NP-MRD: Showing NP-Card for 7-deacetoxyyanuthone (NP0004995)

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Record Information

Version

2.0

Created at

2020-12-09 02:22:11 UTC

Updated at

2021-07-15 16:50:45 UTC

NP-MRD ID

NP0004995

Secondary Accession Numbers

NP0043823

Natural Product Identification

Common Name

7-deacetoxyyanuthone

Provided By

NPAtlas

Description

7-Deacetoxyyanuthone A belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 7-deacetoxyyanuthone is found in Penicillium chrysogenum, Penicillium sp. and Streptomyces nitrosporeus. 7-deacetoxyyanuthone was first documented in 2003 (PMID: 14640527). Based on a literature review a small amount of articles have been published on 7-deacetoxyyanuthone A (PMID: 15974609) (PMID: 27417331).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118153D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242118153D          

 57 58  0  0  0  0            999 V2000
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   -2.9064    0.9734   -2.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2123    1.8380   -1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5275   -0.1572    1.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1332    1.5842    1.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6244    1.1993    1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0481    0.7865   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0948   -0.2187    1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3701    0.6264    2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3320    2.8272    1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6871    1.6353    2.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5463    3.3734   -1.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    2.9374   -0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0369    1.7214   -1.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7562    1.7545    1.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2926    3.0884    0.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2767    2.3932   -1.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0447   -0.1223    1.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6925   -1.8816   -0.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6807   -3.1513    0.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6305   -2.5794   -0.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1382   -3.6044   -1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5476   -3.1514    0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1670   -0.5606   -1.7692 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
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 18 16  1  0  0  0  0
 24 16  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  4 32  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
  6 35  1  0  0  0  0
  6 36  1  0  0  0  0
  8 37  1  0  0  0  0
  8 38  1  0  0  0  0
  8 39  1  0  0  0  0
  9 40  1  0  0  0  0
 10 41  1  0  0  0  0
 10 42  1  0  0  0  0
 11 43  1  0  0  0  0
 11 44  1  0  0  0  0
 13 45  1  0  0  0  0
 13 46  1  0  0  0  0
 13 47  1  0  0  0  0
 14 48  1  0  0  0  0
 15 49  1  0  0  0  0
 15 50  1  0  0  0  0
 18 51  1  1  0  0  0
 19 52  1  6  0  0  0
 20 53  1  0  0  0  0
 22 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
M  END
> <DATABASE_ID>
NP0004995

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C(=C([H])C(=O)[C@@]2(O[C@]12[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])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O3/c1-15(2)8-6-9-16(3)10-7-11-17(4)12-13-22-19(23)14-18(5)20(24)21(22)25-22/h8,10,12,14,20-21,24H,6-7,9,11,13H2,1-5H3/b16-10+,17-12+/t20-,21-,22+/m1/s1

> <INCHI_KEY>
DKOXVDVXOYHFHV-ITGDQCKOSA-N

> <FORMULA>
C22H32O3

> <MOLECULAR_WEIGHT>
344.495

> <EXACT_MASS>
344.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
40.64738610188617

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5R,6R)-5-hydroxy-4-methyl-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>
4.86

> <JCHEM_LOGP>
5.071410699666666

> <ALOGPS_LOGS>
-4.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.453365946673362

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4724546430333296

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
105.6169

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,6R)-5-hydroxy-4-methyl-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

 57 58  0  0  0  0  0  0  0  0999 V2000
   -4.8253   -2.5814    0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7379   -1.4104    0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8293   -1.4105    1.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5846   -0.3775   -0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5444   -0.2627   -1.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6090    0.8915   -1.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8493    0.8356   -0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5674    0.8426    1.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5147    0.7902   -0.0937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7193    0.7335    1.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2012    1.8659    1.3972 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2446    2.1226    0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9403    2.5094   -1.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5149    2.0233    0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6354    2.2606   -0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4593    0.9781   -0.2305 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9939    0.6371    1.1077 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9743   -0.1776    0.4028 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4367   -1.5323   -0.0186 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3528   -2.4470    1.0292 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7428   -1.5504   -0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5822   -2.8022   -0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1829   -0.4698   -1.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4075    0.7716   -1.3416 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5929    1.5495   -2.2883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9194   -3.0228   -0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7787   -2.2961    0.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1280   -3.3673    0.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7762   -1.8644    0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1243   -0.3588    1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5652   -1.9905    2.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2776    0.4798   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9713   -1.2003   -1.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0787   -0.0603   -2.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9064    0.9734   -2.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2123    1.8380   -1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5275   -0.1572    1.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1332    1.5842    1.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6244    1.1993    1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0481    0.7865   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0948   -0.2187    1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3701    0.6264    2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3320    2.8272    1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6871    1.6353    2.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5463    3.3734   -1.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    2.9374   -0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0369    1.7214   -1.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7562    1.7545    1.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2926    3.0884    0.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2767    2.3932   -1.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0447   -0.1223    1.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6925   -1.8816   -0.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6807   -3.1513    0.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6305   -2.5794   -0.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1382   -3.6044   -1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5476   -3.1514    0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1670   -0.5606   -1.7692 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
 21 23  2  0
 23 24  1  0
 24 25  2  0
 18 16  1  0
 24 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 13 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 18 51  1  1
 19 52  1  6
 20 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  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      -4.825  -2.581   0.191  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.738  -1.410   0.285  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.829  -1.411   1.290  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.585  -0.378  -0.514  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.544  -0.263  -1.545  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.609   0.892  -1.332  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.849   0.836  -0.062  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.567   0.843   1.220  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.515   0.790  -0.094  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.719   0.734   1.120  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.201   1.866   1.397  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.245   2.123   0.383  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.940   2.509  -1.008  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.515   2.023   0.754  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.635   2.261  -0.192  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.459   0.978  -0.231  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.994   0.637   1.108  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.974  -0.178   0.403  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.437  -1.532  -0.019  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.353  -2.447   1.029  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.743  -1.550  -0.681  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.582  -2.802  -0.661  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.183  -0.470  -1.294  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.407   0.772  -1.342  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.593   1.550  -2.288  0.00  0.00           O+0
HETATM   26  H   UNK     0      -4.919  -3.023  -0.827  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.779  -2.296   0.428  0.00  0.00           H+0
HETATM   28  H   UNK     0      -5.128  -3.367   0.902  0.00  0.00           H+0
HETATM   29  H   UNK     0      -7.776  -1.864   0.886  0.00  0.00           H+0
HETATM   30  H   UNK     0      -7.124  -0.359   1.557  0.00  0.00           H+0
HETATM   31  H   UNK     0      -6.565  -1.990   2.205  0.00  0.00           H+0
HETATM   32  H   UNK     0      -6.278   0.480  -0.433  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.971  -1.200  -1.696  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.079  -0.060  -2.517  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.906   0.973  -2.191  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.212   1.838  -1.286  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.527  -0.157   1.681  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.133   1.584   1.948  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.624   1.199   1.103  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.048   0.787  -1.066  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.095  -0.219   1.173  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.370   0.626   2.038  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.332   2.827   1.594  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.687   1.635   2.391  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.546   3.373  -1.371  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.109   2.937  -0.987  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.037   1.721  -1.753  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.756   1.755   1.802  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.293   3.088   0.140  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.277   2.393  -1.231  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.045  -0.122   1.013  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.692  -1.882  -0.795  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.681  -3.151   0.867  0.00  0.00           H+0
HETATM   54  H   UNK     0       7.630  -2.579  -0.872  0.00  0.00           H+0
HETATM   55  H   UNK     0       6.138  -3.604  -1.261  0.00  0.00           H+0
HETATM   56  H   UNK     0       6.548  -3.151   0.410  0.00  0.00           H+0
HETATM   57  H   UNK     0       7.167  -0.561  -1.769  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    1    3    4                                                  
CONECT    3    2   29   30   31                                             
CONECT    4    2    5   32                                                  
CONECT    5    4    6   33   34                                             
CONECT    6    5    7   35   36                                             
CONECT    7    6    8    9                                                  
CONECT    8    7   37   38   39                                             
CONECT    9    7   10   40                                                  
CONECT   10    9   11   41   42                                             
CONECT   11   10   12   43   44                                             
CONECT   12   11   13   14                                                  
CONECT   13   12   45   46   47                                             
CONECT   14   12   15   48                                                  
CONECT   15   14   16   49   50                                             
CONECT   16   15   17   18   24                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   16   51                                             
CONECT   19   18   20   21   52                                             
CONECT   20   19   53                                                       
CONECT   21   19   22   23                                                  
CONECT   22   21   54   55   56                                             
CONECT   23   21   24   57                                                  
CONECT   24   23   25   16                                                  
CONECT   25   24                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36    6                                                            
CONECT   37    8                                                            
CONECT   38    8                                                            
CONECT   39    8                                                            
CONECT   40    9                                                            
CONECT   41   10                                                            
CONECT   42   10                                                            
CONECT   43   11                                                            
CONECT   44   11                                                            
CONECT   45   13                                                            
CONECT   46   13                                                            
CONECT   47   13                                                            
CONECT   48   14                                                            
CONECT   49   15                                                            
CONECT   50   15                                                            
CONECT   51   18                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   22                                                            
CONECT   55   22                                                            
CONECT   56   22                                                            
CONECT   57   23                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  116    0
END

RDKit          3D

57 58  0  0  0  0  0  0  0  0999 V2000
   -4.8253   -2.5814    0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7379   -1.4104    0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8293   -1.4105    1.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5846   -0.3775   -0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5444   -0.2627   -1.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6090    0.8915   -1.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8493    0.8356   -0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5674    0.8426    1.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5147    0.7902   -0.0937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7193    0.7335    1.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2012    1.8659    1.3972 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2446    2.1226    0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9403    2.5094   -1.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5149    2.0233    0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6354    2.2606   -0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4593    0.9781   -0.2305 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9939    0.6371    1.1077 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9743   -0.1776    0.4028 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4367   -1.5323   -0.0186 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3528   -2.4470    1.0292 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7428   -1.5504   -0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5822   -2.8022   -0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1829   -0.4698   -1.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4075    0.7716   -1.3416 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5929    1.5495   -2.2883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9194   -3.0228   -0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7787   -2.2961    0.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1280   -3.3673    0.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7762   -1.8644    0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1243   -0.3588    1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5652   -1.9905    2.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2776    0.4798   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9713   -1.2003   -1.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0787   -0.0603   -2.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9064    0.9734   -2.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2123    1.8380   -1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5275   -0.1572    1.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1332    1.5842    1.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6244    1.1993    1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0481    0.7865   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0948   -0.2187    1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3701    0.6264    2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3320    2.8272    1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6871    1.6353    2.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5463    3.3734   -1.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    2.9374   -0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0369    1.7214   -1.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7562    1.7545    1.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2926    3.0884    0.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2767    2.3932   -1.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0447   -0.1223    1.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6925   -1.8816   -0.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6807   -3.1513    0.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6305   -2.5794   -0.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1382   -3.6044   -1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5476   -3.1514    0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1670   -0.5606   -1.7692 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
 21 23  2  0
 23 24  1  0
 24 25  2  0
 18 16  1  0
 24 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 13 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 18 51  1  1
 19 52  1  6
 20 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
M  END

View in JSmol View NMR Assignments View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₂H₃₂O₃

Average Mass

344.4950 Da

Monoisotopic Mass

344.23514 Da

IUPAC Name

(1R,5R,6R)-5-hydroxy-4-methyl-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-methyl-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(C)=CC2=O

InChI Identifier

InChI=1S/C22H32O3/c1-15(2)8-6-9-16(3)10-7-11-17(4)12-13-22-19(23)14-18(5)20(24)21(22)25-22/h8,10,12,14,20-21,24H,6-7,9,11,13H2,1-5H3/b16-10+,17-12+/t20-,21-,22+/m1/s1

InChI Key

DKOXVDVXOYHFHV-ITGDQCKOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Penicillium chrysogenum	LOTUS Database	35616633
Penicillium sp.	NPAtlas	14640527
Streptomyces nitrosporeus	LOTUS Database	35616633

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
Secondary alcohol
Ketone
Dialkyl ether
Oxirane
Oxacycle
Organoheterocyclic compound
Ether
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	4.86	ALOGPS
logP	5.07	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	13.45	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	105.62 m³·mol⁻¹	ChemAxon
Polarizability	40.65 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA011299

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00044483

Chemspider ID

8535604

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10360155

PDB ID

Not Available

ChEBI ID

133843

Good Scents ID

Not Available

References

General References

Li X, Choi HD, Kang JS, Lee CO, Son BW: New polyoxygenated farnesylcyclohexenones, deacetoxyyanuthone A and its hydro derivative from the marine-derived fungus Penicillium sp. J Nat Prod. 2003 Nov;66(11):1499-500. doi: 10.1021/np030231u. [PubMed:14640527 ]
Maskey RP, Grun-Wollny I, Laatsch H: Sorbicillin analogues and related dimeric compounds from Penicillium notatum. J Nat Prod. 2005 Jun;68(6):865-70. doi: 10.1021/np040137t. [PubMed:15974609 ]
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 7-deacetoxyyanuthone (NP0004995)

MOL for NP0004995 (7-deacetoxyyanuthone)

3D MOL for NP0004995 (7-deacetoxyyanuthone)

3D SDF for NP0004995 (7-deacetoxyyanuthone)

3D-SDF for NP0004995 (7-deacetoxyyanuthone)

PDB for NP0004995 (7-deacetoxyyanuthone)

3D PDB for NP0004995 (7-deacetoxyyanuthone)

SMILES for NP0004995 (7-deacetoxyyanuthone)

INCHI for NP0004995 (7-deacetoxyyanuthone)

Structure for NP0004995 (7-deacetoxyyanuthone)

3D Structure for NP0004995 (7-deacetoxyyanuthone)