Natural Product: NPC67254

Natural Product ID:  NPC67254
Common Name:   (2R,3S,4R)-2,3,4-Trihydroxy-3-Methyl-6-(6-Methylhept-5-En-2-Ylidene)Cyclohexanone
IUPAC Name:   (2R,3S,4R,6E)-2,3,4-trihydroxy-3-methyl-6-(6-methylhept-5-en-2-ylidene)cyclohexan-1-one
Synonyms:  
Molecular Formula:   C15H24O4
Standard InCHIKey:  NLHKOAOSUWNDDM-NRIAAUITSA-N
Standard InCHI:  InChI=1S/C15H24O4/c1-9(2)6-5-7-10(3)11-8-12(16)15(4,19)14(18)13(11)17/h6,12,14,16,18-19H,5,7-8H2,1-4H3/b11-10+/t12-,14+,15+/m1/s1
Canonical SMILES:  CC(=CCC/C(=C/1C[C@@H](O)[C@]([C@H](C1=O)O)(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
NPO31059 Penicillium Genus Aspergillaceae Eukaryota PMID[15332861]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT277 Individual Protein Caspase-1 Homo sapiens MIC50 = 30000 nM 23316950
NPT567 Individual Protein Matrix metalloproteinase 3 Homo sapiens MIC50 = 300 nM 11754614

  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 NPC67254 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
0.8675 High Similarity NPC262026
0.8222 Intermediate Similarity NPC279722
0.7742 Intermediate Similarity NPC236176
0.7738 Intermediate Similarity NPC470947
0.7738 Intermediate Similarity NPC470945
0.7738 Intermediate Similarity NPC470946
0.7701 Intermediate Similarity NPC79573
0.7701 Intermediate Similarity NPC187529
0.7674 Intermediate Similarity NPC477786
0.7674 Intermediate Similarity NPC477784
0.7674 Intermediate Similarity NPC477785
0.7586 Intermediate Similarity NPC136114
0.7473 Intermediate Similarity NPC469464
0.7419 Intermediate Similarity NPC478089
0.7391 Intermediate Similarity NPC146852
0.7381 Intermediate Similarity NPC82666
0.7381 Intermediate Similarity NPC97173
0.7363 Intermediate Similarity NPC473100
0.7353 Intermediate Similarity NPC476023
0.7326 Intermediate Similarity NPC472948
0.7312 Intermediate Similarity NPC61275
0.7294 Intermediate Similarity NPC478122
0.7284 Intermediate Similarity NPC107848
0.7283 Intermediate Similarity NPC473099
0.7253 Intermediate Similarity NPC472008
0.7245 Intermediate Similarity NPC478176
0.7241 Intermediate Similarity NPC275766
0.7234 Intermediate Similarity NPC298919
0.7234 Intermediate Similarity NPC196227
0.7234 Intermediate Similarity NPC258674
0.7222 Intermediate Similarity NPC196381
0.7204 Intermediate Similarity NPC116726
0.7204 Intermediate Similarity NPC230623
0.7204 Intermediate Similarity NPC142838
0.7184 Intermediate Similarity NPC146945
0.7184 Intermediate Similarity NPC171888
0.7159 Intermediate Similarity NPC253364
0.7143 Intermediate Similarity NPC472007
0.7143 Intermediate Similarity NPC179659
0.7113 Intermediate Similarity NPC306908
0.7113 Intermediate Similarity NPC471144
0.7097 Intermediate Similarity NPC477684
0.7093 Intermediate Similarity NPC231739
0.7075 Intermediate Similarity NPC207217
0.7071 Intermediate Similarity NPC474747
0.7071 Intermediate Similarity NPC39996
0.7065 Intermediate Similarity NPC476707
0.7065 Intermediate Similarity NPC476708
0.7065 Intermediate Similarity NPC476706
0.7053 Intermediate Similarity NPC103527
0.7048 Intermediate Similarity NPC208998
0.7048 Intermediate Similarity NPC7921
0.7033 Intermediate Similarity NPC472009
0.7021 Intermediate Similarity NPC475441
0.701 Intermediate Similarity NPC20066
0.7009 Intermediate Similarity NPC470854
0.7009 Intermediate Similarity NPC122033
0.7009 Intermediate Similarity NPC474654
0.7009 Intermediate Similarity NPC97908
0.7009 Intermediate Similarity NPC287343
0.7 Intermediate Similarity NPC475945
0.7 Intermediate Similarity NPC474251
0.7 Intermediate Similarity NPC118902
0.7 Intermediate Similarity NPC104161
0.7 Intermediate Similarity NPC469809
0.7 Intermediate Similarity NPC469980
0.7 Intermediate Similarity NPC137163
0.7 Intermediate Similarity NPC191892
0.7 Intermediate Similarity NPC475871
0.699 Remote Similarity NPC163004
0.6979 Remote Similarity NPC476245
0.6979 Remote Similarity NPC272617
0.6977 Remote Similarity NPC471061
0.697 Remote Similarity NPC112613
0.697 Remote Similarity NPC47880
0.697 Remote Similarity NPC474742
0.697 Remote Similarity NPC472753
0.697 Remote Similarity NPC470184
0.6961 Remote Similarity NPC43285
0.6961 Remote Similarity NPC58370
0.6957 Remote Similarity NPC471738
0.6944 Remote Similarity NPC251310
0.6944 Remote Similarity NPC17772
0.6939 Remote Similarity NPC475284
0.6939 Remote Similarity NPC278008
0.6939 Remote Similarity NPC281608
0.6939 Remote Similarity NPC300584
0.6915 Remote Similarity NPC265856
0.6915 Remote Similarity NPC316228
0.6915 Remote Similarity NPC131864
0.6915 Remote Similarity NPC471399
0.6915 Remote Similarity NPC166554
0.6907 Remote Similarity NPC8803
0.69 Remote Similarity NPC472754
0.69 Remote Similarity NPC149371
0.6897 Remote Similarity NPC321180
0.6893 Remote Similarity NPC29827
0.6889 Remote Similarity NPC471987
0.6889 Remote Similarity NPC251475
0.6889 Remote Similarity NPC169941
0.6889 Remote Similarity NPC64600
0.6887 Remote Similarity NPC477266
0.6887 Remote Similarity NPC49451
0.6887 Remote Similarity NPC108721
0.6887 Remote Similarity NPC73300
0.6882 Remote Similarity NPC87189
0.6882 Remote Similarity NPC228415
0.6875 Remote Similarity NPC114162
0.6875 Remote Similarity NPC469819
0.6869 Remote Similarity NPC475949
0.6863 Remote Similarity NPC471332
0.6863 Remote Similarity NPC471333
0.686 Remote Similarity NPC477708
0.686 Remote Similarity NPC474197
0.6857 Remote Similarity NPC474229
0.6854 Remote Similarity NPC286229
0.6854 Remote Similarity NPC159714
0.6854 Remote Similarity NPC221510
0.6852 Remote Similarity NPC27999
0.6852 Remote Similarity NPC477116
0.6842 Remote Similarity NPC172101
0.6842 Remote Similarity NPC476705
0.6837 Remote Similarity NPC20078
0.6837 Remote Similarity NPC473574
0.6837 Remote Similarity NPC27105
0.6837 Remote Similarity NPC273269
0.6832 Remote Similarity NPC320294
0.6832 Remote Similarity NPC475873
0.6832 Remote Similarity NPC117185
0.6832 Remote Similarity NPC472755
0.6827 Remote Similarity NPC470257
0.6827 Remote Similarity NPC87335
0.6822 Remote Similarity NPC80650
0.6818 Remote Similarity NPC113363
0.6818 Remote Similarity NPC471740
0.6813 Remote Similarity NPC219966
0.6804 Remote Similarity NPC41070
0.6804 Remote Similarity NPC473170
0.68 Remote Similarity NPC128733
0.68 Remote Similarity NPC207885
0.68 Remote Similarity NPC133907
0.68 Remote Similarity NPC185141
0.68 Remote Similarity NPC84042
0.68 Remote Similarity NPC110443
0.68 Remote Similarity NPC46998
0.68 Remote Similarity NPC305085
0.68 Remote Similarity NPC476270
0.6796 Remote Similarity NPC165873
0.6796 Remote Similarity NPC144854
0.6796 Remote Similarity NPC477916
0.6796 Remote Similarity NPC3316
0.6796 Remote Similarity NPC266514
0.6796 Remote Similarity NPC474716
0.6792 Remote Similarity NPC474516
0.679 Remote Similarity NPC472072
0.6789 Remote Similarity NPC204552
0.6789 Remote Similarity NPC188667
0.6782 Remote Similarity NPC47844
0.6782 Remote Similarity NPC473536
0.6782 Remote Similarity NPC141195
0.6774 Remote Similarity NPC472324
0.6774 Remote Similarity NPC23622
0.6774 Remote Similarity NPC298904
0.6771 Remote Similarity NPC288240
0.6771 Remote Similarity NPC162205
0.6771 Remote Similarity NPC273579
0.6771 Remote Similarity NPC469645
0.6771 Remote Similarity NPC469692
0.6771 Remote Similarity NPC295204
0.6768 Remote Similarity NPC472687
0.6768 Remote Similarity NPC177232
0.6768 Remote Similarity NPC203388
0.6768 Remote Similarity NPC35717
0.6768 Remote Similarity NPC471331
0.6768 Remote Similarity NPC471330
0.6768 Remote Similarity NPC212465
0.6768 Remote Similarity NPC99657
0.6768 Remote Similarity NPC470541
0.6765 Remote Similarity NPC474741
0.6765 Remote Similarity NPC284865
0.6765 Remote Similarity NPC472756
0.6762 Remote Similarity NPC235077
0.6759 Remote Similarity NPC96312
0.6759 Remote Similarity NPC251236
0.6759 Remote Similarity NPC40632
0.6759 Remote Similarity NPC328374
0.6757 Remote Similarity NPC102822
0.6757 Remote Similarity NPC477046
0.6747 Remote Similarity NPC10758
0.6747 Remote Similarity NPC250928
0.6744 Remote Similarity NPC114236
0.6744 Remote Similarity NPC60718
0.6742 Remote Similarity NPC30675
0.6739 Remote Similarity NPC77971
0.6739 Remote Similarity NPC32037
0.6739 Remote Similarity NPC21469
0.6737 Remote Similarity NPC230332
0.6737 Remote Similarity NPC134321
0.6737 Remote Similarity NPC473619
0.6737 Remote Similarity NPC128672

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC67254 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
0.7079 Intermediate Similarity NPD6110 Phase 1
0.6875 Remote Similarity NPD5282 Discontinued
0.679 Remote Similarity NPD7331 Phase 2
0.6762 Remote Similarity NPD4634 Approved
0.65 Remote Similarity NPD4755 Approved
0.6495 Remote Similarity NPD7983 Approved
0.642 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6413 Remote Similarity NPD4800 Clinical (unspecified phase)
0.64 Remote Similarity NPD4697 Phase 3
0.6392 Remote Similarity NPD46 Approved
0.6392 Remote Similarity NPD6698 Approved
0.6386 Remote Similarity NPD3704 Approved
0.6374 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6373 Remote Similarity NPD5285 Approved
0.6373 Remote Similarity NPD5286 Approved
0.6373 Remote Similarity NPD4700 Approved
0.6373 Remote Similarity NPD4696 Approved
0.6304 Remote Similarity NPD5369 Approved
0.63 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6289 Remote Similarity NPD4753 Phase 2
0.6265 Remote Similarity NPD7341 Phase 2
0.6263 Remote Similarity NPD5779 Approved
0.6263 Remote Similarity NPD5778 Approved
0.6262 Remote Similarity NPD5345 Clinical (unspecified phase)
0.625 Remote Similarity NPD5225 Approved
0.625 Remote Similarity NPD5224 Approved
0.625 Remote Similarity NPD4633 Approved
0.625 Remote Similarity NPD5211 Phase 2
0.625 Remote Similarity NPD5226 Approved
0.6238 Remote Similarity NPD5222 Approved
0.6238 Remote Similarity NPD5221 Approved
0.6238 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6228 Remote Similarity NPD6319 Approved
0.6211 Remote Similarity NPD5363 Approved
0.6196 Remote Similarity NPD4695 Discontinued
0.619 Remote Similarity NPD5174 Approved
0.619 Remote Similarity NPD5175 Approved
0.6176 Remote Similarity NPD5173 Approved
0.6168 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6154 Remote Similarity NPD5223 Approved
0.6146 Remote Similarity NPD3618 Phase 1
0.6146 Remote Similarity NPD5786 Approved
0.6146 Remote Similarity NPD5279 Phase 3
0.6145 Remote Similarity NPD3197 Phase 1
0.6139 Remote Similarity NPD5210 Approved
0.6139 Remote Similarity NPD4629 Approved
0.6132 Remote Similarity NPD5141 Approved
0.6126 Remote Similarity NPD4632 Approved
0.6122 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6122 Remote Similarity NPD5328 Approved
0.6122 Remote Similarity NPD6101 Approved
0.6117 Remote Similarity NPD4225 Approved
0.6087 Remote Similarity NPD6059 Approved
0.6087 Remote Similarity NPD6054 Approved
0.6078 Remote Similarity NPD7839 Suspended
0.6075 Remote Similarity NPD5739 Approved
0.6075 Remote Similarity NPD7128 Approved
0.6075 Remote Similarity NPD4767 Approved
0.6075 Remote Similarity NPD6675 Approved
0.6075 Remote Similarity NPD4768 Approved
0.6075 Remote Similarity NPD6402 Approved
0.6068 Remote Similarity NPD8328 Phase 3
0.6064 Remote Similarity NPD4270 Approved
0.6064 Remote Similarity NPD4269 Approved
0.6055 Remote Similarity NPD6372 Approved
0.6055 Remote Similarity NPD6373 Approved
0.6042 Remote Similarity NPD1696 Phase 3
0.6042 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6038 Remote Similarity NPD4754 Approved
0.6034 Remote Similarity NPD6016 Approved
0.6034 Remote Similarity NPD6015 Approved
0.6022 Remote Similarity NPD5368 Approved
0.6022 Remote Similarity NPD4252 Approved
0.6019 Remote Similarity NPD5701 Approved
0.6019 Remote Similarity NPD5697 Approved
0.6 Remote Similarity NPD6079 Approved
0.6 Remote Similarity NPD6371 Approved
0.6 Remote Similarity NPD5344 Discontinued
0.6 Remote Similarity NPD6411 Approved
0.5983 Remote Similarity NPD5988 Approved
0.5983 Remote Similarity NPD6370 Approved
0.5979 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5963 Remote Similarity NPD4730 Approved
0.5963 Remote Similarity NPD4729 Approved
0.5963 Remote Similarity NPD5128 Approved
0.5963 Remote Similarity NPD6899 Approved
0.5963 Remote Similarity NPD7320 Approved
0.5963 Remote Similarity NPD6881 Approved
0.5955 Remote Similarity NPD4732 Discontinued
0.5946 Remote Similarity NPD6649 Approved
0.5946 Remote Similarity NPD6650 Approved
0.5938 Remote Similarity NPD3133 Approved
0.5938 Remote Similarity NPD3665 Phase 1
0.5938 Remote Similarity NPD3666 Approved
0.593 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5918 Remote Similarity NPD7524 Approved
0.5909 Remote Similarity NPD6014 Approved
0.5909 Remote Similarity NPD6012 Approved
0.5909 Remote Similarity NPD6013 Approved
0.59 Remote Similarity NPD5785 Approved
0.5895 Remote Similarity NPD6435 Approved
0.5895 Remote Similarity NPD3667 Approved
0.5893 Remote Similarity NPD8297 Approved
0.5882 Remote Similarity NPD7492 Approved
0.587 Remote Similarity NPD4756 Discovery
0.5865 Remote Similarity NPD6084 Phase 2
0.5865 Remote Similarity NPD6083 Phase 2
0.5862 Remote Similarity NPD4522 Approved
0.5856 Remote Similarity NPD5247 Approved
0.5856 Remote Similarity NPD5251 Approved
0.5856 Remote Similarity NPD6883 Approved
0.5856 Remote Similarity NPD7102 Approved
0.5856 Remote Similarity NPD7290 Approved
0.5856 Remote Similarity NPD5249 Phase 3
0.5856 Remote Similarity NPD5250 Approved
0.5856 Remote Similarity NPD5248 Approved
0.5842 Remote Similarity NPD7637 Suspended
0.5842 Remote Similarity NPD7515 Phase 2
0.5842 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5833 Remote Similarity NPD6616 Approved
0.5826 Remote Similarity NPD7115 Discovery
0.5826 Remote Similarity NPD6009 Approved
0.5825 Remote Similarity NPD5695 Phase 3
0.5818 Remote Similarity NPD6011 Approved
0.5816 Remote Similarity NPD6422 Discontinued
0.5814 Remote Similarity NPD6108 Clinical (unspecified phase)
0.581 Remote Similarity NPD5696 Approved
0.5804 Remote Similarity NPD5217 Approved
0.5804 Remote Similarity NPD8130 Phase 1
0.5804 Remote Similarity NPD5216 Approved
0.5804 Remote Similarity NPD6617 Approved
0.5804 Remote Similarity NPD6847 Approved
0.5804 Remote Similarity NPD6869 Approved
0.5804 Remote Similarity NPD5215 Approved
0.5785 Remote Similarity NPD7078 Approved
0.5785 Remote Similarity NPD8293 Discontinued
0.5784 Remote Similarity NPD4202 Approved
0.5773 Remote Similarity NPD4197 Approved
0.5773 Remote Similarity NPD4786 Approved
0.5761 Remote Similarity NPD819 Approved
0.5761 Remote Similarity NPD818 Approved
0.5752 Remote Similarity NPD6882 Approved
0.5743 Remote Similarity NPD7838 Discovery
0.5738 Remote Similarity NPD7736 Approved
0.5727 Remote Similarity NPD6412 Phase 2
0.5714 Remote Similarity NPD5135 Approved
0.5714 Remote Similarity NPD5329 Approved
0.5714 Remote Similarity NPD5134 Clinical (unspecified phase)
0.5714 Remote Similarity NPD368 Approved
0.5714 Remote Similarity NPD5169 Approved
0.5699 Remote Similarity NPD6932 Approved
0.569 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5684 Remote Similarity NPD4820 Approved
0.5684 Remote Similarity NPD4821 Approved
0.5684 Remote Similarity NPD4819 Approved
0.5684 Remote Similarity NPD6931 Approved
0.5684 Remote Similarity NPD4822 Approved
0.5684 Remote Similarity NPD6930 Phase 2
0.5679 Remote Similarity NPD73 Approved
0.5676 Remote Similarity NPD5168 Approved
0.567 Remote Similarity NPD6695 Phase 3
0.567 Remote Similarity NPD7154 Phase 3
0.5664 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5664 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5664 Remote Similarity NPD5127 Approved
0.566 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5658 Remote Similarity NPD9005 Phase 3
0.5658 Remote Similarity NPD9003 Clinical (unspecified phase)
0.5658 Remote Similarity NPD9004 Approved
0.5657 Remote Similarity NPD5690 Phase 2
0.5657 Remote Similarity NPD5280 Approved
0.5657 Remote Similarity NPD4694 Approved
0.5644 Remote Similarity NPD5370 Suspended
0.5641 Remote Similarity NPD9002 Approved
0.5641 Remote Similarity NPD9001 Clinical (unspecified phase)
0.5641 Remote Similarity NPD7641 Discontinued
0.5638 Remote Similarity NPD4268 Approved
0.5638 Remote Similarity NPD4271 Approved
0.5636 Remote Similarity NPD6008 Approved
0.563 Remote Similarity NPD8516 Approved
0.563 Remote Similarity NPD5983 Phase 2
0.563 Remote Similarity NPD8517 Approved
0.563 Remote Similarity NPD6921 Approved
0.563 Remote Similarity NPD8515 Approved
0.563 Remote Similarity NPD8513 Phase 3
0.5625 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5612 Remote Similarity NPD7338 Clinical (unspecified phase)
0.561 Remote Similarity NPD6033 Approved
0.5607 Remote Similarity NPD6648 Approved
0.5603 Remote Similarity NPD6274 Approved

Structure

External Identifiers

PubChem CID   11437103
ChEMBL   CHEMBL465411
ZINC  

Physicochemical Properties

Molecular Weight:  268.17
ALogP:  0.9576
MLogP:  2.67
XLogP:  2.109
# Rotatable Bonds:  10
Polar Surface Area:  77.76
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  1
# Heavy Atoms:  19

Download Data

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