Natural Product: NPC476729

Natural Product ID:  NPC476729
Common Name:   Bruceine C
IUPAC Name:  
Synonyms:   Bruceine C
Molecular Formula:   C28H36O12
Standard InCHIKey:  KCVFVYXSNLKEHU-MBKFLBLHSA-N
Standard InCHI:  InChI=1S/C28H36O12/c1-11(25(3,4)36)7-16(30)40-19-21-27-10-38-28(21,24(35)37-6)22(33)18(32)20(27)26(5)9-14(29)17(31)12(2)13(26)8-15(27)39-23(19)34/h7,13,15,18-22,31-33,36H,8-10H2,1-6H3/b11-7+/t13-,15+,18+,19+,20+,21+,22-,26-,27+,28+/m0/s1
Canonical SMILES:  COC(=O)[C@]12OC[C@]34[C@H]2[C@@H](OC(=O)/C=C(/C(O)(C)C)C)C(=O)O[C@@H]4C[C@@H]2[C@]([C@H]3[C@H]([C@@H]1O)O)(C)CC(=O)C(=C2C)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
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota fruit Indonesia PMID[17896817]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1355 Organism Babesia gibsoni Babesia gibsoni IC50 = 0.107 ug/ml 17896817
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 0.005 ug/ml 3298551
NPT474 Organism Plasmodium berghei Plasmodium berghei Inhibition = 40 % 3298551
NPT992 Organism Entamoeba histolytica Entamoeba histolytica IC50 = 0.279 ug/ml 10.1007/s00044-011-9767-1

  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 NPC476729 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
0.9912 High Similarity NPC105926
0.9912 High Similarity NPC265557
0.9912 High Similarity NPC18945
0.9912 High Similarity NPC91693
0.9825 High Similarity NPC312833
0.9739 High Similarity NPC67251
0.9655 High Similarity NPC24651
0.9565 High Similarity NPC470779
0.9328 High Similarity NPC476008
0.9322 High Similarity NPC470922
0.9304 High Similarity NPC17772
0.9304 High Similarity NPC470776
0.9298 High Similarity NPC16081
0.9298 High Similarity NPC173686
0.9244 High Similarity NPC477745
0.9224 High Similarity NPC470777
0.9217 High Similarity NPC473590
0.9217 High Similarity NPC146432
0.9217 High Similarity NPC470778
0.9211 High Similarity NPC143268
0.9211 High Similarity NPC323821
0.9211 High Similarity NPC268238
0.9211 High Similarity NPC45218
0.9194 High Similarity NPC251998
0.9138 High Similarity NPC251310
0.913 High Similarity NPC328374
0.913 High Similarity NPC213084
0.913 High Similarity NPC96312
0.913 High Similarity NPC190185
0.913 High Similarity NPC474734
0.913 High Similarity NPC89929
0.913 High Similarity NPC40632
0.913 High Similarity NPC251236
0.9123 High Similarity NPC94509
0.912 High Similarity NPC295885
0.912 High Similarity NPC140045
0.9113 High Similarity NPC262813
0.9052 High Similarity NPC122033
0.9052 High Similarity NPC470775
0.9052 High Similarity NPC97908
0.9052 High Similarity NPC287343
0.9052 High Similarity NPC470854
0.9052 High Similarity NPC474654
0.9052 High Similarity NPC176513
0.9043 High Similarity NPC299849
0.9043 High Similarity NPC473798
0.904 High Similarity NPC471089
0.904 High Similarity NPC141215
0.904 High Similarity NPC190065
0.8983 High Similarity NPC109607
0.8983 High Similarity NPC107338
0.8983 High Similarity NPC112038
0.8974 High Similarity NPC297179
0.8968 High Similarity NPC596
0.8957 High Similarity NPC49451
0.8952 High Similarity NPC168879
0.8898 High Similarity NPC476529
0.8898 High Similarity NPC475775
0.8871 High Similarity NPC102316
0.8814 High Similarity NPC204552
0.8814 High Similarity NPC188667
0.8803 High Similarity NPC470628
0.8803 High Similarity NPC152199
0.8803 High Similarity NPC474046
0.8803 High Similarity NPC235539
0.8803 High Similarity NPC259306
0.8803 High Similarity NPC134869
0.8793 High Similarity NPC208998
0.8793 High Similarity NPC7921
0.875 High Similarity NPC102822
0.875 High Similarity NPC477046
0.8729 High Similarity NPC473968
0.8718 High Similarity NPC470919
0.8718 High Similarity NPC18547
0.8718 High Similarity NPC474906
0.8718 High Similarity NPC469877
0.871 High Similarity NPC476851
0.8707 High Similarity NPC269530
0.8699 High Similarity NPC470780
0.8678 High Similarity NPC269642
0.8644 High Similarity NPC207217
0.864 High Similarity NPC476852
0.8632 High Similarity NPC198539
0.8632 High Similarity NPC51978
0.8629 High Similarity NPC476859
0.8629 High Similarity NPC475636
0.8629 High Similarity NPC295220
0.8621 High Similarity NPC171888
0.8621 High Similarity NPC146945
0.8618 High Similarity NPC87662
0.8618 High Similarity NPC293112
0.8618 High Similarity NPC181999
0.8594 High Similarity NPC243014
0.8583 High Similarity NPC469488
0.8571 High Similarity NPC476193
0.8571 High Similarity NPC478154
0.8571 High Similarity NPC469684
0.856 High Similarity NPC309096
0.856 High Similarity NPC54614
0.856 High Similarity NPC476854
0.8559 High Similarity NPC117712
0.8548 High Similarity NPC470882
0.8547 High Similarity NPC474516
0.8547 High Similarity NPC289312
0.8547 High Similarity NPC302146
0.8547 High Similarity NPC472002
0.8547 High Similarity NPC11252
0.8547 High Similarity NPC317687
0.8537 High Similarity NPC172154
0.8537 High Similarity NPC81736
0.8525 High Similarity NPC222688
0.8522 High Similarity NPC293850
0.8512 High Similarity NPC109973
0.8512 High Similarity NPC478051
0.8504 High Similarity NPC478151
0.85 High Similarity NPC240509
0.8492 Intermediate Similarity NPC476074
0.8492 Intermediate Similarity NPC262796
0.8492 Intermediate Similarity NPC329993
0.8492 Intermediate Similarity NPC475377
0.8492 Intermediate Similarity NPC264566
0.8492 Intermediate Similarity NPC25998
0.8492 Intermediate Similarity NPC134914
0.8492 Intermediate Similarity NPC172374
0.8492 Intermediate Similarity NPC478155
0.8492 Intermediate Similarity NPC476855
0.8492 Intermediate Similarity NPC45346
0.8492 Intermediate Similarity NPC478064
0.8492 Intermediate Similarity NPC173435
0.8492 Intermediate Similarity NPC301639
0.8492 Intermediate Similarity NPC475167
0.8492 Intermediate Similarity NPC478065
0.8487 Intermediate Similarity NPC179626
0.848 Intermediate Similarity NPC188291
0.8475 Intermediate Similarity NPC477126
0.8475 Intermediate Similarity NPC25909
0.8468 Intermediate Similarity NPC473635
0.8468 Intermediate Similarity NPC225049
0.8462 Intermediate Similarity NPC317107
0.8462 Intermediate Similarity NPC157476
0.8462 Intermediate Similarity NPC201992
0.8455 Intermediate Similarity NPC227397
0.8455 Intermediate Similarity NPC11895
0.8455 Intermediate Similarity NPC469789
0.8448 Intermediate Similarity NPC27814
0.8448 Intermediate Similarity NPC141350
0.8443 Intermediate Similarity NPC4021
0.8443 Intermediate Similarity NPC159456
0.8435 Intermediate Similarity NPC144854
0.8435 Intermediate Similarity NPC3316
0.843 Intermediate Similarity NPC77689
0.843 Intermediate Similarity NPC268958
0.843 Intermediate Similarity NPC230513
0.843 Intermediate Similarity NPC473636
0.843 Intermediate Similarity NPC475041
0.8425 Intermediate Similarity NPC478152
0.8425 Intermediate Similarity NPC478153
0.8425 Intermediate Similarity NPC254614
0.8425 Intermediate Similarity NPC100390
0.8425 Intermediate Similarity NPC478150
0.8417 Intermediate Similarity NPC134430
0.8417 Intermediate Similarity NPC58662
0.8417 Intermediate Similarity NPC98249
0.8417 Intermediate Similarity NPC477116
0.8417 Intermediate Similarity NPC55296
0.8417 Intermediate Similarity NPC27999
0.8417 Intermediate Similarity NPC53396
0.8413 Intermediate Similarity NPC231529
0.8413 Intermediate Similarity NPC477196
0.84 Intermediate Similarity NPC473265
0.8387 Intermediate Similarity NPC8369
0.8376 Intermediate Similarity NPC5103
0.8374 Intermediate Similarity NPC470265
0.8374 Intermediate Similarity NPC23786
0.8374 Intermediate Similarity NPC170538
0.8362 Intermediate Similarity NPC208461
0.8362 Intermediate Similarity NPC154608
0.8362 Intermediate Similarity NPC192813
0.8362 Intermediate Similarity NPC289702
0.8362 Intermediate Similarity NPC277017
0.8361 Intermediate Similarity NPC472004
0.8361 Intermediate Similarity NPC268530
0.8361 Intermediate Similarity NPC154491
0.8361 Intermediate Similarity NPC251226
0.8361 Intermediate Similarity NPC476961
0.8347 Intermediate Similarity NPC478206
0.8347 Intermediate Similarity NPC478205
0.8347 Intermediate Similarity NPC21326
0.8347 Intermediate Similarity NPC284707
0.8347 Intermediate Similarity NPC108581
0.8346 Intermediate Similarity NPC476863
0.8346 Intermediate Similarity NPC477197
0.8346 Intermediate Similarity NPC476862
0.8333 Intermediate Similarity NPC477078
0.8333 Intermediate Similarity NPC477713
0.8333 Intermediate Similarity NPC477075
0.8333 Intermediate Similarity NPC266728
0.8333 Intermediate Similarity NPC477712
0.8333 Intermediate Similarity NPC475281
0.8333 Intermediate Similarity NPC329923

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC476729 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
0.8362 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.816 Intermediate Similarity NPD8328 Phase 3
0.8065 Intermediate Similarity NPD6319 Approved
0.7984 Intermediate Similarity NPD7319 Approved
0.7967 Intermediate Similarity NPD7115 Discovery
0.7833 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7833 Intermediate Similarity NPD6373 Approved
0.7833 Intermediate Similarity NPD6372 Approved
0.7812 Intermediate Similarity NPD7492 Approved
0.7787 Intermediate Similarity NPD8297 Approved
0.7778 Intermediate Similarity NPD6054 Approved
0.7778 Intermediate Similarity NPD6059 Approved
0.7769 Intermediate Similarity NPD7736 Approved
0.7769 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7752 Intermediate Similarity NPD7507 Approved
0.7752 Intermediate Similarity NPD6616 Approved
0.7731 Intermediate Similarity NPD6675 Approved
0.7731 Intermediate Similarity NPD7128 Approved
0.7731 Intermediate Similarity NPD6402 Approved
0.7731 Intermediate Similarity NPD5739 Approved
0.7717 Intermediate Similarity NPD6921 Approved
0.7705 Intermediate Similarity NPD6649 Approved
0.7705 Intermediate Similarity NPD6650 Approved
0.7692 Intermediate Similarity NPD7078 Approved
0.7692 Intermediate Similarity NPD8293 Discontinued
0.768 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7672 Intermediate Similarity NPD4225 Approved
0.7656 Intermediate Similarity NPD6370 Approved
0.7603 Intermediate Similarity NPD6899 Approved
0.7603 Intermediate Similarity NPD7320 Approved
0.7603 Intermediate Similarity NPD6881 Approved
0.7603 Intermediate Similarity NPD6686 Approved
0.7581 Intermediate Similarity NPD4632 Approved
0.7578 Intermediate Similarity NPD8513 Phase 3
0.7578 Intermediate Similarity NPD8516 Approved
0.7578 Intermediate Similarity NPD6015 Approved
0.7578 Intermediate Similarity NPD8515 Approved
0.7578 Intermediate Similarity NPD6016 Approved
0.7578 Intermediate Similarity NPD8517 Approved
0.7521 Intermediate Similarity NPD5701 Approved
0.7521 Intermediate Similarity NPD5697 Approved
0.7521 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD5988 Approved
0.75 Intermediate Similarity NPD6882 Approved
0.748 Intermediate Similarity NPD7102 Approved
0.748 Intermediate Similarity NPD7290 Approved
0.748 Intermediate Similarity NPD6883 Approved
0.7458 Intermediate Similarity NPD7639 Approved
0.7458 Intermediate Similarity NPD7640 Approved
0.7422 Intermediate Similarity NPD7516 Approved
0.7419 Intermediate Similarity NPD8130 Phase 1
0.7419 Intermediate Similarity NPD6869 Approved
0.7419 Intermediate Similarity NPD6617 Approved
0.7419 Intermediate Similarity NPD6847 Approved
0.7402 Intermediate Similarity NPD6009 Approved
0.7398 Intermediate Similarity NPD6012 Approved
0.7398 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7398 Intermediate Similarity NPD6014 Approved
0.7398 Intermediate Similarity NPD6013 Approved
0.7373 Intermediate Similarity NPD7638 Approved
0.7344 Intermediate Similarity NPD7327 Approved
0.7344 Intermediate Similarity NPD7328 Approved
0.7339 Intermediate Similarity NPD4634 Approved
0.7328 Intermediate Similarity NPD7604 Phase 2
0.7317 Intermediate Similarity NPD6011 Approved
0.7308 Intermediate Similarity NPD5983 Phase 2
0.728 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD6033 Approved
0.7236 Intermediate Similarity NPD6412 Phase 2
0.7218 Intermediate Similarity NPD6336 Discontinued
0.7206 Intermediate Similarity NPD7260 Phase 2
0.719 Intermediate Similarity NPD5211 Phase 2
0.7176 Intermediate Similarity NPD8379 Approved
0.7176 Intermediate Similarity NPD8296 Approved
0.7176 Intermediate Similarity NPD8378 Approved
0.7176 Intermediate Similarity NPD8380 Approved
0.7176 Intermediate Similarity NPD8335 Approved
0.7176 Intermediate Similarity NPD7503 Approved
0.7164 Intermediate Similarity NPD8074 Phase 3
0.7154 Intermediate Similarity NPD6008 Approved
0.7143 Intermediate Similarity NPD6083 Phase 2
0.7143 Intermediate Similarity NPD4755 Approved
0.7143 Intermediate Similarity NPD6084 Phase 2
0.7143 Intermediate Similarity NPD7902 Approved
0.7143 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD8294 Approved
0.7099 Intermediate Similarity NPD8377 Approved
0.7097 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD5696 Approved
0.7073 Intermediate Similarity NPD5141 Approved
0.7063 Intermediate Similarity NPD6371 Approved
0.7054 Intermediate Similarity NPD6274 Approved
0.7045 Intermediate Similarity NPD8033 Approved
0.7034 Intermediate Similarity NPD7748 Approved
0.7031 Intermediate Similarity NPD8133 Approved
0.7029 Intermediate Similarity NPD6845 Suspended
0.7025 Intermediate Similarity NPD5285 Approved
0.7025 Intermediate Similarity NPD4700 Approved
0.7025 Intermediate Similarity NPD5286 Approved
0.7025 Intermediate Similarity NPD4696 Approved
0.7023 Intermediate Similarity NPD7100 Approved
0.7023 Intermediate Similarity NPD7101 Approved
0.7009 Intermediate Similarity NPD7515 Phase 2
0.6967 Remote Similarity NPD5344 Discontinued
0.6953 Remote Similarity NPD6053 Discontinued
0.6947 Remote Similarity NPD6335 Approved
0.6923 Remote Similarity NPD6698 Approved
0.6923 Remote Similarity NPD46 Approved
0.6917 Remote Similarity NPD4697 Phase 3
0.6917 Remote Similarity NPD6909 Approved
0.6917 Remote Similarity NPD6908 Approved
0.6911 Remote Similarity NPD7632 Discontinued
0.6911 Remote Similarity NPD5224 Approved
0.6911 Remote Similarity NPD5225 Approved
0.6911 Remote Similarity NPD5226 Approved
0.6911 Remote Similarity NPD4633 Approved
0.6891 Remote Similarity NPD7900 Approved
0.6891 Remote Similarity NPD5282 Discontinued
0.6891 Remote Similarity NPD7901 Clinical (unspecified phase)
0.688 Remote Similarity NPD4768 Approved
0.688 Remote Similarity NPD4767 Approved
0.687 Remote Similarity NPD6317 Approved
0.6855 Remote Similarity NPD5175 Approved
0.6855 Remote Similarity NPD5174 Approved
0.6838 Remote Similarity NPD5328 Approved
0.6833 Remote Similarity NPD5695 Phase 3
0.6831 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6829 Remote Similarity NPD5223 Approved
0.6818 Remote Similarity NPD6313 Approved
0.6818 Remote Similarity NPD6314 Approved
0.681 Remote Similarity NPD3573 Approved
0.6807 Remote Similarity NPD5778 Approved
0.6807 Remote Similarity NPD6399 Phase 3
0.6807 Remote Similarity NPD5779 Approved
0.6794 Remote Similarity NPD6868 Approved
0.6791 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6777 Remote Similarity NPD5221 Approved
0.6777 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6777 Remote Similarity NPD5222 Approved
0.6772 Remote Similarity NPD4730 Approved
0.6772 Remote Similarity NPD4729 Approved
0.6752 Remote Similarity NPD6672 Approved
0.6752 Remote Similarity NPD5737 Approved
0.6724 Remote Similarity NPD3618 Phase 1
0.6723 Remote Similarity NPD7983 Approved
0.6723 Remote Similarity NPD6079 Approved
0.6723 Remote Similarity NPD5693 Phase 1
0.6723 Remote Similarity NPD6411 Approved
0.6721 Remote Similarity NPD5173 Approved
0.672 Remote Similarity NPD4754 Approved
0.6694 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5248 Approved
0.6667 Remote Similarity NPD5249 Phase 3
0.6667 Remote Similarity NPD5247 Approved
0.6667 Remote Similarity NPD5251 Approved
0.6667 Remote Similarity NPD5250 Approved
0.6643 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6641 Remote Similarity NPD5128 Approved
0.6638 Remote Similarity NPD1694 Approved
0.6613 Remote Similarity NPD6648 Approved
0.6609 Remote Similarity NPD6110 Phase 1
0.6568 Remote Similarity NPD8434 Phase 2
0.6557 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6557 Remote Similarity NPD5210 Approved
0.6557 Remote Similarity NPD4629 Approved
0.6555 Remote Similarity NPD4753 Phase 2
0.6555 Remote Similarity NPD6101 Approved
0.6555 Remote Similarity NPD6904 Approved
0.6555 Remote Similarity NPD6673 Approved
0.6555 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6555 Remote Similarity NPD6080 Approved
0.6529 Remote Similarity NPD4202 Approved
0.6525 Remote Similarity NPD5956 Approved
0.6489 Remote Similarity NPD5216 Approved
0.6489 Remote Similarity NPD5217 Approved
0.6489 Remote Similarity NPD5215 Approved
0.6471 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6458 Remote Similarity NPD8415 Approved
0.645 Remote Similarity NPD8407 Phase 2
0.6449 Remote Similarity NPD6067 Discontinued
0.6446 Remote Similarity NPD8035 Phase 2
0.6446 Remote Similarity NPD7637 Suspended
0.6446 Remote Similarity NPD8034 Phase 2
0.6441 Remote Similarity NPD5330 Approved
0.6441 Remote Similarity NPD7334 Approved
0.6441 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6441 Remote Similarity NPD6409 Approved
0.6441 Remote Similarity NPD6684 Approved
0.6441 Remote Similarity NPD7146 Approved
0.6441 Remote Similarity NPD7521 Approved
0.6438 Remote Similarity NPD6333 Approved
0.6438 Remote Similarity NPD6334 Approved
0.6429 Remote Similarity NPD1700 Approved
0.6424 Remote Similarity NPD7799 Discontinued
0.6417 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6412 Remote Similarity NPD5135 Approved
0.6412 Remote Similarity NPD5169 Approved
0.6412 Remote Similarity NPD5134 Clinical (unspecified phase)
0.64 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6379 Remote Similarity NPD4752 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   44584512
ChEMBL   CHEMBL455759
ZINC  

Physicochemical Properties

Molecular Weight:  564.22
ALogP:  -0.902
MLogP:  3.22
XLogP:  0.076
# Rotatable Bonds:  16
Polar Surface Area:  186.12
# H-Bond Aceptor:  12
# H-Bond Donor:  4
# Rings:  5
# Heavy Atoms:  40

Download Data

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