NP-MRD: Showing NP-Card for (4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate (NP0216004)

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Record Information

Version

2.0

Created at

2022-09-05 15:48:36 UTC

Updated at

2022-09-05 15:48:36 UTC

NP-MRD ID

NP0216004

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate

Description

(4-{[3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate 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. (4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate is found in Sicana odorifera. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose (4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231520212D          

 31 32  0  0  0  0            999 V2000
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 C   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
    7.4467   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717   -2.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -3.3000    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 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
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  2  0  0  0  0
 10 27  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  END

     RDKit          3D

 59 60  0  0  0  0  0  0  0  0999 V2000
    8.6691   -1.4052    1.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3382   -0.7487    1.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8806   -0.3429    2.4970 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5831   -0.5829    0.2741 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3223    0.0096    0.2200 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3298   -1.0077   -0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6860   -2.1823   -0.5502 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9861   -0.6994   -0.4170 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0878   -1.6951   -0.8778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7090   -1.2102   -0.9837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1845   -0.6344   -2.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1224   -0.2131   -2.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9677   -0.3274   -1.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2600    0.1034   -1.0564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2284    0.0641   -0.0561 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3129   -0.7101   -0.4833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3678   -0.5992    0.4104 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4627   -1.5601    0.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0145   -2.8740    0.0564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9883    0.8008    0.3805 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2684    0.7963   -0.1176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0372    1.6543   -0.4639 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4732    2.9552   -0.5584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6758    1.5175    0.1657 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7928    1.7317    1.5295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4261   -0.8992    0.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1041   -1.3381    0.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2652    1.1761   -0.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2271    2.2649   -0.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5441    0.6374   -2.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9848    1.7260   -0.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6813   -2.1434    0.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4162   -0.6023    1.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9311   -1.9931    2.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9570    0.3540    1.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4362   -2.0049   -1.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1423   -2.6028   -0.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317   -0.5399   -2.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5153    0.2328   -3.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8995   -0.3816    0.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0215   -0.8719    1.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8731   -1.3477   -0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3146   -1.4265    0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1324   -2.8708    0.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9758    1.2155    1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9600    0.8343    0.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9829    1.1446   -1.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5128    3.2592   -1.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9571    2.2308   -0.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8271    2.6656    1.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0340   -1.0183    0.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429   -1.7781    1.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0856    2.2082   -1.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7598    3.2837   -0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5585    2.1775    0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1994    1.3343   -2.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6028    0.4897   -2.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0300   -0.3736   -2.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8355    2.1175    0.1545 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  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 13 26  1  0
 26 27  2  0
  5 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
 27 10  1  0
 24 15  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  1
  9 36  1  0
  9 37  1  0
 11 38  1  0
 12 39  1  0
 15 40  1  1
 17 41  1  1
 18 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  1
 21 46  1  0
 22 47  1  6
 23 48  1  0
 24 49  1  6
 25 50  1  0
 26 51  1  0
 27 52  1  0
 29 53  1  0
 29 54  1  0
 29 55  1  0
 30 56  1  0
 30 57  1  0
 30 58  1  0
 31 59  1  0
M  END


  Mrv1533004231520212D          

 31 32  0  0  0  0            999 V2000
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 C   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
    7.4467   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717   -2.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -3.3000    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 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
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  2  0  0  0  0
 10 27  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0216004

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC(C(=O)OCC1=CC=C(OC2OC(CO)C(O)C(O)C2O)C=C1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O11/c1-10(22)29-17(20(2,3)27)18(26)28-9-11-4-6-12(7-5-11)30-19-16(25)15(24)14(23)13(8-21)31-19/h4-7,13-17,19,21,23-25,27H,8-9H2,1-3H3

> <INCHI_KEY>
RXXZTHWYSQOQKC-UHFFFAOYSA-N

> <FORMULA>
C20H28O11

> <MOLECULAR_WEIGHT>
444.433

> <EXACT_MASS>
444.163161722

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
44.109055288439464

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate

> <ALOGPS_LOGP>
-0.11

> <JCHEM_LOGP>
-1.0817286230000003

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.143784945917588

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.193855826377535

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343686494

> <JCHEM_POLAR_SURFACE_AREA>
172.21

> <JCHEM_REFRACTIVITY>
102.09900000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      14.670  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      20.005   2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      21.339   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      22.673   2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      24.006   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      25.340   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      25.340   3.850   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      24.006   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      25.340  -0.770   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      22.673  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      22.673  -2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      21.339   0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      20.005  -0.770   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      18.672   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.900  -6.724   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.440  -4.056   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      16.004  -6.160   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   28                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   15   25                                                  
CONECT   25   24                                                            
CONECT   26   13   27                                                       
CONECT   27   26   10                                                       
CONECT   28    5   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoic acid	Generator

Chemical Formula

C₂₀H₂₈O₁₁

Average Mass

444.4330 Da

Monoisotopic Mass

444.16316 Da

IUPAC Name

(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate

Traditional Name

(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(=O)OC(C(=O)OCC1=CC=C(OC2OC(CO)C(O)C(O)C2O)C=C1)C(C)(C)O

InChI Identifier

InChI=1S/C20H28O11/c1-10(22)29-17(20(2,3)27)18(26)28-9-11-4-6-12(7-5-11)30-19-16(25)15(24)14(23)13(8-21)31-19/h4-7,13-17,19,21,23-25,27H,8-9H2,1-3H3

InChI Key

RXXZTHWYSQOQKC-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

Species Name	Source	Reference
Sicana odorifera	LOTUS Database	35616633

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
Hexose monosaccharide
O-glycosyl compound
Benzyloxycarbonyl
Phenoxy compound
Phenol ether
Fatty acid ester
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Monosaccharide
Fatty acyl
Oxane
Benzenoid
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Organic oxide
Hydrocarbon derivative
Alcohol
Primary alcohol
Carbonyl group
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	-0.11	ALOGPS
logP	-1.1	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	12.19	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	102.1 m³·mol⁻¹	ChemAxon
Polarizability	44.11 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

85226686

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate (NP0216004)

MOL for NP0216004 ((4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate)

3D MOL for NP0216004 ((4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate)

3D SDF for NP0216004 ((4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate)

3D-SDF for NP0216004 ((4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate)

PDB for NP0216004 ((4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate)

3D PDB for NP0216004 ((4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate)

SMILES for NP0216004 ((4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate)

INCHI for NP0216004 ((4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate)

Structure for NP0216004 ((4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate)

3D Structure for NP0216004 ((4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(acetyloxy)-3-hydroxy-3-methylbutanoate)