NP-MRD: Showing NP-Card for (2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside (NP0045801)

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Record Information

Version

2.0

Created at

2022-03-17 19:43:28 UTC

Updated at

2022-03-17 19:43:28 UTC

NP-MRD ID

NP0045801

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside

Description

(2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. (2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside is found in Eriobotrya japonica . Xanthophylls arise by oxygenation of the carotene backbone (2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212132D          

 42 46  0  0  0  0            999 V2000
   -4.0661    1.6795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7805    1.2670    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7805    0.4420    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0661    0.0294    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3516    0.4420    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3516    1.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0661    2.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4950    1.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4950    0.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0661   -0.7956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9227    0.4420    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2082    1.6795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9227    1.2670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2082    0.0295    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4937    0.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4937    1.2670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6518    0.8839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6371    1.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082    2.5045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2207    1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352    1.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082   -0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9227   -1.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9227   -2.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082   -2.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4937   -2.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4937   -1.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2207   -0.7955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2207   -2.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352   -2.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352   -1.2081    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6371   -0.7956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082   -3.2706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2207   -3.2706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497   -0.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497    0.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641   -1.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786   -0.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7931    0.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6371    0.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  6  0  0  0
  2  8  1  1  0  0  0
  3  9  1  6  0  0  0
  4 10  1  6  0  0  0
 13 11  1  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  5 17  1  6  0  0  0
 13 18  1  1  0  0  0
 12 19  1  6  0  0  0
 16 20  1  1  0  0  0
 20 21  1  0  0  0  0
 14 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 27  1  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
 28 27  1  0  0  0  0
 26 27  2  0  0  0  0
 26 29  1  0  0  0  0
 28 31  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 32  1  0  0  0  0
 25 33  1  0  0  0  0
 29 34  2  0  0  0  0
 31 35  1  6  0  0  0
 37 35  2  0  0  0  0
 35 38  1  0  0  0  0
 36 37  1  0  0  0  0
 36 40  2  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
  5 42  1  0  0  0  0
 11 42  1  6  0  0  0
M  END


  Mrv0541 02241212132D          

 42 46  0  0  0  0            999 V2000
   -4.0661    1.6795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7805    1.2670    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7805    0.4420    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0661    0.0294    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3516    0.4420    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3516    1.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0661    2.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4950    1.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4950    0.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0661   -0.7956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9227    0.4420    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2082    1.6795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9227    1.2670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2082    0.0295    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4937    0.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4937    1.2670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6518    0.8839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6371    1.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082    2.5045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2207    1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352    1.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082   -0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9227   -1.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9227   -2.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082   -2.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4937   -2.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4937   -1.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2207   -0.7955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2207   -2.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352   -2.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352   -1.2081    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6371   -0.7956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082   -3.2706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2207   -3.2706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497   -0.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497    0.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641   -1.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786   -0.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7931    0.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6371    0.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  6  0  0  0
  2  8  1  1  0  0  0
  3  9  1  6  0  0  0
  4 10  1  6  0  0  0
 13 11  1  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  5 17  1  6  0  0  0
 13 18  1  1  0  0  0
 12 19  1  6  0  0  0
 16 20  1  1  0  0  0
 20 21  1  0  0  0  0
 14 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 27  1  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
 28 27  1  0  0  0  0
 26 27  2  0  0  0  0
 26 29  1  0  0  0  0
 28 31  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 32  1  0  0  0  0
 25 33  1  0  0  0  0
 29 34  2  0  0  0  0
 31 35  1  6  0  0  0
 37 35  2  0  0  0  0
 35 38  1  0  0  0  0
 36 37  1  0  0  0  0
 36 40  2  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
  5 42  1  0  0  0  0
 11 42  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0045801

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2C2=C(O)C=C(O)C3=C2O[C@@H](CC3=O)C2=CC=C(O)C=C2)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O14/c1-9-19(33)21(35)23(37)27(38-9)41-26-22(36)20(34)16(8-28)40-25(26)18-13(31)6-12(30)17-14(32)7-15(39-24(17)18)10-2-4-11(29)5-3-10/h2-6,9,15-16,19-23,25-31,33-37H,7-8H2,1H3/t9-,15-,16+,19-,20+,21+,22-,23+,25-,26+,27-/m0/s1

> <INCHI_KEY>
LCTOQECBRZFOCD-SSAHSMSHSA-N

> <FORMULA>
C27H32O14

> <MOLECULAR_WEIGHT>
580.5346

> <EXACT_MASS>
580.179205732

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
55.54132173716252

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
-0.45

> <JCHEM_LOGP>
-0.6461385336666662

> <ALOGPS_LOGS>
-1.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.443709093669302

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.480839383503556

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121826114733837

> <JCHEM_POLAR_SURFACE_AREA>
236.05999999999995

> <JCHEM_REFRACTIVITY>
135.27769999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.95e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.590   3.135   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.924   2.365   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.924   0.825   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.590   0.055   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.256   0.825   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -6.256   2.365   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -7.590   4.675   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0     -10.257   3.135   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0     -10.257   0.055   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -7.590  -1.485   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.589   0.825   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.255   3.135   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.589   2.365   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.255   0.055   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.922   0.825   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.922   2.365   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0      -4.950   1.650   0.000  0.00  0.00           H+0
HETATM   18  O   UNK     0      -4.923   3.135   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.255   4.675   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.412   3.135   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.746   2.365   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.255  -1.485   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.589  -2.255   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.589  -3.795   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.255  -4.565   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.922  -3.795   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.922  -2.255   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.412  -1.485   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.412  -4.565   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.746  -3.795   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.746  -2.255   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.923  -1.485   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -2.255  -6.105   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.412  -6.105   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.079  -1.485   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.413   0.825   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.079   0.055   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.413  -2.255   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.747  -1.485   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.747   0.055   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       7.080   0.825   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -4.923   0.055   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3    8                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6   17   42                                             
CONECT    6    1    5                                                       
CONECT    7    1                                                            
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11   13   14   42                                                  
CONECT   12   13   16   19                                                  
CONECT   13   11   12   18                                                  
CONECT   14   11   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   12   15   20                                                  
CONECT   17    5                                                            
CONECT   18   13                                                            
CONECT   19   12                                                            
CONECT   20   16   21                                                       
CONECT   21   20                                                            
CONECT   22   14   23   27                                                  
CONECT   23   22   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   33                                                  
CONECT   26   25   27   29                                                  
CONECT   27   22   28   26                                                  
CONECT   28   27   31                                                       
CONECT   29   26   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   28   30   35                                                  
CONECT   32   23                                                            
CONECT   33   25                                                            
CONECT   34   29                                                            
CONECT   35   31   37   38                                                  
CONECT   36   37   40                                                       
CONECT   37   35   36                                                       
CONECT   38   35   39                                                       
CONECT   39   38   40                                                       
CONECT   40   36   39   41                                                  
CONECT   41   40                                                            
CONECT   42    5   11                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
(2S)-Naringenin 8-C-a-L-rhamnopyranosyl-(1->2)-b-D-glucopyranoside	Generator
(2S)-Naringenin 8-C-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside	Generator

Chemical Formula

C₂₇H₃₂O₁₄

Average Mass

580.5346 Da

Monoisotopic Mass

580.17921 Da

IUPAC Name

(2S)-8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2S)-8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

278614-43-0

SMILES

[H][C@@]1(O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2C2=C(O)C=C(O)C3=C2O[C@@H](CC3=O)C2=CC=C(O)C=C2)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C27H32O14/c1-9-19(33)21(35)23(37)27(38-9)41-26-22(36)20(34)16(8-28)40-25(26)18-13(31)6-12(30)17-14(32)7-15(39-24(17)18)10-2-4-11(29)5-3-10/h2-6,9,15-16,19-23,25-31,33-37H,7-8H2,1H3/t9-,15-,16+,19-,20+,21+,22-,23+,25-,26+,27-/m0/s1

InChI Key

LCTOQECBRZFOCD-SSAHSMSHSA-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
Eriobotrya japonica	FooDB	KNAPSACK
Rhaphiolepis bibas	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Xanthophylls

Alternative Parents

Substituents

Xanthophyll
Benzofuran
Dihydrofuran
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.45	ALOGPS
logP	-0.65	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	7.48	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	236.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	135.28 m³·mol⁻¹	ChemAxon
Polarizability	55.54 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

FDB001847

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

10603320

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside (NP0045801)

MOL for NP0045801 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

3D MOL for NP0045801 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

3D SDF for NP0045801 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

3D-SDF for NP0045801 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

PDB for NP0045801 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

3D PDB for NP0045801 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

SMILES for NP0045801 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

INCHI for NP0045801 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

Structure for NP0045801 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)

3D Structure for NP0045801 ((2S)-Naringenin 8-C-alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranoside)