Natural Product: NPC298255

Natural Product ID:  NPC298255
Common Name:   6Beta-Hydroxygeniposide
IUPAC Name:   methyl (1S,4aS,5R,7aS)-5-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Synonyms:   6Beta-Hydroxygeniposide
Molecular Formula:   C17H24O11
Standard InCHIKey:  WSGPLSDARZNMCW-LPGRTNKPSA-N
Standard InCHI:  InChI=1S/C17H24O11/c1-25-15(24)7-5-26-16(10-6(3-18)2-8(20)11(7)10)28-17-14(23)13(22)12(21)9(4-19)27-17/h2,5,8-14,16-23H,3-4H2,1H3/t8-,9-,10-,11+,12-,13+,14-,16+,17+/m1/s1
Canonical SMILES:  OCC1=C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)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
NPO2562 Thymus membranaceus Species Lamiaceae Eukaryota UNPD*
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota fruits PMID[23305920]
NPO8136 Pterospermum heyneanum Species Malvaceae Eukaryota UNPD*
NPO6969 Triphyophyllum peltatum Species Dioncophyllaceae Eukaryota UNPD*
NPO8954 Torilis scabra Species Apiaceae Eukaryota UNPD*
NPO14651 Anthocercis frondosa Species Solanaceae Eukaryota UNPD*
NPO130 Galeopsis bifida Species Lamiaceae Eukaryota UNPD*
NPO8590 Phlomoides tuberosa Species Lamiaceae Eukaryota UNPD*
NPO20949 Paederiae scandentis herba NA NA NA TCMSP*
NPO17872 Hedyotis diffusae herba Species Rubiaceae Eukaryota TCMSP*
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota TM-MC*
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota TM-MC*

  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 NPC298255 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 NPC28304
0.9892 High Similarity NPC306344
0.9892 High Similarity NPC255677
0.9892 High Similarity NPC22149
0.9684 High Similarity NPC310804
0.9684 High Similarity NPC250545
0.9684 High Similarity NPC261117
0.9583 High Similarity NPC234304
0.9583 High Similarity NPC197541
0.9583 High Similarity NPC118761
0.9583 High Similarity NPC267869
0.9583 High Similarity NPC284929
0.957 High Similarity NPC241911
0.9485 High Similarity NPC86095
0.9479 High Similarity NPC222062
0.9278 High Similarity NPC195510
0.9278 High Similarity NPC13171
0.9043 High Similarity NPC61201
0.883 High Similarity NPC303451
0.883 High Similarity NPC6414
0.8725 High Similarity NPC474285
0.8725 High Similarity NPC254538
0.871 High Similarity NPC142583
0.8632 High Similarity NPC117596
0.8542 High Similarity NPC472126
0.8542 High Similarity NPC472124
0.8542 High Similarity NPC472125
0.8469 Intermediate Similarity NPC469543
0.8469 Intermediate Similarity NPC170204
0.8438 Intermediate Similarity NPC120021
0.8438 Intermediate Similarity NPC270908
0.8438 Intermediate Similarity NPC470573
0.8438 Intermediate Similarity NPC65665
0.8438 Intermediate Similarity NPC307699
0.8438 Intermediate Similarity NPC216826
0.8438 Intermediate Similarity NPC231710
0.8431 Intermediate Similarity NPC475928
0.8416 Intermediate Similarity NPC20673
0.8384 Intermediate Similarity NPC306041
0.8333 Intermediate Similarity NPC471599
0.8333 Intermediate Similarity NPC106668
0.8317 Intermediate Similarity NPC244878
0.8283 Intermediate Similarity NPC101051
0.828 Intermediate Similarity NPC211455
0.828 Intermediate Similarity NPC188717
0.8269 Intermediate Similarity NPC170432
0.8252 Intermediate Similarity NPC27687
0.8235 Intermediate Similarity NPC219038
0.8218 Intermediate Similarity NPC151093
0.82 Intermediate Similarity NPC161293
0.8191 Intermediate Similarity NPC136699
0.8191 Intermediate Similarity NPC220167
0.819 Intermediate Similarity NPC148270
0.819 Intermediate Similarity NPC197813
0.819 Intermediate Similarity NPC80338
0.8163 Intermediate Similarity NPC9447
0.8155 Intermediate Similarity NPC177013
0.8155 Intermediate Similarity NPC4899
0.8155 Intermediate Similarity NPC474730
0.8155 Intermediate Similarity NPC35185
0.8113 Intermediate Similarity NPC110701
0.8095 Intermediate Similarity NPC127235
0.8081 Intermediate Similarity NPC280390
0.8077 Intermediate Similarity NPC37240
0.8058 Intermediate Similarity NPC98859
0.8058 Intermediate Similarity NPC287539
0.8058 Intermediate Similarity NPC4637
0.8058 Intermediate Similarity NPC3488
0.8041 Intermediate Similarity NPC137368
0.8039 Intermediate Similarity NPC472015
0.802 Intermediate Similarity NPC54731
0.798 Intermediate Similarity NPC472197
0.7963 Intermediate Similarity NPC193741
0.7961 Intermediate Similarity NPC473146
0.7941 Intermediate Similarity NPC472290
0.7917 Intermediate Similarity NPC470124
0.79 Intermediate Similarity NPC472195
0.79 Intermediate Similarity NPC472196
0.79 Intermediate Similarity NPC238090
0.79 Intermediate Similarity NPC320552
0.7879 Intermediate Similarity NPC327253
0.7864 Intermediate Similarity NPC473307
0.7822 Intermediate Similarity NPC63897
0.7822 Intermediate Similarity NPC159698
0.7818 Intermediate Similarity NPC475924
0.7818 Intermediate Similarity NPC475851
0.7812 Intermediate Similarity NPC266718
0.7812 Intermediate Similarity NPC475035
0.78 Intermediate Similarity NPC477749
0.7767 Intermediate Similarity NPC153559
0.7755 Intermediate Similarity NPC475037
0.7745 Intermediate Similarity NPC241407
0.7745 Intermediate Similarity NPC291709
0.7739 Intermediate Similarity NPC470829
0.7739 Intermediate Similarity NPC473228
0.7732 Intermediate Similarity NPC470658
0.7692 Intermediate Similarity NPC124181
0.7692 Intermediate Similarity NPC169468
0.7692 Intermediate Similarity NPC307517
0.7692 Intermediate Similarity NPC61630
0.7692 Intermediate Similarity NPC81483
0.7647 Intermediate Similarity NPC475832
0.7647 Intermediate Similarity NPC475927
0.7647 Intermediate Similarity NPC71589
0.7647 Intermediate Similarity NPC25701
0.7647 Intermediate Similarity NPC2003
0.7642 Intermediate Similarity NPC304163
0.7642 Intermediate Similarity NPC201191
0.7642 Intermediate Similarity NPC80144
0.7624 Intermediate Similarity NPC472199
0.7624 Intermediate Similarity NPC473321
0.7615 Intermediate Similarity NPC475960
0.7615 Intermediate Similarity NPC392
0.7615 Intermediate Similarity NPC177524
0.7615 Intermediate Similarity NPC219900
0.76 Intermediate Similarity NPC104129
0.76 Intermediate Similarity NPC477748
0.76 Intermediate Similarity NPC249408
0.7596 Intermediate Similarity NPC474194
0.7573 Intermediate Similarity NPC36954
0.7551 Intermediate Similarity NPC475034
0.7551 Intermediate Similarity NPC21469
0.7549 Intermediate Similarity NPC320089
0.7549 Intermediate Similarity NPC475912
0.7547 Intermediate Similarity NPC67296
0.7525 Intermediate Similarity NPC202886
0.7525 Intermediate Similarity NPC474232
0.7525 Intermediate Similarity NPC473619
0.7524 Intermediate Similarity NPC90819
0.7524 Intermediate Similarity NPC198422
0.7524 Intermediate Similarity NPC37866
0.7524 Intermediate Similarity NPC49833
0.7524 Intermediate Similarity NPC40182
0.7524 Intermediate Similarity NPC249171
0.75 Intermediate Similarity NPC474917
0.75 Intermediate Similarity NPC473715
0.75 Intermediate Similarity NPC256230
0.75 Intermediate Similarity NPC470137
0.7478 Intermediate Similarity NPC475309
0.7478 Intermediate Similarity NPC13710
0.7477 Intermediate Similarity NPC86077
0.7476 Intermediate Similarity NPC256368
0.7476 Intermediate Similarity NPC472198
0.7476 Intermediate Similarity NPC294293
0.7456 Intermediate Similarity NPC277583
0.7453 Intermediate Similarity NPC469402
0.7451 Intermediate Similarity NPC294643
0.7451 Intermediate Similarity NPC470379
0.7451 Intermediate Similarity NPC473150
0.7451 Intermediate Similarity NPC470373
0.7451 Intermediate Similarity NPC274274
0.7449 Intermediate Similarity NPC212363
0.7434 Intermediate Similarity NPC264153
0.7431 Intermediate Similarity NPC41681
0.7431 Intermediate Similarity NPC243998
0.7431 Intermediate Similarity NPC153095
0.7431 Intermediate Similarity NPC223450
0.7429 Intermediate Similarity NPC236580
0.7429 Intermediate Similarity NPC476612
0.7429 Intermediate Similarity NPC304445
0.7429 Intermediate Similarity NPC476613
0.7426 Intermediate Similarity NPC93190
0.7426 Intermediate Similarity NPC50464
0.7407 Intermediate Similarity NPC473148
0.7407 Intermediate Similarity NPC197736
0.7407 Intermediate Similarity NPC151516
0.7404 Intermediate Similarity NPC6765
0.7404 Intermediate Similarity NPC471142
0.7404 Intermediate Similarity NPC270013
0.7404 Intermediate Similarity NPC93869
0.7404 Intermediate Similarity NPC14961
0.74 Intermediate Similarity NPC475186
0.74 Intermediate Similarity NPC74139
0.74 Intermediate Similarity NPC118077
0.7396 Intermediate Similarity NPC127295
0.7396 Intermediate Similarity NPC163362
0.7395 Intermediate Similarity NPC318135
0.7383 Intermediate Similarity NPC476611
0.7383 Intermediate Similarity NPC473332
0.7383 Intermediate Similarity NPC154127
0.7383 Intermediate Similarity NPC198992
0.7379 Intermediate Similarity NPC295204
0.7379 Intermediate Similarity NPC273579
0.7379 Intermediate Similarity NPC476300
0.7379 Intermediate Similarity NPC288240
0.7379 Intermediate Similarity NPC162205
0.7377 Intermediate Similarity NPC213634
0.7374 Intermediate Similarity NPC477746
0.7374 Intermediate Similarity NPC477747
0.7368 Intermediate Similarity NPC472274
0.7358 Intermediate Similarity NPC187268
0.7358 Intermediate Similarity NPC203627
0.7353 Intermediate Similarity NPC118078
0.735 Intermediate Similarity NPC48692
0.7347 Intermediate Similarity NPC142111
0.7347 Intermediate Similarity NPC473315
0.7339 Intermediate Similarity NPC305157
0.7339 Intermediate Similarity NPC307846
0.7333 Intermediate Similarity NPC474297
0.7333 Intermediate Similarity NPC476315

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC298255 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
0.7615 Intermediate Similarity NPD6686 Approved
0.7358 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD46 Approved
0.7353 Intermediate Similarity NPD6698 Approved
0.7288 Intermediate Similarity NPD8513 Phase 3
0.7257 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD8515 Approved
0.7143 Intermediate Similarity NPD8516 Approved
0.7143 Intermediate Similarity NPD8517 Approved
0.7 Intermediate Similarity NPD7503 Approved
0.6911 Remote Similarity NPD7507 Approved
0.6903 Remote Similarity NPD7899 Clinical (unspecified phase)
0.687 Remote Similarity NPD6371 Approved
0.6832 Remote Similarity NPD6110 Phase 1
0.6796 Remote Similarity NPD4249 Approved
0.6792 Remote Similarity NPD7983 Approved
0.6752 Remote Similarity NPD6053 Discontinued
0.6746 Remote Similarity NPD7319 Approved
0.6731 Remote Similarity NPD4250 Approved
0.6731 Remote Similarity NPD4251 Approved
0.6698 Remote Similarity NPD7838 Discovery
0.6667 Remote Similarity NPD7154 Phase 3
0.6613 Remote Similarity NPD7830 Approved
0.6613 Remote Similarity NPD7829 Approved
0.6612 Remote Similarity NPD7328 Approved
0.6612 Remote Similarity NPD7327 Approved
0.6609 Remote Similarity NPD6412 Phase 2
0.6602 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6587 Remote Similarity NPD8074 Phase 3
0.6585 Remote Similarity NPD8033 Approved
0.6577 Remote Similarity NPD4225 Approved
0.6557 Remote Similarity NPD7516 Approved
0.6504 Remote Similarity NPD8377 Approved
0.6504 Remote Similarity NPD8294 Approved
0.648 Remote Similarity NPD7642 Approved
0.6475 Remote Similarity NPD7641 Discontinued
0.6452 Remote Similarity NPD8380 Approved
0.6452 Remote Similarity NPD8379 Approved
0.6452 Remote Similarity NPD8296 Approved
0.6452 Remote Similarity NPD8335 Approved
0.6452 Remote Similarity NPD8378 Approved
0.6449 Remote Similarity NPD1695 Approved
0.6417 Remote Similarity NPD8133 Approved
0.6396 Remote Similarity NPD7839 Suspended
0.6393 Remote Similarity NPD7115 Discovery
0.6381 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6378 Remote Similarity NPD8451 Approved
0.6373 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6346 Remote Similarity NPD5362 Discontinued
0.633 Remote Similarity NPD7637 Suspended
0.6328 Remote Similarity NPD8448 Approved
0.632 Remote Similarity NPD8444 Approved
0.6316 Remote Similarity NPD5344 Discontinued
0.6306 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6299 Remote Similarity NPD8299 Approved
0.6299 Remote Similarity NPD8342 Approved
0.6299 Remote Similarity NPD8340 Approved
0.6299 Remote Similarity NPD8341 Approved
0.6273 Remote Similarity NPD5778 Approved
0.6273 Remote Similarity NPD5779 Approved
0.626 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6239 Remote Similarity NPD5785 Approved
0.6228 Remote Similarity NPD7639 Approved
0.6228 Remote Similarity NPD7640 Approved
0.6226 Remote Similarity NPD6082 Clinical (unspecified phase)
0.622 Remote Similarity NPD8328 Phase 3
0.6218 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6216 Remote Similarity NPD5282 Discontinued
0.6183 Remote Similarity NPD8392 Approved
0.6183 Remote Similarity NPD8390 Approved
0.6183 Remote Similarity NPD8391 Approved
0.6176 Remote Similarity NPD4271 Approved
0.6176 Remote Similarity NPD4268 Approved
0.6148 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6142 Remote Similarity NPD8080 Discontinued
0.614 Remote Similarity NPD7638 Approved
0.6129 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6075 Remote Similarity NPD5363 Approved
0.6068 Remote Similarity NPD1407 Approved
0.6063 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6058 Remote Similarity NPD4252 Approved
0.6058 Remote Similarity NPD4820 Approved
0.6058 Remote Similarity NPD4819 Approved
0.6058 Remote Similarity NPD4822 Approved
0.6058 Remote Similarity NPD4821 Approved
0.6031 Remote Similarity NPD7736 Approved
0.6019 Remote Similarity NPD5786 Approved
0.6019 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6016 Remote Similarity NPD6370 Approved
0.6015 Remote Similarity NPD7260 Phase 2
0.6 Remote Similarity NPD6009 Approved
0.5984 Remote Similarity NPD6319 Approved
0.5954 Remote Similarity NPD8293 Discontinued
0.595 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5948 Remote Similarity NPD6648 Approved
0.5943 Remote Similarity NPD6435 Approved
0.5943 Remote Similarity NPD4270 Approved
0.5943 Remote Similarity NPD4269 Approved
0.5935 Remote Similarity NPD6882 Approved
0.5923 Remote Similarity NPD7492 Approved
0.5909 Remote Similarity NPD8337 Approved
0.5909 Remote Similarity NPD8336 Approved
0.5902 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5888 Remote Similarity NPD5332 Approved
0.5888 Remote Similarity NPD5331 Approved
0.5887 Remote Similarity NPD4632 Approved
0.5878 Remote Similarity NPD6616 Approved
0.5859 Remote Similarity NPD6054 Approved
0.5856 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5856 Remote Similarity NPD6101 Approved
0.5854 Remote Similarity NPD2204 Approved
0.5849 Remote Similarity NPD4790 Discontinued
0.5841 Remote Similarity NPD6399 Phase 3
0.5833 Remote Similarity NPD7078 Approved
0.5818 Remote Similarity NPD7524 Approved
0.5816 Remote Similarity NPD897 Approved
0.5816 Remote Similarity NPD896 Approved
0.5816 Remote Similarity NPD898 Approved
0.5816 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5814 Remote Similarity NPD6015 Approved
0.5814 Remote Similarity NPD6016 Approved
0.5806 Remote Similarity NPD8297 Approved
0.5794 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5794 Remote Similarity NPD5209 Approved
0.5772 Remote Similarity NPD6421 Discontinued
0.5769 Remote Similarity NPD5988 Approved
0.5755 Remote Similarity NPD5368 Approved
0.5752 Remote Similarity NPD6411 Approved
0.5738 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5736 Remote Similarity NPD6059 Approved
0.5735 Remote Similarity NPD6845 Suspended
0.5735 Remote Similarity NPD8338 Approved
0.5726 Remote Similarity NPD6649 Approved
0.5726 Remote Similarity NPD6650 Approved
0.5714 Remote Similarity NPD7632 Discontinued
0.5701 Remote Similarity NPD5369 Approved
0.5691 Remote Similarity NPD6373 Approved
0.5691 Remote Similarity NPD6372 Approved
0.569 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5688 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5679 Remote Similarity NPD7685 Pre-registration
0.566 Remote Similarity NPD7329 Approved
0.5656 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5656 Remote Similarity NPD5697 Approved
0.5639 Remote Similarity NPD8273 Phase 1
0.5636 Remote Similarity NPD1694 Approved
0.5625 Remote Similarity NPD7500 Approved
0.5619 Remote Similarity NPD4756 Discovery
0.5612 Remote Similarity NPD8387 Clinical (unspecified phase)
0.561 Remote Similarity NPD6881 Approved
0.561 Remote Similarity NPD6899 Approved
0.5607 Remote Similarity NPD7332 Phase 2
0.5606 Remote Similarity NPD7122 Discontinued
0.56 Remote Similarity NPD7116 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   442433
ChEMBL   CHEMBL516850
ZINC  

Physicochemical Properties

Molecular Weight:  404.13
ALogP:  -3.4943
MLogP:  2.12
XLogP:  -2.829
# Rotatable Bonds:  13
Polar Surface Area:  175.37
# H-Bond Aceptor:  11
# H-Bond Donor:  6
# Rings:  3
# Heavy Atoms:  28

Download Data

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