NP-MRD: Showing NP-Card for yadanziolide V (NP0036366)

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Record Information

Version

2.0

Created at

2021-06-20 19:33:30 UTC

Updated at

2021-06-30 00:07:59 UTC

NP-MRD ID

NP0036366

Secondary Accession Numbers

None

Natural Product Identification

Common Name

yadanziolide V

Provided By

JEOL Database JEOL Logo

Description

Rel-Yadanziolide V belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. yadanziolide V is found in Brucea mollis. yadanziolide V was first documented in 2011 (Chen, H., et al.). Based on a literature review very few articles have been published on Rel-Yadanziolide V.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121333D          

 53 56  0  0  0  0            999 V2000
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    3.4134   -0.1037   -1.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8284    0.8769   -2.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9242    2.0041   -2.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9944    3.0658   -2.6102 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0029    1.6721   -1.0801 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2062    0.3174   -0.6406 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8718   -0.4898   -0.8265 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202121333D          

 53 56  0  0  0  0            999 V2000
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   -1.4866    0.0218    4.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7173   -1.0848    2.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5658    0.3793    0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4521    0.7061    2.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6297    2.0839    1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8971    1.7364    3.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7974    2.6115   -0.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9530    3.0217    1.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4645    2.1311   -1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1466    1.6471   -2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2215    0.7341    0.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142   -2.4756    0.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5009   -2.2739   -1.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8018   -1.1182   -0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 15  1  0  0  0  0
 23 24  1  0  0  0  0
 15 17  1  0  0  0  0
 26 27  1  6  0  0  0
 25 26  1  0  0  0  0
 15 16  1  0  0  0  0
 26 11  1  0  0  0  0
 11 38  1  1  0  0  0
  8 10  1  0  0  0  0
  8  9  1  6  0  0  0
 18 19  1  0  0  0  0
  8  7  1  0  0  0  0
 21 22  1  0  0  0  0
  8 25  1  0  0  0  0
 25 50  1  1  0  0  0
 19 20  1  0  0  0  0
 11 12  1  0  0  0  0
 17 41  1  1  0  0  0
 10 11  1  0  0  0  0
  7  6  1  0  0  0  0
 25 23  1  0  0  0  0
 26 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 21  1  0  0  0  0
  6  4  1  0  0  0  0
  4  3  1  0  0  0  0
  3  2  2  0  0  0  0
  2  7  1  0  0  0  0
 21 23  1  0  0  0  0
  4  5  2  0  0  0  0
 12 13  1  0  0  0  0
  2  1  1  0  0  0  0
 13 14  2  0  0  0  0
  7 32  1  1  0  0  0
 20 45  1  0  0  0  0
 10 36  1  0  0  0  0
 10 37  1  0  0  0  0
 15 39  1  6  0  0  0
 18 42  1  6  0  0  0
 21 46  1  6  0  0  0
 23 48  1  6  0  0  0
 24 49  1  0  0  0  0
 27 51  1  0  0  0  0
 27 52  1  0  0  0  0
 27 53  1  0  0  0  0
 16 40  1  0  0  0  0
  9 33  1  0  0  0  0
  9 34  1  0  0  0  0
  9 35  1  0  0  0  0
 19 43  1  0  0  0  0
 19 44  1  0  0  0  0
 22 47  1  0  0  0  0
  3 31  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036366

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@]2([H])[C@](C([H])([H])[H])(C([H])([H])[C@@]3([H])OC(=O)[C@]([H])(O[H])[C@]1([H])[C@@]23C([H])([H])[H])[C@]1([H])OC(=O)C([H])=C1C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O8/c1-7-4-10(21)27-16(7)18(2)5-9-19(3)11(13(23)17(25)26-9)8(6-20)12(22)14(24)15(18)19/h4,8-9,11-16,20,22-24H,5-6H2,1-3H3/t8-,9-,11-,12-,13-,14+,15-,16-,18+,19+/m1/s1

> <INCHI_KEY>
JEIWLRBHCNVSAV-RKMYCWCFSA-N

> <FORMULA>
C19H26O8

> <MOLECULAR_WEIGHT>
382.409

> <EXACT_MASS>
382.162767797

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.61919837087895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,4R,7R,8S,9S,10R,11R,12S)-7,10,11-trihydroxy-9-(hydroxymethyl)-2,12-dimethyl-2-[(2R)-3-methyl-5-oxo-2,5-dihydrofuran-2-yl]-5-oxatricyclo[6.3.1.0^{4,12}]dodecan-6-one

> <ALOGPS_LOGP>
-0.54

> <JCHEM_LOGP>
-1.174967480333333

> <ALOGPS_LOGS>
-1.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.403866902622713

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.076909772178363

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6368914305280713

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
91.22280000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4R,7R,8S,9S,10R,11R,12S)-7,10,11-trihydroxy-9-(hydroxymethyl)-2,12-dimethyl-2-[(2R)-3-methyl-5-oxo-2H-furan-2-yl]-5-oxatricyclo[6.3.1.0^{4,12}]dodecan-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
    4.0824   -1.4209   -1.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4134   -0.1037   -1.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8284    0.8769   -2.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9242    2.0041   -2.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9944    3.0658   -2.6102 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0029    1.6721   -1.0801 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2062    0.3174   -0.6406 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8718   -0.4898   -0.8265 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5834   -0.6755   -2.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654   -1.8734   -0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0446   -1.8428    1.0717 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6528   -1.3767    2.2339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0996   -0.9612    3.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1529   -1.2769    4.4363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1714    0.0752    2.9408 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0343    0.2478    4.0787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0213   -0.3051    1.7187 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9140    0.8498    1.1256 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8957    1.4742    2.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2429    2.3331    3.0548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0961    1.9349    0.3679 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3315    2.7238    1.2792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1315    1.3403   -0.6954 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8719    0.8640   -1.8113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917    0.2243   -0.0554 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1492   -0.9033    0.5844 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0581   -1.7201   -0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0164   -1.4689   -1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3293   -1.5973   -0.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4399   -2.2319   -1.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6685    0.9043   -2.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637    0.3640    0.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3702   -1.1717   -2.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5574    0.2842   -2.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3508   -1.2933   -2.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9685   -2.0786    0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7081   -2.6851   -0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4023   -2.8553    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6395    1.0195    2.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4866    0.0218    4.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7173   -1.0848    2.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5658    0.3793    0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4521    0.7061    2.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6297    2.0839    1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8971    1.7364    3.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7974    2.6115   -0.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9530    3.0217    1.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4645    2.1311   -1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1466    1.6471   -2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2215    0.7341    0.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142   -2.4756    0.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5009   -2.2739   -1.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8018   -1.1182   -0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 15  1  0
 23 24  1  0
 15 17  1  0
 26 27  1  6
 25 26  1  0
 15 16  1  0
 26 11  1  0
 11 38  1  1
  8 10  1  0
  8  9  1  6
 18 19  1  0
  8  7  1  0
 21 22  1  0
  8 25  1  0
 25 50  1  1
 19 20  1  0
 11 12  1  0
 17 41  1  1
 10 11  1  0
  7  6  1  0
 25 23  1  0
 26 17  1  0
 17 18  1  0
 18 21  1  0
  6  4  1  0
  4  3  1  0
  3  2  2  0
  2  7  1  0
 21 23  1  0
  4  5  2  0
 12 13  1  0
  2  1  1  0
 13 14  2  0
  7 32  1  1
 20 45  1  0
 10 36  1  0
 10 37  1  0
 15 39  1  6
 18 42  1  6
 21 46  1  6
 23 48  1  6
 24 49  1  0
 27 51  1  0
 27 52  1  0
 27 53  1  0
 16 40  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 19 43  1  0
 19 44  1  0
 22 47  1  0
  3 31  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       4.082  -1.421  -1.252  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.413  -0.104  -1.414  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.828   0.877  -2.216  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.924   2.004  -2.021  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.994   3.066  -2.610  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.003   1.672  -1.080  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.206   0.317  -0.641  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.872  -0.490  -0.827  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.583  -0.676  -2.329  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.965  -1.873  -0.097  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.045  -1.843   1.072  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.653  -1.377   2.234  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.100  -0.961   3.277  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.153  -1.277   4.436  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.171   0.075   2.941  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.034   0.248   4.079  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.021  -0.305   1.719  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.914   0.850   1.126  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.896   1.474   2.130  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.243   2.333   3.055  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.096   1.935   0.368  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.331   2.724   1.279  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.131   1.340  -0.695  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.872   0.864  -1.811  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.292   0.224  -0.055  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.149  -0.903   0.584  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.058  -1.720  -0.371  0.00  0.00           C+0
HETATM   28  H   UNK     0       5.016  -1.469  -1.822  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.329  -1.597  -0.200  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.440  -2.232  -1.606  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.668   0.904  -2.887  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.464   0.364   0.426  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.370  -1.172  -2.517  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.557   0.284  -2.856  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.351  -1.293  -2.808  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.968  -2.079   0.286  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.708  -2.685  -0.788  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.402  -2.855   1.293  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.640   1.020   2.810  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.487   0.022   4.863  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.717  -1.085   2.063  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.566   0.379   0.379  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.452   0.706   2.679  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.630   2.084   1.592  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.897   1.736   3.757  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.797   2.611  -0.136  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.953   3.022   1.981  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.465   2.131  -1.055  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.147   1.647  -2.322  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.222   0.734   0.774  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.614  -2.476   0.198  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.501  -2.274  -1.129  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.802  -1.118  -0.895  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    3    7    1                                                  
CONECT    3    4    2   31                                                  
CONECT    4    6    3    5                                                  
CONECT    5    4                                                            
CONECT    6    7    4                                                       
CONECT    7    8    6    2   32                                             
CONECT    8   10    9    7   25                                             
CONECT    9    8   33   34   35                                             
CONECT   10    8   11   36   37                                             
CONECT   11   26   38   12   10                                             
CONECT   12   11   13                                                       
CONECT   13   15   12   14                                                  
CONECT   14   13                                                            
CONECT   15   13   17   16   39                                             
CONECT   16   15   40                                                       
CONECT   17   15   41   26   18                                             
CONECT   18   19   17   21   42                                             
CONECT   19   18   20   43   44                                             
CONECT   20   19   45                                                       
CONECT   21   22   18   23   46                                             
CONECT   22   21   47                                                       
CONECT   23   24   25   21   48                                             
CONECT   24   23   49                                                       
CONECT   25   26    8   50   23                                             
CONECT   26   27   25   11   17                                             
CONECT   27   26   51   52   53                                             
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    3                                                            
CONECT   32    7                                                            
CONECT   33    9                                                            
CONECT   34    9                                                            
CONECT   35    9                                                            
CONECT   36   10                                                            
CONECT   37   10                                                            
CONECT   38   11                                                            
CONECT   39   15                                                            
CONECT   40   16                                                            
CONECT   41   17                                                            
CONECT   42   18                                                            
CONECT   43   19                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   23                                                            
CONECT   49   24                                                            
CONECT   50   25                                                            
CONECT   51   27                                                            
CONECT   52   27                                                            
CONECT   53   27                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  112    0
END

RDKit          3D

53 56  0  0  0  0  0  0  0  0999 V2000
    4.0824   -1.4209   -1.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9140    0.8498    1.1256 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8957    1.4742    2.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2429    2.3331    3.0548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0961    1.9349    0.3679 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3315    2.7238    1.2792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1315    1.3403   -0.6954 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8719    0.8640   -1.8113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917    0.2243   -0.0554 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1492   -0.9033    0.5844 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0581   -1.7201   -0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0164   -1.4689   -1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3293   -1.5973   -0.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4399   -2.2319   -1.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6685    0.9043   -2.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637    0.3640    0.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3702   -1.1717   -2.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5574    0.2842   -2.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3508   -1.2933   -2.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9685   -2.0786    0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7081   -2.6851   -0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4023   -2.8553    1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6395    1.0195    2.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4866    0.0218    4.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7173   -1.0848    2.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5658    0.3793    0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4521    0.7061    2.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6297    2.0839    1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8971    1.7364    3.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7974    2.6115   -0.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9530    3.0217    1.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4645    2.1311   -1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1466    1.6471   -2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2215    0.7341    0.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142   -2.4756    0.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5009   -2.2739   -1.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8018   -1.1182   -0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 15  1  0
 23 24  1  0
 15 17  1  0
 26 27  1  6
 25 26  1  0
 15 16  1  0
 26 11  1  0
 11 38  1  1
  8 10  1  0
  8  9  1  6
 18 19  1  0
  8  7  1  0
 21 22  1  0
  8 25  1  0
 25 50  1  1
 19 20  1  0
 11 12  1  0
 17 41  1  1
 10 11  1  0
  7  6  1  0
 25 23  1  0
 26 17  1  0
 17 18  1  0
 18 21  1  0
  6  4  1  0
  4  3  1  0
  3  2  2  0
  2  7  1  0
 21 23  1  0
  4  5  2  0
 12 13  1  0
  2  1  1  0
 13 14  2  0
  7 32  1  1
 20 45  1  0
 10 36  1  0
 10 37  1  0
 15 39  1  6
 18 42  1  6
 21 46  1  6
 23 48  1  6
 24 49  1  0
 27 51  1  0
 27 52  1  0
 27 53  1  0
 16 40  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 19 43  1  0
 19 44  1  0
 22 47  1  0
  3 31  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₆O₈

Average Mass

382.4090 Da

Monoisotopic Mass

382.16277 Da

IUPAC Name

(1R,2S,4R,7R,8S,9S,10R,11R,12S)-7,10,11-trihydroxy-9-(hydroxymethyl)-2,12-dimethyl-2-[(2R)-3-methyl-5-oxo-2,5-dihydrofuran-2-yl]-5-oxatricyclo[6.3.1.0^{4,12}]dodecan-6-one

Traditional Name

(1R,2S,4R,7R,8S,9S,10R,11R,12S)-7,10,11-trihydroxy-9-(hydroxymethyl)-2,12-dimethyl-2-[(2R)-3-methyl-5-oxo-2H-furan-2-yl]-5-oxatricyclo[6.3.1.0^{4,12}]dodecan-6-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@]2([H])[C@](C([H])([H])[H])(C([H])([H])[C@@]3([H])OC(=O)[C@]([H])(O[H])[C@]1([H])[C@@]23C([H])([H])[H])[C@]1([H])OC(=O)C([H])=C1C([H])([H])[H]

InChI Identifier

InChI=1S/C19H26O8/c1-7-4-10(21)27-16(7)18(2)5-9-19(3)11(13(23)17(25)26-9)8(6-20)12(22)14(24)15(18)19/h4,8-9,11-16,20,22-24H,5-6H2,1-3H3/t8-,9-,11-,12-,13-,14+,15-,16-,18+,19+/m1/s1

InChI Key

JEIWLRBHCNVSAV-RKMYCWCFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, 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
Brucea mollis	JEOL database	Chen, H., et al, J. Nat. Prod. 74, 2438 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Quassinoids

Alternative Parents

Substituents

Quassinoid
Delta valerolactone
Delta_valerolactone
2-furanone
Dicarboxylic acid or derivatives
Oxane
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Primary alcohol
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.54	ALOGPS
logP	-1.2	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	8.08	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.22 m³·mol⁻¹	ChemAxon
Polarizability	37.62 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

28486382

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56833964

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen, H., et al. (2011). Chen, H., et al, J. Nat. Prod. 74, 2438 (2011). J. Nat. Prod..

Showing NP-Card for yadanziolide V (NP0036366)

MOL for NP0036366 (yadanziolide V)

3D MOL for NP0036366 (yadanziolide V)

3D SDF for NP0036366 (yadanziolide V)

3D-SDF for NP0036366 (yadanziolide V)

PDB for NP0036366 (yadanziolide V)

3D PDB for NP0036366 (yadanziolide V)

SMILES for NP0036366 (yadanziolide V)

INCHI for NP0036366 (yadanziolide V)

Structure for NP0036366 (yadanziolide V)

3D Structure for NP0036366 (yadanziolide V)