Natural Product: NPC86095

Natural Product ID:  NPC86095
Common Name:   Genipin 1-O-Beta-D-Apiofuranosyl(1->6)-Beta-D-Glucopyranoside
IUPAC Name:   methyl (1S,4aS,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Synonyms:  
Molecular Formula:   C22H32O14
Standard InCHIKey:  OOUBSPPBTVIADD-IDPBDCHGSA-N
Standard InCHI:  InChI=1S/C22H32O14/c1-31-18(29)11-5-32-19(13-9(4-23)2-3-10(11)13)36-20-16(27)15(26)14(25)12(35-20)6-33-21-17(28)22(30,7-24)8-34-21/h2,5,10,12-17,19-21,23-28,30H,3-4,6-8H2,1H3/t10-,12-,13-,14-,15+,16-,17+,19+,20+,21-,22-/m1/s1
Canonical SMILES:  OCC1=CC[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@@H]1O[C@H](CO[C@@H]2OC[C@]([C@H]2O)(O)CO)[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]

  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 19332371

  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 NPC86095 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
0.9588 High Similarity NPC310804
0.9588 High Similarity NPC250545
0.9588 High Similarity NPC261117
0.9583 High Similarity NPC306344
0.9583 High Similarity NPC22149
0.9583 High Similarity NPC255677
0.949 High Similarity NPC234304
0.949 High Similarity NPC118761
0.949 High Similarity NPC197541
0.949 High Similarity NPC267869
0.949 High Similarity NPC284929
0.9485 High Similarity NPC298255
0.9485 High Similarity NPC28304
0.9388 High Similarity NPC222062
0.9271 High Similarity NPC241911
0.9192 High Similarity NPC13171
0.9192 High Similarity NPC195510
0.8835 High Similarity NPC254538
0.8835 High Similarity NPC474285
0.8763 High Similarity NPC61201
0.8557 High Similarity NPC6414
0.8557 High Similarity NPC303451
0.8529 High Similarity NPC20673
0.8447 Intermediate Similarity NPC471599
0.8431 Intermediate Similarity NPC244878
0.84 Intermediate Similarity NPC469543
0.8367 Intermediate Similarity NPC117596
0.835 Intermediate Similarity NPC219038
0.8333 Intermediate Similarity NPC151093
0.8283 Intermediate Similarity NPC472125
0.8283 Intermediate Similarity NPC472126
0.8283 Intermediate Similarity NPC472124
0.8247 Intermediate Similarity NPC142583
0.8218 Intermediate Similarity NPC170204
0.8218 Intermediate Similarity NPC101051
0.82 Intermediate Similarity NPC280390
0.8182 Intermediate Similarity NPC231710
0.8182 Intermediate Similarity NPC270908
0.8182 Intermediate Similarity NPC120021
0.8182 Intermediate Similarity NPC307699
0.8182 Intermediate Similarity NPC65665
0.8182 Intermediate Similarity NPC470573
0.8182 Intermediate Similarity NPC216826
0.8173 Intermediate Similarity NPC98859
0.8173 Intermediate Similarity NPC4637
0.8137 Intermediate Similarity NPC306041
0.8081 Intermediate Similarity NPC104129
0.8081 Intermediate Similarity NPC249408
0.8041 Intermediate Similarity NPC470658
0.8021 Intermediate Similarity NPC188717
0.8021 Intermediate Similarity NPC211455
0.8019 Intermediate Similarity NPC37240
0.8019 Intermediate Similarity NPC475928
0.7963 Intermediate Similarity NPC148270
0.7963 Intermediate Similarity NPC197813
0.7963 Intermediate Similarity NPC80338
0.7961 Intermediate Similarity NPC54731
0.7961 Intermediate Similarity NPC161293
0.7938 Intermediate Similarity NPC220167
0.7938 Intermediate Similarity NPC136699
0.7925 Intermediate Similarity NPC106668
0.7925 Intermediate Similarity NPC35185
0.7925 Intermediate Similarity NPC474730
0.7925 Intermediate Similarity NPC4899
0.7925 Intermediate Similarity NPC177013
0.7921 Intermediate Similarity NPC477749
0.7921 Intermediate Similarity NPC9447
0.7905 Intermediate Similarity NPC473146
0.789 Intermediate Similarity NPC110701
0.787 Intermediate Similarity NPC127235
0.787 Intermediate Similarity NPC170432
0.785 Intermediate Similarity NPC27687
0.7843 Intermediate Similarity NPC472195
0.7843 Intermediate Similarity NPC238090
0.7843 Intermediate Similarity NPC320552
0.7843 Intermediate Similarity NPC472196
0.783 Intermediate Similarity NPC3488
0.783 Intermediate Similarity NPC287539
0.7822 Intermediate Similarity NPC118078
0.7822 Intermediate Similarity NPC327253
0.781 Intermediate Similarity NPC473307
0.781 Intermediate Similarity NPC124181
0.781 Intermediate Similarity NPC472015
0.7788 Intermediate Similarity NPC256230
0.7767 Intermediate Similarity NPC159698
0.7767 Intermediate Similarity NPC475927
0.7767 Intermediate Similarity NPC475832
0.7755 Intermediate Similarity NPC266718
0.7755 Intermediate Similarity NPC475035
0.7748 Intermediate Similarity NPC193741
0.7745 Intermediate Similarity NPC472197
0.7739 Intermediate Similarity NPC475309
0.7727 Intermediate Similarity NPC475960
0.7723 Intermediate Similarity NPC477748
0.7714 Intermediate Similarity NPC153559
0.7714 Intermediate Similarity NPC472290
0.77 Intermediate Similarity NPC475037
0.7692 Intermediate Similarity NPC36954
0.7692 Intermediate Similarity NPC473228
0.7692 Intermediate Similarity NPC470829
0.7692 Intermediate Similarity NPC241407
0.7692 Intermediate Similarity NPC291709
0.7677 Intermediate Similarity NPC470124
0.767 Intermediate Similarity NPC320089
0.7647 Intermediate Similarity NPC202886
0.7642 Intermediate Similarity NPC90819
0.7624 Intermediate Similarity NPC137368
0.7615 Intermediate Similarity NPC474917
0.7611 Intermediate Similarity NPC475924
0.7611 Intermediate Similarity NPC475851
0.7596 Intermediate Similarity NPC256368
0.7596 Intermediate Similarity NPC63897
0.7593 Intermediate Similarity NPC304163
0.7593 Intermediate Similarity NPC80144
0.7593 Intermediate Similarity NPC86077
0.7593 Intermediate Similarity NPC201191
0.7586 Intermediate Similarity NPC13710
0.7573 Intermediate Similarity NPC472199
0.7568 Intermediate Similarity NPC177524
0.7568 Intermediate Similarity NPC392
0.7568 Intermediate Similarity NPC219900
0.7565 Intermediate Similarity NPC277583
0.7547 Intermediate Similarity NPC476612
0.7547 Intermediate Similarity NPC476613
0.7545 Intermediate Similarity NPC243998
0.7545 Intermediate Similarity NPC239961
0.7545 Intermediate Similarity NPC223450
0.7544 Intermediate Similarity NPC474410
0.7544 Intermediate Similarity NPC293658
0.7524 Intermediate Similarity NPC6765
0.7524 Intermediate Similarity NPC93869
0.7523 Intermediate Similarity NPC473148
0.7521 Intermediate Similarity NPC474179
0.7521 Intermediate Similarity NPC475834
0.75 Intermediate Similarity NPC67296
0.75 Intermediate Similarity NPC477747
0.75 Intermediate Similarity NPC315836
0.75 Intermediate Similarity NPC475034
0.75 Intermediate Similarity NPC477746
0.75 Intermediate Similarity NPC313668
0.75 Intermediate Similarity NPC476300
0.75 Intermediate Similarity NPC476611
0.75 Intermediate Similarity NPC475912
0.7477 Intermediate Similarity NPC307517
0.7477 Intermediate Similarity NPC198422
0.7477 Intermediate Similarity NPC40182
0.7477 Intermediate Similarity NPC203627
0.7477 Intermediate Similarity NPC249171
0.7477 Intermediate Similarity NPC81483
0.7477 Intermediate Similarity NPC49833
0.7477 Intermediate Similarity NPC61630
0.7477 Intermediate Similarity NPC187268
0.7477 Intermediate Similarity NPC169468
0.7476 Intermediate Similarity NPC474761
0.7476 Intermediate Similarity NPC476004
0.7455 Intermediate Similarity NPC307846
0.7455 Intermediate Similarity NPC305157
0.7453 Intermediate Similarity NPC476315
0.7436 Intermediate Similarity NPC475913
0.7429 Intermediate Similarity NPC294293
0.7429 Intermediate Similarity NPC25701
0.7429 Intermediate Similarity NPC2003
0.7429 Intermediate Similarity NPC71589
0.7429 Intermediate Similarity NPC472198
0.7429 Intermediate Similarity NPC274588
0.7407 Intermediate Similarity NPC469402
0.7404 Intermediate Similarity NPC473150
0.7404 Intermediate Similarity NPC473321
0.7404 Intermediate Similarity NPC184463
0.7404 Intermediate Similarity NPC274274
0.7404 Intermediate Similarity NPC294643
0.7404 Intermediate Similarity NPC30515
0.74 Intermediate Similarity NPC212363
0.7395 Intermediate Similarity NPC170880
0.7391 Intermediate Similarity NPC264153
0.7387 Intermediate Similarity NPC472749
0.7387 Intermediate Similarity NPC469401
0.7387 Intermediate Similarity NPC153095
0.7387 Intermediate Similarity NPC472751
0.7383 Intermediate Similarity NPC304445
0.7383 Intermediate Similarity NPC474194
0.7383 Intermediate Similarity NPC236580
0.7379 Intermediate Similarity NPC93190
0.7379 Intermediate Similarity NPC50464
0.7377 Intermediate Similarity NPC298841
0.7373 Intermediate Similarity NPC219656
0.7373 Intermediate Similarity NPC477071
0.7368 Intermediate Similarity NPC126897
0.7368 Intermediate Similarity NPC297945
0.7364 Intermediate Similarity NPC197736
0.7358 Intermediate Similarity NPC270013
0.7358 Intermediate Similarity NPC14961
0.7355 Intermediate Similarity NPC318135
0.7353 Intermediate Similarity NPC475186
0.7353 Intermediate Similarity NPC118077
0.7347 Intermediate Similarity NPC163362
0.7347 Intermediate Similarity NPC127295
0.7339 Intermediate Similarity NPC473332
0.7339 Intermediate Similarity NPC213634
0.7339 Intermediate Similarity NPC216911

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC86095 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
0.7568 Intermediate Similarity NPD6686 Approved
0.7395 Intermediate Similarity NPD8513 Phase 3
0.7368 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD6698 Approved
0.7308 Intermediate Similarity NPD46 Approved
0.725 Intermediate Similarity NPD8515 Approved
0.725 Intermediate Similarity NPD8516 Approved
0.725 Intermediate Similarity NPD8517 Approved
0.7168 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD7507 Approved
0.7107 Intermediate Similarity NPD7503 Approved
0.7019 Intermediate Similarity NPD4251 Approved
0.7019 Intermediate Similarity NPD4250 Approved
0.7009 Intermediate Similarity NPD6053 Discontinued
0.6984 Remote Similarity NPD7319 Approved
0.6923 Remote Similarity NPD4249 Approved
0.686 Remote Similarity NPD7327 Approved
0.686 Remote Similarity NPD7328 Approved
0.6838 Remote Similarity NPD6371 Approved
0.6829 Remote Similarity NPD8033 Approved
0.6803 Remote Similarity NPD7516 Approved
0.6759 Remote Similarity NPD7983 Approved
0.6748 Remote Similarity NPD8377 Approved
0.6748 Remote Similarity NPD8294 Approved
0.6694 Remote Similarity NPD8380 Approved
0.6694 Remote Similarity NPD8296 Approved
0.6694 Remote Similarity NPD8379 Approved
0.6694 Remote Similarity NPD8335 Approved
0.6694 Remote Similarity NPD8378 Approved
0.6693 Remote Similarity NPD8074 Phase 3
0.6667 Remote Similarity NPD7838 Discovery
0.6635 Remote Similarity NPD7154 Phase 3
0.6635 Remote Similarity NPD6110 Phase 1
0.6587 Remote Similarity NPD7830 Approved
0.6587 Remote Similarity NPD7829 Approved
0.6581 Remote Similarity NPD6412 Phase 2
0.6574 Remote Similarity NPD1695 Approved
0.6571 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6529 Remote Similarity NPD8133 Approved
0.6476 Remote Similarity NPD5362 Discontinued
0.6457 Remote Similarity NPD7642 Approved
0.6435 Remote Similarity NPD5344 Discontinued
0.6404 Remote Similarity NPD4225 Approved
0.6385 Remote Similarity NPD7736 Approved
0.6378 Remote Similarity NPD6370 Approved
0.6372 Remote Similarity NPD7839 Suspended
0.6371 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6371 Remote Similarity NPD7115 Discovery
0.6357 Remote Similarity NPD8451 Approved
0.6355 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6346 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6339 Remote Similarity NPD5282 Discontinued
0.632 Remote Similarity NPD7641 Discontinued
0.6308 Remote Similarity NPD8448 Approved
0.6308 Remote Similarity NPD8293 Discontinued
0.6306 Remote Similarity NPD7637 Suspended
0.6299 Remote Similarity NPD8444 Approved
0.6283 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6279 Remote Similarity NPD8340 Approved
0.6279 Remote Similarity NPD7492 Approved
0.6279 Remote Similarity NPD8342 Approved
0.6279 Remote Similarity NPD8341 Approved
0.6279 Remote Similarity NPD8299 Approved
0.625 Remote Similarity NPD7966 Clinical (unspecified phase)
0.625 Remote Similarity NPD8080 Discontinued
0.625 Remote Similarity NPD5779 Approved
0.625 Remote Similarity NPD5778 Approved
0.6231 Remote Similarity NPD6616 Approved
0.622 Remote Similarity NPD6054 Approved
0.6207 Remote Similarity NPD7640 Approved
0.6207 Remote Similarity NPD7639 Approved
0.6204 Remote Similarity NPD6082 Clinical (unspecified phase)
0.619 Remote Similarity NPD4819 Approved
0.619 Remote Similarity NPD4820 Approved
0.619 Remote Similarity NPD4822 Approved
0.619 Remote Similarity NPD4821 Approved
0.6183 Remote Similarity NPD7078 Approved
0.6172 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6165 Remote Similarity NPD8391 Approved
0.6165 Remote Similarity NPD8392 Approved
0.6165 Remote Similarity NPD8390 Approved
0.6154 Remote Similarity NPD4271 Approved
0.6154 Remote Similarity NPD4268 Approved
0.6121 Remote Similarity NPD7638 Approved
0.6094 Remote Similarity NPD6059 Approved
0.6077 Remote Similarity NPD8328 Phase 3
0.6071 Remote Similarity NPD5785 Approved
0.6068 Remote Similarity NPD6648 Approved
0.6066 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6048 Remote Similarity NPD6882 Approved
0.6047 Remote Similarity NPD6015 Approved
0.6047 Remote Similarity NPD6016 Approved
0.6019 Remote Similarity NPD5332 Approved
0.6019 Remote Similarity NPD5331 Approved
0.6015 Remote Similarity NPD8336 Approved
0.6015 Remote Similarity NPD8337 Approved
0.6 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6 Remote Similarity NPD5988 Approved
0.5984 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5984 Remote Similarity NPD6009 Approved
0.5981 Remote Similarity NPD4790 Discontinued
0.5969 Remote Similarity NPD6319 Approved
0.5968 Remote Similarity NPD2204 Approved
0.5946 Remote Similarity NPD7524 Approved
0.5935 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5926 Remote Similarity NPD6435 Approved
0.592 Remote Similarity NPD8297 Approved
0.5917 Remote Similarity NPD1407 Approved
0.5909 Remote Similarity NPD5363 Approved
0.5888 Remote Similarity NPD4252 Approved
0.5882 Remote Similarity NPD7260 Phase 2
0.5873 Remote Similarity NPD4632 Approved
0.5856 Remote Similarity NPD5786 Approved
0.5841 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5841 Remote Similarity NPD6101 Approved
0.5839 Remote Similarity NPD6845 Suspended
0.5839 Remote Similarity NPD8338 Approved
0.5818 Remote Similarity NPD7338 Clinical (unspecified phase)
0.58 Remote Similarity NPD4247 Clinical (unspecified phase)
0.578 Remote Similarity NPD4270 Approved
0.578 Remote Similarity NPD4269 Approved
0.576 Remote Similarity NPD6421 Discontinued
0.576 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5746 Remote Similarity NPD8273 Phase 1
0.5741 Remote Similarity NPD5368 Approved
0.5741 Remote Similarity NPD7332 Phase 2
0.5739 Remote Similarity NPD6411 Approved
0.5727 Remote Similarity NPD6695 Phase 3
0.5726 Remote Similarity NPD6899 Approved
0.5726 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5726 Remote Similarity NPD6881 Approved
0.5726 Remote Similarity NPD7320 Approved
0.5714 Remote Similarity NPD6649 Approved
0.5714 Remote Similarity NPD6067 Discontinued
0.5714 Remote Similarity NPD6650 Approved
0.5702 Remote Similarity NPD7632 Discontinued
0.5691 Remote Similarity NPD5739 Approved
0.5691 Remote Similarity NPD6402 Approved
0.5691 Remote Similarity NPD6008 Approved
0.5691 Remote Similarity NPD6675 Approved
0.5691 Remote Similarity NPD7128 Approved
0.569 Remote Similarity NPD6399 Phase 3
0.5688 Remote Similarity NPD5369 Approved
0.5682 Remote Similarity NPD8266 Approved
0.5682 Remote Similarity NPD8267 Approved
0.5682 Remote Similarity NPD8269 Approved
0.5682 Remote Similarity NPD8268 Approved
0.568 Remote Similarity NPD6372 Approved
0.568 Remote Similarity NPD6373 Approved
0.5678 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5671 Remote Similarity NPD7685 Pre-registration
0.5662 Remote Similarity NPD6033 Approved
0.5645 Remote Similarity NPD5697 Approved
0.5636 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5636 Remote Similarity NPD5209 Approved
0.5635 Remote Similarity NPD7102 Approved
0.5635 Remote Similarity NPD6883 Approved
0.5635 Remote Similarity NPD7290 Approved
0.563 Remote Similarity NPD6084 Phase 2
0.563 Remote Similarity NPD6083 Phase 2
0.5615 Remote Similarity NPD7500 Approved
0.561 Remote Similarity NPD8170 Clinical (unspecified phase)
0.5603 Remote Similarity NPD8387 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   71552450
ChEMBL   CHEMBL2316918
ZINC  

Physicochemical Properties

Molecular Weight:  520.18
ALogP:  -4.3299
MLogP:  2.34
XLogP:  -3.191
# Rotatable Bonds:  17
Polar Surface Area:  214.06
# H-Bond Aceptor:  14
# H-Bond Donor:  7
# Rings:  4
# Heavy Atoms:  36

Download Data

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