NP-MRD: Showing NP-Card for 11-acetoxy-8-isobutyryl-4-guaien-3-one (NP0037585)

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Record Information

Version

2.0

Created at

2021-06-20 20:28:34 UTC

Updated at

2021-06-30 00:09:51 UTC

NP-MRD ID

NP0037585

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-acetoxy-8-isobutyryl-4-guaien-3-one

Provided By

JEOL Database JEOL Logo

Description

(3AR)-1,4beta-Dimethyl-6beta-(isobutyryloxy)-7beta-(1-acetoxy-1-methylethyl)-2,3,3abeta,4,5,6,7,8-octahydroazulene-2-one belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. 11-acetoxy-8-isobutyryl-4-guaien-3-one is found in Torilis japonica. 11-acetoxy-8-isobutyryl-4-guaien-3-one was first documented in 2008 (Lee, I.-K., et al.). Based on a literature review very few articles have been published on (3aR)-1,4beta-Dimethyl-6beta-(isobutyryloxy)-7beta-(1-acetoxy-1-methylethyl)-2,3,3abeta,4,5,6,7,8-octahydroazulene-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122283D          

 58 59  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202122283D          

 58 59  0  0  0  0            999 V2000
    0.2265    1.3172    4.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2466    1.1904    3.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6022    1.0997    5.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0295    0.6006    4.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5702    2.3378    4.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2629    3.4397    0.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4766    2.1937    0.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4652    2.6880   -0.6701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7631    1.2510    0.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9198    2.0148   -0.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1951    2.8888    0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9089   -0.0969    0.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2627    0.8159   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2569   -0.5916   -1.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2090    0.8337   -4.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2246    1.0673   -2.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5394    1.5836   -2.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9308   -3.2207   -1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0579   -3.7603   -2.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416   -2.9331   -2.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4396   -2.5373    0.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6412   -4.8467    1.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474   -5.0023   -0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7825   -4.8495   -0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0375   -3.2934    1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4846   -2.6904   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3361   -1.2333    2.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5914   -0.7019    1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1425   -1.7843    3.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7960   -2.2401    4.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9224   -2.9441    2.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8201    1.2101    2.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862    0.2541    4.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4635    0.7135    3.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0  0  0  0
 16 17  1  0  0  0  0
 13 14  2  0  0  0  0
 17 19  1  0  0  0  0
 11 12  1  0  0  0  0
 16 44  1  6  0  0  0
  9  8  1  0  0  0  0
  5  6  1  0  0  0  0
 10  9  1  0  0  0  0
  5  4  1  1  0  0  0
 16 15  1  0  0  0  0
  5  7  1  0  0  0  0
 15 13  1  0  0  0  0
  4  2  1  0  0  0  0
 13 11  1  0  0  0  0
  2  1  1  0  0  0  0
 11 10  2  0  0  0  0
  2  3  2  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
  8  5  1  0  0  0  0
 22 24  1  0  0  0  0
  8 20  1  0  0  0  0
 22 23  2  0  0  0  0
 20 21  1  0  0  0  0
 24 25  1  0  0  0  0
 10 16  1  0  0  0  0
 24 26  1  0  0  0  0
 17 45  1  1  0  0  0
  9 37  1  0  0  0  0
  9 38  1  0  0  0  0
 19 49  1  0  0  0  0
 19 50  1  0  0  0  0
  8 36  1  6  0  0  0
 20 51  1  1  0  0  0
 15 42  1  0  0  0  0
 15 43  1  0  0  0  0
 18 46  1  0  0  0  0
 18 47  1  0  0  0  0
 18 48  1  0  0  0  0
 12 39  1  0  0  0  0
 12 40  1  0  0  0  0
 12 41  1  0  0  0  0
  6 30  1  0  0  0  0
  6 31  1  0  0  0  0
  6 32  1  0  0  0  0
  7 33  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  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
 24 52  1  6  0  0  0
 25 53  1  0  0  0  0
 25 54  1  0  0  0  0
 25 55  1  0  0  0  0
 26 56  1  0  0  0  0
 26 57  1  0  0  0  0
 26 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0037585

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])([H])C(=O)OC(C([H])([H])[H])(C([H])([H])[H])[C@@]1([H])C([H])([H])C2=C(C(=O)C([H])([H])[C@]2([H])[C@@]([H])(C([H])([H])[H])C([H])([H])[C@@]1([H])OC(=O)C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O5/c1-11(2)20(24)25-19-8-12(3)15-10-18(23)13(4)16(15)9-17(19)21(6,7)26-14(5)22/h11-12,15,17,19H,8-10H2,1-7H3/t12-,15+,17-,19+/m0/s1

> <INCHI_KEY>
DCMJUVYIZMYNQN-MJFFMMMISA-N

> <FORMULA>
C21H32O5

> <MOLECULAR_WEIGHT>
364.482

> <EXACT_MASS>
364.22497413

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
40.679146912094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6R,8S,8aR)-5-[2-(acetyloxy)propan-2-yl]-3,8-dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-6-yl 2-methylpropanoate

> <ALOGPS_LOGP>
3.28

> <JCHEM_LOGP>
3.5304361839999987

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.791733596369522

> <JCHEM_POLAR_SURFACE_AREA>
69.67000000000002

> <JCHEM_REFRACTIVITY>
99.00919999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,6R,7S)-7-[2-(acetyloxy)propan-2-yl]-1,4-dimethyl-2-oxo-3a,4,5,6,7,8-hexahydro-3H-azulen-6-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 59  0  0  0  0  0  0  0  0999 V2000
    0.2265    1.3172    4.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2466    1.1904    3.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3831    0.8782    2.7773 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7775    1.4615    2.2462 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5843    1.4264    0.7998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4619    2.4933    0.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9345    1.9097    0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620   -0.0048    0.2914 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2871   -0.1608   -1.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8269   -1.0023   -1.8005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8435   -0.5442   -2.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2180    0.8057   -3.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6769   -1.7149   -2.8761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6577   -1.6642   -3.6031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1916   -2.9457   -2.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8482   -2.5012   -1.5823 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6604   -2.9738   -0.1182 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7907   -4.5049   -0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7249   -2.5770    0.4228 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8280   -1.1808    1.0598 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2378   -0.9220    1.2327 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7834   -1.2645    2.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1798   -1.7808    3.3646 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2491   -0.8814    2.4681 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0748   -2.0261    3.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4161    0.3951    3.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022    1.0997    5.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0295    0.6006    4.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5702    2.3378    4.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2629    3.4397    0.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4766    2.1937    0.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4652    2.6880   -0.6701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7631    1.2510    0.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9198    2.0148   -0.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1951    2.8888    0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9089   -0.0969    0.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2627    0.8159   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2569   -0.5916   -1.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2090    0.8337   -4.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2246    1.0673   -2.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5394    1.5836   -2.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9308   -3.2207   -1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0579   -3.7603   -2.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416   -2.9331   -2.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4396   -2.5373    0.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6412   -4.8467    1.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474   -5.0023   -0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7825   -4.8495   -0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0375   -3.2934    1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4846   -2.6904   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3361   -1.2333    2.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5914   -0.7019    1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1425   -1.7843    3.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7960   -2.2401    4.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9224   -2.9441    2.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8201    1.2101    2.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862    0.2541    4.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4635    0.7135    3.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 16 17  1  0
 13 14  2  0
 17 19  1  0
 11 12  1  0
 16 44  1  6
  9  8  1  0
  5  6  1  0
 10  9  1  0
  5  4  1  1
 16 15  1  0
  5  7  1  0
 15 13  1  0
  4  2  1  0
 13 11  1  0
  2  1  1  0
 11 10  2  0
  2  3  2  0
 19 20  1  0
 21 22  1  0
  8  5  1  0
 22 24  1  0
  8 20  1  0
 22 23  2  0
 20 21  1  0
 24 25  1  0
 10 16  1  0
 24 26  1  0
 17 45  1  1
  9 37  1  0
  9 38  1  0
 19 49  1  0
 19 50  1  0
  8 36  1  6
 20 51  1  1
 15 42  1  0
 15 43  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
  6 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 24 52  1  6
 25 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 26 58  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       0.227   1.317   4.515  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.247   1.190   3.099  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.383   0.878   2.777  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.778   1.462   2.246  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.584   1.426   0.800  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.462   2.493   0.407  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.935   1.910   0.228  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.162  -0.005   0.291  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.287  -0.161  -1.239  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.827  -1.002  -1.801  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.843  -0.544  -2.550  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.218   0.806  -3.035  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.677  -1.715  -2.876  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.658  -1.664  -3.603  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.192  -2.946  -2.182  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.848  -2.501  -1.582  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.660  -2.974  -0.118  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.791  -4.505  -0.028  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.725  -2.577   0.423  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.828  -1.181   1.060  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.238  -0.922   1.233  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.783  -1.264   2.434  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.180  -1.781   3.365  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.249  -0.881   2.468  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.075  -2.026   3.045  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.416   0.395   3.283  0.00  0.00           C+0
HETATM   27  H   UNK     0      -0.602   1.100   5.194  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.030   0.601   4.703  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.570   2.338   4.700  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.263   3.440   0.923  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.477   2.194   0.686  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.465   2.688  -0.670  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.763   1.251   0.494  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.920   2.015  -0.861  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.195   2.889   0.649  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.909  -0.097   0.525  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.263   0.816  -1.729  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.257  -0.592  -1.516  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.209   0.834  -4.129  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.225   1.067  -2.693  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.539   1.584  -2.678  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.931  -3.221  -1.423  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.058  -3.760  -2.899  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.042  -2.933  -2.192  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.440  -2.537   0.520  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.641  -4.847   1.002  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.047  -5.002  -0.661  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.783  -4.849  -0.335  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.038  -3.293   1.196  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.485  -2.690  -0.363  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.336  -1.233   2.039  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.591  -0.702   1.442  0.00  0.00           H+0
HETATM   53  H   UNK     0       6.143  -1.784   3.024  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.796  -2.240   4.083  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.922  -2.944   2.467  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.820   1.210   2.858  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.086   0.254   4.318  0.00  0.00           H+0
HETATM   58  H   UNK     0       5.463   0.714   3.299  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    6    4    7    8                                             
CONECT    6    5   30   31   32                                             
CONECT    7    5   33   34   35                                             
CONECT    8    9    5   20   36                                             
CONECT    9    8   10   37   38                                             
CONECT   10    9   11   16                                                  
CONECT   11   12   13   10                                                  
CONECT   12   11   39   40   41                                             
CONECT   13   14   15   11                                                  
CONECT   14   13                                                            
CONECT   15   16   13   42   43                                             
CONECT   16   17   44   15   10                                             
CONECT   17   18   16   19   45                                             
CONECT   18   17   46   47   48                                             
CONECT   19   17   20   49   50                                             
CONECT   20   19    8   21   51                                             
CONECT   21   22   20                                                       
CONECT   22   21   24   23                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   52                                             
CONECT   25   24   53   54   55                                             
CONECT   26   24   56   57   58                                             
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    6                                                            
CONECT   31    6                                                            
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34    7                                                            
CONECT   35    7                                                            
CONECT   36    8                                                            
CONECT   37    9                                                            
CONECT   38    9                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   12                                                            
CONECT   42   15                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   17                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   19                                                            
CONECT   51   20                                                            
CONECT   52   24                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   26                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
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
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   -3.2246    1.0673   -2.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5394    1.5836   -2.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9308   -3.2207   -1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0579   -3.7603   -2.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416   -2.9331   -2.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6412   -4.8467    1.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474   -5.0023   -0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7825   -4.8495   -0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0375   -3.2934    1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4846   -2.6904   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3361   -1.2333    2.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5914   -0.7019    1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1425   -1.7843    3.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7960   -2.2401    4.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9224   -2.9441    2.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8201    1.2101    2.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862    0.2541    4.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4635    0.7135    3.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 16 17  1  0
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 11 12  1  0
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  5  6  1  0
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  5  4  1  1
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  4  2  1  0
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  2  1  1  0
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  2  3  2  0
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  8 36  1  6
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  6 30  1  0
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  7 33  1  0
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 26 58  1  0
M  END

View in JSmol

Synonyms

Value	Source
(3AR)-1,4b-dimethyl-6b-(isobutyryloxy)-7b-(1-acetoxy-1-methylethyl)-2,3,3abeta,4,5,6,7,8-octahydroazulene-2-one	Generator
(3AR)-1,4β-dimethyl-6β-(isobutyryloxy)-7β-(1-acetoxy-1-methylethyl)-2,3,3abeta,4,5,6,7,8-octahydroazulene-2-one	Generator

Chemical Formula

C₂₁H₃₂O₅

Average Mass

364.4820 Da

Monoisotopic Mass

364.22497 Da

IUPAC Name

(5S,6R,8S,8aR)-5-[2-(acetyloxy)propan-2-yl]-3,8-dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-6-yl 2-methylpropanoate

Traditional Name

(3aR,4S,6R,7S)-7-[2-(acetyloxy)propan-2-yl]-1,4-dimethyl-2-oxo-3a,4,5,6,7,8-hexahydro-3H-azulen-6-yl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

[H]C([H])([H])C(=O)OC(C([H])([H])[H])(C([H])([H])[H])[C@@]1([H])C([H])([H])C2=C(C(=O)C([H])([H])[C@]2([H])[C@@]([H])(C([H])([H])[H])C([H])([H])[C@@]1([H])OC(=O)C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H32O5/c1-11(2)20(24)25-19-8-12(3)15-10-18(23)13(4)16(15)9-17(19)21(6,7)26-14(5)22/h11-12,15,17,19H,8-10H2,1-7H3/t12-,15+,17-,19+/m0/s1

InChI Key

DCMJUVYIZMYNQN-MJFFMMMISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Torilis japonica	JEOL database	Lee, I.-K., et al, Chem. Pharm. Bull. 56, 1483 (2008)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Guaianes

Alternative Parents

Substituents

Guaiane sesquiterpenoid
Dicarboxylic acid or derivatives
Cyclic ketone
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.28	ALOGPS
logP	3.53	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	99.01 m³·mol⁻¹	ChemAxon
Polarizability	40.68 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25112480

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lee, I.-K., et al. (2008). Lee, I.-K., et al, Chem. Pharm. Bull. 56, 1483 (2008). Chem. Pharm. Bull..

Showing NP-Card for 11-acetoxy-8-isobutyryl-4-guaien-3-one (NP0037585)

MOL for NP0037585 (11-acetoxy-8-isobutyryl-4-guaien-3-one)

3D MOL for NP0037585 (11-acetoxy-8-isobutyryl-4-guaien-3-one)

3D SDF for NP0037585 (11-acetoxy-8-isobutyryl-4-guaien-3-one)

3D-SDF for NP0037585 (11-acetoxy-8-isobutyryl-4-guaien-3-one)

PDB for NP0037585 (11-acetoxy-8-isobutyryl-4-guaien-3-one)

3D PDB for NP0037585 (11-acetoxy-8-isobutyryl-4-guaien-3-one)

SMILES for NP0037585 (11-acetoxy-8-isobutyryl-4-guaien-3-one)

INCHI for NP0037585 (11-acetoxy-8-isobutyryl-4-guaien-3-one)

Structure for NP0037585 (11-acetoxy-8-isobutyryl-4-guaien-3-one)

3D Structure for NP0037585 (11-acetoxy-8-isobutyryl-4-guaien-3-one)