Natural Product: NPC149018

Natural Product ID:  NPC149018
Common Name:   Harpagide
IUPAC Name:   (1S,4aS,5R,7S,7aR)-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4a,5,7-triol
Synonyms:  
Molecular Formula:   C15H24O10
Standard InCHIKey:  XUWSHXDEJOOIND-YYDKPPGPSA-N
Standard InCHI:  InChI=1S/C15H24O10/c1-14(21)4-7(17)15(22)2-3-23-13(11(14)15)25-12-10(20)9(19)8(18)6(5-16)24-12/h2-3,6-13,16-22H,4-5H2,1H3/t6-,7-,8-,9+,10-,11-,12+,13+,14+,15-/m1/s1
Canonical SMILES:  OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@]3([C@H]2[C@@](C)(O)C[C@H]3O)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
NPO4937 Pedicularis artselaeri Species Orobanchaceae Eukaryota UNPD*
NPO1869 Schizanthus grahamii Species Solanaceae Eukaryota UNPD*
NPO8894 Lobelia fistulosa Species Campanulaceae Eukaryota UNPD*
NPO9288 Litsea dealbata Species Lauraceae Eukaryota UNPD*
NPO10859 Myoporum laetum Species Scrophulariaceae Eukaryota UNPD*
NPO12201 Pteronia divaricata Species Asteraceae Eukaryota UNPD*
NPO1132 Aster mongolicus Species Asteraceae Eukaryota UNPD*
NPO11664 Thelenota ananas Species Stichopodidae Eukaryota UNPD*
NPO9917 Plagiomnium cuspidatum Species Mniaceae Eukaryota UNPD*
NPO12179 Syzygium malaccense Species Myrtaceae Eukaryota UNPD*
NPO28450 Phyllanthus emblica Species Phyllanthaceae Eukaryota UNPD*
NPO3076 Cordyline australis Species Asparagaceae Eukaryota UNPD*
NPO17306 Dryopteris championii Species Dryopteridaceae Eukaryota UNPD*
NPO4497 Plantago hostifolia Species Plantaginaceae Eukaryota UNPD*
NPO6453 Schizophyllum commune Species Schizophyllaceae Eukaryota UNPD*
NPO16055 Klyxum molle Species Alcyoniidae Eukaryota UNPD*
NPO1976 Sapium pachystachys Species Euphorbiaceae Eukaryota UNPD*
NPO9735 Campnosperma panamense Species Anacardiaceae Eukaryota UNPD*
NPO448 Millettia usaramensis Species Fabaceae Eukaryota UNPD*
NPO803 Adonis annua Species Ranunculaceae Eukaryota UNPD*
NPO17539 Ajuga decumbens Species Lamiaceae Eukaryota TM-MC*
NPO5565 Harpagophytum procumbens Species Pedaliaceae Eukaryota TM-MC*
NPO21021 Hemisteptia lyrata Species Asteraceae Eukaryota UNPD*
NPO6541 Scrophularia buergeriana Species Scrophulariaceae Eukaryota TM-MC*
NPO4647 Leptothyrsa sprucei NA NA NA UNPD*
NPO4802 Scrophularia ningpoensis Species Scrophulariaceae Eukaryota TM-MC*
NPO11352 Centaurea cyanus Species Asteraceae Eukaryota UNPD*
NPO2226 Nauclea latifolia Species Rubiaceae Eukaryota UNPD*
NPO14756 Ilex goshiensis Species Aquifoliaceae Eukaryota UNPD*
NPO523 Tussilago farfara Species Asteraceae Eukaryota UNPD*
NPO13547 Amycolatopsis orientalis Species Pseudonocardiaceae Bacteria UNPD*
NPO1419 Corynebacterium ammoniagenes Species Corynebacteriaceae Bacteria UNPD*
NPO13557 Coniochaeta hoffmannii Species Coniochaetaceae Eukaryota UNPD*
NPO11307.1 Wigandia urens var. caracasana Varieties Namaceae Eukaryota UNPD*

  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 NPC149018 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 NPC171484
0.9506 High Similarity NPC98276
0.9506 High Similarity NPC259296
0.9412 High Similarity NPC274274
0.9412 High Similarity NPC473150
0.9412 High Similarity NPC294643
0.9286 High Similarity NPC148534
0.9176 High Similarity NPC93190
0.9176 High Similarity NPC22918
0.9167 High Similarity NPC258501
0.8953 High Similarity NPC50464
0.875 High Similarity NPC276298
0.828 Intermediate Similarity NPC470683
0.828 Intermediate Similarity NPC470684
0.8161 Intermediate Similarity NPC136699
0.8161 Intermediate Similarity NPC220167
0.7849 Intermediate Similarity NPC280390
0.7742 Intermediate Similarity NPC235051
0.77 Intermediate Similarity NPC127235
0.7684 Intermediate Similarity NPC6765
0.7684 Intermediate Similarity NPC93869
0.7653 Intermediate Similarity NPC216911
0.7647 Intermediate Similarity NPC279575
0.7604 Intermediate Similarity NPC284063
0.7586 Intermediate Similarity NPC170595
0.7579 Intermediate Similarity NPC274588
0.7576 Intermediate Similarity NPC304163
0.7551 Intermediate Similarity NPC476211
0.7551 Intermediate Similarity NPC476320
0.7549 Intermediate Similarity NPC110701
0.7527 Intermediate Similarity NPC299527
0.7526 Intermediate Similarity NPC86843
0.75 Intermediate Similarity NPC329834
0.75 Intermediate Similarity NPC470660
0.75 Intermediate Similarity NPC470659
0.7475 Intermediate Similarity NPC476230
0.7475 Intermediate Similarity NPC287539
0.7475 Intermediate Similarity NPC27474
0.7475 Intermediate Similarity NPC3488
0.7451 Intermediate Similarity NPC148270
0.7451 Intermediate Similarity NPC197813
0.7451 Intermediate Similarity NPC80338
0.7423 Intermediate Similarity NPC170527
0.7423 Intermediate Similarity NPC161293
0.7404 Intermediate Similarity NPC193741
0.7353 Intermediate Similarity NPC170432
0.7327 Intermediate Similarity NPC329704
0.7327 Intermediate Similarity NPC475928
0.7327 Intermediate Similarity NPC37240
0.73 Intermediate Similarity NPC476228
0.73 Intermediate Similarity NPC20673
0.7294 Intermediate Similarity NPC248427
0.7283 Intermediate Similarity NPC470658
0.7264 Intermediate Similarity NPC475851
0.7264 Intermediate Similarity NPC475924
0.7228 Intermediate Similarity NPC35185
0.7228 Intermediate Similarity NPC177013
0.7228 Intermediate Similarity NPC4899
0.7228 Intermediate Similarity NPC474730
0.7216 Intermediate Similarity NPC63897
0.72 Intermediate Similarity NPC91497
0.72 Intermediate Similarity NPC244878
0.7182 Intermediate Similarity NPC219656
0.7158 Intermediate Similarity NPC249408
0.7158 Intermediate Similarity NPC104129
0.71 Intermediate Similarity NPC469919
0.71 Intermediate Similarity NPC469918
0.71 Intermediate Similarity NPC117066
0.71 Intermediate Similarity NPC223700
0.71 Intermediate Similarity NPC37866
0.71 Intermediate Similarity NPC151093
0.71 Intermediate Similarity NPC96399
0.7083 Intermediate Similarity NPC117596
0.7071 Intermediate Similarity NPC241911
0.7054 Intermediate Similarity NPC233500
0.703 Intermediate Similarity NPC471247
0.703 Intermediate Similarity NPC22149
0.703 Intermediate Similarity NPC306344
0.703 Intermediate Similarity NPC255677
0.7019 Intermediate Similarity NPC474569
0.701 Intermediate Similarity NPC472124
0.701 Intermediate Similarity NPC472126
0.701 Intermediate Similarity NPC472125
0.701 Intermediate Similarity NPC66504
0.7 Intermediate Similarity NPC472290
0.7 Intermediate Similarity NPC76486
0.6991 Remote Similarity NPC196130
0.6989 Remote Similarity NPC116613
0.6981 Remote Similarity NPC208307
0.697 Remote Similarity NPC101051
0.6961 Remote Similarity NPC470168
0.6961 Remote Similarity NPC298255
0.6961 Remote Similarity NPC4637
0.6961 Remote Similarity NPC98859
0.6961 Remote Similarity NPC219038
0.6961 Remote Similarity NPC28304
0.6957 Remote Similarity NPC20072
0.6951 Remote Similarity NPC31496
0.6944 Remote Similarity NPC473567
0.6944 Remote Similarity NPC216595
0.6939 Remote Similarity NPC61201
0.6937 Remote Similarity NPC472080
0.693 Remote Similarity NPC219804
0.6923 Remote Similarity NPC100697
0.6923 Remote Similarity NPC312774
0.6923 Remote Similarity NPC86095
0.6907 Remote Similarity NPC307699
0.69 Remote Similarity NPC474297
0.6893 Remote Similarity NPC195510
0.6893 Remote Similarity NPC471599
0.6893 Remote Similarity NPC13171
0.6893 Remote Similarity NPC106668
0.6887 Remote Similarity NPC472896
0.6887 Remote Similarity NPC472897
0.6882 Remote Similarity NPC260852
0.6875 Remote Similarity NPC248312
0.6875 Remote Similarity NPC475991
0.6863 Remote Similarity NPC469942
0.686 Remote Similarity NPC474078
0.6857 Remote Similarity NPC472900
0.6857 Remote Similarity NPC472898
0.6857 Remote Similarity NPC26798
0.6857 Remote Similarity NPC472899
0.6854 Remote Similarity NPC229655
0.6837 Remote Similarity NPC48463
0.6832 Remote Similarity NPC58267
0.6832 Remote Similarity NPC263674
0.6832 Remote Similarity NPC261372
0.6827 Remote Similarity NPC197541
0.6827 Remote Similarity NPC234304
0.6827 Remote Similarity NPC118761
0.6827 Remote Similarity NPC267869
0.6827 Remote Similarity NPC27687
0.6827 Remote Similarity NPC473198
0.6827 Remote Similarity NPC284929
0.6822 Remote Similarity NPC42482
0.6822 Remote Similarity NPC40440
0.68 Remote Similarity NPC473348
0.68 Remote Similarity NPC30477
0.6796 Remote Similarity NPC470434
0.6792 Remote Similarity NPC226642
0.6792 Remote Similarity NPC470170
0.6792 Remote Similarity NPC470169
0.6792 Remote Similarity NPC33053
0.6789 Remote Similarity NPC19888
0.6789 Remote Similarity NPC477050
0.6771 Remote Similarity NPC31349
0.6768 Remote Similarity NPC470187
0.6765 Remote Similarity NPC158088
0.6765 Remote Similarity NPC157739
0.6762 Remote Similarity NPC475365
0.6762 Remote Similarity NPC75608
0.6762 Remote Similarity NPC475521
0.6762 Remote Similarity NPC474464
0.6759 Remote Similarity NPC141433
0.6735 Remote Similarity NPC197107
0.6735 Remote Similarity NPC327253
0.6735 Remote Similarity NPC474249
0.6735 Remote Similarity NPC261990
0.6733 Remote Similarity NPC472989
0.6733 Remote Similarity NPC207617
0.6731 Remote Similarity NPC250545
0.6731 Remote Similarity NPC222062
0.6731 Remote Similarity NPC261117
0.6731 Remote Similarity NPC310804
0.6731 Remote Similarity NPC272015
0.6731 Remote Similarity NPC136816
0.6729 Remote Similarity NPC235824
0.6727 Remote Similarity NPC307642
0.6727 Remote Similarity NPC287075
0.6723 Remote Similarity NPC276047
0.6723 Remote Similarity NPC267733
0.6705 Remote Similarity NPC132938
0.6699 Remote Similarity NPC471242
0.6698 Remote Similarity NPC474015
0.6698 Remote Similarity NPC473476
0.6698 Remote Similarity NPC242748
0.6698 Remote Similarity NPC181845
0.6698 Remote Similarity NPC473923
0.6697 Remote Similarity NPC197231
0.6697 Remote Similarity NPC477028
0.6697 Remote Similarity NPC477032
0.6697 Remote Similarity NPC124677
0.6667 Remote Similarity NPC250836
0.6667 Remote Similarity NPC470657
0.6667 Remote Similarity NPC304445
0.6667 Remote Similarity NPC147292
0.6667 Remote Similarity NPC236580
0.6667 Remote Similarity NPC15978
0.6667 Remote Similarity NPC128133
0.6667 Remote Similarity NPC471770
0.6667 Remote Similarity NPC278939
0.6667 Remote Similarity NPC106446
0.6667 Remote Similarity NPC302584
0.6667 Remote Similarity NPC475701
0.6667 Remote Similarity NPC473555
0.6667 Remote Similarity NPC473890
0.6667 Remote Similarity NPC243728
0.6636 Remote Similarity NPC254255
0.6636 Remote Similarity NPC473469

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC149018 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
0.6667 Remote Similarity NPD4249 Approved
0.6609 Remote Similarity NPD7503 Approved
0.6598 Remote Similarity NPD4251 Approved
0.6598 Remote Similarity NPD4250 Approved
0.6325 Remote Similarity NPD8033 Approved
0.6263 Remote Similarity NPD7524 Approved
0.6211 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6207 Remote Similarity NPD7327 Approved
0.6207 Remote Similarity NPD7328 Approved
0.6182 Remote Similarity NPD6412 Phase 2
0.6154 Remote Similarity NPD7516 Approved
0.6122 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6117 Remote Similarity NPD8171 Discontinued
0.6102 Remote Similarity NPD8294 Approved
0.6102 Remote Similarity NPD8377 Approved
0.605 Remote Similarity NPD8335 Approved
0.605 Remote Similarity NPD8378 Approved
0.605 Remote Similarity NPD8379 Approved
0.605 Remote Similarity NPD8296 Approved
0.605 Remote Similarity NPD8380 Approved
0.6042 Remote Similarity NPD4819 Approved
0.6042 Remote Similarity NPD4821 Approved
0.6042 Remote Similarity NPD4820 Approved
0.6042 Remote Similarity NPD4822 Approved
0.602 Remote Similarity NPD6695 Phase 3
0.6 Remote Similarity NPD8133 Approved
0.6 Remote Similarity NPD4268 Approved
0.6 Remote Similarity NPD4271 Approved
0.5981 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5965 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5926 Remote Similarity NPD890 Clinical (unspecified phase)
0.5926 Remote Similarity NPD895 Approved
0.5926 Remote Similarity NPD891 Phase 3
0.5926 Remote Similarity NPD889 Approved
0.5926 Remote Similarity NPD892 Phase 3
0.5926 Remote Similarity NPD894 Approved
0.5926 Remote Similarity NPD888 Phase 3
0.5926 Remote Similarity NPD893 Approved
0.5926 Remote Similarity NPD887 Approved
0.5917 Remote Similarity NPD8513 Phase 3
0.5875 Remote Similarity NPD904 Phase 3
0.5875 Remote Similarity NPD905 Approved
0.5854 Remote Similarity NPD7507 Approved
0.5841 Remote Similarity NPD6686 Approved
0.5785 Remote Similarity NPD8515 Approved
0.5785 Remote Similarity NPD8517 Approved
0.5785 Remote Similarity NPD8516 Approved
0.5784 Remote Similarity NPD7750 Discontinued
0.5776 Remote Similarity NPD6053 Discontinued
0.5769 Remote Similarity NPD8522 Clinical (unspecified phase)
0.5745 Remote Similarity NPD1811 Approved
0.5745 Remote Similarity NPD1810 Approved
0.5738 Remote Similarity NPD6370 Approved
0.5714 Remote Similarity NPD7514 Phase 3
0.5714 Remote Similarity NPD2267 Suspended
0.5714 Remote Similarity NPD6930 Phase 2
0.5714 Remote Similarity NPD6931 Approved
0.5714 Remote Similarity NPD7319 Approved
0.57 Remote Similarity NPD7154 Phase 3
0.567 Remote Similarity NPD7145 Approved
0.5619 Remote Similarity NPD6698 Approved
0.5619 Remote Similarity NPD46 Approved
0.5612 Remote Similarity NPD6929 Approved
0.561 Remote Similarity NPD2269 Approved
0.56 Remote Similarity NPD6435 Approved

Structure

External Identifiers

PubChem CID   93045
ChEMBL   CHEMBL464889
ZINC  

Physicochemical Properties

Molecular Weight:  364.14
ALogP:  -3.8944
MLogP:  2.01
XLogP:  -2.081
# Rotatable Bonds:  11
Polar Surface Area:  169.3
# H-Bond Aceptor:  10
# H-Bond Donor:  7
# Rings:  3
# Heavy Atoms:  25

Download Data

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Biological Activities  
Similar NPs/Drugs