Natural Product: NPC477680

Natural Product ID:  NPC477680
Common Name:   Berkeleyamide D
IUPAC Name:   2-benzyl-8,9-dihydroxy-8-(2-methylpropyl)-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
Synonyms:   Berkeleyamide D
Molecular Formula:   C18H21NO5
Standard InCHIKey:  KYPWBBBOBAOGSQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C18H21NO5/c1-11(2)10-17(23)15(21)18(16(22)19-17)14(20)9-13(24-18)8-12-6-4-3-5-7-12/h3-7,9,11,15,21,23H,8,10H2,1-2H3,(H,19,22)
Canonical SMILES:  CC(CC1(O)N=C(C2(C1O)OC(=CC2=O)Cc1ccccc1)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
NPO29761 Penicillium rubrum Species Trichocomaceae Eukaryota Berkeley Pit Lake, Butte, Montana PMID[18330993]

  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 = 610 nM 18330993
NPT567 Individual Protein Matrix metalloproteinase 3 Homo sapiens IC50 = 610 nM 18330993

  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 NPC477680 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
0.8986 High Similarity NPC339338
0.8986 High Similarity NPC227905
0.8986 High Similarity NPC146097
0.8857 High Similarity NPC185404
0.771 Intermediate Similarity NPC188010
0.7594 Intermediate Similarity NPC471553
0.7431 Intermediate Similarity NPC279045
0.7431 Intermediate Similarity NPC113325
0.7383 Intermediate Similarity NPC49565
0.7379 Intermediate Similarity NPC208725
0.7361 Intermediate Similarity NPC228511
0.7279 Intermediate Similarity NPC471201
0.7273 Intermediate Similarity NPC183722
0.726 Intermediate Similarity NPC175870
0.7254 Intermediate Similarity NPC116057
0.7211 Intermediate Similarity NPC473055
0.7211 Intermediate Similarity NPC473052
0.7183 Intermediate Similarity NPC81135
0.7174 Intermediate Similarity NPC478016
0.7174 Intermediate Similarity NPC478015
0.7174 Intermediate Similarity NPC478014
0.7172 Intermediate Similarity NPC328070
0.7162 Intermediate Similarity NPC322526
0.7143 Intermediate Similarity NPC162104
0.7133 Intermediate Similarity NPC472413
0.7097 Intermediate Similarity NPC4108
0.7076 Intermediate Similarity NPC471395
0.7067 Intermediate Similarity NPC108852
0.7067 Intermediate Similarity NPC261709
0.7067 Intermediate Similarity NPC111586
0.705 Intermediate Similarity NPC105709
0.7044 Intermediate Similarity NPC476194
0.7021 Intermediate Similarity NPC472415
0.7014 Intermediate Similarity NPC71271
0.7 Intermediate Similarity NPC19136
0.6993 Remote Similarity NPC236405
0.6986 Remote Similarity NPC42423
0.6934 Remote Similarity NPC235421
0.6929 Remote Similarity NPC190663
0.6929 Remote Similarity NPC80150
0.6923 Remote Similarity NPC47667
0.6917 Remote Similarity NPC475282
0.6912 Remote Similarity NPC474544
0.6912 Remote Similarity NPC1986
0.6906 Remote Similarity NPC237420
0.6906 Remote Similarity NPC310467
0.6906 Remote Similarity NPC314992
0.6901 Remote Similarity NPC35996
0.6892 Remote Similarity NPC144257
0.6889 Remote Similarity NPC477250
0.6887 Remote Similarity NPC239770
0.6884 Remote Similarity NPC108532
0.6883 Remote Similarity NPC31171
0.6883 Remote Similarity NPC237240
0.6875 Remote Similarity NPC278097
0.6875 Remote Similarity NPC328997
0.6875 Remote Similarity NPC294050
0.6849 Remote Similarity NPC69496
0.6838 Remote Similarity NPC477245
0.6838 Remote Similarity NPC477246
0.6835 Remote Similarity NPC169328
0.6832 Remote Similarity NPC471203
0.6831 Remote Similarity NPC84281
0.6831 Remote Similarity NPC213126
0.6831 Remote Similarity NPC160493
0.6831 Remote Similarity NPC317474
0.6831 Remote Similarity NPC291027
0.6831 Remote Similarity NPC169485
0.6821 Remote Similarity NPC307357
0.6821 Remote Similarity NPC46098
0.6821 Remote Similarity NPC268841
0.6815 Remote Similarity NPC477247
0.6806 Remote Similarity NPC477249
0.6806 Remote Similarity NPC477248
0.6806 Remote Similarity NPC472414
0.6781 Remote Similarity NPC316553
0.6781 Remote Similarity NPC295478
0.6774 Remote Similarity NPC145113
0.6767 Remote Similarity NPC329705
0.6767 Remote Similarity NPC474111
0.6767 Remote Similarity NPC193640
0.6767 Remote Similarity NPC25385
0.6767 Remote Similarity NPC475905
0.6763 Remote Similarity NPC2265
0.6752 Remote Similarity NPC201692
0.6748 Remote Similarity NPC67080
0.6744 Remote Similarity NPC145052
0.6739 Remote Similarity NPC469509
0.6731 Remote Similarity NPC173934
0.6711 Remote Similarity NPC245836
0.6711 Remote Similarity NPC233910
0.6708 Remote Similarity NPC297145
0.6708 Remote Similarity NPC197743
0.6692 Remote Similarity NPC474307
0.6691 Remote Similarity NPC210531
0.669 Remote Similarity NPC474847
0.669 Remote Similarity NPC317163
0.6689 Remote Similarity NPC68865
0.6667 Remote Similarity NPC472707
0.6667 Remote Similarity NPC213969
0.6667 Remote Similarity NPC165726
0.6667 Remote Similarity NPC65627
0.6667 Remote Similarity NPC469927
0.6667 Remote Similarity NPC15506
0.6647 Remote Similarity NPC245741
0.6644 Remote Similarity NPC79608
0.6644 Remote Similarity NPC476033
0.6644 Remote Similarity NPC65310
0.6643 Remote Similarity NPC476281
0.6643 Remote Similarity NPC476184
0.6641 Remote Similarity NPC158623
0.6623 Remote Similarity NPC136994
0.6623 Remote Similarity NPC88255
0.6623 Remote Similarity NPC251439
0.6621 Remote Similarity NPC471466
0.6619 Remote Similarity NPC472164
0.6617 Remote Similarity NPC194390
0.6617 Remote Similarity NPC113326
0.6617 Remote Similarity NPC88267
0.6617 Remote Similarity NPC224610
0.6603 Remote Similarity NPC262216
0.66 Remote Similarity NPC108553
0.6599 Remote Similarity NPC146239
0.6585 Remote Similarity NPC156348
0.6584 Remote Similarity NPC32197
0.6579 Remote Similarity NPC472247
0.6577 Remote Similarity NPC262819
0.6575 Remote Similarity NPC472165
0.6573 Remote Similarity NPC477061
0.6573 Remote Similarity NPC476183
0.6573 Remote Similarity NPC45777
0.6571 Remote Similarity NPC216387
0.6571 Remote Similarity NPC471616
0.6566 Remote Similarity NPC71205
0.6561 Remote Similarity NPC135121
0.6556 Remote Similarity NPC64897
0.6556 Remote Similarity NPC248283
0.6556 Remote Similarity NPC90693
0.6554 Remote Similarity NPC103605
0.6554 Remote Similarity NPC478165
0.6554 Remote Similarity NPC81092
0.6554 Remote Similarity NPC478162
0.6554 Remote Similarity NPC477370
0.6552 Remote Similarity NPC476278
0.6547 Remote Similarity NPC474363
0.6533 Remote Similarity NPC17567
0.6531 Remote Similarity NPC477366
0.6531 Remote Similarity NPC477363
0.6516 Remote Similarity NPC176226
0.651 Remote Similarity NPC469930
0.651 Remote Similarity NPC37968
0.6507 Remote Similarity NPC476260
0.6507 Remote Similarity NPC138798
0.6507 Remote Similarity NPC476241
0.6503 Remote Similarity NPC207675
0.6503 Remote Similarity NPC212699
0.6497 Remote Similarity NPC45307
0.6494 Remote Similarity NPC469973
0.6491 Remote Similarity NPC88378
0.6491 Remote Similarity NPC477115
0.6491 Remote Similarity NPC211713
0.6486 Remote Similarity NPC477365
0.6483 Remote Similarity NPC469494
0.6478 Remote Similarity NPC170668
0.6478 Remote Similarity NPC477737
0.6477 Remote Similarity NPC282092
0.6474 Remote Similarity NPC475413
0.6474 Remote Similarity NPC474303
0.6474 Remote Similarity NPC473497
0.6471 Remote Similarity NPC6570
0.6467 Remote Similarity NPC49272
0.6467 Remote Similarity NPC469479
0.6463 Remote Similarity NPC246166
0.6463 Remote Similarity NPC476125
0.6463 Remote Similarity NPC476179
0.6456 Remote Similarity NPC225648
0.6456 Remote Similarity NPC329761
0.6454 Remote Similarity NPC197470
0.6452 Remote Similarity NPC269398
0.6452 Remote Similarity NPC263493
0.645 Remote Similarity NPC196091
0.6447 Remote Similarity NPC169766
0.6439 Remote Similarity NPC474308
0.6439 Remote Similarity NPC476042
0.6438 Remote Similarity NPC108286
0.6438 Remote Similarity NPC205389
0.6434 Remote Similarity NPC104514
0.6433 Remote Similarity NPC201244
0.6433 Remote Similarity NPC477217
0.6429 Remote Similarity NPC217673
0.6429 Remote Similarity NPC241851
0.6429 Remote Similarity NPC52523
0.6429 Remote Similarity NPC87069
0.6429 Remote Similarity NPC309056
0.6425 Remote Similarity NPC306001
0.6425 Remote Similarity NPC473400
0.6425 Remote Similarity NPC206211
0.6425 Remote Similarity NPC324251
0.6425 Remote Similarity NPC275170
0.6425 Remote Similarity NPC471629

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC477680 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
0.7273 Intermediate Similarity NPD4738 Phase 2
0.7121 Intermediate Similarity NPD2067 Discontinued
0.6906 Remote Similarity NPD2218 Phase 2
0.6906 Remote Similarity NPD2217 Approved
0.6892 Remote Similarity NPD8265 Approved
0.6883 Remote Similarity NPD7274 Clinical (unspecified phase)
0.6857 Remote Similarity NPD5981 Approved
0.6849 Remote Similarity NPD2613 Approved
0.6831 Remote Similarity NPD3132 Approved
0.6831 Remote Similarity NPD4215 Approved
0.6831 Remote Similarity NPD4217 Approved
0.6831 Remote Similarity NPD3131 Approved
0.6831 Remote Similarity NPD2611 Approved
0.6831 Remote Similarity NPD4216 Approved
0.6831 Remote Similarity NPD4218 Approved
0.6831 Remote Similarity NPD2608 Approved
0.6831 Remote Similarity NPD2609 Approved
0.6831 Remote Similarity NPD2612 Approved
0.6831 Remote Similarity NPD2610 Approved
0.6818 Remote Similarity NPD2575 Approved
0.6788 Remote Similarity NPD2652 Approved
0.6788 Remote Similarity NPD2650 Approved
0.6781 Remote Similarity NPD3664 Approved
0.6781 Remote Similarity NPD3663 Approved
0.6781 Remote Similarity NPD3662 Phase 3
0.6781 Remote Similarity NPD3661 Approved
0.6711 Remote Similarity NPD3614 Approved
0.6711 Remote Similarity NPD3088 Approved
0.6711 Remote Similarity NPD2571 Approved
0.6711 Remote Similarity NPD2570 Approved
0.6711 Remote Similarity NPD2573 Approved
0.6711 Remote Similarity NPD3615 Approved
0.6711 Remote Similarity NPD2572 Clinical (unspecified phase)
0.6711 Remote Similarity NPD3089 Approved
0.6711 Remote Similarity NPD2574 Discontinued
0.6711 Remote Similarity NPD4745 Approved
0.6711 Remote Similarity NPD4746 Phase 3
0.6711 Remote Similarity NPD2566 Approved
0.6711 Remote Similarity NPD3616 Approved
0.6711 Remote Similarity NPD3087 Approved
0.6711 Remote Similarity NPD3090 Approved
0.6708 Remote Similarity NPD7749 Clinical (unspecified phase)
0.6689 Remote Similarity NPD8173 Phase 2
0.6689 Remote Similarity NPD8172 Phase 2
0.6667 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6646 Remote Similarity NPD8417 Discontinued
0.6644 Remote Similarity NPD2160 Approved
0.6644 Remote Similarity NPD2627 Approved
0.6644 Remote Similarity NPD2159 Approved
0.6644 Remote Similarity NPD2626 Approved
0.6644 Remote Similarity NPD2625 Approved
0.6644 Remote Similarity NPD2628 Approved
0.6642 Remote Similarity NPD467 Phase 1
0.6626 Remote Similarity NPD7972 Discontinued
0.6623 Remote Similarity NPD4684 Phase 3
0.6623 Remote Similarity NPD4686 Approved
0.6623 Remote Similarity NPD4685 Phase 3
0.6619 Remote Similarity NPD690 Clinical (unspecified phase)
0.6575 Remote Similarity NPD6325 Discontinued
0.6554 Remote Similarity NPD5204 Approved
0.6532 Remote Similarity NPD5030 Phase 2
0.6513 Remote Similarity NPD7113 Clinical (unspecified phase)
0.651 Remote Similarity NPD4620 Approved
0.651 Remote Similarity NPD4617 Approved
0.651 Remote Similarity NPD5201 Approved
0.651 Remote Similarity NPD5203 Approved
0.65 Remote Similarity NPD2629 Approved
0.6494 Remote Similarity NPD4954 Approved
0.6494 Remote Similarity NPD4955 Approved
0.6494 Remote Similarity NPD5034 Approved
0.6494 Remote Similarity NPD5028 Approved
0.6494 Remote Similarity NPD5026 Approved
0.6494 Remote Similarity NPD36 Approved
0.6483 Remote Similarity NPD4806 Approved
0.6483 Remote Similarity NPD4807 Approved
0.6458 Remote Similarity NPD5305 Approved
0.6458 Remote Similarity NPD5306 Approved
0.6454 Remote Similarity NPD1348 Approved
0.6449 Remote Similarity NPD3644 Approved
0.6449 Remote Similarity NPD3642 Approved
0.6449 Remote Similarity NPD3643 Approved
0.6449 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6447 Remote Similarity NPD6309 Approved
0.6447 Remote Similarity NPD5119 Approved
0.6447 Remote Similarity NPD5121 Approved
0.6447 Remote Similarity NPD5120 Approved
0.6447 Remote Similarity NPD6311 Approved
0.6447 Remote Similarity NPD6310 Approved
0.6438 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6424 Remote Similarity NPD4619 Approved
0.6424 Remote Similarity NPD4621 Approved
0.642 Remote Similarity NPD8407 Phase 2
0.6414 Remote Similarity NPD4106 Approved
0.6414 Remote Similarity NPD4135 Approved
0.6414 Remote Similarity NPD4136 Approved
0.641 Remote Similarity NPD4152 Approved
0.64 Remote Similarity NPD5202 Clinical (unspecified phase)
0.6384 Remote Similarity NPD5036 Approved
0.6364 Remote Similarity NPD5035 Approved
0.6348 Remote Similarity NPD5037 Approved
0.6348 Remote Similarity NPD5038 Approved
0.6343 Remote Similarity NPD8368 Discontinued
0.634 Remote Similarity NPD8416 Discontinued
0.6327 Remote Similarity NPD5108 Clinical (unspecified phase)
0.6323 Remote Similarity NPD6852 Discontinued
0.6319 Remote Similarity NPD4479 Discontinued
0.6296 Remote Similarity NPD6647 Phase 2
0.6284 Remote Similarity NPD5157 Phase 1
0.6284 Remote Similarity NPD5159 Phase 2
0.6284 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6278 Remote Similarity NPD8435 Approved
0.6277 Remote Similarity NPD6685 Approved
0.6276 Remote Similarity NPD4105 Approved
0.6276 Remote Similarity NPD4102 Approved
0.6269 Remote Similarity NPD4760 Clinical (unspecified phase)
0.6268 Remote Similarity NPD1711 Phase 2
0.6266 Remote Similarity NPD2424 Discontinued
0.625 Remote Similarity NPD8485 Approved
0.6242 Remote Similarity NPD5667 Approved
0.6242 Remote Similarity NPD4172 Approved
0.6242 Remote Similarity NPD4173 Approved
0.6242 Remote Similarity NPD5712 Approved
0.6232 Remote Similarity NPD6406 Approved
0.6193 Remote Similarity NPD3823 Discontinued
0.6188 Remote Similarity NPD6676 Phase 2
0.6188 Remote Similarity NPD8361 Approved
0.6188 Remote Similarity NPD8360 Approved
0.6183 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6181 Remote Similarity NPD3123 Discovery
0.6181 Remote Similarity NPD4574 Approved
0.6181 Remote Similarity NPD4576 Approved
0.6178 Remote Similarity NPD3648 Clinical (unspecified phase)
0.617 Remote Similarity NPD969 Suspended
0.6167 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6159 Remote Similarity NPD6007 Clinical (unspecified phase)
0.615 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6149 Remote Similarity NPD8323 Discontinued
0.6149 Remote Similarity NPD3603 Phase 3
0.6149 Remote Similarity NPD5618 Discontinued
0.6144 Remote Similarity NPD3136 Phase 2
0.6143 Remote Similarity NPD4233 Approved
0.6143 Remote Similarity NPD4234 Approved
0.6143 Remote Similarity NPD9713 Approved
0.6139 Remote Similarity NPD2161 Phase 2
0.6138 Remote Similarity NPD7522 Discontinued
0.6136 Remote Similarity NPD4814 Discontinued
0.6131 Remote Similarity NPD1237 Approved
0.6119 Remote Similarity NPD9495 Approved
0.6118 Remote Similarity NPD3626 Phase 3
0.6118 Remote Similarity NPD7084 Phase 3
0.6115 Remote Similarity NPD2569 Approved
0.6115 Remote Similarity NPD2567 Approved
0.6101 Remote Similarity NPD7978 Discontinued
0.6098 Remote Similarity NPD7613 Discontinued
0.6096 Remote Similarity NPD7565 Approved
0.609 Remote Similarity NPD6355 Discontinued
0.609 Remote Similarity NPD8643 Discontinued
0.6087 Remote Similarity NPD1040 Phase 2
0.6087 Remote Similarity NPD3400 Discontinued
0.6087 Remote Similarity NPD1018 Approved
0.608 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6074 Remote Similarity NPD2066 Phase 3
0.6069 Remote Similarity NPD7315 Approved
0.6067 Remote Similarity NPD5029 Approved
0.6067 Remote Similarity NPD5027 Approved
0.6067 Remote Similarity NPD5031 Approved
0.6062 Remote Similarity NPD7596 Clinical (unspecified phase)
0.6061 Remote Similarity NPD3719 Approved
0.6061 Remote Similarity NPD1066 Discontinued
0.6061 Remote Similarity NPD3718 Approved
0.6058 Remote Similarity NPD5765 Approved
0.6056 Remote Similarity NPD6912 Phase 3
0.6054 Remote Similarity NPD4209 Clinical (unspecified phase)
0.6053 Remote Similarity NPD5647 Approved
0.6042 Remote Similarity NPD4766 Approved
0.6037 Remote Similarity NPD681 Clinical (unspecified phase)
0.6037 Remote Similarity NPD4662 Approved
0.6037 Remote Similarity NPD4661 Approved
0.6034 Remote Similarity NPD5032 Approved
0.6028 Remote Similarity NPD1756 Approved
0.6028 Remote Similarity NPD1752 Approved
0.6027 Remote Similarity NPD1758 Phase 1
0.6027 Remote Similarity NPD6065 Approved
0.6022 Remote Similarity NPD3154 Approved
0.6022 Remote Similarity NPD3153 Approved
0.6015 Remote Similarity NPD1693 Approved
0.6014 Remote Similarity NPD2607 Approved
0.6012 Remote Similarity NPD3300 Phase 2
0.6011 Remote Similarity NPD6836 Approved
0.6 Remote Similarity NPD4198 Discontinued
0.6 Remote Similarity NPD2584 Suspended
0.6 Remote Similarity NPD52 Approved
0.6 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6 Remote Similarity NPD7526 Approved
0.6 Remote Similarity NPD1048 Approved
0.5986 Remote Similarity NPD1759 Phase 1
0.5986 Remote Similarity NPD2617 Discontinued
0.5986 Remote Similarity NPD7601 Clinical (unspecified phase)
0.5986 Remote Similarity NPD998 Approved
0.5985 Remote Similarity NPD4719 Phase 2

Structure

External Identifiers

PubChem CID   24879338
ChEMBL   CHEMBL466747
ZINC  

Physicochemical Properties

Molecular Weight:  331.14
ALogP:  -0.6714
MLogP:  2.78
XLogP:  3.485
# Rotatable Bonds:  9
Polar Surface Area:  99.35
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  24

Download Data

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