Natural Product: NPC325769

Natural Product ID:  NPC325769
Common Name:   Berkeleydione
IUPAC Name:  
Synonyms:   Berkeleydione
Molecular Formula:   C26H32O7
Standard InCHIKey:  RBGYOLFHIDJTOX-VMXKAMJHSA-N
Standard InCHI:  InChI=1S/C26H32O7/c1-13-15-11-18(27)33-22(3,4)16(15)9-10-24(6)17(13)12-23(5)14(2)26(24,21(30)32-8)20(29)25(7,31)19(23)28/h9,17,31H,2,10-12H2,1,3-8H3/t17-,23+,24-,25-,26-/m0/s1
Canonical SMILES:  COC(=O)[C@@]12C(=O)[C@@](C)(O)C(=O)[C@](C1=C)(C)C[C@@H]1[C@]2(C)CC=C2C(=C1C)CC(=O)OC2(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
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota Berkeley Pit lake PMID[17970594]
NPO29761 Penicillium rubrum Species Trichocomaceae Eukaryota PMID[21916432]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT277 Individual Protein Caspase-1 Homo sapiens Inhibition = 89 % 21916432
NPT5270 Individual Protein Interleukin-1 beta Homo sapiens IC50 = 4400 nM 21916432

  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 NPC325769 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
0.9286 High Similarity NPC323441
0.8878 High Similarity NPC269492
0.8469 Intermediate Similarity NPC327515
0.8182 Intermediate Similarity NPC263977
0.8037 Intermediate Similarity NPC85529
0.8037 Intermediate Similarity NPC32006
0.785 Intermediate Similarity NPC90177
0.7826 Intermediate Similarity NPC158963
0.7822 Intermediate Similarity NPC476369
0.7822 Intermediate Similarity NPC476437
0.7788 Intermediate Similarity NPC223169
0.7768 Intermediate Similarity NPC193948
0.7767 Intermediate Similarity NPC476415
0.7757 Intermediate Similarity NPC80781
0.7745 Intermediate Similarity NPC45579
0.7736 Intermediate Similarity NPC46761
0.7714 Intermediate Similarity NPC170131
0.7706 Intermediate Similarity NPC292588
0.77 Intermediate Similarity NPC231599
0.7699 Intermediate Similarity NPC159333
0.7692 Intermediate Similarity NPC777
0.7664 Intermediate Similarity NPC474899
0.7664 Intermediate Similarity NPC474912
0.7658 Intermediate Similarity NPC220705
0.7642 Intermediate Similarity NPC316598
0.7636 Intermediate Similarity NPC475294
0.7636 Intermediate Similarity NPC473169
0.7615 Intermediate Similarity NPC476001
0.7615 Intermediate Similarity NPC474898
0.7615 Intermediate Similarity NPC213366
0.7611 Intermediate Similarity NPC147180
0.757 Intermediate Similarity NPC117685
0.757 Intermediate Similarity NPC474802
0.7549 Intermediate Similarity NPC284561
0.7547 Intermediate Similarity NPC285513
0.7547 Intermediate Similarity NPC254496
0.7545 Intermediate Similarity NPC1679
0.7544 Intermediate Similarity NPC474271
0.7524 Intermediate Similarity NPC295347
0.7524 Intermediate Similarity NPC209355
0.7523 Intermediate Similarity NPC275583
0.7523 Intermediate Similarity NPC25666
0.7523 Intermediate Similarity NPC271059
0.75 Intermediate Similarity NPC474327
0.75 Intermediate Similarity NPC239273
0.75 Intermediate Similarity NPC271652
0.75 Intermediate Similarity NPC76333
0.75 Intermediate Similarity NPC476416
0.75 Intermediate Similarity NPC472685
0.75 Intermediate Similarity NPC131840
0.75 Intermediate Similarity NPC228477
0.75 Intermediate Similarity NPC472702
0.75 Intermediate Similarity NPC137911
0.7456 Intermediate Similarity NPC4573
0.7456 Intermediate Similarity NPC277769
0.7456 Intermediate Similarity NPC269530
0.7456 Intermediate Similarity NPC475524
0.7456 Intermediate Similarity NPC264634
0.7456 Intermediate Similarity NPC100267
0.7455 Intermediate Similarity NPC284865
0.7455 Intermediate Similarity NPC239162
0.7451 Intermediate Similarity NPC24816
0.7449 Intermediate Similarity NPC229584
0.7449 Intermediate Similarity NPC14203
0.7438 Intermediate Similarity NPC181999
0.7434 Intermediate Similarity NPC470496
0.7434 Intermediate Similarity NPC478209
0.7431 Intermediate Similarity NPC475091
0.7431 Intermediate Similarity NPC136289
0.7429 Intermediate Similarity NPC148964
0.7429 Intermediate Similarity NPC293086
0.7429 Intermediate Similarity NPC84893
0.7423 Intermediate Similarity NPC28319
0.7417 Intermediate Similarity NPC91693
0.7417 Intermediate Similarity NPC265557
0.7417 Intermediate Similarity NPC67251
0.7417 Intermediate Similarity NPC18945
0.7417 Intermediate Similarity NPC105926
0.7411 Intermediate Similarity NPC473482
0.7411 Intermediate Similarity NPC208461
0.7411 Intermediate Similarity NPC475418
0.7411 Intermediate Similarity NPC289702
0.7411 Intermediate Similarity NPC322903
0.7411 Intermediate Similarity NPC168883
0.7411 Intermediate Similarity NPC318363
0.7407 Intermediate Similarity NPC174314
0.7407 Intermediate Similarity NPC477521
0.7407 Intermediate Similarity NPC476933
0.7404 Intermediate Similarity NPC470036
0.7404 Intermediate Similarity NPC174167
0.7404 Intermediate Similarity NPC36491
0.7398 Intermediate Similarity NPC476854
0.7395 Intermediate Similarity NPC470779
0.7391 Intermediate Similarity NPC472929
0.7391 Intermediate Similarity NPC471204
0.7387 Intermediate Similarity NPC478208
0.7387 Intermediate Similarity NPC478052
0.7387 Intermediate Similarity NPC469607
0.7387 Intermediate Similarity NPC477125
0.7383 Intermediate Similarity NPC84335
0.7383 Intermediate Similarity NPC38530
0.7383 Intermediate Similarity NPC208094
0.7383 Intermediate Similarity NPC474343
0.7379 Intermediate Similarity NPC36668
0.7379 Intermediate Similarity NPC118011
0.7379 Intermediate Similarity NPC474700
0.7368 Intermediate Similarity NPC34315
0.7368 Intermediate Similarity NPC470246
0.7368 Intermediate Similarity NPC474315
0.7368 Intermediate Similarity NPC96739
0.7368 Intermediate Similarity NPC260786
0.7368 Intermediate Similarity NPC474871
0.7368 Intermediate Similarity NPC174471
0.7364 Intermediate Similarity NPC194323
0.7364 Intermediate Similarity NPC329345
0.7364 Intermediate Similarity NPC473283
0.7364 Intermediate Similarity NPC179208
0.7364 Intermediate Similarity NPC475526
0.7358 Intermediate Similarity NPC134067
0.7358 Intermediate Similarity NPC217329
0.7355 Intermediate Similarity NPC24651
0.7355 Intermediate Similarity NPC476729
0.7353 Intermediate Similarity NPC477228
0.7353 Intermediate Similarity NPC476409
0.7353 Intermediate Similarity NPC171722
0.735 Intermediate Similarity NPC476959
0.735 Intermediate Similarity NPC472934
0.735 Intermediate Similarity NPC473590
0.7345 Intermediate Similarity NPC300026
0.7345 Intermediate Similarity NPC475065
0.7339 Intermediate Similarity NPC472643
0.7339 Intermediate Similarity NPC81530
0.7339 Intermediate Similarity NPC206079
0.7339 Intermediate Similarity NPC476888
0.7339 Intermediate Similarity NPC93744
0.7339 Intermediate Similarity NPC476855
0.7339 Intermediate Similarity NPC472637
0.7333 Intermediate Similarity NPC477435
0.7333 Intermediate Similarity NPC312833
0.7333 Intermediate Similarity NPC477436
0.7333 Intermediate Similarity NPC199543
0.7333 Intermediate Similarity NPC263780
0.7333 Intermediate Similarity NPC169343
0.7327 Intermediate Similarity NPC474680
0.7321 Intermediate Similarity NPC112780
0.7321 Intermediate Similarity NPC329048
0.7321 Intermediate Similarity NPC476958
0.7321 Intermediate Similarity NPC330011
0.7317 Intermediate Similarity NPC476859
0.7315 Intermediate Similarity NPC64742
0.7315 Intermediate Similarity NPC176845
0.7311 Intermediate Similarity NPC476962
0.7308 Intermediate Similarity NPC214844
0.7308 Intermediate Similarity NPC253177
0.7308 Intermediate Similarity NPC316228
0.7308 Intermediate Similarity NPC213636
0.7308 Intermediate Similarity NPC51486
0.7308 Intermediate Similarity NPC280592
0.7308 Intermediate Similarity NPC113393
0.7308 Intermediate Similarity NPC198818
0.7304 Intermediate Similarity NPC215643
0.7304 Intermediate Similarity NPC170212
0.7304 Intermediate Similarity NPC475391
0.7304 Intermediate Similarity NPC285956
0.7304 Intermediate Similarity NPC476163
0.7304 Intermediate Similarity NPC265499
0.7304 Intermediate Similarity NPC90952
0.7304 Intermediate Similarity NPC89227
0.7304 Intermediate Similarity NPC101825
0.7304 Intermediate Similarity NPC17138
0.7304 Intermediate Similarity NPC40608
0.7304 Intermediate Similarity NPC221511
0.7304 Intermediate Similarity NPC151216
0.7304 Intermediate Similarity NPC265391
0.7297 Intermediate Similarity NPC309190
0.7297 Intermediate Similarity NPC472868
0.7297 Intermediate Similarity NPC118911
0.7297 Intermediate Similarity NPC473175
0.7295 Intermediate Similarity NPC477745
0.729 Intermediate Similarity NPC469528
0.729 Intermediate Similarity NPC29952
0.729 Intermediate Similarity NPC62516
0.729 Intermediate Similarity NPC476797
0.729 Intermediate Similarity NPC157113
0.729 Intermediate Similarity NPC469369
0.7288 Intermediate Similarity NPC472760
0.7288 Intermediate Similarity NPC470776
0.7288 Intermediate Similarity NPC251310
0.7288 Intermediate Similarity NPC21326
0.7282 Intermediate Similarity NPC72397
0.7282 Intermediate Similarity NPC124927
0.7282 Intermediate Similarity NPC475101
0.7282 Intermediate Similarity NPC476427
0.7281 Intermediate Similarity NPC272898
0.7281 Intermediate Similarity NPC473036
0.7273 Intermediate Similarity NPC474955
0.7273 Intermediate Similarity NPC40918
0.7273 Intermediate Similarity NPC476890
0.7273 Intermediate Similarity NPC162973
0.7273 Intermediate Similarity NPC273005

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC325769 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
0.7411 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7404 Intermediate Similarity NPD6411 Approved
0.7212 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD6101 Approved
0.717 Intermediate Similarity NPD6399 Phase 3
0.7156 Intermediate Similarity NPD5696 Approved
0.708 Intermediate Similarity NPD6675 Approved
0.708 Intermediate Similarity NPD6402 Approved
0.708 Intermediate Similarity NPD5739 Approved
0.708 Intermediate Similarity NPD7128 Approved
0.7043 Intermediate Similarity NPD6372 Approved
0.7043 Intermediate Similarity NPD6373 Approved
0.7009 Intermediate Similarity NPD5779 Approved
0.7009 Intermediate Similarity NPD5778 Approved
0.6957 Remote Similarity NPD6881 Approved
0.6957 Remote Similarity NPD6899 Approved
0.6957 Remote Similarity NPD7320 Approved
0.6923 Remote Similarity NPD6650 Approved
0.6923 Remote Similarity NPD6649 Approved
0.6917 Remote Similarity NPD7115 Discovery
0.6916 Remote Similarity NPD5693 Phase 1
0.6909 Remote Similarity NPD7902 Approved
0.6909 Remote Similarity NPD6083 Phase 2
0.6909 Remote Similarity NPD6084 Phase 2
0.687 Remote Similarity NPD5701 Approved
0.687 Remote Similarity NPD5697 Approved
0.6857 Remote Similarity NPD3573 Approved
0.6838 Remote Similarity NPD7102 Approved
0.6838 Remote Similarity NPD6883 Approved
0.6838 Remote Similarity NPD7290 Approved
0.681 Remote Similarity NPD6011 Approved
0.6792 Remote Similarity NPD5737 Approved
0.6792 Remote Similarity NPD6672 Approved
0.6789 Remote Similarity NPD7748 Approved
0.678 Remote Similarity NPD6847 Approved
0.678 Remote Similarity NPD6869 Approved
0.678 Remote Similarity NPD6401 Clinical (unspecified phase)
0.678 Remote Similarity NPD8130 Phase 1
0.678 Remote Similarity NPD6617 Approved
0.6762 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6762 Remote Similarity NPD6098 Approved
0.6759 Remote Similarity NPD6050 Approved
0.6759 Remote Similarity NPD5281 Approved
0.6759 Remote Similarity NPD5284 Approved
0.6752 Remote Similarity NPD6014 Approved
0.6752 Remote Similarity NPD6013 Approved
0.6752 Remote Similarity NPD6012 Approved
0.6744 Remote Similarity NPD7260 Phase 2
0.6729 Remote Similarity NPD6673 Approved
0.6729 Remote Similarity NPD6904 Approved
0.6729 Remote Similarity NPD6080 Approved
0.6727 Remote Similarity NPD5695 Phase 3
0.6727 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6723 Remote Similarity NPD6882 Approved
0.6723 Remote Similarity NPD8297 Approved
0.6699 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6696 Remote Similarity NPD7638 Approved
0.6696 Remote Similarity NPD4225 Approved
0.6694 Remote Similarity NPD6921 Approved
0.6667 Remote Similarity NPD5692 Phase 3
0.6667 Remote Similarity NPD4695 Discontinued
0.6639 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6637 Remote Similarity NPD7640 Approved
0.6637 Remote Similarity NPD7639 Approved
0.6636 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6636 Remote Similarity NPD7900 Approved
0.6607 Remote Similarity NPD4755 Approved
0.6606 Remote Similarity NPD7515 Phase 2
0.6606 Remote Similarity NPD5694 Approved
0.6587 Remote Similarity NPD8328 Phase 3
0.6577 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6577 Remote Similarity NPD4629 Approved
0.6577 Remote Similarity NPD5210 Approved
0.6565 Remote Similarity NPD6845 Suspended
0.6525 Remote Similarity NPD6686 Approved
0.6522 Remote Similarity NPD5211 Phase 2
0.6518 Remote Similarity NPD4697 Phase 3
0.6518 Remote Similarity NPD7614 Phase 1
0.6509 Remote Similarity NPD1694 Approved
0.6509 Remote Similarity NPD5329 Approved
0.6496 Remote Similarity NPD6008 Approved
0.6491 Remote Similarity NPD4696 Approved
0.6491 Remote Similarity NPD5285 Approved
0.6491 Remote Similarity NPD4700 Approved
0.6491 Remote Similarity NPD5286 Approved
0.648 Remote Similarity NPD6319 Approved
0.6462 Remote Similarity NPD7319 Approved
0.6455 Remote Similarity NPD8035 Phase 2
0.6455 Remote Similarity NPD7637 Suspended
0.6455 Remote Similarity NPD8034 Phase 2
0.6452 Remote Similarity NPD6335 Approved
0.6449 Remote Similarity NPD7334 Approved
0.6449 Remote Similarity NPD5330 Approved
0.6449 Remote Similarity NPD5280 Approved
0.6449 Remote Similarity NPD6409 Approved
0.6449 Remote Similarity NPD7146 Approved
0.6449 Remote Similarity NPD7521 Approved
0.6449 Remote Similarity NPD4694 Approved
0.6449 Remote Similarity NPD6684 Approved
0.6446 Remote Similarity NPD6053 Discontinued
0.6435 Remote Similarity NPD5223 Approved
0.6429 Remote Similarity NPD5654 Approved
0.6429 Remote Similarity NPD8517 Approved
0.6429 Remote Similarity NPD8516 Approved
0.6429 Remote Similarity NPD8513 Phase 3
0.6429 Remote Similarity NPD8515 Approved
0.6423 Remote Similarity NPD6274 Approved
0.6422 Remote Similarity NPD4753 Phase 2
0.6422 Remote Similarity NPD5328 Approved
0.6417 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6417 Remote Similarity NPD6371 Approved
0.6415 Remote Similarity NPD4197 Approved
0.6415 Remote Similarity NPD4786 Approved
0.641 Remote Similarity NPD5141 Approved
0.6406 Remote Similarity NPD7492 Approved
0.64 Remote Similarity NPD7101 Approved
0.64 Remote Similarity NPD7100 Approved
0.6393 Remote Similarity NPD4632 Approved
0.6381 Remote Similarity NPD3667 Approved
0.6379 Remote Similarity NPD4633 Approved
0.6379 Remote Similarity NPD5225 Approved
0.6379 Remote Similarity NPD5226 Approved
0.6379 Remote Similarity NPD5224 Approved
0.6372 Remote Similarity NPD5222 Approved
0.6372 Remote Similarity NPD5221 Approved
0.6372 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6372 Remote Similarity NPD7732 Phase 3
0.6371 Remote Similarity NPD6317 Approved
0.6364 Remote Similarity NPD5785 Approved
0.6364 Remote Similarity NPD5207 Approved
0.6357 Remote Similarity NPD7507 Approved
0.6357 Remote Similarity NPD6616 Approved
0.6349 Remote Similarity NPD6059 Approved
0.6349 Remote Similarity NPD6054 Approved
0.6339 Remote Similarity NPD5282 Discontinued
0.6337 Remote Similarity NPD8039 Approved
0.6333 Remote Similarity NPD4061 Clinical (unspecified phase)
0.633 Remote Similarity NPD7513 Clinical (unspecified phase)
0.633 Remote Similarity NPD6903 Approved
0.6325 Remote Similarity NPD5175 Approved
0.6325 Remote Similarity NPD4754 Approved
0.6325 Remote Similarity NPD5174 Approved
0.632 Remote Similarity NPD6313 Approved
0.632 Remote Similarity NPD6314 Approved
0.6316 Remote Similarity NPD5173 Approved
0.6316 Remote Similarity NPD5959 Approved
0.6311 Remote Similarity NPD3617 Approved
0.6308 Remote Similarity NPD7078 Approved
0.6308 Remote Similarity NPD8293 Discontinued
0.6306 Remote Similarity NPD7983 Approved
0.6306 Remote Similarity NPD6079 Approved
0.6303 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6303 Remote Similarity NPD6614 Approved
0.6299 Remote Similarity NPD6909 Approved
0.6299 Remote Similarity NPD6908 Approved
0.6299 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6296 Remote Similarity NPD4623 Approved
0.6296 Remote Similarity NPD5786 Approved
0.6296 Remote Similarity NPD5279 Phase 3
0.6296 Remote Similarity NPD4519 Discontinued
0.6296 Remote Similarity NPD3618 Phase 1
0.629 Remote Similarity NPD6868 Approved
0.6281 Remote Similarity NPD4634 Approved
0.6273 Remote Similarity NPD6051 Approved
0.626 Remote Similarity NPD7736 Approved
0.625 Remote Similarity NPD6370 Approved
0.624 Remote Similarity NPD6009 Approved
0.6239 Remote Similarity NPD7632 Discontinued
0.6228 Remote Similarity NPD7839 Suspended
0.6226 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6226 Remote Similarity NPD4223 Phase 3
0.6226 Remote Similarity NPD4221 Approved
0.6218 Remote Similarity NPD4767 Approved
0.6218 Remote Similarity NPD4768 Approved
0.6204 Remote Similarity NPD1696 Phase 3
0.6202 Remote Similarity NPD7604 Phase 2
0.6198 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6195 Remote Similarity NPD6001 Approved
0.6183 Remote Similarity NPD8074 Phase 3
0.6182 Remote Similarity NPD5208 Approved
0.6172 Remote Similarity NPD5983 Phase 2
0.6172 Remote Similarity NPD6015 Approved
0.6172 Remote Similarity NPD6016 Approved
0.6167 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6147 Remote Similarity NPD5690 Phase 2
0.6132 Remote Similarity NPD5369 Approved
0.6124 Remote Similarity NPD5988 Approved
0.6116 Remote Similarity NPD4729 Approved
0.6116 Remote Similarity NPD4730 Approved
0.6116 Remote Similarity NPD5128 Approved
0.6111 Remote Similarity NPD3666 Approved
0.6111 Remote Similarity NPD3665 Phase 1
0.6111 Remote Similarity NPD3668 Phase 3
0.6111 Remote Similarity NPD3133 Approved
0.6107 Remote Similarity NPD6336 Discontinued
0.6106 Remote Similarity NPD5133 Approved
0.6106 Remote Similarity NPD4202 Approved
0.6102 Remote Similarity NPD5091 Approved
0.6098 Remote Similarity NPD8413 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   21580417
ChEMBL   CHEMBL400514
ZINC  

Physicochemical Properties

Molecular Weight:  456.21
ALogP:  1.9045
MLogP:  3.55
XLogP:  2.768
# Rotatable Bonds:  10
Polar Surface Area:  106.97
# H-Bond Aceptor:  7
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  33

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
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