Natural Product: NPC44537

Natural Product ID:  NPC44537
Common Name:   5Beta-Hydroxybufotalin
IUPAC Name:   [(3S,5S,8R,9S,10R,13R,14S,16S,17R)-3,5,14-trihydroxy-10,13-dimethyl-17-(6-oxopyran-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl] acetate
Synonyms:   5Beta-Hydroxybufotalin
Molecular Formula:   C26H36O7
Standard InCHIKey:  XXFFZCKSFHQEMN-JPDWBOAPSA-N
Standard InCHI:  InChI=1S/C26H36O7/c1-15(27)33-20-13-26(31)19-8-11-25(30)12-17(28)6-9-23(25,2)18(19)7-10-24(26,3)22(20)16-4-5-21(29)32-14-16/h4-5,14,17-20,22,28,30-31H,6-13H2,1-3H3/t17-,18-,19+,20-,22-,23+,24+,25-,26-/m0/s1
Canonical SMILES:  O[C@H]1CC[C@]2([C@](C1)(O)CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)C[C@@H]([C@@H]2c1ccc(=O)oc1)OC(=O)C)C)C
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
NPO11981 Bufo gargarizans Species Bufonidae Eukaryota TCMID*
NPO8733 Duttaphrynus melanostictus Species Bufonidae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT91 Cell Line KB Homo sapiens IC50 = 0.2 ug/ml 11575946
NPT116 Cell Line HL-60 Homo sapiens IC50 < 0.01 ug/ml 11575946
NPT1366 Cell Line MH60 Mus musculus IC50 > 25 ug/ml 11575946
NPT1081 Cell Line BXPC-3 Homo sapiens IC50 = 0.11 ug/ml 11575946
NPT83 Cell Line MCF7 Homo sapiens IC50 = 0.046 ug/ml 11575946
NPT395 Cell Line SF-268 Homo sapiens IC50 = 0.033 ug/ml 11575946
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 0.048 ug/ml 11575946
NPT575 Cell Line KM-20L2 Homo sapiens IC50 = 0.034 ug/ml 11575946
NPT90 Cell Line DU-145 Homo sapiens IC50 = 0.024 ug/ml 11575946

  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 NPC44537 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
0.9709 High Similarity NPC75389
0.9615 High Similarity NPC12795
0.9612 High Similarity NPC275060
0.9612 High Similarity NPC304276
0.9612 High Similarity NPC137462
0.9528 High Similarity NPC171126
0.945 High Similarity NPC35171
0.945 High Similarity NPC213761
0.9364 High Similarity NPC112936
0.9358 High Similarity NPC16701
0.9273 High Similarity NPC278681
0.9266 High Similarity NPC157380
0.9266 High Similarity NPC185287
0.9245 High Similarity NPC103491
0.9231 High Similarity NPC295843
0.9223 High Similarity NPC171014
0.9167 High Similarity NPC241977
0.9167 High Similarity NPC154815
0.9143 High Similarity NPC43063
0.9143 High Similarity NPC79298
0.9074 High Similarity NPC247760
0.9018 High Similarity NPC41123
0.9018 High Similarity NPC257610
0.9018 High Similarity NPC145074
0.9018 High Similarity NPC114939
0.8981 High Similarity NPC183603
0.8868 High Similarity NPC220217
0.8868 High Similarity NPC119855
0.8839 High Similarity NPC146786
0.8772 High Similarity NPC312481
0.8716 High Similarity NPC16270
0.8684 High Similarity NPC184555
0.8679 High Similarity NPC97487
0.8679 High Similarity NPC196471
0.8679 High Similarity NPC189588
0.8679 High Similarity NPC10232
0.8679 High Similarity NPC187302
0.8654 High Similarity NPC278673
0.8641 High Similarity NPC299654
0.8621 High Similarity NPC6193
0.8621 High Similarity NPC55602
0.8598 High Similarity NPC165969
0.8571 High Similarity NPC221414
0.8505 High Similarity NPC160583
0.8491 Intermediate Similarity NPC247701
0.8491 Intermediate Similarity NPC268829
0.8491 Intermediate Similarity NPC25177
0.8491 Intermediate Similarity NPC295110
0.8491 Intermediate Similarity NPC222875
0.8482 Intermediate Similarity NPC73050
0.8475 Intermediate Similarity NPC159499
0.8468 Intermediate Similarity NPC284162
0.8468 Intermediate Similarity NPC255401
0.8455 Intermediate Similarity NPC475030
0.8448 Intermediate Similarity NPC233500
0.8378 Intermediate Similarity NPC238850
0.8376 Intermediate Similarity NPC196130
0.8365 Intermediate Similarity NPC276110
0.8349 Intermediate Similarity NPC189863
0.8349 Intermediate Similarity NPC266570
0.8333 Intermediate Similarity NPC45897
0.8333 Intermediate Similarity NPC297617
0.8333 Intermediate Similarity NPC472821
0.8304 Intermediate Similarity NPC470076
0.8304 Intermediate Similarity NPC262083
0.8304 Intermediate Similarity NPC471484
0.8302 Intermediate Similarity NPC218107
0.8286 Intermediate Similarity NPC16967
0.8276 Intermediate Similarity NPC219656
0.8273 Intermediate Similarity NPC475781
0.8269 Intermediate Similarity NPC3359
0.8257 Intermediate Similarity NPC472822
0.8235 Intermediate Similarity NPC233041
0.8208 Intermediate Similarity NPC99726
0.8208 Intermediate Similarity NPC51499
0.8182 Intermediate Similarity NPC34768
0.8182 Intermediate Similarity NPC471206
0.8182 Intermediate Similarity NPC186668
0.8175 Intermediate Similarity NPC75616
0.8174 Intermediate Similarity NPC113425
0.8174 Intermediate Similarity NPC232564
0.8167 Intermediate Similarity NPC179261
0.8151 Intermediate Similarity NPC219804
0.8145 Intermediate Similarity NPC248703
0.8131 Intermediate Similarity NPC325229
0.8131 Intermediate Similarity NPC275086
0.812 Intermediate Similarity NPC29639
0.812 Intermediate Similarity NPC270850
0.812 Intermediate Similarity NPC44899
0.812 Intermediate Similarity NPC304260
0.812 Intermediate Similarity NPC305260
0.812 Intermediate Similarity NPC5883
0.8113 Intermediate Similarity NPC304899
0.8113 Intermediate Similarity NPC253115
0.8113 Intermediate Similarity NPC471903
0.8108 Intermediate Similarity NPC475074
0.8103 Intermediate Similarity NPC471354
0.8103 Intermediate Similarity NPC471355
0.8103 Intermediate Similarity NPC471353
0.8103 Intermediate Similarity NPC474418
0.8103 Intermediate Similarity NPC142066
0.8103 Intermediate Similarity NPC309034
0.8103 Intermediate Similarity NPC157376
0.8103 Intermediate Similarity NPC158344
0.8103 Intermediate Similarity NPC471351
0.8103 Intermediate Similarity NPC473852
0.8103 Intermediate Similarity NPC243196
0.8103 Intermediate Similarity NPC196429
0.8103 Intermediate Similarity NPC77319
0.8103 Intermediate Similarity NPC84987
0.8103 Intermediate Similarity NPC27507
0.8103 Intermediate Similarity NPC244402
0.8103 Intermediate Similarity NPC99728
0.8103 Intermediate Similarity NPC50305
0.8103 Intermediate Similarity NPC34390
0.8103 Intermediate Similarity NPC87250
0.8095 Intermediate Similarity NPC201725
0.8095 Intermediate Similarity NPC191521
0.8091 Intermediate Similarity NPC272632
0.8091 Intermediate Similarity NPC200861
0.8087 Intermediate Similarity NPC69576
0.8087 Intermediate Similarity NPC31354
0.8087 Intermediate Similarity NPC471633
0.8087 Intermediate Similarity NPC84949
0.8077 Intermediate Similarity NPC130840
0.8067 Intermediate Similarity NPC471082
0.8056 Intermediate Similarity NPC38855
0.8056 Intermediate Similarity NPC251680
0.8053 Intermediate Similarity NPC177047
0.8051 Intermediate Similarity NPC79579
0.8037 Intermediate Similarity NPC231751
0.8036 Intermediate Similarity NPC50124
0.8034 Intermediate Similarity NPC153440
0.8034 Intermediate Similarity NPC83287
0.8018 Intermediate Similarity NPC472818
0.8017 Intermediate Similarity NPC310341
0.8017 Intermediate Similarity NPC470075
0.8017 Intermediate Similarity NPC99620
0.8017 Intermediate Similarity NPC193382
0.8017 Intermediate Similarity NPC199428
0.8017 Intermediate Similarity NPC5311
0.8016 Intermediate Similarity NPC289700
0.8016 Intermediate Similarity NPC62172
0.8 Intermediate Similarity NPC183570
0.8 Intermediate Similarity NPC112009
0.8 Intermediate Similarity NPC152778
0.8 Intermediate Similarity NPC205034
0.8 Intermediate Similarity NPC26046
0.8 Intermediate Similarity NPC162615
0.8 Intermediate Similarity NPC473979
0.8 Intermediate Similarity NPC85742
0.7983 Intermediate Similarity NPC475219
0.7983 Intermediate Similarity NPC231518
0.7982 Intermediate Similarity NPC475617
0.7982 Intermediate Similarity NPC474315
0.7966 Intermediate Similarity NPC5292
0.7966 Intermediate Similarity NPC153085
0.7966 Intermediate Similarity NPC268326
0.7965 Intermediate Similarity NPC472216
0.7965 Intermediate Similarity NPC5475
0.7965 Intermediate Similarity NPC284828
0.7965 Intermediate Similarity NPC173905
0.7963 Intermediate Similarity NPC92275
0.7963 Intermediate Similarity NPC181147
0.7949 Intermediate Similarity NPC203862
0.7949 Intermediate Similarity NPC290693
0.7949 Intermediate Similarity NPC93883
0.7949 Intermediate Similarity NPC152615
0.7946 Intermediate Similarity NPC472820
0.7946 Intermediate Similarity NPC64844
0.7946 Intermediate Similarity NPC179380
0.7946 Intermediate Similarity NPC42847
0.7937 Intermediate Similarity NPC158350
0.7934 Intermediate Similarity NPC8374
0.7931 Intermediate Similarity NPC216665
0.7928 Intermediate Similarity NPC472819
0.7928 Intermediate Similarity NPC473543
0.7925 Intermediate Similarity NPC119562
0.7925 Intermediate Similarity NPC105490
0.7925 Intermediate Similarity NPC279410
0.7917 Intermediate Similarity NPC107493
0.7917 Intermediate Similarity NPC193893
0.7917 Intermediate Similarity NPC115349
0.7909 Intermediate Similarity NPC476081
0.7909 Intermediate Similarity NPC11956
0.7909 Intermediate Similarity NPC475344
0.7909 Intermediate Similarity NPC476471
0.7909 Intermediate Similarity NPC32577
0.7909 Intermediate Similarity NPC114540
0.7909 Intermediate Similarity NPC155332
0.7905 Intermediate Similarity NPC234335
0.7899 Intermediate Similarity NPC474370
0.7899 Intermediate Similarity NPC475136
0.7899 Intermediate Similarity NPC475629
0.7899 Intermediate Similarity NPC475556
0.7899 Intermediate Similarity NPC474466
0.7899 Intermediate Similarity NPC474585
0.789 Intermediate Similarity NPC227865
0.789 Intermediate Similarity NPC473510
0.789 Intermediate Similarity NPC208358

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC44537 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
0.8448 Intermediate Similarity NPD7503 Approved
0.8131 Intermediate Similarity NPD7638 Approved
0.8056 Intermediate Similarity NPD7639 Approved
0.8056 Intermediate Similarity NPD7640 Approved
0.8034 Intermediate Similarity NPD7328 Approved
0.8034 Intermediate Similarity NPD7327 Approved
0.7983 Intermediate Similarity NPD8033 Approved
0.7966 Intermediate Similarity NPD7516 Approved
0.7833 Intermediate Similarity NPD8378 Approved
0.7833 Intermediate Similarity NPD8335 Approved
0.7833 Intermediate Similarity NPD8380 Approved
0.7833 Intermediate Similarity NPD8379 Approved
0.7833 Intermediate Similarity NPD8296 Approved
0.775 Intermediate Similarity NPD8294 Approved
0.775 Intermediate Similarity NPD8377 Approved
0.7647 Intermediate Similarity NPD7115 Discovery
0.7607 Intermediate Similarity NPD6053 Discontinued
0.7565 Intermediate Similarity NPD6899 Approved
0.7565 Intermediate Similarity NPD6881 Approved
0.7478 Intermediate Similarity NPD5697 Approved
0.744 Intermediate Similarity NPD7507 Approved
0.7436 Intermediate Similarity NPD6883 Approved
0.7436 Intermediate Similarity NPD7290 Approved
0.7436 Intermediate Similarity NPD7102 Approved
0.7434 Intermediate Similarity NPD7632 Discontinued
0.7407 Intermediate Similarity NPD7637 Suspended
0.7404 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7402 Intermediate Similarity NPD7319 Approved
0.7391 Intermediate Similarity NPD7128 Approved
0.7391 Intermediate Similarity NPD6675 Approved
0.7391 Intermediate Similarity NPD6402 Approved
0.7391 Intermediate Similarity NPD5739 Approved
0.7373 Intermediate Similarity NPD6650 Approved
0.7373 Intermediate Similarity NPD6617 Approved
0.7373 Intermediate Similarity NPD6869 Approved
0.7373 Intermediate Similarity NPD6649 Approved
0.7373 Intermediate Similarity NPD6847 Approved
0.7373 Intermediate Similarity NPD8130 Phase 1
0.735 Intermediate Similarity NPD6013 Approved
0.735 Intermediate Similarity NPD6012 Approved
0.735 Intermediate Similarity NPD6014 Approved
0.7311 Intermediate Similarity NPD8297 Approved
0.7311 Intermediate Similarity NPD6882 Approved
0.7308 Intermediate Similarity NPD6695 Phase 3
0.7265 Intermediate Similarity NPD6011 Approved
0.7265 Intermediate Similarity NPD7320 Approved
0.7257 Intermediate Similarity NPD6648 Approved
0.7222 Intermediate Similarity NPD6051 Approved
0.7203 Intermediate Similarity NPD6372 Approved
0.7203 Intermediate Similarity NPD6373 Approved
0.7193 Intermediate Similarity NPD5344 Discontinued
0.7184 Intermediate Similarity NPD7525 Registered
0.7179 Intermediate Similarity NPD5701 Approved
0.7168 Intermediate Similarity NPD4225 Approved
0.713 Intermediate Similarity NPD5211 Phase 2
0.7107 Intermediate Similarity NPD4632 Approved
0.7105 Intermediate Similarity NPD5285 Approved
0.7105 Intermediate Similarity NPD5286 Approved
0.7105 Intermediate Similarity NPD4696 Approved
0.708 Intermediate Similarity NPD6084 Phase 2
0.708 Intermediate Similarity NPD6083 Phase 2
0.7054 Intermediate Similarity NPD7736 Approved
0.704 Intermediate Similarity NPD6319 Approved
0.7037 Intermediate Similarity NPD7524 Approved
0.7037 Intermediate Similarity NPD7750 Discontinued
0.7019 Intermediate Similarity NPD6930 Phase 2
0.7019 Intermediate Similarity NPD6931 Approved
0.7019 Intermediate Similarity NPD7514 Phase 3
0.7009 Intermediate Similarity NPD5141 Approved
0.6983 Remote Similarity NPD5226 Approved
0.6983 Remote Similarity NPD5225 Approved
0.6983 Remote Similarity NPD4633 Approved
0.6983 Remote Similarity NPD5224 Approved
0.696 Remote Similarity NPD7101 Approved
0.696 Remote Similarity NPD7100 Approved
0.6953 Remote Similarity NPD7492 Approved
0.6949 Remote Similarity NPD6008 Approved
0.6942 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6935 Remote Similarity NPD6009 Approved
0.693 Remote Similarity NPD4755 Approved
0.6923 Remote Similarity NPD5175 Approved
0.6923 Remote Similarity NPD6929 Approved
0.6923 Remote Similarity NPD5174 Approved
0.6917 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6905 Remote Similarity NPD6054 Approved
0.6899 Remote Similarity NPD6616 Approved
0.6897 Remote Similarity NPD5223 Approved
0.6893 Remote Similarity NPD6932 Approved
0.6881 Remote Similarity NPD4751 Clinical (unspecified phase)
0.688 Remote Similarity NPD6335 Approved
0.6875 Remote Similarity NPD6399 Phase 3
0.6875 Remote Similarity NPD4202 Approved
0.6875 Remote Similarity NPD7604 Phase 2
0.686 Remote Similarity NPD4634 Approved
0.6857 Remote Similarity NPD7332 Phase 2
0.6855 Remote Similarity NPD6274 Approved
0.685 Remote Similarity NPD5983 Phase 2
0.6846 Remote Similarity NPD7078 Approved
0.6833 Remote Similarity NPD6686 Approved
0.6827 Remote Similarity NPD7145 Approved
0.6818 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6814 Remote Similarity NPD7748 Approved
0.681 Remote Similarity NPD4700 Approved
0.68 Remote Similarity NPD6317 Approved
0.6797 Remote Similarity NPD6370 Approved
0.6792 Remote Similarity NPD6902 Approved
0.6786 Remote Similarity NPD5284 Approved
0.6786 Remote Similarity NPD7515 Phase 2
0.6786 Remote Similarity NPD6079 Approved
0.6786 Remote Similarity NPD5281 Approved
0.6786 Remote Similarity NPD8034 Phase 2
0.6786 Remote Similarity NPD8035 Phase 2
0.6786 Remote Similarity NPD7087 Discontinued
0.6783 Remote Similarity NPD7902 Approved
0.6769 Remote Similarity NPD6336 Discontinued
0.6762 Remote Similarity NPD4195 Approved
0.6754 Remote Similarity NPD5695 Phase 3
0.675 Remote Similarity NPD6412 Phase 2
0.6746 Remote Similarity NPD6314 Approved
0.6746 Remote Similarity NPD6313 Approved
0.6731 Remote Similarity NPD6925 Approved
0.6731 Remote Similarity NPD5776 Phase 2
0.6727 Remote Similarity NPD4251 Approved
0.6727 Remote Similarity NPD4250 Approved
0.6724 Remote Similarity NPD5696 Approved
0.6721 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6719 Remote Similarity NPD6016 Approved
0.6719 Remote Similarity NPD6015 Approved
0.6713 Remote Similarity NPD7236 Approved
0.6697 Remote Similarity NPD6893 Approved
0.6697 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6696 Remote Similarity NPD7838 Discovery
0.6694 Remote Similarity NPD4730 Approved
0.6694 Remote Similarity NPD8133 Approved
0.6694 Remote Similarity NPD4729 Approved
0.6667 Remote Similarity NPD5988 Approved
0.6641 Remote Similarity NPD6059 Approved
0.6637 Remote Similarity NPD5693 Phase 1
0.6636 Remote Similarity NPD7521 Approved
0.6636 Remote Similarity NPD5330 Approved
0.6636 Remote Similarity NPD7146 Approved
0.6636 Remote Similarity NPD6409 Approved
0.6636 Remote Similarity NPD6684 Approved
0.6636 Remote Similarity NPD7334 Approved
0.6636 Remote Similarity NPD4249 Approved
0.6635 Remote Similarity NPD3701 Clinical (unspecified phase)
0.661 Remote Similarity NPD4159 Approved
0.6609 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6609 Remote Similarity NPD5210 Approved
0.6609 Remote Similarity NPD4629 Approved
0.6607 Remote Similarity NPD4753 Phase 2
0.6607 Remote Similarity NPD5328 Approved
0.6604 Remote Similarity NPD6683 Phase 2
0.6604 Remote Similarity NPD7645 Phase 2
0.6602 Remote Similarity NPD6924 Approved
0.6602 Remote Similarity NPD6926 Approved
0.6591 Remote Similarity NPD8293 Discontinued
0.6589 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6589 Remote Similarity NPD6908 Approved
0.6589 Remote Similarity NPD6909 Approved
0.6585 Remote Similarity NPD5251 Approved
0.6585 Remote Similarity NPD5247 Approved
0.6585 Remote Similarity NPD5249 Phase 3
0.6585 Remote Similarity NPD5250 Approved
0.6585 Remote Similarity NPD5248 Approved
0.6557 Remote Similarity NPD5128 Approved
0.6552 Remote Similarity NPD5221 Approved
0.6552 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6552 Remote Similarity NPD5222 Approved
0.6549 Remote Similarity NPD5785 Approved
0.6542 Remote Similarity NPD4822 Approved
0.6542 Remote Similarity NPD4819 Approved
0.6542 Remote Similarity NPD4820 Approved
0.6542 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6542 Remote Similarity NPD4821 Approved
0.6538 Remote Similarity NPD6942 Approved
0.6538 Remote Similarity NPD7339 Approved
0.6532 Remote Similarity NPD5216 Approved
0.6532 Remote Similarity NPD5215 Approved
0.6532 Remote Similarity NPD5217 Approved
0.6529 Remote Similarity NPD4768 Approved
0.6529 Remote Similarity NPD4767 Approved
0.6522 Remote Similarity NPD7900 Approved
0.6522 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6518 Remote Similarity NPD6903 Approved
0.6514 Remote Similarity NPD4788 Approved
0.65 Remote Similarity NPD4754 Approved
0.6496 Remote Similarity NPD5173 Approved
0.6491 Remote Similarity NPD5694 Approved
0.6491 Remote Similarity NPD6050 Approved
0.6486 Remote Similarity NPD7239 Suspended
0.6486 Remote Similarity NPD3618 Phase 1
0.6481 Remote Similarity NPD6898 Phase 1
0.6476 Remote Similarity NPD6933 Approved
0.6475 Remote Similarity NPD5954 Clinical (unspecified phase)
0.646 Remote Similarity NPD6080 Approved
0.646 Remote Similarity NPD6904 Approved
0.646 Remote Similarity NPD6673 Approved
0.6457 Remote Similarity NPD6868 Approved
0.6455 Remote Similarity NPD6400 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   15513540
ChEMBL   CHEMBL515692
ZINC  

Physicochemical Properties

Molecular Weight:  460.25
ALogP:  -0.9236
MLogP:  3.55
XLogP:  2.292
# Rotatable Bonds:  9
Polar Surface Area:  113.29
# H-Bond Aceptor:  7
# H-Bond Donor:  3
# Rings:  5
# Heavy Atoms:  33

Download Data

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