NP-MRD: Showing NP-Card for Sulfurein (NP0055397)

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Record Information

Version

2.0

Created at

2022-04-28 01:27:53 UTC

Updated at

2022-04-28 01:27:53 UTC

NP-MRD ID

NP0055397

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sulfurein

Description

Sulfurein 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. Sulfurein is found in Baeria chrysostoma, Bahiopsis lanata, Bahiopsis tomentosa, Bidens spp., Butea monosperma , Calanticaria brevifolia, Calanticaria greggii, Coreopsis spp., Cosmos sulphureus, Cotinus coggygria, Dahlia variabilis , Helianthus heterophyllus, Helianthus radula, Jasminum officinale , Simsia spp., Tithonia koelzii, Viguiera multiflora and Wedelia prostrata. Sulfurein was first documented in 2000 (PMID: 11141121). Based on a literature review very few articles have been published on sulfurein.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282203272D          

 31 34  0  0  1  0            999 V2000
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    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
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2135    0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9279   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9279   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2135   -1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4990   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  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
  8 13  1  0  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
 11 16  1  6  0  0  0
 10 17  1  1  0  0  0
  9 18  1  6  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  0  0  0  0
 20 30  1  0  0  0  0
  1 30  1  0  0  0  0
 30 31  2  0  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    2.5003    0.0923    4.0806 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095    0.0647    2.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4373   -0.0173    1.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7401   -0.0814    2.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7373   -0.1628    0.9699 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5734   -0.8527   -0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5733   -0.8723   -1.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7735   -0.1961   -0.9427 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7728   -0.2340   -1.9226 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9409    0.4910    0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1327    1.1853    0.4624 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9251    0.5088    1.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8574   -0.0191    0.5766 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4604    0.0603    0.7520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4424    0.0896   -0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8917    0.1704    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8661    0.1958   -0.8127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2308    0.2709   -0.6953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7917   -0.9533   -1.1396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1497   -0.8715   -0.8400 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7655   -2.2456   -0.7078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1201   -2.1587   -0.4125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7852   -0.0803   -1.9488 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0171    0.4679   -1.5445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8663    1.0043   -2.4664 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2478    0.5935   -3.6444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8603    1.4346   -1.4238 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5199    2.2801   -0.5305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1729    0.2210    1.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724    0.1925    2.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1407    0.1122    2.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0625   -0.0693    3.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6692   -1.3796   -0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4904   -1.4036   -2.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6321    0.2686   -1.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2392    1.6928    1.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1298    1.0752    2.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6881    0.0504   -1.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5266    0.3287    0.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2748   -0.2963    0.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2841   -2.8002    0.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6330   -2.7910   -1.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3193   -1.6010    0.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0195   -0.7813   -2.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7344   -0.1866   -1.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5046    1.8729   -2.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1555   -0.4053   -3.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1042    2.0642   -1.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7148    3.1538   -0.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2067    0.2855    1.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3934    0.2322    3.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 31  2  0
 31 30  1  0
 30 29  2  0
 31  2  1  0
  2  1  2  0
  2  3  1  0
  3 13  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 18 27  1  0
 27 28  1  0
 27 25  1  0
 25 26  1  0
 25 23  1  0
 23 24  1  0
 23 20  1  0
 29 16  1  0
 12  5  1  0
 13 14  1  0
 22 43  1  0
 21 41  1  0
 21 42  1  0
 20 40  1  1
 18 39  1  1
 15 38  1  0
 30 51  1  0
 29 50  1  0
  4 32  1  0
  6 33  1  0
  7 34  1  0
  9 35  1  0
 11 36  1  0
 12 37  1  0
 27 48  1  6
 28 49  1  0
 25 46  1  6
 26 47  1  0
 23 44  1  6
 24 45  1  0
M  END


  Mrv1652304282203272D          

 31 34  0  0  1  0            999 V2000
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    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
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2135    0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9279   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9279   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2135   -1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4990   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  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
  8 13  1  0  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
 11 16  1  6  0  0  0
 10 17  1  1  0  0  0
  9 18  1  6  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  0  0  0  0
 20 30  1  0  0  0  0
  1 30  1  0  0  0  0
 30 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0055397

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC3=C(C=C2)C(=O)\C(O3)=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-10-2-3-11-14(7-10)30-15(17(11)25)6-9-1-4-12(23)13(24)5-9/h1-7,16,18-24,26-28H,8H2/b15-6-/t16-,18-,19+,20-,21-/m1/s1

> <INCHI_KEY>
MEHCTOVFPFJFEW-LTEMJKMTSA-N

> <FORMULA>
C21H20O10

> <MOLECULAR_WEIGHT>
432.381

> <EXACT_MASS>
432.105646844

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
42.46353405042906

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-3-one

> <ALOGPS_LOGP>
0.80

> <JCHEM_LOGP>
0.023510258000000284

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.977764933539122

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.829021952516282

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343722586

> <JCHEM_POLAR_SURFACE_AREA>
166.14

> <JCHEM_REFRACTIVITY>
105.13339999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.198   0.237   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.531  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.865   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.199  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.199  -2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.865  -2.843   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.531  -2.073   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.865  -4.383   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.199  -5.153   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      10.533  -2.843   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.533   0.237   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.865   1.777   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.268  -0.057   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.713  -1.303   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.483   0.031   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.023   0.031   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.793   1.365   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.023   2.698   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.483   2.698   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.713   1.365   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.713   4.032   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -5.793   4.032   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.744  -4.013   0.000  0.00  0.00           O+0
CONECT    1    2    6   30                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16   11                                                            
CONECT   17   10                                                            
CONECT   18    9                                                            
CONECT   19    2   20                                                       
CONECT   20   19   21   30                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26                                                            
CONECT   29   25                                                            
CONECT   30   20    1   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
Sulphurein	Generator

Chemical Formula

C₂₁H₂₀O₁₀

Average Mass

432.3810 Da

Monoisotopic Mass

432.10565 Da

IUPAC Name

(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-3-one

Traditional Name

(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC3=C(C=C2)C(=O)\C(O3)=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-10-2-3-11-14(7-10)30-15(17(11)25)6-9-1-4-12(23)13(24)5-9/h1-7,16,18-24,26-28H,8H2/b15-6-/t16-,18-,19+,20-,21-/m1/s1

InChI Key

MEHCTOVFPFJFEW-LTEMJKMTSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Baeria chrysostoma	Plant	KNApSAcK
Bahiopsis lanata	LOTUS Database	35616633
Bahiopsis tomentosa	LOTUS Database	35616633
Bidens spp.	Plant	KNApSAcK
Butea monosperma	Plant	KNApSAcK
Calanticaria brevifolia	LOTUS Database	35616633
Calanticaria greggii	LOTUS Database	35616633
Coreopsis spp.	Plant	KNApSAcK
Cosmos sulphureus	LOTUS Database	35616633
Cotinus coggygria	Plant	KNApSAcK
Dahlia variabilis	Plant	KNApSAcK
Helianthus heterophyllus	LOTUS Database	35616633
Helianthus radula	LOTUS Database	35616633
Jasminum officinale	Plant	KNApSAcK
Simsia spp.	Plant	KNApSAcK
Tithonia koelzii	Plant	KNApSAcK
Viguiera multiflora	Plant	KNApSAcK
Wedelia prostrata	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
Aurone
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Phenolic glycoside
Alkyl glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Coumaran
Benzofuran
Catechol
Aryl ketone
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Fatty acyl
Oxane
Monocyclic benzene moiety
Monosaccharide
Secondary alcohol
Ketone
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Aldehyde
Primary alcohol
Organic oxygen compound
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	0.8	ALOGPS
logP	0.024	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	8.83	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	105.13 m³·mol⁻¹	ChemAxon
Polarizability	42.46 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

C00008043

Chemspider ID

8246982

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10071442

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Westenburg HE, Lee KJ, Lee SK, Fong HH, van Breemen RB, Pezzuto JM, Kinghorn AD: Activity-guided isolation of antioxidative constituents of Cotinus coggygria. J Nat Prod. 2000 Dec;63(12):1696-8. doi: 10.1021/np000292h. [PubMed:11141121 ]

Showing NP-Card for Sulfurein (NP0055397)

MOL for NP0055397 (Sulfurein)

3D MOL for NP0055397 (Sulfurein)

3D SDF for NP0055397 (Sulfurein)

3D-SDF for NP0055397 (Sulfurein)

PDB for NP0055397 (Sulfurein)

3D PDB for NP0055397 (Sulfurein)

SMILES for NP0055397 (Sulfurein)

INCHI for NP0055397 (Sulfurein)

Structure for NP0055397 (Sulfurein)

3D Structure for NP0055397 (Sulfurein)