NP-MRD: Showing NP-Card for (4r,5r,14s,16r,18r,19s,20r,22s)-15-(acetyloxy)-5-(furan-3-yl)-16-hydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-12-(sec-butyl)-6,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]docos-8-en-22-yl (2e)-2-methylbut-2-enoate (NP0151715)

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Record Information

Version

2.0

Created at

2022-09-02 08:04:10 UTC

Updated at

2022-09-02 08:04:10 UTC

NP-MRD ID

NP0151715

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r,5r,14s,16r,18r,19s,20r,22s)-15-(acetyloxy)-5-(furan-3-yl)-16-hydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-12-(sec-butyl)-6,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]docos-8-en-22-yl (2e)-2-methylbut-2-enoate

Description

Swietephragmin B 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. (4r,5r,14s,16r,18r,19s,20r,22s)-15-(acetyloxy)-5-(furan-3-yl)-16-hydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-12-(sec-butyl)-6,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]docos-8-en-22-yl (2e)-2-methylbut-2-enoate is found in Swietenia mahagoni. (4r,5r,14s,16r,18r,19s,20r,22s)-15-(acetyloxy)-5-(furan-3-yl)-16-hydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-12-(sec-butyl)-6,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]docos-8-en-22-yl (2e)-2-methylbut-2-enoate was first documented in 2013 (PMID: 24034555). Based on a literature review very few articles have been published on Swietephragmin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022210042D          

 52 59  0  0  1  0            999 V2000
   -1.5845    2.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1674    1.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3424    1.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0655    2.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0746    0.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3334    0.0909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8996    0.8133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3166    0.1014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1604   -0.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1369    0.7928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8394    1.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8159    2.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6571    1.3350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5790    0.8145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2296    0.2869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2481   -1.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4844   -2.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8057   -3.1893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1499   -2.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  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  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
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  9 14  1  0  0  0  0
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 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
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 19 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
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 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 33  2  0  0  0  0
 28 34  1  0  0  0  0
 23 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 22 38  1  0  0  0  0
 38 39  1  0  0  0  0
 16 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
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 46 47  1  0  0  0  0
 42 48  1  0  0  0  0
  8 48  1  0  0  0  0
 48 49  1  6  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
  9 51  1  0  0  0  0
 40 51  1  0  0  0  0
 51 52  1  1  0  0  0
M  END

     RDKit          3D

100107  0  0  0  0  0  0  0  0999 V2000
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   -2.4946   -1.0774    3.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4554    0.1024   -2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9041   -1.7045   -2.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5633   -0.5539   -1.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5163   -2.2167    0.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5695   -3.1538   -0.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9310   -3.4101    1.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 17  1  0
 17 18  1  0
 17 16  1  0
 16 15  1  1
 15 14  1  0
 14  9  1  0
  9 10  1  1
 10 11  1  0
 11 12  1  0
 11 13  2  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  2  1  1  0
  8 48  1  0
 48 49  1  6
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 51 52  1  1
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 40 22  1  0
 22 23  1  0
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 31 29  1  0
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 35 34  2  0
 22 21  1  1
 39 16  1  0
 34 33  1  0
 21 16  1  0
 38 14  1  0
 51  9  1  0
 38 22  1  0
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 27 25  1  0
 20 71  1  0
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 17 65  1  1
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 12 61  1  0
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  8 60  1  1
  4 57  1  0
  4 58  1  0
  4 59  1  0
  2 56  1  0
  1 53  1  0
  1 54  1  0
  1 55  1  0
 49 95  1  0
 49 96  1  0
 49 97  1  0
 50 98  1  0
 50 99  1  0
 52100  1  0
 41 86  1  0
 41 87  1  0
 41 88  1  0
 42 89  1  6
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 43 91  1  0
 47 92  1  0
 47 93  1  0
 47 94  1  0
 23 74  1  0
 23 75  1  0
 24 76  1  0
 24 77  1  0
 26 78  1  0
 26 79  1  0
 26 80  1  0
 32 82  1  6
 28 81  1  0
 37 85  1  0
 35 84  1  0
 34 83  1  0
M  END


  Mrv1652309022210042D          

 52 59  0  0  1  0            999 V2000
   -1.5845    2.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1674    1.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3424    1.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0655    2.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0746    0.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3334    0.0909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8996    0.8133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3166    0.1014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1604   -0.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1369    0.7928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8394    1.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8159    2.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6571    1.3350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0425    0.1595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5790    0.8145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2296    0.2869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9812    0.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8062    0.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0626    1.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8143    1.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5294   -0.1522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6345   -0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6630   -0.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0163    0.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8386    0.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1919    0.9381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3076   -0.4861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9543   -1.2317    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4233   -1.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2481   -1.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4844   -2.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8057   -3.1893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1499   -2.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1320   -1.2985    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5403   -2.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6657   -1.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8228   -1.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3931   -1.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1843   -0.8512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4441   -1.4271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6529   -2.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5549   -1.6716    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2405   -2.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4227   -2.5434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0806   -1.8897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1083   -3.3061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7094   -3.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0116   -0.7235    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1894   -0.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1389   -1.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0126   -0.8160    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8187   -0.6406    0.0000 O   0  0  0  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  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 33  2  0  0  0  0
 28 34  1  0  0  0  0
 23 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 22 38  1  0  0  0  0
 38 39  1  0  0  0  0
 16 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 42 48  1  0  0  0  0
  8 48  1  0  0  0  0
 48 49  1  6  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
  9 51  1  0  0  0  0
 40 51  1  0  0  0  0
 51 52  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0151715

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C12O[C@@H]3C4(OC(C)=O)[C@@H](OC(=O)C(\C)=C\C)[C@]5(C)C[C@@]4(O)[C@@](C)([C@H]5CC(=O)OC)C4(CC[C@@]5(C)[C@@H](OC(=O)C=C5C34O1)C1=COC=C1)O2

> <INCHI_IDENTIFIER>
InChI=1S/C39H48O13/c1-10-20(3)29(43)48-30-33(7)19-35(44)34(8,24(33)16-26(41)45-9)36-14-13-32(6)25(17-27(42)47-28(32)23-12-15-46-18-23)37(36)31(38(30,35)49-22(5)40)50-39(51-36,52-37)21(4)11-2/h10,12,15,17-18,21,24,28,30-31,44H,11,13-14,16,19H2,1-9H3/b20-10+/t21?,24-,28-,30-,31-,32+,33+,34+,35+,36?,37?,38?,39?/m0/s1

> <INCHI_KEY>
HOKJOPUNHSFUMB-QVNUJKFWSA-N

> <FORMULA>
C39H48O13

> <MOLECULAR_WEIGHT>
724.8

> <EXACT_MASS>
724.309491606

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
73.869983131172

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,5R,14S,16R,18R,19S,20R,22S)-15-(acetyloxy)-12-(butan-2-yl)-5-(furan-3-yl)-16-hydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaheptacyclo[10.8.1.1^{15,18}.0^{1,10}.0^{4,9}.0^{10,14}.0^{16,20}]docos-8-en-22-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
4.10

> <JCHEM_LOGP>
5.241664541333333

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.043166309685116

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8627515375063686

> <JCHEM_POLAR_SURFACE_AREA>
166.26

> <JCHEM_REFRACTIVITY>
179.16840000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,5R,14S,16R,18R,19S,20R,22S)-15-(acetyloxy)-5-(furan-3-yl)-16-hydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-12-(sec-butyl)-6,11,13,21-tetraoxaheptacyclo[10.8.1.1^{15,18}.0^{1,10}.0^{4,9}.0^{10,14}.0^{16,20}]docos-8-en-22-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.958   4.156   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.179   2.827   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.639   2.837   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.122   4.176   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.139   1.508   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.622   0.170   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.679   1.518   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.458   0.189   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.033  -0.060   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.989   1.480   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.300   2.287   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.256   3.827   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.827   2.492   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.679   0.298   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.681   1.520   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.895   0.536   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.298   1.170   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.838   1.179   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.450   2.703   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.853   3.338   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.455  -0.284   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.784  -0.895   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.704  -1.157   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.364   0.235   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.899   0.359   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.558   1.751   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      11.774  -0.907   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      11.115  -2.299   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.990  -3.566   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.530  -3.602   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.971  -5.078   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      12.704  -5.953   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      11.480  -5.019   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.580  -2.424   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.342  -3.762   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.709  -3.652   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.136  -3.634   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.334  -2.224   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       7.811  -1.589   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       4.562  -2.664   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.952  -4.154   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.903  -3.120   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.316  -4.544   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       0.789  -4.748   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -0.150  -3.528   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       0.202  -6.171   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -1.324  -6.375   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       1.888  -1.351   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       0.354  -1.478   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       2.126  -2.417   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       3.757  -1.523   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       5.262  -1.196   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   48                                                  
CONECT    9    8   10   14   51                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21   39                                             
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   16   22                                                       
CONECT   22   21   14   23   38                                             
CONECT   23   22   24   34                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   34                                                  
CONECT   29   28   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   29                                                       
CONECT   34   28   23   35   36                                             
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   22   39   40                                             
CONECT   39   38   16                                                       
CONECT   40   38   41   42   51                                             
CONECT   41   40                                                            
CONECT   42   40   43   48                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46                                                            
CONECT   48   42    8   49   50                                             
CONECT   49   48                                                            
CONECT   50   48   51                                                       
CONECT   51   50    9   40   52                                             
CONECT   52   51                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  118    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₉H₄₈O₁₃

Average Mass

724.8000 Da

Monoisotopic Mass

724.30949 Da

IUPAC Name

(4R,5R,14S,16R,18R,19S,20R,22S)-15-(acetyloxy)-12-(butan-2-yl)-5-(furan-3-yl)-16-hydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaheptacyclo[10.8.1.1^{15,18}.0^{1,10}.0^{4,9}.0^{10,14}.0^{16,20}]docos-8-en-22-yl (2E)-2-methylbut-2-enoate

Traditional Name

(4R,5R,14S,16R,18R,19S,20R,22S)-15-(acetyloxy)-5-(furan-3-yl)-16-hydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-12-(sec-butyl)-6,11,13,21-tetraoxaheptacyclo[10.8.1.1^{15,18}.0^{1,10}.0^{4,9}.0^{10,14}.0^{16,20}]docos-8-en-22-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CCC(C)C12O[C@@H]3C4(OC(C)=O)[C@@H](OC(=O)C(\C)=C\C)[C@]5(C)C[C@@]4(O)[C@@](C)([C@H]5CC(=O)OC)C4(CC[C@@]5(C)[C@@H](OC(=O)C=C5C34O1)C1=COC=C1)O2

InChI Identifier

InChI=1S/C39H48O13/c1-10-20(3)29(43)48-30-33(7)19-35(44)34(8,24(33)16-26(41)45-9)36-14-13-32(6)25(17-27(42)47-28(32)23-12-15-46-18-23)37(36)31(38(30,35)49-22(5)40)50-39(51-36,52-37)21(4)11-2/h10,12,15,17-18,21,24,28,30-31,44H,11,13-14,16,19H2,1-9H3/b20-10+/t21?,24-,28-,30-,31-,32+,33+,34+,35+,36?,37?,38?,39?/m0/s1

InChI Key

HOKJOPUNHSFUMB-QVNUJKFWSA-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

Mexicanolide
Limonoid skeleton
Naphthopyran
Tetracarboxylic acid or derivatives
Naphthalene
Ortho ester
Fatty acid ester
Dihydropyranone
Carboxylic acid orthoester
Fatty acyl
Pyran
Meta-dioxane
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Furan
Cyclic alcohol
Meta-dioxolane
Orthocarboxylic acid derivative
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	4.1	ALOGPS
logP	5.24	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	13.04	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	166.26 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	179.17 m³·mol⁻¹	ChemAxon
Polarizability	73.87 Å³	ChemAxon
Number of Rings	8	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

C00034898

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

101396720

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Abdelgaleil SA, Doe M, Nakatani M: Rings B,D-seco limonoid antifeedants from Swietenia mahogani. Phytochemistry. 2013 Dec;96:312-7. doi: 10.1016/j.phytochem.2013.08.006. Epub 2013 Sep 10. [PubMed:24034555 ]
LOTUS database [Link]

MOL for NP0151715 ((4r,5r,14s,16r,18r,19s,20r,22s)-15-(acetyloxy)-5-(furan-3-yl)-16-hydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-12-(sec-butyl)-6,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]docos-8-en-22-yl (2e)-2-methylbut-2-enoate)

3D MOL for NP0151715 ((4r,5r,14s,16r,18r,19s,20r,22s)-15-(acetyloxy)-5-(furan-3-yl)-16-hydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-12-(sec-butyl)-6,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]docos-8-en-22-yl (2e)-2-methylbut-2-enoate)

3D SDF for NP0151715 ((4r,5r,14s,16r,18r,19s,20r,22s)-15-(acetyloxy)-5-(furan-3-yl)-16-hydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-12-(sec-butyl)-6,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]docos-8-en-22-yl (2e)-2-methylbut-2-enoate)

3D-SDF for NP0151715 ((4r,5r,14s,16r,18r,19s,20r,22s)-15-(acetyloxy)-5-(furan-3-yl)-16-hydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-12-(sec-butyl)-6,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]docos-8-en-22-yl (2e)-2-methylbut-2-enoate)

PDB for NP0151715 ((4r,5r,14s,16r,18r,19s,20r,22s)-15-(acetyloxy)-5-(furan-3-yl)-16-hydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-12-(sec-butyl)-6,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]docos-8-en-22-yl (2e)-2-methylbut-2-enoate)

3D PDB for NP0151715 ((4r,5r,14s,16r,18r,19s,20r,22s)-15-(acetyloxy)-5-(furan-3-yl)-16-hydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-12-(sec-butyl)-6,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]docos-8-en-22-yl (2e)-2-methylbut-2-enoate)

SMILES for NP0151715 ((4r,5r,14s,16r,18r,19s,20r,22s)-15-(acetyloxy)-5-(furan-3-yl)-16-hydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-12-(sec-butyl)-6,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]docos-8-en-22-yl (2e)-2-methylbut-2-enoate)

INCHI for NP0151715 ((4r,5r,14s,16r,18r,19s,20r,22s)-15-(acetyloxy)-5-(furan-3-yl)-16-hydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-12-(sec-butyl)-6,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]docos-8-en-22-yl (2e)-2-methylbut-2-enoate)