NP-MRD: Showing NP-Card for Kakonein (NP0054042)

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Record Information

Version

2.0

Created at

2022-04-28 00:31:20 UTC

Updated at

2022-04-28 00:31:20 UTC

NP-MRD ID

NP0054042

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Kakonein

Description

Puerarin, also known as kakonein, belongs to the class of organic compounds known as isoflavonoid c-glycosides. These are c-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. Puerarin is an extremely weak basic (essentially neutral) compound (based on its pKa). Kakonein is found in Aloe vera , Arabidopsis thaliana, Bupleurum chinense, Bupleurum scorzonerifolium , Cephalotaxus koreana, Cicer arietinum , Clematis hexapetala, Psoralea corylifolia , Erycibe expansa , Erythroxylum ulei, Acca sellowiana, Glycine max , Glycyrrhiza glabra , Phaseolus vulgaris , Pisum sativum , Pterocarpus marsupium , Pueraria calycina, Pueraria candollei var. mirifica, Pueraria edulis, Pueraria lobata , Pueraria lobata var.thomsonii , Pueraria mirifica , Pueraria montana, Pueraria montana var. lobata, Pueraria omeiensis, Pueraria peduncularis, Pueraria phaseoloides , Pueraria thomsonii , Pueraria thunbergiana , Pueraria tuberosa , Sarcolobus globosus, Sorbus cuspidata, Trifolium pratense , Vigna radiata and Ziziphus jujuba. Kakonein was first documented in 2015 (PMID: 25310912). A hydroxyisoflavone that is isoflavone substituted by hydroxy groups at positions 7 and 4' and a beta-D-glucopyranosyl residue at position 8 via a C-glycosidic linkage (PMID: 25553536).

Structure

MOL 3D MOL SDF PDB SMILES InChI

      
  Mrv1652304091820022D          

 30 33  0  0  0  0            999 V2000
 9979.0227 9981.6377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9981.8744 9979.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9985.4434 9978.7449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9979.0227 9984.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.3086 9983.7026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9981.8776 9982.4639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9981.8776 9984.1128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.4506 9984.9373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.4506 9984.1147    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9979.7361 9983.7022    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9979.7361 9982.8771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.4506 9982.4648    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9981.1651 9982.8771    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9981.1651 9983.7022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9984.7294 9979.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.0151 9980.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.3005 9979.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.3005 9979.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.0150 9978.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.7294 9979.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.4500 9981.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.7354 9981.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.7353 9980.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.4499 9979.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.8751 9981.6342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9981.1607 9981.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.1607 9980.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.8751 9979.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.5896 9980.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.5896 9981.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13  6  1  1  0  0  0
 14  7  1  6  0  0  0
  9  8  1  1  0  0  0
 10  4  1  6  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 15  1  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
  1 22  1  0  0  0  0
 12 21  1  6  0  0  0
 20  3  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 26  1  0  0  0  0
 25 30  1  0  0  0  0
 28  2  2  0  0  0  0
 26 21  2  0  0  0  0
 24 27  2  0  0  0  0
 29 17  1  0  0  0  0
M  END

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
    3.5890    1.5493    1.3537 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5893    0.9626    0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8124   -0.1329    0.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1702   -0.5874   -0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5074   -1.9271   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8009   -2.3426   -0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8297   -1.4592   -0.6879 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1145   -1.9358   -0.9160 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4807   -0.1256   -0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1878    0.2842   -0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7102   -0.7635   -0.4654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4874   -0.3166   -0.1969 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2749    0.7345    0.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653    1.1007    0.7806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1094    0.3082    0.1261 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1935    0.6079   -1.2427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8299   -0.3517   -1.9627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6964    0.3680   -3.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3289   -0.6740   -3.7177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7293   -1.2515   -1.1684 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0783   -2.4558   -0.8710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3580   -0.6022    0.0089 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6506   -0.1225   -0.2098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4960    0.4697    0.6728 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5092    0.2809    2.0661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2841    2.1875    1.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5809    2.6148    1.8232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2179    2.8922    2.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0859    2.5170    1.9475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3166    1.4300    1.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7090   -2.6180    0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0521   -3.3958   -0.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8135   -2.0338   -0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2793    0.5755   -1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9094    1.3423   -0.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7928   -1.6162   -1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8578   -0.7854    0.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0805   -0.9762   -2.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1244    1.0291   -3.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4920    0.8810   -2.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2929   -0.4857   -3.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5650   -1.5612   -1.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5194   -2.9217   -0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4765   -1.4131    0.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0699   -0.7528   -0.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9842    1.4281    0.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6791   -0.1357    2.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7440    3.3843    2.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4263    3.7517    2.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9266    3.0442    2.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 24  1  0
 24 25  1  0
 24 22  1  0
 22 23  1  0
 22 20  1  0
 20 21  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  1  0
 11  3  2  0
  3  2  1  0
  2  1  2  0
  2 30  1  0
 30 29  2  0
 29 28  1  0
 28 26  2  0
 26 27  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 20 17  1  0
 26 14  1  0
 10  4  1  0
 30 13  1  0
 19 41  1  0
 18 39  1  0
 18 40  1  0
 17 38  1  6
 15 37  1  6
 24 46  1  1
 25 47  1  0
 22 44  1  1
 23 45  1  0
 20 42  1  6
 21 43  1  0
 11 36  1  0
 29 50  1  0
 28 49  1  0
 27 48  1  0
  5 31  1  0
  6 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
M  END

      
  Mrv1652304091820022D          

 30 33  0  0  0  0            999 V2000
 9979.0227 9981.6377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9981.8744 9979.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9985.4434 9978.7449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9979.0227 9984.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.3086 9983.7026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9981.8776 9982.4639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9981.8776 9984.1128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.4506 9984.9373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.4506 9984.1147    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9979.7361 9983.7022    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9979.7361 9982.8771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.4506 9982.4648    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9981.1651 9982.8771    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9981.1651 9983.7022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9984.7294 9979.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.0151 9980.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.3005 9979.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.3005 9979.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.0150 9978.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.7294 9979.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.4500 9981.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.7354 9981.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.7353 9980.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.4499 9979.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.8751 9981.6342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9981.1607 9981.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.1607 9980.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.8751 9979.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.5896 9980.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.5896 9981.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13  6  1  1  0  0  0
 14  7  1  6  0  0  0
  9  8  1  1  0  0  0
 10  4  1  6  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 15  1  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
  1 22  1  0  0  0  0
 12 21  1  6  0  0  0
 20  3  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 26  1  0  0  0  0
 25 30  1  0  0  0  0
 28  2  2  0  0  0  0
 26 21  2  0  0  0  0
 24 27  2  0  0  0  0
 29 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054042

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2OC=C(C(=O)C2=CC=C1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O9/c22-7-14-17(26)18(27)19(28)21(30-14)15-13(24)6-5-11-16(25)12(8-29-20(11)15)9-1-3-10(23)4-2-9/h1-6,8,14,17-19,21-24,26-28H,7H2/t14-,17-,18+,19-,21+/m1/s1

> <INCHI_KEY>
HKEAFJYKMMKDOR-VPRICQMDSA-N

> <FORMULA>
C21H20O9

> <MOLECULAR_WEIGHT>
416.3781

> <EXACT_MASS>
416.110732238

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
41.18731577771669

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-3-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
-0.02688319366666661

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.96382450844034

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.029875705606582

> <JCHEM_PKA_STRONGEST_BASIC>
-2.979192629201714

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
102.8203

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
puerarin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-APR-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-APR-18         0                                  
HETATM    1  O   UNK     0    8627.5098632.390   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8632.8328627.755   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8639.4948626.990   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8627.5098637.011   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8626.1768636.245   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8632.8388633.933   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8632.8388637.011   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8630.1748638.550   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8630.1748637.014   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8628.8418636.244   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8628.8418634.704   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8630.1748633.934   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8631.5088634.704   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8631.5088636.244   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8638.1628629.301   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8636.8288630.071   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8635.4948629.301   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8635.4948627.761   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8636.8288626.991   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8638.1628627.761   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8630.1738632.384   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8628.8398631.614   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8628.8398630.074   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8630.1738629.303   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0    8632.8348632.384   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0    8631.5008631.614   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8631.5008630.074   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8632.8348629.304   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8634.1678630.074   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8634.1678631.614   0.000  0.00  0.00           C+0
CONECT    1   22                                                            
CONECT    2   28                                                            
CONECT    3   20                                                            
CONECT    4    5   10                                                       
CONECT    5    4                                                            
CONECT    6   13                                                            
CONECT    7   14                                                            
CONECT    8    9                                                            
CONECT    9   10   14    8                                                  
CONECT   10    9   11    4                                                  
CONECT   11   10   12                                                       
CONECT   12   13   11   21                                                  
CONECT   13   12   14    6                                                  
CONECT   14    9   13    7                                                  
CONECT   15   16   20                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   29                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15    3                                                  
CONECT   21   22   12   26                                                  
CONECT   22   21   23    1                                                  
CONECT   23   22   24                                                       
CONECT   24   23   27                                                       
CONECT   25   26   30                                                       
CONECT   26   27   25   21                                                  
CONECT   27   26   28   24                                                  
CONECT   28   27   29    2                                                  
CONECT   29   28   30   17                                                  
CONECT   30   29   25                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
Kakonein	HMDB
Daidzein 8-C-glucoside	HMDB

Chemical Formula

C₂₁H₂₀O₉

Average Mass

416.3781 Da

Monoisotopic Mass

416.11073 Da

IUPAC Name

7-hydroxy-3-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

Traditional Name

puerarin

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2OC=C(C(=O)C2=CC=C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C21H20O9/c22-7-14-17(26)18(27)19(28)21(30-14)15-13(24)6-5-11-16(25)12(8-29-20(11)15)9-1-3-10(23)4-2-9/h1-6,8,14,17-19,21-24,26-28H,7H2/t14-,17-,18+,19-,21+/m1/s1

InChI Key

HKEAFJYKMMKDOR-VPRICQMDSA-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
Aloe vera	Plant	KNApSAcK
Arabidopsis thaliana	Plant	KNApSAcK
Bupleurum chinense	LOTUS Database	35616633
Bupleurum scorzonerifolium	Plant	KNApSAcK
Cephalotaxus koreana	Plant	KNApSAcK
Cicer arietinum	Plant	KNApSAcK
Clematis hexapetala	LOTUS Database	35616633
Cullen corylifolium	Plant	KNApSAcK
Erycibe expansa	Plant	KNApSAcK
Erythroxylum ulei	Plant	KNApSAcK
Feijoa sellowiana	Plant	KNApSAcK
Glycine max	Plant	KNApSAcK
Glycyrrhiza glabra	Plant	KNApSAcK
Phaseolus vulgaris	Plant	KNApSAcK
Pisum sativum	Plant	KNApSAcK
Pterocarpus marsupium	Plant	KNApSAcK
Pueraria calycina	Plant	KNApSAcK
Pueraria candollei var. mirifica	Plant	KNApSAcK
Pueraria edulis	Plant	KNApSAcK
Pueraria lobata	Plant	KNApSAcK
Pueraria lobata var.thomsonii	Plant	KNApSAcK
Pueraria mirifica	Plant	KNApSAcK
Pueraria montana	LOTUS Database	35616633
Pueraria montana var. lobata	Plant	KNApSAcK
Pueraria omeiensis	Plant	KNApSAcK
Pueraria peduncularis	Plant	KNApSAcK
Pueraria Phaseoloides	Plant	KNApSAcK
Pueraria thomsonii	Plant	KNApSAcK
Pueraria thunbergiana	Plant	KNApSAcK
Pueraria tuberosa	Plant	KNApSAcK
Sarcolobus globosus	-	KNApSAcK
Sorbus cuspidata	LOTUS Database	35616633
Trifolium pratense	Plant	KNApSAcK
Vigna radiata	Plant	KNApSAcK
Ziziphus jujuba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavonoid c-glycosides. These are c-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavonoid C-glycosides

Direct Parent

Isoflavonoid C-glycosides

Alternative Parents

Substituents

Isoflavonoid c-glycoside
Isoflavonoid-8-c-glycoside
Hydroxyisoflavonoid
Isoflavone
Phenolic glycoside
Hexose monosaccharide
C-glycosyl compound
Chromone
Glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Monocyclic benzene moiety
Benzenoid
Oxane
Monosaccharide
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

C-glycosyl compound (CHEBI:8633 )
hydroxyisoflavone (CHEBI:8633 )
isoflavones (C10524 )
Isoflavonoids (C10524 )

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	0.48	ALOGPS
logP	-0.027	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.03	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	102.82 m³·mol⁻¹	ChemAxon
Polarizability	41.19 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

HMDB0240265

DrugBank ID

DB12290

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029976

KNApSAcK ID

C00006094

Chemspider ID

Not Available

KEGG Compound ID

C10524

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Puerarin

METLIN ID

Not Available

PubChem Compound

5281807

PDB ID

Not Available

ChEBI ID

8633

Good Scents ID

Not Available

References

General References

Zhao J, Cheng YY, Fan W, Yang CB, Ye SF, Cui W, Wei W, Lao LX, Cai J, Han YF, Rong JH: Botanical drug puerarin coordinates with nerve growth factor in the regulation of neuronal survival and neuritogenesis via activating ERK1/2 and PI3K/Akt signaling pathways in the neurite extension process. CNS Neurosci Ther. 2015 Jan;21(1):61-70. doi: 10.1111/cns.12334. Epub 2014 Oct 14. [PubMed:25310912 ]
Guo HD, Zhang QF, Chen JG, Shangguang XC, Guo YX: Large scale purification of puerarin from Puerariae Lobatae Radix through resins adsorption and acid hydrolysis. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Feb 1;980:8-15. doi: 10.1016/j.jchromb.2014.12.014. Epub 2014 Dec 20. [PubMed:25553536 ]

Showing NP-Card for Kakonein (NP0054042)

MOL for NP0054042 (Kakonein)

3D MOL for NP0054042 (Kakonein)

3D SDF for NP0054042 (Kakonein)

3D-SDF for NP0054042 (Kakonein)

PDB for NP0054042 (Kakonein)

3D PDB for NP0054042 (Kakonein)

SMILES for NP0054042 (Kakonein)

INCHI for NP0054042 (Kakonein)

Structure for NP0054042 (Kakonein)

3D Structure for NP0054042 (Kakonein)