NP-MRD: Showing NP-Card for 12-O-methyl-1-O-deacetylnimbolinin B, meliatoosenin M (NP0040901)

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Record Information

Version

2.0

Created at

2021-06-20 22:56:36 UTC

Updated at

2021-06-30 00:15:07 UTC

NP-MRD ID

NP0040901

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-O-methyl-1-O-deacetylnimbolinin B, meliatoosenin M

Provided By

JEOL Database JEOL Logo

Description

Meliatoosenin M 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. 12-O-methyl-1-O-deacetylnimbolinin B, meliatoosenin M is found in Melia toosendan. 12-O-methyl-1-O-deacetylnimbolinin B, meliatoosenin M was first documented in 2011 (Hu, J.-F., et al.). Based on a literature review very few articles have been published on Meliatoosenin M.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100563D          

 89 94  0  0  0  0            999 V2000
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M  END

     RDKit          3D

 89 94  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306212100563D          

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M  END
> <DATABASE_ID>
NP0040901

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])([H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]2(C([H])([H])[H])C([H])([H])O[C@]3([H])[C@]2([H])[C@@]1(C([H])([H])[H])[C@@]1([H])C([H])([H])[C@]([H])(OC([H])([H])[H])O[C@]2([H])C(=C(C([H])([H])[H])[C@]([H])(C4=C([H])OC([H])=C4[H])C2([H])[H])[C@]1(C([H])([H])[H])[C@]3([H])OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C34H46O9/c1-9-17(2)31(37)43-30-28-29-32(5,16-40-28)25(41-19(4)35)14-24(36)33(29,6)23-13-26(38-8)42-22-12-21(20-10-11-39-15-20)18(3)27(22)34(23,30)7/h9-11,15,21-26,28-30,36H,12-14,16H2,1-8H3/b17-9+/t21-,22+,23-,24+,25-,26-,28-,29+,30-,32-,33+,34-/m1/s1

> <INCHI_KEY>
XCDNZCAJSVCMDQ-ZNNDDTJDSA-N

> <FORMULA>
C34H46O9

> <MOLECULAR_WEIGHT>
598.733

> <EXACT_MASS>
598.314183061

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
64.02751654194294

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0^{2,11}.0^{6,10}.0^{16,20}]icos-9-en-12-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
4.79

> <JCHEM_LOGP>
3.745711453666666

> <ALOGPS_LOGS>
-4.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.600801380121798

> <JCHEM_PKA_STRONGEST_BASIC>
-2.828914340063182

> <JCHEM_POLAR_SURFACE_AREA>
113.66000000000001

> <JCHEM_REFRACTIVITY>
157.4724

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0^{2,11}.0^{6,10}.0^{16,20}]icos-9-en-12-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 89 94  0  0  0  0  0  0  0  0999 V2000
    6.1564   -0.3495    1.4866 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7657   -0.4220    2.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6673   -0.9194    1.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6160   -1.5513    0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3882   -0.8521    2.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3146   -0.5955    3.3955 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3512   -1.0807    1.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124   -1.0869    1.9277 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5968   -2.4748    1.6665 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1912   -3.5773    2.1728 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2861   -4.5948    1.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7837   -4.2483    0.0780 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1141   -4.8763    0.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4977   -4.6431   -1.3886 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8935   -4.4009   -1.6831 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4129   -5.0504   -2.7584 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8273   -4.6109   -2.9807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8288   -5.8794   -3.4416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3885   -3.8072   -2.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3473   -2.2656   -2.1387 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0872   -1.8085   -2.6363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5813   -1.8293   -0.6348 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0843   -2.0014   -0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -0.3462   -0.3290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8717    0.7243   -1.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0039    1.8433   -1.6945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0814    1.2651   -2.6246 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5557    2.2573   -3.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3900    2.6456   -0.7005 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5851    1.9957    0.1017 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5289    3.0603    0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0257    3.3669    2.0768 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2462    4.6424    2.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0222    4.9610    1.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3131    6.2495    1.9896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3136    6.7540    2.7548 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6242    5.7803    2.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2111    2.1389    2.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208    1.9309    3.8592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0533    1.3805    1.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8311    0.0462    1.2167 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1818    0.2272    1.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6677   -2.7381    0.1854 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5219    0.6801    1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8193   -0.9862    2.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2361   -0.6530    0.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6679   -0.0080    3.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1166   -2.5255    0.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6054   -1.7329   -0.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0665   -0.9119   -0.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0538   -0.9369    3.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5738   -2.5402    2.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3077   -4.5465    0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1485   -5.5789    1.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9407   -4.6817   -0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4177   -4.5374    1.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0140   -5.9675    0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7034   -5.7131   -1.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4394   -4.8818   -2.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2280   -5.1124   -3.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8574   -3.5314   -3.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0753   -4.0080   -3.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4235   -4.1545   -2.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1135   -1.8192   -2.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1433   -0.8432   -2.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6520   -1.0868   -0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2739   -2.2935    0.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5538   -2.7654   -0.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0569   -0.3521   -0.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6528    1.1614   -0.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3808    0.2542   -1.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781    2.5046   -2.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2336    1.7526   -4.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1427    2.9397   -2.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834    2.8159   -4.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1941    1.2938   -0.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5379    2.6312    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5972    3.9494    0.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8957    3.4276    2.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6441    4.3226    0.9993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1450    6.9148    1.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4914    6.0397    3.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3859    0.9016    4.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9490    2.5807    4.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7453    2.1721    4.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0653    0.2125    3.0411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8976   -0.5609    1.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6629    1.1782    1.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3440   -2.5208   -0.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  1
 22 43  1  0
 40 38  2  0
 38 32  1  0
 32 31  1  0
 31 30  1  0
 33 37  2  0
 12 11  1  0
 24 69  1  6
 19 14  1  0
 14 15  1  0
 37 36  1  0
 36 35  1  0
 35 34  2  0
 34 33  1  0
 32 33  1  0
 19 20  1  0
  9 10  1  0
  8  7  1  0
 43 89  1  6
 14 12  1  0
 30 76  1  6
 22 24  1  0
 26 27  1  0
 11 10  1  0
 41 24  1  0
 38 39  1  0
 43  9  1  0
 20 21  1  0
 24 25  1  0
 15 16  1  0
 41 40  1  0
 16 17  1  0
  9  8  1  0
 16 18  2  0
 25 26  1  0
  7  5  1  0
  8 41  1  0
  5  6  2  0
 26 29  1  0
  5  3  1  0
 30 29  1  0
  3  2  2  0
 30 40  1  0
  3  4  1  0
 12 43  1  0
  2  1  1  0
 22 23  1  1
 27 28  1  0
 22 20  1  0
 41 42  1  1
 19 62  1  0
 19 63  1  0
 14 58  1  1
 20 64  1  6
  9 52  1  1
  8 51  1  1
 23 66  1  0
 23 67  1  0
 23 68  1  0
 13 55  1  0
 13 56  1  0
 13 57  1  0
 11 53  1  0
 11 54  1  0
 25 70  1  0
 25 71  1  0
 26 72  1  6
 32 79  1  1
 31 77  1  0
 31 78  1  0
 37 82  1  0
 35 81  1  0
 34 80  1  0
 39 83  1  0
 39 84  1  0
 39 85  1  0
 21 65  1  0
 17 59  1  0
 17 60  1  0
 17 61  1  0
  2 47  1  0
  4 48  1  0
  4 49  1  0
  4 50  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
 28 73  1  0
 28 74  1  0
 28 75  1  0
 42 86  1  0
 42 87  1  0
 42 88  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       6.156  -0.350   1.487  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.766  -0.422   2.029  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.667  -0.919   1.426  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.616  -1.551   0.066  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.388  -0.852   2.204  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.315  -0.596   3.396  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.351  -1.081   1.366  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.012  -1.087   1.928  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.597  -2.475   1.667  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.191  -3.577   2.173  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.286  -4.595   1.131  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.784  -4.248   0.078  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.114  -4.876   0.540  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.498  -4.643  -1.389  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.894  -4.401  -1.683  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.413  -5.050  -2.758  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.827  -4.611  -2.981  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.829  -5.879  -3.442  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.389  -3.807  -2.355  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.347  -2.266  -2.139  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.087  -1.809  -2.636  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.581  -1.829  -0.635  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.084  -2.001  -0.325  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.069  -0.346  -0.329  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.872   0.724  -1.112  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.004   1.843  -1.694  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.081   1.265  -2.625  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.556   2.257  -3.422  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.390   2.646  -0.701  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.585   1.996   0.102  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.529   3.060   0.668  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.026   3.367   2.077  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.246   4.642   2.181  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.022   4.961   1.611  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.313   6.250   1.990  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.314   6.754   2.755  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.624   5.780   2.868  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.211   2.139   2.417  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.121   1.931   3.859  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.053   1.381   1.328  0.00  0.00           C+0
HETATM   41  C   UNK     0      -0.831   0.046   1.217  0.00  0.00           C+0
HETATM   42  C   UNK     0      -2.182   0.227   1.954  0.00  0.00           C+0
HETATM   43  C   UNK     0      -0.668  -2.738   0.185  0.00  0.00           C+0
HETATM   44  H   UNK     0       6.522   0.680   1.557  0.00  0.00           H+0
HETATM   45  H   UNK     0       6.819  -0.986   2.080  0.00  0.00           H+0
HETATM   46  H   UNK     0       6.236  -0.653   0.441  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.668  -0.008   3.034  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.117  -2.526   0.113  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.605  -1.733  -0.360  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.067  -0.912  -0.633  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.054  -0.937   3.011  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.574  -2.540   2.155  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.308  -4.547   0.740  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.149  -5.579   1.590  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.941  -4.682  -0.145  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.418  -4.537   1.535  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.014  -5.968   0.594  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.703  -5.713  -1.521  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.439  -4.882  -2.117  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.228  -5.112  -3.866  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.857  -3.531  -3.150  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.075  -4.008  -3.387  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.424  -4.154  -2.273  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.114  -1.819  -2.784  0.00  0.00           H+0
HETATM   65  H   UNK     0      -0.143  -0.843  -2.787  0.00  0.00           H+0
HETATM   66  H   UNK     0      -3.652  -1.087  -0.519  0.00  0.00           H+0
HETATM   67  H   UNK     0      -3.274  -2.293   0.710  0.00  0.00           H+0
HETATM   68  H   UNK     0      -3.554  -2.765  -0.950  0.00  0.00           H+0
HETATM   69  H   UNK     0      -0.057  -0.352  -0.748  0.00  0.00           H+0
HETATM   70  H   UNK     0      -2.653   1.161  -0.484  0.00  0.00           H+0
HETATM   71  H   UNK     0      -2.381   0.254  -1.960  0.00  0.00           H+0
HETATM   72  H   UNK     0      -1.678   2.505  -2.253  0.00  0.00           H+0
HETATM   73  H   UNK     0       1.234   1.753  -4.115  0.00  0.00           H+0
HETATM   74  H   UNK     0       1.143   2.940  -2.800  0.00  0.00           H+0
HETATM   75  H   UNK     0      -0.183   2.816  -4.004  0.00  0.00           H+0
HETATM   76  H   UNK     0       1.194   1.294  -0.477  0.00  0.00           H+0
HETATM   77  H   UNK     0       2.538   2.631   0.744  0.00  0.00           H+0
HETATM   78  H   UNK     0       1.597   3.949   0.031  0.00  0.00           H+0
HETATM   79  H   UNK     0       1.896   3.428   2.745  0.00  0.00           H+0
HETATM   80  H   UNK     0      -1.644   4.323   0.999  0.00  0.00           H+0
HETATM   81  H   UNK     0      -2.145   6.915   1.807  0.00  0.00           H+0
HETATM   82  H   UNK     0       1.491   6.040   3.459  0.00  0.00           H+0
HETATM   83  H   UNK     0      -0.386   0.902   4.097  0.00  0.00           H+0
HETATM   84  H   UNK     0      -0.949   2.581   4.158  0.00  0.00           H+0
HETATM   85  H   UNK     0       0.745   2.172   4.485  0.00  0.00           H+0
HETATM   86  H   UNK     0      -2.065   0.213   3.041  0.00  0.00           H+0
HETATM   87  H   UNK     0      -2.898  -0.561   1.740  0.00  0.00           H+0
HETATM   88  H   UNK     0      -2.663   1.178   1.700  0.00  0.00           H+0
HETATM   89  H   UNK     0       0.344  -2.521  -0.199  0.00  0.00           H+0
CONECT    1    2   44   45   46                                             
CONECT    2    3    1   47                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3   48   49   50                                             
CONECT    5    7    6    3                                                  
CONECT    6    5                                                            
CONECT    7    8    5                                                       
CONECT    8    7    9   41   51                                             
CONECT    9   10   43    8   52                                             
CONECT   10    9   11                                                       
CONECT   11   12   10   53   54                                             
CONECT   12   13   11   14   43                                             
CONECT   13   12   55   56   57                                             
CONECT   14   19   15   12   58                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   59   60   61                                             
CONECT   18   16                                                            
CONECT   19   14   20   62   63                                             
CONECT   20   19   21   22   64                                             
CONECT   21   20   65                                                       
CONECT   22   43   24   23   20                                             
CONECT   23   22   66   67   68                                             
CONECT   24   69   22   41   25                                             
CONECT   25   24   26   70   71                                             
CONECT   26   27   25   29   72                                             
CONECT   27   26   28                                                       
CONECT   28   27   73   74   75                                             
CONECT   29   26   30                                                       
CONECT   30   31   76   29   40                                             
CONECT   31   32   30   77   78                                             
CONECT   32   38   31   33   79                                             
CONECT   33   37   34   32                                                  
CONECT   34   35   33   80                                                  
CONECT   35   36   34   81                                                  
CONECT   36   37   35                                                       
CONECT   37   33   36   82                                                  
CONECT   38   40   32   39                                                  
CONECT   39   38   83   84   85                                             
CONECT   40   38   41   30                                                  
CONECT   41   24   40    8   42                                             
CONECT   42   41   86   87   88                                             
CONECT   43   22   89    9   12                                             
CONECT   44    1                                                            
CONECT   45    1                                                            
CONECT   46    1                                                            
CONECT   47    2                                                            
CONECT   48    4                                                            
CONECT   49    4                                                            
CONECT   50    4                                                            
CONECT   51    8                                                            
CONECT   52    9                                                            
CONECT   53   11                                                            
CONECT   54   11                                                            
CONECT   55   13                                                            
CONECT   56   13                                                            
CONECT   57   13                                                            
CONECT   58   14                                                            
CONECT   59   17                                                            
CONECT   60   17                                                            
CONECT   61   17                                                            
CONECT   62   19                                                            
CONECT   63   19                                                            
CONECT   64   20                                                            
CONECT   65   21                                                            
CONECT   66   23                                                            
CONECT   67   23                                                            
CONECT   68   23                                                            
CONECT   69   24                                                            
CONECT   70   25                                                            
CONECT   71   25                                                            
CONECT   72   26                                                            
CONECT   73   28                                                            
CONECT   74   28                                                            
CONECT   75   28                                                            
CONECT   76   30                                                            
CONECT   77   31                                                            
CONECT   78   31                                                            
CONECT   79   32                                                            
CONECT   80   34                                                            
CONECT   81   35                                                            
CONECT   82   37                                                            
CONECT   83   39                                                            
CONECT   84   39                                                            
CONECT   85   39                                                            
CONECT   86   42                                                            
CONECT   87   42                                                            
CONECT   88   42                                                            
CONECT   89   43                                                            
MASTER        0    0    0    0    0    0    0    0   89    0  188    0
END

RDKit          3D

89 94  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₄₆O₉

Average Mass

598.7330 Da

Monoisotopic Mass

598.31418 Da

IUPAC Name

(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0^{2,11}.0^{6,10}.0^{16,20}]icos-9-en-12-yl (2E)-2-methylbut-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C([H])([H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]2(C([H])([H])[H])C([H])([H])O[C@]3([H])[C@]2([H])[C@@]1(C([H])([H])[H])[C@@]1([H])C([H])([H])[C@]([H])(OC([H])([H])[H])O[C@]2([H])C(=C(C([H])([H])[H])[C@]([H])(C4=C([H])OC([H])=C4[H])C2([H])[H])[C@]1(C([H])([H])[H])[C@]3([H])OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H]

InChI Identifier

InChI=1S/C34H46O9/c1-9-17(2)31(37)43-30-28-29-32(5,16-40-28)25(41-19(4)35)14-24(36)33(29,6)23-13-26(38-8)42-22-12-21(20-10-11-39-15-20)18(3)27(22)34(23,30)7/h9-11,15,21-26,28-30,36H,12-14,16H2,1-8H3/b17-9+/t21-,22+,23-,24+,25-,26-,28-,29+,30-,32-,33+,34-/m1/s1

InChI Key

XCDNZCAJSVCMDQ-ZNNDDTJDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Melia azedarach var. toosendan	JEOL database	Hu, J.-F., et al, Phyto. Lett. 4, 292 (2011)

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
Oxepane
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Furan
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
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	4.79	ALOGPS
logP	3.75	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	14.6	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	113.66 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	157.47 m³·mol⁻¹	ChemAxon
Polarizability	64.03 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

56950631

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hu, J.-F., et al. (2011). Hu, J.-F., et al, Phyto. Lett. 4, 292 (2011). Phyto. Lett..

Showing NP-Card for 12-O-methyl-1-O-deacetylnimbolinin B, meliatoosenin M (NP0040901)

MOL for NP0040901 (12-O-methyl-1-O-deacetylnimbolinin B, meliatoosenin M)

3D MOL for NP0040901 (12-O-methyl-1-O-deacetylnimbolinin B, meliatoosenin M)

3D SDF for NP0040901 (12-O-methyl-1-O-deacetylnimbolinin B, meliatoosenin M)

3D-SDF for NP0040901 (12-O-methyl-1-O-deacetylnimbolinin B, meliatoosenin M)

PDB for NP0040901 (12-O-methyl-1-O-deacetylnimbolinin B, meliatoosenin M)

3D PDB for NP0040901 (12-O-methyl-1-O-deacetylnimbolinin B, meliatoosenin M)

SMILES for NP0040901 (12-O-methyl-1-O-deacetylnimbolinin B, meliatoosenin M)

INCHI for NP0040901 (12-O-methyl-1-O-deacetylnimbolinin B, meliatoosenin M)

Structure for NP0040901 (12-O-methyl-1-O-deacetylnimbolinin B, meliatoosenin M)

3D Structure for NP0040901 (12-O-methyl-1-O-deacetylnimbolinin B, meliatoosenin M)