NP-MRD: Showing NP-Card for 3-O-methyl-4'-(3''-O-acetyl)-alpha-L-rhamnopyranosylellagic acid (NP0033791)

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Record Information

Version

2.0

Created at

2021-06-20 17:42:33 UTC

Updated at

2021-06-30 00:03:47 UTC

NP-MRD ID

NP0033791

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-O-methyl-4'-(3''-O-acetyl)-alpha-L-rhamnopyranosylellagic acid

Provided By

JEOL Database JEOL Logo

Description

2-(3-O-Acetyl-alpha-L-rhamnopyranosyloxy)-3,7-dihydroxy-8-methoxy[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. 3-O-methyl-4'-(3''-O-acetyl)-alpha-L-rhamnopyranosylellagic acid is found in C. glabrum and Caryocar villosum. 3-O-methyl-4'-(3''-O-acetyl)-alpha-L-rhamnopyranosylellagic acid was first documented in 2008 (Magid, A. A., et al.). Based on a literature review very few articles have been published on 2-(3-O-Acetyl-alpha-L-rhamnopyranosyloxy)-3,7-dihydroxy-8-methoxy[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119423D          

 56 60  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202119423D          

 56 60  0  0  0  0            999 V2000
   -6.3404   -1.8060    2.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3571   -0.5683    1.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7354   -0.1063    2.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9902    1.0616    2.3429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7288   -1.0848    2.0384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5090   -2.4543    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1953   -2.8691    1.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1242   -1.9097    1.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1235   -1.1485    1.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9197   -1.4245    3.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4280   -1.8333    2.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0961   -5.1483    1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7909   -6.1878    0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4423   -2.8629    0.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7576    0.0208    1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012    3.3754    1.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1925    4.2774    0.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8119    5.3513    0.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5192    4.3585    2.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8372    3.2672   -1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9255    4.3096   -2.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1454    2.0416   -0.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8578    0.7969   -4.9999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6137    2.0920   -4.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1344    0.3816   -4.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3275   -0.1817   -0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8265    1.0428   -0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4822    1.3950    2.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0  0  0  0
 34 35  1  0  0  0  0
 22 23  1  0  0  0  0
 34 33  1  0  0  0  0
 35 36  1  0  0  0  0
 30 31  1  0  0  0  0
 31 33  1  0  0  0  0
 16 15  1  0  0  0  0
 36 11  2  0  0  0  0
 20 22  1  0  0  0  0
 11 12  1  0  0  0  0
  6  7  1  0  0  0  0
 12 14  2  0  0  0  0
 22 27  1  0  0  0  0
 14 29  1  0  0  0  0
 34  3  2  0  0  0  0
 29 30  2  0  0  0  0
 30 36  1  0  0  0  0
 27 16  1  0  0  0  0
  4  5  1  0  0  0  0
  3  4  1  0  0  0  0
  3  2  1  0  0  0  0
  4  6  2  0  0  0  0
  2  1  1  0  0  0  0
 35  7  2  0  0  0  0
  8  9  2  0  0  0  0
 16 17  1  0  0  0  0
 31 32  2  0  0  0  0
 17 18  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 18 20  1  0  0  0  0
 23 24  1  0  0  0  0
  7  8  1  0  0  0  0
 24 26  2  0  0  0  0
  8 10  1  0  0  0  0
 24 25  1  0  0  0  0
 20 21  1  0  0  0  0
 18 19  1  0  0  0  0
 27 28  1  0  0  0  0
 28 55  1  0  0  0  0
 21 49  1  0  0  0  0
 20 48  1  6  0  0  0
 16 43  1  1  0  0  0
 19 45  1  0  0  0  0
 19 46  1  0  0  0  0
 19 47  1  0  0  0  0
 18 44  1  1  0  0  0
 27 54  1  1  0  0  0
 22 50  1  1  0  0  0
  6 41  1  0  0  0  0
 29 56  1  0  0  0  0
  5 40  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
 13 42  1  0  0  0  0
 25 51  1  0  0  0  0
 25 52  1  0  0  0  0
 25 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033791

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C3C(OC(=O)C4=C([H])C(O[C@]5([H])O[C@@]([H])(C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]5([H])O[H])=C(O[H])C(OC2=O)=C34)=C1OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H20O13/c1-6-14(26)20(33-7(2)24)16(28)23(32-6)34-11-5-9-12-13-8(21(29)35-18(12)15(11)27)4-10(25)17(31-3)19(13)36-22(9)30/h4-6,14,16,20,23,25-28H,1-3H3/t6-,14-,16+,20+,23-/m0/s1

> <INCHI_KEY>
PSQAVUUHZLODEY-YAWJASLASA-N

> <FORMULA>
C23H20O13

> <MOLECULAR_WEIGHT>
504.4

> <EXACT_MASS>
504.090390704

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
47.162136133056705

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5S,6S)-2-({7,13-dihydroxy-14-methoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)-3,5-dihydroxy-6-methyloxan-4-yl acetate

> <ALOGPS_LOGP>
1.55

> <JCHEM_LOGP>
1.0317837576666657

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.58237869079705

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.170942582282028

> <JCHEM_PKA_STRONGEST_BASIC>
-3.623359768027975

> <JCHEM_POLAR_SURFACE_AREA>
187.51

> <JCHEM_REFRACTIVITY>
114.84209999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5S,6S)-2-({7,13-dihydroxy-14-methoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)-3,5-dihydroxy-6-methyloxan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
   -6.3404   -1.8060    2.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9046   -3.1351    1.9541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5731   -3.3593    1.7317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2724   -4.7007    1.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2726   -5.6361    1.4169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9759   -5.1375    1.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9317   -4.2123    1.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5413   -4.6604    0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2718   -5.8288    0.7099 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4510   -3.6792    0.9955 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1778   -2.3196    1.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2513   -1.4247    1.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5085   -1.8993    1.0382 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0167   -0.0737    1.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9311    0.9401    1.5658 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1278    0.8340    0.7934 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9507    2.0122    1.0014 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3008    3.2329    0.6153 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2548    4.3776    0.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9305    3.2294   -0.8783 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1584    4.3905   -1.2033 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1311    1.9643   -1.2155 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9278    1.9378   -2.6496 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9688    1.0730   -3.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8945    1.0933   -4.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2611    0.3829   -2.3606 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8914    0.7179   -0.7301 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1501    0.6073   -1.4295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2922    0.3440    1.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -0.5683    1.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7354   -0.1063    2.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9902    1.0616    2.3429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7288   -1.0848    2.0384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5090   -2.4543    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1953   -2.8691    1.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1242   -1.9097    1.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1235   -1.1485    1.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9197   -1.4245    3.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4280   -1.8333    2.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0961   -5.1483    1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7909   -6.1878    0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4423   -2.8629    0.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7576    0.0208    1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012    3.3754    1.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1925    4.2774    0.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8119    5.3513    0.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5192    4.3585    2.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8372    3.2672   -1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9255    4.3096   -2.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1454    2.0416   -0.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8578    0.7969   -4.9999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6137    2.0920   -4.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1344    0.3816   -4.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3275   -0.1817   -0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8265    1.0428   -0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4822    1.3950    2.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 34 35  1  0
 22 23  1  0
 34 33  1  0
 35 36  1  0
 30 31  1  0
 31 33  1  0
 16 15  1  0
 36 11  2  0
 20 22  1  0
 11 12  1  0
  6  7  1  0
 12 14  2  0
 22 27  1  0
 14 29  1  0
 34  3  2  0
 29 30  2  0
 30 36  1  0
 27 16  1  0
  4  5  1  0
  3  4  1  0
  3  2  1  0
  4  6  2  0
  2  1  1  0
 35  7  2  0
  8  9  2  0
 16 17  1  0
 31 32  2  0
 17 18  1  0
 12 13  1  0
 14 15  1  0
 18 20  1  0
 23 24  1  0
  7  8  1  0
 24 26  2  0
  8 10  1  0
 24 25  1  0
 20 21  1  0
 18 19  1  0
 27 28  1  0
 28 55  1  0
 21 49  1  0
 20 48  1  6
 16 43  1  1
 19 45  1  0
 19 46  1  0
 19 47  1  0
 18 44  1  1
 27 54  1  1
 22 50  1  1
  6 41  1  0
 29 56  1  0
  5 40  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
 13 42  1  0
 25 51  1  0
 25 52  1  0
 25 53  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      -6.340  -1.806   2.208  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.905  -3.135   1.954  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.573  -3.359   1.732  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.272  -4.701   1.449  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.273  -5.636   1.417  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.976  -5.138   1.194  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.932  -4.212   1.219  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.541  -4.660   0.952  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.272  -5.829   0.710  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.451  -3.679   0.996  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.178  -2.320   1.271  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.251  -1.425   1.277  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.509  -1.899   1.038  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.017  -0.074   1.535  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.931   0.940   1.566  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.128   0.834   0.793  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.951   2.012   1.001  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.301   3.233   0.615  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.255   4.378   0.944  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.930   3.229  -0.878  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.158   4.391  -1.203  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.131   1.964  -1.216  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.928   1.938  -2.650  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.969   1.073  -3.082  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.895   1.093  -4.577  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.261   0.383  -2.361  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.891   0.718  -0.730  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.150   0.607  -1.430  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.292   0.344   1.818  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.357  -0.568   1.804  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.735  -0.106   2.084  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.990   1.062   2.343  0.00  0.00           O+0
HETATM   33  O   UNK     0      -3.729  -1.085   2.038  0.00  0.00           O+0
HETATM   34  C   UNK     0      -3.509  -2.454   1.753  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.195  -2.869   1.498  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.124  -1.910   1.525  0.00  0.00           C+0
HETATM   37  H   UNK     0      -6.123  -1.149   1.360  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.920  -1.425   3.143  0.00  0.00           H+0
HETATM   39  H   UNK     0      -7.428  -1.833   2.328  0.00  0.00           H+0
HETATM   40  H   UNK     0      -6.096  -5.148   1.617  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.791  -6.188   0.979  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.442  -2.863   0.889  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.758   0.021   1.163  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.401   3.375   1.228  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.192   4.277   0.386  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.812   5.351   0.715  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.519   4.359   2.007  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.837   3.267  -1.495  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.926   4.310  -2.147  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.145   2.042  -0.737  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.858   0.797  -5.000  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.614   2.092  -4.920  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.134   0.382  -4.912  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.328  -0.182  -0.984  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.827   1.043  -0.875  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.482   1.395   2.035  0.00  0.00           H+0
CONECT    1    2   37   38   39                                             
CONECT    2    3    1                                                       
CONECT    3   34    4    2                                                  
CONECT    4    5    3    6                                                  
CONECT    5    4   40                                                       
CONECT    6    7    4   41                                                  
CONECT    7    6   35    8                                                  
CONECT    8    9    7   10                                                  
CONECT    9    8                                                            
CONECT   10   11    8                                                       
CONECT   11   10   36   12                                                  
CONECT   12   11   14   13                                                  
CONECT   13   12   42                                                       
CONECT   14   12   29   15                                                  
CONECT   15   16   14                                                       
CONECT   16   15   27   17   43                                             
CONECT   17   16   18                                                       
CONECT   18   17   20   19   44                                             
CONECT   19   18   45   46   47                                             
CONECT   20   22   18   21   48                                             
CONECT   21   20   49                                                       
CONECT   22   23   20   27   50                                             
CONECT   23   22   24                                                       
CONECT   24   23   26   25                                                  
CONECT   25   24   51   52   53                                             
CONECT   26   24                                                            
CONECT   27   22   16   28   54                                             
CONECT   28   27   55                                                       
CONECT   29   14   30   56                                                  
CONECT   30   31   29   36                                                  
CONECT   31   30   33   32                                                  
CONECT   32   31                                                            
CONECT   33   34   31                                                       
CONECT   34   35   33    3                                                  
CONECT   35   34   36    7                                                  
CONECT   36   35   11   30                                                  
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    5                                                            
CONECT   41    6                                                            
CONECT   42   13                                                            
CONECT   43   16                                                            
CONECT   44   18                                                            
CONECT   45   19                                                            
CONECT   46   19                                                            
CONECT   47   19                                                            
CONECT   48   20                                                            
CONECT   49   21                                                            
CONECT   50   22                                                            
CONECT   51   25                                                            
CONECT   52   25                                                            
CONECT   53   25                                                            
CONECT   54   27                                                            
CONECT   55   28                                                            
CONECT   56   29                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  120    0
END

RDKit          3D

56 60  0  0  0  0  0  0  0  0999 V2000
   -6.3404   -1.8060    2.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9046   -3.1351    1.9541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5731   -3.3593    1.7317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2724   -4.7007    1.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2726   -5.6361    1.4169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9759   -5.1375    1.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9317   -4.2123    1.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5413   -4.6604    0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2718   -5.8288    0.7099 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4510   -3.6792    0.9955 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1778   -2.3196    1.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2513   -1.4247    1.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5085   -1.8993    1.0382 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0167   -0.0737    1.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9311    0.9401    1.5658 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1278    0.8340    0.7934 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9507    2.0122    1.0014 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3008    3.2329    0.6153 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2548    4.3776    0.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9305    3.2294   -0.8783 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1584    4.3905   -1.2033 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1311    1.9643   -1.2155 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9278    1.9378   -2.6496 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9688    1.0730   -3.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8945    1.0933   -4.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2611    0.3829   -2.3606 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8914    0.7179   -0.7301 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1501    0.6073   -1.4295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2922    0.3440    1.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -0.5683    1.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7354   -0.1063    2.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9902    1.0616    2.3429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7288   -1.0848    2.0384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5090   -2.4543    1.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1953   -2.8691    1.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1242   -1.9097    1.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1235   -1.1485    1.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9197   -1.4245    3.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4280   -1.8333    2.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0961   -5.1483    1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7909   -6.1878    0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4423   -2.8629    0.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7576    0.0208    1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012    3.3754    1.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1925    4.2774    0.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8119    5.3513    0.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5192    4.3585    2.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8372    3.2672   -1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9255    4.3096   -2.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1454    2.0416   -0.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8578    0.7969   -4.9999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6137    2.0920   -4.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1344    0.3816   -4.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3275   -0.1817   -0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8265    1.0428   -0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4822    1.3950    2.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 34 35  1  0
 22 23  1  0
 34 33  1  0
 35 36  1  0
 30 31  1  0
 31 33  1  0
 16 15  1  0
 36 11  2  0
 20 22  1  0
 11 12  1  0
  6  7  1  0
 12 14  2  0
 22 27  1  0
 14 29  1  0
 34  3  2  0
 29 30  2  0
 30 36  1  0
 27 16  1  0
  4  5  1  0
  3  4  1  0
  3  2  1  0
  4  6  2  0
  2  1  1  0
 35  7  2  0
  8  9  2  0
 16 17  1  0
 31 32  2  0
 17 18  1  0
 12 13  1  0
 14 15  1  0
 18 20  1  0
 23 24  1  0
  7  8  1  0
 24 26  2  0
  8 10  1  0
 24 25  1  0
 20 21  1  0
 18 19  1  0
 27 28  1  0
 28 55  1  0
 21 49  1  0
 20 48  1  6
 16 43  1  1
 19 45  1  0
 19 46  1  0
 19 47  1  0
 18 44  1  1
 27 54  1  1
 22 50  1  1
  6 41  1  0
 29 56  1  0
  5 40  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
 13 42  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
M  END

View in JSmol

Synonyms

Value	Source
2-(3-O-Acetyl-a-L-rhamnopyranosyloxy)-3,7-dihydroxy-8-methoxy[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione	Generator
2-(3-O-Acetyl-α-L-rhamnopyranosyloxy)-3,7-dihydroxy-8-methoxy[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione	Generator

Chemical Formula

C₂₃H₂₀O₁₃

Average Mass

504.4000 Da

Monoisotopic Mass

504.09039 Da

IUPAC Name

(2S,3R,4R,5S,6S)-2-({7,13-dihydroxy-14-methoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)-3,5-dihydroxy-6-methyloxan-4-yl acetate

Traditional Name

(2S,3R,4R,5S,6S)-2-({7,13-dihydroxy-14-methoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)-3,5-dihydroxy-6-methyloxan-4-yl acetate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C3C(OC(=O)C4=C([H])C(O[C@]5([H])O[C@@]([H])(C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]5([H])O[H])=C(O[H])C(OC2=O)=C34)=C1OC([H])([H])[H]

InChI Identifier

InChI=1S/C23H20O13/c1-6-14(26)20(33-7(2)24)16(28)23(32-6)34-11-5-9-12-13-8(21(29)35-18(12)15(11)27)4-10(25)17(31-3)19(13)36-22(9)30/h4-6,14,16,20,23,25-28H,1-3H3/t6-,14-,16+,20+,23-/m0/s1

InChI Key

PSQAVUUHZLODEY-YAWJASLASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Caryocar glabrum	JEOL database	Magid, A. A., et al, J. Nat. Prod. 71, 914 (2008)
Caryocar villosum	JEOL database	Magid, A. A., et al, J. Nat. Prod. 71, 914 (2008)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Ellagic_acid
Phenolic glycoside
Hexose monosaccharide
Coumarin
Glycosyl compound
Isocoumarin
O-glycosyl compound
Benzopyran
2-benzopyran
1-benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Monosaccharide
Oxane
Heteroaromatic compound
Lactone
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Oxacycle
Ether
Organoheterocyclic compound
Carbonyl group
Organic oxide
Alcohol
Organic oxygen compound
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	1.55	ALOGPS
logP	1.03	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.17	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	187.51 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	114.84 m³·mol⁻¹	ChemAxon
Polarizability	47.16 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

24879067

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Magid, A. A., et al. (2008). Magid, A. A., et al, J. Nat. Prod. 71, 914 (2008) . J. Nat. Prod..

Showing NP-Card for 3-O-methyl-4'-(3''-O-acetyl)-alpha-L-rhamnopyranosylellagic acid (NP0033791)

MOL for NP0033791 (3-O-methyl-4'-(3''-O-acetyl)-alpha-L-rhamnopyranosylellagic acid)

3D MOL for NP0033791 (3-O-methyl-4'-(3''-O-acetyl)-alpha-L-rhamnopyranosylellagic acid)

3D SDF for NP0033791 (3-O-methyl-4'-(3''-O-acetyl)-alpha-L-rhamnopyranosylellagic acid)

3D-SDF for NP0033791 (3-O-methyl-4'-(3''-O-acetyl)-alpha-L-rhamnopyranosylellagic acid)

PDB for NP0033791 (3-O-methyl-4'-(3''-O-acetyl)-alpha-L-rhamnopyranosylellagic acid)

3D PDB for NP0033791 (3-O-methyl-4'-(3''-O-acetyl)-alpha-L-rhamnopyranosylellagic acid)

SMILES for NP0033791 (3-O-methyl-4'-(3''-O-acetyl)-alpha-L-rhamnopyranosylellagic acid)

INCHI for NP0033791 (3-O-methyl-4'-(3''-O-acetyl)-alpha-L-rhamnopyranosylellagic acid)

Structure for NP0033791 (3-O-methyl-4'-(3''-O-acetyl)-alpha-L-rhamnopyranosylellagic acid)

3D Structure for NP0033791 (3-O-methyl-4'-(3''-O-acetyl)-alpha-L-rhamnopyranosylellagic acid)