NP-MRD: Showing NP-Card for komaroviquinone (NP0178091)

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Record Information

Version

2.0

Created at

2022-09-03 16:01:33 UTC

Updated at

2022-09-03 16:01:33 UTC

NP-MRD ID

NP0178091

Secondary Accession Numbers

None

Natural Product Identification

Common Name

komaroviquinone

Description

Komaroviquinone belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center. Komaroviquinone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. komaroviquinone was first documented in 2017 (PMID: 27896867). Based on a literature review a small amount of articles have been published on komaroviquinone (PMID: 31343172) (PMID: 35370208) (PMID: 30297108) (PMID: 28882484).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032218012D          

 26 29  0  0  1  0            999 V2000
    5.4179   -1.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6499   -1.6120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0050   -1.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1282   -0.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8963    0.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0195    0.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5411   -0.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4834    0.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6066    1.0487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7153   -0.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5921   -0.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -1.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1013   -0.5813    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6820   -1.3131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1422   -1.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5758   -0.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9788    0.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0884    0.9524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6449    0.1780    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2393    0.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0514    0.5082    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4827    1.2114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -0.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2370   -1.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1137   -2.2143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 13 24  1  6  0  0  0
 11 25  1  0  0  0  0
  3 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    4.5089   -0.2960    2.6795 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3830    0.0418    1.3182 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1794   -0.0854    0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1315    0.1232   -0.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2939    0.4906   -1.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5346    0.8275   -0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5867   -0.5250   -2.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8361   -0.0147   -1.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7090    0.1727   -2.5371 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6496   -0.3728   -0.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6921   -0.5824    0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438   -0.9421    1.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7327   -0.9394    0.5870 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8221   -1.8129    1.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0034   -1.8725    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2063   -0.6202   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649    0.6094    0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3343    0.6625    1.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0568    1.8443   -0.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1809    0.4534    0.2812 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5151    0.7369   -1.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6229   -0.4976   -1.2243 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4687   -0.7959   -2.5803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3825   -1.4889   -0.6533 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9744   -0.4473    1.4571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9946   -0.6514    2.6968 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5877   -0.1002    2.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2113   -1.3217    2.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9498    0.4138    3.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9991    1.4434   -2.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0729   -0.0102   -0.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2621    1.2655   -1.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3196    1.6777   -0.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6574   -1.0379   -2.8493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3622   -1.2419   -2.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9341    0.0372   -3.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6608   -0.2126    2.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4453   -1.9389    2.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3902   -2.8558    1.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0745   -1.5699    2.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9536   -2.1168    0.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8825   -2.7142   -0.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2769   -0.4854   -0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6607   -0.7000   -1.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9867    1.5613    1.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5619    0.7761    2.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9943   -0.2118    1.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4411    2.6351    0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9558    1.5879   -1.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2677    2.3121   -1.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8315    1.1760    1.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2159    0.7239   -1.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8884    1.6408   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8078   -0.0104   -3.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 13 12  1  1
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 11 25  1  0
 25 26  2  0
 25  3  1  0
 22 10  1  0
 20 13  1  0
 24 13  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
 12 37  1  0
 12 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  1
 21 52  1  0
 21 53  1  0
 23 54  1  0
M  END


  Mrv1652309032218012D          

 26 29  0  0  1  0            999 V2000
    5.4179   -1.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6499   -1.6120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0050   -1.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1282   -0.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8963    0.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0195    0.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5411   -0.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4834    0.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6066    1.0487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7153   -0.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5921   -0.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -1.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1013   -0.5813    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6820   -1.3131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1422   -1.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5758   -0.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9788    0.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0884    0.9524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6449    0.1780    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2393    0.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0514    0.5082    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4827    1.2114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -0.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2370   -1.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1137   -2.2143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 13 24  1  6  0  0  0
 11 25  1  0  0  0  0
  3 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0178091

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C(C)C)C(=O)C2=C(C[C@@]34CCCC(C)(C)[C@@H]3C[C@]2(O)O4)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O5/c1-11(2)14-17(23)15-12(16(22)18(14)25-5)9-20-8-6-7-19(3,4)13(20)10-21(15,24)26-20/h11,13,24H,6-10H2,1-5H3/t13-,20-,21-/m0/s1

> <INCHI_KEY>
DUWHKUPNNGPNFK-ZEWGMFERSA-N

> <FORMULA>
C21H28O5

> <MOLECULAR_WEIGHT>
360.45

> <EXACT_MASS>
360.193674002

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
39.14940232401054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9S,11S)-9-hydroxy-5-methoxy-12,12-dimethyl-6-(propan-2-yl)-16-oxatetracyclo[7.6.1.0^{1,11}.0^{3,8}]hexadeca-3(8),5-diene-4,7-dione

> <JCHEM_LOGP>
3.2682721800000007

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.20839122646824

> <JCHEM_PKA_STRONGEST_BASIC>
-4.301785729114628

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
98.678

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9S,11S)-9-hydroxy-6-isopropyl-5-methoxy-12,12-dimethyl-16-oxatetracyclo[7.6.1.0^{1,11}.0^{3,8}]hexadeca-3(8),5-diene-4,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      10.113  -2.447   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.680  -3.009   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.476  -2.048   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.706  -0.526   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.140   0.036   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.370   1.559   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.343  -0.924   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.502   0.435   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.732   1.958   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.069  -0.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.839  -1.650   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.298  -2.172   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.056  -1.085   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.273  -2.451   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.265  -2.448   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.075  -1.126   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.357   0.250   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.827   0.709   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.165   1.778   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.204   0.332   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.313   1.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.829   0.949   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.634   2.261   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.011  -0.107   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.042  -2.611   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.812  -4.133   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   22                                                  
CONECT   11   10   12   25                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20   24                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   13   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   10   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   13                                                       
CONECT   25   11    3   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
(+)-Komaroviquinone	ChEBI
Komarovispirone	MeSH

Chemical Formula

C₂₁H₂₈O₅

Average Mass

360.4500 Da

Monoisotopic Mass

360.19367 Da

IUPAC Name

(1S,9S,11S)-9-hydroxy-5-methoxy-12,12-dimethyl-6-(propan-2-yl)-16-oxatetracyclo[7.6.1.0^{1,11}.0^{3,8}]hexadeca-3(8),5-diene-4,7-dione

Traditional Name

(1S,9S,11S)-9-hydroxy-6-isopropyl-5-methoxy-12,12-dimethyl-16-oxatetracyclo[7.6.1.0^{1,11}.0^{3,8}]hexadeca-3(8),5-diene-4,7-dione

CAS Registry Number

Not Available

SMILES

COC1=C(C(C)C)C(=O)C2=C(C[C@@]34CCCC(C)(C)[C@@H]3C[C@]2(O)O4)C1=O

InChI Identifier

InChI=1S/C21H28O5/c1-11(2)14-17(23)15-12(16(22)18(14)25-5)9-20-8-6-7-19(3,4)13(20)10-21(15,24)26-20/h11,13,24H,6-10H2,1-5H3/t13-,20-,21-/m0/s1

InChI Key

DUWHKUPNNGPNFK-ZEWGMFERSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaphilones

Sub Class

Not Available

Direct Parent

Azaphilones

Alternative Parents

Substituents

Azaphilone
Pyran
Vinylogous ester
Tetrahydrofuran
Ketone
Hemiacetal
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

quinone (CHEBI:66148 )
bridged compound (CHEBI:66148 )
tetracyclic diterpenoid (CHEBI:66148 )
lactol (CHEBI:66148 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.27	ChemAxon
pKa (Strongest Acidic)	11.21	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	98.68 m³·mol⁻¹	ChemAxon
Polarizability	39.15 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00044849

Chemspider ID

552818

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

637171

PDB ID

Not Available

ChEBI ID

66148

Good Scents ID

Not Available

References

General References

Thommen C, Neuburger M, Gademann K: Collective Syntheses of Icetexane Natural Products Based on Biogenetic Hypotheses. Chemistry. 2017 Jan 1;23(1):120-127. doi: 10.1002/chem.201603932. Epub 2016 Nov 29. [PubMed:27896867 ]
Ahmad A, Burtoloso ACB: Total Synthesis of (+/-)-Brussonol and (+/-)-Komaroviquinone via a Regioselective Cross-Electrophile Coupling of Aryl Bromides and Epoxides. Org Lett. 2019 Aug 2;21(15):6079-6083. doi: 10.1021/acs.orglett.9b02221. Epub 2019 Jul 25. [PubMed:31343172 ]
Aoyagi Y, Fujiwara K, Takahashi Y, Yano R, Hitotsuyanagi Y, Takeya K, Aiyama R, Matsuzaki T, Hashimoto S, Nishihara-Tsukashima A, Namatame M, Ishiyama A, Iwatsuki M, Otoguro K, Yamada H, Omura S: Semisynthesis of Antitrypanosomal p-Quinone Analog Possesing the Komaroviquinone Pharmacophore. Chem Pharm Bull (Tokyo). 2022;70(4):300-303. doi: 10.1248/cpb.c21-00998. [PubMed:35370208 ]
Okayama M, Kitabatake S, Sato M, Fujimori K, Ichikawa D, Matsushita M, Suto Y, Iwasaki G, Yamada T, Kiuchi F, Hirao M, Kunieda H, Osada M, Okamoto S, Hattori Y: A novel derivative (GTN024) from a natural product, komaroviquinone, induced the apoptosis of high-risk myeloma cells via reactive oxygen production and ER stress. Biochem Biophys Res Commun. 2018 Nov 2;505(3):787-793. doi: 10.1016/j.bbrc.2018.09.177. Epub 2018 Oct 5. [PubMed:30297108 ]
Suto Y, Sato M, Fujimori K, Kitabatake S, Okayama M, Ichikawa D, Matsushita M, Yamagiwa N, Iwasaki G, Kiuchi F, Hattori Y: Synthesis and biological evaluation of the natural product komaroviquinone and related compounds aiming at a potential therapeutic lead compound for high-risk multiple myeloma. Bioorg Med Chem Lett. 2017 Oct 1;27(19):4558-4563. doi: 10.1016/j.bmcl.2017.08.054. Epub 2017 Aug 30. [PubMed:28882484 ]
LOTUS database [Link]

Showing NP-Card for komaroviquinone (NP0178091)

MOL for NP0178091 (komaroviquinone)

3D MOL for NP0178091 (komaroviquinone)

3D SDF for NP0178091 (komaroviquinone)

3D-SDF for NP0178091 (komaroviquinone)

PDB for NP0178091 (komaroviquinone)

3D PDB for NP0178091 (komaroviquinone)

SMILES for NP0178091 (komaroviquinone)

INCHI for NP0178091 (komaroviquinone)

Structure for NP0178091 (komaroviquinone)

3D Structure for NP0178091 (komaroviquinone)