NP-MRD: Showing NP-Card for Chafuroside B (NP0084968)

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Record Information

Version

2.0

Created at

2022-04-29 05:34:17 UTC

Updated at

2022-04-29 05:34:17 UTC

NP-MRD ID

NP0084968

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chafuroside B

Description

Chafuroside B belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Chafuroside B is found in Camellia sinensis . Chafuroside B was first documented in 2009 (PMID: 19572651). Based on a literature review a small amount of articles have been published on Chafuroside B (PMID: 31474732) (PMID: 27581633) (PMID: 32351166) (PMID: 24116222).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207342D          

 32 36  0  0  1  0            999 V2000
    4.1676   -1.7368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5270   -1.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6569   -0.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0163    0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463    0.9324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9168    1.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0467    2.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4061    2.5618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5360    3.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3065    3.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4364    4.4860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9471    3.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8172    2.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5574    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4274   -0.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0680   -0.6272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7565   -1.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1159   -0.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2458   -0.1772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5111    0.1981    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9272   -0.3846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3009   -1.1201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073   -1.0252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1305   -0.1702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4535   -0.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0822    0.6269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8789    0.8412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5018    1.2096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2891    2.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8731    2.5895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2984    0.9952    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
  6 14  2  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
  2 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 22 24  1  6  0  0  0
 22 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 20 32  1  0  0  0  0
M  END

     RDKit          3D

 48 52  0  0  0  0  0  0  0  0999 V2000
    2.7050   -3.0976    2.9025 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2582   -2.3407    2.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0059   -1.3525    1.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4910   -0.5189    0.4341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2935    0.5173   -0.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6828    1.3005   -1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3844    2.3096   -1.8341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7191    2.5439   -1.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4186    3.5486   -2.1880 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3338    1.7664   -0.5726 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6074    0.7765    0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2288   -0.7002    0.1104 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4392   -1.6035    0.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8844   -1.6912    0.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7269   -2.6299    0.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2129   -3.4714    1.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0871   -3.3887    2.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6262   -4.2211    3.1323 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9359   -2.4471    1.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0047   -2.5366    0.1599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1179   -1.2505   -0.3639 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6737   -0.9508   -0.7845 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5000    0.4106   -0.7383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6688    1.0850   -1.0863 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3924    2.5428   -1.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5915    3.1661   -1.7438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6511    1.0790    0.0911 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9673    1.1004   -0.3621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4557   -0.2802    0.7701 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2933   -0.1686    1.5350 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0358   -1.2262    1.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6521    1.1860   -1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9375    2.9372   -2.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4690    4.5063   -1.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3713    1.9719   -0.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1199    0.1907    0.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8391   -4.2333    2.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0010   -4.9117    3.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7953   -1.1560   -1.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5300   -1.3957   -1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1762    0.6426   -1.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9903    3.0819   -0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7115    2.6146   -2.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6088    3.4928   -2.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4279    1.9147    0.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0498    0.7831   -1.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3307   -0.5913    1.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2011    0.6952    1.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 15  1  0
 15 14  2  0
 14 13  1  0
 13 19  2  0
 19 17  1  0
 17 18  1  0
 17 16  2  0
 19  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4 12  1  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  2  0
 14 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 22 21  1  0
 29 21  1  0
 16 15  1  0
 11  5  1  0
 12 13  1  0
 21 39  1  6
 18 38  1  0
 16 37  1  0
  3 31  1  0
  6 32  1  0
  7 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 22 40  1  6
 24 41  1  6
 25 42  1  0
 25 43  1  0
 26 44  1  0
 27 45  1  1
 28 46  1  0
 29 47  1  1
 30 48  1  0
M  END


  Mrv1652304292207342D          

 32 36  0  0  1  0            999 V2000
    4.1676   -1.7368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5270   -1.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6569   -0.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0163    0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463    0.9324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9168    1.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0467    2.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4061    2.5618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5360    3.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3065    3.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4364    4.4860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9471    3.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8172    2.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5574    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4274   -0.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0680   -0.6272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7565   -1.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1159   -0.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2458   -0.1772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5111    0.1981    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9272   -0.3846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3009   -1.1201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073   -1.0252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1305   -0.1702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4535   -0.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0822    0.6269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8789    0.8412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5018    1.2096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2891    2.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8731    2.5895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2984    0.9952    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
  6 14  2  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
  2 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 22 24  1  6  0  0  0
 22 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 20 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084968

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12OC3=C(C4=C(C(O)=C3)C(=O)C=C(O4)C3=CC=C(O)C=C3)[C@]1([H])O[C@H](CO)[C@@H](O)[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O9/c22-7-14-17(26)18(27)21-20(30-14)16-13(29-21)6-11(25)15-10(24)5-12(28-19(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-18,20-23,25-27H,7H2/t14-,17-,18+,20+,21+/m1/s1

> <INCHI_KEY>
PCWAOEHIAAYHJX-WTLMAMESSA-N

> <FORMULA>
C21H18O9

> <MOLECULAR_WEIGHT>
414.366

> <EXACT_MASS>
414.09508216

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
40.51980772920618

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(12S,13S,14S,15R,17S)-8,13,14-trihydroxy-15-(hydroxymethyl)-4-(4-hydroxyphenyl)-3,11,16-trioxatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-1(10),2(7),4,8-tetraen-6-one

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
0.6138393533333333

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.73999798671088

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.27431716460869

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9791932414950377

> <JCHEM_POLAR_SURFACE_AREA>
145.91

> <JCHEM_REFRACTIVITY>
102.2532

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(12S,13S,14S,15R,17S)-8,13,14-trihydroxy-15-(hydroxymethyl)-4-(4-hydroxyphenyl)-3,11,16-trioxatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-1(10),2(7),4,8-tetraen-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       7.780  -3.242   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.584  -2.272   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.826  -0.751   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.630   0.220   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.873   1.740   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.311   2.291   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.554   3.812   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.358   4.782   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.601   6.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.039   6.853   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.281   8.374   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.235   5.883   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.992   4.362   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.507   1.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.265  -0.200   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.460  -1.171   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.145  -2.822   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.950  -1.852   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.192  -0.331   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.821   0.370   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0       1.731  -0.718   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.428  -2.091   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0       0.760  -1.914   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       0.244  -0.318   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.847  -1.406   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.153   1.170   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.641   1.570   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.937   2.258   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.540   3.746   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.630   4.834   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.424   1.858   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7                                                       
CONECT   14    6   15                                                       
CONECT   15   14    3   16                                                  
CONECT   16   15                                                            
CONECT   17    2   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18    4   20                                                  
CONECT   20   19   21   22   32                                             
CONECT   21   20                                                            
CONECT   22   20   23   24   25                                             
CONECT   23   22   18                                                       
CONECT   24   22                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   20                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
3,4,11-Trihydroxy-2-(hydroxymethyl)-8-(4-hydroxyphenyl)-3,4,4a,11b-tetrahydro-2H,10H-pyrano(2',3'-4,5)furo(3,2-g)chromen-10-one	MeSH
Chafuroside	MeSH
Chafuroside a	MeSH

Chemical Formula

C₂₁H₁₈O₉

Average Mass

414.3660 Da

Monoisotopic Mass

414.09508 Da

IUPAC Name

(12S,13S,14S,15R,17S)-8,13,14-trihydroxy-15-(hydroxymethyl)-4-(4-hydroxyphenyl)-3,11,16-trioxatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-1(10),2(7),4,8-tetraen-6-one

Traditional Name

(12S,13S,14S,15R,17S)-8,13,14-trihydroxy-15-(hydroxymethyl)-4-(4-hydroxyphenyl)-3,11,16-trioxatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-1(10),2(7),4,8-tetraen-6-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12OC3=C(C4=C(C(O)=C3)C(=O)C=C(O4)C3=CC=C(O)C=C3)[C@]1([H])O[C@H](CO)[C@@H](O)[C@@H]2O

InChI Identifier

InChI=1S/C21H18O9/c22-7-14-17(26)18(27)21-20(30-14)16-13(29-21)6-11(25)15-10(24)5-12(28-19(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-18,20-23,25-27H,7H2/t14-,17-,18+,20+,21+/m1/s1

InChI Key

PCWAOEHIAAYHJX-WTLMAMESSA-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
Camellia sinensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Chromone
1-benzopyran
Benzopyran
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Pyranone
Pyran
Monosaccharide
Oxane
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Dialkyl ether
Ether
Polyol
Organic oxide
Organic oxygen compound
Primary alcohol
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	1.15	ALOGPS
logP	0.61	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.27	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	2	ChemAxon
Refractivity	102.25 m³·mol⁻¹	ChemAxon
Polarizability	40.52 Å³	ChemAxon
Number of Rings	5	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

C00054620

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

46832074

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Iwao Y, Ishida H, Kimura SI, Wakimoto T, Kondo H, Itai S, Noguchi S: Crystal Structures of Flavone C-Glycosides from Oolong Tea Leaves: Chafuroside A Dihydrate and Chafuroside B Monohydrate. Chem Pharm Bull (Tokyo). 2019;67(9):935-939. doi: 10.1248/cpb.c19-00166. [PubMed:31474732 ]
Tanaka H, Iwao Y, Izumikawa M, Sano S, Ishida H, Noguchi S, Itai S: Preparation of Orally Disintegrating Tablets Containing Powdered Tea Leaves with Enriched Levels of Bioactive Compounds by Means of Microwave Irradiation Technique. Chem Pharm Bull (Tokyo). 2016;64(9):1288-97. doi: 10.1248/cpb.c16-00224. [PubMed:27581633 ]
Ishida H, Wakimoto T, Kitao Y, Tanaka S, Miyase T, Nukaya H: Quantitation of chafurosides A and B in tea leaves and isolation of prechafurosides A and B from oolong tea leaves. J Agric Food Chem. 2009 Aug 12;57(15):6779-86. doi: 10.1021/jf900032z. [PubMed:19572651 ]
Kurahayashi K, Hanaya K, Higashibayashi S, Sugai T: Improved preparation of vitexin from hot water extract of Basella alba, the commercially available vegetable Malabar spinach ("Tsurumurasaki" in Japanese) and the application to semisynthesis of chafuroside B. Biosci Biotechnol Biochem. 2020 Aug;84(8):1554-1559. doi: 10.1080/09168451.2020.1761286. Epub 2020 Apr 30. [PubMed:32351166 ]
Hasegawa T, Shimada S, Ishida H, Nakashima M: Chafuroside B, an Oolong tea polyphenol, ameliorates UVB-induced DNA damage and generation of photo-immunosuppression related mediators in human keratinocytes. PLoS One. 2013 Oct 8;8(10):e77308. doi: 10.1371/journal.pone.0077308. eCollection 2013. [PubMed:24116222 ]

Showing NP-Card for Chafuroside B (NP0084968)

MOL for NP0084968 (Chafuroside B)

3D MOL for NP0084968 (Chafuroside B)

3D SDF for NP0084968 (Chafuroside B)

3D-SDF for NP0084968 (Chafuroside B)

PDB for NP0084968 (Chafuroside B)

3D PDB for NP0084968 (Chafuroside B)

SMILES for NP0084968 (Chafuroside B)

INCHI for NP0084968 (Chafuroside B)

Structure for NP0084968 (Chafuroside B)

3D Structure for NP0084968 (Chafuroside B)