Natural Product: NPC222062

Natural Product ID:  NPC222062
Common Name:   Genameside D
IUPAC Name:   methyl (1S,4aS,7aS)-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Synonyms:   Genameside D
Molecular Formula:   C23H34O15
Standard InCHIKey:  BNXFBCBJALNHOV-AUOPOVQUSA-N
Standard InCHI:  InChI=1S/C23H34O15/c1-33-20(32)10-7-35-21(38-23-19(31)17(29)15(27)12(5-25)37-23)13-8(2-3-9(10)13)6-34-22-18(30)16(28)14(26)11(4-24)36-22/h2,7,9,11-19,21-31H,3-6H2,1H3/t9-,11-,12-,13-,14-,15-,16+,17+,18-,19-,21+,22-,23+/m1/s1
Canonical SMILES:  OC[C@H]1O[C@@H](OCC2=CC[C@H]3[C@@H]2[C@@H](OC=C3C(=O)OC)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)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
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota fruits PMID[23305920]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota TM-MC*
NPO17824 Genipa americana Species Rubiaceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell Line RAW264.7 Mus musculus IC50 > 100000 nM 23305920

  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 NPC222062 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
0.9895 High Similarity NPC284929
0.9895 High Similarity NPC118761
0.9895 High Similarity NPC197541
0.9895 High Similarity NPC234304
0.9895 High Similarity NPC267869
0.9579 High Similarity NPC255677
0.9579 High Similarity NPC22149
0.9579 High Similarity NPC306344
0.9479 High Similarity NPC298255
0.9479 High Similarity NPC28304
0.9388 High Similarity NPC86095
0.9381 High Similarity NPC261117
0.9381 High Similarity NPC310804
0.9263 High Similarity NPC241911
0.9184 High Similarity NPC250545
0.899 High Similarity NPC195510
0.899 High Similarity NPC13171
0.8958 High Similarity NPC469543
0.8947 High Similarity NPC61201
0.8842 High Similarity NPC472124
0.8842 High Similarity NPC472125
0.8842 High Similarity NPC472126
0.8737 High Similarity NPC270908
0.8737 High Similarity NPC307699
0.8737 High Similarity NPC303451
0.8737 High Similarity NPC6414
0.8737 High Similarity NPC470573
0.8737 High Similarity NPC216826
0.8737 High Similarity NPC65665
0.8737 High Similarity NPC120021
0.8737 High Similarity NPC231710
0.8571 High Similarity NPC170204
0.8542 High Similarity NPC117596
0.8462 Intermediate Similarity NPC254538
0.8462 Intermediate Similarity NPC474285
0.8431 Intermediate Similarity NPC471599
0.8416 Intermediate Similarity NPC244878
0.8384 Intermediate Similarity NPC101051
0.8367 Intermediate Similarity NPC280390
0.8333 Intermediate Similarity NPC20673
0.8333 Intermediate Similarity NPC219038
0.8317 Intermediate Similarity NPC151093
0.8229 Intermediate Similarity NPC142583
0.8173 Intermediate Similarity NPC475928
0.8155 Intermediate Similarity NPC98859
0.8155 Intermediate Similarity NPC4637
0.8119 Intermediate Similarity NPC306041
0.8077 Intermediate Similarity NPC474730
0.8077 Intermediate Similarity NPC35185
0.8077 Intermediate Similarity NPC106668
0.8077 Intermediate Similarity NPC4899
0.8077 Intermediate Similarity NPC177013
0.8019 Intermediate Similarity NPC170432
0.8 Intermediate Similarity NPC27687
0.8 Intermediate Similarity NPC211455
0.8 Intermediate Similarity NPC188717
0.8 Intermediate Similarity NPC320552
0.8 Intermediate Similarity NPC37240
0.798 Intermediate Similarity NPC327253
0.7961 Intermediate Similarity NPC40182
0.7961 Intermediate Similarity NPC472015
0.7961 Intermediate Similarity NPC198422
0.7944 Intermediate Similarity NPC148270
0.7944 Intermediate Similarity NPC197813
0.7944 Intermediate Similarity NPC80338
0.7941 Intermediate Similarity NPC161293
0.7941 Intermediate Similarity NPC54731
0.7921 Intermediate Similarity NPC294293
0.7917 Intermediate Similarity NPC136699
0.7917 Intermediate Similarity NPC220167
0.7917 Intermediate Similarity NPC266718
0.79 Intermediate Similarity NPC9447
0.79 Intermediate Similarity NPC477749
0.787 Intermediate Similarity NPC177524
0.787 Intermediate Similarity NPC392
0.787 Intermediate Similarity NPC219900
0.7864 Intermediate Similarity NPC472290
0.7835 Intermediate Similarity NPC470124
0.783 Intermediate Similarity NPC197736
0.7822 Intermediate Similarity NPC472196
0.7822 Intermediate Similarity NPC472195
0.7822 Intermediate Similarity NPC238090
0.781 Intermediate Similarity NPC3488
0.781 Intermediate Similarity NPC287539
0.7788 Intermediate Similarity NPC473307
0.7788 Intermediate Similarity NPC124181
0.7745 Intermediate Similarity NPC159698
0.7745 Intermediate Similarity NPC63897
0.7736 Intermediate Similarity NPC201191
0.7727 Intermediate Similarity NPC193741
0.7723 Intermediate Similarity NPC472197
0.7719 Intermediate Similarity NPC13710
0.7714 Intermediate Similarity NPC473146
0.7706 Intermediate Similarity NPC473807
0.7706 Intermediate Similarity NPC110701
0.77 Intermediate Similarity NPC104129
0.77 Intermediate Similarity NPC477748
0.77 Intermediate Similarity NPC249408
0.7692 Intermediate Similarity NPC153559
0.7685 Intermediate Similarity NPC127235
0.7684 Intermediate Similarity NPC127295
0.7684 Intermediate Similarity NPC163362
0.7672 Intermediate Similarity NPC470829
0.7672 Intermediate Similarity NPC473228
0.767 Intermediate Similarity NPC291709
0.767 Intermediate Similarity NPC241407
0.7653 Intermediate Similarity NPC470658
0.7647 Intermediate Similarity NPC320089
0.7642 Intermediate Similarity NPC476611
0.7624 Intermediate Similarity NPC202886
0.7619 Intermediate Similarity NPC90819
0.76 Intermediate Similarity NPC137368
0.7596 Intermediate Similarity NPC256230
0.7596 Intermediate Similarity NPC143446
0.7589 Intermediate Similarity NPC475924
0.7589 Intermediate Similarity NPC475851
0.7579 Intermediate Similarity NPC323472
0.7573 Intermediate Similarity NPC71589
0.7573 Intermediate Similarity NPC256368
0.7573 Intermediate Similarity NPC2003
0.7573 Intermediate Similarity NPC25701
0.7568 Intermediate Similarity NPC83005
0.7565 Intermediate Similarity NPC475309
0.7551 Intermediate Similarity NPC475035
0.7549 Intermediate Similarity NPC472199
0.7525 Intermediate Similarity NPC285588
0.7524 Intermediate Similarity NPC476613
0.7524 Intermediate Similarity NPC476612
0.7523 Intermediate Similarity NPC41681
0.7523 Intermediate Similarity NPC476738
0.7523 Intermediate Similarity NPC476740
0.7521 Intermediate Similarity NPC476204
0.7521 Intermediate Similarity NPC170084
0.75 Intermediate Similarity NPC475186
0.75 Intermediate Similarity NPC118077
0.75 Intermediate Similarity NPC6765
0.75 Intermediate Similarity NPC93869
0.75 Intermediate Similarity NPC475037
0.75 Intermediate Similarity NPC309398
0.7479 Intermediate Similarity NPC318135
0.7478 Intermediate Similarity NPC474483
0.7477 Intermediate Similarity NPC471637
0.7477 Intermediate Similarity NPC154132
0.7477 Intermediate Similarity NPC475655
0.7477 Intermediate Similarity NPC57586
0.7477 Intermediate Similarity NPC118225
0.7477 Intermediate Similarity NPC313668
0.7477 Intermediate Similarity NPC475157
0.7477 Intermediate Similarity NPC315836
0.7477 Intermediate Similarity NPC2313
0.7475 Intermediate Similarity NPC477746
0.7475 Intermediate Similarity NPC477747
0.7459 Intermediate Similarity NPC213634
0.7456 Intermediate Similarity NPC472274
0.7451 Intermediate Similarity NPC118078
0.7438 Intermediate Similarity NPC245094
0.7436 Intermediate Similarity NPC470312
0.7431 Intermediate Similarity NPC469869
0.7426 Intermediate Similarity NPC248312
0.7407 Intermediate Similarity NPC304163
0.7404 Intermediate Similarity NPC238264
0.7404 Intermediate Similarity NPC477345
0.7404 Intermediate Similarity NPC475832
0.7404 Intermediate Similarity NPC475927
0.7404 Intermediate Similarity NPC274588
0.7404 Intermediate Similarity NPC472198
0.7404 Intermediate Similarity NPC477348
0.7398 Intermediate Similarity NPC155529
0.7391 Intermediate Similarity NPC207637
0.7387 Intermediate Similarity NPC475960
0.7387 Intermediate Similarity NPC193765
0.7379 Intermediate Similarity NPC470373
0.7379 Intermediate Similarity NPC110072
0.7379 Intermediate Similarity NPC470379
0.7373 Intermediate Similarity NPC170880
0.7373 Intermediate Similarity NPC202051
0.7368 Intermediate Similarity NPC293658
0.7368 Intermediate Similarity NPC75167
0.7368 Intermediate Similarity NPC264153
0.7368 Intermediate Similarity NPC311592
0.7368 Intermediate Similarity NPC474410
0.736 Intermediate Similarity NPC158350
0.7358 Intermediate Similarity NPC278506
0.7353 Intermediate Similarity NPC50464
0.735 Intermediate Similarity NPC122971
0.735 Intermediate Similarity NPC219656
0.7347 Intermediate Similarity NPC251026
0.7345 Intermediate Similarity NPC126897
0.7345 Intermediate Similarity NPC297945
0.7339 Intermediate Similarity NPC473816
0.7339 Intermediate Similarity NPC473148
0.7339 Intermediate Similarity NPC475367
0.7339 Intermediate Similarity NPC474581
0.7333 Intermediate Similarity NPC36954
0.7327 Intermediate Similarity NPC74139
0.7321 Intermediate Similarity NPC133625
0.7315 Intermediate Similarity NPC198992
0.7308 Intermediate Similarity NPC476300
0.7304 Intermediate Similarity NPC165439
0.7304 Intermediate Similarity NPC181145

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC222062 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
0.787 Intermediate Similarity NPD6686 Approved
0.7451 Intermediate Similarity NPD6698 Approved
0.7451 Intermediate Similarity NPD46 Approved
0.7373 Intermediate Similarity NPD8513 Phase 3
0.7345 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7227 Intermediate Similarity NPD8516 Approved
0.7227 Intermediate Similarity NPD8515 Approved
0.7227 Intermediate Similarity NPD7503 Approved
0.7227 Intermediate Similarity NPD8517 Approved
0.7131 Intermediate Similarity NPD7507 Approved
0.6983 Remote Similarity NPD6053 Discontinued
0.696 Remote Similarity NPD7319 Approved
0.6942 Remote Similarity NPD8033 Approved
0.686 Remote Similarity NPD8294 Approved
0.686 Remote Similarity NPD8377 Approved
0.6842 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6842 Remote Similarity NPD6412 Phase 2
0.6833 Remote Similarity NPD7327 Approved
0.6833 Remote Similarity NPD7328 Approved
0.6829 Remote Similarity NPD7830 Approved
0.6829 Remote Similarity NPD7829 Approved
0.6803 Remote Similarity NPD8296 Approved
0.6803 Remote Similarity NPD8335 Approved
0.6803 Remote Similarity NPD8379 Approved
0.6803 Remote Similarity NPD8378 Approved
0.6803 Remote Similarity NPD8380 Approved
0.6792 Remote Similarity NPD7838 Discovery
0.678 Remote Similarity NPD8133 Approved
0.6777 Remote Similarity NPD7516 Approved
0.6729 Remote Similarity NPD7983 Approved
0.6667 Remote Similarity NPD4250 Approved
0.6667 Remote Similarity NPD8074 Phase 3
0.6667 Remote Similarity NPD4251 Approved
0.6667 Remote Similarity NPD6371 Approved
0.6602 Remote Similarity NPD6110 Phase 1
0.6602 Remote Similarity NPD7154 Phase 3
0.6571 Remote Similarity NPD4249 Approved
0.6538 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6475 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6457 Remote Similarity NPD8451 Approved
0.6429 Remote Similarity NPD8328 Phase 3
0.6429 Remote Similarity NPD7642 Approved
0.6423 Remote Similarity NPD7641 Discontinued
0.6406 Remote Similarity NPD8448 Approved
0.64 Remote Similarity NPD8444 Approved
0.6385 Remote Similarity NPD8390 Approved
0.6385 Remote Similarity NPD8391 Approved
0.6385 Remote Similarity NPD8392 Approved
0.6372 Remote Similarity NPD7638 Approved
0.6349 Remote Similarity NPD8080 Discontinued
0.6341 Remote Similarity NPD7115 Discovery
0.6341 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6339 Remote Similarity NPD7839 Suspended
0.6316 Remote Similarity NPD7640 Approved
0.6316 Remote Similarity NPD7639 Approved
0.6311 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6303 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6286 Remote Similarity NPD5362 Discontinued
0.6273 Remote Similarity NPD7637 Suspended
0.627 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6261 Remote Similarity NPD5344 Discontinued
0.625 Remote Similarity NPD8299 Approved
0.625 Remote Similarity NPD8342 Approved
0.625 Remote Similarity NPD8341 Approved
0.625 Remote Similarity NPD8340 Approved
0.6239 Remote Similarity NPD1695 Approved
0.6231 Remote Similarity NPD8337 Approved
0.6231 Remote Similarity NPD8336 Approved
0.6231 Remote Similarity NPD7736 Approved
0.6228 Remote Similarity NPD4225 Approved
0.622 Remote Similarity NPD6370 Approved
0.6216 Remote Similarity NPD5778 Approved
0.6216 Remote Similarity NPD5779 Approved
0.6168 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6168 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6154 Remote Similarity NPD8293 Discontinued
0.6148 Remote Similarity NPD6882 Approved
0.6124 Remote Similarity NPD7492 Approved
0.6117 Remote Similarity NPD4268 Approved
0.6117 Remote Similarity NPD4271 Approved
0.6106 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6103 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6091 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6091 Remote Similarity NPD6101 Approved
0.609 Remote Similarity NPD7260 Phase 2
0.608 Remote Similarity NPD6009 Approved
0.6077 Remote Similarity NPD6616 Approved
0.6063 Remote Similarity NPD6054 Approved
0.6063 Remote Similarity NPD6319 Approved
0.6038 Remote Similarity NPD6435 Approved
0.6036 Remote Similarity NPD5785 Approved
0.6033 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6031 Remote Similarity NPD7078 Approved
0.6018 Remote Similarity NPD5282 Discontinued
0.6016 Remote Similarity NPD8297 Approved
0.6 Remote Similarity NPD4821 Approved
0.6 Remote Similarity NPD4822 Approved
0.6 Remote Similarity NPD4819 Approved
0.6 Remote Similarity NPD4820 Approved
0.5982 Remote Similarity NPD6411 Approved
0.5968 Remote Similarity NPD4632 Approved
0.5962 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5938 Remote Similarity NPD6059 Approved
0.5929 Remote Similarity NPD6399 Phase 3
0.5926 Remote Similarity NPD8338 Approved
0.5905 Remote Similarity NPD7329 Approved
0.5897 Remote Similarity NPD6648 Approved
0.5891 Remote Similarity NPD6016 Approved
0.5891 Remote Similarity NPD6015 Approved
0.5882 Remote Similarity NPD1407 Approved
0.5872 Remote Similarity NPD5363 Approved
0.5854 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5849 Remote Similarity NPD4252 Approved
0.5849 Remote Similarity NPD5368 Approved
0.5846 Remote Similarity NPD5988 Approved
0.5833 Remote Similarity NPD5332 Approved
0.5833 Remote Similarity NPD5331 Approved
0.582 Remote Similarity NPD6899 Approved
0.582 Remote Similarity NPD5345 Clinical (unspecified phase)
0.582 Remote Similarity NPD6881 Approved
0.5818 Remote Similarity NPD5786 Approved
0.5809 Remote Similarity NPD6845 Suspended
0.5806 Remote Similarity NPD6649 Approved
0.5806 Remote Similarity NPD6650 Approved
0.5798 Remote Similarity NPD7632 Discontinued
0.5797 Remote Similarity NPD8387 Clinical (unspecified phase)
0.5794 Remote Similarity NPD4790 Discontinued
0.5785 Remote Similarity NPD6402 Approved
0.5785 Remote Similarity NPD6675 Approved
0.5785 Remote Similarity NPD7128 Approved
0.5785 Remote Similarity NPD5739 Approved
0.5772 Remote Similarity NPD6373 Approved
0.5772 Remote Similarity NPD6372 Approved
0.5769 Remote Similarity NPD8267 Approved
0.5769 Remote Similarity NPD8266 Approved
0.5769 Remote Similarity NPD8269 Approved
0.5769 Remote Similarity NPD8268 Approved
0.5766 Remote Similarity NPD7524 Approved
0.5758 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5741 Remote Similarity NPD4270 Approved
0.5741 Remote Similarity NPD5209 Approved
0.5741 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5741 Remote Similarity NPD4269 Approved
0.5738 Remote Similarity NPD5697 Approved
0.5726 Remote Similarity NPD7102 Approved
0.5726 Remote Similarity NPD7290 Approved
0.5726 Remote Similarity NPD6083 Phase 2
0.5726 Remote Similarity NPD6883 Approved
0.5726 Remote Similarity NPD6084 Phase 2
0.5726 Remote Similarity NPD6421 Discontinued
0.5725 Remote Similarity NPD8415 Approved
0.5702 Remote Similarity NPD8170 Clinical (unspecified phase)
0.5691 Remote Similarity NPD7320 Approved
0.5682 Remote Similarity NPD7604 Phase 2
0.5682 Remote Similarity NPD6067 Discontinued
0.568 Remote Similarity NPD2204 Approved
0.568 Remote Similarity NPD8130 Phase 1
0.568 Remote Similarity NPD6869 Approved
0.568 Remote Similarity NPD6617 Approved
0.568 Remote Similarity NPD6847 Approved
0.5676 Remote Similarity NPD8389 Clinical (unspecified phase)
0.5649 Remote Similarity NPD5983 Phase 2
0.5648 Remote Similarity NPD5369 Approved
0.5645 Remote Similarity NPD6014 Approved
0.5645 Remote Similarity NPD6012 Approved
0.5645 Remote Similarity NPD6013 Approved
0.5644 Remote Similarity NPD7685 Pre-registration
0.5641 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5636 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5631 Remote Similarity NPD3181 Approved
0.5625 Remote Similarity NPD7266 Discontinued
0.5616 Remote Similarity NPD7625 Phase 1
0.561 Remote Similarity NPD5701 Approved
0.561 Remote Similarity NPD5954 Clinical (unspecified phase)
0.56 Remote Similarity NPD897 Approved
0.56 Remote Similarity NPD896 Approved
0.56 Remote Similarity NPD898 Approved

Structure

External Identifiers

PubChem CID   11570273
ChEMBL   CHEMBL2311861
ZINC  

Physicochemical Properties

Molecular Weight:  550.19
ALogP:  -4.6681
MLogP:  2.34
XLogP:  -2.962
# Rotatable Bonds:  18
Polar Surface Area:  234.29
# H-Bond Aceptor:  15
# H-Bond Donor:  8
# Rings:  4
# Heavy Atoms:  38

Download Data

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