Natural Product: NPC280390

Natural Product ID:  NPC280390
Common Name:   Melittoside
IUPAC Name:   (2S,3R,4S,5S,6R)-2-[[(1S,4aS,5R,7aR)-5-hydroxy-7-(hydroxymethyl)-4a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,7a-dihydro-1H-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:  
Molecular Formula:   C21H32O15
Standard InCHIKey:  LZKBAGSBRBMVBE-GVKBFFPQSA-N
Standard InCHI:  InChI=1S/C21H32O15/c22-4-7-3-10(25)21(36-20-17(31)15(29)13(27)9(6-24)34-20)1-2-32-18(11(7)21)35-19-16(30)14(28)12(26)8(5-23)33-19/h1-3,8-20,22-31H,4-6H2/t8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18+,19+,20+,21-/m1/s1
Canonical SMILES:  OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@]3([C@H]2C(=C[C@H]3O)CO)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
NPO13552 Glaucium squamigerum Species Papaveraceae Eukaryota UNPD*
NPO6375 Xylocopa virginica Species Apidae Eukaryota UNPD*
NPO1128 Hoodia gordonii Species Apocynaceae Eukaryota UNPD*
NPO10000 Rehmanniae radix praeparata NA NA NA TCMSP*
NPO8101 Rehmannia glutinosa Species Orobanchaceae Eukaryota TM-MC*
NPO6080 Ericerus pela Species Coccidae Eukaryota TCMID*
NPO17717 Clerodendrum thomsoniae Species Lamiaceae Eukaryota TCMID*
NPO8101 Rehmannia glutinosa Species Orobanchaceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT179 Cell Line A2780 Homo sapiens IC50 > 10000 nM 26859776
NPT2 Others Unspecified IC50 > 10000 nM 26859776
NPT139 Cell Line HT-29 Homo sapiens IC50 > 10000 nM 26859776
NPT81 Cell Line A549 Homo sapiens IC50 > 10000 nM 26859776

  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 NPC280390 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
0.907 High Similarity NPC136699
0.907 High Similarity NPC220167
0.8469 Intermediate Similarity NPC197541
0.8469 Intermediate Similarity NPC267869
0.8469 Intermediate Similarity NPC234304
0.8469 Intermediate Similarity NPC284929
0.8469 Intermediate Similarity NPC118761
0.837 Intermediate Similarity NPC104129
0.837 Intermediate Similarity NPC249408
0.8367 Intermediate Similarity NPC222062
0.8333 Intermediate Similarity NPC470658
0.8265 Intermediate Similarity NPC20673
0.82 Intermediate Similarity NPC86095
0.8163 Intermediate Similarity NPC244878
0.8163 Intermediate Similarity NPC255677
0.8163 Intermediate Similarity NPC22149
0.8163 Intermediate Similarity NPC306344
0.8081 Intermediate Similarity NPC28304
0.8081 Intermediate Similarity NPC298255
0.8065 Intermediate Similarity NPC248312
0.8061 Intermediate Similarity NPC151093
0.8041 Intermediate Similarity NPC241911
0.8 Intermediate Similarity NPC276298
0.8 Intermediate Similarity NPC250545
0.8 Intermediate Similarity NPC13171
0.8 Intermediate Similarity NPC195510
0.7931 Intermediate Similarity NPC229655
0.79 Intermediate Similarity NPC4637
0.79 Intermediate Similarity NPC219038
0.79 Intermediate Similarity NPC98859
0.7895 Intermediate Similarity NPC327253
0.7849 Intermediate Similarity NPC149018
0.7849 Intermediate Similarity NPC171484
0.7826 Intermediate Similarity NPC259296
0.7826 Intermediate Similarity NPC98276
0.7822 Intermediate Similarity NPC471599
0.7822 Intermediate Similarity NPC310804
0.7822 Intermediate Similarity NPC261117
0.7802 Intermediate Similarity NPC20072
0.7766 Intermediate Similarity NPC125142
0.7755 Intermediate Similarity NPC101051
0.7732 Intermediate Similarity NPC320552
0.7732 Intermediate Similarity NPC61201
0.7708 Intermediate Similarity NPC307699
0.7629 Intermediate Similarity NPC274274
0.7629 Intermediate Similarity NPC472125
0.7629 Intermediate Similarity NPC294643
0.7629 Intermediate Similarity NPC473150
0.7629 Intermediate Similarity NPC472126
0.7629 Intermediate Similarity NPC472124
0.7604 Intermediate Similarity NPC93190
0.7604 Intermediate Similarity NPC50464
0.7604 Intermediate Similarity NPC22918
0.76 Intermediate Similarity NPC470684
0.76 Intermediate Similarity NPC470683
0.7586 Intermediate Similarity NPC132938
0.7579 Intermediate Similarity NPC258501
0.7576 Intermediate Similarity NPC469543
0.7576 Intermediate Similarity NPC170204
0.7568 Intermediate Similarity NPC219656
0.7524 Intermediate Similarity NPC254538
0.7524 Intermediate Similarity NPC474285
0.7524 Intermediate Similarity NPC33053
0.75 Intermediate Similarity NPC148534
0.7456 Intermediate Similarity NPC219804
0.7447 Intermediate Similarity NPC266718
0.7434 Intermediate Similarity NPC233500
0.7423 Intermediate Similarity NPC477748
0.7423 Intermediate Similarity NPC299527
0.7404 Intermediate Similarity NPC197736
0.74 Intermediate Similarity NPC291709
0.74 Intermediate Similarity NPC241407
0.7391 Intermediate Similarity NPC127295
0.7391 Intermediate Similarity NPC163362
0.7391 Intermediate Similarity NPC100697
0.7379 Intermediate Similarity NPC21568
0.7379 Intermediate Similarity NPC285231
0.7374 Intermediate Similarity NPC91654
0.7374 Intermediate Similarity NPC67398
0.7374 Intermediate Similarity NPC474792
0.7368 Intermediate Similarity NPC196130
0.7353 Intermediate Similarity NPC90819
0.7353 Intermediate Similarity NPC124181
0.7353 Intermediate Similarity NPC40182
0.7353 Intermediate Similarity NPC198422
0.7347 Intermediate Similarity NPC6414
0.7347 Intermediate Similarity NPC117596
0.7347 Intermediate Similarity NPC202886
0.7347 Intermediate Similarity NPC303451
0.7339 Intermediate Similarity NPC216595
0.7339 Intermediate Similarity NPC473567
0.7333 Intermediate Similarity NPC93352
0.7303 Intermediate Similarity NPC472174
0.729 Intermediate Similarity NPC472897
0.729 Intermediate Similarity NPC472896
0.7282 Intermediate Similarity NPC469942
0.7273 Intermediate Similarity NPC477749
0.7273 Intermediate Similarity NPC302584
0.7264 Intermediate Similarity NPC472900
0.7264 Intermediate Similarity NPC472899
0.7264 Intermediate Similarity NPC472898
0.7263 Intermediate Similarity NPC475035
0.7255 Intermediate Similarity NPC153559
0.7248 Intermediate Similarity NPC472987
0.7248 Intermediate Similarity NPC473021
0.7245 Intermediate Similarity NPC309310
0.7228 Intermediate Similarity NPC6765
0.7228 Intermediate Similarity NPC93869
0.7222 Intermediate Similarity NPC472901
0.7216 Intermediate Similarity NPC475037
0.7212 Intermediate Similarity NPC470434
0.72 Intermediate Similarity NPC238090
0.72 Intermediate Similarity NPC472195
0.72 Intermediate Similarity NPC472196
0.7196 Intermediate Similarity NPC231340
0.7184 Intermediate Similarity NPC473307
0.7172 Intermediate Similarity NPC270908
0.7172 Intermediate Similarity NPC65665
0.7172 Intermediate Similarity NPC216826
0.7172 Intermediate Similarity NPC231710
0.7172 Intermediate Similarity NPC120021
0.7172 Intermediate Similarity NPC470573
0.717 Intermediate Similarity NPC75608
0.7159 Intermediate Similarity NPC474078
0.7157 Intermediate Similarity NPC90583
0.7156 Intermediate Similarity NPC191439
0.7156 Intermediate Similarity NPC170974
0.7156 Intermediate Similarity NPC103627
0.7156 Intermediate Similarity NPC65155
0.7156 Intermediate Similarity NPC141433
0.7143 Intermediate Similarity NPC148965
0.7143 Intermediate Similarity NPC272015
0.7143 Intermediate Similarity NPC201191
0.713 Intermediate Similarity NPC235824
0.7129 Intermediate Similarity NPC294293
0.7129 Intermediate Similarity NPC159698
0.7129 Intermediate Similarity NPC256368
0.7129 Intermediate Similarity NPC274588
0.7117 Intermediate Similarity NPC469348
0.7117 Intermediate Similarity NPC51154
0.7117 Intermediate Similarity NPC469347
0.7117 Intermediate Similarity NPC307642
0.7115 Intermediate Similarity NPC64348
0.7103 Intermediate Similarity NPC474569
0.71 Intermediate Similarity NPC9447
0.7091 Intermediate Similarity NPC13190
0.7087 Intermediate Similarity NPC125551
0.7087 Intermediate Similarity NPC96597
0.7087 Intermediate Similarity NPC155319
0.7087 Intermediate Similarity NPC472290
0.7087 Intermediate Similarity NPC240372
0.7087 Intermediate Similarity NPC91197
0.7087 Intermediate Similarity NPC309503
0.7087 Intermediate Similarity NPC239547
0.7075 Intermediate Similarity NPC473198
0.7064 Intermediate Similarity NPC473318
0.7064 Intermediate Similarity NPC473328
0.7064 Intermediate Similarity NPC250089
0.7064 Intermediate Similarity NPC28844
0.7064 Intermediate Similarity NPC14630
0.7064 Intermediate Similarity NPC157530
0.7048 Intermediate Similarity NPC280991
0.7048 Intermediate Similarity NPC475157
0.7048 Intermediate Similarity NPC216911
0.7048 Intermediate Similarity NPC471637
0.7048 Intermediate Similarity NPC154132
0.7048 Intermediate Similarity NPC57586
0.7048 Intermediate Similarity NPC2313
0.7048 Intermediate Similarity NPC154127
0.7048 Intermediate Similarity NPC475655
0.7041 Intermediate Similarity NPC118077
0.7041 Intermediate Similarity NPC475186
0.7041 Intermediate Similarity NPC471055
0.7041 Intermediate Similarity NPC471056
0.7034 Intermediate Similarity NPC179261
0.7027 Intermediate Similarity NPC112274
0.7027 Intermediate Similarity NPC231797
0.7027 Intermediate Similarity NPC475354
0.7027 Intermediate Similarity NPC42171
0.7019 Intermediate Similarity NPC169468
0.7019 Intermediate Similarity NPC81483
0.7019 Intermediate Similarity NPC61630
0.7019 Intermediate Similarity NPC312325
0.7019 Intermediate Similarity NPC307517
0.7019 Intermediate Similarity NPC158088
0.7018 Intermediate Similarity NPC472080
0.701 Intermediate Similarity NPC477746
0.701 Intermediate Similarity NPC475034
0.701 Intermediate Similarity NPC470124
0.701 Intermediate Similarity NPC477747
0.701 Intermediate Similarity NPC471494
0.701 Intermediate Similarity NPC73166
0.7009 Intermediate Similarity NPC470885
0.7009 Intermediate Similarity NPC187400
0.7009 Intermediate Similarity NPC221562
0.7 Intermediate Similarity NPC472717
0.7 Intermediate Similarity NPC118078
0.699 Remote Similarity NPC161293
0.699 Remote Similarity NPC54731
0.699 Remote Similarity NPC207617

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC280390 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
0.713 Intermediate Similarity NPD7503 Approved
0.6937 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6857 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6838 Remote Similarity NPD8033 Approved
0.6838 Remote Similarity NPD8513 Phase 3
0.6752 Remote Similarity NPD8377 Approved
0.6752 Remote Similarity NPD8294 Approved
0.6724 Remote Similarity NPD7327 Approved
0.6724 Remote Similarity NPD7328 Approved
0.6695 Remote Similarity NPD8515 Approved
0.6695 Remote Similarity NPD8379 Approved
0.6695 Remote Similarity NPD8516 Approved
0.6695 Remote Similarity NPD8517 Approved
0.6695 Remote Similarity NPD8380 Approved
0.6695 Remote Similarity NPD8296 Approved
0.6695 Remote Similarity NPD8335 Approved
0.6695 Remote Similarity NPD8378 Approved
0.6667 Remote Similarity NPD7516 Approved
0.6667 Remote Similarity NPD6686 Approved
0.6373 Remote Similarity NPD4250 Approved
0.6373 Remote Similarity NPD4251 Approved
0.6373 Remote Similarity NPD7524 Approved
0.6346 Remote Similarity NPD6698 Approved
0.6346 Remote Similarity NPD46 Approved
0.6341 Remote Similarity NPD7507 Approved
0.6327 Remote Similarity NPD7332 Phase 2
0.6283 Remote Similarity NPD6412 Phase 2
0.6275 Remote Similarity NPD4249 Approved
0.6239 Remote Similarity NPD8133 Approved
0.6238 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6238 Remote Similarity NPD7338 Clinical (unspecified phase)
0.619 Remote Similarity NPD7319 Approved
0.619 Remote Similarity NPD7838 Discovery
0.6162 Remote Similarity NPD7514 Phase 3
0.616 Remote Similarity NPD8074 Phase 3
0.6154 Remote Similarity NPD6053 Discontinued
0.6139 Remote Similarity NPD6695 Phase 3
0.6139 Remote Similarity NPD7154 Phase 3
0.6126 Remote Similarity NPD5344 Discontinued
0.6038 Remote Similarity NPD8522 Clinical (unspecified phase)
0.6 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5983 Remote Similarity NPD6371 Approved
0.5981 Remote Similarity NPD7637 Suspended
0.5981 Remote Similarity NPD7983 Approved
0.598 Remote Similarity NPD6110 Phase 1
0.596 Remote Similarity NPD7145 Approved
0.596 Remote Similarity NPD7322 Clinical (unspecified phase)
0.5941 Remote Similarity NPD6898 Phase 1
0.5941 Remote Similarity NPD6902 Approved
0.5913 Remote Similarity NPD6640 Phase 3
0.5905 Remote Similarity NPD7750 Discontinued
0.5859 Remote Similarity NPD6932 Approved
0.5859 Remote Similarity NPD6925 Approved
0.5859 Remote Similarity NPD5776 Phase 2
0.5842 Remote Similarity NPD4820 Approved
0.5842 Remote Similarity NPD6930 Phase 2
0.5842 Remote Similarity NPD6931 Approved
0.5842 Remote Similarity NPD4819 Approved
0.5842 Remote Similarity NPD4821 Approved
0.5842 Remote Similarity NPD4822 Approved
0.5827 Remote Similarity NPD8451 Approved
0.5825 Remote Similarity NPD5362 Discontinued
0.58 Remote Similarity NPD4271 Approved
0.58 Remote Similarity NPD4268 Approved
0.5794 Remote Similarity NPD7830 Approved
0.5794 Remote Similarity NPD7829 Approved
0.5781 Remote Similarity NPD8448 Approved
0.5778 Remote Similarity NPD6123 Approved
0.5769 Remote Similarity NPD8392 Approved
0.5769 Remote Similarity NPD8390 Approved
0.5769 Remote Similarity NPD8391 Approved
0.5766 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5752 Remote Similarity NPD7640 Approved
0.5752 Remote Similarity NPD6648 Approved
0.5752 Remote Similarity NPD7639 Approved
0.575 Remote Similarity NPD6429 Approved
0.575 Remote Similarity NPD6430 Approved
0.5748 Remote Similarity NPD8299 Approved
0.5748 Remote Similarity NPD8342 Approved
0.5748 Remote Similarity NPD8341 Approved
0.5748 Remote Similarity NPD8340 Approved
0.5743 Remote Similarity NPD6929 Approved
0.5714 Remote Similarity NPD6370 Approved
0.5714 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5698 Remote Similarity NPD888 Phase 3
0.5698 Remote Similarity NPD893 Approved
0.5698 Remote Similarity NPD891 Phase 3
0.5698 Remote Similarity NPD892 Phase 3
0.5698 Remote Similarity NPD890 Clinical (unspecified phase)
0.5691 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5691 Remote Similarity NPD7115 Discovery
0.5688 Remote Similarity NPD7087 Discontinued
0.5682 Remote Similarity NPD8449 Approved
0.5664 Remote Similarity NPD7638 Approved
0.5639 Remote Similarity NPD8450 Suspended
0.5636 Remote Similarity NPD8171 Discontinued
0.5635 Remote Similarity NPD8444 Approved
0.5631 Remote Similarity NPD4790 Discontinued
0.5625 Remote Similarity NPD1091 Approved
0.5625 Remote Similarity NPD7839 Suspended
0.5607 Remote Similarity NPD4751 Clinical (unspecified phase)
0.56 Remote Similarity NPD6933 Approved

Structure

External Identifiers

PubChem CID   11968737
ChEMBL   CHEMBL3810093
ZINC  

Physicochemical Properties

Molecular Weight:  524.17
ALogP:  -5.7677
MLogP:  2.12
XLogP:  -4.445
# Rotatable Bonds:  17
Polar Surface Area:  248.45
# H-Bond Aceptor:  15
# H-Bond Donor:  10
# Rings:  4
# Heavy Atoms:  36

Download Data

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