Natural Product: NPC328737

Natural Product ID:  NPC328737
Common Name:   Breynceanothanolic Acid
IUPAC Name:  
Synonyms:   breynceanothanolic acid
Molecular Formula:   C29H40O5
Standard InCHIKey:  SNCMVKNGLNUISS-GCWSBASFSA-N
Standard InCHI:  InChI=1S/C29H40O5/c1-16(2)18-7-9-25(21(30)31)12-13-26-19(20(18)25)8-10-28(33-22(26)32)24(26,6)11-14-27-23(4,5)15-17(3)29(27,28)34-27/h17-20H,1,7-15H2,2-6H3,(H,30,31)/t17-,18-,19+,20+,24-,25-,26+,27+,28+,29-/m0/s1
Canonical SMILES:  CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@]34[C@@]([C@@]1(CC2)C(=O)O3)(C)CC[C@@]12[C@@]4(O1)[C@@H](C)CC2(C)C)C(=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
NPO26000 Breynia fruticosa Species Phyllanthaceae Eukaryota roots Xishuangbanna of Yunnan Province, China PMID[21428418]
NPO26000 Breynia fruticosa Species Phyllanthaceae Eukaryota Root PMID[21428418]

  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 = 10200 nM 21428418
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 = 14300 nM 21428418
NPT81 Cell Line A549 Homo sapiens IC50 = 14500 nM 21428418
NPT83 Cell Line MCF7 Homo sapiens IC50 = 12700 nM 21428418
NPT660 Cell Line SW480 Homo sapiens IC50 = 20000 nM 21428418

  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 NPC328737 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
0.8269 Intermediate Similarity NPC124544
0.8252 Intermediate Similarity NPC108371
0.8173 Intermediate Similarity NPC121218
0.8173 Intermediate Similarity NPC253886
0.8155 Intermediate Similarity NPC472028
0.8148 Intermediate Similarity NPC154906
0.8113 Intermediate Similarity NPC301787
0.8113 Intermediate Similarity NPC471293
0.8095 Intermediate Similarity NPC170615
0.8077 Intermediate Similarity NPC94906
0.8058 Intermediate Similarity NPC469810
0.8058 Intermediate Similarity NPC253586
0.8037 Intermediate Similarity NPC222833
0.8037 Intermediate Similarity NPC138908
0.8037 Intermediate Similarity NPC200957
0.8 Intermediate Similarity NPC295276
0.8 Intermediate Similarity NPC252614
0.7981 Intermediate Similarity NPC38471
0.7981 Intermediate Similarity NPC98837
0.7981 Intermediate Similarity NPC162459
0.7981 Intermediate Similarity NPC28864
0.7981 Intermediate Similarity NPC20479
0.7981 Intermediate Similarity NPC38296
0.7963 Intermediate Similarity NPC166993
0.7963 Intermediate Similarity NPC59530
0.7961 Intermediate Similarity NPC234564
0.7961 Intermediate Similarity NPC256227
0.7944 Intermediate Similarity NPC47281
0.7941 Intermediate Similarity NPC477495
0.7931 Intermediate Similarity NPC65858
0.7925 Intermediate Similarity NPC304832
0.7925 Intermediate Similarity NPC214946
0.7925 Intermediate Similarity NPC88203
0.7925 Intermediate Similarity NPC76866
0.7925 Intermediate Similarity NPC148628
0.7925 Intermediate Similarity NPC246736
0.7925 Intermediate Similarity NPC286519
0.7905 Intermediate Similarity NPC37047
0.7905 Intermediate Similarity NPC477656
0.7905 Intermediate Similarity NPC180733
0.7905 Intermediate Similarity NPC293866
0.7905 Intermediate Similarity NPC41971
0.789 Intermediate Similarity NPC231278
0.789 Intermediate Similarity NPC218123
0.789 Intermediate Similarity NPC273155
0.789 Intermediate Similarity NPC112895
0.7885 Intermediate Similarity NPC190080
0.7885 Intermediate Similarity NPC111187
0.7876 Intermediate Similarity NPC298278
0.787 Intermediate Similarity NPC37600
0.787 Intermediate Similarity NPC28791
0.787 Intermediate Similarity NPC50535
0.787 Intermediate Similarity NPC295366
0.7864 Intermediate Similarity NPC197158
0.7864 Intermediate Similarity NPC471624
0.7864 Intermediate Similarity NPC263135
0.7864 Intermediate Similarity NPC288906
0.7863 Intermediate Similarity NPC135038
0.7863 Intermediate Similarity NPC43252
0.7863 Intermediate Similarity NPC267822
0.785 Intermediate Similarity NPC277074
0.785 Intermediate Similarity NPC140723
0.785 Intermediate Similarity NPC122811
0.785 Intermediate Similarity NPC209298
0.7838 Intermediate Similarity NPC94650
0.783 Intermediate Similarity NPC52899
0.783 Intermediate Similarity NPC75941
0.783 Intermediate Similarity NPC46848
0.783 Intermediate Similarity NPC163963
0.783 Intermediate Similarity NPC39683
0.783 Intermediate Similarity NPC289148
0.7822 Intermediate Similarity NPC10274
0.7812 Intermediate Similarity NPC232625
0.781 Intermediate Similarity NPC119036
0.781 Intermediate Similarity NPC89099
0.78 Intermediate Similarity NPC250687
0.78 Intermediate Similarity NPC254572
0.78 Intermediate Similarity NPC48824
0.78 Intermediate Similarity NPC229407
0.7798 Intermediate Similarity NPC86852
0.7798 Intermediate Similarity NPC251824
0.7797 Intermediate Similarity NPC169818
0.7788 Intermediate Similarity NPC29410
0.7788 Intermediate Similarity NPC116683
0.7788 Intermediate Similarity NPC200054
0.7778 Intermediate Similarity NPC100078
0.7768 Intermediate Similarity NPC280782
0.7757 Intermediate Similarity NPC213528
0.7757 Intermediate Similarity NPC244969
0.7757 Intermediate Similarity NPC193934
0.7757 Intermediate Similarity NPC271980
0.7757 Intermediate Similarity NPC275990
0.7748 Intermediate Similarity NPC130302
0.7745 Intermediate Similarity NPC219516
0.7736 Intermediate Similarity NPC477655
0.7736 Intermediate Similarity NPC287676
0.7723 Intermediate Similarity NPC269267
0.7719 Intermediate Similarity NPC266728
0.7719 Intermediate Similarity NPC196931
0.7719 Intermediate Similarity NPC49492
0.7714 Intermediate Similarity NPC10864
0.7706 Intermediate Similarity NPC166079
0.7706 Intermediate Similarity NPC472655
0.7706 Intermediate Similarity NPC306776
0.7699 Intermediate Similarity NPC285086
0.7699 Intermediate Similarity NPC317210
0.7699 Intermediate Similarity NPC102619
0.7692 Intermediate Similarity NPC241047
0.7692 Intermediate Similarity NPC82633
0.7692 Intermediate Similarity NPC98639
0.7692 Intermediate Similarity NPC470229
0.7685 Intermediate Similarity NPC87927
0.7685 Intermediate Similarity NPC470310
0.7672 Intermediate Similarity NPC42673
0.767 Intermediate Similarity NPC224060
0.767 Intermediate Similarity NPC244356
0.767 Intermediate Similarity NPC294263
0.7664 Intermediate Similarity NPC289670
0.7642 Intermediate Similarity NPC471038
0.7642 Intermediate Similarity NPC16911
0.7642 Intermediate Similarity NPC78427
0.7632 Intermediate Similarity NPC470116
0.7632 Intermediate Similarity NPC470115
0.7632 Intermediate Similarity NPC300051
0.7632 Intermediate Similarity NPC326542
0.7627 Intermediate Similarity NPC222688
0.7619 Intermediate Similarity NPC235109
0.7619 Intermediate Similarity NPC111834
0.7619 Intermediate Similarity NPC169270
0.7619 Intermediate Similarity NPC292718
0.7619 Intermediate Similarity NPC329910
0.7619 Intermediate Similarity NPC306797
0.7619 Intermediate Similarity NPC163685
0.7615 Intermediate Similarity NPC98603
0.7615 Intermediate Similarity NPC84928
0.7615 Intermediate Similarity NPC29705
0.7611 Intermediate Similarity NPC476964
0.7611 Intermediate Similarity NPC207251
0.7607 Intermediate Similarity NPC143755
0.76 Intermediate Similarity NPC80590
0.7596 Intermediate Similarity NPC277399
0.7596 Intermediate Similarity NPC475118
0.7593 Intermediate Similarity NPC22388
0.7589 Intermediate Similarity NPC98633
0.7589 Intermediate Similarity NPC76084
0.7589 Intermediate Similarity NPC471093
0.7589 Intermediate Similarity NPC255655
0.7589 Intermediate Similarity NPC124053
0.7573 Intermediate Similarity NPC471747
0.757 Intermediate Similarity NPC470388
0.7568 Intermediate Similarity NPC473517
0.7568 Intermediate Similarity NPC258323
0.7568 Intermediate Similarity NPC63841
0.7568 Intermediate Similarity NPC211224
0.7565 Intermediate Similarity NPC469794
0.7565 Intermediate Similarity NPC72772
0.7547 Intermediate Similarity NPC170978
0.7547 Intermediate Similarity NPC274793
0.7545 Intermediate Similarity NPC278628
0.7545 Intermediate Similarity NPC285927
0.7545 Intermediate Similarity NPC231530
0.7545 Intermediate Similarity NPC196528
0.7545 Intermediate Similarity NPC470587
0.7544 Intermediate Similarity NPC97002
0.7544 Intermediate Similarity NPC962
0.7544 Intermediate Similarity NPC250109
0.7544 Intermediate Similarity NPC52634
0.7544 Intermediate Similarity NPC471252
0.7542 Intermediate Similarity NPC310511
0.7524 Intermediate Similarity NPC279974
0.7524 Intermediate Similarity NPC470232
0.7524 Intermediate Similarity NPC205173
0.7523 Intermediate Similarity NPC225238
0.7523 Intermediate Similarity NPC471005
0.7523 Intermediate Similarity NPC216114
0.7523 Intermediate Similarity NPC469985
0.7522 Intermediate Similarity NPC272242
0.7522 Intermediate Similarity NPC471251
0.7522 Intermediate Similarity NPC56025
0.7522 Intermediate Similarity NPC469656
0.7522 Intermediate Similarity NPC470311
0.7522 Intermediate Similarity NPC29505
0.7522 Intermediate Similarity NPC474846
0.7522 Intermediate Similarity NPC469655
0.7522 Intermediate Similarity NPC470281
0.7521 Intermediate Similarity NPC472667
0.7521 Intermediate Similarity NPC230513
0.75 Intermediate Similarity NPC475958
0.75 Intermediate Similarity NPC475061
0.75 Intermediate Similarity NPC473570
0.75 Intermediate Similarity NPC477053
0.75 Intermediate Similarity NPC477051
0.75 Intermediate Similarity NPC469790
0.75 Intermediate Similarity NPC204652
0.75 Intermediate Similarity NPC274827
0.75 Intermediate Similarity NPC49532
0.75 Intermediate Similarity NPC291373
0.75 Intermediate Similarity NPC471790
0.75 Intermediate Similarity NPC477052
0.75 Intermediate Similarity NPC471250

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC328737 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
0.7706 Intermediate Similarity NPD6008 Approved
0.75 Intermediate Similarity NPD1700 Approved
0.7411 Intermediate Similarity NPD7320 Approved
0.7404 Intermediate Similarity NPD8035 Phase 2
0.7404 Intermediate Similarity NPD8034 Phase 2
0.7377 Intermediate Similarity NPD7078 Approved
0.7358 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD5739 Approved
0.7232 Intermediate Similarity NPD6402 Approved
0.7232 Intermediate Similarity NPD7128 Approved
0.7232 Intermediate Similarity NPD6675 Approved
0.7213 Intermediate Similarity NPD7492 Approved
0.7193 Intermediate Similarity NPD6372 Approved
0.7193 Intermediate Similarity NPD6373 Approved
0.7177 Intermediate Similarity NPD7736 Approved
0.7167 Intermediate Similarity NPD6059 Approved
0.7167 Intermediate Similarity NPD6054 Approved
0.7157 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7155 Intermediate Similarity NPD8297 Approved
0.7154 Intermediate Similarity NPD6616 Approved
0.7154 Intermediate Similarity NPD7507 Approved
0.712 Intermediate Similarity NPD7319 Approved
0.7105 Intermediate Similarity NPD6881 Approved
0.7105 Intermediate Similarity NPD6899 Approved
0.7105 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD6001 Approved
0.7097 Intermediate Similarity NPD8293 Discontinued
0.7094 Intermediate Similarity NPD4632 Approved
0.7069 Intermediate Similarity NPD6650 Approved
0.7069 Intermediate Similarity NPD6649 Approved
0.7049 Intermediate Similarity NPD6370 Approved
0.7025 Intermediate Similarity NPD6319 Approved
0.7018 Intermediate Similarity NPD5701 Approved
0.7018 Intermediate Similarity NPD5697 Approved
0.7 Intermediate Similarity NPD7638 Approved
0.6992 Remote Similarity NPD7604 Phase 2
0.6983 Remote Similarity NPD7290 Approved
0.6983 Remote Similarity NPD6883 Approved
0.6983 Remote Similarity NPD7102 Approved
0.6983 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6967 Remote Similarity NPD6015 Approved
0.6967 Remote Similarity NPD6016 Approved
0.6949 Remote Similarity NPD8133 Approved
0.6937 Remote Similarity NPD7640 Approved
0.6937 Remote Similarity NPD7639 Approved
0.6923 Remote Similarity NPD6617 Approved
0.6923 Remote Similarity NPD6847 Approved
0.6923 Remote Similarity NPD8130 Phase 1
0.6923 Remote Similarity NPD6869 Approved
0.6917 Remote Similarity NPD6009 Approved
0.6911 Remote Similarity NPD5988 Approved
0.6909 Remote Similarity NPD6083 Phase 2
0.6909 Remote Similarity NPD6084 Phase 2
0.6897 Remote Similarity NPD6013 Approved
0.6897 Remote Similarity NPD6012 Approved
0.6897 Remote Similarity NPD6014 Approved
0.6897 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6864 Remote Similarity NPD6882 Approved
0.6852 Remote Similarity NPD6399 Phase 3
0.6847 Remote Similarity NPD5696 Approved
0.6829 Remote Similarity NPD5983 Phase 2
0.681 Remote Similarity NPD6011 Approved
0.6803 Remote Similarity NPD7516 Approved
0.68 Remote Similarity NPD6697 Approved
0.68 Remote Similarity NPD6114 Approved
0.68 Remote Similarity NPD6115 Approved
0.68 Remote Similarity NPD6118 Approved
0.6796 Remote Similarity NPD4788 Approved
0.678 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6777 Remote Similarity NPD7115 Discovery
0.6762 Remote Similarity NPD6098 Approved
0.6757 Remote Similarity NPD4755 Approved
0.6746 Remote Similarity NPD6336 Discontinued
0.6729 Remote Similarity NPD6673 Approved
0.6729 Remote Similarity NPD6080 Approved
0.6729 Remote Similarity NPD6904 Approved
0.6727 Remote Similarity NPD5695 Phase 3
0.6724 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6721 Remote Similarity NPD7327 Approved
0.6721 Remote Similarity NPD7328 Approved
0.6696 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3702 Approved
0.6667 Remote Similarity NPD5207 Approved
0.6641 Remote Similarity NPD6033 Approved
0.6637 Remote Similarity NPD4696 Approved
0.6637 Remote Similarity NPD5286 Approved
0.6637 Remote Similarity NPD4700 Approved
0.6637 Remote Similarity NPD5285 Approved
0.6636 Remote Similarity NPD6903 Approved
0.6606 Remote Similarity NPD5284 Approved
0.6606 Remote Similarity NPD5281 Approved
0.66 Remote Similarity NPD6117 Approved
0.6583 Remote Similarity NPD6053 Discontinued
0.6581 Remote Similarity NPD6412 Phase 2
0.6574 Remote Similarity NPD5328 Approved
0.656 Remote Similarity NPD8379 Approved
0.656 Remote Similarity NPD6291 Clinical (unspecified phase)
0.656 Remote Similarity NPD8296 Approved
0.656 Remote Similarity NPD8380 Approved
0.656 Remote Similarity NPD8335 Approved
0.656 Remote Similarity NPD8378 Approved
0.6557 Remote Similarity NPD6274 Approved
0.6555 Remote Similarity NPD4634 Approved
0.6538 Remote Similarity NPD4223 Phase 3
0.6538 Remote Similarity NPD4221 Approved
0.6535 Remote Similarity NPD6116 Phase 1
0.6532 Remote Similarity NPD7100 Approved
0.6532 Remote Similarity NPD7101 Approved
0.6522 Remote Similarity NPD7632 Discontinued
0.6522 Remote Similarity NPD5224 Approved
0.6522 Remote Similarity NPD4633 Approved
0.6522 Remote Similarity NPD5225 Approved
0.6522 Remote Similarity NPD5211 Phase 2
0.6522 Remote Similarity NPD5226 Approved
0.6509 Remote Similarity NPD5329 Approved
0.6486 Remote Similarity NPD7748 Approved
0.6481 Remote Similarity NPD5208 Approved
0.6481 Remote Similarity NPD7513 Clinical (unspecified phase)
0.648 Remote Similarity NPD8377 Approved
0.648 Remote Similarity NPD8294 Approved
0.6471 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6466 Remote Similarity NPD5175 Approved
0.6466 Remote Similarity NPD6052 Approved
0.6466 Remote Similarity NPD5174 Approved
0.646 Remote Similarity NPD7902 Approved
0.6455 Remote Similarity NPD6050 Approved
0.6455 Remote Similarity NPD5693 Phase 1
0.6455 Remote Similarity NPD6079 Approved
0.6452 Remote Similarity NPD6335 Approved
0.6449 Remote Similarity NPD7334 Approved
0.6449 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6449 Remote Similarity NPD5330 Approved
0.6449 Remote Similarity NPD6409 Approved
0.6449 Remote Similarity NPD6684 Approved
0.6449 Remote Similarity NPD7146 Approved
0.6449 Remote Similarity NPD7521 Approved
0.6435 Remote Similarity NPD5223 Approved
0.6429 Remote Similarity NPD6921 Approved
0.6429 Remote Similarity NPD6908 Approved
0.6429 Remote Similarity NPD6909 Approved
0.6429 Remote Similarity NPD8033 Approved
0.6422 Remote Similarity NPD4753 Phase 2
0.6415 Remote Similarity NPD4197 Approved
0.641 Remote Similarity NPD5141 Approved
0.64 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6396 Remote Similarity NPD4202 Approved
0.6392 Remote Similarity NPD5360 Phase 3
0.6392 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6389 Remote Similarity NPD3573 Approved
0.6372 Remote Similarity NPD4697 Phase 3
0.6371 Remote Similarity NPD6317 Approved
0.6371 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6364 Remote Similarity NPD5692 Phase 3
0.6364 Remote Similarity NPD6081 Approved
0.6356 Remote Similarity NPD4768 Approved
0.6356 Remote Similarity NPD4767 Approved
0.6337 Remote Similarity NPD3703 Phase 2
0.633 Remote Similarity NPD6672 Approved
0.633 Remote Similarity NPD5737 Approved
0.6328 Remote Similarity NPD6067 Discontinued
0.6328 Remote Similarity NPD8328 Phase 3
0.6325 Remote Similarity NPD4754 Approved
0.632 Remote Similarity NPD6314 Approved
0.632 Remote Similarity NPD6313 Approved
0.6306 Remote Similarity NPD7515 Phase 2
0.6306 Remote Similarity NPD5694 Approved
0.6296 Remote Similarity NPD5205 Approved
0.6296 Remote Similarity NPD4138 Approved
0.6296 Remote Similarity NPD4689 Approved
0.6296 Remote Similarity NPD4688 Approved
0.6296 Remote Similarity NPD3618 Phase 1
0.6296 Remote Similarity NPD4690 Approved
0.6296 Remote Similarity NPD4693 Phase 3
0.6283 Remote Similarity NPD5210 Approved
0.6283 Remote Similarity NPD4629 Approved
0.6262 Remote Similarity NPD4786 Approved
0.625 Remote Similarity NPD5128 Approved
0.625 Remote Similarity NPD4730 Approved
0.625 Remote Similarity NPD4729 Approved
0.6228 Remote Similarity NPD5221 Approved
0.6228 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6228 Remote Similarity NPD5222 Approved
0.62 Remote Similarity NPD5777 Approved
0.6195 Remote Similarity NPD7900 Approved
0.6195 Remote Similarity NPD7901 Clinical (unspecified phase)
0.619 Remote Similarity NPD7525 Registered
0.6186 Remote Similarity NPD4224 Phase 2
0.6174 Remote Similarity NPD5173 Approved
0.616 Remote Similarity NPD6868 Approved
0.6148 Remote Similarity NPD5251 Approved
0.6148 Remote Similarity NPD5247 Approved
0.6148 Remote Similarity NPD5249 Phase 3
0.6148 Remote Similarity NPD5248 Approved
0.6148 Remote Similarity NPD5250 Approved
0.6147 Remote Similarity NPD4694 Approved
0.6147 Remote Similarity NPD5280 Approved
0.6147 Remote Similarity NPD5690 Phase 2
0.6132 Remote Similarity NPD4692 Approved
0.6132 Remote Similarity NPD4139 Approved
0.6121 Remote Similarity NPD4225 Approved

Structure

External Identifiers

PubChem CID   53355687
ChEMBL   CHEMBL1782589
ZINC  

Physicochemical Properties

Molecular Weight:  468.29
ALogP:  1.7881
MLogP:  4.1
XLogP:  4.907
# Rotatable Bonds:  8
Polar Surface Area:  76.13
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  7
# Heavy Atoms:  34

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