Natural Product: NPC9714

Natural Product ID:  NPC9714
Common Name:   Rel-Berkedrimane A
IUPAC Name:   [(5aS,9S,9aS,9bR)-6,6,9a-trimethyl-3-oxo-5,5a,7,8,9,9b-hexahydro-1H-benzo[e][2]benzofuran-9-yl] (2S)-2-acetamido-3-methylbutanoate
Synonyms:   Rel-Berkedrimane A
Molecular Formula:   C22H33NO5
Standard InCHIKey:  HZCZALMQVYCUGC-CXJSAQCFSA-N
Standard InCHI:  InChI=1S/C22H33NO5/c1-12(2)18(23-13(3)24)20(26)28-17-9-10-21(4,5)16-8-7-14-15(22(16,17)6)11-27-19(14)25/h7,12,15-18H,8-11H2,1-6H3,(H,23,24)/t15-,16-,17-,18-,22+/m0/s1
Canonical SMILES:  CC([C@@H](C(=O)O[C@H]1CCC([C@H]2[C@@]1(C)[C@H]1COC(=O)C1=CC2)(C)C)N=C(O)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
NPO17955 Penicillium solitum Species Aspergillaceae Eukaryota PMID[22276851]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT277 Individual Protein Caspase-1 Homo sapiens IC50 = 100000 nM Open TG-GATES in vivo data: Biochemistry
NPT979 Individual Protein Caspase-3 Homo sapiens IC25 = 15 nM 8632413
NPT979 Individual Protein Caspase-3 Homo sapiens IC50 = 200000 nM 18316525

  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 NPC9714 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
0.9145 High Similarity NPC204556
0.8158 Intermediate Similarity NPC189075
0.8158 Intermediate Similarity NPC275539
0.8125 Intermediate Similarity NPC254202
0.807 Intermediate Similarity NPC110496
0.7982 Intermediate Similarity NPC469607
0.7881 Intermediate Similarity NPC194951
0.7881 Intermediate Similarity NPC12046
0.7876 Intermediate Similarity NPC162973
0.7857 Intermediate Similarity NPC471413
0.7851 Intermediate Similarity NPC470276
0.7815 Intermediate Similarity NPC157441
0.7788 Intermediate Similarity NPC471412
0.7778 Intermediate Similarity NPC218602
0.7778 Intermediate Similarity NPC112457
0.7769 Intermediate Similarity NPC470275
0.7768 Intermediate Similarity NPC23364
0.7768 Intermediate Similarity NPC216478
0.7731 Intermediate Similarity NPC269530
0.7727 Intermediate Similarity NPC250075
0.7719 Intermediate Similarity NPC469606
0.7719 Intermediate Similarity NPC31058
0.7719 Intermediate Similarity NPC273005
0.7699 Intermediate Similarity NPC47024
0.7692 Intermediate Similarity NPC89171
0.7692 Intermediate Similarity NPC476802
0.7667 Intermediate Similarity NPC25909
0.7658 Intermediate Similarity NPC183012
0.7636 Intermediate Similarity NPC475657
0.7615 Intermediate Similarity NPC152467
0.7589 Intermediate Similarity NPC29952
0.7586 Intermediate Similarity NPC470297
0.7574 Intermediate Similarity NPC160222
0.7574 Intermediate Similarity NPC193753
0.7568 Intermediate Similarity NPC477130
0.7568 Intermediate Similarity NPC477129
0.7565 Intermediate Similarity NPC476081
0.7563 Intermediate Similarity NPC5103
0.7563 Intermediate Similarity NPC253906
0.7545 Intermediate Similarity NPC186363
0.7545 Intermediate Similarity NPC233345
0.7542 Intermediate Similarity NPC476479
0.7538 Intermediate Similarity NPC90814
0.7538 Intermediate Similarity NPC189393
0.7522 Intermediate Similarity NPC474343
0.7521 Intermediate Similarity NPC478208
0.7521 Intermediate Similarity NPC469454
0.7521 Intermediate Similarity NPC469496
0.7521 Intermediate Similarity NPC469463
0.75 Intermediate Similarity NPC179798
0.75 Intermediate Similarity NPC304180
0.7481 Intermediate Similarity NPC476111
0.748 Intermediate Similarity NPC473968
0.748 Intermediate Similarity NPC147707
0.7479 Intermediate Similarity NPC474243
0.7479 Intermediate Similarity NPC469370
0.7458 Intermediate Similarity NPC133422
0.7455 Intermediate Similarity NPC158488
0.7438 Intermediate Similarity NPC277769
0.7438 Intermediate Similarity NPC476801
0.7436 Intermediate Similarity NPC119329
0.7436 Intermediate Similarity NPC146731
0.7436 Intermediate Similarity NPC118911
0.7431 Intermediate Similarity NPC477128
0.7414 Intermediate Similarity NPC295791
0.7414 Intermediate Similarity NPC165250
0.7414 Intermediate Similarity NPC136289
0.7414 Intermediate Similarity NPC137430
0.7414 Intermediate Similarity NPC58329
0.7411 Intermediate Similarity NPC473434
0.7411 Intermediate Similarity NPC471446
0.7411 Intermediate Similarity NPC474841
0.7411 Intermediate Similarity NPC57117
0.7391 Intermediate Similarity NPC470761
0.7391 Intermediate Similarity NPC476274
0.7391 Intermediate Similarity NPC476933
0.7391 Intermediate Similarity NPC471041
0.7391 Intermediate Similarity NPC473219
0.7387 Intermediate Similarity NPC473944
0.7377 Intermediate Similarity NPC56448
0.7377 Intermediate Similarity NPC471204
0.7373 Intermediate Similarity NPC102352
0.7368 Intermediate Similarity NPC84335
0.7368 Intermediate Similarity NPC70145
0.7368 Intermediate Similarity NPC91695
0.7368 Intermediate Similarity NPC38530
0.7364 Intermediate Similarity NPC73995
0.736 Intermediate Similarity NPC476529
0.736 Intermediate Similarity NPC475775
0.7355 Intermediate Similarity NPC188738
0.7355 Intermediate Similarity NPC469655
0.7355 Intermediate Similarity NPC469656
0.7355 Intermediate Similarity NPC474846
0.735 Intermediate Similarity NPC471365
0.735 Intermediate Similarity NPC471364
0.735 Intermediate Similarity NPC36688
0.735 Intermediate Similarity NPC132395
0.735 Intermediate Similarity NPC8196
0.735 Intermediate Similarity NPC99266
0.735 Intermediate Similarity NPC120321
0.7345 Intermediate Similarity NPC90014
0.7345 Intermediate Similarity NPC259042
0.7345 Intermediate Similarity NPC157686
0.7339 Intermediate Similarity NPC284068
0.7339 Intermediate Similarity NPC98249
0.7339 Intermediate Similarity NPC23046
0.7339 Intermediate Similarity NPC175293
0.7339 Intermediate Similarity NPC469684
0.7339 Intermediate Similarity NPC53396
0.7333 Intermediate Similarity NPC478210
0.7328 Intermediate Similarity NPC476223
0.7328 Intermediate Similarity NPC224720
0.7328 Intermediate Similarity NPC476240
0.7328 Intermediate Similarity NPC81530
0.7317 Intermediate Similarity NPC123117
0.7313 Intermediate Similarity NPC243902
0.7311 Intermediate Similarity NPC144854
0.7311 Intermediate Similarity NPC230541
0.7311 Intermediate Similarity NPC302788
0.7311 Intermediate Similarity NPC67321
0.7311 Intermediate Similarity NPC143609
0.7311 Intermediate Similarity NPC187435
0.7311 Intermediate Similarity NPC3316
0.7311 Intermediate Similarity NPC180744
0.7308 Intermediate Similarity NPC476957
0.7304 Intermediate Similarity NPC476807
0.7304 Intermediate Similarity NPC176845
0.7304 Intermediate Similarity NPC476806
0.7302 Intermediate Similarity NPC109607
0.7302 Intermediate Similarity NPC107338
0.7297 Intermediate Similarity NPC475776
0.7295 Intermediate Similarity NPC90952
0.7295 Intermediate Similarity NPC4573
0.7288 Intermediate Similarity NPC258532
0.7288 Intermediate Similarity NPC96268
0.7288 Intermediate Similarity NPC189616
0.7288 Intermediate Similarity NPC296950
0.7281 Intermediate Similarity NPC234993
0.7281 Intermediate Similarity NPC134072
0.7281 Intermediate Similarity NPC202833
0.7281 Intermediate Similarity NPC228766
0.7281 Intermediate Similarity NPC473964
0.7281 Intermediate Similarity NPC284518
0.7281 Intermediate Similarity NPC165528
0.728 Intermediate Similarity NPC284707
0.7273 Intermediate Similarity NPC472666
0.7273 Intermediate Similarity NPC226863
0.7273 Intermediate Similarity NPC277771
0.7273 Intermediate Similarity NPC478211
0.7273 Intermediate Similarity NPC478209
0.7273 Intermediate Similarity NPC265699
0.7273 Intermediate Similarity NPC215831
0.7265 Intermediate Similarity NPC235369
0.7265 Intermediate Similarity NPC476769
0.7265 Intermediate Similarity NPC164551
0.7265 Intermediate Similarity NPC475320
0.7259 Intermediate Similarity NPC246209
0.7258 Intermediate Similarity NPC176840
0.7258 Intermediate Similarity NPC190286
0.7257 Intermediate Similarity NPC469596
0.7257 Intermediate Similarity NPC225474
0.7257 Intermediate Similarity NPC148000
0.7257 Intermediate Similarity NPC470697
0.725 Intermediate Similarity NPC154608
0.725 Intermediate Similarity NPC277017
0.725 Intermediate Similarity NPC192813
0.7248 Intermediate Similarity NPC220478
0.7241 Intermediate Similarity NPC476299
0.7241 Intermediate Similarity NPC476303
0.7241 Intermediate Similarity NPC474012
0.7236 Intermediate Similarity NPC470120
0.7232 Intermediate Similarity NPC72845
0.7227 Intermediate Similarity NPC127609
0.7227 Intermediate Similarity NPC477125
0.7227 Intermediate Similarity NPC1679
0.7227 Intermediate Similarity NPC34768
0.7227 Intermediate Similarity NPC111952
0.7227 Intermediate Similarity NPC252296
0.7222 Intermediate Similarity NPC469380
0.7222 Intermediate Similarity NPC475599
0.7222 Intermediate Similarity NPC100612
0.7222 Intermediate Similarity NPC187497
0.7222 Intermediate Similarity NPC174336
0.7222 Intermediate Similarity NPC113620
0.7222 Intermediate Similarity NPC475041
0.7217 Intermediate Similarity NPC473963
0.7217 Intermediate Similarity NPC121402
0.7217 Intermediate Similarity NPC285513
0.7217 Intermediate Similarity NPC254496
0.7217 Intermediate Similarity NPC175351
0.7217 Intermediate Similarity NPC151681
0.7217 Intermediate Similarity NPC132753
0.7217 Intermediate Similarity NPC224356
0.7217 Intermediate Similarity NPC474921
0.7213 Intermediate Similarity NPC100329
0.7213 Intermediate Similarity NPC174471
0.7213 Intermediate Similarity NPC132790
0.7213 Intermediate Similarity NPC260786
0.7213 Intermediate Similarity NPC97939
0.7213 Intermediate Similarity NPC247031

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC9714 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
0.7155 Intermediate Similarity NPD7638 Approved
0.7143 Intermediate Similarity NPD7260 Phase 2
0.7109 Intermediate Similarity NPD6909 Approved
0.7109 Intermediate Similarity NPD6908 Approved
0.7094 Intermediate Similarity NPD7640 Approved
0.7094 Intermediate Similarity NPD7639 Approved
0.7083 Intermediate Similarity NPD6008 Approved
0.708 Intermediate Similarity NPD6334 Approved
0.708 Intermediate Similarity NPD6333 Approved
0.7068 Intermediate Similarity NPD6914 Discontinued
0.7 Intermediate Similarity NPD1694 Approved
0.6963 Remote Similarity NPD6845 Suspended
0.6864 Remote Similarity NPD4225 Approved
0.6842 Remote Similarity NPD8074 Phase 3
0.6807 Remote Similarity NPD6404 Discontinued
0.678 Remote Similarity NPD7902 Approved
0.6742 Remote Similarity NPD7604 Phase 2
0.6727 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6724 Remote Similarity NPD6399 Phase 3
0.672 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6694 Remote Similarity NPD6899 Approved
0.6694 Remote Similarity NPD6686 Approved
0.6694 Remote Similarity NPD6881 Approved
0.6667 Remote Similarity NPD6402 Approved
0.6667 Remote Similarity NPD7115 Discovery
0.6667 Remote Similarity NPD6649 Approved
0.6667 Remote Similarity NPD7900 Approved
0.6667 Remote Similarity NPD6650 Approved
0.6667 Remote Similarity NPD7128 Approved
0.6667 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7748 Approved
0.6667 Remote Similarity NPD6675 Approved
0.6667 Remote Similarity NPD5739 Approved
0.664 Remote Similarity NPD6372 Approved
0.664 Remote Similarity NPD6373 Approved
0.664 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6614 Remote Similarity NPD6053 Discontinued
0.6613 Remote Similarity NPD5697 Approved
0.6613 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6587 Remote Similarity NPD6421 Discontinued
0.6587 Remote Similarity NPD6883 Approved
0.6587 Remote Similarity NPD7102 Approved
0.6587 Remote Similarity NPD7290 Approved
0.6562 Remote Similarity NPD4632 Approved
0.656 Remote Similarity NPD7320 Approved
0.656 Remote Similarity NPD6011 Approved
0.6557 Remote Similarity NPD7632 Discontinued
0.6535 Remote Similarity NPD8130 Phase 1
0.6535 Remote Similarity NPD6617 Approved
0.6535 Remote Similarity NPD6847 Approved
0.6535 Remote Similarity NPD6869 Approved
0.6519 Remote Similarity NPD7507 Approved
0.6508 Remote Similarity NPD6013 Approved
0.6508 Remote Similarity NPD6014 Approved
0.6508 Remote Similarity NPD6012 Approved
0.6496 Remote Similarity NPD7515 Phase 2
0.6496 Remote Similarity NPD6079 Approved
0.6484 Remote Similarity NPD6882 Approved
0.6484 Remote Similarity NPD8297 Approved
0.648 Remote Similarity NPD5701 Approved
0.6471 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6466 Remote Similarity NPD5328 Approved
0.6466 Remote Similarity NPD6921 Approved
0.6444 Remote Similarity NPD7492 Approved
0.6441 Remote Similarity NPD5778 Approved
0.6441 Remote Similarity NPD5781 Clinical (unspecified phase)
0.6441 Remote Similarity NPD5779 Approved
0.6435 Remote Similarity NPD3573 Approved
0.6417 Remote Similarity NPD5349 Clinical (unspecified phase)
0.6412 Remote Similarity NPD6009 Approved
0.6406 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6397 Remote Similarity NPD6616 Approved
0.6391 Remote Similarity NPD6319 Approved
0.6391 Remote Similarity NPD6054 Approved
0.6378 Remote Similarity NPD6413 Approved
0.6377 Remote Similarity NPD7319 Approved
0.635 Remote Similarity NPD7078 Approved
0.6348 Remote Similarity NPD6684 Approved
0.6348 Remote Similarity NPD3618 Phase 1
0.6348 Remote Similarity NPD7334 Approved
0.6348 Remote Similarity NPD7146 Approved
0.6348 Remote Similarity NPD5330 Approved
0.6348 Remote Similarity NPD7521 Approved
0.6348 Remote Similarity NPD6409 Approved
0.6343 Remote Similarity NPD5983 Phase 2
0.6333 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6328 Remote Similarity NPD6420 Discontinued
0.6304 Remote Similarity NPD8336 Approved
0.6304 Remote Similarity NPD8337 Approved
0.6304 Remote Similarity NPD7736 Approved
0.6299 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6296 Remote Similarity NPD6370 Approved
0.629 Remote Similarity NPD5211 Phase 2
0.6281 Remote Similarity NPD5221 Approved
0.6281 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6281 Remote Similarity NPD4697 Phase 3
0.6281 Remote Similarity NPD5222 Approved
0.6277 Remote Similarity NPD6336 Discontinued
0.6277 Remote Similarity NPD8451 Approved
0.6271 Remote Similarity NPD46 Approved
0.6271 Remote Similarity NPD6698 Approved
0.627 Remote Similarity NPD5357 Phase 1
0.6269 Remote Similarity NPD6059 Approved
0.626 Remote Similarity NPD5286 Approved
0.626 Remote Similarity NPD5285 Approved
0.626 Remote Similarity NPD4696 Approved
0.626 Remote Similarity NPD6648 Approved
0.625 Remote Similarity NPD7642 Approved
0.625 Remote Similarity NPD7829 Approved
0.625 Remote Similarity NPD8328 Phase 3
0.625 Remote Similarity NPD7830 Approved
0.625 Remote Similarity NPD7122 Discontinued
0.6241 Remote Similarity NPD6335 Approved
0.6241 Remote Similarity NPD7641 Discontinued
0.6241 Remote Similarity NPD8338 Approved
0.624 Remote Similarity NPD2258 Approved
0.624 Remote Similarity NPD2259 Approved
0.6239 Remote Similarity NPD6903 Approved
0.6239 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6239 Remote Similarity NPD6672 Approved
0.6239 Remote Similarity NPD5737 Approved
0.6232 Remote Similarity NPD8448 Approved
0.6232 Remote Similarity NPD8293 Discontinued
0.623 Remote Similarity NPD5173 Approved
0.623 Remote Similarity NPD4755 Approved
0.6224 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6222 Remote Similarity NPD8517 Approved
0.6222 Remote Similarity NPD8513 Phase 3
0.6222 Remote Similarity NPD8515 Approved
0.6222 Remote Similarity NPD8516 Approved
0.6222 Remote Similarity NPD6015 Approved
0.6222 Remote Similarity NPD6016 Approved
0.6222 Remote Similarity NPD6291 Clinical (unspecified phase)
0.622 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6218 Remote Similarity NPD6411 Approved
0.6218 Remote Similarity NPD8035 Phase 2
0.6218 Remote Similarity NPD8034 Phase 2
0.6212 Remote Similarity NPD6274 Approved
0.6212 Remote Similarity NPD6868 Approved
0.621 Remote Similarity NPD5344 Discontinued
0.621 Remote Similarity NPD5223 Approved
0.6202 Remote Similarity NPD6371 Approved
0.6194 Remote Similarity NPD7101 Approved
0.6194 Remote Similarity NPD7100 Approved
0.619 Remote Similarity NPD5141 Approved
0.619 Remote Similarity NPD8407 Phase 2
0.6176 Remote Similarity NPD5988 Approved
0.6165 Remote Similarity NPD7500 Approved
0.6165 Remote Similarity NPD6317 Approved
0.616 Remote Similarity NPD5225 Approved
0.616 Remote Similarity NPD4633 Approved
0.616 Remote Similarity NPD5224 Approved
0.616 Remote Similarity NPD5226 Approved
0.6154 Remote Similarity NPD8415 Approved
0.6134 Remote Similarity NPD5785 Approved
0.6133 Remote Similarity NPD7625 Phase 1
0.6129 Remote Similarity NPD4700 Approved
0.6129 Remote Similarity NPD8418 Phase 2
0.6121 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6119 Remote Similarity NPD6314 Approved
0.6119 Remote Similarity NPD6313 Approved
0.6111 Remote Similarity NPD5174 Approved
0.6111 Remote Similarity NPD5175 Approved
0.6108 Remote Similarity NPD8368 Discontinued
0.6099 Remote Similarity NPD8392 Approved
0.6099 Remote Similarity NPD8391 Approved
0.6099 Remote Similarity NPD8390 Approved
0.6098 Remote Similarity NPD6084 Phase 2
0.6098 Remote Similarity NPD6083 Phase 2
0.6094 Remote Similarity NPD6412 Phase 2
0.6093 Remote Similarity NPD7274 Clinical (unspecified phase)
0.6087 Remote Similarity NPD8299 Approved
0.6087 Remote Similarity NPD8341 Approved
0.6087 Remote Similarity NPD8340 Approved
0.6087 Remote Similarity NPD8342 Approved
0.6083 Remote Similarity NPD5693 Phase 1
0.6077 Remote Similarity NPD4634 Approved
0.6074 Remote Similarity NPD7517 Approved
0.6074 Remote Similarity NPD7519 Approved
0.6074 Remote Similarity NPD7518 Approved
0.6066 Remote Similarity NPD5695 Phase 3
0.6053 Remote Similarity NPD1448 Clinical (unspecified phase)
0.605 Remote Similarity NPD6101 Approved
0.605 Remote Similarity NPD5764 Clinical (unspecified phase)
0.605 Remote Similarity NPD1695 Approved
0.6048 Remote Similarity NPD5696 Approved
0.6045 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6034 Remote Similarity NPD4786 Approved
0.6033 Remote Similarity NPD4202 Approved
0.6031 Remote Similarity NPD1719 Phase 1
0.6016 Remote Similarity NPD7614 Phase 1
0.6016 Remote Similarity NPD6640 Phase 3
0.6016 Remote Similarity NPD4211 Phase 1
0.6016 Remote Similarity NPD7732 Phase 3
0.6 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6 Remote Similarity NPD3667 Approved
0.6 Remote Similarity NPD7327 Approved
0.6 Remote Similarity NPD7328 Approved
0.5985 Remote Similarity NPD7503 Approved
0.5985 Remote Similarity NPD8033 Approved

Structure

External Identifiers

PubChem CID   57333875
ChEMBL   CHEMBL2011679
ZINC  

Physicochemical Properties

Molecular Weight:  391.24
ALogP:  1.2533
MLogP:  3.22
XLogP:  3.997
# Rotatable Bonds:  12
Polar Surface Area:  85.19
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  28

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs