NP-MRD: Showing NP-Card for (1r,4r,5r,7s,8r,9r,10r,11s,12s)-5-(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-7-yl (2e)-2-methylbut-2-enoate (NP0304394)

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Record Information

Version

1.0

Created at

2022-09-10 19:27:06 UTC

Updated at

2022-09-10 19:27:07 UTC

NP-MRD ID

NP0304394

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4r,5r,7s,8r,9r,10r,11s,12s)-5-(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-7-yl (2e)-2-methylbut-2-enoate

Description

(1R,4R,5R,7S,8R,9R,10R,11S,12S)-5-(acetyloxy)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0⁴,¹²]Dodecan-7-yl (2E)-2-methylbut-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. (1r,4r,5r,7s,8r,9r,10r,11s,12s)-5-(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-7-yl (2e)-2-methylbut-2-enoate is found in Melia azedarach. It was first documented in 1993 (PMID: 36137062). Based on a literature review a significant number of articles have been published on (1R,4R,5R,7S,8R,9R,10R,11S,12S)-5-(acetyloxy)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0⁴,¹²]Dodecan-7-yl (2E)-2-methylbut-2-enoate (PMID: 36137063) (PMID: 36137748) (PMID: 36137747) (PMID: 36137746).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102221272D          

 52 56  0  0  1  0            999 V2000
   -0.2472   -4.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1610   -3.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5927   -3.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2602   -3.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6790   -2.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115   -1.8328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326   -1.9821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -1.1617    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8514   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    0.1437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2702    0.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4835    0.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5697   -0.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1509    0.7780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0782    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0285    1.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8661   -0.6767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2278   -1.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6592   -0.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3093   -0.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2805   -1.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9932   -0.4959    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7685   -0.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4524   -0.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1025   -0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2954    0.2108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3019   -1.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.0056    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  1  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 33 37  2  0  0  0  0
 32 38  1  0  0  0  0
 38 39  1  0  0  0  0
 29 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 27 44  1  0  0  0  0
 44 45  1  6  0  0  0
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 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 44 50  1  0  0  0  0
  8 50  1  0  0  0  0
 50 51  1  6  0  0  0
 50 52  1  0  0  0  0
 52 19  1  1  0  0  0
 15 52  1  0  0  0  0
M  END

     RDKit          3D

106110  0  0  0  0  0  0  0  0999 V2000
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   -5.7441   -3.5612    0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7689    2.7203   -0.7649 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5690    3.7808   -1.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5574    3.5101   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4241    3.2595   -1.1444 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2444    1.9859   -1.6661 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.4887   -4.0360   -4.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
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 49101  1  0
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 51103  1  0
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  1 54  1  0
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 31 84  1  0
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 39 93  1  6
 42 94  1  0
 42 95  1  0
 42 96  1  0
 37 90  1  0
 35 89  1  0
 34 88  1  0
M  END


  Mrv1652309102221272D          

 52 56  0  0  1  0            999 V2000
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   -0.1610   -3.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2602   -3.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6790   -2.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115   -1.8328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326   -1.9821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -1.1617    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.9377    0.1437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2702    0.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4835    0.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6913    0.4793    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0782    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9463    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713    1.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.4793    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7799    0.1437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4473    0.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3611    1.4492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6074    1.7847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0285    1.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9423    2.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7822    1.5985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -0.6767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2278   -1.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6592   -0.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3093   -0.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2805   -1.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9932   -0.4959    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7685   -0.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4524   -0.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1025   -0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8204   -1.5999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9959   -1.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7658    0.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9413    0.3259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4800    1.0099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6570    0.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1957    1.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2954    0.2108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -1.1617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3141   -1.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0793   -2.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7290   -1.7786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1947   -3.1039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9598   -3.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.8261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3019   -1.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.0056    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  1  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 33 37  2  0  0  0  0
 32 38  1  0  0  0  0
 38 39  1  0  0  0  0
 29 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 27 44  1  0  0  0  0
 44 45  1  6  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 44 50  1  0  0  0  0
  8 50  1  0  0  0  0
 50 51  1  6  0  0  0
 50 52  1  0  0  0  0
 52 19  1  1  0  0  0
 15 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0304394

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@@H]1[C@]2(C)[C@@H]3[C@@H](OC[C@]3(C)[C@@H](C[C@@H]2OC(=O)C(\C)=C\C)OC(C)=O)[C@@H](OC(=O)C(C)C)[C@@]1(C)C1=C(C)[C@@H](C[C@@H]1OC(C)=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C40H54O12/c1-12-21(4)37(45)51-30-17-29(50-24(7)42)38(8)19-48-33-34(38)39(30,9)28(16-31(43)46-11)40(10,35(33)52-36(44)20(2)3)32-22(5)26(25-13-14-47-18-25)15-27(32)49-23(6)41/h12-14,18,20,26-30,33-35H,15-17,19H2,1-11H3/b21-12+/t26-,27+,28-,29-,30+,33-,34-,35-,38-,39+,40-/m1/s1

> <INCHI_KEY>
SZFHJFQBAFXSCJ-CJTLRBPZSA-N

> <FORMULA>
C40H54O12

> <MOLECULAR_WEIGHT>
726.86

> <EXACT_MASS>
726.361527179

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
106

> <JCHEM_AVERAGE_POLARIZABILITY>
75.83147658113764

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4R,5R,7S,8R,9R,10R,11S,12S)-5-(acetyloxy)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-7-yl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
4.921910638999997

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.857102835300345

> <JCHEM_POLAR_SURFACE_AREA>
153.86999999999998

> <JCHEM_REFRACTIVITY>
187.1012

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R,5R,7S,8R,9R,10R,11S,12S)-5-(acetyloxy)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-7-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.461  -8.016   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.300  -6.484   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.106  -5.858   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.352  -6.763   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.267  -4.326   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.021  -3.421   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.674  -3.700   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.835  -2.168   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.589  -1.263   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.750   0.268   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.504   1.174   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.902   0.547   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.063  -0.984   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.148   1.452   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.157   0.895   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.013   1.925   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.633   2.359   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.173   2.359   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.649   0.895   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.056   0.268   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.302   1.174   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.141   2.705   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.734   3.331   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.387   3.610   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.226   5.142   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.793   2.984   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.217  -1.263   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.892  -2.647   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.697  -0.839   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.911  -1.787   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.857  -3.326   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.187  -0.926   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.634  -1.452   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.911  -0.591   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.125  -1.539   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      14.598  -2.987   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      13.059  -2.933   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.763   0.555   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.224   0.608   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       8.363   1.885   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       6.826   1.778   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.965   3.054   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       6.151   0.394   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       5.971  -2.168   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.186  -3.693   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       7.615  -4.269   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       8.827  -3.320   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       7.830  -5.794   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       9.258  -6.370   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       4.242  -1.542   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       4.297  -3.081   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       4.403  -0.010   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   50                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16   17   52                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   52                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   20   28   29   44                                             
CONECT   28   27                                                            
CONECT   29   27   30   39                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   38                                                  
CONECT   33   32   34   37                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   33                                                       
CONECT   38   32   39                                                       
CONECT   39   38   29   40                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   27   45   50                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48                                                            
CONECT   50   44    8   51   52                                             
CONECT   51   50                                                            
CONECT   52   50   19   15                                                  
MASTER        0    0    0    0    0    0    0    0   52    0  112    0
END

View in JSmol

Synonyms

Value	Source
(1R,4R,5R,7S,8R,9R,10R,11S,12S)-5-(Acetyloxy)-10-[(3R,5S)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0,]dodecan-7-yl (2E)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₄₀H₅₄O₁₂

Average Mass

726.8600 Da

Monoisotopic Mass

726.36153 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@@H]1[C@]2(C)[C@@H]3[C@@H](OC[C@]3(C)[C@@H](C[C@@H]2OC(=O)C(\C)=C\C)OC(C)=O)[C@@H](OC(=O)C(C)C)[C@@]1(C)C1=C(C)[C@@H](C[C@@H]1OC(C)=O)C1=COC=C1

InChI Identifier

InChI=1S/C40H54O12/c1-12-21(4)37(45)51-30-17-29(50-24(7)42)38(8)19-48-33-34(38)39(30,9)28(16-31(43)46-11)40(10,35(33)52-36(44)20(2)3)32-22(5)26(25-13-14-47-18-25)15-27(32)49-23(6)41/h12-14,18,20,26-30,33-35H,15-17,19H2,1-11H3/b21-12+/t26-,27+,28-,29-,30+,33-,34-,35-,38-,39+,40-/m1/s1

InChI Key

SZFHJFQBAFXSCJ-CJTLRBPZSA-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
Melia azedarach	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
Pentacarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Furan
Tetrahydrofuran
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Organoheterocyclic compound
Ether
Oxacycle
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen 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	4.92	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	153.87 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	187.1 m³·mol⁻¹	ChemAxon
Polarizability	75.83 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

163188427

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Salisbury L, Baraitser L: Depressing time: Waiting, melancholia, and the psychoanalytic practice of care. 2020. [PubMed:36137063 ]
Heimer G, Neuser S, Ben-Zeev B, Ebrahimi-Fakhari D: TECPR2-Related Hereditary Sensory and Autonomic Neuropathy with Intellectual Disability. 1993. [PubMed:36137062 ]
Tibbe D, Ferle P, Krisp C, Nampoothiri S, Mirzaa G, Assaf M, Parikh S, Kutsche K, Kreienkamp HJ: Regulation of Liprin-alpha phase separation by CASK is disrupted by a mutation in its CaM kinase domain. Life Sci Alliance. 2022 Sep 22;5(10). pii: 5/10/e202201512. doi: 10.26508/lsa.202201512. Print 2022 Oct. [PubMed:36137748 ]
Sengupta R, Mihelc EM, Angel S, Lanman JK, Kuhn RJ, Stahelin RV: Contribution of the Golgi apparatus in morphogenesis of a virus-induced cytopathic vacuolar system. Life Sci Alliance. 2022 Sep 22;5(10). pii: 5/10/e202000887. doi: 10.26508/lsa.202000887. Print 2022 Oct. [PubMed:36137747 ]
Cui Y, Peng S, Czaplicki L, Yang T: Protecting minors from tobacco products: public interest litigation enables enforcement in China. Tob Control. 2022 Sep 22. pii: tc-2022-057615. doi: 10.1136/tc-2022-057615. [PubMed:36137746 ]
LOTUS database [Link]

Showing NP-Card for (1r,4r,5r,7s,8r,9r,10r,11s,12s)-5-(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-7-yl (2e)-2-methylbut-2-enoate (NP0304394)

MOL for NP0304394 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5-(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-7-yl (2e)-2-methylbut-2-enoate)

3D MOL for NP0304394 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5-(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-7-yl (2e)-2-methylbut-2-enoate)

3D SDF for NP0304394 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5-(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-7-yl (2e)-2-methylbut-2-enoate)

3D-SDF for NP0304394 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5-(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-7-yl (2e)-2-methylbut-2-enoate)

PDB for NP0304394 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5-(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-7-yl (2e)-2-methylbut-2-enoate)

3D PDB for NP0304394 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5-(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-7-yl (2e)-2-methylbut-2-enoate)

SMILES for NP0304394 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5-(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-7-yl (2e)-2-methylbut-2-enoate)

INCHI for NP0304394 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5-(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-7-yl (2e)-2-methylbut-2-enoate)

Structure for NP0304394 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5-(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-7-yl (2e)-2-methylbut-2-enoate)

3D Structure for NP0304394 ((1r,4r,5r,7s,8r,9r,10r,11s,12s)-5-(acetyloxy)-10-[(3r,5s)-5-(acetyloxy)-3-(furan-3-yl)-2-methylcyclopent-1-en-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-11-[(2-methylpropanoyl)oxy]-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-7-yl (2e)-2-methylbut-2-enoate)