NP-MRD: Showing NP-Card for 3-[3-hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid (NP0152586)

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Record Information

Version

2.0

Created at

2022-09-02 09:06:02 UTC

Updated at

2022-09-02 09:06:02 UTC

NP-MRD ID

NP0152586

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[3-hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid

Description

3-[3-Hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Based on a literature review very few articles have been published on 3-[3-hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022211062D          

 31 33  0  0  0  0            999 V2000
   -0.1712    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  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
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 16 29  2  0  0  0  0
  7 29  1  0  0  0  0
 29 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
   -3.9204   -3.4833   -0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2428   -2.0468   -0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5989   -1.2663   -1.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3995   -2.0765    0.6473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1797   -1.3675    0.6554 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6551   -0.0687    0.9514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6999    0.8918    0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7596    2.2771    0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6833    3.0332    0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5815    2.4462   -0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5435    3.2667   -0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4942    4.7064   -0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5016    4.8138    1.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5540    3.7980    2.0429 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4507    6.0421    1.9291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5510    1.0835   -0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5099    0.3939   -0.9265 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6032   -0.1481   -0.2004 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6798   -1.5364   -0.3986 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5485   -2.1010    0.5130 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7448   -3.5803    0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -3.7336   -1.0544 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9538   -1.4907    0.4317 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0719   -0.6166    1.4973 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9554   -0.6990   -0.8833 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2230   -0.1173   -0.9989 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9363    0.4232   -0.6397 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5335    1.1699    0.4058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6190    0.2702    0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8673   -1.1898   -0.0060 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7798   -1.7297   -1.2754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3876   -3.6056   -1.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8774   -4.0337   -0.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3715   -3.9271    0.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7848   -0.6619   -1.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0166   -1.9656   -2.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4368   -0.5362   -1.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1596   -2.0067    1.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0640   -1.9469    1.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6276    2.7533    1.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6928    4.0986    0.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628    2.8513   -0.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6343    3.1722   -1.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3453    5.2643   -0.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4269    5.1893   -0.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6457    6.8960    1.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4225    0.0901    0.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1169   -1.9970    1.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5213   -3.9377    0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8406   -4.1828    0.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2820   -3.7250   -1.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7377   -2.2522    0.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7394   -0.8929    2.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6899   -1.3145   -1.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7026   -0.1219   -0.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8460    1.0090   -1.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8341    1.3196    1.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0641   -1.6876    0.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1200   -1.2127   -1.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 16 29  2  0
 29 30  1  0
 30 31  1  0
 30  5  1  0
 29  7  1  0
 27 18  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  1
  8 40  1  0
  9 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 12 45  1  0
 15 46  1  0
 18 47  1  1
 20 48  1  1
 21 49  1  0
 21 50  1  0
 22 51  1  0
 23 52  1  6
 24 53  1  0
 25 54  1  6
 26 55  1  0
 27 56  1  6
 28 57  1  0
 30 58  1  1
 31 59  1  0
M  END


  Mrv1652309022211062D          

 31 33  0  0  0  0            999 V2000
   -0.1712    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  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
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 16 29  2  0  0  0  0
  7 29  1  0  0  0  0
 29 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0152586

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)C1OC2=CC=C(CCC(O)=O)C(OC3OC(CO)C(O)C(O)C3O)=C2C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O11/c1-20(2,28)18-14(25)12-9(29-18)5-3-8(4-6-11(22)23)17(12)31-19-16(27)15(26)13(24)10(7-21)30-19/h3,5,10,13-16,18-19,21,24-28H,4,6-7H2,1-2H3,(H,22,23)

> <INCHI_KEY>
DAVXSVGAHCHFQB-UHFFFAOYSA-N

> <FORMULA>
C20H28O11

> <MOLECULAR_WEIGHT>
444.433

> <EXACT_MASS>
444.163161722

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
43.86377629313881

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[3-hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid

> <ALOGPS_LOGP>
-0.92

> <JCHEM_LOGP>
-1.4860328000000007

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.113354825882748

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4659234170491247

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923461162027

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
102.09170000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[3-hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.320   0.237   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.860  -1.303   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.320  -2.843   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.925  -0.533   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.259   0.237   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.591  -4.383   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.259  -2.843   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.259  -7.463   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.591  -9.003   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.924  -7.463   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   29                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   18   28                                                  
CONECT   28   27                                                            
CONECT   29   16    7   30                                                  
CONECT   30   29    5   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
3-[3-Hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoate	Generator

Chemical Formula

C₂₀H₂₈O₁₁

Average Mass

444.4330 Da

Monoisotopic Mass

444.16316 Da

IUPAC Name

3-[3-hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid

Traditional Name

3-[3-hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)(O)C1OC2=CC=C(CCC(O)=O)C(OC3OC(CO)C(O)C(O)C3O)=C2C1O

InChI Identifier

InChI=1S/C20H28O11/c1-20(2,28)18-14(25)12-9(29-18)5-3-8(4-6-11(22)23)17(12)31-19-16(27)15(26)13(24)10(7-21)30-19/h3,5,10,13-16,18-19,21,24-28H,4,6-7H2,1-2H3,(H,22,23)

InChI Key

DAVXSVGAHCHFQB-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
O-glycosyl compound
Coumaran
Alkyl aryl ether
Monosaccharide
Oxane
Benzenoid
Tertiary alcohol
Secondary alcohol
Polyol
Acetal
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Primary alcohol
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
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	-0.92	ALOGPS
logP	-1.5	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	102.09 m³·mol⁻¹	ChemAxon
Polarizability	43.86 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

72812508

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[3-hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid (NP0152586)

MOL for NP0152586 (3-[3-hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid)

3D MOL for NP0152586 (3-[3-hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid)

3D SDF for NP0152586 (3-[3-hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid)

3D-SDF for NP0152586 (3-[3-hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid)

PDB for NP0152586 (3-[3-hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid)

3D PDB for NP0152586 (3-[3-hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid)

SMILES for NP0152586 (3-[3-hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid)

INCHI for NP0152586 (3-[3-hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid)

Structure for NP0152586 (3-[3-hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid)

3D Structure for NP0152586 (3-[3-hydroxy-2-(2-hydroxypropan-2-yl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]propanoic acid)