Natural Product: NPC473658

Natural Product ID:  NPC473658
Common Name:   Sequoiatone F
IUPAC Name:   methyl (6E,7R)-7-hydroxy-3,7-dimethyl-6-[(3S)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate
Synonyms:   Sequoiatone F
Molecular Formula:   C22H30O5
Standard InCHIKey:  AZRKTTNHSKOLMR-JVEVTSHPSA-N
Standard InCHI:  InChI=1S/C22H30O5/c1-6-7-8-9-10-14(2)19(23)12-17-20(21(24)26-5)16-11-15(3)27-13-18(16)22(17,4)25/h11-14,25H,6-10H2,1-5H3/b17-12+/t14-,22+/m0/s1
Canonical SMILES:  CCCCCC[C@@H](C(=O)/C=C/1C(=C2C(=COC(=C2)C)[C@]1(C)O)C(=O)OC)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
NPO23190 Aspergillus parasiticus Species Aspergillaceae Eukaryota PMID[11678666]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT140 Organism Artemia Artemia LD50 = 260 nM 23305465

  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 NPC473658 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
0.988 High Similarity NPC307092
0.9759 High Similarity NPC26078
0.9643 High Similarity NPC51358
0.8434 Intermediate Similarity NPC316324
0.8 Intermediate Similarity NPC234038
0.8 Intermediate Similarity NPC315394
0.7907 Intermediate Similarity NPC93763
0.7907 Intermediate Similarity NPC315765
0.7907 Intermediate Similarity NPC108816
0.7802 Intermediate Similarity NPC316426
0.7802 Intermediate Similarity NPC315395
0.7802 Intermediate Similarity NPC475461
0.7802 Intermediate Similarity NPC305475
0.7778 Intermediate Similarity NPC14575
0.7778 Intermediate Similarity NPC197835
0.7778 Intermediate Similarity NPC196487
0.7778 Intermediate Similarity NPC141193
0.7778 Intermediate Similarity NPC140591
0.7778 Intermediate Similarity NPC303653
0.7778 Intermediate Similarity NPC189609
0.7778 Intermediate Similarity NPC291500
0.7778 Intermediate Similarity NPC96259
0.7766 Intermediate Similarity NPC166110
0.7742 Intermediate Similarity NPC212598
0.7742 Intermediate Similarity NPC268298
0.7717 Intermediate Similarity NPC72513
0.7711 Intermediate Similarity NPC316029
0.7711 Intermediate Similarity NPC315597
0.7711 Intermediate Similarity NPC315285
0.7708 Intermediate Similarity NPC91408
0.7701 Intermediate Similarity NPC267231
0.7692 Intermediate Similarity NPC255307
0.7692 Intermediate Similarity NPC165162
0.7684 Intermediate Similarity NPC248193
0.7677 Intermediate Similarity NPC469851
0.767 Intermediate Similarity NPC228477
0.767 Intermediate Similarity NPC137911
0.7667 Intermediate Similarity NPC40746
0.7667 Intermediate Similarity NPC169575
0.7667 Intermediate Similarity NPC16488
0.766 Intermediate Similarity NPC166554
0.766 Intermediate Similarity NPC129419
0.766 Intermediate Similarity NPC179394
0.766 Intermediate Similarity NPC144133
0.766 Intermediate Similarity NPC265856
0.764 Intermediate Similarity NPC325031
0.7634 Intermediate Similarity NPC260343
0.7609 Intermediate Similarity NPC116575
0.7609 Intermediate Similarity NPC122502
0.7604 Intermediate Similarity NPC477131
0.7604 Intermediate Similarity NPC470013
0.7604 Intermediate Similarity NPC323008
0.7604 Intermediate Similarity NPC53685
0.7604 Intermediate Similarity NPC198853
0.7604 Intermediate Similarity NPC262133
0.7604 Intermediate Similarity NPC470010
0.7586 Intermediate Similarity NPC116177
0.7586 Intermediate Similarity NPC7563
0.7586 Intermediate Similarity NPC320630
0.7582 Intermediate Similarity NPC114979
0.7582 Intermediate Similarity NPC476804
0.7582 Intermediate Similarity NPC191476
0.7579 Intermediate Similarity NPC111114
0.7579 Intermediate Similarity NPC300312
0.7579 Intermediate Similarity NPC261607
0.7556 Intermediate Similarity NPC85772
0.7553 Intermediate Similarity NPC115179
0.7553 Intermediate Similarity NPC106040
0.7553 Intermediate Similarity NPC142159
0.7553 Intermediate Similarity NPC95364
0.7551 Intermediate Similarity NPC208094
0.7527 Intermediate Similarity NPC113370
0.7527 Intermediate Similarity NPC103743
0.7527 Intermediate Similarity NPC237540
0.7527 Intermediate Similarity NPC476079
0.7527 Intermediate Similarity NPC160138
0.7527 Intermediate Similarity NPC472007
0.7526 Intermediate Similarity NPC295347
0.7526 Intermediate Similarity NPC304886
0.75 Intermediate Similarity NPC261380
0.75 Intermediate Similarity NPC469657
0.75 Intermediate Similarity NPC474369
0.75 Intermediate Similarity NPC470755
0.75 Intermediate Similarity NPC228451
0.75 Intermediate Similarity NPC471223
0.75 Intermediate Similarity NPC244456
0.75 Intermediate Similarity NPC475838
0.75 Intermediate Similarity NPC78089
0.75 Intermediate Similarity NPC307112
0.75 Intermediate Similarity NPC128276
0.75 Intermediate Similarity NPC192006
0.75 Intermediate Similarity NPC125290
0.75 Intermediate Similarity NPC67081
0.75 Intermediate Similarity NPC476049
0.75 Intermediate Similarity NPC125674
0.7476 Intermediate Similarity NPC469853
0.7474 Intermediate Similarity NPC77337
0.7474 Intermediate Similarity NPC475855
0.7473 Intermediate Similarity NPC131669
0.7473 Intermediate Similarity NPC473390
0.7473 Intermediate Similarity NPC250315
0.7471 Intermediate Similarity NPC473223
0.747 Intermediate Similarity NPC313444
0.7451 Intermediate Similarity NPC309190
0.7451 Intermediate Similarity NPC472868
0.7449 Intermediate Similarity NPC172998
0.7449 Intermediate Similarity NPC299396
0.7449 Intermediate Similarity NPC301596
0.7447 Intermediate Similarity NPC476805
0.7447 Intermediate Similarity NPC475819
0.7444 Intermediate Similarity NPC42470
0.7444 Intermediate Similarity NPC24417
0.7444 Intermediate Similarity NPC52861
0.7444 Intermediate Similarity NPC25684
0.7444 Intermediate Similarity NPC471325
0.7444 Intermediate Similarity NPC301477
0.7444 Intermediate Similarity NPC141810
0.7444 Intermediate Similarity NPC281949
0.7444 Intermediate Similarity NPC112868
0.7442 Intermediate Similarity NPC476355
0.7442 Intermediate Similarity NPC227396
0.7426 Intermediate Similarity NPC471599
0.7423 Intermediate Similarity NPC167219
0.7423 Intermediate Similarity NPC474247
0.7423 Intermediate Similarity NPC477241
0.7423 Intermediate Similarity NPC474338
0.7419 Intermediate Similarity NPC203795
0.7419 Intermediate Similarity NPC469483
0.7419 Intermediate Similarity NPC261721
0.7419 Intermediate Similarity NPC198314
0.7419 Intermediate Similarity NPC107787
0.7419 Intermediate Similarity NPC150755
0.7419 Intermediate Similarity NPC472009
0.7419 Intermediate Similarity NPC164393
0.7416 Intermediate Similarity NPC178277
0.7416 Intermediate Similarity NPC63649
0.7416 Intermediate Similarity NPC270126
0.7416 Intermediate Similarity NPC472965
0.7416 Intermediate Similarity NPC264227
0.7396 Intermediate Similarity NPC45579
0.7396 Intermediate Similarity NPC193396
0.7396 Intermediate Similarity NPC133698
0.7396 Intermediate Similarity NPC472705
0.7396 Intermediate Similarity NPC32944
0.7391 Intermediate Similarity NPC243618
0.7391 Intermediate Similarity NPC115786
0.7391 Intermediate Similarity NPC295799
0.7391 Intermediate Similarity NPC82297
0.7391 Intermediate Similarity NPC158756
0.7391 Intermediate Similarity NPC470918
0.7391 Intermediate Similarity NPC31086
0.7391 Intermediate Similarity NPC70424
0.7386 Intermediate Similarity NPC86917
0.7386 Intermediate Similarity NPC472014
0.7386 Intermediate Similarity NPC57744
0.7386 Intermediate Similarity NPC187568
0.7386 Intermediate Similarity NPC471225
0.7386 Intermediate Similarity NPC41780
0.7381 Intermediate Similarity NPC232812
0.7381 Intermediate Similarity NPC67608
0.7379 Intermediate Similarity NPC469852
0.7374 Intermediate Similarity NPC239895
0.7374 Intermediate Similarity NPC69385
0.7374 Intermediate Similarity NPC20066
0.7368 Intermediate Similarity NPC218927
0.7368 Intermediate Similarity NPC295312
0.7368 Intermediate Similarity NPC36668
0.7368 Intermediate Similarity NPC118011
0.7368 Intermediate Similarity NPC206001
0.7363 Intermediate Similarity NPC229825
0.7363 Intermediate Similarity NPC89555
0.7363 Intermediate Similarity NPC474252
0.7363 Intermediate Similarity NPC173609
0.7356 Intermediate Similarity NPC244166
0.7353 Intermediate Similarity NPC25666
0.7353 Intermediate Similarity NPC271059
0.7347 Intermediate Similarity NPC272050
0.7347 Intermediate Similarity NPC209355
0.7347 Intermediate Similarity NPC67584
0.7347 Intermediate Similarity NPC234339
0.7347 Intermediate Similarity NPC273197
0.7347 Intermediate Similarity NPC20546
0.734 Intermediate Similarity NPC312561
0.734 Intermediate Similarity NPC142583
0.7333 Intermediate Similarity NPC160582
0.7333 Intermediate Similarity NPC47951
0.7327 Intermediate Similarity NPC206079
0.7327 Intermediate Similarity NPC219038
0.7326 Intermediate Similarity NPC238948
0.7326 Intermediate Similarity NPC12815
0.7326 Intermediate Similarity NPC215745
0.732 Intermediate Similarity NPC469692
0.732 Intermediate Similarity NPC59646
0.732 Intermediate Similarity NPC273579
0.732 Intermediate Similarity NPC472871
0.732 Intermediate Similarity NPC475912
0.732 Intermediate Similarity NPC288240
0.732 Intermediate Similarity NPC162205
0.732 Intermediate Similarity NPC135776
0.732 Intermediate Similarity NPC295204

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC473658 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
0.7667 Intermediate Similarity NPD7154 Phase 3
0.7586 Intermediate Similarity NPD4756 Discovery
0.7474 Intermediate Similarity NPD5785 Approved
0.7473 Intermediate Similarity NPD5362 Discontinued
0.7312 Intermediate Similarity NPD5363 Approved
0.7174 Intermediate Similarity NPD4270 Approved
0.7174 Intermediate Similarity NPD4269 Approved
0.7113 Intermediate Similarity NPD6698 Approved
0.7113 Intermediate Similarity NPD46 Approved
0.7103 Intermediate Similarity NPD6371 Approved
0.7065 Intermediate Similarity NPD5369 Approved
0.7053 Intermediate Similarity NPD5786 Approved
0.7041 Intermediate Similarity NPD5281 Approved
0.7041 Intermediate Similarity NPD5284 Approved
0.7 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.6972 Remote Similarity NPD6053 Discontinued
0.6961 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6957 Remote Similarity NPD4252 Approved
0.6957 Remote Similarity NPD4821 Approved
0.6957 Remote Similarity NPD4820 Approved
0.6957 Remote Similarity NPD4822 Approved
0.6957 Remote Similarity NPD4819 Approved
0.6947 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5784 Clinical (unspecified phase)
0.69 Remote Similarity NPD5282 Discontinued
0.6837 Remote Similarity NPD1695 Approved
0.6822 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6809 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6809 Remote Similarity NPD5209 Approved
0.6778 Remote Similarity NPD8039 Approved
0.6774 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6739 Remote Similarity NPD4268 Approved
0.6739 Remote Similarity NPD4271 Approved
0.6737 Remote Similarity NPD5332 Approved
0.6737 Remote Similarity NPD5331 Approved
0.6702 Remote Similarity NPD4790 Discontinued
0.6701 Remote Similarity NPD4249 Approved
0.67 Remote Similarity NPD7983 Approved
0.6667 Remote Similarity NPD5695 Phase 3
0.6635 Remote Similarity NPD5696 Approved
0.6634 Remote Similarity NPD6399 Phase 3
0.6634 Remote Similarity NPD5778 Approved
0.6634 Remote Similarity NPD5779 Approved
0.6633 Remote Similarity NPD4250 Approved
0.6633 Remote Similarity NPD4251 Approved
0.6632 Remote Similarity NPD6435 Approved
0.6628 Remote Similarity NPD7331 Phase 2
0.66 Remote Similarity NPD7838 Discovery
0.6598 Remote Similarity NPD1694 Approved
0.6596 Remote Similarity NPD5368 Approved
0.6579 Remote Similarity NPD7115 Discovery
0.6538 Remote Similarity NPD6084 Phase 2
0.6538 Remote Similarity NPD6083 Phase 2
0.6535 Remote Similarity NPD5693 Phase 1
0.6512 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6495 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6476 Remote Similarity NPD4225 Approved
0.6458 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6442 Remote Similarity NPD7839 Suspended
0.6437 Remote Similarity NPD3704 Approved
0.6436 Remote Similarity NPD5207 Approved
0.6436 Remote Similarity NPD5692 Phase 3
0.6429 Remote Similarity NPD1696 Phase 3
0.6429 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6429 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6415 Remote Similarity NPD7639 Approved
0.6415 Remote Similarity NPD7640 Approved
0.64 Remote Similarity NPD4518 Approved
0.6373 Remote Similarity NPD7637 Suspended
0.6373 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6373 Remote Similarity NPD6050 Approved
0.6373 Remote Similarity NPD5694 Approved
0.6364 Remote Similarity NPD5280 Approved
0.6364 Remote Similarity NPD5279 Phase 3
0.6364 Remote Similarity NPD4623 Approved
0.6364 Remote Similarity NPD4694 Approved
0.6364 Remote Similarity NPD4519 Discontinued
0.6339 Remote Similarity NPD2067 Discontinued
0.6337 Remote Similarity NPD6101 Approved
0.6337 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6337 Remote Similarity NPD5370 Suspended
0.6337 Remote Similarity NPD4753 Phase 2
0.6337 Remote Similarity NPD7285 Clinical (unspecified phase)
0.633 Remote Similarity NPD5909 Discontinued
0.6322 Remote Similarity NPD7341 Phase 2
0.6321 Remote Similarity NPD7638 Approved
0.6289 Remote Similarity NPD4223 Phase 3
0.6289 Remote Similarity NPD4221 Approved
0.6279 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6273 Remote Similarity NPD5739 Approved
0.6273 Remote Similarity NPD6402 Approved
0.6273 Remote Similarity NPD7128 Approved
0.6273 Remote Similarity NPD6675 Approved
0.6262 Remote Similarity NPD6648 Approved
0.625 Remote Similarity NPD6373 Approved
0.625 Remote Similarity NPD4695 Discontinued
0.625 Remote Similarity NPD6372 Approved
0.6239 Remote Similarity NPD6647 Phase 2
0.6238 Remote Similarity NPD5737 Approved
0.6238 Remote Similarity NPD6672 Approved
0.6226 Remote Similarity NPD7902 Approved
0.6224 Remote Similarity NPD6110 Phase 1
0.6218 Remote Similarity NPD8513 Phase 3
0.6216 Remote Similarity NPD5697 Approved
0.6216 Remote Similarity NPD5701 Approved
0.6214 Remote Similarity NPD6411 Approved
0.62 Remote Similarity NPD6409 Approved
0.62 Remote Similarity NPD7334 Approved
0.62 Remote Similarity NPD7146 Approved
0.62 Remote Similarity NPD6684 Approved
0.62 Remote Similarity NPD7521 Approved
0.62 Remote Similarity NPD5330 Approved
0.619 Remote Similarity NPD6356 Clinical (unspecified phase)
0.619 Remote Similarity NPD5210 Approved
0.619 Remote Similarity NPD4629 Approved
0.6176 Remote Similarity NPD6080 Approved
0.6176 Remote Similarity NPD6904 Approved
0.6176 Remote Similarity NPD6673 Approved
0.6162 Remote Similarity NPD3665 Phase 1
0.6162 Remote Similarity NPD3133 Approved
0.6162 Remote Similarity NPD4197 Approved
0.6162 Remote Similarity NPD3666 Approved
0.6161 Remote Similarity NPD7320 Approved
0.6161 Remote Similarity NPD6899 Approved
0.6161 Remote Similarity NPD6686 Approved
0.6161 Remote Similarity NPD6881 Approved
0.6161 Remote Similarity NPD6011 Approved
0.6154 Remote Similarity NPD4202 Approved
0.6147 Remote Similarity NPD5211 Phase 2
0.614 Remote Similarity NPD7116 Clinical (unspecified phase)
0.614 Remote Similarity NPD6650 Approved
0.614 Remote Similarity NPD6649 Approved
0.6126 Remote Similarity NPD6008 Approved
0.6117 Remote Similarity NPD4096 Approved
0.6106 Remote Similarity NPD6013 Approved
0.6106 Remote Similarity NPD6014 Approved
0.6106 Remote Similarity NPD6012 Approved
0.61 Remote Similarity NPD5329 Approved
0.6095 Remote Similarity NPD7748 Approved
0.6083 Remote Similarity NPD8516 Approved
0.6083 Remote Similarity NPD8515 Approved
0.6083 Remote Similarity NPD8517 Approved
0.6082 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6078 Remote Similarity NPD5208 Approved
0.6078 Remote Similarity NPD6903 Approved
0.6078 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6075 Remote Similarity NPD4755 Approved
0.6067 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6058 Remote Similarity NPD7515 Phase 2
0.6055 Remote Similarity NPD5344 Discontinued
0.6053 Remote Similarity NPD7290 Approved
0.6053 Remote Similarity NPD6883 Approved
0.6053 Remote Similarity NPD7102 Approved
0.6047 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6042 Remote Similarity NPD7322 Clinical (unspecified phase)
0.604 Remote Similarity NPD5205 Approved
0.604 Remote Similarity NPD5690 Phase 2
0.604 Remote Similarity NPD4690 Approved
0.604 Remote Similarity NPD3618 Phase 1
0.604 Remote Similarity NPD4689 Approved
0.604 Remote Similarity NPD4693 Phase 3
0.604 Remote Similarity NPD4688 Approved
0.604 Remote Similarity NPD4138 Approved
0.6038 Remote Similarity NPD5654 Approved
0.6036 Remote Similarity NPD5141 Approved
0.6017 Remote Similarity NPD7500 Approved
0.6 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6 Remote Similarity NPD6869 Approved
0.6 Remote Similarity NPD6617 Approved
0.6 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6 Remote Similarity NPD6847 Approved
0.6 Remote Similarity NPD8130 Phase 1
0.6 Remote Similarity NPD4786 Approved
0.5977 Remote Similarity NPD4194 Approved
0.5977 Remote Similarity NPD4193 Approved
0.5977 Remote Similarity NPD4192 Approved
0.5977 Remote Similarity NPD4191 Approved
0.5963 Remote Similarity NPD4700 Approved
0.5963 Remote Similarity NPD5286 Approved
0.5963 Remote Similarity NPD4696 Approved
0.5963 Remote Similarity NPD6404 Discontinued
0.5963 Remote Similarity NPD5285 Approved
0.596 Remote Similarity NPD3667 Approved
0.595 Remote Similarity NPD7503 Approved
0.5948 Remote Similarity NPD6882 Approved
0.5948 Remote Similarity NPD8297 Approved
0.5943 Remote Similarity NPD7900 Approved
0.5943 Remote Similarity NPD6001 Approved
0.5943 Remote Similarity NPD5122 Clinical (unspecified phase)
0.5943 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5932 Remote Similarity NPD690 Clinical (unspecified phase)
0.5926 Remote Similarity NPD5959 Approved
0.5918 Remote Similarity NPD7332 Phase 2
0.5913 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5909 Remote Similarity NPD5223 Approved
0.5906 Remote Similarity NPD7260 Phase 2
0.59 Remote Similarity NPD4788 Approved
0.59 Remote Similarity NPD6695 Phase 3
0.5897 Remote Similarity NPD4632 Approved

Structure

External Identifiers

PubChem CID   15382209
ChEMBL   CHEMBL448254
ZINC  

Physicochemical Properties

Molecular Weight:  374.21
ALogP:  -0.8089
MLogP:  3.33
XLogP:  3.695
# Rotatable Bonds:  15
Polar Surface Area:  72.83
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  27

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs