NP-MRD: Showing NP-Card for Chafuroside A (NP0085229)

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Record Information

Version

2.0

Created at

2022-04-29 05:48:33 UTC

Updated at

2022-04-29 05:48:33 UTC

NP-MRD ID

NP0085229

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chafuroside A

Description

Chafuroside A belongs to the class of organic compounds known as furanoflavones. These are polycyclic aromatic compounds containing a furan ring fused to a flavan-3-one. Chafuroside A is found in Camellia sinensis . Chafuroside A was first documented in 2009 (PMID: 19572651). Based on a literature review a small amount of articles have been published on Chafuroside A (PMID: 31474732) (PMID: 27581633) (PMID: 22108345).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207482D          

 32 36  0  0  1  0            999 V2000
   -0.2931   -1.7561    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -2.5379    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3143   -3.2878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1632   -3.9606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9846   -3.8834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4622   -4.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2835   -4.4790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3285   -3.1335    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1498   -3.0563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8509   -2.4607    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1948   -1.7108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5071   -3.2106    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1338   -3.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7529   -3.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5903   -4.5466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5347   -3.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6973   -2.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4791   -2.4018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0982   -2.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8800   -2.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0426   -1.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8244   -1.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4435   -2.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2253   -1.8928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2809   -2.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4991   -3.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356   -3.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1538   -4.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9912   -4.8283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0782   -2.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -2.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5774   -1.9791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  6  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
  3 12  1  1  0  0  0
  3 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 20 26  1  0  0  0  0
 19 27  2  0  0  0  0
 27 28  1  0  0  0  0
 16 28  1  0  0  0  0
 28 29  2  0  0  0  0
 17 30  1  0  0  0  0
 30 31  2  0  0  0  0
 13 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
M  END

     RDKit          3D

 48 52  0  0  0  0  0  0  0  0999 V2000
    1.2641   -1.9055   -2.6502 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6877   -1.2980   -1.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0281   -0.9818   -1.5059 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4873   -0.3095   -0.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9021    0.0344   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8827   -0.2675   -1.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2205    0.0932   -0.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5832    0.7660    0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9154    1.1182    0.4649 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5903    1.0759    1.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2842    0.7096    0.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6043    0.0193    0.5203 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3236   -0.2429    0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4566    0.1443    1.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9076   -0.1506    1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4148   -0.8203    0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5302   -1.1879   -0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9667   -1.8650   -1.8236 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317   -0.9149   -0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8998   -0.9836    0.4789 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5774   -0.7608   -0.6951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8890   -0.4235   -0.3852 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7797   -0.4703   -1.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3059    0.4343   -2.5731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8588    1.0176    0.0780 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1237    1.3189    0.5752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8503    1.2282    1.1769 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8632    2.0808    0.6932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1854   -0.0566    1.5940 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9547    0.1204    2.2457 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7309   -1.2801   -2.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6309   -0.7931   -2.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9912   -0.1504   -1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1885    1.6073    1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8917    1.5994    2.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5160    0.9626    1.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8629    0.6709    2.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9392   -2.0864   -1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1306   -2.0323    0.7973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2819   -1.1161    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7995   -0.1597   -1.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8154   -1.4909   -2.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0423    0.8338   -3.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6877    1.6480   -0.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4982    0.5665    1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3030    1.6957    2.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4185    2.5913    1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8501   -0.5887    2.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 30  1  0
 30 15  1  0
 15 14  2  0
 14 13  1  0
 13 19  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
 19 17  1  0
 17 18  1  0
 17 16  2  0
 16 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 20 29  1  0
 27 29  1  0
 16 15  1  0
 12 13  1  0
 11  5  1  0
 29 48  1  1
 14 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
 18 38  1  0
 20 39  1  1
 22 40  1  1
 23 41  1  0
 23 42  1  0
 24 43  1  0
 25 44  1  6
 26 45  1  0
 27 46  1  1
 28 47  1  0
M  END


  Mrv1652304292207482D          

 32 36  0  0  1  0            999 V2000
   -0.2931   -1.7561    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -2.5379    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3143   -3.2878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1632   -3.9606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9846   -3.8834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4622   -4.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2835   -4.4790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3285   -3.1335    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1498   -3.0563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8509   -2.4607    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1948   -1.7108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5071   -3.2106    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1338   -3.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7529   -3.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5903   -4.5466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5347   -3.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6973   -2.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4791   -2.4018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0982   -2.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8800   -2.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0426   -1.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8244   -1.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4435   -2.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2253   -1.8928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2809   -2.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4991   -3.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356   -3.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1538   -4.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9912   -4.8283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0782   -2.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -2.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5774   -1.9791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  6  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
  3 12  1  1  0  0  0
  3 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 20 26  1  0  0  0  0
 19 27  2  0  0  0  0
 27 28  1  0  0  0  0
 16 28  1  0  0  0  0
 28 29  2  0  0  0  0
 17 30  1  0  0  0  0
 30 31  2  0  0  0  0
 13 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085229

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12OC3=CC4=C(C(=O)C=C(O4)C4=CC=C(O)C=C4)C(O)=C3[C@]1([H])O[C@H](CO)[C@@H](O)[C@@H]2O

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

> <INCHI_KEY>
DZQBNDGXEFWXEK-ODJUOBDQSA-N

> <FORMULA>
C21H18O9

> <MOLECULAR_WEIGHT>
414.366

> <EXACT_MASS>
414.09508216

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
41.465467675446874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(11S,13R,14S,15S,16S)-9,14,15-trihydroxy-13-(hydroxymethyl)-5-(4-hydroxyphenyl)-4,12,17-trioxatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1,3(8),5,9-tetraen-7-one

> <ALOGPS_LOGP>
1.08

> <JCHEM_LOGP>
0.6138393533333333

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.731552478487503

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.908634588919929

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9791932391727807

> <JCHEM_POLAR_SURFACE_AREA>
145.91

> <JCHEM_REFRACTIVITY>
102.25319999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(11S,13R,14S,15S,16S)-9,14,15-trihydroxy-13-(hydroxymethyl)-5-(4-hydroxyphenyl)-4,12,17-trioxatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1,3(8),5,9-tetraen-7-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  H   UNK     0      -0.547  -3.278   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -0.055  -4.737   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.587  -6.137   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.305  -7.393   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.838  -7.249   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.729  -8.505   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.263  -8.361   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.480  -5.849   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.013  -5.705   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.588  -4.593   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.230  -3.193   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0      -0.947  -5.993   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       2.116  -5.959   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.272  -6.977   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.969  -8.487   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.731  -6.485   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.035  -4.975   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.494  -4.483   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.650  -5.501   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.109  -5.009   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.413  -3.499   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.872  -3.007   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.028  -4.025   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.487  -3.533   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.724  -5.535   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.265  -6.027   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.346  -7.011   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.887  -7.503   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.584  -9.013   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.879  -3.958   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.420  -4.450   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.078  -3.694   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10   32                                             
CONECT    3    2    4   12   13                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    2   11                                                  
CONECT   11   10                                                            
CONECT   12    3                                                            
CONECT   13    3   14   31                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   28                                                  
CONECT   17   16   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   20                                                       
CONECT   27   19   28                                                       
CONECT   28   27   16   29                                                  
CONECT   29   28                                                            
CONECT   30   17   31                                                       
CONECT   31   30   13   32                                                  
CONECT   32   31    2                                                       
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 b	MeSH

Chemical Formula

C₂₁H₁₈O₉

Average Mass

414.3660 Da

Monoisotopic Mass

414.09508 Da

IUPAC Name

(11S,13R,14S,15S,16S)-9,14,15-trihydroxy-13-(hydroxymethyl)-5-(4-hydroxyphenyl)-4,12,17-trioxatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1,3(8),5,9-tetraen-7-one

Traditional Name

(11S,13R,14S,15S,16S)-9,14,15-trihydroxy-13-(hydroxymethyl)-5-(4-hydroxyphenyl)-4,12,17-trioxatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1,3(8),5,9-tetraen-7-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12OC3=CC4=C(C(=O)C=C(O4)C4=CC=C(O)C=C4)C(O)=C3[C@]1([H])O[C@H](CO)[C@@H](O)[C@@H]2O

InChI Identifier

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

InChI Key

DZQBNDGXEFWXEK-ODJUOBDQSA-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 furanoflavones. These are polycyclic aromatic compounds containing a furan ring fused to a flavan-3-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Furanoflavones

Alternative Parents

Substituents

Furanoflavone
Furanoflavonoid or dihydroflavonoid
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Furanochromone
Chromone
1-benzopyran
Benzopyran
Coumaran
Alkyl aryl ether
Pyranone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Benzenoid
Monosaccharide
Pyran
Oxane
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Polyol
Primary alcohol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	1.08	ALOGPS
logP	0.61	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	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	41.47 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

C00055013

Chemspider ID

9444958

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11269948

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 ]
Onoue S, Matsui T, Aoki Y, Ishida H, Nukaya H, Kou K, Yamada S: Self-assembled micellar formulation of chafuroside A with improved anti-inflammatory effects in experimental asthma/COPD-model rats. Eur J Pharm Sci. 2012 Jan 23;45(1-2):184-9. doi: 10.1016/j.ejps.2011.11.003. Epub 2011 Nov 13. [PubMed:22108345 ]
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 ]

Showing NP-Card for Chafuroside A (NP0085229)

MOL for NP0085229 (Chafuroside A)

3D MOL for NP0085229 (Chafuroside A)

3D SDF for NP0085229 (Chafuroside A)

3D-SDF for NP0085229 (Chafuroside A)

PDB for NP0085229 (Chafuroside A)

3D PDB for NP0085229 (Chafuroside A)

SMILES for NP0085229 (Chafuroside A)

INCHI for NP0085229 (Chafuroside A)

Structure for NP0085229 (Chafuroside A)

3D Structure for NP0085229 (Chafuroside A)