NP-MRD: Showing NP-Card for 22-Deacetylyanuthone A (NP0003476)

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Record Information

Version

1.0

Created at

2020-12-09 00:42:59 UTC

Updated at

2021-07-15 16:46:30 UTC

NP-MRD ID

NP0003476

Secondary Accession Numbers

None

Natural Product Identification

Common Name

22-Deacetylyanuthone A

Provided By

NPAtlas

Description

22-Deacetylyanuthone A belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 22-Deacetylyanuthone A is found in Aspergillus niger. It was first documented in 2000 (PMID: 11031048). Based on a literature review a small amount of articles have been published on 22-deacetylyanuthone A (PMID: 25293978) (PMID: 24684908) (PMID: 27417331).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117473D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242117473D          

 58 59  0  0  0  0            999 V2000
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   -4.3893   -2.5798   -2.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9567   -1.1287   -0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7013    0.0254    0.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4029   -0.1350    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5233    1.5711   -0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8816    2.2032    0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6096    3.2477   -0.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3454    3.5948   -0.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3971    3.9950    0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0997    0.1682    1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2973    2.6293    0.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9742    0.6544   -0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7173   -0.3684    0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2754    3.1986    0.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3874    2.8524   -1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0865    2.3553   -0.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3973   -0.6864    0.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4221    0.5315    1.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3208    1.7431    0.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9711    1.4047   -1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1241    0.4155   -1.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9191   -0.3442   -2.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3350   -2.2078   -0.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7134   -0.8819    0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4932   -3.5832    0.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0515   -2.6439    1.5334 H   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
  2  4  2  3  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 16  1  0  0  0  0
 25 16  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
  4 33  1  0  0  0  0
  5 34  1  0  0  0  0
  5 35  1  0  0  0  0
  6 36  1  0  0  0  0
  6 37  1  0  0  0  0
  8 38  1  0  0  0  0
  8 39  1  0  0  0  0
  8 40  1  0  0  0  0
  9 41  1  0  0  0  0
 10 42  1  0  0  0  0
 10 43  1  0  0  0  0
 11 44  1  0  0  0  0
 11 45  1  0  0  0  0
 13 46  1  0  0  0  0
 13 47  1  0  0  0  0
 13 48  1  0  0  0  0
 14 49  1  0  0  0  0
 15 50  1  0  0  0  0
 15 51  1  0  0  0  0
 18 52  1  1  0  0  0
 19 53  1  6  0  0  0
 20 54  1  0  0  0  0
 22 55  1  0  0  0  0
 22 56  1  0  0  0  0
 23 57  1  0  0  0  0
 24 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003476

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C([H])C(=O)[C@@]2(O[C@]2([H])[C@]1([H])O[H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O4/c1-15(2)7-5-8-16(3)9-6-10-17(4)11-12-22-19(24)13-18(14-23)20(25)21(22)26-22/h7,9,11,13,20-21,23,25H,5-6,8,10,12,14H2,1-4H3/b16-9+,17-11+/t20-,21-,22+/m1/s1

> <INCHI_KEY>
NXKIAZOEVGWPKT-UXNGKKSFSA-N

> <FORMULA>
C22H32O4

> <MOLECULAR_WEIGHT>
360.494

> <EXACT_MASS>
360.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
42.35589800273269

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5R,6R)-5-hydroxy-4-(hydroxymethyl)-1-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-2-one

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
3.790639542999999

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.263685718737417

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.16520608983313

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7845162405331756

> <JCHEM_POLAR_SURFACE_AREA>
70.06

> <JCHEM_REFRACTIVITY>
107.39159999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,6R)-5-hydroxy-4-(hydroxymethyl)-1-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 59  0  0  0  0  0  0  0  0999 V2000
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    1.1557    2.4529   -0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3152   -0.3655   -1.0832 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4120   -0.9162   -2.3636 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0702   -1.7761    0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2561   -2.7086    1.0795 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7698   -1.9023    0.7695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3756   -1.5048    0.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4431   -2.2365    1.1328 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3971    3.9950    0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0997    0.1682    1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2973    2.6293    0.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0365    1.4993    1.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9742    0.6544   -0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7173   -0.3684    0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2754    3.1986    0.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3874    2.8524   -1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0865    2.3553   -0.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3973   -0.6864    0.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4221    0.5315    1.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3208    1.7431    0.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9711    1.4047   -1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1241    0.4155   -1.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9191   -0.3442   -2.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3350   -2.2078   -0.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7134   -0.8819    0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4932   -3.5832    0.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0515   -2.6439    1.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 16 15  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24 25  1  0
 25 26  2  0
 18 16  1  0
 25 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 13 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 18 52  1  1
 19 53  1  6
 20 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 24 58  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -7.341  -1.663  -0.603  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.880  -1.803  -0.783  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.347  -2.868  -1.649  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.020  -0.976  -0.169  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.586   0.089   0.700  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.204   1.456   0.303  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.829   1.887   0.377  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.524   3.282  -0.136  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.863   1.138   0.858  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.448   1.595   0.925  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.610   0.633   0.086  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.798   1.106   0.164  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.156   2.453  -0.308  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.720   0.292   0.667  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.153   0.687   0.781  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.043  -0.246  -0.013  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.837  -0.349  -1.386  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.992   0.297  -0.908  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.315  -0.366  -1.083  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.412  -0.916  -2.364  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.640  -1.361  -0.045  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.070  -1.776   0.079  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.256  -2.709   1.079  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.770  -1.902   0.770  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.376  -1.505   0.657  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.443  -2.236   1.133  0.00  0.00           O+0
HETATM   27  H   UNK     0      -7.718  -0.689  -0.989  0.00  0.00           H+0
HETATM   28  H   UNK     0      -7.666  -1.752   0.463  0.00  0.00           H+0
HETATM   29  H   UNK     0      -7.884  -2.429  -1.212  0.00  0.00           H+0
HETATM   30  H   UNK     0      -5.130  -3.817  -1.085  0.00  0.00           H+0
HETATM   31  H   UNK     0      -6.095  -3.084  -2.434  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.389  -2.580  -2.148  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.957  -1.129  -0.348  0.00  0.00           H+0
HETATM   34  H   UNK     0      -6.701   0.025   0.614  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.403  -0.135   1.782  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.523   1.571  -0.786  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.882   2.203   0.819  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.610   3.248  -0.800  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.345   3.595  -0.794  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.397   3.995   0.680  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.100   0.168   1.245  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.297   2.629   0.617  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.036   1.499   1.962  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.974   0.654  -0.953  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.717  -0.368   0.567  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.275   3.199   0.482  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.387   2.852  -1.026  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.087   2.355  -0.932  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.397  -0.686   0.998  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.422   0.532   1.863  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.321   1.743   0.575  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.971   1.405  -1.123  0.00  0.00           H+0
HETATM   53  H   UNK     0       7.124   0.416  -1.036  0.00  0.00           H+0
HETATM   54  H   UNK     0       5.919  -0.344  -2.994  0.00  0.00           H+0
HETATM   55  H   UNK     0       8.335  -2.208  -0.928  0.00  0.00           H+0
HETATM   56  H   UNK     0       8.713  -0.882   0.195  0.00  0.00           H+0
HETATM   57  H   UNK     0       8.493  -3.583   0.657  0.00  0.00           H+0
HETATM   58  H   UNK     0       6.051  -2.644   1.533  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    1    3    4                                                  
CONECT    3    2   30   31   32                                             
CONECT    4    2    5   33                                                  
CONECT    5    4    6   34   35                                             
CONECT    6    5    7   36   37                                             
CONECT    7    6    8    9                                                  
CONECT    8    7   38   39   40                                             
CONECT    9    7   10   41                                                  
CONECT   10    9   11   42   43                                             
CONECT   11   10   12   44   45                                             
CONECT   12   11   13   14                                                  
CONECT   13   12   46   47   48                                             
CONECT   14   12   15   49                                                  
CONECT   15   14   16   50   51                                             
CONECT   16   15   17   18   25                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   16   52                                             
CONECT   19   18   20   21   53                                             
CONECT   20   19   54                                                       
CONECT   21   19   22   24                                                  
CONECT   22   21   23   55   56                                             
CONECT   23   22   57                                                       
CONECT   24   21   25   58                                                  
CONECT   25   24   26   16                                                  
CONECT   26   25                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
CONECT   34    5                                                            
CONECT   35    5                                                            
CONECT   36    6                                                            
CONECT   37    6                                                            
CONECT   38    8                                                            
CONECT   39    8                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   10                                                            
CONECT   44   11                                                            
CONECT   45   11                                                            
CONECT   46   13                                                            
CONECT   47   13                                                            
CONECT   48   13                                                            
CONECT   49   14                                                            
CONECT   50   15                                                            
CONECT   51   15                                                            
CONECT   52   18                                                            
CONECT   53   19                                                            
CONECT   54   20                                                            
CONECT   55   22                                                            
CONECT   56   22                                                            
CONECT   57   23                                                            
CONECT   58   24                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  118    0
END

RDKit          3D

58 59  0  0  0  0  0  0  0  0999 V2000
   -7.3414   -1.6627   -0.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8802   -1.8034   -0.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3470   -2.8676   -1.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0198   -0.9763   -0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5857    0.0889    0.7003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2039    1.4565    0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8291    1.8871    0.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5242    3.2824   -0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8634    1.1377    0.8581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4485    1.5954    0.9247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6103    0.6327    0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7980    1.1056    0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1557    2.4529   -0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7196    0.2921    0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1534    0.6874    0.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0432   -0.2456   -0.0134 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8371   -0.3492   -1.3861 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925    0.2971   -0.9079 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3152   -0.3655   -1.0832 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4120   -0.9162   -2.3636 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6395   -1.3606   -0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0702   -1.7761    0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2561   -2.7086    1.0795 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7698   -1.9023    0.7695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3756   -1.5048    0.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4431   -2.2365    1.1328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7181   -0.6888   -0.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6657   -1.7524    0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8839   -2.4288   -1.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1301   -3.8171   -1.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0946   -3.0837   -2.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3893   -2.5798   -2.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9567   -1.1287   -0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7013    0.0254    0.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4029   -0.1350    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5233    1.5711   -0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8816    2.2032    0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6096    3.2477   -0.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3454    3.5948   -0.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3971    3.9950    0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0997    0.1682    1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2973    2.6293    0.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0365    1.4993    1.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9742    0.6544   -0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7173   -0.3684    0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2754    3.1986    0.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3874    2.8524   -1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0865    2.3553   -0.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3973   -0.6864    0.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4221    0.5315    1.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3208    1.7431    0.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9711    1.4047   -1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1241    0.4155   -1.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9191   -0.3442   -2.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3350   -2.2078   -0.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7134   -0.8819    0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4932   -3.5832    0.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0515   -2.6439    1.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 16 15  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24 25  1  0
 25 26  2  0
 18 16  1  0
 25 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 13 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 18 52  1  1
 19 53  1  6
 20 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 24 58  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₂H₃₂O₄

Average Mass

360.4940 Da

Monoisotopic Mass

360.23006 Da

IUPAC Name

(1R,5R,6R)-5-hydroxy-4-(hydroxymethyl)-1-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-2-one

Traditional Name

(1R,5R,6R)-5-hydroxy-4-(hydroxymethyl)-1-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-2-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\C[C@@]12O[C@@H]1[C@H](O)C(CO)=CC2=O

InChI Identifier

InChI=1S/C22H32O4/c1-15(2)7-5-8-16(3)9-6-10-17(4)11-12-22-19(24)13-18(14-23)20(25)21(22)26-22/h7,9,11,13,20-21,23,25H,5-6,8,10,12,14H2,1-4H3/b16-9+,17-11+/t20-,21-,22+/m1/s1

InChI Key

NXKIAZOEVGWPKT-UXNGKKSFSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus niger	NPAtlas	11031048

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Cyclohexenone
Ketone
Secondary alcohol
Dialkyl ether
Oxirane
Ether
Organoheterocyclic compound
Oxacycle
Organic oxide
Carbonyl group
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

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	3.55	ALOGPS
logP	3.79	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	13.17	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.06 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	107.39 m³·mol⁻¹	ChemAxon
Polarizability	42.36 Å³	ChemAxon
Number of Rings	2	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

NPAtlas ID

NPA015963

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10478255

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

133844

Good Scents ID

Not Available

References

General References

Bugni TS, Abbanat D, Bernan VS, Maiese WM, Greenstein M, Van Wagoner RM, Ireland CM: Yanuthones: novel metabolites from a marine isolate of Aspergillus niger. J Org Chem. 2000 Oct 20;65(21):7195-200. doi: 10.1021/jo0006831. [PubMed:11031048 ]
Petersen LM, Holm DK, Knudsen PB, Nielsen KF, Gotfredsen CH, Mortensen UH, Larsen TO: Characterization of four new antifungal yanuthones from Aspergillus niger. J Antibiot (Tokyo). 2015 Mar;68(3):201-5. doi: 10.1038/ja.2014.130. Epub 2014 Oct 8. [PubMed:25293978 ]
Holm DK, Petersen LM, Klitgaard A, Knudsen PB, Jarczynska ZD, Nielsen KF, Gotfredsen CH, Larsen TO, Mortensen UH: Molecular and chemical characterization of the biosynthesis of the 6-MSA-derived meroterpenoid yanuthone D in Aspergillus niger. Chem Biol. 2014 Apr 24;21(4):519-529. doi: 10.1016/j.chembiol.2014.01.013. Epub 2014 Mar 27. [PubMed:24684908 ]
He WJ, Zhou XJ, Qin XC, Mai YX, Lin XP, Liao SR, Yang B, Zhang T, Tu ZC, Wang JF, Liu Y: Quinone/hydroquinone meroterpenoids with antitubercular and cytotoxic activities produced by the sponge-derived fungus Gliomastix sp. ZSDS1-F7. Nat Prod Res. 2017 Mar;31(5):604-609. doi: 10.1080/14786419.2016.1207076. Epub 2016 Jul 15. [PubMed:27417331 ]

Showing NP-Card for 22-Deacetylyanuthone A (NP0003476)

MOL for NP0003476 (22-Deacetylyanuthone A)

3D MOL for NP0003476 (22-Deacetylyanuthone A)

3D SDF for NP0003476 (22-Deacetylyanuthone A)

3D-SDF for NP0003476 (22-Deacetylyanuthone A)

PDB for NP0003476 (22-Deacetylyanuthone A)

3D PDB for NP0003476 (22-Deacetylyanuthone A)

SMILES for NP0003476 (22-Deacetylyanuthone A)

INCHI for NP0003476 (22-Deacetylyanuthone A)

Structure for NP0003476 (22-Deacetylyanuthone A)

3D Structure for NP0003476 (22-Deacetylyanuthone A)