Natural Product: NPC477684

Natural Product ID:  NPC477684
Common Name:   7-Deacetoxyyanuthone A
IUPAC Name:   (1R,2R,6R)-3-ethyl-2-hydroxy-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]-7-oxabicyclo[4.1.0]hept-3-en-5-one
Synonyms:  
Molecular Formula:   C23H34O3
Standard InCHIKey:  BMDMRPRGJZSKOI-BVNLDUDUSA-N
Standard InCHI:  InChI=1S/C23H34O3/c1-6-19-15-20(24)23(22(26-23)21(19)25)14-13-18(5)12-8-11-17(4)10-7-9-16(2)3/h9,11,13,15,21-22,25H,6-8,10,12,14H2,1-5H3/b17-11+,18-13+/t21-,22-,23+/m1/s1
Canonical SMILES:  CCC1=CC(=O)[C@]2([C@@H]([C@@H]1O)O2)C/C=C(/CC/C=C(/CCC=C(C)C)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 PMID[14640527]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT81 Cell Line A549 Homo sapiens ED50 = 7.74 ug/ml 14640527
NPT146 Cell Line SK-OV-3 Homo sapiens ED50 = 6.35 ug/ml 14640527
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 = 3.86 ug/ml 14640527
NPT574 Cell Line XF498 Homo sapiens ED50 = 10.04 ug/ml 14640527
NPT148 Cell Line HCT-15 Homo sapiens ED50 = 10.07 ug/ml 14640527
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 50 ug/ml 14640527

  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 NPC477684 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
0.9524 High Similarity NPC196381
0.8737 High Similarity NPC39996
0.84 Intermediate Similarity NPC87335
0.8315 Intermediate Similarity NPC187529
0.8295 Intermediate Similarity NPC477784
0.8295 Intermediate Similarity NPC477785
0.8295 Intermediate Similarity NPC477786
0.8265 Intermediate Similarity NPC104161
0.8265 Intermediate Similarity NPC118902
0.8265 Intermediate Similarity NPC469980
0.8235 Intermediate Similarity NPC272267
0.8132 Intermediate Similarity NPC472007
0.8058 Intermediate Similarity NPC317107
0.8022 Intermediate Similarity NPC472009
0.802 Intermediate Similarity NPC266514
0.8 Intermediate Similarity NPC469809
0.7981 Intermediate Similarity NPC317687
0.798 Intermediate Similarity NPC478176
0.7978 Intermediate Similarity NPC253364
0.7935 Intermediate Similarity NPC471738
0.7931 Intermediate Similarity NPC231739
0.7931 Intermediate Similarity NPC478122
0.7879 Intermediate Similarity NPC207885
0.7879 Intermediate Similarity NPC112613
0.7857 Intermediate Similarity NPC306908
0.7849 Intermediate Similarity NPC472008
0.7835 Intermediate Similarity NPC279722
0.7789 Intermediate Similarity NPC475441
0.7789 Intermediate Similarity NPC476705
0.7767 Intermediate Similarity NPC322903
0.7755 Intermediate Similarity NPC471916
0.7742 Intermediate Similarity NPC23622
0.7684 Intermediate Similarity NPC471399
0.767 Intermediate Similarity NPC469853
0.7667 Intermediate Similarity NPC221510
0.7667 Intermediate Similarity NPC159714
0.7653 Intermediate Similarity NPC94337
0.7629 Intermediate Similarity NPC121825
0.7614 Intermediate Similarity NPC97173
0.7582 Intermediate Similarity NPC47450
0.7549 Intermediate Similarity NPC131366
0.7547 Intermediate Similarity NPC476023
0.7526 Intermediate Similarity NPC469692
0.7526 Intermediate Similarity NPC469645
0.75 Intermediate Similarity NPC469464
0.75 Intermediate Similarity NPC80650
0.7474 Intermediate Similarity NPC476707
0.7474 Intermediate Similarity NPC476706
0.7453 Intermediate Similarity NPC89408
0.7423 Intermediate Similarity NPC146852
0.7423 Intermediate Similarity NPC142838
0.7419 Intermediate Similarity NPC60951
0.7416 Intermediate Similarity NPC82666
0.7416 Intermediate Similarity NPC471061
0.7404 Intermediate Similarity NPC469852
0.74 Intermediate Similarity NPC236176
0.74 Intermediate Similarity NPC20066
0.74 Intermediate Similarity NPC471694
0.7379 Intermediate Similarity NPC473624
0.7368 Intermediate Similarity NPC179659
0.7364 Intermediate Similarity NPC286528
0.7364 Intermediate Similarity NPC20302
0.7364 Intermediate Similarity NPC167606
0.7364 Intermediate Similarity NPC470493
0.7364 Intermediate Similarity NPC312824
0.7364 Intermediate Similarity NPC183580
0.7364 Intermediate Similarity NPC470492
0.7364 Intermediate Similarity NPC140055
0.7363 Intermediate Similarity NPC472948
0.7353 Intermediate Similarity NPC46998
0.7353 Intermediate Similarity NPC164598
0.7353 Intermediate Similarity NPC474339
0.7353 Intermediate Similarity NPC110443
0.7353 Intermediate Similarity NPC476897
0.7353 Intermediate Similarity NPC185141
0.7353 Intermediate Similarity NPC133907
0.7353 Intermediate Similarity NPC128733
0.7347 Intermediate Similarity NPC61275
0.734 Intermediate Similarity NPC79573
0.7333 Intermediate Similarity NPC13823
0.7333 Intermediate Similarity NPC474716
0.7333 Intermediate Similarity NPC68119
0.7327 Intermediate Similarity NPC300584
0.7327 Intermediate Similarity NPC35717
0.732 Intermediate Similarity NPC265856
0.732 Intermediate Similarity NPC166554
0.732 Intermediate Similarity NPC131864
0.7312 Intermediate Similarity NPC251475
0.7312 Intermediate Similarity NPC169941
0.7303 Intermediate Similarity NPC271070
0.7303 Intermediate Similarity NPC474197
0.7297 Intermediate Similarity NPC186525
0.7297 Intermediate Similarity NPC709
0.7297 Intermediate Similarity NPC50774
0.729 Intermediate Similarity NPC161816
0.729 Intermediate Similarity NPC115257
0.7283 Intermediate Similarity NPC275766
0.7283 Intermediate Similarity NPC286229
0.7273 Intermediate Similarity NPC270929
0.7264 Intermediate Similarity NPC233379
0.7264 Intermediate Similarity NPC327106
0.7264 Intermediate Similarity NPC14862
0.7264 Intermediate Similarity NPC474664
0.7264 Intermediate Similarity NPC264819
0.7263 Intermediate Similarity NPC262026
0.7253 Intermediate Similarity NPC471740
0.7245 Intermediate Similarity NPC116726
0.7232 Intermediate Similarity NPC264954
0.7232 Intermediate Similarity NPC473274
0.7222 Intermediate Similarity NPC473536
0.7212 Intermediate Similarity NPC472755
0.7209 Intermediate Similarity NPC477449
0.7209 Intermediate Similarity NPC477448
0.7207 Intermediate Similarity NPC243065
0.7196 Intermediate Similarity NPC15218
0.7196 Intermediate Similarity NPC475922
0.7196 Intermediate Similarity NPC471400
0.7184 Intermediate Similarity NPC472753
0.717 Intermediate Similarity NPC194620
0.717 Intermediate Similarity NPC473284
0.717 Intermediate Similarity NPC72813
0.717 Intermediate Similarity NPC473165
0.717 Intermediate Similarity NPC326994
0.717 Intermediate Similarity NPC324327
0.717 Intermediate Similarity NPC474421
0.7168 Intermediate Similarity NPC474370
0.7158 Intermediate Similarity NPC15807
0.7158 Intermediate Similarity NPC77971
0.7157 Intermediate Similarity NPC161855
0.7156 Intermediate Similarity NPC473877
0.7155 Intermediate Similarity NPC225049
0.7143 Intermediate Similarity NPC472756
0.7143 Intermediate Similarity NPC329736
0.7143 Intermediate Similarity NPC473099
0.7143 Intermediate Similarity NPC251310
0.7143 Intermediate Similarity NPC72255
0.7129 Intermediate Similarity NPC473291
0.7129 Intermediate Similarity NPC93271
0.7129 Intermediate Similarity NPC135576
0.7128 Intermediate Similarity NPC161045
0.7128 Intermediate Similarity NPC110150
0.7128 Intermediate Similarity NPC66764
0.7115 Intermediate Similarity NPC472754
0.7115 Intermediate Similarity NPC471148
0.7113 Intermediate Similarity NPC269677
0.7113 Intermediate Similarity NPC53454
0.7113 Intermediate Similarity NPC476708
0.7105 Intermediate Similarity NPC473256
0.7105 Intermediate Similarity NPC470878
0.7105 Intermediate Similarity NPC67569
0.7103 Intermediate Similarity NPC151393
0.7103 Intermediate Similarity NPC327286
0.7103 Intermediate Similarity NPC55972
0.7103 Intermediate Similarity NPC169888
0.71 Intermediate Similarity NPC78159
0.71 Intermediate Similarity NPC472976
0.71 Intermediate Similarity NPC472977
0.71 Intermediate Similarity NPC196227
0.71 Intermediate Similarity NPC477241
0.7097 Intermediate Similarity NPC470298
0.7097 Intermediate Similarity NPC67254
0.7091 Intermediate Similarity NPC477266
0.7091 Intermediate Similarity NPC317210
0.7091 Intermediate Similarity NPC122056
0.7087 Intermediate Similarity NPC469551
0.7083 Intermediate Similarity NPC476043
0.7083 Intermediate Similarity NPC202394
0.708 Intermediate Similarity NPC61520
0.7079 Intermediate Similarity NPC160540
0.7075 Intermediate Similarity NPC16313
0.7075 Intermediate Similarity NPC9303
0.7075 Intermediate Similarity NPC475802
0.7075 Intermediate Similarity NPC166607
0.7071 Intermediate Similarity NPC32552
0.7071 Intermediate Similarity NPC230623
0.7069 Intermediate Similarity NPC473919
0.7069 Intermediate Similarity NPC473709
0.7065 Intermediate Similarity NPC281138
0.7065 Intermediate Similarity NPC136033
0.7059 Intermediate Similarity NPC239895
0.7059 Intermediate Similarity NPC266842
0.7059 Intermediate Similarity NPC472072
0.7059 Intermediate Similarity NPC474785
0.7059 Intermediate Similarity NPC474938
0.7054 Intermediate Similarity NPC27999
0.7054 Intermediate Similarity NPC477116
0.7053 Intermediate Similarity NPC31086
0.7053 Intermediate Similarity NPC295799
0.7048 Intermediate Similarity NPC249187
0.7048 Intermediate Similarity NPC247957
0.7048 Intermediate Similarity NPC475050
0.7043 Intermediate Similarity NPC470265
0.7043 Intermediate Similarity NPC153700
0.7043 Intermediate Similarity NPC88326
0.7043 Intermediate Similarity NPC23786
0.7041 Intermediate Similarity NPC473100
0.7041 Intermediate Similarity NPC206001
0.7041 Intermediate Similarity NPC218927
0.7037 Intermediate Similarity NPC77089
0.7037 Intermediate Similarity NPC214644

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC477684 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
0.7364 Intermediate Similarity NPD7115 Discovery
0.7143 Intermediate Similarity NPD46 Approved
0.7143 Intermediate Similarity NPD6698 Approved
0.7128 Intermediate Similarity NPD6110 Phase 1
0.6827 Remote Similarity NPD4225 Approved
0.6809 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6804 Remote Similarity NPD1696 Phase 3
0.6733 Remote Similarity NPD7983 Approved
0.6667 Remote Similarity NPD7331 Phase 2
0.6667 Remote Similarity NPD5778 Approved
0.6667 Remote Similarity NPD5779 Approved
0.6667 Remote Similarity NPD6371 Approved
0.6633 Remote Similarity NPD5363 Approved
0.6606 Remote Similarity NPD5739 Approved
0.6606 Remote Similarity NPD6675 Approved
0.6606 Remote Similarity NPD7128 Approved
0.6606 Remote Similarity NPD6402 Approved
0.6602 Remote Similarity NPD5282 Discontinued
0.6577 Remote Similarity NPD6372 Approved
0.6577 Remote Similarity NPD6373 Approved
0.6566 Remote Similarity NPD3618 Phase 1
0.6549 Remote Similarity NPD8297 Approved
0.6545 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6542 Remote Similarity NPD5344 Discontinued
0.6495 Remote Similarity NPD4269 Approved
0.6495 Remote Similarity NPD4270 Approved
0.6489 Remote Similarity NPD4756 Discovery
0.6486 Remote Similarity NPD6899 Approved
0.6486 Remote Similarity NPD6881 Approved
0.6486 Remote Similarity NPD7320 Approved
0.6481 Remote Similarity NPD5211 Phase 2
0.6477 Remote Similarity NPD3704 Approved
0.6471 Remote Similarity NPD5785 Approved
0.646 Remote Similarity NPD6649 Approved
0.646 Remote Similarity NPD6650 Approved
0.6458 Remote Similarity NPD4252 Approved
0.6441 Remote Similarity NPD6059 Approved
0.6441 Remote Similarity NPD6054 Approved
0.6441 Remote Similarity NPD6319 Approved
0.6429 Remote Similarity NPD7154 Phase 3
0.6417 Remote Similarity NPD8328 Phase 3
0.6415 Remote Similarity NPD6084 Phase 2
0.6415 Remote Similarity NPD4755 Approved
0.6415 Remote Similarity NPD6083 Phase 2
0.64 Remote Similarity NPD5786 Approved
0.6396 Remote Similarity NPD5697 Approved
0.6396 Remote Similarity NPD5701 Approved
0.6392 Remote Similarity NPD5369 Approved
0.6387 Remote Similarity NPD8517 Approved
0.6387 Remote Similarity NPD8513 Phase 3
0.6387 Remote Similarity NPD8515 Approved
0.6387 Remote Similarity NPD8516 Approved
0.6373 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6373 Remote Similarity NPD6101 Approved
0.6373 Remote Similarity NPD5328 Approved
0.6372 Remote Similarity NPD4634 Approved
0.6372 Remote Similarity NPD7102 Approved
0.6372 Remote Similarity NPD7290 Approved
0.6372 Remote Similarity NPD6883 Approved
0.6364 Remote Similarity NPD5141 Approved
0.6333 Remote Similarity NPD6370 Approved
0.6327 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6321 Remote Similarity NPD4697 Phase 3
0.6316 Remote Similarity NPD6617 Approved
0.6316 Remote Similarity NPD8130 Phase 1
0.6316 Remote Similarity NPD6847 Approved
0.6316 Remote Similarity NPD7601 Clinical (unspecified phase)
0.6316 Remote Similarity NPD6869 Approved
0.6311 Remote Similarity NPD7838 Discovery
0.6296 Remote Similarity NPD5285 Approved
0.6296 Remote Similarity NPD4700 Approved
0.6296 Remote Similarity NPD5286 Approved
0.6296 Remote Similarity NPD4696 Approved
0.6292 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6286 Remote Similarity NPD7748 Approved
0.6283 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6283 Remote Similarity NPD6013 Approved
0.6283 Remote Similarity NPD6014 Approved
0.6283 Remote Similarity NPD6012 Approved
0.6262 Remote Similarity NPD7902 Approved
0.6261 Remote Similarity NPD6882 Approved
0.625 Remote Similarity NPD6015 Approved
0.625 Remote Similarity NPD7515 Phase 2
0.625 Remote Similarity NPD6016 Approved
0.625 Remote Similarity NPD6079 Approved
0.625 Remote Similarity NPD6411 Approved
0.623 Remote Similarity NPD7492 Approved
0.6226 Remote Similarity NPD5695 Phase 3
0.6214 Remote Similarity NPD4753 Phase 2
0.6207 Remote Similarity NPD368 Approved
0.6204 Remote Similarity NPD5696 Approved
0.62 Remote Similarity NPD4786 Approved
0.6198 Remote Similarity NPD5988 Approved
0.6195 Remote Similarity NPD6011 Approved
0.6195 Remote Similarity NPD5345 Clinical (unspecified phase)
0.619 Remote Similarity NPD4202 Approved
0.6182 Remote Similarity NPD5224 Approved
0.6182 Remote Similarity NPD5226 Approved
0.6182 Remote Similarity NPD5225 Approved
0.6182 Remote Similarity NPD4633 Approved
0.618 Remote Similarity NPD2685 Clinical (unspecified phase)
0.618 Remote Similarity NPD7341 Phase 2
0.6179 Remote Similarity NPD6616 Approved
0.6174 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6174 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6168 Remote Similarity NPD7839 Suspended
0.6168 Remote Similarity NPD5221 Approved
0.6168 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6168 Remote Similarity NPD5222 Approved
0.6162 Remote Similarity NPD3667 Approved
0.6147 Remote Similarity NPD6648 Approved
0.6139 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6139 Remote Similarity NPD1694 Approved
0.6136 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6129 Remote Similarity NPD8074 Phase 3
0.6129 Remote Similarity NPD7078 Approved
0.6129 Remote Similarity NPD8293 Discontinued
0.6126 Remote Similarity NPD5175 Approved
0.6126 Remote Similarity NPD5174 Approved
0.6111 Remote Similarity NPD5173 Approved
0.61 Remote Similarity NPD5362 Discontinued
0.6091 Remote Similarity NPD5223 Approved
0.6087 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6082 Remote Similarity NPD5784 Clinical (unspecified phase)
0.608 Remote Similarity NPD7736 Approved
0.6078 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6078 Remote Similarity NPD5279 Phase 3
0.6075 Remote Similarity NPD4629 Approved
0.6075 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6075 Remote Similarity NPD5210 Approved
0.6068 Remote Similarity NPD4632 Approved
0.6067 Remote Similarity NPD3197 Phase 1
0.6055 Remote Similarity NPD8029 Clinical (unspecified phase)
0.605 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6042 Remote Similarity NPD818 Approved
0.6042 Remote Similarity NPD819 Approved
0.604 Remote Similarity NPD6400 Clinical (unspecified phase)
0.604 Remote Similarity NPD3665 Phase 1
0.604 Remote Similarity NPD3666 Approved
0.604 Remote Similarity NPD3133 Approved
0.6038 Remote Similarity NPD6399 Phase 3
0.6018 Remote Similarity NPD4768 Approved
0.6018 Remote Similarity NPD4767 Approved
0.6016 Remote Similarity NPD7604 Phase 2
0.6 Remote Similarity NPD7639 Approved
0.6 Remote Similarity NPD7640 Approved
0.5982 Remote Similarity NPD4754 Approved
0.5981 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5981 Remote Similarity NPD7900 Approved
0.598 Remote Similarity NPD5329 Approved
0.5966 Remote Similarity NPD6274 Approved
0.5965 Remote Similarity NPD6412 Phase 2
0.5962 Remote Similarity NPD5737 Approved
0.5962 Remote Similarity NPD6672 Approved
0.596 Remote Similarity NPD5790 Clinical (unspecified phase)
0.596 Remote Similarity NPD4695 Discontinued
0.596 Remote Similarity NPD4820 Approved
0.596 Remote Similarity NPD4819 Approved
0.596 Remote Similarity NPD4822 Approved
0.596 Remote Similarity NPD4821 Approved
0.5952 Remote Similarity NPD6033 Approved
0.595 Remote Similarity NPD7100 Approved
0.595 Remote Similarity NPD7101 Approved
0.5943 Remote Similarity NPD7637 Suspended
0.5943 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5938 Remote Similarity NPD8264 Approved
0.5922 Remote Similarity NPD4623 Approved
0.5922 Remote Similarity NPD4519 Discontinued
0.5917 Remote Similarity NPD6009 Approved
0.5913 Remote Similarity NPD4729 Approved
0.5913 Remote Similarity NPD5128 Approved
0.5913 Remote Similarity NPD4730 Approved
0.5909 Remote Similarity NPD7638 Approved
0.5905 Remote Similarity NPD5370 Suspended
0.5897 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5887 Remote Similarity NPD7642 Approved
0.5882 Remote Similarity NPD4197 Approved
0.5877 Remote Similarity NPD6008 Approved
0.5868 Remote Similarity NPD6335 Approved
0.5854 Remote Similarity NPD6909 Approved
0.5854 Remote Similarity NPD5983 Phase 2
0.5854 Remote Similarity NPD6908 Approved
0.5842 Remote Similarity NPD6435 Approved
0.5833 Remote Similarity NPD6868 Approved
0.5826 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5812 Remote Similarity NPD5249 Phase 3
0.5812 Remote Similarity NPD5250 Approved
0.5812 Remote Similarity NPD5247 Approved
0.5812 Remote Similarity NPD5248 Approved
0.5812 Remote Similarity NPD5251 Approved
0.5794 Remote Similarity NPD6336 Discontinued
0.5785 Remote Similarity NPD6317 Approved
0.5781 Remote Similarity NPD7319 Approved
0.578 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5776 Remote Similarity NPD6686 Approved
0.5773 Remote Similarity NPD8039 Approved
0.5772 Remote Similarity NPD7299 Clinical (unspecified phase)
0.5769 Remote Similarity NPD7521 Approved
0.5769 Remote Similarity NPD6684 Approved
0.5769 Remote Similarity NPD5280 Approved

Structure

External Identifiers

PubChem CID   44566894
ChEMBL   CHEMBL461177
ZINC  

Physicochemical Properties

Molecular Weight:  358.25
ALogP:  3.2915
MLogP:  3.66
XLogP:  4.271
# Rotatable Bonds:  15
Polar Surface Area:  49.83
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  26

Download Data

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