NP-MRD: Showing NP-Card for aquilarisin (NP0040172)

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Record Information

Version

2.0

Created at

2021-06-20 22:24:37 UTC

Updated at

2021-06-30 00:13:56 UTC

NP-MRD ID

NP0040172

Secondary Accession Numbers

None

Natural Product Identification

Common Name

aquilarisin

Provided By

JEOL Database JEOL Logo

Description

Aquilarisin belongs to the class of organic compounds known as flavonoid-8-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C8-position. aquilarisin is found in Aquilaria sinensis. aquilarisin was first documented in 2011 (PMID: 21215978). Based on a literature review very few articles have been published on Aquilarisin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100243D          

 55 58  0  0  0  0            999 V2000
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    1.5573   -3.8137   -0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8811   -2.5076   -0.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9186   -2.2663    0.7097 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284   -1.4543   -0.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5038   -0.1734   -0.3487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6776    0.3883    0.6847 C   0  0  2  0  0  0  0  0  0  0  0  0
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 22 23  1  0  0  0  0
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 31 25  2  0  0  0  0
  6  7  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306212100243D          

 55 58  0  0  0  0            999 V2000
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    0.6025   -5.0911   -3.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8398   -5.6554   -0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921   -3.1522    0.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0891   -0.3909    1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6829    1.2313    1.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6608    3.1760   -0.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2916    3.6027    1.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4395    3.5952    3.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2980    1.0731    3.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3939    1.9333    3.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2988    1.7637    1.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8067   -0.5046    1.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5742   -0.4246   -2.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7490    1.7059   -3.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0098    4.7230   -3.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9786    3.7332   -3.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7922    1.6235   -3.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -2.1958   -3.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0  0  0  0
 35 33  1  0  0  0  0
 33 32  1  0  0  0  0
 32 24  2  0  0  0  0
 24 23  1  0  0  0  0
 26 27  2  0  0  0  0
 33 34  2  0  0  0  0
 24 25  1  0  0  0  0
  4  3  2  0  0  0  0
  8  9  1  0  0  0  0
  3 35  1  0  0  0  0
  4  5  1  0  0  0  0
 30 31  1  0  0  0  0
  2  1  1  0  0  0  0
 22  8  1  0  0  0  0
  8  6  2  0  0  0  0
 31 25  2  0  0  0  0
  6  7  1  0  0  0  0
  3  2  1  0  0  0  0
 22 35  2  0  0  0  0
 25 26  1  0  0  0  0
 28 29  1  0  0  0  0
 27 28  1  0  0  0  0
 10 20  1  0  0  0  0
 20 18  1  0  0  0  0
 18 16  1  0  0  0  0
 16 12  1  0  0  0  0
 12 11  1  0  0  0  0
 11 10  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 28 30  2  0  0  0  0
 13 15  1  0  0  0  0
  6  4  1  0  0  0  0
 13 14  2  0  0  0  0
 12 13  1  0  0  0  0
 10  9  1  0  0  0  0
 26 50  1  0  0  0  0
 27 51  1  0  0  0  0
 30 53  1  0  0  0  0
 31 54  1  0  0  0  0
 29 52  1  0  0  0  0
  7 40  1  0  0  0  0
 32 55  1  0  0  0  0
  5 39  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
 10 41  1  1  0  0  0
 16 44  1  6  0  0  0
 17 45  1  0  0  0  0
 18 46  1  1  0  0  0
 19 47  1  0  0  0  0
 20 48  1  6  0  0  0
 21 49  1  0  0  0  0
 12 42  1  1  0  0  0
 15 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040172

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]1([H])O[C@@]([H])(OC2=C(O[H])C(O[H])=C(OC([H])([H])[H])C3=C2OC(=C([H])C3=O)C2=C([H])C([H])=C(O[H])C([H])=C2[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O13/c1-32-17-11-9(24)6-10(7-2-4-8(23)5-3-7)33-18(11)19(15(28)14(17)27)34-22-16(29)12(25)13(26)20(35-22)21(30)31/h2-6,12-13,16,20,22-23,25-29H,1H3,(H,30,31)/t12-,13-,16+,20-,22+/m0/s1

> <INCHI_KEY>
XWWLMXDERFHTHA-DPOSBGKNSA-N

> <FORMULA>
C22H20O13

> <MOLECULAR_WEIGHT>
492.389

> <EXACT_MASS>
492.090390704

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
45.65680242537468

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-6-{[6,7-dihydroxy-2-(4-hydroxyphenyl)-5-methoxy-4-oxo-4H-chromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
-0.35234100899999926

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.264922083697206

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4836041233727393

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868292113191856

> <JCHEM_POLAR_SURFACE_AREA>
212.66999999999996

> <JCHEM_REFRACTIVITY>
113.36979999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-6-{[6,7-dihydroxy-2-(4-hydroxyphenyl)-5-methoxy-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
    0.8311   -5.7914   -2.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2452   -5.4051   -1.6338 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5001   -4.0845   -1.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5573   -3.8137   -0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2954   -4.8272    0.0600 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8811   -2.5076   -0.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9186   -2.2663    0.7097 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284   -1.4543   -0.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5038   -0.1734   -0.3487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6776    0.3883    0.6847 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1957    1.3569    0.1105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0452    1.9858    1.0758 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9376    2.9540    0.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5911    3.9737   -0.2638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2237    2.5409    0.2635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2230    2.7432    2.1201 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0582    3.2460    3.1701 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8054    1.7963    2.7476 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6675    2.5482    3.6173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6276    1.0620    1.6908 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4668    0.1087    2.3651 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0411   -1.7136   -1.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6703   -0.6284   -1.9431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8399   -0.8284   -2.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5838    0.4196   -2.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9866    0.4684   -2.8976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6632    1.6769   -3.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9432    2.8445   -3.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6397    4.0061   -3.4527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5557    2.8252   -3.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8814    1.6163   -3.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2613   -2.0322   -3.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4735   -3.2299   -2.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8280   -4.3226   -3.1337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2861   -3.0282   -1.8537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4270   -6.7714   -3.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165   -5.8881   -2.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6025   -5.0911   -3.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8398   -5.6554   -0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921   -3.1522    0.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0891   -0.3909    1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6829    1.2313    1.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6608    3.1760   -0.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2916    3.6027    1.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4395    3.5952    3.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2980    1.0731    3.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3939    1.9333    3.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2988    1.7637    1.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8067   -0.5046    1.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5742   -0.4246   -2.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7490    1.7059   -3.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0098    4.7230   -3.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9786    3.7332   -3.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7922    1.6235   -3.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -2.1958   -3.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0
 35 33  1  0
 33 32  1  0
 32 24  2  0
 24 23  1  0
 26 27  2  0
 33 34  2  0
 24 25  1  0
  4  3  2  0
  8  9  1  0
  3 35  1  0
  4  5  1  0
 30 31  1  0
  2  1  1  0
 22  8  1  0
  8  6  2  0
 31 25  2  0
  6  7  1  0
  3  2  1  0
 22 35  2  0
 25 26  1  0
 28 29  1  0
 27 28  1  0
 10 20  1  0
 20 18  1  0
 18 16  1  0
 16 12  1  0
 12 11  1  0
 11 10  1  0
 16 17  1  0
 18 19  1  0
 20 21  1  0
 28 30  2  0
 13 15  1  0
  6  4  1  0
 13 14  2  0
 12 13  1  0
 10  9  1  0
 26 50  1  0
 27 51  1  0
 30 53  1  0
 31 54  1  0
 29 52  1  0
  7 40  1  0
 32 55  1  0
  5 39  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
 10 41  1  1
 16 44  1  6
 17 45  1  0
 18 46  1  1
 19 47  1  0
 20 48  1  6
 21 49  1  0
 12 42  1  1
 15 43  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       0.831  -5.791  -2.882  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.245  -5.405  -1.634  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.500  -4.085  -1.369  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.557  -3.814  -0.494  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.295  -4.827   0.060  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.881  -2.508  -0.151  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.919  -2.266   0.710  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.128  -1.454  -0.656  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.504  -0.173  -0.349  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.678   0.388   0.685  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.196   1.357   0.111  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.045   1.986   1.076  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.938   2.954   0.315  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.591   3.974  -0.264  0.00  0.00           O+0
HETATM   15  O   UNK     0      -3.224   2.541   0.264  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.223   2.743   2.120  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.058   3.246   3.170  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.805   1.796   2.748  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.668   2.548   3.617  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.628   1.062   1.691  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.467   0.109   2.365  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.041  -1.714  -1.502  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.670  -0.628  -1.943  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.840  -0.828  -2.649  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.584   0.420  -2.924  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.987   0.468  -2.898  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.663   1.677  -3.091  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.943   2.845  -3.307  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.640   4.006  -3.453  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.556   2.825  -3.343  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.881   1.616  -3.149  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.261  -2.032  -3.056  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.474  -3.230  -2.712  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.828  -4.323  -3.134  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.286  -3.028  -1.854  0.00  0.00           C+0
HETATM   36  H   UNK     0       0.427  -6.771  -3.152  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.917  -5.888  -2.772  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.603  -5.091  -3.692  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.840  -5.655  -0.195  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.292  -3.152   0.904  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.089  -0.391   1.192  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.683   1.231   1.555  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.661   3.176  -0.343  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.292   3.603   1.673  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.440   3.595   3.844  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.298   1.073   3.399  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.394   1.933   3.849  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.299   1.764   1.181  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.807  -0.505   1.675  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.574  -0.425  -2.698  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.749   1.706  -3.059  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.010   4.723  -3.640  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.979   3.733  -3.491  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.792   1.624  -3.153  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.160  -2.196  -3.637  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    1    3                                                       
CONECT    3    4   35    2                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4   39                                                       
CONECT    6    8    7    4                                                  
CONECT    7    6   40                                                       
CONECT    8    9   22    6                                                  
CONECT    9    8   10                                                       
CONECT   10   20   11    9   41                                             
CONECT   11   12   10                                                       
CONECT   12   16   11   13   42                                             
CONECT   13   15   14   12                                                  
CONECT   14   13                                                            
CONECT   15   13   43                                                       
CONECT   16   18   12   17   44                                             
CONECT   17   16   45                                                       
CONECT   18   20   16   19   46                                             
CONECT   19   18   47                                                       
CONECT   20   10   18   21   48                                             
CONECT   21   20   49                                                       
CONECT   22   23    8   35                                                  
CONECT   23   22   24                                                       
CONECT   24   32   23   25                                                  
CONECT   25   24   31   26                                                  
CONECT   26   27   25   50                                                  
CONECT   27   26   28   51                                                  
CONECT   28   29   27   30                                                  
CONECT   29   28   52                                                       
CONECT   30   31   28   53                                                  
CONECT   31   30   25   54                                                  
CONECT   32   33   24   55                                                  
CONECT   33   35   32   34                                                  
CONECT   34   33                                                            
CONECT   35   33    3   22                                                  
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    5                                                            
CONECT   40    7                                                            
CONECT   41   10                                                            
CONECT   42   12                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   17                                                            
CONECT   46   18                                                            
CONECT   47   19                                                            
CONECT   48   20                                                            
CONECT   49   21                                                            
CONECT   50   26                                                            
CONECT   51   27                                                            
CONECT   52   29                                                            
CONECT   53   30                                                            
CONECT   54   31                                                            
CONECT   55   32                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  116    0
END

RDKit          3D

55 58  0  0  0  0  0  0  0  0999 V2000
    0.8311   -5.7914   -2.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2452   -5.4051   -1.6338 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5001   -4.0845   -1.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5573   -3.8137   -0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2954   -4.8272    0.0600 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8811   -2.5076   -0.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9186   -2.2663    0.7097 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284   -1.4543   -0.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5038   -0.1734   -0.3487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6776    0.3883    0.6847 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1957    1.3569    0.1105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0452    1.9858    1.0758 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9376    2.9540    0.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5911    3.9737   -0.2638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2237    2.5409    0.2635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2230    2.7432    2.1201 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0582    3.2460    3.1701 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8054    1.7963    2.7476 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6675    2.5482    3.6173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6276    1.0620    1.6908 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4668    0.1087    2.3651 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0411   -1.7136   -1.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6703   -0.6284   -1.9431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8399   -0.8284   -2.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5838    0.4196   -2.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9866    0.4684   -2.8976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6632    1.6769   -3.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9432    2.8445   -3.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6397    4.0061   -3.4527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5557    2.8252   -3.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8814    1.6163   -3.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2613   -2.0322   -3.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4735   -3.2299   -2.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8280   -4.3226   -3.1337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2861   -3.0282   -1.8537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4270   -6.7714   -3.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165   -5.8881   -2.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6025   -5.0911   -3.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8398   -5.6554   -0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921   -3.1522    0.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0891   -0.3909    1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6829    1.2313    1.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6608    3.1760   -0.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2916    3.6027    1.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4395    3.5952    3.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2980    1.0731    3.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3939    1.9333    3.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2988    1.7637    1.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8067   -0.5046    1.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5742   -0.4246   -2.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7490    1.7059   -3.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0098    4.7230   -3.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9786    3.7332   -3.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7922    1.6235   -3.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -2.1958   -3.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0
 35 33  1  0
 33 32  1  0
 32 24  2  0
 24 23  1  0
 26 27  2  0
 33 34  2  0
 24 25  1  0
  4  3  2  0
  8  9  1  0
  3 35  1  0
  4  5  1  0
 30 31  1  0
  2  1  1  0
 22  8  1  0
  8  6  2  0
 31 25  2  0
  6  7  1  0
  3  2  1  0
 22 35  2  0
 25 26  1  0
 28 29  1  0
 27 28  1  0
 10 20  1  0
 20 18  1  0
 18 16  1  0
 16 12  1  0
 12 11  1  0
 11 10  1  0
 16 17  1  0
 18 19  1  0
 20 21  1  0
 28 30  2  0
 13 15  1  0
  6  4  1  0
 13 14  2  0
 12 13  1  0
 10  9  1  0
 26 50  1  0
 27 51  1  0
 30 53  1  0
 31 54  1  0
 29 52  1  0
  7 40  1  0
 32 55  1  0
  5 39  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
 10 41  1  1
 16 44  1  6
 17 45  1  0
 18 46  1  1
 19 47  1  0
 20 48  1  6
 21 49  1  0
 12 42  1  1
 15 43  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₀O₁₃

Average Mass

492.3890 Da

Monoisotopic Mass

492.09039 Da

IUPAC Name

(2S,3S,4S,5R,6S)-6-{[6,7-dihydroxy-2-(4-hydroxyphenyl)-5-methoxy-4-oxo-4H-chromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-6-{[6,7-dihydroxy-2-(4-hydroxyphenyl)-5-methoxy-4-oxochromen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@@]1([H])O[C@@]([H])(OC2=C(O[H])C(O[H])=C(OC([H])([H])[H])C3=C2OC(=C([H])C3=O)C2=C([H])C([H])=C(O[H])C([H])=C2[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C22H20O13/c1-32-17-11-9(24)6-10(7-2-4-8(23)5-3-7)33-18(11)19(15(28)14(17)27)34-22-16(29)12(25)13(26)20(35-22)21(30)31/h2-6,12-13,16,20,22-23,25-29H,1H3,(H,30,31)/t12-,13-,16+,20-,22+/m0/s1

InChI Key

XWWLMXDERFHTHA-DPOSBGKNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, 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
Aquilaria sinensis	JEOL database	Feng, J., et al, Phytochemistry 72, 242 (2011).

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-8-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-8-O-glucuronides

Alternative Parents

Substituents

Flavonoid-8-o-glucuronide
Flavonoid-8-o-glycoside
5-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
4'-hydroxyflavonoid
7-hydroxyflavonoid
6-hydroxyflavonoid
Phenolic glycoside
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Anisole
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Hydroxy acid
Monosaccharide
Heteroaromatic compound
Vinylogous ester
Secondary alcohol
Monocarboxylic acid or derivatives
Acetal
Polyol
Oxacycle
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Carboxylic acid
Organic oxygen compound
Alcohol
Organic oxide
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
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	1.47	ALOGPS
logP	-0.35	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	2.48	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	212.67 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.37 m³·mol⁻¹	ChemAxon
Polarizability	45.66 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

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

51034837

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Feng J, Yang XW, Wang RF: Bio-assay guided isolation and identification of alpha-glucosidase inhibitors from the leaves of Aquilaria sinensis. Phytochemistry. 2011 Feb;72(2-3):242-7. doi: 10.1016/j.phytochem.2010.11.025. Epub 2011 Jan 6. [PubMed:21215978 ]
Feng, J., et al. (2011). Feng, J., et al, Phytochemistry 72, 242 (2011).. Phytochem..

Showing NP-Card for aquilarisin (NP0040172)

MOL for NP0040172 (aquilarisin)

3D MOL for NP0040172 (aquilarisin)

3D SDF for NP0040172 (aquilarisin)

3D-SDF for NP0040172 (aquilarisin)

PDB for NP0040172 (aquilarisin)

3D PDB for NP0040172 (aquilarisin)

SMILES for NP0040172 (aquilarisin)

INCHI for NP0040172 (aquilarisin)

Structure for NP0040172 (aquilarisin)

3D Structure for NP0040172 (aquilarisin)