NP-MRD: Showing NP-Card for epiafzelechin (NP0031144)

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Record Information

Version

2.0

Created at

2021-06-19 22:18:33 UTC

Updated at

2021-06-29 23:59:33 UTC

NP-MRD ID

NP0031144

Secondary Accession Numbers

None

Natural Product Identification

Common Name

epiafzelechin

Provided By

JEOL Database JEOL Logo

Description

(-)-Epiafzelechin belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4. Thus, (-)-epiafzelechin is considered to be a flavonoid (-)-Epiafzelechin is found, on average, in the highest concentration within a few different foods, such as teas (Camellia sinensis), red tea, and herbal tea and in a lower concentration in green tea and black tea (-)-Epiafzelechin has also been detected, but not quantified in, several different foods, such as mexican oreganos (Lippia graveolens), vaccinium (blueberry, cranberry, huckleberry), italian oreganos (Origanum X majoricum), butternuts (Juglans cinerea), and corns (Zea mays). This could make (-)-epiafzelechin a potential biomarker for the consumption of these foods (-)-Epiafzelechin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. epiafzelechin is found in Acacia catechu , Actinidia chinensis , Afzelia sp., Aiouea hammeliana, Artocarpus dadah, Artocarpus fretessi Hassk, Artocarpus reticulatus Miq, Bauhinia racemosa, Bergenia ligulata , Camellia sinensis , Cassia abbreviata , Cassia fistula , Cassia javanica , Cassia roxburghii, Cassia sieberiana, Cassia spp., Cassipourea gummiflua, Celastrus orbiculatus, Cochlospermum gillivraei, Crateva religiosa, Desmoncus polyacanthos , Desmoncus polycanthus, Dicranopteris pedata, Ephedra sinica , Ephedra sp., Eucalyptus calophylla, Eysenhardtia subcoriacea Pennell, Ficus cordata, Ginkgo biloba , Juniperus communis , Kandelia candel, Larix gmelinii, Larix sibirica, Nothofagus fusca, Paraburkholderia phymatum, Pelargonium reniforme, Phyllanthus emblica, Pinalia floribunda, Prunus persica , Saxifraga ligulata, Senegalia catechu, Taxus chinensis, Tsuga chinensis, Typha capensis, Typha capensis (Rohrb.) N. E. Br , Wisteria floribunda, Xanthoceras sorbifolia and Ziziphus jujuba. epiafzelechin was first documented in 2011 (PMID: 21070009). Based on a literature review a small amount of articles have been published on (-)-Epiafzelechin (PMID: 34271878) (PMID: 34068829) (PMID: 33922460) (PMID: 33842675).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100183D          

 34 36  0  0  0  0            999 V2000
   -3.1657   -3.1127    2.1017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7534   -2.1993    1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4053   -2.0111    0.8955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0286   -1.0643   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9941   -0.3010   -0.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6051    0.7213   -1.7926 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4463    1.4501   -1.3445 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115    2.3708   -2.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8285    3.3776   -1.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3357    4.3493   -2.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1300    5.3576   -2.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0449    4.3272   -3.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2419    3.3076   -4.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0589    3.2681   -5.7895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2722    2.3071   -3.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254    1.1986   -4.1893 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3448    0.0800   -3.1691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1880   -0.7743   -3.1599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3501   -0.5145   -0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7268   -1.4592    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3825   -3.5620    2.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370   -2.5871    1.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0280   -0.9274   -0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4320    1.4430   -1.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0468    3.3914   -0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2445    5.2499   -1.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4500    5.1033   -4.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3891    4.0080   -6.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6486    0.7871   -5.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942    1.6293   -4.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1904   -0.5417   -3.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5408   -0.2550   -2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1264    0.0535   -0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7765   -1.6187    0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
 17  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8 15  2  0  0  0  0
  6  5  1  0  0  0  0
 13 12  2  0  0  0  0
  5  4  2  0  0  0  0
 15 13  1  0  0  0  0
  4  3  1  0  0  0  0
 12 10  1  0  0  0  0
  3  2  2  0  0  0  0
  2 20  1  0  0  0  0
 10  9  2  0  0  0  0
 20 19  2  0  0  0  0
 19  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10 11  1  0  0  0  0
  8  7  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 16 17  1  0  0  0  0
  2  1  1  0  0  0  0
 12 27  1  0  0  0  0
  9 25  1  0  0  0  0
 16 29  1  0  0  0  0
 16 30  1  0  0  0  0
 17 31  1  6  0  0  0
  6 24  1  6  0  0  0
  4 23  1  0  0  0  0
  3 22  1  0  0  0  0
 20 34  1  0  0  0  0
 19 33  1  0  0  0  0
 11 26  1  0  0  0  0
 14 28  1  0  0  0  0
 18 32  1  0  0  0  0
  1 21  1  0  0  0  0
M  END

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -3.1657   -3.1127    2.1017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7534   -2.1993    1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4053   -2.0111    0.8955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0286   -1.0643   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9941   -0.3010   -0.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6051    0.7213   -1.7926 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4463    1.4501   -1.3445 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115    2.3708   -2.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8285    3.3776   -1.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3357    4.3493   -2.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1300    5.3576   -2.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0449    4.3272   -3.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2419    3.3076   -4.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0589    3.2681   -5.7895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2722    2.3071   -3.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254    1.1986   -4.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448    0.0800   -3.1691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1880   -0.7743   -3.1599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3501   -0.5145   -0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7268   -1.4592    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3825   -3.5620    2.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370   -2.5871    1.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0280   -0.9274   -0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4320    1.4430   -1.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0468    3.3914   -0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2445    5.2499   -1.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4500    5.1033   -4.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3891    4.0080   -6.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6486    0.7871   -5.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942    1.6293   -4.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1904   -0.5417   -3.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5408   -0.2550   -2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1264    0.0535   -0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7765   -1.6187    0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
 17  6  1  0
  6  7  1  0
  8 15  2  0
  6  5  1  0
 13 12  2  0
  5  4  2  0
 15 13  1  0
  4  3  1  0
 12 10  1  0
  3  2  2  0
  2 20  1  0
 10  9  2  0
 20 19  2  0
 19  5  1  0
  9  8  1  0
 10 11  1  0
  8  7  1  0
 13 14  1  0
 15 16  1  0
 17 18  1  0
 16 17  1  0
  2  1  1  0
 12 27  1  0
  9 25  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  6
  6 24  1  6
  4 23  1  0
  3 22  1  0
 20 34  1  0
 19 33  1  0
 11 26  1  0
 14 28  1  0
 18 32  1  0
  1 21  1  0
M  END


  Mrv1652306202100183D          

 34 36  0  0  0  0            999 V2000
   -3.1657   -3.1127    2.1017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7534   -2.1993    1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4053   -2.0111    0.8955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0286   -1.0643   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9941   -0.3010   -0.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6051    0.7213   -1.7926 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4463    1.4501   -1.3445 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115    2.3708   -2.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8285    3.3776   -1.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3357    4.3493   -2.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1300    5.3576   -2.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0449    4.3272   -3.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2419    3.3076   -4.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0589    3.2681   -5.7895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2722    2.3071   -3.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254    1.1986   -4.1893 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3448    0.0800   -3.1691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1880   -0.7743   -3.1599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3501   -0.5145   -0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7268   -1.4592    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3825   -3.5620    2.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370   -2.5871    1.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0280   -0.9274   -0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4320    1.4430   -1.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0468    3.3914   -0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2445    5.2499   -1.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4500    5.1033   -4.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3891    4.0080   -6.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6486    0.7871   -5.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942    1.6293   -4.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1904   -0.5417   -3.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5408   -0.2550   -2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1264    0.0535   -0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7765   -1.6187    0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
 17  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8 15  2  0  0  0  0
  6  5  1  0  0  0  0
 13 12  2  0  0  0  0
  5  4  2  0  0  0  0
 15 13  1  0  0  0  0
  4  3  1  0  0  0  0
 12 10  1  0  0  0  0
  3  2  2  0  0  0  0
  2 20  1  0  0  0  0
 10  9  2  0  0  0  0
 20 19  2  0  0  0  0
 19  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10 11  1  0  0  0  0
  8  7  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 16 17  1  0  0  0  0
  2  1  1  0  0  0  0
 12 27  1  0  0  0  0
  9 25  1  0  0  0  0
 16 29  1  0  0  0  0
 16 30  1  0  0  0  0
 17 31  1  6  0  0  0
  6 24  1  6  0  0  0
  4 23  1  0  0  0  0
  3 22  1  0  0  0  0
 20 34  1  0  0  0  0
 19 33  1  0  0  0  0
 11 26  1  0  0  0  0
 14 28  1  0  0  0  0
 18 32  1  0  0  0  0
  1 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031144

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])[C@@]1([H])OC2=C(C(O[H])=C([H])C(O[H])=C2[H])C([H])([H])[C@@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2/t13-,15-/m1/s1

> <INCHI_KEY>
RSYUFYQTACJFML-UKRRQHHQSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.2687

> <EXACT_MASS>
274.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.512347734652174

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
2.098672337

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.732353999322413

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.149760394668172

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2843440587393635

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
72.01880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
epiafzelechin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -3.1657   -3.1127    2.1017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7534   -2.1993    1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4053   -2.0111    0.8955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0286   -1.0643   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9941   -0.3010   -0.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6051    0.7213   -1.7926 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4463    1.4501   -1.3445 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115    2.3708   -2.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8285    3.3776   -1.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3357    4.3493   -2.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1300    5.3576   -2.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0449    4.3272   -3.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2419    3.3076   -4.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0589    3.2681   -5.7895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2722    2.3071   -3.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254    1.1986   -4.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448    0.0800   -3.1691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1880   -0.7743   -3.1599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3501   -0.5145   -0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7268   -1.4592    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3825   -3.5620    2.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370   -2.5871    1.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0280   -0.9274   -0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4320    1.4430   -1.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0468    3.3914   -0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2445    5.2499   -1.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4500    5.1033   -4.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3891    4.0080   -6.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6486    0.7871   -5.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942    1.6293   -4.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1904   -0.5417   -3.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5408   -0.2550   -2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1264    0.0535   -0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7765   -1.6187    0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
 17  6  1  0
  6  7  1  0
  8 15  2  0
  6  5  1  0
 13 12  2  0
  5  4  2  0
 15 13  1  0
  4  3  1  0
 12 10  1  0
  3  2  2  0
  2 20  1  0
 10  9  2  0
 20 19  2  0
 19  5  1  0
  9  8  1  0
 10 11  1  0
  8  7  1  0
 13 14  1  0
 15 16  1  0
 17 18  1  0
 16 17  1  0
  2  1  1  0
 12 27  1  0
  9 25  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  6
  6 24  1  6
  4 23  1  0
  3 22  1  0
 20 34  1  0
 19 33  1  0
 11 26  1  0
 14 28  1  0
 18 32  1  0
  1 21  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0      -3.166  -3.113   2.102  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.753  -2.199   1.177  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.405  -2.011   0.896  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.029  -1.064  -0.061  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.994  -0.301  -0.737  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.605   0.721  -1.793  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.446   1.450  -1.345  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.012   2.371  -2.252  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.829   3.378  -1.736  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.336   4.349  -2.591  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.130   5.358  -2.129  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.045   4.327  -3.950  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.242   3.308  -4.457  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.059   3.268  -5.790  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.272   2.307  -3.624  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.125   1.199  -4.189  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.345   0.080  -3.169  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.188  -0.774  -3.160  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.350  -0.515  -0.437  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.727  -1.459   0.519  0.00  0.00           C+0
HETATM   21  H   UNK     0      -2.382  -3.562   2.459  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.637  -2.587   1.401  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.028  -0.927  -0.280  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.432   1.443  -1.869  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.047   3.391  -0.673  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.244   5.250  -1.170  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.450   5.103  -4.591  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.389   4.008  -6.233  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.649   0.787  -5.087  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.094   1.629  -4.470  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.190  -0.542  -3.484  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.541  -0.255  -2.773  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.126   0.054  -0.945  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.777  -1.619   0.748  0.00  0.00           H+0
CONECT    1    2   21                                                       
CONECT    2    3   20    1                                                  
CONECT    3    4    2   22                                                  
CONECT    4    5    3   23                                                  
CONECT    5    6    4   19                                                  
CONECT    6   17    7    5   24                                             
CONECT    7    6    8                                                       
CONECT    8   15    9    7                                                  
CONECT    9   10    8   25                                                  
CONECT   10   12    9   11                                                  
CONECT   11   10   26                                                       
CONECT   12   13   10   27                                                  
CONECT   13   12   15   14                                                  
CONECT   14   13   28                                                       
CONECT   15    8   13   16                                                  
CONECT   16   15   17   29   30                                             
CONECT   17    6   18   16   31                                             
CONECT   18   17   32                                                       
CONECT   19   20    5   33                                                  
CONECT   20    2   19   34                                                  
CONECT   21    1                                                            
CONECT   22    3                                                            
CONECT   23    4                                                            
CONECT   24    6                                                            
CONECT   25    9                                                            
CONECT   26   11                                                            
CONECT   27   12                                                            
CONECT   28   14                                                            
CONECT   29   16                                                            
CONECT   30   16                                                            
CONECT   31   17                                                            
CONECT   32   18                                                            
CONECT   33   19                                                            
CONECT   34   20                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

RDKit          3D

34 36  0  0  0  0  0  0  0  0999 V2000
   -3.1657   -3.1127    2.1017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7534   -2.1993    1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4053   -2.0111    0.8955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0286   -1.0643   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9941   -0.3010   -0.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6051    0.7213   -1.7926 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4463    1.4501   -1.3445 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115    2.3708   -2.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8285    3.3776   -1.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3357    4.3493   -2.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1300    5.3576   -2.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0449    4.3272   -3.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2419    3.3076   -4.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0589    3.2681   -5.7895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2722    2.3071   -3.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254    1.1986   -4.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448    0.0800   -3.1691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1880   -0.7743   -3.1599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3501   -0.5145   -0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7268   -1.4592    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3825   -3.5620    2.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370   -2.5871    1.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0280   -0.9274   -0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4320    1.4430   -1.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0468    3.3914   -0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2445    5.2499   -1.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4500    5.1033   -4.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3891    4.0080   -6.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6486    0.7871   -5.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942    1.6293   -4.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1904   -0.5417   -3.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5408   -0.2550   -2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1264    0.0535   -0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7765   -1.6187    0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
 17  6  1  0
  6  7  1  0
  8 15  2  0
  6  5  1  0
 13 12  2  0
  5  4  2  0
 15 13  1  0
  4  3  1  0
 12 10  1  0
  3  2  2  0
  2 20  1  0
 10  9  2  0
 20 19  2  0
 19  5  1  0
  9  8  1  0
 10 11  1  0
  8  7  1  0
 13 14  1  0
 15 16  1  0
 17 18  1  0
 16 17  1  0
  2  1  1  0
 12 27  1  0
  9 25  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  6
  6 24  1  6
  4 23  1  0
  3 22  1  0
 20 34  1  0
 19 33  1  0
 11 26  1  0
 14 28  1  0
 18 32  1  0
  1 21  1  0
M  END

View in JSmol

Synonyms

Value	Source
(2R,3R)-Epiafzelechin	ChEBI
Epi-afzelechin	ChEBI
Epiafzelechin	HMDB

Chemical Formula

C₁₅H₁₄O₅

Average Mass

274.2687 Da

Monoisotopic Mass

274.08412 Da

IUPAC Name

(2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

epiafzelechin

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1[H])[C@@]1([H])OC2=C(C(O[H])=C([H])C(O[H])=C2[H])C([H])([H])[C@@]1([H])O[H]

InChI Identifier

InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2/t13-,15-/m1/s1

InChI Key

RSYUFYQTACJFML-UKRRQHHQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acacia catechu	Plant	KNApSAcK
Actinidia chinensis	Plant	KNApSAcK
Afzelia sp.	Plant	KNApSAcK
Aiouea hammeliana	LOTUS Database	35616633
Artocarpus dadah	LOTUS Database	35616633
Artocarpus fretessi Hassk	Plant	KNApSAcK
Artocarpus reticulatus Miq	Plant	KNApSAcK
Bauhinia racemosa	LOTUS Database	35616633
Bergenia ligulata	Plant	KNApSAcK
Camellia sinensis	Plant	KNApSAcK
Cannabis sativa	CannabisDB	Not Available
Cassia abbreviata	Plant	KNApSAcK
Cassia fistula	Plant	KNApSAcK
Cassia javanica	Plant	KNApSAcK
Cassia roxburghii	LOTUS Database	35616633
Cassia sieberiana	LOTUS Database	35616633
Cassia spp.	Plant	KNApSAcK
Cassipourea gummiflua	Plant	KNApSAcK
Celastrus orbiculatus	LOTUS Database	35616633
Cochlospermum gillivraei	Plant	KNApSAcK
Crateva religiosa	LOTUS Database	35616633
Desmoncus polyacanthos	Plant	KNApSAcK
Desmoncus polycanthus	Plant	KNApSAcK
Dicranopteris pedata	Plant	KNApSAcK
Ephedra sinica	Plant	KNApSAcK
Ephedra sp.	Plant	KNApSAcK
Eucalyptus calophylla	Plant	KNApSAcK
Eysenhardtia subcoriacea Pennell	Plant	KNApSAcK
Ficus cordata	Plant	KNApSAcK
Ginkgo biloba	Plant	KNApSAcK
Juniperus communis	Plant	KNApSAcK
Kandelia candel	Plant	KNApSAcK
Larix gmelini	Plant	KNApSAcK
Larix sibirica	Plant	KNApSAcK
Nothofagus fusca	Plant	KNApSAcK
Paraburkholderia phymatum	-	KNApSAcK
Pelargonium reniforme	Plant	KNApSAcK
Phyllanthus emblica	LOTUS Database	35616633
Pinalia floribunda	LOTUS Database	35616633
Prunus persica	Plant	KNApSAcK
Saxifraga ligulata	Plant	KNApSAcK
Senegalia catechu	LOTUS Database	35616633
Stellera chamaejasme	KNApSAcK Database	22123792
Taxus chinensis	Plant	KNApSAcK
Tsuga chinensis	LOTUS Database	35616633
Typha capensis	LOTUS Database	35616633
Typha capensis (Rohrb.) N. E. Br	Plant	KNApSAcK
Wisteria floribunda	LOTUS Database	35616633
Xanthoceras sorbifolium	Plant	KNApSAcK
Ziziphus jujuba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavan-3-ols

Alternative Parents

Substituents

3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
1-benzopyran
Chromane
Benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

catechin (CHEBI:31028 )
Flavan 3-ols (C12128 )
Flavans, Flavanols and Leucoanthocyanidins (LMPK12020036 )

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	1.29	ALOGPS
logP	2.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.15	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.02 m³·mol⁻¹	ChemAxon
Polarizability	27.51 Å³	ChemAxon
Number of Rings	3	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

HMDB0030822

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443639

PDB ID

Not Available

ChEBI ID

31028

Good Scents ID

rw1388821

References

General References

Kpegba K, Agbonon A, Petrovic AG, Amouzou E, Gbeassor M, Proni G, Nesnas N: Epiafzelechin from the root bark of Cassia sieberiana: detection by DART mass spectrometry, spectroscopic characterization, and antioxidant properties. J Nat Prod. 2011 Mar 25;74(3):455-9. doi: 10.1021/np100090e. Epub 2010 Nov 11. [PubMed:21070009 ]
Wang X, Yan M, Zhou J, Song W, Xiao Y, Cui C, Gao W, Ke F, Zhu J, Gu Z, Hou R: Delivery of acetamiprid to tea leaves enabled by porous silica nanoparticles: efficiency, distribution and metabolism of acetamiprid in tea plants. BMC Plant Biol. 2021 Jul 16;21(1):337. doi: 10.1186/s12870-021-03120-4. [PubMed:34271878 ]
Zheng Y, Yang XW, Schols D, Mori M, Botta B, Chevigne A, Mulinge M, Steinmetz A, Schmit JC, Seguin-Devaux C: Active Components from Cassia abbreviata Prevent HIV-1 Entry by Distinct Mechanisms of Action. Int J Mol Sci. 2021 May 10;22(9). pii: ijms22095052. doi: 10.3390/ijms22095052. [PubMed:34068829 ]
Yang X, He Z, Zheng Y, Wang N, Mulinge M, Schmit JC, Steinmetz A, Seguin-Devaux C: Chemical Constituents of Cassia abbreviata and Their Anti-HIV-1 Activity. Molecules. 2021 Apr 23;26(9). pii: molecules26092455. doi: 10.3390/molecules26092455. [PubMed:33922460 ]
Dey D, Dey N, Ghosh S, Chandrasekaran N, Mukherjee A, Thomas J: Potential combination therapy using twenty phytochemicals from twenty plants to prevent SARS- CoV-2 infection: An in silico Approach. Virusdisease. 2021 Apr 5:1-9. doi: 10.1007/s13337-021-00658-7. [PubMed:33842675 ]
Davis, A. L., et al. (1996). Davis, A. L., et al, Magn. Reson. Chem. 34, 887 (1996). Mag. Reson. Chem..

Showing NP-Card for epiafzelechin (NP0031144)

MOL for NP0031144 (epiafzelechin)

3D MOL for NP0031144 (epiafzelechin)

3D SDF for NP0031144 (epiafzelechin)

3D-SDF for NP0031144 (epiafzelechin)

PDB for NP0031144 (epiafzelechin)

3D PDB for NP0031144 (epiafzelechin)

SMILES for NP0031144 (epiafzelechin)

INCHI for NP0031144 (epiafzelechin)

Structure for NP0031144 (epiafzelechin)

3D Structure for NP0031144 (epiafzelechin)