NP-MRD: Showing NP-Card for glycosmisic acid 4'-sulfate (NP0307479)

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Record Information

Version

2.0

Created at

2022-09-11 00:37:45 UTC

Updated at

2022-09-11 00:37:45 UTC

NP-MRD ID

NP0307479

Secondary Accession Numbers

None

Natural Product Identification

Common Name

glycosmisic acid 4'-sulfate

Description

Glycosmisic acid 4'-sulfate, also known as g(8-5)fa sulfate or g(8-5)fa sulfuric acid, belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Glycosmisic acid 4'-sulfate is an extremely weak basic (essentially neutral) compound (based on its pKa). glycosmisic acid 4'-sulfate is found in Arabidopsis thaliana. A guaiacyl lignin that is glycosmisic acid in which the phenolic hydrogen is replaced by a sulfo group.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652310051710422D          

 33 35  0  0  0  0            999 V2000
   -3.9284    0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054   -0.1006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0554    1.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7534    2.9519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6265    2.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    0.0940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3409    2.2374    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.5396    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  3  2  0  0  0  0
 11  3  1  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  4  1  0  0  0  0
 12  9  2  0  0  0  0
 13  7  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  1  0  0  0  0
 15  5  1  0  0  0  0
 16  9  1  0  0  0  0
 16 15  2  0  0  0  0
 17  8  2  0  0  0  0
 18  6  1  0  0  0  0
 19 12  1  0  0  0  0
 19 14  1  0  0  0  0
 20 13  2  0  0  0  0
 20 17  1  0  0  0  0
 21 10  1  0  0  0  0
 22 18  2  0  0  0  0
 23 18  1  0  0  0  0
 27  1  1  0  0  0  0
 27 16  1  0  0  0  0
 28  2  1  0  0  0  0
 28 17  1  0  0  0  0
 29 19  1  0  0  0  0
 29 20  1  0  0  0  0
 30 15  1  0  0  0  0
 31 24  1  0  0  0  0
 31 25  2  0  0  0  0
 31 26  2  0  0  0  0
 31 30  1  0  0  0  0
 32  3  1  0  0  0  0
 33  6  1  0  0  0  0
M  END

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
   -4.5427    1.0326    2.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0414    0.8339    1.2658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1237    0.4496    0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7853    0.2581    0.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554   -0.1215   -0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4640   -0.2894    0.0185 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1300   -1.4772   -0.5013 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5157   -1.2637   -0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897   -2.1058   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307   -3.4871   -0.0723 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3297   -4.4464    0.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8753   -1.6606    0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0991   -0.2739   -0.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4459    0.2363    0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7703    1.4944    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1703    1.9378    0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0861    1.0839    0.4738 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209    3.2966    0.2491 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0585    0.5943   -0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7728    0.0831   -0.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4640    0.7388   -0.5911 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3549    2.0791    0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9101    2.5891   -0.2134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2939   -0.3238   -1.6885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6467   -0.1389   -1.9906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5307    0.2403   -1.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8605    0.4111   -1.3565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0033   -0.8190   -1.2948 S   0  0  0  0  0  6  0  0  0  0  0  0
   -7.9469   -0.6904   -2.4806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3907   -2.1913   -1.2566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9858   -0.6942    0.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0499    0.0884    2.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3257    1.3785    3.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7193    1.7813    2.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4655    0.4230    1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3776   -0.2393    1.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2104   -4.1682   -0.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5471   -4.5191    1.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9470   -5.4181   -0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7212   -2.3082    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2461   -0.4875    0.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0340    2.2451   -0.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    3.9372    0.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2105    1.6824   -0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2921    0.8672   -1.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5338    2.0440    1.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0950    2.7680   -0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283    3.2236    0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5814   -0.6163   -2.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0065   -0.2949   -3.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9668    0.2374    0.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  2  0
 14 13  1  0
 13 19  2  0
 19 20  1  0
 20  8  2  0
  8  7  1  0
  7  6  1  0
  6 21  1  0
 21 22  1  0
 22 23  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  3 26  2  0
 26 27  1  0
 27 28  1  0
 28 31  1  0
 28 29  2  0
 28 30  2  0
 26 25  1  0
 25 24  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 15 16  1  0
 16 18  1  0
 16 17  2  0
 12 13  1  0
 21 20  1  0
 24  5  1  0
 15 42  1  0
 14 41  1  0
 19 44  1  0
  6 36  1  1
 21 45  1  6
 22 46  1  0
 22 47  1  0
 23 48  1  0
  4 35  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 31 51  1  0
 25 50  1  0
 24 49  1  0
 11 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 18 43  1  0
M  END


  Mrv1652310051710422D          

 33 35  0  0  0  0            999 V2000
   -3.9284    0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054   -0.1006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0554    1.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7534    2.9519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6265    2.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    0.0940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3409    2.2374    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.5396    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  3  2  0  0  0  0
 11  3  1  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  4  1  0  0  0  0
 12  9  2  0  0  0  0
 13  7  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  1  0  0  0  0
 15  5  1  0  0  0  0
 16  9  1  0  0  0  0
 16 15  2  0  0  0  0
 17  8  2  0  0  0  0
 18  6  1  0  0  0  0
 19 12  1  0  0  0  0
 19 14  1  0  0  0  0
 20 13  2  0  0  0  0
 20 17  1  0  0  0  0
 21 10  1  0  0  0  0
 22 18  2  0  0  0  0
 23 18  1  0  0  0  0
 27  1  1  0  0  0  0
 27 16  1  0  0  0  0
 28  2  1  0  0  0  0
 28 17  1  0  0  0  0
 29 19  1  0  0  0  0
 29 20  1  0  0  0  0
 30 15  1  0  0  0  0
 31 24  1  0  0  0  0
 31 25  2  0  0  0  0
 31 26  2  0  0  0  0
 31 30  1  0  0  0  0
 32  3  1  0  0  0  0
 33  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0307479

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\[H])C1=CC2=C(OC(C2CO)C2=CC(OC)=C(OS(O)(=O)=O)C=C2)C(OC)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O10S/c1-27-16-9-12(4-5-15(16)30-31(24,25)26)19-14(10-21)13-7-11(3-6-18(22)23)8-17(28-2)20(13)29-19/h3-9,14,19,21H,10H2,1-2H3,(H,22,23)(H,24,25,26)/b6-3+

> <INCHI_KEY>
VDMHTGWQLREBFW-ZZXKWVIFSA-N

> <FORMULA>
C20H20O10S

> <MOLECULAR_WEIGHT>
452.43

> <EXACT_MASS>
452.077718018

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
43.952710196665336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[3-(hydroxymethyl)-7-methoxy-2-[3-methoxy-4-(sulfooxy)phenyl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoic acid

> <ALOGPS_LOGP>
0.38

> <JCHEM_LOGP>
-0.3633566313174292

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.6621893013521483

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.3023638071489145

> <JCHEM_PKA_STRONGEST_BASIC>
-2.71549003465105

> <JCHEM_POLAR_SURFACE_AREA>
148.82

> <JCHEM_REFRACTIVITY>
108.31609999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[3-(hydroxymethyl)-7-methoxy-2-[3-methoxy-4-(sulfooxy)phenyl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-17         0                                  
HETATM    1  C   UNK     0      -7.333   0.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.197   6.693   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.483   4.177   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.023   4.177   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.198  -0.237   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.483   1.509   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.744   0.132   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.793   2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.023   1.509   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.531  -1.007   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.250  -0.188   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.865  -0.237   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.531  -2.547   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -9.437   3.407   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -8.873   5.510   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -6.769   4.947   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -5.793   0.175   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -7.333   2.843   0.000  0.00  0.00           O+0
HETATM   31  S   UNK     0      -8.103   4.177   0.000  0.00  0.00           S+0
HETATM   32  H   UNK     0       6.531   2.073   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.864  -1.007   0.000  0.00  0.00           H+0
CONECT    1   27                                                            
CONECT    2   28                                                            
CONECT    3    6   11   32                                                  
CONECT    4    5   12                                                       
CONECT    5    4   15                                                       
CONECT    6    3   18   33                                                  
CONECT    7   11   13                                                       
CONECT    8   11   17                                                       
CONECT    9   12   16                                                       
CONECT   10   14   21                                                       
CONECT   11    3    7    8                                                  
CONECT   12    4    9   19                                                  
CONECT   13    7   14   20                                                  
CONECT   14   10   13   19                                                  
CONECT   15    5   16   30                                                  
CONECT   16    9   15   27                                                  
CONECT   17    8   20   28                                                  
CONECT   18    6   22   23                                                  
CONECT   19   12   14   29                                                  
CONECT   20   13   17   29                                                  
CONECT   21   10                                                            
CONECT   22   18                                                            
CONECT   23   18                                                            
CONECT   24   31                                                            
CONECT   25   31                                                            
CONECT   26   31                                                            
CONECT   27    1   16                                                       
CONECT   28    2   17                                                       
CONECT   29   19   20                                                       
CONECT   30   15   31                                                       
CONECT   31   24   25   26   30                                             
CONECT   32    3                                                            
CONECT   33    6                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
g(8-5)FA sulfate	ChEBI
g(8-5)FA sulfuric acid	Generator
g(8-5)FA sulphate	Generator
g(8-5)FA sulphuric acid	Generator
Glycosmisate 4'-sulfate	Generator
Glycosmisate 4'-sulphate	Generator
Glycosmisic acid 4'-sulfuric acid	Generator
Glycosmisic acid 4'-sulphuric acid	Generator

Chemical Formula

C₂₀H₂₀O₁₀S

Average Mass

452.4300 Da

Monoisotopic Mass

452.07772 Da

IUPAC Name

(2E)-3-[3-(hydroxymethyl)-7-methoxy-2-[3-methoxy-4-(sulfooxy)phenyl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoic acid

Traditional Name

(2E)-3-[3-(hydroxymethyl)-7-methoxy-2-[3-methoxy-4-(sulfooxy)phenyl]-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC2=C(OC(C2CO)C2=CC(OC)=C(OS(O)(=O)=O)C=C2)C(OC)=C1)C(O)=O

InChI Identifier

InChI=1S/C20H20O10S/c1-27-16-9-12(4-5-15(16)30-31(24,25)26)19-14(10-21)13-7-11(3-6-18(22)23)8-17(28-2)20(13)29-19/h3-9,14,19,21H,10H2,1-2H3,(H,22,23)(H,24,25,26)/b6-3+

InChI Key

VDMHTGWQLREBFW-ZZXKWVIFSA-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
Arabidopsis thaliana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Neolignan skeleton
Coumaric acid or derivatives
Phenylsulfate
Arylsulfate
Coumaran
Benzofuran
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Styrene
Alkyl aryl ether
Monocyclic benzene moiety
Sulfuric acid monoester
Sulfate-ester
Sulfuric acid ester
Benzenoid
Organic sulfuric acid or derivatives
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Primary alcohol
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	0.38	ALOGPS
logP	-0.36	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	-2.3	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	108.32 m³·mol⁻¹	ChemAxon
Polarizability	43.95 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0149541

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

121232655

PDB ID

Not Available

ChEBI ID

91211

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for glycosmisic acid 4'-sulfate (NP0307479)

MOL for NP0307479 (glycosmisic acid 4'-sulfate)

3D MOL for NP0307479 (glycosmisic acid 4'-sulfate)

3D SDF for NP0307479 (glycosmisic acid 4'-sulfate)

3D-SDF for NP0307479 (glycosmisic acid 4'-sulfate)

PDB for NP0307479 (glycosmisic acid 4'-sulfate)

3D PDB for NP0307479 (glycosmisic acid 4'-sulfate)

SMILES for NP0307479 (glycosmisic acid 4'-sulfate)

INCHI for NP0307479 (glycosmisic acid 4'-sulfate)

Structure for NP0307479 (glycosmisic acid 4'-sulfate)

3D Structure for NP0307479 (glycosmisic acid 4'-sulfate)