Natural Product: NPC469853

Natural Product ID:  NPC469853
Common Name:   Bulgarialactone D
IUPAC Name:   (9aR)-6-(hydroxymethyl)-3-[(1Z,4E,6E,8E)-1-hydroxy-10-methyl-3-oxododeca-1,4,6,8-tetraenyl]-9a-methyl-4,5,6,8-tetrahydrofuro[3,2-g]isochromene-2,9-dione
Synonyms:   Bulgarialactone D
Molecular Formula:   C26H30O7
Standard InCHIKey:  CKMBMKXIDJMFEL-DMCYUOPFSA-N
Standard InCHI:  InChI=1S/C26H30O7/c1-4-16(2)9-7-5-6-8-10-18(28)13-22(29)23-21-12-17-11-19(14-27)32-15-20(17)24(30)26(21,3)33-25(23)31/h5-10,13,16,19,27,29H,4,11-12,14-15H2,1-3H3/b6-5+,9-7+,10-8+,22-13-/t16?,19?,26-/m1/s1
Canonical SMILES:  CCC(/C=C/C=C/C=C/C(=O)/C=C(/C1=C2CC3=C(C(=O)[C@@]2(OC1=O)C)COC(C3)CO)O)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
NPO32777 bulgaria inquinans icrm-184 Species Bulgariaceae Eukaryota PMID[20655237]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT762 Cell Line A-431 Homo sapiens IC50 = 17600 nM 22801644
NPT397 Cell Line NCI-H460 Homo sapiens IC50 > 50000 nM 23806109
NPT2 Others Unspecified IC50 > 50000 nM 18989978
NPT2 Others Unspecified IC50 > 100000 nM 17194835

  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 NPC469853 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
0.9307 High Similarity NPC469852
0.8911 High Similarity NPC469851
0.8491 Intermediate Similarity NPC266514
0.84 Intermediate Similarity NPC29798
0.84 Intermediate Similarity NPC282644
0.8381 Intermediate Similarity NPC118902
0.8381 Intermediate Similarity NPC104161
0.8381 Intermediate Similarity NPC469980
0.83 Intermediate Similarity NPC193396
0.83 Intermediate Similarity NPC32944
0.83 Intermediate Similarity NPC166110
0.83 Intermediate Similarity NPC32552
0.8286 Intermediate Similarity NPC39996
0.8241 Intermediate Similarity NPC264819
0.8224 Intermediate Similarity NPC477125
0.8218 Intermediate Similarity NPC248193
0.8173 Intermediate Similarity NPC35717
0.8137 Intermediate Similarity NPC121825
0.8108 Intermediate Similarity NPC66108
0.81 Intermediate Similarity NPC95364
0.81 Intermediate Similarity NPC142159
0.8091 Intermediate Similarity NPC89408
0.8077 Intermediate Similarity NPC208094
0.8039 Intermediate Similarity NPC469645
0.8039 Intermediate Similarity NPC469692
0.8037 Intermediate Similarity NPC271059
0.8037 Intermediate Similarity NPC25666
0.8036 Intermediate Similarity NPC321496
0.8019 Intermediate Similarity NPC244456
0.8019 Intermediate Similarity NPC46998
0.8019 Intermediate Similarity NPC110443
0.8019 Intermediate Similarity NPC185141
0.8019 Intermediate Similarity NPC469657
0.8019 Intermediate Similarity NPC128733
0.8019 Intermediate Similarity NPC133907
0.8018 Intermediate Similarity NPC317107
0.8 Intermediate Similarity NPC475065
0.8 Intermediate Similarity NPC38154
0.7982 Intermediate Similarity NPC329048
0.7982 Intermediate Similarity NPC330011
0.798 Intermediate Similarity NPC472009
0.7946 Intermediate Similarity NPC317687
0.7928 Intermediate Similarity NPC29133
0.7925 Intermediate Similarity NPC476299
0.7925 Intermediate Similarity NPC474012
0.7913 Intermediate Similarity NPC186525
0.7913 Intermediate Similarity NPC50774
0.7913 Intermediate Similarity NPC709
0.7909 Intermediate Similarity NPC475418
0.7909 Intermediate Similarity NPC473482
0.7909 Intermediate Similarity NPC318363
0.7905 Intermediate Similarity NPC20066
0.79 Intermediate Similarity NPC472007
0.7895 Intermediate Similarity NPC64318
0.7885 Intermediate Similarity NPC295347
0.7879 Intermediate Similarity NPC187529
0.7876 Intermediate Similarity NPC469454
0.7876 Intermediate Similarity NPC469496
0.7876 Intermediate Similarity NPC469463
0.787 Intermediate Similarity NPC472755
0.7857 Intermediate Similarity NPC324683
0.7857 Intermediate Similarity NPC470961
0.7857 Intermediate Similarity NPC474315
0.7857 Intermediate Similarity NPC179798
0.7857 Intermediate Similarity NPC304180
0.785 Intermediate Similarity NPC471699
0.785 Intermediate Similarity NPC224172
0.785 Intermediate Similarity NPC472753
0.7838 Intermediate Similarity NPC228477
0.7838 Intermediate Similarity NPC137911
0.783 Intermediate Similarity NPC300584
0.783 Intermediate Similarity NPC316598
0.783 Intermediate Similarity NPC161855
0.7826 Intermediate Similarity NPC183580
0.7826 Intermediate Similarity NPC470492
0.7826 Intermediate Similarity NPC140055
0.7826 Intermediate Similarity NPC286528
0.7826 Intermediate Similarity NPC20302
0.7826 Intermediate Similarity NPC312824
0.7826 Intermediate Similarity NPC470493
0.7826 Intermediate Similarity NPC167606
0.7822 Intermediate Similarity NPC472008
0.7818 Intermediate Similarity NPC473284
0.781 Intermediate Similarity NPC473291
0.7807 Intermediate Similarity NPC67259
0.7807 Intermediate Similarity NPC147912
0.78 Intermediate Similarity NPC261721
0.78 Intermediate Similarity NPC291712
0.78 Intermediate Similarity NPC315395
0.78 Intermediate Similarity NPC316426
0.7788 Intermediate Similarity NPC469632
0.7788 Intermediate Similarity NPC191620
0.7778 Intermediate Similarity NPC31641
0.7778 Intermediate Similarity NPC197835
0.7778 Intermediate Similarity NPC473145
0.7778 Intermediate Similarity NPC140591
0.7778 Intermediate Similarity NPC303653
0.7778 Intermediate Similarity NPC474370
0.7778 Intermediate Similarity NPC189609
0.7778 Intermediate Similarity NPC291500
0.7778 Intermediate Similarity NPC476815
0.7778 Intermediate Similarity NPC472754
0.7768 Intermediate Similarity NPC5103
0.7767 Intermediate Similarity NPC142838
0.7748 Intermediate Similarity NPC322903
0.7748 Intermediate Similarity NPC220155
0.7748 Intermediate Similarity NPC327106
0.7745 Intermediate Similarity NPC218927
0.7745 Intermediate Similarity NPC206001
0.7736 Intermediate Similarity NPC471694
0.7736 Intermediate Similarity NPC53844
0.7719 Intermediate Similarity NPC56448
0.7714 Intermediate Similarity NPC471698
0.7714 Intermediate Similarity NPC209355
0.7712 Intermediate Similarity NPC67569
0.7706 Intermediate Similarity NPC159533
0.7706 Intermediate Similarity NPC475945
0.7706 Intermediate Similarity NPC475871
0.7706 Intermediate Similarity NPC473624
0.7706 Intermediate Similarity NPC475050
0.77 Intermediate Similarity NPC281172
0.7692 Intermediate Similarity NPC245320
0.7692 Intermediate Similarity NPC264954
0.7692 Intermediate Similarity NPC115021
0.7685 Intermediate Similarity NPC474339
0.7685 Intermediate Similarity NPC164598
0.7685 Intermediate Similarity NPC472643
0.7677 Intermediate Similarity NPC16488
0.7672 Intermediate Similarity NPC471145
0.7672 Intermediate Similarity NPC243065
0.767 Intermediate Similarity NPC166554
0.767 Intermediate Similarity NPC477684
0.767 Intermediate Similarity NPC475879
0.767 Intermediate Similarity NPC473448
0.767 Intermediate Similarity NPC265856
0.767 Intermediate Similarity NPC471399
0.7667 Intermediate Similarity NPC470922
0.7667 Intermediate Similarity NPC24651
0.7664 Intermediate Similarity NPC306908
0.7658 Intermediate Similarity NPC199107
0.7658 Intermediate Similarity NPC67321
0.7658 Intermediate Similarity NPC232969
0.7658 Intermediate Similarity NPC187435
0.7647 Intermediate Similarity NPC88326
0.7647 Intermediate Similarity NPC23786
0.7647 Intermediate Similarity NPC153700
0.7647 Intermediate Similarity NPC477302
0.7647 Intermediate Similarity NPC470265
0.7647 Intermediate Similarity NPC136879
0.7642 Intermediate Similarity NPC242848
0.7636 Intermediate Similarity NPC296950
0.7636 Intermediate Similarity NPC146731
0.7636 Intermediate Similarity NPC472756
0.7624 Intermediate Similarity NPC469483
0.7615 Intermediate Similarity NPC473596
0.7615 Intermediate Similarity NPC149371
0.7615 Intermediate Similarity NPC474747
0.7607 Intermediate Similarity NPC284707
0.7607 Intermediate Similarity NPC315974
0.7596 Intermediate Similarity NPC327760
0.7596 Intermediate Similarity NPC114345
0.7596 Intermediate Similarity NPC303697
0.7596 Intermediate Similarity NPC303230
0.7596 Intermediate Similarity NPC6099
0.7593 Intermediate Similarity NPC472644
0.7589 Intermediate Similarity NPC151393
0.7586 Intermediate Similarity NPC270478
0.7583 Intermediate Similarity NPC469789
0.7576 Intermediate Similarity NPC474252
0.7573 Intermediate Similarity NPC51358
0.7573 Intermediate Similarity NPC307092
0.757 Intermediate Similarity NPC239895
0.7568 Intermediate Similarity NPC472749
0.7568 Intermediate Similarity NPC472751
0.7568 Intermediate Similarity NPC266570
0.7568 Intermediate Similarity NPC1679
0.7568 Intermediate Similarity NPC472645
0.7565 Intermediate Similarity NPC122056
0.7563 Intermediate Similarity NPC471999
0.7563 Intermediate Similarity NPC472001
0.7563 Intermediate Similarity NPC46570
0.7563 Intermediate Similarity NPC472000
0.7549 Intermediate Similarity NPC23622
0.7547 Intermediate Similarity NPC12727
0.7547 Intermediate Similarity NPC227494
0.7545 Intermediate Similarity NPC472747
0.7545 Intermediate Similarity NPC329345
0.7545 Intermediate Similarity NPC472750
0.7545 Intermediate Similarity NPC72151
0.7545 Intermediate Similarity NPC473283
0.7545 Intermediate Similarity NPC473144
0.7545 Intermediate Similarity NPC297281
0.7545 Intermediate Similarity NPC475526
0.7542 Intermediate Similarity NPC476107
0.7541 Intermediate Similarity NPC476008
0.7541 Intermediate Similarity NPC471940
0.7525 Intermediate Similarity NPC261380
0.7523 Intermediate Similarity NPC47880
0.7523 Intermediate Similarity NPC474742
0.7523 Intermediate Similarity NPC207885

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC469853 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
0.7826 Intermediate Similarity NPD7115 Discovery
0.75 Intermediate Similarity NPD4225 Approved
0.7273 Intermediate Similarity NPD8513 Phase 3
0.7264 Intermediate Similarity NPD7983 Approved
0.7196 Intermediate Similarity NPD5778 Approved
0.7196 Intermediate Similarity NPD5779 Approved
0.7193 Intermediate Similarity NPD5697 Approved
0.719 Intermediate Similarity NPD6319 Approved
0.7179 Intermediate Similarity NPD8297 Approved
0.717 Intermediate Similarity NPD46 Approved
0.717 Intermediate Similarity NPD6698 Approved
0.7131 Intermediate Similarity NPD8516 Approved
0.7131 Intermediate Similarity NPD8515 Approved
0.7131 Intermediate Similarity NPD8517 Approved
0.713 Intermediate Similarity NPD6881 Approved
0.713 Intermediate Similarity NPD6899 Approved
0.7071 Intermediate Similarity NPD4756 Discovery
0.7069 Intermediate Similarity NPD6012 Approved
0.7069 Intermediate Similarity NPD6014 Approved
0.7069 Intermediate Similarity NPD6013 Approved
0.7043 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD7102 Approved
0.7009 Intermediate Similarity NPD6883 Approved
0.7009 Intermediate Similarity NPD5785 Approved
0.7009 Intermediate Similarity NPD6371 Approved
0.7009 Intermediate Similarity NPD7290 Approved
0.7009 Intermediate Similarity NPD7838 Discovery
0.6983 Remote Similarity NPD6011 Approved
0.6957 Remote Similarity NPD5739 Approved
0.6957 Remote Similarity NPD6402 Approved
0.6957 Remote Similarity NPD6675 Approved
0.6957 Remote Similarity NPD7128 Approved
0.6949 Remote Similarity NPD8130 Phase 1
0.6949 Remote Similarity NPD6869 Approved
0.6949 Remote Similarity NPD6617 Approved
0.6949 Remote Similarity NPD6650 Approved
0.6949 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6949 Remote Similarity NPD6649 Approved
0.6949 Remote Similarity NPD6847 Approved
0.6923 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6916 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6916 Remote Similarity NPD6101 Approved
0.6909 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6897 Remote Similarity NPD5701 Approved
0.6891 Remote Similarity NPD6882 Approved
0.6857 Remote Similarity NPD5363 Approved
0.685 Remote Similarity NPD8074 Phase 3
0.6842 Remote Similarity NPD5211 Phase 2
0.6838 Remote Similarity NPD7320 Approved
0.6838 Remote Similarity NPD6686 Approved
0.6833 Remote Similarity NPD4632 Approved
0.6827 Remote Similarity NPD7154 Phase 3
0.6825 Remote Similarity NPD7492 Approved
0.6789 Remote Similarity NPD6411 Approved
0.6786 Remote Similarity NPD6083 Phase 2
0.6786 Remote Similarity NPD6084 Phase 2
0.678 Remote Similarity NPD6372 Approved
0.678 Remote Similarity NPD6373 Approved
0.6774 Remote Similarity NPD6054 Approved
0.6772 Remote Similarity NPD6616 Approved
0.6757 Remote Similarity NPD5695 Phase 3
0.6754 Remote Similarity NPD5344 Discontinued
0.675 Remote Similarity NPD6053 Discontinued
0.6724 Remote Similarity NPD5141 Approved
0.6723 Remote Similarity NPD4634 Approved
0.672 Remote Similarity NPD6016 Approved
0.672 Remote Similarity NPD6015 Approved
0.6719 Remote Similarity NPD7078 Approved
0.6698 Remote Similarity NPD1694 Approved
0.6698 Remote Similarity NPD1696 Phase 3
0.6695 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5286 Approved
0.6667 Remote Similarity NPD4696 Approved
0.6667 Remote Similarity NPD5282 Discontinued
0.6667 Remote Similarity NPD6009 Approved
0.6667 Remote Similarity NPD6648 Approved
0.6667 Remote Similarity NPD6370 Approved
0.6667 Remote Similarity NPD5285 Approved
0.6667 Remote Similarity NPD5988 Approved
0.6667 Remote Similarity NPD7736 Approved
0.6604 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6587 Remote Similarity NPD7503 Approved
0.6587 Remote Similarity NPD5983 Phase 2
0.6585 Remote Similarity NPD6274 Approved
0.6583 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6579 Remote Similarity NPD5696 Approved
0.6571 Remote Similarity NPD5209 Approved
0.6571 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6571 Remote Similarity NPD4270 Approved
0.6571 Remote Similarity NPD4269 Approved
0.656 Remote Similarity NPD7100 Approved
0.656 Remote Similarity NPD7101 Approved
0.6552 Remote Similarity NPD5226 Approved
0.6552 Remote Similarity NPD4633 Approved
0.6552 Remote Similarity NPD5224 Approved
0.6552 Remote Similarity NPD5225 Approved
0.6549 Remote Similarity NPD7839 Suspended
0.6538 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6532 Remote Similarity NPD6317 Approved
0.6529 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6522 Remote Similarity NPD7640 Approved
0.6522 Remote Similarity NPD7639 Approved
0.6515 Remote Similarity NPD7260 Phase 2
0.6508 Remote Similarity NPD6059 Approved
0.6496 Remote Similarity NPD5174 Approved
0.6496 Remote Similarity NPD5175 Approved
0.6491 Remote Similarity NPD4755 Approved
0.6489 Remote Similarity NPD7319 Approved
0.6486 Remote Similarity NPD7637 Suspended
0.6486 Remote Similarity NPD5693 Phase 1
0.6486 Remote Similarity NPD5694 Approved
0.6484 Remote Similarity NPD7604 Phase 2
0.6484 Remote Similarity NPD8328 Phase 3
0.6481 Remote Similarity NPD5786 Approved
0.648 Remote Similarity NPD6335 Approved
0.648 Remote Similarity NPD6313 Approved
0.648 Remote Similarity NPD6314 Approved
0.6476 Remote Similarity NPD5369 Approved
0.6466 Remote Similarity NPD5223 Approved
0.6462 Remote Similarity NPD8293 Discontinued
0.6446 Remote Similarity NPD2067 Discontinued
0.6435 Remote Similarity NPD7638 Approved
0.6429 Remote Similarity NPD6399 Phase 3
0.6404 Remote Similarity NPD5222 Approved
0.6404 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6404 Remote Similarity NPD5221 Approved
0.6397 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6396 Remote Similarity NPD5692 Phase 3
0.6393 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6385 Remote Similarity NPD6336 Discontinued
0.6385 Remote Similarity NPD7507 Approved
0.6381 Remote Similarity NPD4821 Approved
0.6381 Remote Similarity NPD4252 Approved
0.6381 Remote Similarity NPD4820 Approved
0.6381 Remote Similarity NPD4819 Approved
0.6381 Remote Similarity NPD4822 Approved
0.6381 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6379 Remote Similarity NPD4700 Approved
0.6378 Remote Similarity NPD7299 Clinical (unspecified phase)
0.6372 Remote Similarity NPD7748 Approved
0.6364 Remote Similarity NPD5737 Approved
0.6364 Remote Similarity NPD6672 Approved
0.6357 Remote Similarity NPD7830 Approved
0.6357 Remote Similarity NPD7829 Approved
0.6355 Remote Similarity NPD6110 Phase 1
0.6355 Remote Similarity NPD5362 Discontinued
0.6348 Remote Similarity NPD5173 Approved
0.6348 Remote Similarity NPD7902 Approved
0.6339 Remote Similarity NPD7515 Phase 2
0.6339 Remote Similarity NPD5281 Approved
0.6339 Remote Similarity NPD5284 Approved
0.6339 Remote Similarity NPD6050 Approved
0.6333 Remote Similarity NPD5954 Clinical (unspecified phase)
0.633 Remote Similarity NPD5279 Phase 3
0.632 Remote Similarity NPD690 Clinical (unspecified phase)
0.632 Remote Similarity NPD6868 Approved
0.6316 Remote Similarity NPD5210 Approved
0.6316 Remote Similarity NPD4629 Approved
0.6306 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6306 Remote Similarity NPD4753 Phase 2
0.6281 Remote Similarity NPD4730 Approved
0.6281 Remote Similarity NPD4729 Approved
0.627 Remote Similarity NPD7500 Approved
0.6262 Remote Similarity NPD6435 Approved
0.6239 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6226 Remote Similarity NPD4695 Discontinued
0.6214 Remote Similarity NPD8039 Approved
0.6202 Remote Similarity NPD6908 Approved
0.6202 Remote Similarity NPD6909 Approved
0.6202 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6198 Remote Similarity NPD6412 Phase 2
0.6195 Remote Similarity NPD6079 Approved
0.619 Remote Similarity NPD5784 Clinical (unspecified phase)
0.619 Remote Similarity NPD2629 Approved
0.619 Remote Similarity NPD4271 Approved
0.619 Remote Similarity NPD4268 Approved
0.6182 Remote Similarity NPD3618 Phase 1
0.6182 Remote Similarity NPD4249 Approved
0.6179 Remote Similarity NPD5251 Approved
0.6179 Remote Similarity NPD5249 Phase 3
0.6179 Remote Similarity NPD5248 Approved
0.6179 Remote Similarity NPD5250 Approved
0.6179 Remote Similarity NPD5247 Approved
0.6161 Remote Similarity NPD6080 Approved
0.6161 Remote Similarity NPD6673 Approved
0.6161 Remote Similarity NPD6904 Approved
0.6154 Remote Similarity NPD8080 Discontinued
0.6148 Remote Similarity NPD5128 Approved
0.6142 Remote Similarity NPD8295 Clinical (unspecified phase)
0.614 Remote Similarity NPD4202 Approved
0.6138 Remote Similarity NPD7236 Approved
0.6136 Remote Similarity NPD8273 Phase 1
0.6129 Remote Similarity NPD5216 Approved
0.6129 Remote Similarity NPD7601 Clinical (unspecified phase)
0.6129 Remote Similarity NPD5215 Approved
0.6129 Remote Similarity NPD5217 Approved
0.6126 Remote Similarity NPD3573 Approved
0.6126 Remote Similarity NPD4251 Approved
0.6126 Remote Similarity NPD4250 Approved

Structure

External Identifiers

PubChem CID   49864118
ChEMBL   CHEMBL1215389
ZINC  

Physicochemical Properties

Molecular Weight:  454.20
ALogP:  0.5575
MLogP:  3.55
XLogP:  2.646
# Rotatable Bonds:  13
Polar Surface Area:  110.13
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  33

Download Data

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