NP-MRD: Showing NP-Card for Oenothein B (NP0074281)

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Record Information

Version

2.0

Created at

2022-04-28 19:26:30 UTC

Updated at

2022-04-28 19:26:30 UTC

NP-MRD ID

NP0074281

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oenothein B

Description

(11R,12S,13S,35S,36R,37S,38R,60R)-11,35-diformyl-4,5,6,18,19,20,28,29,30,38,44,45,46,49,50,55,56,60-octadecahydroxy-9,15,33,41,53,57-hexaoxo-36-(3,4,5-trihydroxybenzoyloxy)-2,10,14,26,34,40,54,58-octaoxanonacyclo[35.13.4.4¹³,²³.2²²,²⁵.0³,⁸.0¹⁶,²¹.0²⁷,³².0⁴²,⁴⁷.0⁴⁸,⁵²]Hexaconta-1(50),3,5,7,16,18,20,22(56),23,25(55),27,29,31,42,44,46,48,51-octadecaen-12-yl 3,4,5-trihydroxybenzoate belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Oenothein B is found in Chamaenerion angustifolium, Cuphea hyssopifolia, Oenothera biennis , Oenothera erythrosepara , Oenothera tetraptera and Punica granatum . Based on a literature review very few articles have been published on (11R,12S,13S,35S,36R,37S,38R,60R)-11,35-diformyl-4,5,6,18,19,20,28,29,30,38,44,45,46,49,50,55,56,60-octadecahydroxy-9,15,33,41,53,57-hexaoxo-36-(3,4,5-trihydroxybenzoyloxy)-2,10,14,26,34,40,54,58-octaoxanonacyclo[35.13.4.4¹³,²³.2²²,²⁵.0³,⁸.0¹⁶,²¹.0²⁷,³².0⁴²,⁴⁷.0⁴⁸,⁵²]Hexaconta-1(50),3,5,7,16,18,20,22(56),23,25(55),27,29,31,42,44,46,48,51-octadecaen-12-yl 3,4,5-trihydroxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221262D          

112122  0  0  1  0            999 V2000
   17.4609    1.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1033    0.6845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5736   -0.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0261    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8497    0.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2209   -0.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7684   -0.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9448   -0.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9152   -1.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6792   -2.0571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2221   -2.0577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4047   -1.8032    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.5775   -1.5783    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7763   -1.8880    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2794   -1.1625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6115   -0.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7227   -0.5869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9224   -0.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2760   -0.3376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4376   -1.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6324   -1.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9658   -1.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2145   -1.3201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9840   -0.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9953    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3912    1.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7058    1.6621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1463    1.4642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9800    1.2675    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.7489    0.9525    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5705    1.1489    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3893    0.8856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2214    1.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7994    0.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0028    1.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1356    2.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7207    3.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5262    3.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7745    3.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2173    4.5787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5030    5.4160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4118    4.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1635    3.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3929    3.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4443    4.9075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6292    3.6460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4320    2.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5068    1.9952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3597    2.1023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3118    4.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3335    3.5646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9218    2.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5668    2.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3975    2.3139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7200    2.8864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6739    0.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9423    1.7758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2190    2.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2574    2.5467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8749    3.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3717    3.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6863    4.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5041    4.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0073    4.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6927    3.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8822    4.2225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4469    5.5408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1793    5.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6075    2.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3893    3.0840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2866    0.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5665    0.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5552   -0.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2639   -0.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7423   -1.5887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7484   -0.7812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7491    0.6421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1603   -2.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.5959   -2.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3610   -2.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0750   -3.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0741   -3.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3592   -4.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6452   -3.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6461   -3.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9840   -3.7635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2672   -4.8002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1500   -5.2744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9689   -3.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6534   -4.1478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5971   -2.7221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2078   -3.4595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3322   -2.9347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0805   -0.8969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6336   -2.3187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0033   -2.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1598   -2.3314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9705   -3.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7053   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7479   -4.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0556   -5.3227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3208   -4.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2782   -4.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9798   -5.7617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1754   -6.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4219   -5.4285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9027   -2.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4958   -3.3264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0825   -0.1883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6017    1.0642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4593    1.4304    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
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 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
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 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
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  4112  1  0  0  0  0
M  END

     RDKit          3D

160170  0  0  0  0  0  0  0  0999 V2000
   -0.7112   -1.2780    1.5857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4844   -0.9644    0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4266   -1.8701   -0.0054 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0893   -3.1829    0.2450 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9982   -5.3060    1.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3466   -5.3635    1.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7564   -6.1396    2.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1028   -6.1588    3.2124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8154   -6.8842    3.5113 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7494   -4.1984    1.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282221262D          

112122  0  0  1  0            999 V2000
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    9.9953    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3912    1.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7058    1.6621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1463    1.4642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   16.5262    3.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.3929    3.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.9423    1.7758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   14.0073    4.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0074281

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1COC(=O)C2=CC(O)=C(O)C(O)=C2C2=C(O)C(O)=C3OC4=C(O)C(O)=C(O)C=C4C(=O)O[C@@H](C=O)[C@@H](OC(=O)C4=CC(O)=C(O)C(O)=C4)[C@H]4OC(=O)C5=C(C(O)=C(O)C(O)=C5)C5=C(O)C(O)=C(OC6=C(C=C(O)C(O)=C6O)C(=O)O[C@H](C=O)[C@H](OC(=O)C6=CC(O)=C(O)C(O)=C6)[C@H]1OC(=O)C2=C3)C=C5C(=O)OC[C@H]4O

> <INCHI_IDENTIFIER>
InChI=1S/C68H48O44/c69-11-35-59(111-61(95)15-1-23(71)41(81)24(72)2-15)57-32(80)14-104-64(98)19-9-33(47(87)51(91)39(19)38-18(65(99)109-57)6-28(76)44(84)50(38)90)105-55-21(7-29(77)45(85)53(55)93)67(101)108-36(12-70)60(112-62(96)16-3-25(73)42(82)26(74)4-16)58-31(79)13-103-63(97)17-5-27(75)43(83)49(89)37(17)40-20(66(100)110-58)10-34(48(88)52(40)92)106-56-22(68(102)107-35)8-30(78)46(86)54(56)94/h1-12,31-32,35-36,57-60,71-94H,13-14H2/t31-,32-,35+,36-,57+,58+,59-,60+/m1/s1

> <INCHI_KEY>
MGFJAOIDAUFIHI-AQTHVLBGSA-N

> <FORMULA>
C68H48O44

> <MOLECULAR_WEIGHT>
1569.088

> <EXACT_MASS>
1568.151844826

> <JCHEM_ACCEPTOR_COUNT>
34

> <JCHEM_ATOM_COUNT>
160

> <JCHEM_AVERAGE_POLARIZABILITY>
136.66122272972882

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
24

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(11R,12S,13S,35S,36R,37S,38R,60R)-11,35-diformyl-4,5,6,18,19,20,28,29,30,38,44,45,46,49,50,55,56,60-octadecahydroxy-9,15,33,41,53,57-hexaoxo-12-(3,4,5-trihydroxybenzoyloxy)-2,10,14,26,34,40,54,58-octaoxanonacyclo[35.13.4.4^{13,23}.2^{22,25}.0^{3,8}.0^{16,21}.0^{27,32}.0^{42,47}.0^{48,52}]hexaconta-1(50),3,5,7,16(21),17,19,22(56),23,25(55),27(32),28,30,42,44,46,48,51-octadecaen-36-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
3.749282412666666

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
11

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
6.824255982177115

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.31799243852381

> <JCHEM_PKA_STRONGEST_BASIC>
-5.910969331729064

> <JCHEM_POLAR_SURFACE_AREA>
748.5200000000004

> <JCHEM_REFRACTIVITY>
355.36899999999974

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(11R,12S,13S,35S,36R,37S,38R,60R)-11,35-diformyl-4,5,6,18,19,20,28,29,30,38,44,45,46,49,50,55,56,60-octadecahydroxy-9,15,33,41,53,57-hexaoxo-12-(3,4,5-trihydroxybenzoyloxy)-2,10,14,26,34,40,54,58-octaoxanonacyclo[35.13.4.4^{13,23}.2^{22,25}.0^{3,8}.0^{16,21}.0^{27,32}.0^{42,47}.0^{48,52}]hexaconta-1(50),3,5,7,16(21),17,19,22(56),23,25(55),27(32),28,30,42,44,46,48,51-octadecaen-36-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      32.594   2.242   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      33.793   1.278   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      34.671  -0.040   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      35.515   1.247   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      37.053   1.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      37.746  -0.215   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      36.901  -1.503   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      35.364  -1.416   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.308  -3.037   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      36.734  -3.840   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      34.015  -3.841   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      32.489  -3.366   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.945  -2.946   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.449  -3.524   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.522  -2.170   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.275  -1.265   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      25.616  -1.095   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      24.122  -1.582   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      22.915  -0.630   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      23.217  -2.878   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.714  -2.349   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.469  -3.335   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      19.067  -2.464   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      18.637  -0.916   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.658   0.624   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.397   2.056   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      18.117   3.103   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      20.806   2.733   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      22.363   2.366   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      23.798   1.778   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      25.332   2.145   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      26.860   1.653   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      28.413   1.995   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      29.492   0.988   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      29.872   2.631   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      30.120   4.181   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      29.345   5.610   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      30.849   5.943   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      31.312   7.411   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      30.272   8.547   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      30.806  10.110   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      28.769   8.214   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      28.305   6.745   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      26.867   7.415   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      26.963   9.161   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      25.441   6.806   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      25.073   5.286   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      25.213   3.724   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      26.805   3.924   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      32.315   8.735   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      32.356   6.654   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      31.587   4.743   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      32.791   3.781   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      34.342   4.319   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      33.077   5.388   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      31.125   1.706   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      24.159   3.315   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      22.809   4.520   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      21.014   4.754   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      24.033   5.846   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      23.094   7.066   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      23.681   8.490   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      25.208   8.693   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      26.147   7.473   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      25.560   6.049   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0      27.780   7.882   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      25.101  10.343   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0      22.735   9.832   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0      21.667   3.954   0.000  0.00  0.00           C+0
HETATM   70  O   UNK     0      21.260   5.757   0.000  0.00  0.00           O+0
HETATM   71  C   UNK     0      17.335   1.412   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      15.991   0.660   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      15.970  -0.879   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      17.293  -1.668   0.000  0.00  0.00           C+0
HETATM   75  O   UNK     0      16.319  -2.966   0.000  0.00  0.00           O+0
HETATM   76  O   UNK     0      14.464  -1.458   0.000  0.00  0.00           O+0
HETATM   77  O   UNK     0      14.465   1.199   0.000  0.00  0.00           O+0
HETATM   78  C   UNK     0      20.833  -4.949   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      22.266  -5.448   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      23.512  -4.457   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      24.941  -5.150   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      26.273  -5.921   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0      26.272  -7.461   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0      24.937  -8.230   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0      23.604  -7.459   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0      23.606  -5.919   0.000  0.00  0.00           C+0
HETATM   87  O   UNK     0      22.370  -7.025   0.000  0.00  0.00           O+0
HETATM   88  O   UNK     0      22.899  -8.960   0.000  0.00  0.00           O+0
HETATM   89  O   UNK     0      24.547  -9.846   0.000  0.00  0.00           O+0
HETATM   90  C   UNK     0      27.942  -6.020   0.000  0.00  0.00           C+0
HETATM   91  O   UNK     0      27.353  -7.742   0.000  0.00  0.00           O+0
HETATM   92  O   UNK     0      29.115  -5.081   0.000  0.00  0.00           O+0
HETATM   93  O   UNK     0      20.921  -6.458   0.000  0.00  0.00           O+0
HETATM   94  O   UNK     0      19.287  -5.478   0.000  0.00  0.00           O+0
HETATM   95  O   UNK     0      30.017  -1.674   0.000  0.00  0.00           O+0
HETATM   96  O   UNK     0      31.049  -4.328   0.000  0.00  0.00           O+0
HETATM   97  C   UNK     0      29.873  -5.212   0.000  0.00  0.00           C+0
HETATM   98  O   UNK     0      28.298  -4.352   0.000  0.00  0.00           O+0
HETATM   99  C   UNK     0      29.812  -6.860   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0      31.183  -7.560   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0      31.263  -9.098   0.000  0.00  0.00           C+0
HETATM  102  C   UNK     0      29.971  -9.936   0.000  0.00  0.00           C+0
HETATM  103  C   UNK     0      28.599  -9.236   0.000  0.00  0.00           C+0
HETATM  104  C   UNK     0      28.519  -7.698   0.000  0.00  0.00           C+0
HETATM  105  O   UNK     0      27.962 -10.755   0.000  0.00  0.00           O+0
HETATM  106  O   UNK     0      30.194 -11.534   0.000  0.00  0.00           O+0
HETATM  107  O   UNK     0      32.521 -10.133   0.000  0.00  0.00           O+0
HETATM  108  C   UNK     0      33.418  -4.940   0.000  0.00  0.00           C+0
HETATM  109  O   UNK     0      34.526  -6.209   0.000  0.00  0.00           O+0
HETATM  110  O   UNK     0      39.354  -0.351   0.000  0.00  0.00           O+0
HETATM  111  O   UNK     0      38.457   1.987   0.000  0.00  0.00           O+0
HETATM  112  O   UNK     0      36.324   2.670   0.000  0.00  0.00           O+0
CONECT    1    2   53   56                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5  112                                                  
CONECT    5    4    6  111                                                  
CONECT    6    5    7  110                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13  108                                                  
CONECT   13   12   14   96                                                  
CONECT   14   13   15   92                                                  
CONECT   15   14   16   95                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   80                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   78                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   74                                                  
CONECT   25   24   26   71                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   69                                                  
CONECT   30   29   31   57                                                  
CONECT   31   30   32   48                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   56                                                  
CONECT   36   35   37   52                                                  
CONECT   37   36   38   43                                                  
CONECT   38   37   39   51                                                  
CONECT   39   38   40   50                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   37   44                                                  
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   31   49                                                  
CONECT   49   48                                                            
CONECT   50   39                                                            
CONECT   51   38                                                            
CONECT   52   36   53   55                                                  
CONECT   53   52    1   54                                                  
CONECT   54   53                                                            
CONECT   55   52                                                            
CONECT   56   35    1                                                       
CONECT   57   30   58                                                       
CONECT   58   57   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   61   65                                                  
CONECT   61   60   62                                                       
CONECT   62   61   63   68                                                  
CONECT   63   62   64   67                                                  
CONECT   64   63   65   66                                                  
CONECT   65   64   60                                                       
CONECT   66   64                                                            
CONECT   67   63                                                            
CONECT   68   62                                                            
CONECT   69   29   70                                                       
CONECT   70   69                                                            
CONECT   71   25   72                                                       
CONECT   72   71   73   77                                                  
CONECT   73   72   74   76                                                  
CONECT   74   73   24   75                                                  
CONECT   75   74                                                            
CONECT   76   73                                                            
CONECT   77   72                                                            
CONECT   78   22   79   94                                                  
CONECT   79   78   80   93                                                  
CONECT   80   79   20   81                                                  
CONECT   81   80   82   86                                                  
CONECT   82   81   83   90                                                  
CONECT   83   82   84                                                       
CONECT   84   83   85   89                                                  
CONECT   85   84   86   88                                                  
CONECT   86   85   81   87                                                  
CONECT   87   86                                                            
CONECT   88   85                                                            
CONECT   89   84                                                            
CONECT   90   82   91   92                                                  
CONECT   91   90                                                            
CONECT   92   90   14                                                       
CONECT   93   79                                                            
CONECT   94   78                                                            
CONECT   95   15                                                            
CONECT   96   13   97                                                       
CONECT   97   96   98   99                                                  
CONECT   98   97                                                            
CONECT   99   97  100  104                                                  
CONECT  100   99  101                                                       
CONECT  101  100  102  107                                                  
CONECT  102  101  103  106                                                  
CONECT  103  102  104  105                                                  
CONECT  104  103   99                                                       
CONECT  105  103                                                            
CONECT  106  102                                                            
CONECT  107  101                                                            
CONECT  108   12  109                                                       
CONECT  109  108                                                            
CONECT  110    6                                                            
CONECT  111    5                                                            
CONECT  112    4                                                            
MASTER        0    0    0    0    0    0    0    0  112    0  244    0
END

View in JSmol

Synonyms

Value	Source
(11R,12S,13S,35S,36R,37S,38R,60R)-11,35-Diformyl-4,5,6,18,19,20,28,29,30,38,44,45,46,49,50,55,56,60-octadecahydroxy-9,15,33,41,53,57-hexaoxo-36-(3,4,5-trihydroxybenzoyloxy)-2,10,14,26,34,40,54,58-octaoxanonacyclo[35.13.4.4,.2,.0,.0,.0,.0,.0,]hexaconta-1(50),3,5,7,16,18,20,22(56),23,25(55),27,29,31,42,44,46,48,51-octadecaen-12-yl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₆₈H₄₈O₄₄

Average Mass

1569.0880 Da

Monoisotopic Mass

1568.15184 Da

IUPAC Name

(11R,12S,13S,35S,36R,37S,38R,60R)-11,35-diformyl-4,5,6,18,19,20,28,29,30,38,44,45,46,49,50,55,56,60-octadecahydroxy-9,15,33,41,53,57-hexaoxo-12-(3,4,5-trihydroxybenzoyloxy)-2,10,14,26,34,40,54,58-octaoxanonacyclo[35.13.4.4^{13,23}.2^{22,25}.0^{3,8}.0^{16,21}.0^{27,32}.0^{42,47}.0^{48,52}]hexaconta-1(50),3,5,7,16(21),17,19,22(56),23,25(55),27(32),28,30,42,44,46,48,51-octadecaen-36-yl 3,4,5-trihydroxybenzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

O[C@@H]1COC(=O)C2=CC(O)=C(O)C(O)=C2C2=C(O)C(O)=C3OC4=C(O)C(O)=C(O)C=C4C(=O)O[C@@H](C=O)[C@@H](OC(=O)C4=CC(O)=C(O)C(O)=C4)[C@H]4OC(=O)C5=C(C(O)=C(O)C(O)=C5)C5=C(O)C(O)=C(OC6=C(C=C(O)C(O)=C6O)C(=O)O[C@H](C=O)[C@H](OC(=O)C6=CC(O)=C(O)C(O)=C6)[C@H]1OC(=O)C2=C3)C=C5C(=O)OC[C@H]4O

InChI Identifier

InChI=1S/C68H48O44/c69-11-35-59(111-61(95)15-1-23(71)41(81)24(72)2-15)57-32(80)14-104-64(98)19-9-33(47(87)51(91)39(19)38-18(65(99)109-57)6-28(76)44(84)50(38)90)105-55-21(7-29(77)45(85)53(55)93)67(101)108-36(12-70)60(112-62(96)16-3-25(73)42(82)26(74)4-16)58-31(79)13-103-63(97)17-5-27(75)43(83)49(89)37(17)40-20(66(100)110-58)10-34(48(88)52(40)92)106-56-22(68(102)107-35)8-30(78)46(86)54(56)94/h1-12,31-32,35-36,57-60,71-94H,13-14H2/t31-,32-,35+,36-,57+,58+,59-,60+/m1/s1

InChI Key

MGFJAOIDAUFIHI-AQTHVLBGSA-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
Chamerion angustifolium	-	KNApSAcK
Cuphea hyssopifolia	Plant	KNApSAcK
Oenothera biennis	Plant	KNApSAcK
Oenothera erythrosepara	Plant	KNApSAcK
Oenothera tetraptera	Plant	KNApSAcK
Punica granatum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Diaryl ether
Benzoate ester
Pyrogallol derivative
Benzoic acid or derivatives
Benzenetriol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
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	3.6	ALOGPS
logP	3.75	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	6.32	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	34	ChemAxon
Hydrogen Donor Count	24	ChemAxon
Polar Surface Area	748.52 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	355.37 m³·mol⁻¹	ChemAxon
Polarizability	136.66 Å³	ChemAxon
Number of Rings	11	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

159557814

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Oenothein B (NP0074281)

MOL for NP0074281 (Oenothein B)

3D MOL for NP0074281 (Oenothein B)

3D SDF for NP0074281 (Oenothein B)

3D-SDF for NP0074281 (Oenothein B)

PDB for NP0074281 (Oenothein B)

3D PDB for NP0074281 (Oenothein B)

SMILES for NP0074281 (Oenothein B)

INCHI for NP0074281 (Oenothein B)

Structure for NP0074281 (Oenothein B)

3D Structure for NP0074281 (Oenothein B)