Natural Product: NPC213078

Natural Product ID:  NPC213078
Common Name:   Gaillardin
IUPAC Name:   [(3aS,5aS,6S,8R,8aR,9aR)-8-hydroxy-5,8-dimethyl-1-methylidene-2-oxo-5a,6,7,8a,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-6-yl] acetate
Synonyms:   Gaillardin
Molecular Formula:   C17H22O5
Standard InCHIKey:  UTPGJEROJZHISI-DFGCRIRUSA-N
Standard InCHI:  InChI=1S/C17H22O5/c1-8-5-13-11(9(2)16(19)22-13)6-12-15(8)14(21-10(3)18)7-17(12,4)20/h5,11-15,20H,2,6-7H2,1,3-4H3/t11-,12-,13+,14+,15-,17-/m1/s1
Canonical SMILES:  CC(=O)O[C@H]1C[C@@]([C@H]2[C@H]1C(=C[C@H]1[C@H](C2)C(=C)C(=O)O1)C)(C)O
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
NPO33469 Asteraceae Family Asteraceae Eukaryota PMID[18329753]
NPO33493 inula lineariifolia Species Asteraceae Eukaryota PMID[20515062]
NPO19076 Gaillardia pulchella Species Asteraceae Eukaryota TCM_Taiwan*
NPO31199 Jnula britannica NA NA NA TCM_Taiwan*
NPO29625 Inulae herba NA NA NA TCMSP*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT91 Cell Line KB Homo sapiens ED50 = 2.3 ug/ml 17336532
NPT91 Cell Line KB Homo sapiens ED50 = 7.52 umol/ml 18329753
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 5290 nM 20515062
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 2950 nM 20515062

  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 NPC213078 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
0.9889 High Similarity NPC161493
0.9888 High Similarity NPC67584
0.9775 High Similarity NPC127019
0.9667 High Similarity NPC213698
0.9667 High Similarity NPC52044
0.9565 High Similarity NPC221615
0.9451 High Similarity NPC170120
0.9438 High Similarity NPC301969
0.9438 High Similarity NPC37607
0.9158 High Similarity NPC150923
0.913 High Similarity NPC262133
0.913 High Similarity NPC470013
0.913 High Similarity NPC477131
0.913 High Similarity NPC323008
0.913 High Similarity NPC198853
0.913 High Similarity NPC470010
0.9121 High Similarity NPC133698
0.9011 High Similarity NPC216284
0.9 High Similarity NPC79549
0.8989 High Similarity NPC67493
0.8969 High Similarity NPC124881
0.8936 High Similarity NPC18019
0.8936 High Similarity NPC24956
0.8913 High Similarity NPC131209
0.8913 High Similarity NPC155215
0.8901 High Similarity NPC215556
0.8876 High Similarity NPC235792
0.883 High Similarity NPC472873
0.8817 High Similarity NPC258216
0.8791 High Similarity NPC224652
0.8791 High Similarity NPC91248
0.8764 High Similarity NPC156485
0.871 High Similarity NPC475925
0.871 High Similarity NPC29821
0.871 High Similarity NPC171360
0.871 High Similarity NPC35959
0.871 High Similarity NPC57304
0.871 High Similarity NPC63193
0.871 High Similarity NPC293001
0.871 High Similarity NPC133888
0.8696 High Similarity NPC472872
0.8667 High Similarity NPC300082
0.8667 High Similarity NPC204105
0.8667 High Similarity NPC284534
0.866 High Similarity NPC70865
0.8632 High Similarity NPC476053
0.8632 High Similarity NPC163228
0.8632 High Similarity NPC224689
0.8632 High Similarity NPC304886
0.8602 High Similarity NPC54065
0.8602 High Similarity NPC35809
0.8602 High Similarity NPC297474
0.86 High Similarity NPC54737
0.8587 High Similarity NPC207114
0.8587 High Similarity NPC217983
0.8571 High Similarity NPC64153
0.8511 High Similarity NPC184063
0.8495 Intermediate Similarity NPC155935
0.8495 Intermediate Similarity NPC4986
0.8485 Intermediate Similarity NPC86077
0.8478 Intermediate Similarity NPC24728
0.8469 Intermediate Similarity NPC186861
0.8454 Intermediate Similarity NPC108475
0.8454 Intermediate Similarity NPC170143
0.8454 Intermediate Similarity NPC471150
0.8454 Intermediate Similarity NPC213947
0.8444 Intermediate Similarity NPC245665
0.8438 Intermediate Similarity NPC37408
0.8421 Intermediate Similarity NPC135776
0.8416 Intermediate Similarity NPC223450
0.8416 Intermediate Similarity NPC243998
0.8404 Intermediate Similarity NPC19087
0.8387 Intermediate Similarity NPC471149
0.8387 Intermediate Similarity NPC178875
0.8384 Intermediate Similarity NPC171759
0.837 Intermediate Similarity NPC107787
0.837 Intermediate Similarity NPC187661
0.8367 Intermediate Similarity NPC45125
0.835 Intermediate Similarity NPC139838
0.835 Intermediate Similarity NPC59489
0.8333 Intermediate Similarity NPC26617
0.8333 Intermediate Similarity NPC89555
0.8333 Intermediate Similarity NPC246076
0.8333 Intermediate Similarity NPC474338
0.8318 Intermediate Similarity NPC36754
0.8317 Intermediate Similarity NPC100487
0.8298 Intermediate Similarity NPC283409
0.8298 Intermediate Similarity NPC38392
0.8283 Intermediate Similarity NPC471381
0.8283 Intermediate Similarity NPC280963
0.828 Intermediate Similarity NPC118601
0.828 Intermediate Similarity NPC160138
0.8265 Intermediate Similarity NPC181151
0.8265 Intermediate Similarity NPC477949
0.8261 Intermediate Similarity NPC165162
0.8261 Intermediate Similarity NPC78089
0.8252 Intermediate Similarity NPC117604
0.8247 Intermediate Similarity NPC469873
0.8242 Intermediate Similarity NPC111409
0.8242 Intermediate Similarity NPC250315
0.8241 Intermediate Similarity NPC161060
0.8235 Intermediate Similarity NPC166115
0.8229 Intermediate Similarity NPC472874
0.8229 Intermediate Similarity NPC473263
0.8229 Intermediate Similarity NPC81419
0.8229 Intermediate Similarity NPC473273
0.8229 Intermediate Similarity NPC475838
0.8229 Intermediate Similarity NPC308656
0.8229 Intermediate Similarity NPC475912
0.8229 Intermediate Similarity NPC179746
0.8229 Intermediate Similarity NPC476300
0.8229 Intermediate Similarity NPC60386
0.8229 Intermediate Similarity NPC228451
0.8229 Intermediate Similarity NPC125674
0.8229 Intermediate Similarity NPC473234
0.8222 Intermediate Similarity NPC25684
0.8222 Intermediate Similarity NPC281949
0.8222 Intermediate Similarity NPC301477
0.8211 Intermediate Similarity NPC144133
0.8211 Intermediate Similarity NPC475855
0.8211 Intermediate Similarity NPC51004
0.8211 Intermediate Similarity NPC179394
0.8211 Intermediate Similarity NPC129419
0.8202 Intermediate Similarity NPC182550
0.82 Intermediate Similarity NPC477950
0.8191 Intermediate Similarity NPC202672
0.8172 Intermediate Similarity NPC50637
0.8172 Intermediate Similarity NPC304558
0.8172 Intermediate Similarity NPC56593
0.8163 Intermediate Similarity NPC142529
0.8163 Intermediate Similarity NPC91771
0.8152 Intermediate Similarity NPC53011
0.8152 Intermediate Similarity NPC16887
0.8152 Intermediate Similarity NPC194859
0.8152 Intermediate Similarity NPC37005
0.8152 Intermediate Similarity NPC224386
0.8152 Intermediate Similarity NPC115786
0.8152 Intermediate Similarity NPC154893
0.8144 Intermediate Similarity NPC474247
0.8125 Intermediate Similarity NPC208886
0.8125 Intermediate Similarity NPC12172
0.8125 Intermediate Similarity NPC184463
0.8125 Intermediate Similarity NPC30515
0.8125 Intermediate Similarity NPC221282
0.8111 Intermediate Similarity NPC258965
0.8111 Intermediate Similarity NPC156658
0.8105 Intermediate Similarity NPC295312
0.8105 Intermediate Similarity NPC212664
0.8105 Intermediate Similarity NPC268298
0.8105 Intermediate Similarity NPC32922
0.8105 Intermediate Similarity NPC307411
0.8085 Intermediate Similarity NPC270270
0.8081 Intermediate Similarity NPC474313
0.8081 Intermediate Similarity NPC311904
0.8065 Intermediate Similarity NPC255307
0.8065 Intermediate Similarity NPC215364
0.8061 Intermediate Similarity NPC270013
0.8061 Intermediate Similarity NPC14961
0.8061 Intermediate Similarity NPC36954
0.8058 Intermediate Similarity NPC190867
0.8043 Intermediate Similarity NPC318468
0.8043 Intermediate Similarity NPC128246
0.8041 Intermediate Similarity NPC212486
0.8041 Intermediate Similarity NPC153590
0.8039 Intermediate Similarity NPC474775
0.8037 Intermediate Similarity NPC273242
0.8022 Intermediate Similarity NPC141810
0.8 Intermediate Similarity NPC187268
0.8 Intermediate Similarity NPC470239
0.8 Intermediate Similarity NPC470244
0.8 Intermediate Similarity NPC477102
0.798 Intermediate Similarity NPC279621
0.798 Intermediate Similarity NPC476315
0.798 Intermediate Similarity NPC126156
0.798 Intermediate Similarity NPC230800
0.7979 Intermediate Similarity NPC284902
0.7979 Intermediate Similarity NPC309757
0.7979 Intermediate Similarity NPC305475
0.7979 Intermediate Similarity NPC162071
0.7979 Intermediate Similarity NPC236692
0.7979 Intermediate Similarity NPC475461
0.7978 Intermediate Similarity NPC476794
0.7978 Intermediate Similarity NPC470240
0.7963 Intermediate Similarity NPC121816
0.7963 Intermediate Similarity NPC471380
0.7961 Intermediate Similarity NPC309190
0.7959 Intermediate Similarity NPC474035
0.7959 Intermediate Similarity NPC90453
0.7959 Intermediate Similarity NPC81386
0.7957 Intermediate Similarity NPC114979
0.7957 Intermediate Similarity NPC472957
0.7957 Intermediate Similarity NPC472958
0.7957 Intermediate Similarity NPC191476
0.7957 Intermediate Similarity NPC476804
0.7957 Intermediate Similarity NPC165287
0.7944 Intermediate Similarity NPC35069
0.7944 Intermediate Similarity NPC258711
0.7944 Intermediate Similarity NPC189338
0.7944 Intermediate Similarity NPC95290
0.7938 Intermediate Similarity NPC286341

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC213078 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
0.8495 Intermediate Similarity NPD1695 Approved
0.8333 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7979 Intermediate Similarity NPD4249 Approved
0.7944 Intermediate Similarity NPD6053 Discontinued
0.7925 Intermediate Similarity NPD6371 Approved
0.7895 Intermediate Similarity NPD4251 Approved
0.7895 Intermediate Similarity NPD4250 Approved
0.7684 Intermediate Similarity NPD6082 Clinical (unspecified phase)
0.766 Intermediate Similarity NPD5362 Discontinued
0.7527 Intermediate Similarity NPD4822 Approved
0.7527 Intermediate Similarity NPD4819 Approved
0.7527 Intermediate Similarity NPD5790 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD4820 Approved
0.7527 Intermediate Similarity NPD4821 Approved
0.7525 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD5785 Approved
0.7368 Intermediate Similarity NPD6435 Approved
0.732 Intermediate Similarity NPD5363 Approved
0.732 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD4268 Approved
0.7312 Intermediate Similarity NPD4271 Approved
0.73 Intermediate Similarity NPD46 Approved
0.73 Intermediate Similarity NPD6698 Approved
0.7292 Intermediate Similarity NPD7154 Phase 3
0.7263 Intermediate Similarity NPD5369 Approved
0.7188 Intermediate Similarity NPD4270 Approved
0.7188 Intermediate Similarity NPD4269 Approved
0.7158 Intermediate Similarity NPD5368 Approved
0.7113 Intermediate Similarity NPD5331 Approved
0.7113 Intermediate Similarity NPD5332 Approved
0.7087 Intermediate Similarity NPD5282 Discontinued
0.7083 Intermediate Similarity NPD4790 Discontinued
0.7071 Intermediate Similarity NPD5786 Approved
0.7064 Intermediate Similarity NPD6008 Approved
0.6981 Remote Similarity NPD7638 Approved
0.6979 Remote Similarity NPD4252 Approved
0.6961 Remote Similarity NPD7838 Discovery
0.6916 Remote Similarity NPD7640 Approved
0.6916 Remote Similarity NPD7639 Approved
0.6857 Remote Similarity NPD5695 Phase 3
0.6827 Remote Similarity NPD6399 Phase 3
0.6822 Remote Similarity NPD5696 Approved
0.6786 Remote Similarity NPD6686 Approved
0.6771 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6754 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6731 Remote Similarity NPD7983 Approved
0.6729 Remote Similarity NPD6084 Phase 2
0.6729 Remote Similarity NPD6083 Phase 2
0.6721 Remote Similarity NPD7507 Approved
0.6696 Remote Similarity NPD5697 Approved
0.6667 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5778 Approved
0.6667 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4225 Approved
0.6667 Remote Similarity NPD5779 Approved
0.6637 Remote Similarity NPD6881 Approved
0.6637 Remote Similarity NPD7320 Approved
0.6637 Remote Similarity NPD6899 Approved
0.6634 Remote Similarity NPD1694 Approved
0.661 Remote Similarity NPD7115 Discovery
0.6609 Remote Similarity NPD6650 Approved
0.6609 Remote Similarity NPD6649 Approved
0.6607 Remote Similarity NPD5739 Approved
0.6607 Remote Similarity NPD6675 Approved
0.6607 Remote Similarity NPD7128 Approved
0.6607 Remote Similarity NPD6402 Approved
0.6579 Remote Similarity NPD6013 Approved
0.6579 Remote Similarity NPD6372 Approved
0.6579 Remote Similarity NPD6014 Approved
0.6579 Remote Similarity NPD6012 Approved
0.6579 Remote Similarity NPD6373 Approved
0.6571 Remote Similarity NPD5693 Phase 1
0.6571 Remote Similarity NPD5281 Approved
0.6571 Remote Similarity NPD7637 Suspended
0.6571 Remote Similarity NPD5284 Approved
0.656 Remote Similarity NPD7319 Approved
0.6549 Remote Similarity NPD5701 Approved
0.6545 Remote Similarity NPD5344 Discontinued
0.6542 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6529 Remote Similarity NPD8033 Approved
0.6522 Remote Similarity NPD6883 Approved
0.6522 Remote Similarity NPD7102 Approved
0.6522 Remote Similarity NPD7290 Approved
0.6504 Remote Similarity NPD7492 Approved
0.6496 Remote Similarity NPD4632 Approved
0.6491 Remote Similarity NPD6011 Approved
0.6476 Remote Similarity NPD5207 Approved
0.6466 Remote Similarity NPD8130 Phase 1
0.6466 Remote Similarity NPD6847 Approved
0.6466 Remote Similarity NPD6617 Approved
0.6466 Remote Similarity NPD6869 Approved
0.6455 Remote Similarity NPD6648 Approved
0.6452 Remote Similarity NPD6616 Approved
0.6446 Remote Similarity NPD6054 Approved
0.6446 Remote Similarity NPD6319 Approved
0.6442 Remote Similarity NPD6903 Approved
0.6417 Remote Similarity NPD7328 Approved
0.6417 Remote Similarity NPD7327 Approved
0.641 Remote Similarity NPD6882 Approved
0.641 Remote Similarity NPD8297 Approved
0.6408 Remote Similarity NPD7334 Approved
0.6408 Remote Similarity NPD7521 Approved
0.6408 Remote Similarity NPD5330 Approved
0.6408 Remote Similarity NPD7146 Approved
0.6408 Remote Similarity NPD6409 Approved
0.6408 Remote Similarity NPD6684 Approved
0.6404 Remote Similarity NPD6412 Phase 2
0.64 Remote Similarity NPD7078 Approved
0.6393 Remote Similarity NPD6016 Approved
0.6393 Remote Similarity NPD6015 Approved
0.6389 Remote Similarity NPD5210 Approved
0.6389 Remote Similarity NPD4629 Approved
0.6381 Remote Similarity NPD4753 Phase 2
0.6381 Remote Similarity NPD6051 Approved
0.6379 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6373 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6364 Remote Similarity NPD7516 Approved
0.6349 Remote Similarity NPD7736 Approved
0.6341 Remote Similarity NPD6370 Approved
0.6341 Remote Similarity NPD5988 Approved
0.6339 Remote Similarity NPD5211 Phase 2
0.6339 Remote Similarity NPD7632 Discontinued
0.6337 Remote Similarity NPD5209 Approved
0.6333 Remote Similarity NPD6009 Approved
0.6311 Remote Similarity NPD8377 Approved
0.6311 Remote Similarity NPD8294 Approved
0.6311 Remote Similarity NPD6059 Approved
0.6306 Remote Similarity NPD5286 Approved
0.6306 Remote Similarity NPD5285 Approved
0.6306 Remote Similarity NPD4696 Approved
0.6296 Remote Similarity NPD6001 Approved
0.6293 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6286 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6275 Remote Similarity NPD6695 Phase 3
0.6273 Remote Similarity NPD4755 Approved
0.627 Remote Similarity NPD8293 Discontinued
0.6261 Remote Similarity NPD6685 Approved
0.626 Remote Similarity NPD8513 Phase 3
0.626 Remote Similarity NPD8335 Approved
0.626 Remote Similarity NPD8515 Approved
0.626 Remote Similarity NPD7503 Approved
0.626 Remote Similarity NPD8516 Approved
0.626 Remote Similarity NPD8296 Approved
0.626 Remote Similarity NPD8380 Approved
0.626 Remote Similarity NPD8378 Approved
0.626 Remote Similarity NPD5983 Phase 2
0.626 Remote Similarity NPD8517 Approved
0.626 Remote Similarity NPD6291 Clinical (unspecified phase)
0.626 Remote Similarity NPD8379 Approved
0.625 Remote Similarity NPD6007 Clinical (unspecified phase)
0.625 Remote Similarity NPD6274 Approved
0.6228 Remote Similarity NPD5141 Approved
0.6226 Remote Similarity NPD6904 Approved
0.6226 Remote Similarity NPD6673 Approved
0.6226 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6226 Remote Similarity NPD6080 Approved
0.6226 Remote Similarity NPD6101 Approved
0.6214 Remote Similarity NPD3666 Approved
0.6214 Remote Similarity NPD3665 Phase 1
0.6214 Remote Similarity NPD3133 Approved
0.6204 Remote Similarity NPD4202 Approved
0.6196 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6195 Remote Similarity NPD5226 Approved
0.6195 Remote Similarity NPD5225 Approved
0.6195 Remote Similarity NPD5224 Approved
0.6195 Remote Similarity NPD4633 Approved
0.6186 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6182 Remote Similarity NPD7839 Suspended
0.6176 Remote Similarity NPD4221 Approved
0.6176 Remote Similarity NPD4223 Phase 3
0.6168 Remote Similarity NPD5692 Phase 3
0.6161 Remote Similarity NPD4700 Approved
0.616 Remote Similarity NPD7604 Phase 2
0.614 Remote Similarity NPD5175 Approved
0.614 Remote Similarity NPD5174 Approved
0.6132 Remote Similarity NPD5737 Approved
0.6132 Remote Similarity NPD6672 Approved
0.6132 Remote Similarity NPD5208 Approved
0.6121 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6111 Remote Similarity NPD5694 Approved
0.6111 Remote Similarity NPD8035 Phase 2
0.6111 Remote Similarity NPD6411 Approved
0.6111 Remote Similarity NPD6050 Approved
0.6111 Remote Similarity NPD8034 Phase 2
0.6106 Remote Similarity NPD5223 Approved
0.6102 Remote Similarity NPD4634 Approved
0.6098 Remote Similarity NPD7101 Approved
0.6098 Remote Similarity NPD7100 Approved
0.6095 Remote Similarity NPD5690 Phase 2
0.6095 Remote Similarity NPD6098 Approved
0.6083 Remote Similarity NPD8133 Approved
0.6077 Remote Similarity NPD7260 Phase 2
0.6075 Remote Similarity NPD5370 Suspended
0.6066 Remote Similarity NPD6317 Approved
0.6063 Remote Similarity NPD6336 Discontinued
0.6058 Remote Similarity NPD4786 Approved
0.6058 Remote Similarity NPD4197 Approved
0.6038 Remote Similarity NPD7750 Discontinued
0.6038 Remote Similarity NPD7524 Approved
0.6031 Remote Similarity NPD6845 Suspended

Structure

External Identifiers

PubChem CID   267247
ChEMBL   CHEMBL490386
ZINC  

Physicochemical Properties

Molecular Weight:  306.15
ALogP:  0.5188
MLogP:  2.78
XLogP:  1.338
# Rotatable Bonds:  6
Polar Surface Area:  72.83
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  22

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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