Natural Product: NPC189575

Natural Product ID:  NPC189575
Common Name:   Ardisianoside B
IUPAC Name:  
Synonyms:   Ardisianoside B
Molecular Formula:   C64H106O31
Standard InCHIKey:  OCSVOVNGBJMZTD-JKDSUZQNSA-N
Standard InCHI:  InChI=1S/C64H106O31/c1-58(2)14-15-63-24-85-64(33(63)16-58)13-9-32-60(5)11-10-35(59(3,4)31(60)8-12-61(32,6)62(64,7)17-34(63)70)91-56-50(94-54-46(81)43(78)38(73)27(19-66)87-54)41(76)30(23-84-56)90-57-51(95-52-44(79)36(71)25(69)22-83-52)49(40(75)29(21-68)89-57)93-55-47(82)48(39(74)28(20-67)88-55)92-53-45(80)42(77)37(72)26(18-65)86-53/h25-57,65-82H,8-24H2,1-7H3/t25-,26-,27-,28-,29-,30+,31+,32-,33-,34-,35+,36+,37-,38-,39-,40-,41+,42+,43+,44-,45-,46-,47-,48+,49+,50-,51-,52+,53+,54+,55+,56+,57+,60+,61-,62+,63-,64+/m1/s1
Canonical SMILES:  OC[C@H]1O[C@@H](O[C@H]2[C@@H](OC[C@@H]([C@@H]2O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O)O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC[C@]34[C@@]2(C)C[C@H]([C@@]2([C@H]4CC(C)(C)CC2)CO3)O)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
NPO3803 Ardisia japonica Species Primulaceae Eukaryota Whole Plants Sendai, Miyagi Prefecture, Japan 2000-SEP PMID[17243725]
NPO3803 Ardisia japonica Species Primulaceae Eukaryota Whole Plants PMID[17243725]
NPO3803 Ardisia japonica Species Primulaceae Eukaryota PMID[22940450]
NPO29575 Ardisiae japonicae herba NA NA NA TCMSP*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT116 Cell Line HL-60 Homo sapiens IC50 = 2400 nM 17243725
NPT81 Cell Line A549 Homo sapiens IC50 = 3100 nM 17243725
NPT2 Others Unspecified Activity < 1 % 22940450
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10000000 nM 22940450
NPT1872 Cell Line Bcap37 Homo sapiens IC50 > 10000000 nM 22940450
NPT393 Cell Line HCT-116 Homo sapiens IC50 > 10000000 nM 22940450
NPT377 Cell Line OVCAR-3 Homo sapiens IC50 > 10000000 nM 22940450
NPT2 Others Unspecified IC50 > 10000000 nM 22940450
NPT397 Cell Line NCI-H460 Homo sapiens IC50 > 10000000 nM 22940450
NPT2 Others Unspecified IC50 > 100000000 nM 22940450
NPT181 Cell Line Bel-7402 Homo sapiens IC50 = 920000 nM 22940450
NPT65 Cell Line HepG2 Homo sapiens IC50 = 2980000 nM 22940450
NPT81 Cell Line A549 Homo sapiens IC50 = 4470000 nM 22940450
NPT1668 Cell Line NCI-H157 Homo sapiens IC50 = 5090000 nM 22940450
NPT515 Cell Line SGC-7901 Homo sapiens IC50 = 5370000 nM 22940450
NPT90 Cell Line DU-145 Homo sapiens IC50 = 6170000 nM 22940450
NPT937 Cell Line NCI-H446 Homo sapiens IC50 = 6630000 nM 22940450
NPT492 Cell Line Caco-2 Homo sapiens IC50 = 7190000 nM 22940450
NPT1097 Cell Line MKN-45 Homo sapiens IC50 = 8390000 nM 22940450
NPT2 Others Unspecified Activity = 10 % 22940450
NPT2 Others Unspecified Activity = 12.5 % 22940450
NPT2 Others Unspecified Activity = 19.1 % 22940450
NPT181 Cell Line Bel-7402 Homo sapiens Activity = 25.5 % 22940450
NPT181 Cell Line Bel-7402 Homo sapiens Activity = 57.8 % 22940450
NPT2 Others Unspecified Activity = 68.4 % 22940450
NPT181 Cell Line Bel-7402 Homo sapiens Activity = 74.5 % 22940450
NPT181 Cell Line Bel-7402 Homo sapiens Activity = 3.9 % 22940450
NPT181 Cell Line Bel-7402 Homo sapiens Activity = 39.4 % 22940450
NPT181 Cell Line Bel-7402 Homo sapiens Activity = 3.2 % 22940450
NPT181 Cell Line Bel-7402 Homo sapiens Activity = 46.4 % 22940450
NPT181 Cell Line Bel-7402 Homo sapiens Activity = 41.5 % 22940450
NPT181 Cell Line Bel-7402 Homo sapiens Activity = 17.6 % 22940450
NPT2 Others Unspecified Activity = 9.2 % 22940450
NPT2 Others Unspecified Activity = 8.3 % 22940450

  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 NPC189575 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 NPC205129
1.0 High Similarity NPC106701
1.0 High Similarity NPC471429
1.0 High Similarity NPC471425
1.0 High Similarity NPC471424
0.9886 High Similarity NPC148593
0.9886 High Similarity NPC471373
0.9886 High Similarity NPC77717
0.9886 High Similarity NPC267238
0.9886 High Similarity NPC253611
0.9773 High Similarity NPC323231
0.9773 High Similarity NPC171741
0.9773 High Similarity NPC470623
0.9773 High Similarity NPC18724
0.9773 High Similarity NPC224003
0.9565 High Similarity NPC471427
0.9565 High Similarity NPC471428
0.9565 High Similarity NPC471426
0.9457 High Similarity NPC209798
0.9457 High Similarity NPC471375
0.9457 High Similarity NPC471374
0.9355 High Similarity NPC51579
0.9022 High Similarity NPC305418
0.8936 High Similarity NPC307534
0.8936 High Similarity NPC476112
0.8925 High Similarity NPC477494
0.8889 High Similarity NPC471626
0.8889 High Similarity NPC262567
0.8889 High Similarity NPC473688
0.8889 High Similarity NPC231566
0.8842 High Similarity NPC473518
0.883 High Similarity NPC470864
0.883 High Similarity NPC103616
0.883 High Similarity NPC184617
0.883 High Similarity NPC116756
0.883 High Similarity NPC284104
0.883 High Similarity NPC470866
0.883 High Similarity NPC470865
0.883 High Similarity NPC470863
0.883 High Similarity NPC128572
0.883 High Similarity NPC160426
0.883 High Similarity NPC132080
0.883 High Similarity NPC98018
0.883 High Similarity NPC304011
0.883 High Similarity NPC139271
0.883 High Similarity NPC97700
0.883 High Similarity NPC475625
0.883 High Similarity NPC30856
0.883 High Similarity NPC287483
0.883 High Similarity NPC84111
0.883 High Similarity NPC232037
0.883 High Similarity NPC475643
0.8804 High Similarity NPC229801
0.8804 High Similarity NPC307167
0.8804 High Similarity NPC210759
0.88 High Similarity NPC22709
0.8791 High Similarity NPC131466
0.8788 High Similarity NPC126753
0.8788 High Similarity NPC471430
0.8788 High Similarity NPC475630
0.8788 High Similarity NPC40716
0.8788 High Similarity NPC475234
0.8788 High Similarity NPC138219
0.8737 High Similarity NPC115165
0.8737 High Similarity NPC83137
0.8737 High Similarity NPC232611
0.8737 High Similarity NPC470862
0.8737 High Similarity NPC303069
0.8737 High Similarity NPC470861
0.8737 High Similarity NPC51520
0.8737 High Similarity NPC274200
0.8723 High Similarity NPC211354
0.8723 High Similarity NPC473727
0.8723 High Similarity NPC107962
0.8723 High Similarity NPC19400
0.8723 High Similarity NPC475351
0.8723 High Similarity NPC206003
0.8723 High Similarity NPC6295
0.8723 High Similarity NPC107188
0.8723 High Similarity NPC473610
0.8713 High Similarity NPC471431
0.871 High Similarity NPC172838
0.871 High Similarity NPC137004
0.87 High Similarity NPC207693
0.8687 High Similarity NPC158367
0.8687 High Similarity NPC158051
0.8687 High Similarity NPC119628
0.8687 High Similarity NPC184805
0.8687 High Similarity NPC273189
0.8646 High Similarity NPC291548
0.8632 High Similarity NPC473601
0.8632 High Similarity NPC121453
0.8632 High Similarity NPC195297
0.8617 High Similarity NPC291203
0.8617 High Similarity NPC131693
0.8617 High Similarity NPC473851
0.8617 High Similarity NPC45959
0.8617 High Similarity NPC264101
0.8617 High Similarity NPC475436
0.8617 High Similarity NPC471464
0.8617 High Similarity NPC253268
0.8617 High Similarity NPC217205
0.8617 High Similarity NPC174024
0.8617 High Similarity NPC291547
0.8617 High Similarity NPC252253
0.8617 High Similarity NPC312678
0.8617 High Similarity NPC179859
0.8587 High Similarity NPC82955
0.8586 High Similarity NPC267637
0.8571 High Similarity NPC43912
0.8571 High Similarity NPC140446
0.8542 High Similarity NPC477223
0.8542 High Similarity NPC477222
0.8526 High Similarity NPC474399
0.8511 High Similarity NPC249204
0.8511 High Similarity NPC477547
0.8511 High Similarity NPC141769
0.8511 High Similarity NPC234352
0.8511 High Similarity NPC88962
0.8511 High Similarity NPC144790
0.8511 High Similarity NPC477451
0.8511 High Similarity NPC48339
0.8511 High Similarity NPC297348
0.8511 High Similarity NPC250393
0.8511 High Similarity NPC177834
0.8511 High Similarity NPC325828
0.8511 High Similarity NPC149400
0.8495 Intermediate Similarity NPC65550
0.8438 Intermediate Similarity NPC238796
0.8438 Intermediate Similarity NPC203434
0.8438 Intermediate Similarity NPC142264
0.8438 Intermediate Similarity NPC476510
0.8438 Intermediate Similarity NPC237071
0.8421 Intermediate Similarity NPC294686
0.8421 Intermediate Similarity NPC24960
0.8421 Intermediate Similarity NPC473774
0.8421 Intermediate Similarity NPC309866
0.8421 Intermediate Similarity NPC222731
0.8404 Intermediate Similarity NPC204881
0.8404 Intermediate Similarity NPC473830
0.8384 Intermediate Similarity NPC80640
0.8381 Intermediate Similarity NPC477465
0.8365 Intermediate Similarity NPC157571
0.8352 Intermediate Similarity NPC290612
0.8351 Intermediate Similarity NPC233649
0.8351 Intermediate Similarity NPC470591
0.8351 Intermediate Similarity NPC470028
0.835 Intermediate Similarity NPC470622
0.835 Intermediate Similarity NPC66513
0.8333 Intermediate Similarity NPC92196
0.8333 Intermediate Similarity NPC241959
0.8333 Intermediate Similarity NPC94582
0.8333 Intermediate Similarity NPC57964
0.8316 Intermediate Similarity NPC473726
0.8316 Intermediate Similarity NPC311246
0.8316 Intermediate Similarity NPC167644
0.8298 Intermediate Similarity NPC473542
0.8298 Intermediate Similarity NPC279329
0.8283 Intermediate Similarity NPC475574
0.828 Intermediate Similarity NPC281004
0.8261 Intermediate Similarity NPC471411
0.8261 Intermediate Similarity NPC471410
0.8252 Intermediate Similarity NPC87393
0.8229 Intermediate Similarity NPC3538
0.8229 Intermediate Similarity NPC477224
0.8229 Intermediate Similarity NPC175
0.8229 Intermediate Similarity NPC113500
0.8218 Intermediate Similarity NPC476360
0.8218 Intermediate Similarity NPC476361
0.8211 Intermediate Similarity NPC5632
0.8211 Intermediate Similarity NPC36372
0.8211 Intermediate Similarity NPC293609
0.8211 Intermediate Similarity NPC149966
0.8191 Intermediate Similarity NPC473472
0.8191 Intermediate Similarity NPC102725
0.819 Intermediate Similarity NPC476305
0.8182 Intermediate Similarity NPC80417
0.8182 Intermediate Similarity NPC272841
0.8182 Intermediate Similarity NPC177343
0.8182 Intermediate Similarity NPC477577
0.8163 Intermediate Similarity NPC475207
0.8163 Intermediate Similarity NPC210157
0.8155 Intermediate Similarity NPC6931
0.8155 Intermediate Similarity NPC159005
0.8144 Intermediate Similarity NPC473065
0.8144 Intermediate Similarity NPC473064
0.8144 Intermediate Similarity NPC473067
0.8137 Intermediate Similarity NPC173859
0.8137 Intermediate Similarity NPC470512
0.8125 Intermediate Similarity NPC277774
0.8119 Intermediate Similarity NPC123796
0.8105 Intermediate Similarity NPC223143
0.81 Intermediate Similarity NPC108227
0.81 Intermediate Similarity NPC476839
0.81 Intermediate Similarity NPC476512
0.81 Intermediate Similarity NPC476838
0.81 Intermediate Similarity NPC472081
0.8095 Intermediate Similarity NPC157474
0.8095 Intermediate Similarity NPC110494
0.8081 Intermediate Similarity NPC473638

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC189575 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
0.8511 High Similarity NPD8171 Discontinued
0.7692 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD8133 Approved
0.7234 Intermediate Similarity NPD6928 Phase 2
0.7143 Intermediate Similarity NPD1811 Approved
0.7143 Intermediate Similarity NPD1810 Approved
0.6923 Remote Similarity NPD8377 Approved
0.6923 Remote Similarity NPD8294 Approved
0.6864 Remote Similarity NPD8378 Approved
0.6864 Remote Similarity NPD8380 Approved
0.6864 Remote Similarity NPD8296 Approved
0.6864 Remote Similarity NPD8379 Approved
0.6864 Remote Similarity NPD8335 Approved
0.6813 Remote Similarity NPD2686 Approved
0.6813 Remote Similarity NPD2254 Approved
0.6813 Remote Similarity NPD2687 Approved
0.681 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6786 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6723 Remote Similarity NPD8033 Approved
0.6703 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3669 Approved
0.663 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6612 Remote Similarity NPD8328 Phase 3
0.661 Remote Similarity NPD7328 Approved
0.661 Remote Similarity NPD7327 Approved
0.6555 Remote Similarity NPD7516 Approved
0.6449 Remote Similarity NPD7991 Discontinued
0.6364 Remote Similarity NPD6123 Approved
0.6333 Remote Similarity NPD371 Approved
0.6179 Remote Similarity NPD7503 Approved
0.6174 Remote Similarity NPD6412 Phase 2
0.6167 Remote Similarity NPD6940 Discontinued
0.6154 Remote Similarity NPD8450 Suspended
0.6121 Remote Similarity NPD8174 Phase 2
0.6111 Remote Similarity NPD7507 Approved
0.6077 Remote Similarity NPD8449 Approved
0.6048 Remote Similarity NPD8515 Approved
0.6048 Remote Similarity NPD8517 Approved
0.6048 Remote Similarity NPD8516 Approved
0.6 Remote Similarity NPD6115 Approved
0.6 Remote Similarity NPD6118 Approved
0.6 Remote Similarity NPD6697 Approved
0.6 Remote Similarity NPD6114 Approved
0.5983 Remote Similarity NPD6686 Approved
0.598 Remote Similarity NPD1779 Approved
0.598 Remote Similarity NPD1780 Approved
0.5969 Remote Similarity NPD7319 Approved
0.5941 Remote Similarity NPD7645 Phase 2
0.592 Remote Similarity NPD8513 Phase 3
0.59 Remote Similarity NPD6116 Phase 1
0.5891 Remote Similarity NPD7736 Approved
0.5847 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5833 Remote Similarity NPD8413 Clinical (unspecified phase)
0.58 Remote Similarity NPD6117 Approved
0.5773 Remote Similarity NPD4787 Phase 1
0.5748 Remote Similarity NPD6370 Approved
0.5728 Remote Similarity NPD7525 Registered
0.5727 Remote Similarity NPD8035 Phase 2
0.5727 Remote Similarity NPD8034 Phase 2
0.57 Remote Similarity NPD3703 Phase 2
0.5692 Remote Similarity NPD8293 Discontinued
0.5682 Remote Similarity NPD7346 Approved
0.5667 Remote Similarity NPD4061 Clinical (unspecified phase)
0.56 Remote Similarity NPD6113 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   16109773
ChEMBL   CHEMBL374092
ZINC  

Physicochemical Properties

Molecular Weight:  1370.67
ALogP:  -7.8177
MLogP:  5.09
XLogP:  -0.718
# Rotatable Bonds:  41
Polar Surface Area:  484.13
# H-Bond Aceptor:  31
# H-Bond Donor:  18
# Rings:  12
# Heavy Atoms:  95

Download Data

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Biological Activities  
Similar NPs/Drugs