Natural Product: NPC154815

Natural Product ID:  NPC154815
Common Name:   Hellebrigenol-3-O-Sulfite
IUPAC Name:   [(3S,5S,8R,9S,10R,13R,14S,17R)-5,14-dihydroxy-10-(hydroxymethyl)-13-methyl-17-(6-oxopyran-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
Synonyms:  
Molecular Formula:   C24H34O9S
Standard InCHIKey:  MGPQGNBMLAFGGK-XHCIOXAKSA-N
Standard InCHI:  InChI=1S/C24H34O9S/c1-21-8-5-18-19(24(21,28)11-7-17(21)15-2-3-20(26)32-13-15)6-10-23(27)12-16(33-34(29,30)31)4-9-22(18,23)14-25/h2-3,13,16-19,25,27-28H,4-12,14H2,1H3,(H,29,30,31)/t16-,17+,18-,19+,21+,22-,23-,24-/m0/s1
Canonical SMILES:  OC[C@@]12CC[C@@H](C[C@@]2(O)CC[C@@H]2[C@@H]1CC[C@]1([C@]2(O)CC[C@@H]1c1ccc(=O)oc1)C)OS(=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
NPO32597 bufo melanosticus Species Bufonidae Eukaryota PMID[20361780]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified IC50 = 323 nM 22328583
NPT83 Cell Line MCF7 Homo sapiens IC50 = 120 nM 21051535
NPT3723 Cell Line CT26 Mus musculus IC50 > 10000 nM 17582659
NPT169 Cell Line B16-F10 Mus musculus IC50 > 10000 nM 18364258
NPT81 Cell Line A549 Homo sapiens IC50 = 80 nM 23684893
NPT2 Others Unspecified IC50 = 50 nM 18183025

  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 NPC154815 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
0.9904 High Similarity NPC247760
0.9808 High Similarity NPC183603
0.9519 High Similarity NPC304276
0.9519 High Similarity NPC137462
0.9439 High Similarity NPC241977
0.934 High Similarity NPC12795
0.9167 High Similarity NPC44537
0.9135 High Similarity NPC171014
0.9083 High Similarity NPC171126
0.8981 High Similarity NPC103491
0.8972 High Similarity NPC275060
0.8962 High Similarity NPC295843
0.8957 High Similarity NPC233041
0.8889 High Similarity NPC75389
0.8879 High Similarity NPC79298
0.8879 High Similarity NPC43063
0.8772 High Similarity NPC145074
0.8772 High Similarity NPC257610
0.8772 High Similarity NPC114939
0.8772 High Similarity NPC41123
0.8761 High Similarity NPC146786
0.8684 High Similarity NPC213761
0.8684 High Similarity NPC35171
0.8609 High Similarity NPC184555
0.8609 High Similarity NPC112936
0.8596 High Similarity NPC16701
0.8547 High Similarity NPC55602
0.8522 High Similarity NPC278681
0.8509 High Similarity NPC185287
0.8509 High Similarity NPC157380
0.8468 Intermediate Similarity NPC16270
0.8426 Intermediate Similarity NPC97487
0.8426 Intermediate Similarity NPC189588
0.8426 Intermediate Similarity NPC10232
0.8426 Intermediate Similarity NPC196471
0.8426 Intermediate Similarity NPC187302
0.8407 Intermediate Similarity NPC73050
0.8349 Intermediate Similarity NPC165969
0.8273 Intermediate Similarity NPC189863
0.8241 Intermediate Similarity NPC295110
0.8241 Intermediate Similarity NPC25177
0.8241 Intermediate Similarity NPC268829
0.8241 Intermediate Similarity NPC247701
0.8241 Intermediate Similarity NPC222875
0.8224 Intermediate Similarity NPC278673
0.822 Intermediate Similarity NPC312481
0.8214 Intermediate Similarity NPC475030
0.8108 Intermediate Similarity NPC220217
0.8108 Intermediate Similarity NPC119855
0.8108 Intermediate Similarity NPC266570
0.8091 Intermediate Similarity NPC160583
0.8083 Intermediate Similarity NPC6193
0.8056 Intermediate Similarity NPC218107
0.8049 Intermediate Similarity NPC221414
0.8018 Intermediate Similarity NPC472822
0.7982 Intermediate Similarity NPC238850
0.7963 Intermediate Similarity NPC99726
0.7963 Intermediate Similarity NPC51499
0.7951 Intermediate Similarity NPC179261
0.7946 Intermediate Similarity NPC186668
0.7937 Intermediate Similarity NPC248703
0.7928 Intermediate Similarity NPC45897
0.7928 Intermediate Similarity NPC297617
0.7928 Intermediate Similarity NPC472821
0.7917 Intermediate Similarity NPC233500
0.7913 Intermediate Similarity NPC284162
0.7913 Intermediate Similarity NPC255401
0.789 Intermediate Similarity NPC275086
0.789 Intermediate Similarity NPC325229
0.7881 Intermediate Similarity NPC471353
0.7881 Intermediate Similarity NPC471355
0.7881 Intermediate Similarity NPC474418
0.7881 Intermediate Similarity NPC99728
0.7881 Intermediate Similarity NPC471354
0.7881 Intermediate Similarity NPC50305
0.7881 Intermediate Similarity NPC157376
0.7881 Intermediate Similarity NPC27507
0.7881 Intermediate Similarity NPC84987
0.7881 Intermediate Similarity NPC471351
0.7881 Intermediate Similarity NPC158344
0.7881 Intermediate Similarity NPC87250
0.7881 Intermediate Similarity NPC77319
0.7881 Intermediate Similarity NPC244402
0.7881 Intermediate Similarity NPC309034
0.7881 Intermediate Similarity NPC473852
0.7881 Intermediate Similarity NPC196429
0.7881 Intermediate Similarity NPC142066
0.7881 Intermediate Similarity NPC34390
0.7881 Intermediate Similarity NPC243196
0.787 Intermediate Similarity NPC16967
0.787 Intermediate Similarity NPC299654
0.7857 Intermediate Similarity NPC200861
0.7851 Intermediate Similarity NPC196130
0.785 Intermediate Similarity NPC201725
0.785 Intermediate Similarity NPC191521
0.7818 Intermediate Similarity NPC251680
0.7815 Intermediate Similarity NPC83287
0.7812 Intermediate Similarity NPC62172
0.7812 Intermediate Similarity NPC289700
0.781 Intermediate Similarity NPC74258
0.7805 Intermediate Similarity NPC159499
0.7798 Intermediate Similarity NPC477226
0.7798 Intermediate Similarity NPC231751
0.7797 Intermediate Similarity NPC5311
0.7797 Intermediate Similarity NPC193382
0.7797 Intermediate Similarity NPC199428
0.7797 Intermediate Similarity NPC310341
0.7797 Intermediate Similarity NPC99620
0.7788 Intermediate Similarity NPC471206
0.7788 Intermediate Similarity NPC472818
0.7788 Intermediate Similarity NPC34768
0.7778 Intermediate Similarity NPC276110
0.7768 Intermediate Similarity NPC85742
0.7768 Intermediate Similarity NPC112009
0.7759 Intermediate Similarity NPC470076
0.7759 Intermediate Similarity NPC262083
0.7759 Intermediate Similarity NPC471484
0.775 Intermediate Similarity NPC219656
0.7731 Intermediate Similarity NPC93883
0.7731 Intermediate Similarity NPC152615
0.7727 Intermediate Similarity NPC57079
0.7727 Intermediate Similarity NPC92275
0.7727 Intermediate Similarity NPC108368
0.7727 Intermediate Similarity NPC181147
0.7719 Intermediate Similarity NPC475074
0.7719 Intermediate Similarity NPC179380
0.7719 Intermediate Similarity NPC475781
0.7719 Intermediate Similarity NPC472820
0.7712 Intermediate Similarity NPC84949
0.7712 Intermediate Similarity NPC31354
0.7712 Intermediate Similarity NPC69576
0.7712 Intermediate Similarity NPC471633
0.7706 Intermediate Similarity NPC190713
0.7699 Intermediate Similarity NPC472819
0.7692 Intermediate Similarity NPC475354
0.7692 Intermediate Similarity NPC75616
0.7686 Intermediate Similarity NPC475629
0.7686 Intermediate Similarity NPC475136
0.7686 Intermediate Similarity NPC475556
0.7686 Intermediate Similarity NPC474466
0.7685 Intermediate Similarity NPC279410
0.7685 Intermediate Similarity NPC119562
0.7672 Intermediate Similarity NPC177047
0.7664 Intermediate Similarity NPC130840
0.7652 Intermediate Similarity NPC50124
0.7652 Intermediate Similarity NPC472825
0.7647 Intermediate Similarity NPC232564
0.7647 Intermediate Similarity NPC469794
0.7647 Intermediate Similarity NPC72772
0.7647 Intermediate Similarity NPC470075
0.7647 Intermediate Similarity NPC113425
0.7642 Intermediate Similarity NPC219804
0.7638 Intermediate Similarity NPC155529
0.7632 Intermediate Similarity NPC218158
0.7623 Intermediate Similarity NPC173555
0.7623 Intermediate Similarity NPC314535
0.7611 Intermediate Similarity NPC473523
0.7611 Intermediate Similarity NPC180204
0.7607 Intermediate Similarity NPC474315
0.7603 Intermediate Similarity NPC329905
0.7603 Intermediate Similarity NPC469756
0.7603 Intermediate Similarity NPC304260
0.7603 Intermediate Similarity NPC5883
0.7603 Intermediate Similarity NPC292467
0.7603 Intermediate Similarity NPC55532
0.7603 Intermediate Similarity NPC236973
0.7603 Intermediate Similarity NPC470897
0.7603 Intermediate Similarity NPC30483
0.7603 Intermediate Similarity NPC29639
0.7603 Intermediate Similarity NPC44899
0.7603 Intermediate Similarity NPC32177
0.7593 Intermediate Similarity NPC476304
0.7593 Intermediate Similarity NPC205034
0.7593 Intermediate Similarity NPC152778
0.7593 Intermediate Similarity NPC162615
0.7593 Intermediate Similarity NPC214697
0.7589 Intermediate Similarity NPC168319
0.7589 Intermediate Similarity NPC194028
0.7589 Intermediate Similarity NPC11974
0.7583 Intermediate Similarity NPC203862
0.7583 Intermediate Similarity NPC290693
0.757 Intermediate Similarity NPC302280
0.7565 Intermediate Similarity NPC471205
0.7565 Intermediate Similarity NPC302788
0.7565 Intermediate Similarity NPC64844
0.7565 Intermediate Similarity NPC263729
0.7565 Intermediate Similarity NPC42847
0.7563 Intermediate Similarity NPC216665
0.7561 Intermediate Similarity NPC471082
0.7561 Intermediate Similarity NPC264336
0.7545 Intermediate Similarity NPC471903
0.7545 Intermediate Similarity NPC253115
0.7545 Intermediate Similarity NPC195366
0.7545 Intermediate Similarity NPC304899
0.7545 Intermediate Similarity NPC114743
0.7544 Intermediate Similarity NPC272632
0.7544 Intermediate Similarity NPC473543
0.7541 Intermediate Similarity NPC72260
0.7541 Intermediate Similarity NPC135369
0.7541 Intermediate Similarity NPC476962

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC154815 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
0.822 Intermediate Similarity NPD7503 Approved
0.789 Intermediate Similarity NPD7638 Approved
0.7818 Intermediate Similarity NPD7640 Approved
0.7818 Intermediate Similarity NPD7639 Approved
0.7815 Intermediate Similarity NPD7327 Approved
0.7815 Intermediate Similarity NPD7328 Approved
0.775 Intermediate Similarity NPD7516 Approved
0.7623 Intermediate Similarity NPD8380 Approved
0.7623 Intermediate Similarity NPD8335 Approved
0.7623 Intermediate Similarity NPD8379 Approved
0.7623 Intermediate Similarity NPD8378 Approved
0.7623 Intermediate Similarity NPD8296 Approved
0.7541 Intermediate Similarity NPD8377 Approved
0.7541 Intermediate Similarity NPD8294 Approved
0.748 Intermediate Similarity NPD8033 Approved
0.7295 Intermediate Similarity NPD7115 Discovery
0.7244 Intermediate Similarity NPD7507 Approved
0.7217 Intermediate Similarity NPD7632 Discontinued
0.7209 Intermediate Similarity NPD7319 Approved
0.7203 Intermediate Similarity NPD6881 Approved
0.7203 Intermediate Similarity NPD6899 Approved
0.7167 Intermediate Similarity NPD6649 Approved
0.7167 Intermediate Similarity NPD6650 Approved
0.7119 Intermediate Similarity NPD5697 Approved
0.7107 Intermediate Similarity NPD8297 Approved
0.7107 Intermediate Similarity NPD6882 Approved
0.7083 Intermediate Similarity NPD7102 Approved
0.7083 Intermediate Similarity NPD7290 Approved
0.7083 Intermediate Similarity NPD6883 Approved
0.7034 Intermediate Similarity NPD6402 Approved
0.7034 Intermediate Similarity NPD7128 Approved
0.7034 Intermediate Similarity NPD5739 Approved
0.7034 Intermediate Similarity NPD6675 Approved
0.7027 Intermediate Similarity NPD7637 Suspended
0.7025 Intermediate Similarity NPD6847 Approved
0.7025 Intermediate Similarity NPD8130 Phase 1
0.7025 Intermediate Similarity NPD6617 Approved
0.7025 Intermediate Similarity NPD6869 Approved
0.7 Intermediate Similarity NPD6014 Approved
0.7 Intermediate Similarity NPD6051 Approved
0.7 Intermediate Similarity NPD6013 Approved
0.7 Intermediate Similarity NPD6372 Approved
0.7 Intermediate Similarity NPD6012 Approved
0.7 Intermediate Similarity NPD6373 Approved
0.6967 Remote Similarity NPD6053 Discontinued
0.6952 Remote Similarity NPD7525 Registered
0.6923 Remote Similarity NPD5211 Phase 2
0.6917 Remote Similarity NPD6011 Approved
0.6917 Remote Similarity NPD7320 Approved
0.6916 Remote Similarity NPD6695 Phase 3
0.6911 Remote Similarity NPD4632 Approved
0.6897 Remote Similarity NPD5286 Approved
0.6897 Remote Similarity NPD5285 Approved
0.6897 Remote Similarity NPD4696 Approved
0.687 Remote Similarity NPD6083 Phase 2
0.687 Remote Similarity NPD6084 Phase 2
0.6852 Remote Similarity NPD7338 Clinical (unspecified phase)
0.685 Remote Similarity NPD6319 Approved
0.6833 Remote Similarity NPD5701 Approved
0.681 Remote Similarity NPD4225 Approved
0.6807 Remote Similarity NPD5141 Approved
0.6792 Remote Similarity NPD6930 Phase 2
0.6792 Remote Similarity NPD6931 Approved
0.6792 Remote Similarity NPD7514 Phase 3
0.678 Remote Similarity NPD5224 Approved
0.678 Remote Similarity NPD5226 Approved
0.678 Remote Similarity NPD4633 Approved
0.678 Remote Similarity NPD5225 Approved
0.6752 Remote Similarity NPD6648 Approved
0.6748 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6746 Remote Similarity NPD6009 Approved
0.6742 Remote Similarity NPD7736 Approved
0.6726 Remote Similarity NPD6079 Approved
0.6726 Remote Similarity NPD7515 Phase 2
0.6724 Remote Similarity NPD4755 Approved
0.6723 Remote Similarity NPD5174 Approved
0.6723 Remote Similarity NPD5175 Approved
0.6698 Remote Similarity NPD6929 Approved
0.6698 Remote Similarity NPD4195 Approved
0.6695 Remote Similarity NPD5223 Approved
0.6695 Remote Similarity NPD5344 Discontinued
0.6667 Remote Similarity NPD4202 Approved
0.6667 Remote Similarity NPD4634 Approved
0.6667 Remote Similarity NPD7524 Approved
0.6667 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7750 Discontinued
0.6667 Remote Similarity NPD6932 Approved
0.6641 Remote Similarity NPD7101 Approved
0.6641 Remote Similarity NPD7100 Approved
0.6641 Remote Similarity NPD7492 Approved
0.6639 Remote Similarity NPD6686 Approved
0.6639 Remote Similarity NPD4729 Approved
0.6639 Remote Similarity NPD4730 Approved
0.6636 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6636 Remote Similarity NPD7332 Phase 2
0.6614 Remote Similarity NPD6317 Approved
0.661 Remote Similarity NPD4700 Approved
0.6609 Remote Similarity NPD7748 Approved
0.6607 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6604 Remote Similarity NPD7145 Approved
0.6591 Remote Similarity NPD6616 Approved
0.6589 Remote Similarity NPD6054 Approved
0.6585 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6579 Remote Similarity NPD5281 Approved
0.6579 Remote Similarity NPD5284 Approved
0.6574 Remote Similarity NPD6902 Approved
0.6565 Remote Similarity NPD7604 Phase 2
0.6562 Remote Similarity NPD6335 Approved
0.6552 Remote Similarity NPD5210 Approved
0.6552 Remote Similarity NPD5695 Phase 3
0.6552 Remote Similarity NPD4629 Approved
0.6549 Remote Similarity NPD5328 Approved
0.6549 Remote Similarity NPD4753 Phase 2
0.6542 Remote Similarity NPD7645 Phase 2
0.6541 Remote Similarity NPD7078 Approved
0.6538 Remote Similarity NPD5983 Phase 2
0.6535 Remote Similarity NPD6274 Approved
0.6532 Remote Similarity NPD5248 Approved
0.6532 Remote Similarity NPD5251 Approved
0.6532 Remote Similarity NPD5247 Approved
0.6532 Remote Similarity NPD5249 Phase 3
0.6532 Remote Similarity NPD5250 Approved
0.6532 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6525 Remote Similarity NPD5696 Approved
0.6509 Remote Similarity NPD6925 Approved
0.6509 Remote Similarity NPD5776 Phase 2
0.6508 Remote Similarity NPD8133 Approved
0.6496 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6496 Remote Similarity NPD5222 Approved
0.6496 Remote Similarity NPD5221 Approved
0.6489 Remote Similarity NPD6370 Approved
0.6486 Remote Similarity NPD6893 Approved
0.6475 Remote Similarity NPD4767 Approved
0.6475 Remote Similarity NPD6008 Approved
0.6475 Remote Similarity NPD4768 Approved
0.6466 Remote Similarity NPD6336 Discontinued
0.6455 Remote Similarity NPD4788 Approved
0.6446 Remote Similarity NPD4754 Approved
0.6441 Remote Similarity NPD5173 Approved
0.6441 Remote Similarity NPD7902 Approved
0.6435 Remote Similarity NPD7087 Discontinued
0.6435 Remote Similarity NPD8034 Phase 2
0.6435 Remote Similarity NPD8035 Phase 2
0.6435 Remote Similarity NPD5693 Phase 1
0.6434 Remote Similarity NPD6314 Approved
0.6434 Remote Similarity NPD6313 Approved
0.6429 Remote Similarity NPD6684 Approved
0.6429 Remote Similarity NPD6409 Approved
0.6429 Remote Similarity NPD3618 Phase 1
0.6429 Remote Similarity NPD7521 Approved
0.6429 Remote Similarity NPD5330 Approved
0.6429 Remote Similarity NPD7334 Approved
0.6429 Remote Similarity NPD7146 Approved
0.6423 Remote Similarity NPD6412 Phase 2
0.6415 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6412 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6412 Remote Similarity NPD6015 Approved
0.6412 Remote Similarity NPD6016 Approved
0.641 Remote Similarity NPD6356 Clinical (unspecified phase)
0.64 Remote Similarity NPD5135 Approved
0.64 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6396 Remote Similarity NPD3666 Approved
0.6396 Remote Similarity NPD3133 Approved
0.6396 Remote Similarity NPD3665 Phase 1
0.6389 Remote Similarity NPD6683 Phase 2
0.6381 Remote Similarity NPD6926 Approved
0.6381 Remote Similarity NPD6924 Approved
0.6379 Remote Similarity NPD6399 Phase 3
0.6371 Remote Similarity NPD5128 Approved
0.6364 Remote Similarity NPD5988 Approved
0.6349 Remote Similarity NPD5216 Approved
0.6349 Remote Similarity NPD5217 Approved
0.6349 Remote Similarity NPD5215 Approved
0.6348 Remote Similarity NPD7838 Discovery
0.6348 Remote Similarity NPD5785 Approved
0.6336 Remote Similarity NPD6059 Approved
0.6327 Remote Similarity NPD7236 Approved
0.6321 Remote Similarity NPD6942 Approved
0.6321 Remote Similarity NPD7339 Approved
0.6316 Remote Similarity NPD6903 Approved
0.6301 Remote Similarity NPD7625 Phase 1
0.6296 Remote Similarity NPD8293 Discontinued
0.6293 Remote Similarity NPD6050 Approved
0.6293 Remote Similarity NPD5694 Approved
0.629 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6288 Remote Similarity NPD6909 Approved
0.6288 Remote Similarity NPD6908 Approved
0.6281 Remote Similarity NPD4159 Approved
0.6279 Remote Similarity NPD6868 Approved
0.6273 Remote Similarity NPD6898 Phase 1
0.627 Remote Similarity NPD5169 Approved
0.6262 Remote Similarity NPD6933 Approved
0.6261 Remote Similarity NPD6673 Approved
0.6261 Remote Similarity NPD6080 Approved
0.6261 Remote Similarity NPD6904 Approved
0.625 Remote Similarity NPD4786 Approved
0.625 Remote Similarity NPD3668 Phase 3
0.625 Remote Similarity NPD5290 Discontinued
0.6226 Remote Similarity NPD4784 Approved
0.6226 Remote Similarity NPD4785 Approved

Structure

External Identifiers

PubChem CID   46210588
ChEMBL   CHEMBL1097253
ZINC  

Physicochemical Properties

Molecular Weight:  498.19
ALogP:  -1.6759
MLogP:  3
XLogP:  0.582
# Rotatable Bonds:  9
Polar Surface Area:  158.97
# H-Bond Aceptor:  9
# H-Bond Donor:  4
# Rings:  5
# Heavy Atoms:  34

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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