NP-MRD: Showing NP-Card for Helichrysin A (NP0044190)

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Record Information

Version

2.0

Created at

2021-11-12 23:55:35 UTC

Updated at

2021-11-26 17:46:26 UTC

NP-MRD ID

NP0044190

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Helichrysin A

Description

Helichrysin A belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Helichrysin A is found in Abies nephrolepis, Acacia spp. , Glebionis coronaria, Cinnamomum subavenium, Helichrysum arenarium, Helichrysum armenium, Helichrysum spp., Nymphaea caerulea, Persica vulgaris , Prunus spp. , Salix purpurea and Salix spp.. Helichrysin A was first documented in 2013 (PMID: 25090681). Based on a literature review very few articles have been published on Helichrysin A (PMID: 32383693).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100562D          

 31 34  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    0.0000    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
    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  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -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
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 10 12  1  0  0  0  0
  8 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  1  0  0  0
 20 21  1  0  0  0  0
 17 22  1  6  0  0  0
 16 23  1  1  0  0  0
 15 24  1  6  0  0  0
  2 25  1  6  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
    0.4351   -0.0203    2.0469 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2290    0.1570    1.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6732   -0.1576    1.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5480    0.8788    0.6678 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8709    0.3768    0.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6382    1.2656   -0.5215 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8667    0.9444   -1.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3945   -0.3021   -0.7448 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6631   -0.6252   -1.2462 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6569   -1.2038    0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3947   -0.8571    0.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9625    1.5027   -0.4553 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6954    1.3628   -0.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2994    1.8789   -2.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0047    1.7073   -2.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3996    2.2278   -3.8279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8998    1.0288   -1.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5483    0.5058   -0.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4181   -0.1675    0.2220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7420   -0.5265   -0.0407 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5756    0.4235    0.5128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8806    0.0475    0.6349 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6725    1.1696    1.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6285    2.3311    0.4782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1643   -1.2277    1.3019 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2041   -1.9522    0.7202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9556   -2.0683    1.5147 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2918   -1.7800    2.7034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0577   -1.9227    0.3107 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7282   -2.5517   -0.7652 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7521    0.6824   -0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8580   -1.1956    0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8815   -0.1461    2.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7558    1.7187    1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2539    2.2570   -0.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4570    1.6346   -1.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7932   -1.0483   -2.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0839   -2.1747    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8274   -1.5550    1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0201    2.4079   -2.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7582    3.1721   -3.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9092    0.9451   -2.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8952   -0.4010   -1.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2719   -0.0478   -0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3206    1.4663    2.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7575    0.8905    1.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8324    2.1608   -0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5520   -0.9897    2.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9372   -2.2003   -0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2729   -3.1352    1.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3605   -0.8034    2.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1654   -2.5570    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8153   -3.5269   -0.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4 12  1  0
 12 13  1  0
 13 31  2  0
 31  2  1  0
  2  1  2  0
 31 18  1  0
 18 17  2  0
 17 15  1  0
 15 14  2  0
 15 16  1  0
 18 19  1  0
 19 20  1  0
 20 29  1  0
 29 27  1  0
 27 25  1  0
 25 22  1  0
 22 21  1  0
 22 23  1  0
 23 24  1  0
 25 26  1  0
 27 28  1  0
 29 30  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8 10  1  0
 10 11  2  0
  8  9  1  0
  2  3  1  0
 14 13  1  0
 21 20  1  0
 11  5  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  1
 17 42  1  0
 14 40  1  0
 16 41  1  0
 20 43  1  6
 29 52  1  1
 27 50  1  1
 25 48  1  1
 22 44  1  6
 23 45  1  0
 23 46  1  0
 24 47  1  0
 26 49  1  0
 28 51  1  0
 30 53  1  0
  6 35  1  0
  7 36  1  0
 10 38  1  0
 11 39  1  0
  9 37  1  0
M  END


  Mrv1652311132100562D          

 31 34  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    0.0000    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
    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  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -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
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 10 12  1  0  0  0  0
  8 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  1  0  0  0
 20 21  1  0  0  0  0
 17 22  1  6  0  0  0
 16 23  1  1  0  0  0
 15 24  1  6  0  0  0
  2 25  1  6  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044190

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC(O)=CC3=C2C(=O)C[C@H](O3)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O10/c22-8-16-18(26)19(27)20(28)21(31-16)30-15-6-11(24)5-14-17(15)12(25)7-13(29-14)9-1-3-10(23)4-2-9/h1-6,13,16,18-24,26-28H,7-8H2/t13-,16+,18+,19-,20+,21+/m0/s1

> <INCHI_KEY>
MFQIWHVVFBCURA-ITSUVCJSSA-N

> <FORMULA>
C21H22O10

> <MOLECULAR_WEIGHT>
434.397

> <EXACT_MASS>
434.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
42.68329136048641

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-7-hydroxy-2-(4-hydroxyphenyl)-5-{[(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>
0.14

> <JCHEM_LOGP>
-0.08296004299999998

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.480257936344925

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.802497766599483

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923463048313

> <JCHEM_POLAR_SURFACE_AREA>
166.14000000000001

> <JCHEM_REFRACTIVITY>
103.4342

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-7-hydroxy-2-(4-hydroxyphenyl)-5-{[(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                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   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  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    4                                                       
CONECT   12   10                                                            
CONECT   13    8   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   17                                                            
CONECT   23   16                                                            
CONECT   24   15                                                            
CONECT   25    2   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   28                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₁₀

Average Mass

434.3970 Da

Monoisotopic Mass

434.12130 Da

IUPAC Name

(2S)-7-hydroxy-2-(4-hydroxyphenyl)-5-{[(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)-7-hydroxy-2-(4-hydroxyphenyl)-5-{[(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=CC(O)=CC3=C2C(=O)C[C@H](O3)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H22O10/c22-8-16-18(26)19(27)20(28)21(31-16)30-15-6-11(24)5-14-17(15)12(25)7-13(29-14)9-1-3-10(23)4-2-9/h1-6,13,16,18-24,26-28H,7-8H2/t13-,16+,18+,19-,20+,21+/m0/s1

InChI Key

MFQIWHVVFBCURA-ITSUVCJSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abies nephrolepis	LOTUS Database	35616633
Acacia spp.	Plant	KNApSAcK
Chrysanthemum coronarium	LOTUS Database	35616633
Cinnamomum subavenium	LOTUS Database	35616633
Helichrysum arenarium	LOTUS Database	35616633
Helichrysum armenium	LOTUS Database	35616633
Helichrysum spp.	Plant	KNApSAcK
Nymphaea caerulea	Plant	KNApSAcK
Prunus persica	-	KNApSAcK
Prunus spp.	Plant	KNApSAcK
Salix purpurea	LOTUS Database	35616633
Salix spp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid-5-o-glycoside
Flavonoid o-glycoside
4'-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Phenolic glycoside
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Aryl ketone
Aryl alkyl ketone
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monosaccharide
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Ketone
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Primary alcohol
Organic oxygen compound
Organic oxide
Aldehyde
Alcohol
Hydrocarbon derivative
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	0.14	ALOGPS
logP	-0.083	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	7.8	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	103.43 m³·mol⁻¹	ChemAxon
Polarizability	42.68 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

Not Available

Chemspider ID

20100728

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15559669

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Aydin T: Secondary metabolites of Helichrysum plicatum DC. subsp. plicatum flowers as strong carbonic anhydrase, cholinesterase and alpha-glycosidase inhibitors. Z Naturforsch C J Biosci. 2020 May 26;75(5-6):153-159. doi: 10.1515/znc-2020-0026. [PubMed:32383693 ]
Zuo FH, Wu GJ, Li JJ, Zhou GP, Fu HZ, Liao YY: [Chemical constituents of Salix matsudana leaf]. Zhong Yao Cai. 2013 Dec;36(12):1959-62. [PubMed:25090681 ]
WANG Li-Bo, TOSHI Morikawa, GAO Hui-Yuan, SUN Bo-Hang, HUANG Jiang, MASAYUKI Yoshikawa, WU Li-Jun (2009). Flavones from Helichrysi flos SYN. Chinese Journal of Natural Medicines, 34(11):1381-3, DOI:10.3724/SP.J.1009.2009.00357. Chinese Journal of Natural Medicines.

Showing NP-Card for Helichrysin A (NP0044190)

MOL for NP0044190 (Helichrysin A)

3D MOL for NP0044190 (Helichrysin A)

3D SDF for NP0044190 (Helichrysin A)

3D-SDF for NP0044190 (Helichrysin A)

PDB for NP0044190 (Helichrysin A)

3D PDB for NP0044190 (Helichrysin A)

SMILES for NP0044190 (Helichrysin A)

INCHI for NP0044190 (Helichrysin A)

Structure for NP0044190 (Helichrysin A)

3D Structure for NP0044190 (Helichrysin A)