NP-MRD: Showing NP-Card for 16-[1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate (NP0269788)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-08 15:23:29 UTC

Updated at

2022-09-08 15:23:29 UTC

NP-MRD ID

NP0269788

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-[1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate

Description

16-[1-(Acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. 16-[1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate is found in Swietenia mahagoni. 16-[1-(Acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261513172D          

 45 49  0  0  0  0            999 V2000
   -2.3256    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5449    1.5306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9235    0.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0829    0.1783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1428    1.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0166    2.0639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047    2.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854    2.3400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4453    3.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4785    0.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2148   -0.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4045   -0.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4721    0.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5811   -0.8093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0383   -1.4306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3050   -2.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2378   -2.8326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1144   -2.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3811   -3.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1906   -3.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8383   -3.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6572   -1.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3628   -1.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1020   -0.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3657    0.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1891    0.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5554   -0.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3787   -0.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7450   -1.5081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8357   -0.0821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4694    0.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9265    1.3440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6394    2.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2863    2.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9732    2.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7508    1.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6461    0.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1031    1.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2798    1.4487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4564    1.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9994    0.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2177    1.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1622    1.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0214   -0.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3228    0.4233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 32 36  1  0  0  0  0
 31 37  1  0  0  0  0
 26 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 25 41  1  0  0  0  0
 41 42  1  0  0  0  0
 10 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 23 44  1  0  0  0  0
 44 45  2  0  0  0  0
M  END

     RDKit          3D

 89 93  0  0  0  0  0  0  0  0999 V2000
   -0.5127   -3.2234   -4.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4655   -3.3349   -2.7894 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4126   -2.4870   -2.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542   -1.7205   -2.7345 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3667   -2.7058   -0.5829 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7042   -3.5132   -0.2505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7223   -4.8517    0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0185   -5.4929    0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3525   -5.4694   -0.0132 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8822   -1.7194    0.3618 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3654   -1.4916    0.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9506   -2.5400    1.4043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1448   -1.7796   -0.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6876   -0.0924    0.9411 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1412    0.7932   -0.0243 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3694    1.2834   -0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2192    0.8658    0.5753 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6832    2.2012   -1.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1065    2.7046   -1.4620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8312    2.6636   -2.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2870    3.6223   -3.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3894    2.2608   -2.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069    0.3874    2.0166 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8156    1.4220    1.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5851    0.9075    1.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5591    1.7868    1.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2095    3.2201    1.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6120    3.6831   -0.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8660    4.3240   -0.8755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9100    3.3509   -0.4609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5338    2.1264   -0.1306 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0196    2.2645   -0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9415    1.3802   -0.6812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1840    1.8793   -0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0373    2.9967    0.2158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7816    3.2674    0.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9914    1.4849    1.1259 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7139    2.0179    2.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2821    0.0163    1.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0626   -0.7986    0.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9739   -0.5067    1.6200 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1768   -1.5010    1.6590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3597   -2.7026    2.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0954   -0.7853    2.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1950   -1.1937    3.7263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4518   -2.7570   -4.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3879   -2.7190   -4.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5047   -4.2591   -4.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2559   -3.5550   -0.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1844   -5.4001    1.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8558   -4.9290   -0.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0451   -6.5461    0.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -0.7081   -0.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9353   -2.8524    0.9355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434   -2.1172    2.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3433   -3.4290    1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2547   -2.0080   -0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9284   -2.7315   -1.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1851   -0.9994   -1.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6726   -0.2953    1.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6360    2.4830   -0.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5319    2.2416   -2.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0608    3.8162   -1.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3270    3.3797   -3.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5704    3.5895   -4.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3011    4.6579   -2.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2522    1.2268   -2.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9274    2.3735   -1.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8416    2.9086   -2.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4238    0.7537    2.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7786    2.1503    2.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9901    2.0909    0.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9435    3.7387    1.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2431    3.5309    1.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3045    1.4481   -1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7504    0.4649   -1.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1329    1.4375   -0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4424    4.1309    0.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1625    1.7380    3.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8254    3.0987    2.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7271    1.5439    2.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0930   -0.2043    0.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6024   -0.4006    2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4447   -1.8482    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8486   -0.5511   -0.3745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583   -0.5986    2.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2620   -3.5806    2.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5080   -2.3837    3.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -2.9303    2.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  2  3
 20 21  1  0
 20 22  1  0
 14 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 36  2  0
 36 35  1  0
 35 34  1  0
 34 33  2  0
 31 37  1  0
 37 38  1  1
 37 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  1
 42 44  1  0
 44 45  2  0
 42 10  1  0
 44 23  1  0
 41 25  1  0
 37 26  1  0
 33 32  1  0
  1 46  1  0
  1 47  1  0
  1 48  1  0
  5 49  1  6
  8 50  1  0
  8 51  1  0
  8 52  1  0
 10 53  1  6
 12 54  1  0
 12 55  1  0
 12 56  1  0
 13 57  1  0
 13 58  1  0
 13 59  1  0
 14 60  1  1
 19 61  1  0
 19 62  1  0
 19 63  1  0
 21 64  1  0
 21 65  1  0
 21 66  1  0
 22 67  1  0
 22 68  1  0
 22 69  1  0
 23 70  1  1
 24 71  1  0
 24 72  1  0
 27 73  1  0
 27 74  1  0
 31 75  1  6
 36 78  1  0
 34 77  1  0
 33 76  1  0
 38 79  1  0
 38 80  1  0
 38 81  1  0
 39 82  1  0
 39 83  1  0
 40 84  1  0
 40 85  1  0
 41 86  1  1
 43 87  1  0
 43 88  1  0
 43 89  1  0
M  END


  Mrv1533004261513172D          

 45 49  0  0  0  0            999 V2000
   -2.3256    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5449    1.5306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9235    0.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0829    0.1783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1428    1.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0166    2.0639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047    2.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854    2.3400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4453    3.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4785    0.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2148   -0.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4045   -0.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4721    0.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5811   -0.8093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0383   -1.4306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3050   -2.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2378   -2.8326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1144   -2.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3811   -3.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1906   -3.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8383   -3.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6572   -1.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3628   -1.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1020   -0.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3657    0.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1891    0.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5554   -0.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3787   -0.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7450   -1.5081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8357   -0.0821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4694    0.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9265    1.3440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6394    2.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2863    2.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9732    2.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7508    1.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6461    0.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1031    1.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2798    1.4487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4564    1.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9994    0.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2177    1.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1622    1.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0214   -0.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3228    0.4233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 32 36  1  0  0  0  0
 31 37  1  0  0  0  0
 26 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 25 41  1  0  0  0  0
 41 42  1  0  0  0  0
 10 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 23 44  1  0  0  0  0
 44 45  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0269788

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(OC(C)=O)C1C(C)(C)C(OC(=O)C(C)=C(C)C)C2CC3=C4CC(=O)OC(C5=COC=C5)C4(C)CCC3C1(C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H44O10/c1-17(2)18(3)31(39)45-30-22-14-21-23(10-12-34(7)24(21)15-25(37)44-29(34)20-11-13-42-16-20)35(8,28(22)38)27(33(30,5)6)26(32(40)41-9)43-19(4)36/h11,13,16,22-23,26-27,29-30H,10,12,14-15H2,1-9H3

> <INCHI_KEY>
AYEZTOKCHWMCDA-UHFFFAOYSA-N

> <FORMULA>
C35H44O10

> <MOLECULAR_WEIGHT>
624.727

> <EXACT_MASS>
624.293447617

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
65.72781614178514

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-[1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate

> <ALOGPS_LOGP>
3.97

> <JCHEM_LOGP>
5.141548475666665

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.567452261022474

> <JCHEM_PKA_STRONGEST_BASIC>
-2.88881026843076

> <JCHEM_POLAR_SURFACE_AREA>
135.41

> <JCHEM_REFRACTIVITY>
161.3418

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-[1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -4.341   2.359   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.884   2.857   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.724   1.844   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.022   0.333   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.267   2.342   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.031   3.853   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.129   4.866   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.586   4.368   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.831   6.377   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.893   1.328   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.401  -0.131   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.755  -1.148   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.881   0.722   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.085  -1.511   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.071  -2.670   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.569  -4.128   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.444  -5.287   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.080  -4.425   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.578  -5.883   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.089  -6.180   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.565  -7.042   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.093  -3.265   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.544  -2.003   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.924  -1.319   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.416   0.140   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.953   0.042   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.637  -1.338   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.174  -1.435   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.857  -2.815   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       9.027  -0.153   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.343   1.227   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.196   2.509   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.660   3.953   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.868   4.908   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      11.150   4.055   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.735   2.572   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.806   1.324   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.659   2.607   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.122   2.704   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.585   2.802   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.732   1.520   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.273   2.012   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.169   3.549   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.907  -0.029   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       0.603   0.790   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   42                                                  
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18                                                            
CONECT   23   14   24   44                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   41                                                  
CONECT   26   25   27   37                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33   36                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   32                                                       
CONECT   37   31   26   38   39                                             
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   25   42                                                  
CONECT   42   41   10   43   44                                             
CONECT   43   42                                                            
CONECT   44   42   23   45                                                  
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   98    0
END

View in JSmol

Synonyms

Value	Source
16-[1-(Acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0,.0,]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoic acid	Generator
16-[1-(Acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoic acid	Generator

Chemical Formula

C₃₅H₄₄O₁₀

Average Mass

624.7270 Da

Monoisotopic Mass

624.29345 Da

IUPAC Name

16-[1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate

Traditional Name

16-[1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(OC(C)=O)C1C(C)(C)C(OC(=O)C(C)=C(C)C)C2CC3=C4CC(=O)OC(C5=COC=C5)C4(C)CCC3C1(C)C2=O

InChI Identifier

InChI=1S/C35H44O10/c1-17(2)18(3)31(39)45-30-22-14-21-23(10-12-34(7)24(21)15-25(37)44-29(34)20-11-13-42-16-20)35(8,28(22)38)27(33(30,5)6)26(32(40)41-9)43-19(4)36/h11,13,16,22-23,26-27,29-30H,10,12,14-15H2,1-9H3

InChI Key

AYEZTOKCHWMCDA-UHFFFAOYSA-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

Species Name	Source	Reference
Swietenia mahagoni	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Mexicanolide
Naphthopyran
Tetracarboxylic acid or derivatives
Naphthalene
Delta valerolactone
Fatty acid ester
Delta_valerolactone
Fatty acyl
Oxane
Pyran
Heteroaromatic compound
Furan
Alpha,beta-unsaturated carboxylic ester
Methyl ester
Enoate ester
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.97	ALOGPS
logP	5.14	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	18.57	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	135.41 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	161.34 m³·mol⁻¹	ChemAxon
Polarizability	65.73 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-[1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate (NP0269788)

MOL for NP0269788 (16-[1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate)

3D MOL for NP0269788 (16-[1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate)

3D SDF for NP0269788 (16-[1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate)

3D-SDF for NP0269788 (16-[1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate)

PDB for NP0269788 (16-[1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate)

3D PDB for NP0269788 (16-[1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate)

SMILES for NP0269788 (16-[1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate)

INCHI for NP0269788 (16-[1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate)

Structure for NP0269788 (16-[1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate)

3D Structure for NP0269788 (16-[1-(acetyloxy)-2-methoxy-2-oxoethyl]-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-10-en-14-yl 2,3-dimethylbut-2-enoate)