NP-MRD: Showing NP-Card for (2S)-7-O-beta-D-glucopyranosyl-5-hydroxyflavanone (NP0060532)

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Record Information

Version

2.0

Created at

2022-04-28 05:33:50 UTC

Updated at

2022-04-28 05:33:50 UTC

NP-MRD ID

NP0060532

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2S)-7-O-beta-D-glucopyranosyl-5-hydroxyflavanone

Description

Pinocembroside belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Thus, pinocembroside is considered to be a flavonoid. (2S)-7-O-beta-D-glucopyranosyl-5-hydroxyflavanone is found in Artemisia dracunculus, Echiochilon fruticosum, Enkianthus nudipes, Glycyrrhiza glabra , Penthorum chinense, Viscum articulactum, Viscum articulatum and Viscum coloratum . (2S)-7-O-beta-D-glucopyranosyl-5-hydroxyflavanone was first documented in 2018 (PMID: 29949914). Based on a literature review a small amount of articles have been published on Pinocembroside (PMID: 35335366) (PMID: 32359555) (PMID: 31877872).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207332D          

 30 33  0  0  1  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  3 12  1  0  0  0  0
 11 13  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  1 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  1  0  0  0
 26 27  1  0  0  0  0
 23 28  1  6  0  0  0
 22 29  1  1  0  0  0
 21 30  1  6  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    3.8376   -2.8591   -1.6597 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -2.3363   -0.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6779   -2.2723    0.4770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917   -1.0740    1.3526 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7510    0.1597    0.6036 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4527    1.4099    1.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6757    2.5834    0.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2091    2.5591   -0.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5014    1.3460   -1.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2830    0.1365   -0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1666   -1.0497    1.8914 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1006   -1.1302    0.9822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8752   -0.5855    1.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063   -0.6541    0.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4056   -0.1045    0.7615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5573   -0.0913   -0.0057 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9399    1.2373   -0.1595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1789    1.3740   -0.7629 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4053    2.8540   -1.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3647    3.4785    0.2413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2148    0.8277    0.1973 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5093    1.1291   -0.2082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9871   -0.6791    0.2234 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8767   -1.3392    1.0343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5945   -0.8945    0.7544 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2809   -2.2435    0.5985 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0480   -1.2879   -0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2877   -1.8431   -1.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5025   -2.4787   -2.3254 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3248   -1.7604   -0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6560   -2.3012   -0.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6236   -3.2115    1.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2079   -1.1264    2.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0308    1.4063    2.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4405    3.5489    0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4002    3.4821   -1.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9259    1.3246   -2.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5567   -0.7533   -1.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146   -0.0920    2.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3907   -0.5933   -0.9683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2625    0.8298   -1.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941    3.2323   -1.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4145    3.0493   -1.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4682    3.4088    0.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9763    1.2140    1.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8020    1.9368    0.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0215   -1.0138   -0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6808   -1.5687    0.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5928   -0.6786    1.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6237   -2.5963   -0.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7292   -1.3854   -1.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7188   -2.5241   -2.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 30  2  0
 30  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4 11  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 30 28  1  0
 28 29  1  0
 28 27  2  0
 16 25  1  0
 25 26  1  0
 25 23  1  0
 23 24  1  0
 23 21  1  0
 21 22  1  0
 21 18  1  0
 27 14  1  0
 11 12  1  0
 10  5  1  0
 20 44  1  0
 19 42  1  0
 19 43  1  0
 18 41  1  6
 16 40  1  6
 13 39  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  1
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 29 52  1  0
 27 51  1  0
 25 49  1  1
 26 50  1  0
 23 47  1  6
 24 48  1  0
 21 45  1  1
 22 46  1  0
M  END


  Mrv1652304282207332D          

 30 33  0  0  1  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  3 12  1  0  0  0  0
 11 13  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  1 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  1  0  0  0
 26 27  1  0  0  0  0
 23 28  1  6  0  0  0
 22 29  1  1  0  0  0
 21 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0060532

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC3=C(C(=O)C[C@H](O3)C3=CC=CC=C3)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O9/c22-9-16-18(25)19(26)20(27)21(30-16)28-11-6-12(23)17-13(24)8-14(29-15(17)7-11)10-4-2-1-3-5-10/h1-7,14,16,18-23,25-27H,8-9H2/t14-,16+,18+,19-,20+,21+/m0/s1

> <INCHI_KEY>
GPGFGFUBECSNTG-SFTVRKLSSA-N

> <FORMULA>
C21H22O9

> <MOLECULAR_WEIGHT>
418.398

> <EXACT_MASS>
418.126382288

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.67195655266275

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-5-hydroxy-2-phenyl-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
0.47

> <JCHEM_LOGP>
0.8706052786666667

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.199360881061224

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.638941421604706

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923437586574

> <JCHEM_POLAR_SURFACE_AREA>
145.91000000000003

> <JCHEM_REFRACTIVITY>
101.45329999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-5-hydroxy-2-phenyl-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-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      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2    6   19                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11    3                                                       
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    1   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   30                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   20                                                       
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   23                                                            
CONECT   29   22                                                            
CONECT   30   21                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₉

Average Mass

418.3980 Da

Monoisotopic Mass

418.12638 Da

IUPAC Name

(2S)-5-hydroxy-2-phenyl-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2S)-5-hydroxy-2-phenyl-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC3=C(C(=O)C[C@H](O3)C3=CC=CC=C3)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H22O9/c22-9-16-18(25)19(26)20(27)21(30-16)28-11-6-12(23)17-13(24)8-14(29-15(17)7-11)10-4-2-1-3-5-10/h1-7,14,16,18-23,25-27H,8-9H2/t14-,16+,18+,19-,20+,21+/m0/s1

InChI Key

GPGFGFUBECSNTG-SFTVRKLSSA-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
Artemisia dracunculus	LOTUS Database	35616633
Echiochilon fruticosum	LOTUS Database	35616633
Enkianthus nudipes	LOTUS Database	35616633
Glycyrrhiza glabra	Plant	KNApSAcK
Penthorum chinense	Plant	KNApSAcK
Viscum articulactum	Plant	KNApSAcK
Viscum articulatum	LOTUS Database	35616633
Viscum coloratum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
5-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Phenolic glycoside
Alkyl glycoside
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Chromane
1-benzopyran
Benzopyran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Oxane
Benzenoid
Fatty acyl
Monosaccharide
Vinylogous acid
Secondary alcohol
Ketone
Oxacycle
Polyol
Acetal
Ether
Organoheterocyclic compound
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aldehyde
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	0.47	ALOGPS
logP	0.87	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.64	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.45 m³·mol⁻¹	ChemAxon
Polarizability	41.67 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00014304

Chemspider ID

24675404

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46881227

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ferreira NS, Cascaes MM, da Silva Santos L, de Oliveira MS, das Gracas Bichara Zoghbi M, Araujo IS, Uetanabaro APT, de Aguiar Andrade EH, Guilhon GMSP: Flavanone Glycosides, Triterpenes, Volatile Compounds and Antimicrobial Activity of Miconia minutiflora (Bonpl.) DC. (Melastomataceae). Molecules. 2022 Mar 21;27(6). pii: molecules27062005. doi: 10.3390/molecules27062005. [PubMed:35335366 ]
Chen C, Wan C, Peng X, Chen J: A flavonone pinocembroside inhibits Penicillium italicum growth and blue mold development in 'Newhall' navel oranges by targeting membrane damage mechanism. Pestic Biochem Physiol. 2020 May;165:104505. doi: 10.1016/j.pestbp.2019.11.025. Epub 2019 Dec 2. [PubMed:32359555 ]
Chen C, Cai N, Chen J, Wan C: UHPLC-Q-TOF/MS-Based Metabolomics Approach Reveals the Antifungal Potential of Pinocembroside against Citrus Green Mold Phytopathogen. Plants (Basel). 2019 Dec 22;9(1). pii: plants9010017. doi: 10.3390/plants9010017. [PubMed:31877872 ]
Mikropoulou EV, Vougogiannopoulou K, Kalpoutzakis E, Sklirou AD, Skaperda Z, Houriet J, Wolfender JL, Trougakos IP, Kouretas D, Halabalaki M, Mitakou S: Phytochemical Composition of the Decoctions of Greek Edible Greens (Chorta) and Evaluation of Antioxidant and Cytotoxic Properties. Molecules. 2018 Jun 26;23(7). pii: molecules23071541. doi: 10.3390/molecules23071541. [PubMed:29949914 ]

Showing NP-Card for (2S)-7-O-beta-D-glucopyranosyl-5-hydroxyflavanone (NP0060532)

MOL for NP0060532 ((2S)-7-O-beta-D-glucopyranosyl-5-hydroxyflavanone)

3D MOL for NP0060532 ((2S)-7-O-beta-D-glucopyranosyl-5-hydroxyflavanone)

3D SDF for NP0060532 ((2S)-7-O-beta-D-glucopyranosyl-5-hydroxyflavanone)

3D-SDF for NP0060532 ((2S)-7-O-beta-D-glucopyranosyl-5-hydroxyflavanone)

PDB for NP0060532 ((2S)-7-O-beta-D-glucopyranosyl-5-hydroxyflavanone)

3D PDB for NP0060532 ((2S)-7-O-beta-D-glucopyranosyl-5-hydroxyflavanone)

SMILES for NP0060532 ((2S)-7-O-beta-D-glucopyranosyl-5-hydroxyflavanone)

INCHI for NP0060532 ((2S)-7-O-beta-D-glucopyranosyl-5-hydroxyflavanone)

Structure for NP0060532 ((2S)-7-O-beta-D-glucopyranosyl-5-hydroxyflavanone)

3D Structure for NP0060532 ((2S)-7-O-beta-D-glucopyranosyl-5-hydroxyflavanone)