NP-MRD: Showing NP-Card for (3r,3as,7as)-3-hexanoyl-6,7a-dimethyl-5-(2-oxopentyl)-3a,4-dihydro-3h-1-benzofuran-2,7-dione (NP0267039)

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Record Information

Version

2.0

Created at

2022-09-08 11:41:15 UTC

Updated at

2022-09-08 11:41:15 UTC

NP-MRD ID

NP0267039

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,3as,7as)-3-hexanoyl-6,7a-dimethyl-5-(2-oxopentyl)-3a,4-dihydro-3h-1-benzofuran-2,7-dione

Description

3Abeta,4-Dihydro-3beta-hexanoyl-6,7aalpha-dimethyl-5-(2-oxopentyl)benzofuran-2,7(3H,7aH)-dione belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Based on a literature review very few articles have been published on 3abeta,4-Dihydro-3beta-hexanoyl-6,7aalpha-dimethyl-5-(2-oxopentyl)benzofuran-2,7(3H,7aH)-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082213412D          

 26 27  0  0  1  0            999 V2000
    4.8525   -0.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5670   -1.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2815   -0.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9960   -1.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7104   -0.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4249   -1.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4249   -2.0886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1394   -0.8511    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2256   -0.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6125    0.5214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0326    0.1409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4451   -0.5736    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9300    0.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2521   -0.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8041   -0.1320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5070   -1.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3140   -1.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9550   -2.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2099   -2.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0169   -3.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2718   -3.8836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5689   -2.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3759   -2.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9279   -2.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1480   -1.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8930   -1.1867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  6  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 18 25  1  0  0  0  0
 26 25  1  1  0  0  0
  8 26  1  0  0  0  0
 12 26  1  0  0  0  0
M  END

     RDKit          3D

 56 57  0  0  0  0  0  0  0  0999 V2000
    5.7455    2.0270    0.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4374    1.2803   -0.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0755   -0.1866   -0.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5517   -0.2974   -0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1156   -1.7322   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6722   -1.9229   -0.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2299   -2.8565   -1.0086 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6656   -1.0300    0.2864 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8558   -1.2434    1.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8769   -1.0039    2.4553 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6669   -1.7711    2.2490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3295   -1.2503    1.4535 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4836    0.2150    1.6987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076   -1.9878    1.3918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8644   -2.9556    2.1022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5543   -1.4424    0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0025   -1.6174    0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0346   -0.8146   -0.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8347   -0.0626   -1.6324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1882    0.3527   -1.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1753   -0.2515   -1.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3948    1.6079   -0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8695    1.7686   -0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1621    3.0041    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5370   -0.6775   -0.8739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2531   -1.4834    0.0434 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3963    2.8568    0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7464    2.3330    0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6387    1.3269    1.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9251    1.6047   -1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5127    1.4521   -0.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3945   -0.5146    0.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5788   -0.8397   -1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2441    0.0313   -1.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1301    0.3787    0.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6264   -2.4083   -0.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4972   -2.0365    0.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7502    0.0051   -0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3611    0.7496    1.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185    0.6184    1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5708    0.3697    2.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0858   -2.3176    1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4912   -2.2385   -0.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5397   -0.7339    0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2812    0.8679   -1.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8381   -0.6761   -2.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0090    2.4304   -1.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8791    1.5127    0.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3810    1.9527   -1.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2742    0.8747    0.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4908    3.8433   -0.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9266    2.7092    1.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2460    3.2709    1.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3547   -0.9291   -1.9540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3064    0.3980   -0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1837   -2.5601   -0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8 26  1  0
 26 25  1  0
 25 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 18 16  2  0
 16 17  1  0
 16 14  1  0
 14 15  2  0
 14 12  1  0
 12 13  1  1
 12 11  1  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
 12 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  8 38  1  1
 26 56  1  6
 25 54  1  0
 25 55  1  0
 19 45  1  0
 19 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 13 39  1  0
 13 40  1  0
 13 41  1  0
M  END


  Mrv1652309082213412D          

 26 27  0  0  1  0            999 V2000
    4.8525   -0.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5670   -1.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2815   -0.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9960   -1.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7104   -0.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4249   -1.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4249   -2.0886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1394   -0.8511    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2256   -0.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6125    0.5214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0326    0.1409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4451   -0.5736    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9300    0.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2521   -0.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8041   -0.1320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5070   -1.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3140   -1.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9550   -2.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2099   -2.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0169   -3.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2718   -3.8836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5689   -2.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3759   -2.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9279   -2.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1480   -1.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8930   -1.1867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  6  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 18 25  1  0  0  0  0
 26 25  1  1  0  0  0
  8 26  1  0  0  0  0
 12 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0267039

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(=O)[C@H]1[C@@H]2CC(CC(=O)CCC)=C(C)C(=O)[C@@]2(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O5/c1-5-7-8-10-17(23)18-16-12-14(11-15(22)9-6-2)13(3)19(24)21(16,4)26-20(18)25/h16,18H,5-12H2,1-4H3/t16-,18+,21-/m0/s1

> <INCHI_KEY>
OAXAUYWDGCZYAX-CDXJDZJCSA-N

> <FORMULA>
C21H30O5

> <MOLECULAR_WEIGHT>
362.466

> <EXACT_MASS>
362.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
40.68417372388058

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aS,7aS)-3-hexanoyl-6,7a-dimethyl-5-(2-oxopentyl)-2,3,3a,4,7,7a-hexahydro-1-benzofuran-2,7-dione

> <JCHEM_LOGP>
4.5380035083333325

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.353386609204623

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.046775223863358

> <JCHEM_PKA_STRONGEST_BASIC>
-5.859408766836415

> <JCHEM_POLAR_SURFACE_AREA>
77.51

> <JCHEM_REFRACTIVITY>
98.7492

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aS,7aS)-3-hexanoyl-6,7a-dimethyl-5-(2-oxopentyl)-3a,4-dihydro-3H-1-benzofuran-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       9.058  -1.589   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.392  -2.359   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.725  -1.589   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.059  -2.359   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.393  -1.589   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.726  -2.359   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      15.726  -3.899   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      17.060  -1.589   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.221  -0.057   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      16.077   0.973   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      18.727   0.263   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      19.497  -1.071   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.403   0.175   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.004  -1.391   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      22.034  -0.246   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      21.480  -2.856   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.986  -3.176   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.449  -4.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.925  -5.465   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.431  -5.785   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      22.907  -7.249   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      23.462  -4.640   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      24.968  -4.961   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.999  -3.816   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.943  -3.680   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.467  -2.215   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   26                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14   26                                             
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   18   26                                                       
CONECT   26   25    8   12                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
3Abeta,4-dihydro-3b-hexanoyl-6,7aalpha-dimethyl-5-(2-oxopentyl)benzofuran-2,7(3H,7ah)-dione	Generator
3Abeta,4-dihydro-3β-hexanoyl-6,7aalpha-dimethyl-5-(2-oxopentyl)benzofuran-2,7(3H,7ah)-dione	Generator

Chemical Formula

C₂₁H₃₀O₅

Average Mass

362.4660 Da

Monoisotopic Mass

362.20932 Da

IUPAC Name

(3R,3aS,7aS)-3-hexanoyl-6,7a-dimethyl-5-(2-oxopentyl)-2,3,3a,4,7,7a-hexahydro-1-benzofuran-2,7-dione

Traditional Name

(3R,3aS,7aS)-3-hexanoyl-6,7a-dimethyl-5-(2-oxopentyl)-3a,4-dihydro-3H-1-benzofuran-2,7-dione

CAS Registry Number

Not Available

SMILES

CCCCCC(=O)[C@H]1[C@@H]2CC(CC(=O)CCC)=C(C)C(=O)[C@@]2(C)OC1=O

InChI Identifier

InChI=1S/C21H30O5/c1-5-7-8-10-17(23)18-16-12-14(11-15(22)9-6-2)13(3)19(24)21(16,4)26-20(18)25/h16,18H,5-12H2,1-4H3/t16-,18+,21-/m0/s1

InChI Key

OAXAUYWDGCZYAX-CDXJDZJCSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Benzofuran
Cyclohexenone
Alpha-acyloxy ketone
Gamma butyrolactone
1,3-dicarbonyl compound
Oxolane
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen 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	4.54	ChemAxon
pKa (Strongest Acidic)	10.05	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	77.51 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	98.75 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

101534718

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,3as,7as)-3-hexanoyl-6,7a-dimethyl-5-(2-oxopentyl)-3a,4-dihydro-3h-1-benzofuran-2,7-dione (NP0267039)

MOL for NP0267039 ((3r,3as,7as)-3-hexanoyl-6,7a-dimethyl-5-(2-oxopentyl)-3a,4-dihydro-3h-1-benzofuran-2,7-dione)

3D MOL for NP0267039 ((3r,3as,7as)-3-hexanoyl-6,7a-dimethyl-5-(2-oxopentyl)-3a,4-dihydro-3h-1-benzofuran-2,7-dione)

3D SDF for NP0267039 ((3r,3as,7as)-3-hexanoyl-6,7a-dimethyl-5-(2-oxopentyl)-3a,4-dihydro-3h-1-benzofuran-2,7-dione)

3D-SDF for NP0267039 ((3r,3as,7as)-3-hexanoyl-6,7a-dimethyl-5-(2-oxopentyl)-3a,4-dihydro-3h-1-benzofuran-2,7-dione)

PDB for NP0267039 ((3r,3as,7as)-3-hexanoyl-6,7a-dimethyl-5-(2-oxopentyl)-3a,4-dihydro-3h-1-benzofuran-2,7-dione)

3D PDB for NP0267039 ((3r,3as,7as)-3-hexanoyl-6,7a-dimethyl-5-(2-oxopentyl)-3a,4-dihydro-3h-1-benzofuran-2,7-dione)

SMILES for NP0267039 ((3r,3as,7as)-3-hexanoyl-6,7a-dimethyl-5-(2-oxopentyl)-3a,4-dihydro-3h-1-benzofuran-2,7-dione)

INCHI for NP0267039 ((3r,3as,7as)-3-hexanoyl-6,7a-dimethyl-5-(2-oxopentyl)-3a,4-dihydro-3h-1-benzofuran-2,7-dione)

Structure for NP0267039 ((3r,3as,7as)-3-hexanoyl-6,7a-dimethyl-5-(2-oxopentyl)-3a,4-dihydro-3h-1-benzofuran-2,7-dione)

3D Structure for NP0267039 ((3r,3as,7as)-3-hexanoyl-6,7a-dimethyl-5-(2-oxopentyl)-3a,4-dihydro-3h-1-benzofuran-2,7-dione)