Natural Product: NPC34581

Natural Product ID:  NPC34581
Common Name:   Citroside B
IUPAC Name:   4-[(4S,6R)-4-hydroxy-2,2,6-trimethyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexylidene]but-3-en-2-one
Synonyms:   Citroside B
Molecular Formula:   C19H30O8
Standard InCHIKey:  XTODSGVDHGMKSN-SIEIHWOKSA-N
Standard InCHI:  InChI=1S/C19H30O8/c1-10(21)5-6-13-18(2,3)7-11(22)8-19(13,4)27-17-16(25)15(24)14(23)12(9-20)26-17/h5,11-12,14-17,20,22-25H,7-9H2,1-4H3/t6?,11-,12+,14+,15-,16+,17-,19+/m0/s1
Canonical SMILES:  OC[C@H]1O[C@@H](O[C@]2(C)C[C@@H](O)CC(C2=C=CC(=O)C)(C)C)[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
NPO29956 Sanicula lamelligera Species Apiaceae Eukaryota Whole plants Mountain Emei, Sichuan Province, China 2008-OCT PMID[21561060]
NPO29956 Sanicula lamelligera Species Apiaceae Eukaryota Whole Plants PMID[21561060]
NPO23706 Breea segeta NA NA NA TM-MC*
NPO11697 Cirsium setosum Species Asteraceae Eukaryota TM-MC*
NPO23548 Leonurus japonicus Species Lamiaceae Eukaryota TM-MC*
NPO2345 Coriandrum sativum Species Apiaceae Eukaryota TCMID*
NPO27665 Erythroxylum cambodianum Species Erythroxylaceae Eukaryota TCMID*
NPO25618 Eriobotrya japonica Species Rosaceae Eukaryota TCMID*
NPO19755 Artemisia anomala Species Asteraceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT83 Cell Line MCF7 Homo sapiens IC50 > 64400 nM 21561060
NPT81 Cell Line A549 Homo sapiens IC50 > 64400 nM 21561060
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 > 64400 nM 21561060
NPT116 Cell Line HL-60 Homo sapiens IC50 > 64400 nM 21561060
NPT113 Cell Line RAW264.7 Mus musculus IC50 > 64400 nM 21561060
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 > 259100 nM 21561060
NPT1452 Cell Line C8166 Homo sapiens CC50 > 259100 nM 21561060
NPT660 Cell Line SW480 Homo sapiens IC50 > 64400 nM 21561060

  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 NPC34581 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
0.8132 Intermediate Similarity NPC474835
0.8041 Intermediate Similarity NPC194941
0.7912 Intermediate Similarity NPC474249
0.7912 Intermediate Similarity NPC261990
0.7835 Intermediate Similarity NPC214277
0.7789 Intermediate Similarity NPC125551
0.7789 Intermediate Similarity NPC91197
0.7789 Intermediate Similarity NPC309503
0.7789 Intermediate Similarity NPC239547
0.7789 Intermediate Similarity NPC155319
0.7789 Intermediate Similarity NPC96597
0.7755 Intermediate Similarity NPC473070
0.7742 Intermediate Similarity NPC91654
0.7742 Intermediate Similarity NPC67398
0.7742 Intermediate Similarity NPC474792
0.7732 Intermediate Similarity NPC198992
0.7732 Intermediate Similarity NPC280991
0.7708 Intermediate Similarity NPC81483
0.7708 Intermediate Similarity NPC169468
0.7708 Intermediate Similarity NPC312325
0.7708 Intermediate Similarity NPC307517
0.7708 Intermediate Similarity NPC61630
0.7677 Intermediate Similarity NPC473068
0.766 Intermediate Similarity NPC25701
0.766 Intermediate Similarity NPC2003
0.7653 Intermediate Similarity NPC150463
0.7634 Intermediate Similarity NPC289361
0.7609 Intermediate Similarity NPC477748
0.76 Intermediate Similarity NPC239961
0.7576 Intermediate Similarity NPC151516
0.7551 Intermediate Similarity NPC154127
0.7527 Intermediate Similarity NPC202886
0.7526 Intermediate Similarity NPC198422
0.7526 Intermediate Similarity NPC40182
0.75 Intermediate Similarity NPC248312
0.75 Intermediate Similarity NPC471755
0.75 Intermediate Similarity NPC90583
0.75 Intermediate Similarity NPC471756
0.7475 Intermediate Similarity NPC121423
0.7475 Intermediate Similarity NPC223834
0.7451 Intermediate Similarity NPC473069
0.7447 Intermediate Similarity NPC477749
0.7447 Intermediate Similarity NPC302584
0.7426 Intermediate Similarity NPC82251
0.7423 Intermediate Similarity NPC474194
0.7419 Intermediate Similarity NPC309310
0.7396 Intermediate Similarity NPC108141
0.7379 Intermediate Similarity NPC206618
0.7375 Intermediate Similarity NPC86856
0.7353 Intermediate Similarity NPC472390
0.7349 Intermediate Similarity NPC474078
0.7347 Intermediate Similarity NPC70733
0.7347 Intermediate Similarity NPC477928
0.7347 Intermediate Similarity NPC56071
0.7326 Intermediate Similarity NPC229655
0.732 Intermediate Similarity NPC256230
0.7308 Intermediate Similarity NPC83005
0.7308 Intermediate Similarity NPC46407
0.7303 Intermediate Similarity NPC16090
0.73 Intermediate Similarity NPC201191
0.7292 Intermediate Similarity NPC96736
0.7292 Intermediate Similarity NPC211238
0.7292 Intermediate Similarity NPC477927
0.7292 Intermediate Similarity NPC178949
0.7292 Intermediate Similarity NPC72817
0.7282 Intermediate Similarity NPC177524
0.7282 Intermediate Similarity NPC38948
0.7282 Intermediate Similarity NPC219900
0.7282 Intermediate Similarity NPC392
0.7273 Intermediate Similarity NPC80471
0.7273 Intermediate Similarity NPC5908
0.7273 Intermediate Similarity NPC110373
0.7264 Intermediate Similarity NPC75167
0.7264 Intermediate Similarity NPC311592
0.7255 Intermediate Similarity NPC470763
0.7255 Intermediate Similarity NPC85670
0.7255 Intermediate Similarity NPC470767
0.7253 Intermediate Similarity NPC266718
0.7253 Intermediate Similarity NPC166279
0.7253 Intermediate Similarity NPC475035
0.725 Intermediate Similarity NPC31496
0.7245 Intermediate Similarity NPC240372
0.7228 Intermediate Similarity NPC473123
0.7228 Intermediate Similarity NPC473124
0.7222 Intermediate Similarity NPC473852
0.7222 Intermediate Similarity NPC77319
0.7222 Intermediate Similarity NPC474418
0.7222 Intermediate Similarity NPC471351
0.7222 Intermediate Similarity NPC50305
0.7222 Intermediate Similarity NPC27507
0.7222 Intermediate Similarity NPC244402
0.7222 Intermediate Similarity NPC471354
0.7222 Intermediate Similarity NPC243196
0.7222 Intermediate Similarity NPC157376
0.7222 Intermediate Similarity NPC99728
0.7222 Intermediate Similarity NPC196429
0.7222 Intermediate Similarity NPC142066
0.7222 Intermediate Similarity NPC84987
0.7222 Intermediate Similarity NPC87250
0.7222 Intermediate Similarity NPC471353
0.7222 Intermediate Similarity NPC309034
0.7222 Intermediate Similarity NPC158344
0.7222 Intermediate Similarity NPC471355
0.7222 Intermediate Similarity NPC20072
0.7222 Intermediate Similarity NPC34390
0.7204 Intermediate Similarity NPC475037
0.7196 Intermediate Similarity NPC181145
0.7191 Intermediate Similarity NPC127295
0.7191 Intermediate Similarity NPC163362
0.7191 Intermediate Similarity NPC100697
0.7188 Intermediate Similarity NPC472196
0.7188 Intermediate Similarity NPC320089
0.7188 Intermediate Similarity NPC472195
0.7188 Intermediate Similarity NPC238090
0.7184 Intermediate Similarity NPC122816
0.7174 Intermediate Similarity NPC477747
0.7174 Intermediate Similarity NPC477746
0.7172 Intermediate Similarity NPC157739
0.7159 Intermediate Similarity NPC272841
0.7158 Intermediate Similarity NPC117596
0.7158 Intermediate Similarity NPC327253
0.7157 Intermediate Similarity NPC203354
0.7157 Intermediate Similarity NPC473127
0.7157 Intermediate Similarity NPC110656
0.7157 Intermediate Similarity NPC470768
0.7156 Intermediate Similarity NPC83287
0.7143 Intermediate Similarity NPC177047
0.7143 Intermediate Similarity NPC472989
0.7143 Intermediate Similarity NPC103627
0.7143 Intermediate Similarity NPC170974
0.7143 Intermediate Similarity NPC143446
0.7143 Intermediate Similarity NPC471879
0.7143 Intermediate Similarity NPC191439
0.713 Intermediate Similarity NPC99620
0.713 Intermediate Similarity NPC193382
0.713 Intermediate Similarity NPC5311
0.713 Intermediate Similarity NPC199428
0.713 Intermediate Similarity NPC310341
0.7129 Intermediate Similarity NPC470571
0.7129 Intermediate Similarity NPC472815
0.7115 Intermediate Similarity NPC272576
0.7115 Intermediate Similarity NPC48548
0.7115 Intermediate Similarity NPC135015
0.7115 Intermediate Similarity NPC128795
0.7115 Intermediate Similarity NPC473288
0.7115 Intermediate Similarity NPC217921
0.7113 Intermediate Similarity NPC305160
0.7113 Intermediate Similarity NPC159698
0.7113 Intermediate Similarity NPC294293
0.7103 Intermediate Similarity NPC264153
0.7103 Intermediate Similarity NPC473159
0.71 Intermediate Similarity NPC130792
0.71 Intermediate Similarity NPC64348
0.7093 Intermediate Similarity NPC308489
0.7087 Intermediate Similarity NPC473199
0.7087 Intermediate Similarity NPC51719
0.7087 Intermediate Similarity NPC41681
0.7083 Intermediate Similarity NPC472124
0.7083 Intermediate Similarity NPC472125
0.7083 Intermediate Similarity NPC472126
0.7071 Intermediate Similarity NPC473555
0.7071 Intermediate Similarity NPC471770
0.7071 Intermediate Similarity NPC278939
0.7071 Intermediate Similarity NPC278506
0.7064 Intermediate Similarity NPC203862
0.7064 Intermediate Similarity NPC152615
0.7064 Intermediate Similarity NPC93883
0.7059 Intermediate Similarity NPC281378
0.7059 Intermediate Similarity NPC120009
0.7053 Intermediate Similarity NPC470819
0.7048 Intermediate Similarity NPC473328
0.7048 Intermediate Similarity NPC316974
0.7048 Intermediate Similarity NPC473318
0.7048 Intermediate Similarity NPC472901
0.7048 Intermediate Similarity NPC257853
0.7048 Intermediate Similarity NPC28844
0.7048 Intermediate Similarity NPC8431
0.7048 Intermediate Similarity NPC473570
0.7048 Intermediate Similarity NPC40728
0.7037 Intermediate Similarity NPC69576
0.7037 Intermediate Similarity NPC84949
0.7037 Intermediate Similarity NPC106446
0.7037 Intermediate Similarity NPC31354
0.7037 Intermediate Similarity NPC471633
0.703 Intermediate Similarity NPC11974
0.703 Intermediate Similarity NPC129372
0.703 Intermediate Similarity NPC309425
0.703 Intermediate Similarity NPC472023
0.703 Intermediate Similarity NPC88000
0.703 Intermediate Similarity NPC472554
0.703 Intermediate Similarity NPC285231
0.703 Intermediate Similarity NPC47566
0.703 Intermediate Similarity NPC160734
0.703 Intermediate Similarity NPC4831
0.703 Intermediate Similarity NPC477717
0.703 Intermediate Similarity NPC21568
0.7027 Intermediate Similarity NPC475556
0.7027 Intermediate Similarity NPC48692
0.7027 Intermediate Similarity NPC475629
0.7027 Intermediate Similarity NPC474466

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC34581 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
0.7282 Intermediate Similarity NPD6686 Approved
0.7156 Intermediate Similarity NPD7328 Approved
0.7156 Intermediate Similarity NPD7327 Approved
0.7091 Intermediate Similarity NPD7516 Approved
0.6964 Remote Similarity NPD8380 Approved
0.6964 Remote Similarity NPD8379 Approved
0.6964 Remote Similarity NPD8296 Approved
0.6964 Remote Similarity NPD8378 Approved
0.6964 Remote Similarity NPD8335 Approved
0.6944 Remote Similarity NPD8133 Approved
0.6875 Remote Similarity NPD8377 Approved
0.6875 Remote Similarity NPD8294 Approved
0.6857 Remote Similarity NPD6412 Phase 2
0.6814 Remote Similarity NPD7503 Approved
0.6814 Remote Similarity NPD8033 Approved
0.6636 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6581 Remote Similarity NPD7507 Approved
0.6574 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6555 Remote Similarity NPD7319 Approved
0.6505 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6465 Remote Similarity NPD6698 Approved
0.6465 Remote Similarity NPD46 Approved
0.6381 Remote Similarity NPD5344 Discontinued
0.6364 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6354 Remote Similarity NPD6400 Clinical (unspecified phase)
0.63 Remote Similarity NPD7838 Discovery
0.6273 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6271 Remote Similarity NPD8328 Phase 3
0.619 Remote Similarity NPD4225 Approved
0.6162 Remote Similarity NPD7524 Approved
0.6161 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6154 Remote Similarity NPD1810 Approved
0.6154 Remote Similarity NPD1811 Approved
0.6102 Remote Similarity NPD6921 Approved
0.6082 Remote Similarity NPD3669 Approved
0.6082 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6071 Remote Similarity NPD5955 Clinical (unspecified phase)
0.605 Remote Similarity NPD6370 Approved
0.6038 Remote Similarity NPD7638 Approved
0.6034 Remote Similarity NPD8295 Clinical (unspecified phase)
0.602 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6019 Remote Similarity NPD8171 Discontinued
0.6 Remote Similarity NPD890 Clinical (unspecified phase)
0.6 Remote Similarity NPD893 Approved
0.6 Remote Similarity NPD891 Phase 3
0.6 Remote Similarity NPD888 Phase 3
0.6 Remote Similarity NPD892 Phase 3
0.5981 Remote Similarity NPD7639 Approved
0.5981 Remote Similarity NPD6648 Approved
0.5981 Remote Similarity NPD7640 Approved
0.5966 Remote Similarity NPD8517 Approved
0.5966 Remote Similarity NPD8513 Phase 3
0.5966 Remote Similarity NPD8515 Approved
0.5966 Remote Similarity NPD8516 Approved
0.5949 Remote Similarity NPD905 Approved
0.5949 Remote Similarity NPD904 Phase 3
0.5918 Remote Similarity NPD6695 Phase 3
0.5909 Remote Similarity NPD8170 Clinical (unspecified phase)
0.5882 Remote Similarity NPD6059 Approved
0.5882 Remote Similarity NPD6054 Approved
0.5875 Remote Similarity NPD2269 Approved
0.5862 Remote Similarity NPD371 Approved
0.5854 Remote Similarity NPD8293 Discontinued
0.5833 Remote Similarity NPD6015 Approved
0.5833 Remote Similarity NPD6016 Approved
0.5825 Remote Similarity NPD3168 Discontinued
0.5824 Remote Similarity NPD2686 Approved
0.5824 Remote Similarity NPD2687 Approved
0.5824 Remote Similarity NPD2254 Approved
0.5806 Remote Similarity NPD7736 Approved
0.5804 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5802 Remote Similarity NPD887 Approved
0.5802 Remote Similarity NPD895 Approved
0.5802 Remote Similarity NPD889 Approved
0.5802 Remote Similarity NPD894 Approved
0.5789 Remote Similarity NPD6371 Approved
0.5785 Remote Similarity NPD5988 Approved
0.5763 Remote Similarity NPD6009 Approved
0.575 Remote Similarity NPD6319 Approved
0.5738 Remote Similarity NPD7642 Approved
0.5738 Remote Similarity NPD6067 Discontinued
0.5698 Remote Similarity NPD6123 Approved
0.5691 Remote Similarity NPD7492 Approved
0.569 Remote Similarity NPD6882 Approved
0.5686 Remote Similarity NPD7750 Discontinued
0.566 Remote Similarity NPD5282 Discontinued
0.5645 Remote Similarity NPD6616 Approved
0.5645 Remote Similarity NPD8451 Approved
0.5641 Remote Similarity NPD4632 Approved
0.563 Remote Similarity NPD7115 Discovery
0.5619 Remote Similarity NPD7983 Approved
0.5619 Remote Similarity NPD7637 Suspended
0.5612 Remote Similarity NPD6931 Approved
0.5612 Remote Similarity NPD6930 Phase 2
0.561 Remote Similarity NPD7829 Approved
0.561 Remote Similarity NPD7830 Approved
0.56 Remote Similarity NPD8448 Approved
0.56 Remote Similarity NPD7078 Approved

Structure

External Identifiers

PubChem CID   14312562
ChEMBL   CHEMBL1814429
ZINC  

Physicochemical Properties

Molecular Weight:  386.19
ALogP:  -1.1243
MLogP:  2.67
XLogP:  1.223
# Rotatable Bonds:  13
Polar Surface Area:  136.68
# H-Bond Aceptor:  8
# H-Bond Donor:  5
# Rings:  2
# Heavy Atoms:  27

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Biological Activities  
Similar NPs/Drugs