NP-MRD: Showing NP-Card for ixerochinoside (NP0027878)

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Record Information

Version

2.0

Created at

2021-06-19 19:55:00 UTC

Updated at

2021-06-29 23:54:17 UTC

NP-MRD ID

NP0027878

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ixerochinoside

Provided By

JEOL Database JEOL Logo

Description

ixerochinoside is found in Ixeris chinensis. ixerochinoside was first documented in 2005 (PMID: 15635221). Based on a literature review very few articles have been published on ixerochinoside (PMID: 22506392).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121553D          

 90 95  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306192121553D          

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M  END
> <DATABASE_ID>
NP0027878

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C(=O)OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])C(=C([H])[H])[C@]3([H])[C@@]4([H])OC(=O)C(=C([H])[H])[C@]4([H])[C@]([H])(OC(=O)C([H])([H])C4=C([H])C([H])=C(O[H])C([H])=C4[H])C([H])([H])C(=C([H])[H])[C@]3([H])C2([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C37H40O13/c1-17-12-26(47-29(41)14-21-6-10-23(39)11-7-21)31-19(3)36(45)50-35(31)30-18(2)25(15-24(17)30)48-37-34(44)33(43)32(42)27(49-37)16-46-28(40)13-20-4-8-22(38)9-5-20/h4-11,24-27,30-35,37-39,42-44H,1-3,12-16H2/t24-,25-,26+,27+,30-,31+,32+,33-,34+,35+,37+/m0/s1

> <INCHI_KEY>
HMUFZGUGGDDWBV-ITNUQCNVSA-N

> <FORMULA>
C37H40O13

> <MOLECULAR_WEIGHT>
692.714

> <EXACT_MASS>
692.246891348

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
68.28100986745096

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-6-{[(3aR,4R,6aR,8S,9aR,9bR)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.6722465213333333

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.796201789162662

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.19497572706506

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490854558943226

> <JCHEM_POLAR_SURFACE_AREA>
198.50999999999996

> <JCHEM_REFRACTIVITY>
173.1795

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-6-{[(3aR,4R,6aR,8S,9aR,9bR)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (4-hydroxyphenyl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 90 95  0  0  0  0  0  0  0  0999 V2000
   -1.1479   -0.0529    3.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0404   -0.6545    2.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2402   -2.0654    3.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0632   -3.1599    2.4376 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1857   -2.9975    1.7343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3090   -3.4712    2.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3261   -4.0430    3.4222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5285   -3.2677    1.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6759   -1.8545    0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0353   -1.4575   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1051   -0.1332   -0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8194    0.7962    0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8914    2.1051   -0.2849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4764    0.4178    1.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4038   -0.9061    1.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2000   -3.1634    1.4120 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0903   -4.1643    0.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5084   -5.3692    0.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7484   -3.5783   -0.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9430   -4.1093   -1.9620 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1094   -2.3123   -0.5565 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3622   -1.8782    0.5953 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1289   -0.7848    1.3753 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7846    0.3034    0.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7918    0.1196   -0.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1927    1.6510    0.8467 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0007    2.4210   -0.3307 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4162    3.7771   -0.1617 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4676    4.5078    0.6253 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3979    5.1451   -0.0886 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6165    4.1558   -0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1624    3.6608   -1.9613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0536    2.8762   -2.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1914    2.6330   -2.2401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4525    2.3595   -3.9125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2860    0.8630   -3.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3234    0.0269   -4.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1696   -1.3605   -4.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0193   -1.9152   -3.8662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1213   -3.2750   -3.8480 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0613   -1.1012   -3.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9039    0.2860   -3.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9472    6.1636   -1.1074 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8744    7.5005   -0.5720 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4158    5.9079   -1.4676 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7265    6.5163   -2.7328 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7267    4.4196   -1.5317 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1175    4.2505   -1.8706 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8740    1.2817    1.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2243    0.0385    2.3408 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3624    0.9601    2.8616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699   -0.5653    3.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4811   -2.2534    4.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2279   -2.1499    3.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0688   -4.1353    2.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4170   -3.5390    2.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4786   -3.9756    0.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4592   -2.1712   -0.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5921    0.1528   -1.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3540    2.2227   -1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0348    1.1541    1.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9082   -1.1863    2.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1412   -3.3837    1.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5120   -5.9654   -0.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0166   -5.7977    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4066   -1.4841    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286   -1.2569    1.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.9543   -0.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2187   -0.8601   -0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8443    2.1438    1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3547    3.7836    0.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1520    5.6879    0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    4.6839   -0.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7761    3.3122   -0.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5157    2.8423   -4.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0967    2.6793   -4.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2613    0.4477   -4.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9750   -2.0076   -4.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9558   -3.5324   -3.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0001   -1.5253   -3.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7211    0.9096   -3.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3227    6.1951   -2.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2870    7.4918    0.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0851    6.3916   -0.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4192    7.4421   -2.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1822    3.9325   -2.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2623    4.8427   -2.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5067    2.1124    2.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1050    1.0647    0.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8664    0.3725    3.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 37 38  2  0
 36 35  1  0
 23 50  1  0
 39 41  2  0
 50  2  1  0
 23 22  1  0
 35 33  1  0
  2  3  1  0
  3  4  1  0
 16  4  1  0
 16 22  1  0
 33 32  1  0
 41 42  1  0
 33 34  2  0
 38 39  1  0
 28 47  1  0
 22 21  1  0
 21 19  1  0
 19 17  1  0
 16 17  1  0
 47 45  1  0
 24 25  2  3
 45 43  1  0
  2  1  2  3
 43 30  1  0
 17 18  2  3
 30 29  1  0
 19 20  2  0
 29 28  1  0
  4  5  1  0
  5  6  1  0
 43 44  1  0
  6  8  1  0
 45 46  1  0
  8  9  1  0
 47 48  1  0
  9 10  2  0
 10 11  1  0
 31 32  1  0
 11 12  2  0
 39 40  1  0
 12 14  1  0
 42 36  2  0
 14 15  2  0
 15  9  1  0
 36 37  1  0
 23 67  1  1
 50 49  1  0
 50 90  1  1
 49 26  1  0
 12 13  1  0
 26 24  1  0
  6  7  2  0
 26 27  1  0
 30 31  1  0
 28 27  1  0
 37 77  1  0
 38 78  1  0
 41 80  1  0
 42 81  1  0
 35 75  1  0
 35 76  1  0
 40 79  1  0
 28 71  1  1
 43 82  1  6
 44 83  1  0
 45 84  1  1
 46 85  1  0
 47 86  1  6
 48 87  1  0
 31 73  1  0
 31 74  1  0
 30 72  1  1
 49 88  1  0
 49 89  1  0
 26 70  1  1
  3 53  1  0
  3 54  1  0
  4 55  1  1
 16 63  1  1
 22 66  1  6
 25 68  1  0
 25 69  1  0
  1 51  1  0
  1 52  1  0
 18 64  1  0
 18 65  1  0
  8 56  1  0
  8 57  1  0
 10 58  1  0
 11 59  1  0
 14 61  1  0
 15 62  1  0
 13 60  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.148  -0.053   3.186  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.040  -0.655   2.992  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.240  -2.065   3.507  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.063  -3.160   2.438  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.186  -2.998   1.734  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.309  -3.471   2.339  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.326  -4.043   3.422  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.529  -3.268   1.468  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.676  -1.855   0.959  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.035  -1.458  -0.225  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.105  -0.133  -0.655  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.819   0.796   0.092  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.891   2.105  -0.285  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.476   0.418   1.256  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.404  -0.906   1.692  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.200  -3.163   1.412  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.090  -4.164   0.303  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.508  -5.369   0.267  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.748  -3.578  -0.884  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.943  -4.109  -1.962  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.109  -2.312  -0.557  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.362  -1.878   0.595  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.129  -0.785   1.375  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.785   0.303   0.525  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.792   0.120  -0.344  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.193   1.651   0.847  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.001   2.421  -0.331  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.416   3.777  -0.162  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.468   4.508   0.625  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.398   5.145  -0.089  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.617   4.156  -0.695  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.162   3.661  -1.961  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.054   2.876  -2.627  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.191   2.633  -2.240  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.453   2.360  -3.913  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.286   0.863  -3.911  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.323   0.027  -4.348  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.170  -1.361  -4.323  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.019  -1.915  -3.866  0.00  0.00           C+0
HETATM   40  O   UNK     0       0.121  -3.275  -3.848  0.00  0.00           O+0
HETATM   41  C   UNK     0       1.061  -1.101  -3.438  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.904   0.286  -3.445  0.00  0.00           C+0
HETATM   43  C   UNK     0       0.947   6.164  -1.107  0.00  0.00           C+0
HETATM   44  O   UNK     0       0.874   7.500  -0.572  0.00  0.00           O+0
HETATM   45  C   UNK     0       2.416   5.908  -1.468  0.00  0.00           C+0
HETATM   46  O   UNK     0       2.727   6.516  -2.733  0.00  0.00           O+0
HETATM   47  C   UNK     0       2.727   4.420  -1.532  0.00  0.00           C+0
HETATM   48  O   UNK     0       4.117   4.250  -1.871  0.00  0.00           O+0
HETATM   49  C   UNK     0       0.874   1.282   1.501  0.00  0.00           C+0
HETATM   50  C   UNK     0       1.224   0.039   2.341  0.00  0.00           C+0
HETATM   51  H   UNK     0      -1.362   0.960   2.862  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.970  -0.565   3.679  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.481  -2.253   4.314  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.228  -2.150   3.978  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.069  -4.135   2.943  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.417  -3.539   2.051  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.479  -3.976   0.632  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.459  -2.171  -0.811  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.592   0.153  -1.567  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.354   2.223  -1.100  0.00  0.00           H+0
HETATM   61  H   UNK     0      -5.035   1.154   1.826  0.00  0.00           H+0
HETATM   62  H   UNK     0      -4.908  -1.186   2.614  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.141  -3.384   1.936  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.512  -5.965  -0.643  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.017  -5.798   1.133  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.407  -1.484   0.223  0.00  0.00           H+0
HETATM   67  H   UNK     0       2.929  -1.257   1.963  0.00  0.00           H+0
HETATM   68  H   UNK     0       4.213   0.954  -0.898  0.00  0.00           H+0
HETATM   69  H   UNK     0       4.219  -0.860  -0.531  0.00  0.00           H+0
HETATM   70  H   UNK     0       2.844   2.144   1.581  0.00  0.00           H+0
HETATM   71  H   UNK     0       3.355   3.784   0.408  0.00  0.00           H+0
HETATM   72  H   UNK     0      -0.152   5.688   0.691  0.00  0.00           H+0
HETATM   73  H   UNK     0      -1.565   4.684  -0.849  0.00  0.00           H+0
HETATM   74  H   UNK     0      -0.776   3.312  -0.015  0.00  0.00           H+0
HETATM   75  H   UNK     0       0.516   2.842  -4.095  0.00  0.00           H+0
HETATM   76  H   UNK     0      -1.097   2.679  -4.740  0.00  0.00           H+0
HETATM   77  H   UNK     0      -2.261   0.448  -4.705  0.00  0.00           H+0
HETATM   78  H   UNK     0      -1.975  -2.008  -4.659  0.00  0.00           H+0
HETATM   79  H   UNK     0       0.956  -3.532  -3.400  0.00  0.00           H+0
HETATM   80  H   UNK     0       2.000  -1.525  -3.095  0.00  0.00           H+0
HETATM   81  H   UNK     0       1.721   0.910  -3.085  0.00  0.00           H+0
HETATM   82  H   UNK     0       0.323   6.195  -2.007  0.00  0.00           H+0
HETATM   83  H   UNK     0       1.287   7.492   0.312  0.00  0.00           H+0
HETATM   84  H   UNK     0       3.085   6.392  -0.744  0.00  0.00           H+0
HETATM   85  H   UNK     0       2.419   7.442  -2.667  0.00  0.00           H+0
HETATM   86  H   UNK     0       2.182   3.933  -2.345  0.00  0.00           H+0
HETATM   87  H   UNK     0       4.262   4.843  -2.636  0.00  0.00           H+0
HETATM   88  H   UNK     0       0.507   2.112   2.114  0.00  0.00           H+0
HETATM   89  H   UNK     0       0.105   1.065   0.748  0.00  0.00           H+0
HETATM   90  H   UNK     0       1.866   0.373   3.172  0.00  0.00           H+0
CONECT    1    2   51   52                                                  
CONECT    2   50    3    1                                                  
CONECT    3    2    4   53   54                                             
CONECT    4    3   16    5   55                                             
CONECT    5    4    6                                                       
CONECT    6    5    8    7                                                  
CONECT    7    6                                                            
CONECT    8    6    9   56   57                                             
CONECT    9    8   10   15                                                  
CONECT   10    9   11   58                                                  
CONECT   11   10   12   59                                                  
CONECT   12   11   14   13                                                  
CONECT   13   12   60                                                       
CONECT   14   12   15   61                                                  
CONECT   15   14    9   62                                                  
CONECT   16    4   22   17   63                                             
CONECT   17   19   16   18                                                  
CONECT   18   17   64   65                                                  
CONECT   19   21   17   20                                                  
CONECT   20   19                                                            
CONECT   21   22   19                                                       
CONECT   22   23   16   21   66                                             
CONECT   23   24   50   22   67                                             
CONECT   24   23   25   26                                                  
CONECT   25   24   68   69                                                  
CONECT   26   49   24   27   70                                             
CONECT   27   26   28                                                       
CONECT   28   47   29   27   71                                             
CONECT   29   30   28                                                       
CONECT   30   43   29   31   72                                             
CONECT   31   32   30   73   74                                             
CONECT   32   33   31                                                       
CONECT   33   35   32   34                                                  
CONECT   34   33                                                            
CONECT   35   36   33   75   76                                             
CONECT   36   35   42   37                                                  
CONECT   37   38   36   77                                                  
CONECT   38   37   39   78                                                  
CONECT   39   41   38   40                                                  
CONECT   40   39   79                                                       
CONECT   41   39   42   80                                                  
CONECT   42   41   36   81                                                  
CONECT   43   45   30   44   82                                             
CONECT   44   43   83                                                       
CONECT   45   47   43   46   84                                             
CONECT   46   45   85                                                       
CONECT   47   28   45   48   86                                             
CONECT   48   47   87                                                       
CONECT   49   50   26   88   89                                             
CONECT   50   23    2   49   90                                             
CONECT   51    1                                                            
CONECT   52    1                                                            
CONECT   53    3                                                            
CONECT   54    3                                                            
CONECT   55    4                                                            
CONECT   56    8                                                            
CONECT   57    8                                                            
CONECT   58   10                                                            
CONECT   59   11                                                            
CONECT   60   13                                                            
CONECT   61   14                                                            
CONECT   62   15                                                            
CONECT   63   16                                                            
CONECT   64   18                                                            
CONECT   65   18                                                            
CONECT   66   22                                                            
CONECT   67   23                                                            
CONECT   68   25                                                            
CONECT   69   25                                                            
CONECT   70   26                                                            
CONECT   71   28                                                            
CONECT   72   30                                                            
CONECT   73   31                                                            
CONECT   74   31                                                            
CONECT   75   35                                                            
CONECT   76   35                                                            
CONECT   77   37                                                            
CONECT   78   38                                                            
CONECT   79   40                                                            
CONECT   80   41                                                            
CONECT   81   42                                                            
CONECT   82   43                                                            
CONECT   83   44                                                            
CONECT   84   45                                                            
CONECT   85   46                                                            
CONECT   86   47                                                            
CONECT   87   48                                                            
CONECT   88   49                                                            
CONECT   89   49                                                            
CONECT   90   50                                                            
MASTER        0    0    0    0    0    0    0    0   90    0  190    0
END

RDKit          3D

90 95  0  0  0  0  0  0  0  0999 V2000
   -1.1479   -0.0529    3.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0404   -0.6545    2.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2402   -2.0654    3.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0632   -3.1599    2.4376 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1857   -2.9975    1.7343 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3261   -4.0430    3.4222 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1051   -0.1332   -0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8914    2.1051   -0.2849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4764    0.4178    1.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4038   -0.9061    1.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2000   -3.1634    1.4120 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.7484   -3.5783   -0.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7918    0.1196   -0.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0007    2.4210   -0.3307 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6165    4.1558   -0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3234    0.0269   -4.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1696   -1.3605   -4.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0193   -1.9152   -3.8662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1213   -3.2750   -3.8480 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0613   -1.1012   -3.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9039    0.2860   -3.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9472    6.1636   -1.1074 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8744    7.5005   -0.5720 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4158    5.9079   -1.4676 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7265    6.5163   -2.7328 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7267    4.4196   -1.5317 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1175    4.2505   -1.8706 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8740    1.2817    1.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2243    0.0385    2.3408 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.4786   -3.9756    0.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4592   -2.1712   -0.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5921    0.1528   -1.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3540    2.2227   -1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0348    1.1541    1.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9082   -1.1863    2.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1412   -3.3837    1.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5120   -5.9654   -0.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0166   -5.7977    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4066   -1.4841    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286   -1.2569    1.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.9543   -0.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2187   -0.8601   -0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8443    2.1438    1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3547    3.7836    0.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1520    5.6879    0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2613    0.4477   -4.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5067    2.1124    2.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8664    0.3725    3.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
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 37 38  2  0
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 30 31  1  0
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 37 77  1  0
 38 78  1  0
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 42 81  1  0
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 35 76  1  0
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 28 71  1  1
 43 82  1  6
 44 83  1  0
 45 84  1  1
 46 85  1  0
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 31 73  1  0
 31 74  1  0
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 49 89  1  0
 26 70  1  1
  3 53  1  0
  3 54  1  0
  4 55  1  1
 16 63  1  1
 22 66  1  6
 25 68  1  0
 25 69  1  0
  1 51  1  0
  1 52  1  0
 18 64  1  0
 18 65  1  0
  8 56  1  0
  8 57  1  0
 10 58  1  0
 11 59  1  0
 14 61  1  0
 15 62  1  0
 13 60  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₇H₄₀O₁₃

Average Mass

692.7140 Da

Monoisotopic Mass

692.24689 Da

IUPAC Name

[(2R,3S,4S,5R,6R)-6-{[(3aR,4R,6aR,8S,9aR,9bR)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate

Traditional Name

[(2R,3S,4S,5R,6R)-6-{[(3aR,4R,6aR,8S,9aR,9bR)-4-{[2-(4-hydroxyphenyl)acetyl]oxy}-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (4-hydroxyphenyl)acetate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C(=O)OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])C(=C([H])[H])[C@]3([H])[C@@]4([H])OC(=O)C(=C([H])[H])[C@]4([H])[C@]([H])(OC(=O)C([H])([H])C4=C([H])C([H])=C(O[H])C([H])=C4[H])C([H])([H])C(=C([H])[H])[C@]3([H])C2([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C37H40O13/c1-17-12-26(47-29(41)14-21-6-10-23(39)11-7-21)31-19(3)36(45)50-35(31)30-18(2)25(15-24(17)30)48-37-34(44)33(43)32(42)27(49-37)16-46-28(40)13-20-4-8-22(38)9-5-20/h4-11,24-27,30-35,37-39,42-44H,1-3,12-16H2/t24-,25-,26+,27+,30-,31+,32+,33-,34+,35+,37+/m0/s1

InChI Key

HMUFZGUGGDDWBV-ITNUQCNVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OH, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OH, 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
Ixeris chinensis	JEOL database	Khalil, A. T., et al, Chem. Pharm. Bull. 53, 15 (2005)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Terpene glycoside
Guaiane sesquiterpenoid
Sesquiterpenoid
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Gamma butyrolactone
Benzenoid
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Lactone
Carboxylic acid ester
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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	2.71	ALOGPS
logP	2.67	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	198.51 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	173.18 m³·mol⁻¹	ChemAxon
Polarizability	68.28 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9333366

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11158258

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Khalil AT, Shen YC, Guh JH, Cheng SY: Two new sesquiterpene lactones from Ixeris chinensis. Chem Pharm Bull (Tokyo). 2005 Jan;53(1):15-7. doi: 10.1248/cpb.53.15. [PubMed:15635221 ]
Wang JL, Lv D, Liang XY, Zhao M, Zhang SJ: [Study on chemical constituents of the Ixeris chinensis]. Zhong Yao Cai. 2011 Nov;34(11):1706-8. [PubMed:22506392 ]
Khalil, A. T., et al. (2005). Khalil, A. T., et al, Chem. Pharm. Bull. 53, 15 (2005). Chem. Pharm. Bull..

Showing NP-Card for ixerochinoside (NP0027878)

MOL for NP0027878 (ixerochinoside)

3D MOL for NP0027878 (ixerochinoside)

3D SDF for NP0027878 (ixerochinoside)

3D-SDF for NP0027878 (ixerochinoside)

PDB for NP0027878 (ixerochinoside)

3D PDB for NP0027878 (ixerochinoside)

SMILES for NP0027878 (ixerochinoside)

INCHI for NP0027878 (ixerochinoside)

Structure for NP0027878 (ixerochinoside)

3D Structure for NP0027878 (ixerochinoside)