Natural Product: NPC31021

Natural Product ID:  NPC31021
Common Name:   Chermesinone B
IUPAC Name:   (6aR,9S,9aS)-3,6a-dimethyl-9-[(2S)-2-methylbutanoyl]-9,9a-dihydrofuro[2,3-h]isochromene-6,8-dione
Synonyms:   Chermesinone B
Molecular Formula:   C18H20O5
Standard InCHIKey:  MZMGICPQNSXAGE-SRSSHDMCSA-N
Standard InCHI:  InChI=1S/C18H20O5/c1-5-9(2)16(20)14-15-12-8-22-10(3)6-11(12)7-13(19)18(15,4)23-17(14)21/h6-9,14-15H,5H2,1-4H3/t9-,14-,15+,18-/m0/s1
Canonical SMILES:  CC[C@@H](C(=O)[C@H]1C(=O)O[C@@]2([C@@H]1C1=COC(=CC1=CC2=O)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
NPO9828 Penicillium chermesinum Species Aspergillaceae Eukaryota isolated from the stem of the mangrove plant Kandelia candel South China Sea in Guangdong Province, China PMID[21510637]
NPO8113 Streptomyces murayamaensis Species Streptomycetaceae Bacteria UNPD*
NPO9828 Penicillium chermesinum Species Aspergillaceae Eukaryota PMID[21510637]
NPO7400 Marsdenia cundurango Species Apocynaceae Eukaryota UNPD*
NPO1216 Aesculus indica Species Hippocastanaceae Eukaryota UNPD*
NPO11924 Sesuvium portulaca Species Aizoaceae Eukaryota UNPD*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified IC50 > 100000 nM 21510637
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus IC50 > 100000 nM 21510637

  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 NPC31021 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
0.9263 High Similarity NPC271059
0.9263 High Similarity NPC25666
0.883 High Similarity NPC318082
0.88 High Similarity NPC23497
0.8602 High Similarity NPC166110
0.8511 High Similarity NPC248193
0.8462 Intermediate Similarity NPC203795
0.8387 Intermediate Similarity NPC142159
0.8387 Intermediate Similarity NPC95364
0.8286 Intermediate Similarity NPC326264
0.8211 Intermediate Similarity NPC193396
0.8211 Intermediate Similarity NPC32944
0.8056 Intermediate Similarity NPC243298
0.7959 Intermediate Similarity NPC471698
0.7921 Intermediate Similarity NPC471699
0.7909 Intermediate Similarity NPC245320
0.7838 Intermediate Similarity NPC476815
0.7838 Intermediate Similarity NPC31641
0.7838 Intermediate Similarity NPC473145
0.7789 Intermediate Similarity NPC38885
0.7789 Intermediate Similarity NPC471739
0.7766 Intermediate Similarity NPC281172
0.7766 Intermediate Similarity NPC472686
0.7766 Intermediate Similarity NPC290329
0.7745 Intermediate Similarity NPC469851
0.77 Intermediate Similarity NPC472674
0.77 Intermediate Similarity NPC269492
0.77 Intermediate Similarity NPC121036
0.7684 Intermediate Similarity NPC38576
0.7684 Intermediate Similarity NPC291712
0.7684 Intermediate Similarity NPC279859
0.7596 Intermediate Similarity NPC320294
0.7596 Intermediate Similarity NPC297281
0.7596 Intermediate Similarity NPC473144
0.7551 Intermediate Similarity NPC469372
0.7551 Intermediate Similarity NPC220454
0.7551 Intermediate Similarity NPC212679
0.7551 Intermediate Similarity NPC469595
0.7549 Intermediate Similarity NPC472730
0.7549 Intermediate Similarity NPC153776
0.7549 Intermediate Similarity NPC177680
0.7549 Intermediate Similarity NPC472729
0.7527 Intermediate Similarity NPC474353
0.7526 Intermediate Similarity NPC190718
0.7524 Intermediate Similarity NPC272528
0.75 Intermediate Similarity NPC143210
0.75 Intermediate Similarity NPC56525
0.7476 Intermediate Similarity NPC472727
0.7476 Intermediate Similarity NPC472728
0.7476 Intermediate Similarity NPC46761
0.7455 Intermediate Similarity NPC321496
0.7455 Intermediate Similarity NPC474271
0.7453 Intermediate Similarity NPC469852
0.7453 Intermediate Similarity NPC85529
0.7453 Intermediate Similarity NPC32006
0.7449 Intermediate Similarity NPC280833
0.7426 Intermediate Similarity NPC12727
0.7426 Intermediate Similarity NPC295347
0.7391 Intermediate Similarity NPC478246
0.7391 Intermediate Similarity NPC478247
0.7383 Intermediate Similarity NPC469853
0.7374 Intermediate Similarity NPC253177
0.7374 Intermediate Similarity NPC223093
0.7374 Intermediate Similarity NPC213636
0.7374 Intermediate Similarity NPC280592
0.7353 Intermediate Similarity NPC472733
0.7353 Intermediate Similarity NPC472734
0.7353 Intermediate Similarity NPC476275
0.734 Intermediate Similarity NPC286229
0.7333 Intermediate Similarity NPC163249
0.7327 Intermediate Similarity NPC469819
0.7327 Intermediate Similarity NPC114162
0.732 Intermediate Similarity NPC229717
0.7312 Intermediate Similarity NPC276647
0.7312 Intermediate Similarity NPC28319
0.7312 Intermediate Similarity NPC622
0.7312 Intermediate Similarity NPC471740
0.73 Intermediate Similarity NPC32552
0.73 Intermediate Similarity NPC296114
0.73 Intermediate Similarity NPC471329
0.729 Intermediate Similarity NPC292588
0.7283 Intermediate Similarity NPC283087
0.7282 Intermediate Similarity NPC134083
0.7282 Intermediate Similarity NPC472732
0.7282 Intermediate Similarity NPC208094
0.7282 Intermediate Similarity NPC27105
0.7282 Intermediate Similarity NPC216904
0.7282 Intermediate Similarity NPC471694
0.7282 Intermediate Similarity NPC226986
0.7282 Intermediate Similarity NPC472731
0.7281 Intermediate Similarity NPC158963
0.7273 Intermediate Similarity NPC34315
0.7273 Intermediate Similarity NPC284561
0.7264 Intermediate Similarity NPC179208
0.7263 Intermediate Similarity NPC471326
0.7263 Intermediate Similarity NPC221231
0.7255 Intermediate Similarity NPC777
0.7255 Intermediate Similarity NPC273197
0.7255 Intermediate Similarity NPC234339
0.7248 Intermediate Similarity NPC250018
0.7245 Intermediate Similarity NPC181327
0.7238 Intermediate Similarity NPC469657
0.7238 Intermediate Similarity NPC244456
0.7228 Intermediate Similarity NPC1108
0.7228 Intermediate Similarity NPC476598
0.7228 Intermediate Similarity NPC476597
0.7228 Intermediate Similarity NPC477615
0.7216 Intermediate Similarity NPC470177
0.7216 Intermediate Similarity NPC133652
0.7216 Intermediate Similarity NPC90287
0.7212 Intermediate Similarity NPC471331
0.7212 Intermediate Similarity NPC471330
0.7212 Intermediate Similarity NPC472687
0.7212 Intermediate Similarity NPC112753
0.7212 Intermediate Similarity NPC54843
0.7212 Intermediate Similarity NPC264378
0.7212 Intermediate Similarity NPC275439
0.7212 Intermediate Similarity NPC203388
0.7212 Intermediate Similarity NPC99657
0.7207 Intermediate Similarity NPC193948
0.7204 Intermediate Similarity NPC35574
0.72 Intermediate Similarity NPC471818
0.72 Intermediate Similarity NPC152467
0.72 Intermediate Similarity NPC469718
0.72 Intermediate Similarity NPC329857
0.72 Intermediate Similarity NPC224270
0.7196 Intermediate Similarity NPC13385
0.7196 Intermediate Similarity NPC213366
0.7193 Intermediate Similarity NPC21326
0.7184 Intermediate Similarity NPC472675
0.7184 Intermediate Similarity NPC21681
0.7184 Intermediate Similarity NPC301596
0.7184 Intermediate Similarity NPC112654
0.7184 Intermediate Similarity NPC299396
0.7184 Intermediate Similarity NPC172998
0.7172 Intermediate Similarity NPC471047
0.7172 Intermediate Similarity NPC469653
0.7172 Intermediate Similarity NPC469628
0.7172 Intermediate Similarity NPC475906
0.7172 Intermediate Similarity NPC472302
0.7172 Intermediate Similarity NPC469631
0.7168 Intermediate Similarity NPC270478
0.7158 Intermediate Similarity NPC474085
0.7158 Intermediate Similarity NPC475665
0.7157 Intermediate Similarity NPC477129
0.7157 Intermediate Similarity NPC473435
0.7157 Intermediate Similarity NPC477130
0.7157 Intermediate Similarity NPC476596
0.7157 Intermediate Similarity NPC38830
0.7157 Intermediate Similarity NPC473280
0.7157 Intermediate Similarity NPC473431
0.7157 Intermediate Similarity NPC470697
0.7157 Intermediate Similarity NPC471078
0.7143 Intermediate Similarity NPC215253
0.7143 Intermediate Similarity NPC474802
0.7143 Intermediate Similarity NPC185253
0.7143 Intermediate Similarity NPC104861
0.7143 Intermediate Similarity NPC477478
0.7143 Intermediate Similarity NPC472929
0.7143 Intermediate Similarity NPC477479
0.7143 Intermediate Similarity NPC472972
0.7129 Intermediate Similarity NPC20713
0.7117 Intermediate Similarity NPC43775
0.7115 Intermediate Similarity NPC239895
0.7115 Intermediate Similarity NPC23680
0.7115 Intermediate Similarity NPC478233
0.7113 Intermediate Similarity NPC469569
0.7113 Intermediate Similarity NPC139566
0.7103 Intermediate Similarity NPC275583
0.71 Intermediate Similarity NPC73995
0.71 Intermediate Similarity NPC305039
0.71 Intermediate Similarity NPC118011
0.71 Intermediate Similarity NPC36668
0.7091 Intermediate Similarity NPC220705
0.7083 Intermediate Similarity NPC173609
0.7075 Intermediate Similarity NPC323441
0.7075 Intermediate Similarity NPC472685
0.7075 Intermediate Similarity NPC473384
0.7075 Intermediate Similarity NPC124211
0.7075 Intermediate Similarity NPC472702
0.7071 Intermediate Similarity NPC472007
0.7065 Intermediate Similarity NPC324762
0.7064 Intermediate Similarity NPC133422
0.7064 Intermediate Similarity NPC199107
0.7064 Intermediate Similarity NPC232969
0.7059 Intermediate Similarity NPC165383
0.7059 Intermediate Similarity NPC475302
0.7059 Intermediate Similarity NPC263780
0.7059 Intermediate Similarity NPC109414
0.7054 Intermediate Similarity NPC66108
0.7048 Intermediate Similarity NPC166770
0.7043 Intermediate Similarity NPC17772
0.7043 Intermediate Similarity NPC315974
0.7041 Intermediate Similarity NPC110405
0.7041 Intermediate Similarity NPC132228
0.7041 Intermediate Similarity NPC8518
0.7041 Intermediate Similarity NPC241512
0.7041 Intermediate Similarity NPC263997
0.7041 Intermediate Similarity NPC474680
0.7041 Intermediate Similarity NPC6185

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC31021 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
0.7379 Intermediate Similarity NPD5696 Approved
0.7374 Intermediate Similarity NPD5692 Phase 3
0.7347 Intermediate Similarity NPD6672 Approved
0.7347 Intermediate Similarity NPD5737 Approved
0.73 Intermediate Similarity NPD5694 Approved
0.73 Intermediate Similarity NPD6050 Approved
0.71 Intermediate Similarity NPD6080 Approved
0.71 Intermediate Similarity NPD6673 Approved
0.71 Intermediate Similarity NPD6904 Approved
0.7087 Intermediate Similarity NPD5695 Phase 3
0.703 Intermediate Similarity NPD5207 Approved
0.699 Remote Similarity NPD5282 Discontinued
0.6961 Remote Similarity NPD5693 Phase 1
0.6952 Remote Similarity NPD6084 Phase 2
0.6952 Remote Similarity NPD6083 Phase 2
0.6923 Remote Similarity NPD5654 Approved
0.6818 Remote Similarity NPD6008 Approved
0.6818 Remote Similarity NPD5739 Approved
0.6818 Remote Similarity NPD6402 Approved
0.6818 Remote Similarity NPD6675 Approved
0.6818 Remote Similarity NPD7128 Approved
0.68 Remote Similarity NPD6409 Approved
0.68 Remote Similarity NPD6684 Approved
0.68 Remote Similarity NPD7334 Approved
0.68 Remote Similarity NPD7521 Approved
0.68 Remote Similarity NPD7146 Approved
0.68 Remote Similarity NPD5330 Approved
0.68 Remote Similarity NPD6098 Approved
0.6792 Remote Similarity NPD5959 Approved
0.6786 Remote Similarity NPD6373 Approved
0.6786 Remote Similarity NPD6372 Approved
0.6765 Remote Similarity NPD6101 Approved
0.6765 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6765 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6762 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6757 Remote Similarity NPD5697 Approved
0.6757 Remote Similarity NPD5701 Approved
0.6737 Remote Similarity NPD4756 Discovery
0.6733 Remote Similarity NPD3573 Approved
0.6731 Remote Similarity NPD6399 Phase 3
0.67 Remote Similarity NPD1694 Approved
0.6696 Remote Similarity NPD7320 Approved
0.6696 Remote Similarity NPD6899 Approved
0.6696 Remote Similarity NPD6881 Approved
0.6696 Remote Similarity NPD6011 Approved
0.6667 Remote Similarity NPD6649 Approved
0.6667 Remote Similarity NPD6650 Approved
0.6667 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6903 Approved
0.6667 Remote Similarity NPD7900 Approved
0.6667 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6637 Remote Similarity NPD6012 Approved
0.6637 Remote Similarity NPD6013 Approved
0.6637 Remote Similarity NPD6014 Approved
0.6635 Remote Similarity NPD5284 Approved
0.6635 Remote Similarity NPD6411 Approved
0.6635 Remote Similarity NPD5281 Approved
0.6607 Remote Similarity NPD6614 Approved
0.6604 Remote Similarity NPD5210 Approved
0.6604 Remote Similarity NPD4629 Approved
0.6579 Remote Similarity NPD7290 Approved
0.6579 Remote Similarity NPD7102 Approved
0.6579 Remote Similarity NPD6883 Approved
0.6571 Remote Similarity NPD5778 Approved
0.6571 Remote Similarity NPD5779 Approved
0.6566 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6531 Remote Similarity NPD4695 Discontinued
0.6522 Remote Similarity NPD6617 Approved
0.6522 Remote Similarity NPD6869 Approved
0.6522 Remote Similarity NPD8130 Phase 1
0.6522 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6522 Remote Similarity NPD6847 Approved
0.6509 Remote Similarity NPD7748 Approved
0.6509 Remote Similarity NPD6001 Approved
0.6505 Remote Similarity NPD5208 Approved
0.6481 Remote Similarity NPD7902 Approved
0.6471 Remote Similarity NPD5280 Approved
0.6471 Remote Similarity NPD5279 Phase 3
0.6471 Remote Similarity NPD4694 Approved
0.6466 Remote Similarity NPD6882 Approved
0.6466 Remote Similarity NPD8297 Approved
0.6465 Remote Similarity NPD5369 Approved
0.6449 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6442 Remote Similarity NPD4753 Phase 2
0.6389 Remote Similarity NPD4697 Phase 3
0.6387 Remote Similarity NPD7115 Discovery
0.6374 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6319 Approved
0.633 Remote Similarity NPD4755 Approved
0.6325 Remote Similarity NPD6053 Discontinued
0.6321 Remote Similarity NPD7515 Phase 2
0.6311 Remote Similarity NPD3618 Phase 1
0.6311 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6303 Remote Similarity NPD6274 Approved
0.629 Remote Similarity NPD7492 Approved
0.6275 Remote Similarity NPD4197 Approved
0.6275 Remote Similarity NPD3668 Phase 3
0.6273 Remote Similarity NPD4225 Approved
0.625 Remote Similarity NPD6317 Approved
0.624 Remote Similarity NPD6616 Approved
0.6239 Remote Similarity NPD5222 Approved
0.6239 Remote Similarity NPD5221 Approved
0.6239 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6239 Remote Similarity NPD7732 Phase 3
0.6238 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6238 Remote Similarity NPD5209 Approved
0.6238 Remote Similarity NPD3667 Approved
0.623 Remote Similarity NPD6054 Approved
0.623 Remote Similarity NPD6059 Approved
0.6216 Remote Similarity NPD4700 Approved
0.6216 Remote Similarity NPD5286 Approved
0.6216 Remote Similarity NPD4696 Approved
0.6216 Remote Similarity NPD5285 Approved
0.6214 Remote Similarity NPD1696 Phase 3
0.6214 Remote Similarity NPD5329 Approved
0.6214 Remote Similarity NPD5363 Approved
0.6198 Remote Similarity NPD6314 Approved
0.6198 Remote Similarity NPD6335 Approved
0.6198 Remote Similarity NPD6313 Approved
0.6196 Remote Similarity NPD3704 Approved
0.6195 Remote Similarity NPD6052 Approved
0.619 Remote Similarity NPD7078 Approved
0.619 Remote Similarity NPD8293 Discontinued
0.6182 Remote Similarity NPD5173 Approved
0.6179 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6179 Remote Similarity NPD6016 Approved
0.6179 Remote Similarity NPD6015 Approved
0.6174 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6167 Remote Similarity NPD6868 Approved
0.6162 Remote Similarity NPD3617 Approved
0.6161 Remote Similarity NPD5223 Approved
0.6154 Remote Similarity NPD5786 Approved
0.6154 Remote Similarity NPD5690 Phase 2
0.6148 Remote Similarity NPD7100 Approved
0.6148 Remote Similarity NPD7101 Approved
0.6142 Remote Similarity NPD7736 Approved
0.6134 Remote Similarity NPD4632 Approved
0.6132 Remote Similarity NPD5328 Approved
0.6129 Remote Similarity NPD6370 Approved
0.6129 Remote Similarity NPD5988 Approved
0.6124 Remote Similarity NPD7260 Phase 2
0.6117 Remote Similarity NPD3666 Approved
0.6117 Remote Similarity NPD4786 Approved
0.6117 Remote Similarity NPD3665 Phase 1
0.6117 Remote Similarity NPD3133 Approved
0.6116 Remote Similarity NPD6009 Approved
0.6106 Remote Similarity NPD5224 Approved
0.6106 Remote Similarity NPD5211 Phase 2
0.6106 Remote Similarity NPD5225 Approved
0.6106 Remote Similarity NPD4633 Approved
0.6106 Remote Similarity NPD5226 Approved
0.608 Remote Similarity NPD8328 Phase 3
0.6078 Remote Similarity NPD4270 Approved
0.6078 Remote Similarity NPD4223 Phase 3
0.6078 Remote Similarity NPD4221 Approved
0.6078 Remote Similarity NPD4269 Approved
0.6075 Remote Similarity NPD5785 Approved
0.6058 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6053 Remote Similarity NPD4754 Approved
0.6053 Remote Similarity NPD5175 Approved
0.6053 Remote Similarity NPD5174 Approved
0.6048 Remote Similarity NPD6908 Approved
0.6048 Remote Similarity NPD5983 Phase 2
0.6048 Remote Similarity NPD6909 Approved
0.6048 Remote Similarity NPD8513 Phase 3
0.604 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6022 Remote Similarity NPD7331 Phase 2
0.602 Remote Similarity NPD8039 Approved
0.6019 Remote Similarity NPD6079 Approved
0.6019 Remote Similarity NPD7154 Phase 3
0.6017 Remote Similarity NPD4634 Approved
0.6 Remote Similarity NPD5141 Approved
0.5981 Remote Similarity NPD1695 Approved
0.5965 Remote Similarity NPD5091 Approved
0.5963 Remote Similarity NPD5133 Approved
0.5963 Remote Similarity NPD4202 Approved
0.5954 Remote Similarity NPD6845 Suspended
0.5952 Remote Similarity NPD7604 Phase 2
0.5948 Remote Similarity NPD4768 Approved
0.5948 Remote Similarity NPD4767 Approved
0.5946 Remote Similarity NPD7614 Phase 1
0.5922 Remote Similarity NPD6435 Approved
0.592 Remote Similarity NPD8516 Approved
0.592 Remote Similarity NPD8515 Approved
0.592 Remote Similarity NPD8517 Approved
0.5918 Remote Similarity NPD4687 Approved
0.5918 Remote Similarity NPD5733 Approved
0.5918 Remote Similarity NPD4058 Approved
0.5914 Remote Similarity NPD7341 Phase 2
0.5891 Remote Similarity NPD6033 Approved
0.5888 Remote Similarity NPD4518 Approved
0.5882 Remote Similarity NPD2067 Discontinued
0.5882 Remote Similarity NPD4252 Approved
0.5876 Remote Similarity NPD5276 Approved
0.5872 Remote Similarity NPD7983 Approved
0.587 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5865 Remote Similarity NPD6110 Phase 1
0.5859 Remote Similarity NPD6336 Discontinued
0.5849 Remote Similarity NPD4690 Approved
0.5849 Remote Similarity NPD4623 Approved

Structure

External Identifiers

PubChem CID   53355010
ChEMBL   CHEMBL1801780
ZINC  

Physicochemical Properties

Molecular Weight:  316.13
ALogP:  -0.4585
MLogP:  2.89
XLogP:  0.761
# Rotatable Bonds:  7
Polar Surface Area:  69.67
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  23

Download Data

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