NP-MRD: Showing NP-Card for aphanalide C (NP0041389)

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Record Information

Version

2.0

Created at

2021-06-20 23:18:46 UTC

Updated at

2021-06-30 00:15:52 UTC

NP-MRD ID

NP0041389

Secondary Accession Numbers

None

Natural Product Identification

Common Name

aphanalide C

Provided By

JEOL Database JEOL Logo

Description

Aphanalide C 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. aphanalide C is found in Aphanamixis polystachya. aphanalide C was first documented in 2012 (Wang, J.-S., et al.). Based on a literature review very few articles have been published on Aphanalide C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101183D          

 93 98  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306212101183D          

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M  END
> <DATABASE_ID>
NP0041389

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]([H])(C(=O)O[C@@]1([H])[C@]([H])(O[H])[C@@]2([H])[C@@]3(C([H])([H])[H])[C@]([H])(O[C@]33[C@]([H])(O[H])C([H])([H])[C@@]([H])(C4=C([H])OC([H])=C4[H])[C@]13C([H])([H])[H])C([H])([H])[C@]1([H])[C@]2(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C(=O)OC1(C([H])([H])[H])C([H])([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C34H48O11/c1-9-16(2)25(38)29(40)43-28-26(39)27-31(6)20(30(4,5)45-24(37)14-22(31)42-17(3)35)13-23-33(27,8)34(44-23)21(36)12-19(32(28,34)7)18-10-11-41-15-18/h10-11,15-16,19-23,25-28,36,38-39H,9,12-14H2,1-8H3/t16-,19+,20+,21-,22+,23-,25+,26-,27-,28+,31-,32-,33-,34+/m1/s1

> <INCHI_KEY>
UIIWYOJCIFBCRA-OXSGSFIOSA-N

> <FORMULA>
C34H48O11

> <MOLECULAR_WEIGHT>
632.747

> <EXACT_MASS>
632.319662366

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
93

> <JCHEM_AVERAGE_POLARIZABILITY>
66.40707492532876

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3S,8R,10R,12R,13R,15R,16R,17R,18R,19S)-3-(acetyloxy)-15-(furan-3-yl)-13,18-dihydroxy-2,7,7,16,19-pentamethyl-5-oxo-6,11-dioxapentacyclo[8.8.1.0^{2,8}.0^{12,16}.0^{12,19}]nonadecan-17-yl (2S,3R)-2-hydroxy-3-methylpentanoate

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
2.344547148666666

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.614925287990921

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.4478105297697

> <JCHEM_PKA_STRONGEST_BASIC>
-2.858136770482189

> <JCHEM_POLAR_SURFACE_AREA>
161.95999999999998

> <JCHEM_REFRACTIVITY>
156.96059999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3S,8R,10R,12R,13R,15R,16R,17R,18R,19S)-3-(acetyloxy)-15-(furan-3-yl)-13,18-dihydroxy-2,7,7,16,19-pentamethyl-5-oxo-6,11-dioxapentacyclo[8.8.1.0^{2,8}.0^{12,16}.0^{12,19}]nonadecan-17-yl (2S,3R)-2-hydroxy-3-methylpentanoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 93 98  0  0  0  0  0  0  0  0999 V2000
   -6.4551    1.1260    3.9955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9734    0.8603    2.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8673   -0.2135    2.4926 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3928   -1.5817    2.9477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3027   -0.2816    1.0591 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2967   -0.8133    0.1804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9906   -1.0768    0.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8110   -2.0036    0.1853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0241   -0.5484    1.7698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6717   -1.0718    1.6222 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1399   -0.6981    0.1895 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3115   -1.7730   -0.7296 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3308   -0.2846    0.2045 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1246   -1.2523    1.1149 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1877   -2.7188    0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4368   -0.5927    1.5483 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2098    0.2217    0.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3426    1.0570   -0.4630 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2362    1.9052   -1.4443 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3512    1.1193   -2.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9396    3.0369   -0.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3960    2.6349   -2.3658 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9683    1.9722   -3.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6390    1.8305   -4.4718 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5463    1.5304   -3.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1291    1.1150   -1.9225 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8142    2.3011   -1.1487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4430    2.8086   -1.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658    4.0398   -0.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3507    2.3293   -1.9143 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1193    0.2094   -1.0823 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6009   -0.9541   -1.9629 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6779    0.1901    2.5492 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7052   -0.9591    2.6134 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1040   -1.8421    3.8248 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9001   -3.2205    3.5300 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1297   -1.4246    4.9127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1867   -1.3259    4.1374 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3239   -0.8351    4.9810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3893    0.3009    5.8410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6400    0.2960    6.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3468   -0.7793    5.9865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5430   -1.4666    5.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1947   -0.5336    2.8266 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0481    0.9895    3.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1558    1.9672    4.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6180    1.3783    4.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9769    0.2600    4.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8310    0.5749    1.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5880    1.8032    2.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0611    0.0875    3.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6416   -1.5734    4.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2940   -1.8709    2.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6419   -2.3641    2.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0688    0.7256    0.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8285   -1.1536   -0.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7342   -2.1658    1.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493    0.1281   -0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2414   -2.0810   -0.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2547    0.6629    0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4212   -2.8822   -0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9625   -3.2502    1.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2378   -3.2267    0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1439   -1.2591    2.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9077    0.8718    1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8278   -0.4782   -0.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8564    1.8163    0.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1106    0.7569   -1.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8609    1.7541   -2.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9701    0.2562   -2.7074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2102    3.6529   -0.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4601    3.7166   -1.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6741    2.6603    0.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9193    2.3489   -3.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4149    0.6766   -4.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2090    0.5379   -2.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5618    4.4719   -0.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4319    3.7808    0.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762    4.7791   -0.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7854   -1.6477   -2.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9887   -0.6235   -2.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4181   -1.5129   -1.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449   -1.7058    4.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1933   -3.7328    4.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0645   -2.1602    5.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -0.4581    5.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4517   -2.3543    3.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6210    1.0395    6.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1494    0.9453    7.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9687   -2.3737    4.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460    1.5842    2.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9892    1.2730    3.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6644    1.3358    3.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
 42 41  1  0
 41 40  2  0
 40 39  1  0
 38 39  1  0
 18 17  1  0
 23 24  2  0
 19 22  1  0
 18 67  1  1
 17 16  1  0
 19 20  1  6
 26 25  1  0
 16 33  1  0
 34 33  1  1
 13 11  1  0
 26 27  1  0
 22 23  1  0
 10  9  1  0
 25 23  1  0
 44 45  1  1
 44 34  1  0
 13 60  1  1
 14 34  1  0
 19 21  1  0
 44 10  1  0
 14 15  1  6
 10 11  1  0
 31 32  1  6
 16 14  1  0
 27 28  1  0
 13 14  1  0
 28 30  2  0
 34 35  1  0
 28 29  1  0
 35 37  1  0
 11 12  1  0
 37 38  1  0
  9  7  1  0
 38 44  1  0
  7  8  2  0
 39 43  2  0
  7  5  1  0
 31 18  1  0
  5  3  1  0
  3  2  1  0
 18 19  1  0
  3  4  1  0
 31 13  1  0
 35 36  1  0
 31 26  1  0
  5  6  1  0
 43 42  1  0
  2  1  1  0
 17 65  1  0
 17 66  1  0
 16 64  1  1
 10 57  1  6
 11 58  1  6
 26 76  1  6
 25 74  1  0
 25 75  1  0
 35 83  1  1
 37 85  1  0
 37 86  1  0
 38 87  1  6
 43 90  1  0
 41 89  1  0
 40 88  1  0
 20 68  1  0
 20 69  1  0
 20 70  1  0
 45 91  1  0
 45 92  1  0
 45 93  1  0
 21 71  1  0
 21 72  1  0
 21 73  1  0
 15 61  1  0
 15 62  1  0
 15 63  1  0
 32 80  1  0
 32 81  1  0
 32 82  1  0
 29 77  1  0
 29 78  1  0
 29 79  1  0
 12 59  1  0
  5 55  1  6
  3 51  1  1
  2 49  1  0
  2 50  1  0
  4 52  1  0
  4 53  1  0
  4 54  1  0
 36 84  1  0
  6 56  1  0
  1 46  1  0
  1 47  1  0
  1 48  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      -6.455   1.126   3.995  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.973   0.860   2.575  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.867  -0.214   2.493  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.393  -1.582   2.948  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.303  -0.282   1.059  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.297  -0.813   0.180  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.991  -1.077   0.970  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.811  -2.004   0.185  0.00  0.00           O+0
HETATM    9  O   UNK     0      -2.024  -0.548   1.770  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.672  -1.072   1.622  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.140  -0.698   0.190  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.312  -1.773  -0.730  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.331  -0.285   0.205  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.125  -1.252   1.115  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.188  -2.719   0.720  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.437  -0.593   1.548  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.210   0.222   0.518  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.343   1.057  -0.463  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.236   1.905  -1.444  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.351   1.119  -2.159  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.940   3.037  -0.657  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.396   2.635  -2.366  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.968   1.972  -3.458  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.639   1.831  -4.472  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.546   1.530  -3.336  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.129   1.115  -1.923  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.814   2.301  -1.149  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.443   2.809  -1.252  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.566   4.040  -0.408  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.351   2.329  -1.914  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.119   0.209  -1.082  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.601  -0.954  -1.963  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.678   0.190   2.549  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.705  -0.959   2.613  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.104  -1.842   3.825  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.900  -3.220   3.530  0.00  0.00           O+0
HETATM   37  C   UNK     0       1.130  -1.425   4.913  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.187  -1.326   4.137  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.324  -0.835   4.981  0.00  0.00           C+0
HETATM   40  C   UNK     0      -1.389   0.301   5.841  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.640   0.296   6.411  0.00  0.00           C+0
HETATM   42  O   UNK     0      -3.347  -0.779   5.987  0.00  0.00           O+0
HETATM   43  C   UNK     0      -2.543  -1.467   5.139  0.00  0.00           C+0
HETATM   44  C   UNK     0       0.195  -0.534   2.827  0.00  0.00           C+0
HETATM   45  C   UNK     0       0.048   0.990   3.038  0.00  0.00           C+0
HETATM   46  H   UNK     0      -7.156   1.967   4.002  0.00  0.00           H+0
HETATM   47  H   UNK     0      -5.618   1.378   4.654  0.00  0.00           H+0
HETATM   48  H   UNK     0      -6.977   0.260   4.412  0.00  0.00           H+0
HETATM   49  H   UNK     0      -6.831   0.575   1.954  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.588   1.803   2.168  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.061   0.088   3.171  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.642  -1.573   4.013  0.00  0.00           H+0
HETATM   53  H   UNK     0      -6.294  -1.871   2.397  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.642  -2.364   2.799  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.069   0.726   0.693  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.829  -1.154  -0.606  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.734  -2.166   1.693  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.749   0.128  -0.189  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.241  -2.081  -0.652  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.255   0.663   0.740  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.421  -2.882  -0.330  0.00  0.00           H+0
HETATM   62  H   UNK     0       2.962  -3.250   1.283  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.238  -3.227   0.912  0.00  0.00           H+0
HETATM   64  H   UNK     0       4.144  -1.259   2.064  0.00  0.00           H+0
HETATM   65  H   UNK     0       4.908   0.872   1.056  0.00  0.00           H+0
HETATM   66  H   UNK     0       4.828  -0.478  -0.055  0.00  0.00           H+0
HETATM   67  H   UNK     0       2.856   1.816   0.169  0.00  0.00           H+0
HETATM   68  H   UNK     0       6.111   0.757  -1.458  0.00  0.00           H+0
HETATM   69  H   UNK     0       5.861   1.754  -2.894  0.00  0.00           H+0
HETATM   70  H   UNK     0       4.970   0.256  -2.707  0.00  0.00           H+0
HETATM   71  H   UNK     0       4.210   3.653  -0.118  0.00  0.00           H+0
HETATM   72  H   UNK     0       5.460   3.717  -1.343  0.00  0.00           H+0
HETATM   73  H   UNK     0       5.674   2.660   0.061  0.00  0.00           H+0
HETATM   74  H   UNK     0       0.919   2.349  -3.706  0.00  0.00           H+0
HETATM   75  H   UNK     0       1.415   0.677  -4.011  0.00  0.00           H+0
HETATM   76  H   UNK     0       0.209   0.538  -2.071  0.00  0.00           H+0
HETATM   77  H   UNK     0      -1.562   4.472  -0.540  0.00  0.00           H+0
HETATM   78  H   UNK     0      -0.432   3.781   0.645  0.00  0.00           H+0
HETATM   79  H   UNK     0       0.176   4.779  -0.721  0.00  0.00           H+0
HETATM   80  H   UNK     0       1.785  -1.648  -2.188  0.00  0.00           H+0
HETATM   81  H   UNK     0       2.989  -0.624  -2.928  0.00  0.00           H+0
HETATM   82  H   UNK     0       3.418  -1.513  -1.502  0.00  0.00           H+0
HETATM   83  H   UNK     0       3.145  -1.706   4.134  0.00  0.00           H+0
HETATM   84  H   UNK     0       2.193  -3.733   4.305  0.00  0.00           H+0
HETATM   85  H   UNK     0       1.065  -2.160   5.722  0.00  0.00           H+0
HETATM   86  H   UNK     0       1.418  -0.458   5.341  0.00  0.00           H+0
HETATM   87  H   UNK     0      -0.452  -2.354   3.846  0.00  0.00           H+0
HETATM   88  H   UNK     0      -0.621   1.040   6.023  0.00  0.00           H+0
HETATM   89  H   UNK     0      -3.149   0.945   7.110  0.00  0.00           H+0
HETATM   90  H   UNK     0      -2.969  -2.374   4.732  0.00  0.00           H+0
HETATM   91  H   UNK     0       0.346   1.584   2.173  0.00  0.00           H+0
HETATM   92  H   UNK     0      -0.989   1.273   3.242  0.00  0.00           H+0
HETATM   93  H   UNK     0       0.664   1.336   3.874  0.00  0.00           H+0
CONECT    1    2   46   47   48                                             
CONECT    2    3    1   49   50                                             
CONECT    3    5    2    4   51                                             
CONECT    4    3   52   53   54                                             
CONECT    5    7    3    6   55                                             
CONECT    6    5   56                                                       
CONECT    7    9    8    5                                                  
CONECT    8    7                                                            
CONECT    9   10    7                                                       
CONECT   10    9   44   11   57                                             
CONECT   11   13   10   12   58                                             
CONECT   12   11   59                                                       
CONECT   13   11   60   14   31                                             
CONECT   14   34   15   16   13                                             
CONECT   15   14   61   62   63                                             
CONECT   16   17   33   14   64                                             
CONECT   17   18   16   65   66                                             
CONECT   18   17   67   31   19                                             
CONECT   19   22   20   21   18                                             
CONECT   20   19   68   69   70                                             
CONECT   21   19   71   72   73                                             
CONECT   22   19   23                                                       
CONECT   23   24   22   25                                                  
CONECT   24   23                                                            
CONECT   25   26   23   74   75                                             
CONECT   26   25   27   31   76                                             
CONECT   27   26   28                                                       
CONECT   28   27   30   29                                                  
CONECT   29   28   77   78   79                                             
CONECT   30   28                                                            
CONECT   31   32   18   13   26                                             
CONECT   32   31   80   81   82                                             
CONECT   33   16   34                                                       
CONECT   34   33   44   14   35                                             
CONECT   35   34   37   36   83                                             
CONECT   36   35   84                                                       
CONECT   37   35   38   85   86                                             
CONECT   38   39   37   44   87                                             
CONECT   39   40   38   43                                                  
CONECT   40   41   39   88                                                  
CONECT   41   42   40   89                                                  
CONECT   42   41   43                                                       
CONECT   43   39   42   90                                                  
CONECT   44   45   34   10   38                                             
CONECT   45   44   91   92   93                                             
CONECT   46    1                                                            
CONECT   47    1                                                            
CONECT   48    1                                                            
CONECT   49    2                                                            
CONECT   50    2                                                            
CONECT   51    3                                                            
CONECT   52    4                                                            
CONECT   53    4                                                            
CONECT   54    4                                                            
CONECT   55    5                                                            
CONECT   56    6                                                            
CONECT   57   10                                                            
CONECT   58   11                                                            
CONECT   59   12                                                            
CONECT   60   13                                                            
CONECT   61   15                                                            
CONECT   62   15                                                            
CONECT   63   15                                                            
CONECT   64   16                                                            
CONECT   65   17                                                            
CONECT   66   17                                                            
CONECT   67   18                                                            
CONECT   68   20                                                            
CONECT   69   20                                                            
CONECT   70   20                                                            
CONECT   71   21                                                            
CONECT   72   21                                                            
CONECT   73   21                                                            
CONECT   74   25                                                            
CONECT   75   25                                                            
CONECT   76   26                                                            
CONECT   77   29                                                            
CONECT   78   29                                                            
CONECT   79   29                                                            
CONECT   80   32                                                            
CONECT   81   32                                                            
CONECT   82   32                                                            
CONECT   83   35                                                            
CONECT   84   36                                                            
CONECT   85   37                                                            
CONECT   86   37                                                            
CONECT   87   38                                                            
CONECT   88   40                                                            
CONECT   89   41                                                            
CONECT   90   43                                                            
CONECT   91   45                                                            
CONECT   92   45                                                            
CONECT   93   45                                                            
MASTER        0    0    0    0    0    0    0    0   93    0  196    0
END

RDKit          3D

93 98  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₄₈O₁₁

Average Mass

632.7470 Da

Monoisotopic Mass

632.31966 Da

IUPAC Name

(1R,2R,3S,8R,10R,12R,13R,15R,16R,17R,18R,19S)-3-(acetyloxy)-15-(furan-3-yl)-13,18-dihydroxy-2,7,7,16,19-pentamethyl-5-oxo-6,11-dioxapentacyclo[8.8.1.0^{2,8}.0^{12,16}.0^{12,19}]nonadecan-17-yl (2S,3R)-2-hydroxy-3-methylpentanoate

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]O[C@]([H])(C(=O)O[C@@]1([H])[C@]([H])(O[H])[C@@]2([H])[C@@]3(C([H])([H])[H])[C@]([H])(O[C@]33[C@]([H])(O[H])C([H])([H])[C@@]([H])(C4=C([H])OC([H])=C4[H])[C@]13C([H])([H])[H])C([H])([H])[C@]1([H])[C@]2(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C(=O)OC1(C([H])([H])[H])C([H])([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C34H48O11/c1-9-16(2)25(38)29(40)43-28-26(39)27-31(6)20(30(4,5)45-24(37)14-22(31)42-17(3)35)13-23-33(27,8)34(44-23)21(36)12-19(32(28,34)7)18-10-11-41-15-18/h10-11,15-16,19-23,25-28,36,38-39H,9,12-14H2,1-8H3/t16-,19+,20+,21-,22+,23-,25+,26-,27-,28+,31-,32-,33-,34+/m1/s1

InChI Key

UIIWYOJCIFBCRA-OXSGSFIOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Aphanamixis polystachya	JEOL database	Wang, J.-S., et al, Tetrahedron 68, 3963 (2012)

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
Tricarboxylic acid or derivatives
Caprolactone
Fatty acid ester
Oxepane
Monosaccharide
Fatty acyl
Cyclic alcohol
Furan
Heteroaromatic compound
Lactone
Carboxylic acid ester
Oxetane
Secondary alcohol
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.41	ALOGPS
logP	2.34	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	12.45	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	161.96 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	156.96 m³·mol⁻¹	ChemAxon
Polarizability	66.41 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

101579588

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang, J.-S., et al. (2012). Wang, J.-S., et al, Tetrahedron 68, 3963 (2012). Tetrahedron.

Showing NP-Card for aphanalide C (NP0041389)

MOL for NP0041389 (aphanalide C)

3D MOL for NP0041389 (aphanalide C)

3D SDF for NP0041389 (aphanalide C)

3D-SDF for NP0041389 (aphanalide C)

PDB for NP0041389 (aphanalide C)

3D PDB for NP0041389 (aphanalide C)

SMILES for NP0041389 (aphanalide C)

INCHI for NP0041389 (aphanalide C)

Structure for NP0041389 (aphanalide C)

3D Structure for NP0041389 (aphanalide C)