NP-MRD: Showing NP-Card for (-)-Rubralin D (NP0077082)

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Record Information

Version

2.0

Created at

2022-04-28 22:15:00 UTC

Updated at

2022-04-28 22:15:00 UTC

NP-MRD ID

NP0077082

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Rubralin D

Description

[(1R,2R,3S,7S,8R,10R,11R,15R,16S,17S)-3,17-bis(acetyloxy)-15-(furan-3-yl)-10-{[(2R)-2-hydroxy-3-methylbutanoyl]oxy}-2,7,11,16-tetramethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]Octadec-12-en-7-yl]methyl (2S,3S)-2,3-dihydroxy-3-methylpentanoate 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. (-)-Rubralin D is found in Cipadessa baccifera . Based on a literature review very few articles have been published on [(1R,2R,3S,7S,8R,10R,11R,15R,16S,17S)-3,17-bis(acetyloxy)-15-(furan-3-yl)-10-{[(2R)-2-hydroxy-3-methylbutanoyl]oxy}-2,7,11,16-tetramethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]Octadec-12-en-7-yl]methyl (2S,3S)-2,3-dihydroxy-3-methylpentanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200152D          

 55 59  0  0  1  0            999 V2000
    2.8816   -0.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6112    0.1479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1510    0.7718    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9612    0.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6190    1.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2959    0.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0564   -0.1470    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2316   -0.1633    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6918   -0.7871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9621   -1.5666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4223   -2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6926   -2.9699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6121   -2.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5819   -0.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5544   -0.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3793   -0.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6496   -1.5679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9919   -2.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3150   -1.5943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8807    1.5512    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0705    1.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5307    1.0829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8010    0.3035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3602   -0.3939    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5401   -0.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0417    0.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211   -0.1694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0530    0.9205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7527    1.3575    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3001    2.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5236    2.0002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9762    2.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6051    3.4268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7998    2.6429    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2525    3.3326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7051    4.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5287    3.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5627    3.7852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9422    2.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1709    1.9060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0447    2.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7972   -1.0936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4097   -1.8220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467   -2.5217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5852   -1.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1289   -0.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4205    2.1751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1502    2.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3400    3.1101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6900    3.5784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4197    4.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6095    4.5134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9595    4.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5002    3.4228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6909    1.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  8 14  1  1  0  0  0
  7 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 15 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  1  1  0  0  0
 35 39  1  1  0  0  0
 34 40  1  1  0  0  0
 29 41  1  1  0  0  0
 24 42  1  1  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
 23 46  1  6  0  0  0
 20 47  1  1  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 50 54  1  1  0  0  0
  3 55  1  6  0  0  0
M  END

     RDKit          3D

113117  0  0  0  0  0  0  0  0999 V2000
    9.3096    1.1587   -1.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1822    1.0449   -0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7490    0.8912    0.3354 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7016    0.7822    1.8434 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2147   -0.2855   -0.1824 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8921    2.0621   -0.1229 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3678    3.2577    0.3553 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5036    1.7549    0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0351    2.6209    1.1693 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8117    0.6717    0.1055 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6129    0.0830    0.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4430    0.6648   -0.3089 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4008    2.1505   -0.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6095    0.6307   -1.7669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7528   -0.4737   -2.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4235   -0.3732   -3.5845 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482   -1.7887   -2.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7558   -1.5384   -1.7219 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2616   -0.3784   -2.3094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376   -0.1862   -3.1941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0929    1.1927   -3.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3808   -1.1474   -3.6219 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7320   -1.2780   -0.2089 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4343   -2.3768    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0897    0.1344    0.0455 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6111    0.7667    1.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4326    2.3827    1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4757    2.5940    2.2443 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4158   -1.4980    2.6110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6092   -1.1062    1.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3331   -0.8083    2.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7411   -1.2182    2.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7174   -2.2083    1.4568 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0104   -2.0482    0.7736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8331   -3.0280    0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9484   -2.4076   -0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8426   -1.1361   -0.1075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7284   -0.8674    0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5008   -1.7693    0.6763 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9498   -0.9395   -0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7132   -2.9920    0.2751 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5258   -3.7792   -0.5618 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0172   -0.2007   -1.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7848   -1.0058    0.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4415    0.1320    1.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4685    2.5937   -0.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2069    2.6186   -0.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5020    2.4756    0.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9957   -2.3872   -3.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250   -2.3466   -1.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -2.4739   -1.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9078    1.1986   -4.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    1.4015   -3.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7232    4.5663    2.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3399    4.9570   -1.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8935    6.0299   -1.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6376   -1.2778    2.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9464   -0.3064    3.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9862   -1.8276    3.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4600   -0.4142    2.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
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 46103  1  0
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 43101  1  0
M  END


  Mrv1652304292200152D          

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  7  8  1  0  0  0  0
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 51 53  1  0  0  0  0
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  3 55  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0077082

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@](C)(O)[C@H](O)C(=O)OC[C@@]1(C)OC(=O)C[C@H](OC(C)=O)[C@]2(C)[C@H]3C[C@H](OC(C)=O)[C@@]4(C)[C@@H](CC=C4[C@]3(C)[C@@H](C[C@@H]12)OC(=O)[C@H](O)C(C)C)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C41H58O14/c1-11-37(6,49)34(46)36(48)51-20-38(7)27-16-30(54-35(47)33(45)21(2)3)40(9)26-13-12-25(24-14-15-50-19-24)39(26,8)29(52-22(4)42)17-28(40)41(27,10)31(53-23(5)43)18-32(44)55-38/h13-15,19,21,25,27-31,33-34,45-46,49H,11-12,16-18,20H2,1-10H3/t25-,27-,28-,29-,30+,31-,33+,34+,37-,38+,39-,40-,41-/m0/s1

> <INCHI_KEY>
UMSDVYJDIIBTJE-BIYQOGBXSA-N

> <FORMULA>
C41H58O14

> <MOLECULAR_WEIGHT>
774.901

> <EXACT_MASS>
774.382656548

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
113

> <JCHEM_AVERAGE_POLARIZABILITY>
81.4494849439326

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2R,3S,7S,8R,10R,11R,15R,16S,17S)-3,17-bis(acetyloxy)-15-(furan-3-yl)-10-{[(2R)-2-hydroxy-3-methylbutanoyl]oxy}-2,7,11,16-tetramethyl-5-oxo-6-oxatetracyclo[9.7.0.0^{2,8}.0^{12,16}]octadec-12-en-7-yl]methyl (2S,3S)-2,3-dihydroxy-3-methylpentanoate

> <ALOGPS_LOGP>
4.27

> <JCHEM_LOGP>
3.1675623906666637

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.539327828572194

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.552039866302405

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8775417152961142

> <JCHEM_POLAR_SURFACE_AREA>
205.32999999999996

> <JCHEM_REFRACTIVITY>
193.8671000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2R,3S,7S,8R,10R,11R,15R,16S,17S)-3,17-bis(acetyloxy)-15-(furan-3-yl)-10-{[(2R)-2-hydroxy-3-methylbutanoyl]oxy}-2,7,11,16-tetramethyl-5-oxo-6-oxatetracyclo[9.7.0.0^{2,8}.0^{12,16}]octadec-12-en-7-yl]methyl (2S,3S)-2,3-dihydroxy-3-methylpentanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       5.379  -1.179   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.874   0.276   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.882   1.441   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.394   1.150   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.622   2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.886   1.199   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.439  -0.274   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.899  -0.305   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.891  -1.469   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.396  -2.924   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.388  -4.089   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.893  -5.544   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.876  -3.798   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.553  -1.699   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.368  -1.502   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.908  -1.472   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.413  -2.927   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      11.185  -3.856   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.921  -2.976   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.377   2.896   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.865   3.186   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.857   2.021   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.362   0.566   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.539  -0.735   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.008  -0.903   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.078   0.188   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.533  -0.316   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.099   1.718   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.405   2.534   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.560   3.822   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.977   3.734   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.822   5.021   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.130   6.397   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -3.360   4.933   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.205   6.221   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.049   7.508   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.587   7.421   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -2.917   7.066   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -5.492   5.376   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -4.052   3.558   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       1.950   3.974   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       3.355  -2.041   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       2.631  -3.401   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       3.447  -4.707   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       1.092  -3.454   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       3.974  -0.847   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       6.385   4.060   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       5.880   5.515   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       4.368   5.805   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       6.888   6.680   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.383   8.135   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       4.871   8.425   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       7.391   9.299   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       8.400   6.389   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0       6.890   2.605   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3   23                                                  
CONECT    3    2    4   20   55                                             
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    4    9   14                                             
CONECT    9    8    1   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8                                                            
CONECT   15    7   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15                                                       
CONECT   20    3   21   47                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   29                                                  
CONECT   23   22    2   24   46                                             
CONECT   24   23   25   42                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   22   30   41                                             
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   40                                                  
CONECT   35   34   36   38   39                                             
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35                                                            
CONECT   39   35                                                            
CONECT   40   34                                                            
CONECT   41   29                                                            
CONECT   42   24   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   23                                                            
CONECT   47   20   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   54                                                  
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51                                                            
CONECT   54   50                                                            
CONECT   55    3                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  118    0
END

View in JSmol

Synonyms

Value	Source
[(1R,2R,3S,7S,8R,10R,11R,15R,16S,17S)-3,17-Bis(acetyloxy)-15-(furan-3-yl)-10-{[(2R)-2-hydroxy-3-methylbutanoyl]oxy}-2,7,11,16-tetramethyl-5-oxo-6-oxatetracyclo[9.7.0.0,.0,]octadec-12-en-7-yl]methyl (2S,3S)-2,3-dihydroxy-3-methylpentanoic acid	Generator

Chemical Formula

C₄₁H₅₈O₁₄

Average Mass

774.9010 Da

Monoisotopic Mass

774.38266 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@](C)(O)[C@H](O)C(=O)OC[C@@]1(C)OC(=O)C[C@H](OC(C)=O)[C@]2(C)[C@H]3C[C@H](OC(C)=O)[C@@]4(C)[C@@H](CC=C4[C@]3(C)[C@@H](C[C@@H]12)OC(=O)[C@H](O)C(C)C)C1=COC=C1

InChI Identifier

InChI=1S/C41H58O14/c1-11-37(6,49)34(46)36(48)51-20-38(7)27-16-30(54-35(47)33(45)21(2)3)40(9)26-13-12-25(24-14-15-50-19-24)39(26,8)29(52-22(4)42)17-28(40)41(27,10)31(53-23(5)43)18-32(44)55-38/h13-15,19,21,25,27-31,33-34,45-46,49H,11-12,16-18,20H2,1-10H3/t25-,27-,28-,29-,30+,31-,33+,34+,37-,38+,39-,40-,41-/m0/s1

InChI Key

UMSDVYJDIIBTJE-BIYQOGBXSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cipadessa baccifera	Plant	KNApSAcK

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
Caprolactone
Oxepane
Fatty acid ester
Fatty acyl
Monosaccharide
Heteroaromatic compound
Tertiary alcohol
Furan
Secondary alcohol
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	4.27	ALOGPS
logP	3.17	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	11.55	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	205.33 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	193.87 m³·mol⁻¹	ChemAxon
Polarizability	81.45 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

162990612

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Rubralin D (NP0077082)

MOL for NP0077082 ((-)-Rubralin D)

3D MOL for NP0077082 ((-)-Rubralin D)

3D SDF for NP0077082 ((-)-Rubralin D)

3D-SDF for NP0077082 ((-)-Rubralin D)

PDB for NP0077082 ((-)-Rubralin D)

3D PDB for NP0077082 ((-)-Rubralin D)

SMILES for NP0077082 ((-)-Rubralin D)

INCHI for NP0077082 ((-)-Rubralin D)

Structure for NP0077082 ((-)-Rubralin D)

3D Structure for NP0077082 ((-)-Rubralin D)