8105 Intermediate Similarity NPC212486
0.8105 Intermediate Similarity NPC475838
0.8105 Intermediate Similarity NPC179746
0.8105 Intermediate Similarity NPC228451
0.8105 Intermediate Similarity NPC476300
0.8105 Intermediate Similarity NPC81419
0.81 Intermediate Similarity NPC110989
0.809 Intermediate Similarity NPC24417
0.809 Intermediate Similarity NPC281949
0.809 Intermediate Similarity NPC301477
0.809 Intermediate Similarity NPC25684
0.809 Intermediate Similarity NPC471325
0.8085 Intermediate Similarity NPC469368
0.8085 Intermediate Similarity NPC71533
0.8085 Intermediate Similarity NPC179394
0.8085 Intermediate Similarity NPC475855
0.8085 Intermediate Similarity NPC51004
0.8085 Intermediate Similarity NPC106510
0.8085 Intermediate Similarity NPC473619
0.8085 Intermediate Similarity NPC144133
0.8085 Intermediate Similarity NPC473448
0.8068 Intermediate Similarity NPC19841
0.8068 Intermediate Similarity NPC178277
0.8068 Intermediate Similarity NPC470239
0.8068 Intermediate Similarity NPC470244
0.8065 Intermediate Similarity NPC202672
0.8065 Intermediate Similarity NPC472008
0.8061 Intermediate Similarity NPC159763
0.8061 Intermediate Similarity NPC278386
0.8061 Intermediate Similarity NPC124512
0.8061 Intermediate Similarity NPC161855
0.8041 Intermediate Similarity NPC476009
0.8041 Intermediate Similarity NPC473859
0.8041 Intermediate Similarity NPC76862
0.8041 Intermediate Similarity NPC476315
0.8041 Intermediate Similarity NPC158416
0.8041 Intermediate Similarity NPC185553
0.8041 Intermediate Similarity NPC473291
0.8041 Intermediate Similarity NPC39859
0.8041 Intermediate Similarity NPC470883
0.8039 Intermediate Similarity NPC469853
0.8039 Intermediate Similarity NPC26617
0.8022 Intermediate Similarity NPC243618
0.8022 Intermediate Similarity NPC70424
0.8021 Intermediate Similarity NPC474247
0.8021 Intermediate Similarity NPC65829
0.802 Intermediate Similarity NPC220964
0.802 Intermediate Similarity NPC475676
0.8 Intermediate Similarity NPC85772
0.8 Intermediate Similarity NPC475690
0.8 Intermediate Similarity NPC39996
0.8 Intermediate Similarity NPC189609
0.8 Intermediate Similarity NPC140591
0.8 Intermediate Similarity NPC12172
0.8 Intermediate Similarity NPC197835
0.8 Intermediate Similarity NPC291500
0.8 Intermediate Similarity NPC225353
0.8 Intermediate Similarity NPC303653
0.8 Intermediate Similarity NPC208886
0.8 Intermediate Similarity NPC11383
0.8 Intermediate Similarity NPC474959
0.8 Intermediate Similarity NPC310450
0.8 Intermediate Similarity NPC320019
0.8 Intermediate Similarity NPC86077
0.8 Intermediate Similarity NPC475046
0.8 Intermediate Similarity NPC89555
0.8 Intermediate Similarity NPC324017
0.798 Intermediate Similarity NPC475949
0.7979 Intermediate Similarity NPC130359
0.7979 Intermediate Similarity NPC218927
0.7979 Intermediate Similarity NPC14901
0.7979 Intermediate Similarity NPC307411
0.7979 Intermediate Similarity NPC206001
0.7959 Intermediate Similarity NPC474313
0.7959 Intermediate Similarity NPC40812
0.7957 Intermediate Similarity NPC160138
0.7957 Intermediate Similarity NPC266957
0.7955 Intermediate Similarity NPC11796
0.7955 Intermediate Similarity NPC128276
0.7955 Intermediate Similarity NPC196653
0.7955 Intermediate Similarity NPC267231
0.7955 Intermediate Similarity NPC471465
0.7955 Intermediate Similarity NPC218817
0.7941 Intermediate Similarity NPC469852
0.7941 Intermediate Similarity NPC472749
0.7941 Intermediate Similarity NPC472751
0.7938 Intermediate Similarity NPC48803
0.7938 Intermediate Similarity NPC471141
0.7938 Intermediate Similarity NPC275960

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC469645 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
0.8061 Intermediate Similarity NPD4225 Approved
0.8039 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7938 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD5785 Approved
0.781 Intermediate Similarity NPD6371 Approved
0.7742 Intermediate Similarity NPD5363 Approved
0.7708 Intermediate Similarity NPD46 Approved
0.7708 Intermediate Similarity NPD6698 Approved
0.7474 Intermediate Similarity NPD5786 Approved
0.7449 Intermediate Similarity NPD7983 Approved
0.7419 Intermediate Similarity NPD4270 Approved
0.7419 Intermediate Similarity NPD4269 Approved
0.7387 Intermediate Similarity NPD7115 Discovery
0.7347 Intermediate Similarity NPD7838 Discovery
0.734 Intermediate Similarity NPD7154 Phase 3
0.7248 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD4252 Approved
0.7188 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD5282 Discontinued
0.7128 Intermediate Similarity NPD5369 Approved
0.703 Intermediate Similarity NPD5779 Approved
0.703 Intermediate Similarity NPD5778 Approved
0.7019 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.701 Intermediate Similarity NPD1694 Approved
0.6979 Remote Similarity NPD5362 Discontinued
0.6972 Remote Similarity NPD6686 Approved
0.6882 Remote Similarity NPD4756 Discovery
0.6875 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5209 Approved
0.6875 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6809 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6733 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6733 Remote Similarity NPD5370 Suspended
0.6733 Remote Similarity NPD1695 Approved
0.6733 Remote Similarity NPD6101 Approved
0.6729 Remote Similarity NPD5344 Discontinued
0.6701 Remote Similarity NPD6435 Approved
0.6667 Remote Similarity NPD7839 Suspended
0.6667 Remote Similarity NPD4821 Approved
0.6667 Remote Similarity NPD4819 Approved
0.6667 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4820 Approved
0.6667 Remote Similarity NPD4822 Approved
0.6633 Remote Similarity NPD6110 Phase 1
0.6632 Remote Similarity NPD4268 Approved
0.6632 Remote Similarity NPD4271 Approved
0.6604 Remote Similarity NPD6084 Phase 2
0.6604 Remote Similarity NPD6083 Phase 2
0.6602 Remote Similarity NPD6411 Approved
0.6602 Remote Similarity NPD4810 Clinical (unspecified phase)
0.66 Remote Similarity NPD4249 Approved
0.6571 Remote Similarity NPD5695 Phase 3
0.6566 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6555 Remote Similarity NPD8517 Approved
0.6555 Remote Similarity NPD8513 Phase 3
0.6555 Remote Similarity NPD8515 Approved
0.6555 Remote Similarity NPD8516 Approved
0.6542 Remote Similarity NPD5696 Approved
0.6538 Remote Similarity NPD6399 Phase 3
0.6535 Remote Similarity NPD4250 Approved
0.6535 Remote Similarity NPD4251 Approved
0.6495 Remote Similarity NPD5368 Approved
0.6491 Remote Similarity NPD6650 Approved
0.6491 Remote Similarity NPD6649 Approved
0.6484 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6481 Remote Similarity NPD7640 Approved
0.6481 Remote Similarity NPD7639 Approved
0.6477 Remote Similarity NPD3197 Phase 1
0.6471 Remote Similarity NPD6319 Approved
0.6465 Remote Similarity NPD5331 Approved
0.6465 Remote Similarity NPD5332 Approved
0.646 Remote Similarity NPD6372 Approved
0.646 Remote Similarity NPD6373 Approved
0.6442 Remote Similarity NPD7637 Suspended
0.6435 Remote Similarity NPD8297 Approved
0.6429 Remote Similarity NPD4790 Discontinued
0.6429 Remote Similarity NPD5697 Approved
0.6404 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6389 Remote Similarity NPD7638 Approved
0.6372 Remote Similarity NPD6899 Approved
0.6372 Remote Similarity NPD6881 Approved
0.6372 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6355 Remote Similarity NPD4792 Clinical (unspecified phase)
0.6348 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6339 Remote Similarity NPD6675 Approved
0.6339 Remote Similarity NPD7128 Approved
0.6339 Remote Similarity NPD6402 Approved
0.6339 Remote Similarity NPD5739 Approved
0.633 Remote Similarity NPD6648 Approved
0.6327 Remote Similarity NPD4695 Discontinued
0.6316 Remote Similarity NPD6012 Approved
0.6316 Remote Similarity NPD6013 Approved
0.6316 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6316 Remote Similarity NPD6014 Approved
0.6311 Remote Similarity NPD5737 Approved
0.6311 Remote Similarity NPD7642 Approved
0.6311 Remote Similarity NPD6672 Approved
0.6296 Remote Similarity NPD7902 Approved
0.6293 Remote Similarity NPD6053 Discontinued
0.629 Remote Similarity NPD8074 Phase 3
0.6286 Remote Similarity NPD5693 Phase 1
0.6283 Remote Similarity NPD5701 Approved
0.6275 Remote Similarity NPD5279 Phase 3
0.6262 Remote Similarity NPD4629 Approved
0.6262 Remote Similarity NPD5210 Approved
0.6261 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6261 Remote Similarity NPD7102 Approved
0.6261 Remote Similarity NPD6883 Approved
0.6261 Remote Similarity NPD7290 Approved
0.626 Remote Similarity NPD7492 Approved
0.625 Remote Similarity NPD4753 Phase 2
0.6239 Remote Similarity NPD4632 Approved
0.6228 Remote Similarity NPD7320 Approved
0.6228 Remote Similarity NPD6011 Approved
0.6216 Remote Similarity NPD5211 Phase 2
0.621 Remote Similarity NPD6616 Approved
0.6207 Remote Similarity NPD6869 Approved
0.6207 Remote Similarity NPD6847 Approved
0.6207 Remote Similarity NPD2204 Approved
0.6207 Remote Similarity NPD8130 Phase 1
0.6207 Remote Similarity NPD6617 Approved
0.6204 Remote Similarity NPD4697 Phase 3
0.6198 Remote Similarity NPD6054 Approved
0.618 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6179 Remote Similarity NPD8328 Phase 3
0.6179 Remote Similarity NPD7830 Approved
0.6179 Remote Similarity NPD7829 Approved
0.6168 Remote Similarity NPD7748 Approved
0.616 Remote Similarity NPD7078 Approved
0.6154 Remote Similarity NPD3704 Approved
0.6154 Remote Similarity NPD6882 Approved
0.6148 Remote Similarity NPD6015 Approved
0.6148 Remote Similarity NPD6016 Approved
0.6146 Remote Similarity NPD8039 Approved
0.614 Remote Similarity NPD6412 Phase 2
0.6132 Remote Similarity NPD7515 Phase 2
0.6121 Remote Similarity NPD2067 Discontinued
0.6121 Remote Similarity NPD4634 Approved
0.6117 Remote Similarity NPD6409 Approved
0.6117 Remote Similarity NPD7146 Approved
0.6117 Remote Similarity NPD7334 Approved
0.6117 Remote Similarity NPD6684 Approved
0.6117 Remote Similarity NPD5330 Approved
0.6117 Remote Similarity NPD3618 Phase 1
0.6117 Remote Similarity NPD7521 Approved
0.6111 Remote Similarity NPD7736 Approved
0.6106 Remote Similarity NPD5141 Approved
0.6098 Remote Similarity NPD5988 Approved
0.6098 Remote Similarity NPD6370 Approved
0.6094 Remote Similarity NPD7260 Phase 2
0.6083 Remote Similarity NPD7500 Approved
0.608 Remote Similarity NPD8273 Phase 1
0.6078 Remote Similarity NPD3133 Approved
0.6078 Remote Similarity NPD3665 Phase 1
0.6078 Remote Similarity NPD3666 Approved
0.6066 Remote Similarity NPD7299 Clinical (unspecified phase)
0.6066 Remote Similarity NPD6059 Approved
0.6063 Remote Similarity NPD7319 Approved
0.6055 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6055 Remote Similarity NPD5222 Approved
0.6055 Remote Similarity NPD5221 Approved
0.604 Remote Similarity NPD3667 Approved
0.6036 Remote Similarity NPD4696 Approved
0.6036 Remote Similarity NPD5285 Approved
0.6036 Remote Similarity NPD5286 Approved
0.6033 Remote Similarity NPD7641 Discontinued
0.6032 Remote Similarity NPD8293 Discontinued
0.6019 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6019 Remote Similarity NPD1696 Phase 3
0.6019 Remote Similarity NPD7900 Approved
0.6018 Remote Similarity NPD6647 Phase 2
0.6016 Remote Similarity NPD8444 Approved
0.6 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6 Remote Similarity NPD5173 Approved
0.6 Remote Similarity NPD6274 Approved
0.6 Remote Similarity NPD2629 Approved
0.6 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6 Remote Similarity NPD6903 Approved
0.6 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6 Remote Similarity NPD4755 Approved
0.5978 Remote Similarity NPD7331 Phase 2
0.5968 Remote Similarity NPD8080 Discontinued
0.5962 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5952 Remote Similarity NPD8451 Approved
0.5952 Remote Similarity NPD7507 Approved
0.595 Remote Similarity NPD6009 Approved
0.595 Remote Similarity NPD7505 Discontinued
0.5943 Remote Similarity NPD6904 Approved
0.5943 Remote Similarity NPD6673 Approved
0.5943 Remote Similarity NPD6080 Approved
0.5943 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5932 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5929 Remote Similarity NPD5226 Approved
0.5929 Remote Similarity NPD7632 Discontinued
0.5929 Remote Similarity NPD5224 Approved
0.5929 Remote Similarity NPD5225 Approved
0.5929 Remote Similarity NPD4633 Approved
0.5923 Remote Similarity NPD6845 Suspended
0.5922 Remote Similarity NPD4786 Approved

Structure

External Identifiers

PubChem CID  
ChEMBL   CHEMBL1096137
ZINC  

Physicochemical Properties

Molecular Weight:  348.16
ALogP:  0.3247
MLogP:  2.89
XLogP:  0.477
# Rotatable Bonds:  5
Polar Surface Area:  100.9
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  25

Download Data

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