NP-MRD: Showing NP-Card for 2,4-dihydroxy-2-[(4-hydroxyphenyl)methyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one (NP0309860)

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Record Information

Version

2.0

Created at

2022-09-11 04:44:27 UTC

Updated at

2022-09-11 04:44:27 UTC

NP-MRD ID

NP0309860

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4-dihydroxy-2-[(4-hydroxyphenyl)methyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one

Description

Maesopsin 6-glucoside belongs to the class of organic compounds known as aurone o-glycosides. These are aurone flavonoids containing a carbohydrate moiety O-glycosidically bound to the aurone skeleton. Maesopsin 6-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Maesopsin 6-glucoside has been detected, but not quantified in, tea. 2,4-dihydroxy-2-[(4-hydroxyphenyl)methyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one is found in Ceanothus americanus. This could make maesopsin 6-glucoside a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061306002D          

 32 35  0  0  0  0            999 V2000
   -1.3570    2.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9154    1.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1416    2.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7001    0.7581    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
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407    2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7439    1.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132    1.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.6979    0.0000 C   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
    6.2102    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.9354    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
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0978    1.0552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407    0.9709    0.0000 O   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    1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  9  1  2  0  0  0  0
  9  2  1  0  0  0  0
  9  7  1  0  0  0  0
 10  3  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  5  1  0  0  0  0
 13  6  2  0  0  0  0
 14  8  1  0  0  0  0
 15 12  2  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 15  1  0  0  0  0
 20 18  1  0  0  0  0
 21  7  1  0  0  0  0
 21 19  1  0  0  0  0
 22  8  1  0  0  0  0
 23 10  1  0  0  0  0
 24 12  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  1  0  0  0  0
 27 18  1  0  0  0  0
 28 19  2  0  0  0  0
 29 21  1  0  0  0  0
 30 11  1  0  0  0  0
 30 20  1  0  0  0  0
 31 14  1  0  0  0  0
 31 20  1  0  0  0  0
 32 13  1  0  0  0  0
 32 21  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    3.3252   -3.9646    0.2678 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8903   -2.8037    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4747   -2.4095    0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3755   -3.0576    0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5155   -4.3212    1.2595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8458   -2.4300    0.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9806   -1.1646    0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2099   -0.5543   -0.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5537    0.6713   -0.5762 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1969    1.5197    0.3016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4272    1.1535    0.7127 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3844    2.3142    0.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0059    3.4562    1.1330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9871   -0.1153    0.1808 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7356   -1.1877    1.0375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5716   -0.4817   -1.2005 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6619   -0.5792   -2.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5329    0.4786   -1.7483 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8123   -0.1064   -2.7879 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1453   -0.5655   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4022   -1.1729   -0.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6511   -0.7616   -0.8735 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6266   -1.5672   -0.2849 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6980   -1.8333   -1.1314 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0781   -0.9244    1.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6320    0.4055    0.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9667    0.5539    0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5245    1.7830    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6931    2.8832    0.1060 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2047    4.1385   -0.1872 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3502    2.7396    0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7933    1.4936    0.6961 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4029   -4.7859    1.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7018   -2.9512    1.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6972    1.1965   -0.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4088    1.0556    1.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3844    2.0047    0.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5300    2.5074   -0.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8312    4.0031    1.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1116   -0.0036    0.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3390   -0.9261    1.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0864   -1.4934   -1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4094   -0.9994   -1.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9557    1.4284   -2.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7979   -1.0978   -2.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1268    0.4022   -0.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9907   -2.7856   -1.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8753   -1.5753    1.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2547   -0.9133    1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6309   -0.3157    0.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5661    1.9459   -0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5592    4.7223    0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6672    3.5747    0.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7380    1.4162    0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  4  1  0
  4  5  1  0
  4  3  2  0
  3 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 23  2  1  0
  2  1  2  0
 21 20  2  0
  9 18  1  0
 18 19  1  0
 18 16  1  0
 16 17  1  0
 16 14  1  0
 14 15  1  0
 14 11  1  0
 20  7  1  0
  2  3  1  0
 32 26  1  0
 13 39  1  0
 12 37  1  0
 12 38  1  0
 11 36  1  1
  9 35  1  6
  6 34  1  0
  5 33  1  0
 24 47  1  0
 25 48  1  0
 25 49  1  0
 27 50  1  0
 28 51  1  0
 30 52  1  0
 31 53  1  0
 32 54  1  0
 20 46  1  0
 18 44  1  6
 19 45  1  0
 16 42  1  1
 17 43  1  0
 14 40  1  6
 15 41  1  0
M  END


  Mrv0541 05061306002D          

 32 35  0  0  0  0            999 V2000
   -1.3570    2.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9154    1.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1416    2.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7001    0.7581    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
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407    2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7439    1.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132    1.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.6979    0.0000 C   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
    6.2102    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.9354    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
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0978    1.0552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407    0.9709    0.0000 O   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    1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  9  1  2  0  0  0  0
  9  2  1  0  0  0  0
  9  7  1  0  0  0  0
 10  3  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  5  1  0  0  0  0
 13  6  2  0  0  0  0
 14  8  1  0  0  0  0
 15 12  2  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 15  1  0  0  0  0
 20 18  1  0  0  0  0
 21  7  1  0  0  0  0
 21 19  1  0  0  0  0
 22  8  1  0  0  0  0
 23 10  1  0  0  0  0
 24 12  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  1  0  0  0  0
 27 18  1  0  0  0  0
 28 19  2  0  0  0  0
 29 21  1  0  0  0  0
 30 11  1  0  0  0  0
 30 20  1  0  0  0  0
 31 14  1  0  0  0  0
 31 20  1  0  0  0  0
 32 13  1  0  0  0  0
 32 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0309860

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=CC(O)=C3C(OC(O)(CC4=CC=C(O)C=C4)C3=O)=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O11/c22-8-14-16(25)17(26)18(27)20(31-14)30-11-5-12(24)15-13(6-11)32-21(29,19(15)28)7-9-1-3-10(23)4-2-9/h1-6,14,16-18,20,22-27,29H,7-8H2

> <INCHI_KEY>
MWYRZWOULAZZHR-UHFFFAOYSA-N

> <FORMULA>
C21H22O11

> <MOLECULAR_WEIGHT>
450.3928

> <EXACT_MASS>
450.116211546

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
43.13068564144906

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4-dihydroxy-2-[(4-hydroxyphenyl)methyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-3-one

> <ALOGPS_LOGP>
-0.18

> <JCHEM_LOGP>
0.5046813533333333

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.404349913355073

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.21800144261448

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923437586574

> <JCHEM_POLAR_SURFACE_AREA>
186.36999999999998

> <JCHEM_REFRACTIVITY>
105.2177

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4-dihydroxy-2-[(4-hydroxyphenyl)methyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.533   4.428   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.709   1.891   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.998   3.952   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.174   1.415   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.076   3.873   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.259  -0.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.389   3.397   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.318   2.446   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.259   1.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.592   2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.592   3.613   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.592  -1.007   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -5.783   1.970   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      12.926   1.303   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      12.926   4.383   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      10.259   5.923   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.650   0.132   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.076   1.812   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       8.925   2.073   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
CONECT    1    3    9                                                       
CONECT    2    4    9                                                       
CONECT    3    1   10                                                       
CONECT    4    2   10                                                       
CONECT    5   11   12                                                       
CONECT    6   11   13                                                       
CONECT    7    9   21                                                       
CONECT    8   14   22                                                       
CONECT    9    1    2    7                                                  
CONECT   10    3    4   23                                                  
CONECT   11    5    6   30                                                  
CONECT   12    5   15   24                                                  
CONECT   13    6   15   32                                                  
CONECT   14    8   16   31                                                  
CONECT   15   12   13   19                                                  
CONECT   16   14   17   25                                                  
CONECT   17   16   18   26                                                  
CONECT   18   17   20   27                                                  
CONECT   19   15   21   28                                                  
CONECT   20   18   30   31                                                  
CONECT   21    7   19   29   32                                             
CONECT   22    8                                                            
CONECT   23   10                                                            
CONECT   24   12                                                            
CONECT   25   16                                                            
CONECT   26   17                                                            
CONECT   27   18                                                            
CONECT   28   19                                                            
CONECT   29   21                                                            
CONECT   30   11   20                                                       
CONECT   31   14   20                                                       
CONECT   32   13   21                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₁₁

Average Mass

450.3928 Da

Monoisotopic Mass

450.11621 Da

IUPAC Name

2,4-dihydroxy-2-[(4-hydroxyphenyl)methyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-3-one

Traditional Name

2,4-dihydroxy-2-[(4-hydroxyphenyl)methyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2=CC(O)=C3C(OC(O)(CC4=CC=C(O)C=C4)C3=O)=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C21H22O11/c22-8-14-16(25)17(26)18(27)20(31-14)30-11-5-12(24)15-13(6-11)32-21(29,19(15)28)7-9-1-3-10(23)4-2-9/h1-6,14,16-18,20,22-27,29H,7-8H2

InChI Key

MWYRZWOULAZZHR-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
Ceanothus americanus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aurone o-glycosides. These are aurone flavonoids containing a carbohydrate moiety O-glycosidically bound to the aurone skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Aurone O-glycosides

Alternative Parents

Substituents

Aurone-6-o-glycoside
Auronol
Aurone
Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Coumaran
Benzofuran
Aryl ketone
Aryl alkyl ketone
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Acyloin
Oxane
Monosaccharide
Vinylogous acid
Ketone
Secondary alcohol
Hemiacetal
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Primary alcohol
Organooxygen compound
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	-0.18	ALOGPS
logP	0.5	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.22	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	105.22 m³·mol⁻¹	ChemAxon
Polarizability	43.13 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031555

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008167

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

74819327

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,4-dihydroxy-2-[(4-hydroxyphenyl)methyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one (NP0309860)

MOL for NP0309860 (2,4-dihydroxy-2-[(4-hydroxyphenyl)methyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

3D MOL for NP0309860 (2,4-dihydroxy-2-[(4-hydroxyphenyl)methyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

3D SDF for NP0309860 (2,4-dihydroxy-2-[(4-hydroxyphenyl)methyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

3D-SDF for NP0309860 (2,4-dihydroxy-2-[(4-hydroxyphenyl)methyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

PDB for NP0309860 (2,4-dihydroxy-2-[(4-hydroxyphenyl)methyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

3D PDB for NP0309860 (2,4-dihydroxy-2-[(4-hydroxyphenyl)methyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

SMILES for NP0309860 (2,4-dihydroxy-2-[(4-hydroxyphenyl)methyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

INCHI for NP0309860 (2,4-dihydroxy-2-[(4-hydroxyphenyl)methyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

Structure for NP0309860 (2,4-dihydroxy-2-[(4-hydroxyphenyl)methyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

3D Structure for NP0309860 (2,4-dihydroxy-2-[(4-hydroxyphenyl)methyl]-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)