NP-MRD: Showing NP-Card for (2r,3s,4r,5r,6s)-2-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate (NP0232741)

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Record Information

Version

2.0

Created at

2022-09-06 14:04:39 UTC

Updated at

2022-09-06 14:04:39 UTC

NP-MRD ID

NP0232741

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4r,5r,6s)-2-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate

Description

Trilobatin 2''-acetate belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. (2r,3s,4r,5r,6s)-2-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate is found in Lithocarpus pachyphyllus. Based on a literature review very few articles have been published on Trilobatin 2''-acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062216042D          

 34 36  0  0  1  0            999 V2000
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 17 23  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  8 26  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
  5 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
   -3.8553    4.5815    0.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8313    3.1477    0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4704    2.7945    1.9569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2103    2.1956   -0.0921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2296    0.7992    0.1632 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2362    0.0846   -0.7003 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6128   -0.9648   -0.0395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2616   -1.1098    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3085   -0.1935   -0.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0358   -0.4039    0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9678    0.5694   -0.2496 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4937   -1.5169    0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9291   -1.6835    1.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3425   -2.6883    1.7239 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9059   -0.6415    0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2886   -1.1367    1.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2565   -0.1104    0.7023 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5759    0.9254    1.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4898    1.8890    1.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0528    1.7776   -0.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9672    2.7441   -0.5119 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7203    0.7404   -0.9339 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8165   -0.2248   -0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -2.4410    1.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8939   -3.5763    1.8726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8163   -2.2259    0.8980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7690   -0.4223   -1.8709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8980   -1.1703   -1.7414 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7401   -2.4536   -0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8114   -3.3074   -1.5598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0019   -0.3076   -1.2318 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2466    0.6817   -2.1966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6205    0.3217    0.0804 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9049   -0.6202    1.0807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5246    4.7487   -0.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2405    5.1801    1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9051    4.9506    0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8777    0.6916    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4821    0.8293   -1.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5738    0.7222   -0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6800    1.4009   -0.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6995    0.3397    1.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9403   -0.5198   -0.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3375   -1.2526    2.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4859   -2.1251    0.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1567    1.0436    2.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7554    2.7164    1.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9492    2.6192   -0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1614    0.6522   -1.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5479   -1.0495   -1.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7056   -3.9401    2.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4971   -2.9961    1.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1914   -1.4804   -2.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7293   -2.9868   -1.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4900   -2.3441    0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4242   -3.8804   -0.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9140   -0.9134   -1.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9990    1.5784   -1.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3570    1.1587    0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6653   -1.1970    0.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5 33  1  0
 33 34  1  0
 33 31  1  0
 31 32  1  0
 31 28  1  0
 28 29  1  0
 29 30  1  0
 28 27  1  0
 27  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 12 24  1  0
 24 25  1  0
 24 26  2  0
  6  5  1  0
 26  8  1  0
 23 17  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  5 38  1  1
 33 59  1  1
 34 60  1  0
 31 57  1  1
 32 58  1  0
 28 53  1  6
 29 54  1  0
 29 55  1  0
 30 56  1  0
  6 39  1  6
  9 40  1  0
 11 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 18 46  1  0
 19 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 25 51  1  0
 26 52  1  0
M  END


  Mrv1652309062216042D          

 34 36  0  0  1  0            999 V2000
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 17 23  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  8 26  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
  5 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0232741

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@@H]1OC1=CC(O)=C(C(=O)CCC2=CC=C(O)C=C2)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O11/c1-11(25)32-22-21(31)20(30)18(10-24)34-23(22)33-14-8-16(28)19(17(29)9-14)15(27)7-4-12-2-5-13(26)6-3-12/h2-3,5-6,8-9,18,20-24,26,28-31H,4,7,10H2,1H3/t18-,20-,21+,22-,23-/m0/s1

> <INCHI_KEY>
QIEAJYJXGQAYRU-LCNLMQJVSA-N

> <FORMULA>
C23H26O11

> <MOLECULAR_WEIGHT>
478.45

> <EXACT_MASS>
478.147511657

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
47.52147043838549

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,4R,5R,6S)-2-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate

> <JCHEM_LOGP>
2.068597849666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.499237396591438

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.749166573527072

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092989606627

> <JCHEM_POLAR_SURFACE_AREA>
183.21

> <JCHEM_REFRACTIVITY>
115.0032

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R,5R,6S)-2-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      18.672  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.672  -7.700   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      20.005  -6.930   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      18.672  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.005 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.005 -11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.339 -12.320   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.339 -13.860   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.005 -14.630   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      20.005 -16.170   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      18.672 -13.860   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.672 -12.320   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      16.004  -9.240   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   33                                                  
CONECT    6    5    7   27                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   24                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   17                                                       
CONECT   24   12   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    8                                                       
CONECT   27    6   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    5   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
Trilobatin 2''-acetic acid	Generator

Chemical Formula

C₂₃H₂₆O₁₁

Average Mass

478.4500 Da

Monoisotopic Mass

478.14751 Da

IUPAC Name

(2R,3S,4R,5R,6S)-2-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate

Traditional Name

(2R,3S,4R,5R,6S)-2-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@@H]1OC1=CC(O)=C(C(=O)CCC2=CC=C(O)C=C2)C(O)=C1

InChI Identifier

InChI=1S/C23H26O11/c1-11(25)32-22-21(31)20(30)18(10-24)34-23(22)33-14-8-16(28)19(17(29)9-14)15(27)7-4-12-2-5-13(26)6-3-12/h2-3,5-6,8-9,18,20-24,26,28-31H,4,7,10H2,1H3/t18-,20-,21+,22-,23-/m0/s1

InChI Key

QIEAJYJXGQAYRU-LCNLMQJVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lithocarpus pachyphyllus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid o-glycoside
2'-hydroxy-dihydrochalcone
Phenolic glycoside
Cinnamylphenol
Linear 1,3-diarylpropanoid
Alkyl-phenylketone
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Butyrophenone
Phenylketone
Phenoxy compound
Aryl alkyl ketone
Aryl ketone
Resorcinol
Phenol ether
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.07	ChemAxon
pKa (Strongest Acidic)	8.75	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	115 m³·mol⁻¹	ChemAxon
Polarizability	47.52 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

133562820

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,4r,5r,6s)-2-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate (NP0232741)

MOL for NP0232741 ((2r,3s,4r,5r,6s)-2-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)

3D MOL for NP0232741 ((2r,3s,4r,5r,6s)-2-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)

3D SDF for NP0232741 ((2r,3s,4r,5r,6s)-2-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)

3D-SDF for NP0232741 ((2r,3s,4r,5r,6s)-2-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)

PDB for NP0232741 ((2r,3s,4r,5r,6s)-2-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)

3D PDB for NP0232741 ((2r,3s,4r,5r,6s)-2-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)

SMILES for NP0232741 ((2r,3s,4r,5r,6s)-2-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)

INCHI for NP0232741 ((2r,3s,4r,5r,6s)-2-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)

Structure for NP0232741 ((2r,3s,4r,5r,6s)-2-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)

3D Structure for NP0232741 ((2r,3s,4r,5r,6s)-2-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl acetate)