NP-MRD: Showing NP-Card for Gemin C (NP0074255)

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Record Information

Version

2.0

Created at

2022-04-28 19:24:39 UTC

Updated at

2022-04-28 19:24:39 UTC

NP-MRD ID

NP0074255

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gemin C

Description

(1R,2S,19S,20R,22R)-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0²,¹⁹.0⁵,¹⁰.0¹¹,¹⁶.0²⁶,³¹.0³²,³⁷]Nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-20-yl 2-[2,3-dihydroxy-5-({[(2S,3R,4R,5S,6S)-5-hydroxy-6-(hydroxymethyl)-3,4-bis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)phenoxy]-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. Gemin C is found in Geum japonicum . Based on a literature review very few articles have been published on (1R,2S,19S,20R,22R)-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0²,¹⁹.0⁵,¹⁰.0¹¹,¹⁶.0²⁶,³¹.0³²,³⁷]Nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-20-yl 2-[2,3-dihydroxy-5-({[(2S,3R,4R,5S,6S)-5-hydroxy-6-(hydroxymethyl)-3,4-bis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4,5-trihydroxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221242D          

112123  0  0  1  0            999 V2000
    7.6559    0.9854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1671    1.6499    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4982    2.4056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2490    2.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4639    1.9012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6493    3.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4693    3.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9581    2.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6270    1.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8070    1.8321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3182    2.4966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4759    1.0764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1158    1.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9358    1.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2669    2.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7780    2.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1092    3.5254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0868    2.1963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4246    0.6850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8004    4.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3115    4.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4916    4.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1605    3.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0027    5.3371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6427    5.5192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6203    4.1900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3471    1.5589    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0160    0.8032    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5049    0.1387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3248    0.2297    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8137   -0.4349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4825   -1.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6626   -1.2815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9714   -1.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6403   -2.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1291   -3.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6059   -3.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2802   -2.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7913   -1.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1001   -2.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7352   -3.4345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7980   -4.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8203   -2.7018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4892   -3.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6692   -3.5485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3381   -4.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8269   -4.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6469   -4.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9780   -4.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1357   -5.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9557   -5.4511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8046   -6.2978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2935   -6.9624    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1134   -6.8713    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6022   -7.5359    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2711   -8.2915    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4512   -8.3826    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9623   -7.7180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1201   -9.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3001   -9.2293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7600   -8.9561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4222   -7.4448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9110   -8.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5799   -8.8651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7310   -8.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0621   -7.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8821   -7.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3709   -7.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0398   -8.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2198   -8.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5286   -9.2565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1909   -7.7452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2132   -6.4160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4445   -6.1157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2645   -6.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7533   -6.6892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5956   -5.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1068   -4.6044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4379   -3.8488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2578   -3.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7467   -4.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4156   -5.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5666   -4.3312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5890   -3.0021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9490   -3.1842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181   -4.3951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1804   -2.8839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3289    0.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5040    0.3339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8032    0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1881    0.2194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4490    1.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5538    2.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0844    2.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8723    3.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6674    2.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1027    3.6895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2172    2.3736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0544    4.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4487    4.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6607    4.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4786    3.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6907    3.2798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0550    4.8890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6308    5.3782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8975    2.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1364    2.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0316    1.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6879    1.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2705    1.3774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4802    3.0140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2971    3.3983    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  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  1 12  1  6  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 14 19  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  6 23  1  0  0  0  0
 22 24  1  0  0  0  0
 21 25  1  0  0  0  0
 20 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
  1 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
 38 40  1  0  0  0  0
 37 41  1  0  0  0  0
 36 42  1  0  0  0  0
 35 43  1  0  0  0  0
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107111  1  0  0  0  0
106112  1  0  0  0  0
M  END

     RDKit          3D

162173  0  0  0  0  0  0  0  0999 V2000
    4.1649   -0.7678    2.2067 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3646    0.1486    1.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5774    0.7652    1.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6508    0.6227    2.2604 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2713    1.8726    2.4205 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4580    2.4225    1.1492 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0533    3.7866    1.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2407    4.2675   -0.0680 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1743    1.5864    0.1487 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7940    2.0700   -1.1279 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8323    0.1246    0.1677 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8632   -0.6317   -0.4414 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5412   -1.6697   -1.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3396   -1.9031   -1.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5380   -2.5065   -1.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1937   -3.5672   -2.7661 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1519   -4.3912   -3.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8106   -5.4463   -4.1624 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4946   -4.1582   -3.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4654   -4.9841   -3.6743 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282221242D          

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M  END
> <DATABASE_ID>
NP0074255

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H]1O[C@@H](OC(=O)C2=CC(OC3=C(C=C(O)C(O)=C3O)C(=O)O[C@H]3O[C@@H]4COC(=O)C5=C(C(O)=C(O)C(O)=C5)C5=C(C=C(O)C(O)=C5O)C(=O)O[C@H]4[C@@H]4OC(=O)C5=C(C(O)=C(O)C(O)=C5)C5=C(C=C(O)C(O)=C5O)C(=O)O[C@H]34)=C(O)C(O)=C2)[C@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C68H50O44/c69-12-33-47(88)55(107-59(94)14-1-22(70)39(80)23(71)2-14)57(109-60(95)15-3-24(72)40(81)25(73)4-15)67(104-33)111-61(96)16-5-26(74)41(82)32(6-16)103-53-21(11-31(79)46(87)52(53)93)66(101)112-68-58-56(108-64(99)19-9-29(77)44(85)50(91)37(19)38-20(65(100)110-58)10-30(78)45(86)51(38)92)54-34(105-68)13-102-62(97)17-7-27(75)42(83)48(89)35(17)36-18(63(98)106-54)8-28(76)43(84)49(36)90/h1-11,33-34,47,54-58,67-93H,12-13H2/t33-,34+,47-,54+,55+,56-,57+,58-,67-,68+/m0/s1

> <INCHI_KEY>
YKLNPEYKZHHXKJ-QRFSJKBVSA-N

> <FORMULA>
C68H50O44

> <MOLECULAR_WEIGHT>
1571.104

> <EXACT_MASS>
1570.16749489

> <JCHEM_ACCEPTOR_COUNT>
35

> <JCHEM_ATOM_COUNT>
162

> <JCHEM_AVERAGE_POLARIZABILITY>
139.78312198947435

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
25

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,19S,20R,22R)-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0^{2,19}.0^{5,10}.0^{11,16}.0^{26,31}.0^{32,37}]nonatriaconta-5(10),6,8,11(16),12,14,26(31),27,29,32(37),33,35-dodecaen-20-yl 2-[2,3-dihydroxy-5-({[(2S,3R,4R,5S,6S)-5-hydroxy-6-(hydroxymethyl)-3,4-bis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
3.87

> <JCHEM_LOGP>
5.190318413999998

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
12

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
7.247865087787383

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.901818787872661

> <JCHEM_PKA_STRONGEST_BASIC>
-5.9111147575630385

> <JCHEM_POLAR_SURFACE_AREA>
743.8400000000004

> <JCHEM_REFRACTIVITY>
354.3226999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,19S,20R,22R)-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0^{2,19}.0^{5,10}.0^{11,16}.0^{26,31}.0^{32,37}]nonatriaconta-5(10),6,8,11(16),12,14,26(31),27,29,32(37),33,35-dodecaen-20-yl 2-[2,3-dihydroxy-5-({[(2S,3R,4R,5S,6S)-5-hydroxy-6-(hydroxymethyl)-3,4-bis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)phenoxy]-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      14.291   1.839   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.379   3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.997   4.490   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      15.398   4.020   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      15.799   3.549   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      16.145   6.071   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.676   6.241   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.588   5.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.970   3.590   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.440   3.420   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      15.527   4.660   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      15.822   2.009   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      18.883   2.349   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.413   2.519   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.032   3.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.119   5.170   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      20.737   6.581   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      22.562   4.100   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      21.326   1.279   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      18.294   7.651   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.382   8.892   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.851   8.722   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.233   7.311   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.938   9.962   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      18.000  10.302   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      19.825   7.821   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.848   2.910   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.230   1.499   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.142   0.259   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      13.673   0.429   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.585  -0.812   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      13.967  -2.222   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.437  -2.392   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.880  -3.463   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.262  -4.873   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      15.174  -6.114   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      16.064  -5.815   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      17.323  -4.533   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      16.410  -3.293   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      18.854  -4.363   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      18.172  -6.411   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      14.556  -7.524   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      12.731  -5.043   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      12.113  -6.454   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      10.583  -6.624   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       9.964  -8.034   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      10.877  -9.275   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      12.408  -9.105   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      13.026  -7.694   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      13.320 -10.345   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      14.851 -10.175   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      12.702 -11.756   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      13.614 -12.996   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      15.145 -12.826   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      16.058 -14.067   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      15.439 -15.478   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      13.909 -15.648   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      12.996 -14.407   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      13.291 -17.058   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      11.760 -17.228   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      16.352 -16.718   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      17.588 -13.897   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0      18.501 -15.138   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0      17.883 -16.548   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0      20.031 -14.968   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      20.649 -13.557   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      22.180 -13.387   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      23.092 -14.628   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      22.474 -16.038   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      20.944 -16.208   0.000  0.00  0.00           C+0
HETATM   71  O   UNK     0      23.387 -17.279   0.000  0.00  0.00           O+0
HETATM   72  O   UNK     0      24.623 -14.458   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0      22.798 -11.977   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0      15.763 -11.416   0.000  0.00  0.00           O+0
HETATM   75  C   UNK     0      17.294 -11.246   0.000  0.00  0.00           C+0
HETATM   76  O   UNK     0      18.206 -12.487   0.000  0.00  0.00           O+0
HETATM   77  C   UNK     0      17.912  -9.835   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      16.999  -8.595   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      17.617  -7.184   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      19.148  -7.014   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      20.060  -8.255   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      19.442  -9.665   0.000  0.00  0.00           C+0
HETATM   83  O   UNK     0      21.591  -8.085   0.000  0.00  0.00           O+0
HETATM   84  O   UNK     0      19.766  -5.604   0.000  0.00  0.00           O+0
HETATM   85  O   UNK     0      16.705  -5.944   0.000  0.00  0.00           O+0
HETATM   86  O   UNK     0       8.434  -8.204   0.000  0.00  0.00           O+0
HETATM   87  O   UNK     0       9.670  -5.383   0.000  0.00  0.00           O+0
HETATM   88  C   UNK     0       9.947   0.647   0.000  0.00  0.00           C+0
HETATM   89  O   UNK     0       8.408   0.623   0.000  0.00  0.00           O+0
HETATM   90  C   UNK     0       7.099   1.436   0.000  0.00  0.00           C+0
HETATM   91  O   UNK     0       5.951   0.409   0.000  0.00  0.00           O+0
HETATM   92  C   UNK     0       6.438   2.827   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0       6.634   4.354   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0       7.624   5.533   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0       9.095   5.990   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0      10.579   5.579   0.000  0.00  0.00           C+0
HETATM   97  O   UNK     0      11.392   6.887   0.000  0.00  0.00           O+0
HETATM   98  O   UNK     0      11.605   4.431   0.000  0.00  0.00           O+0
HETATM   99  C   UNK     0       9.435   7.492   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0       8.304   8.537   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0       6.833   8.081   0.000  0.00  0.00           C+0
HETATM  102  C   UNK     0       6.493   6.579   0.000  0.00  0.00           C+0
HETATM  103  O   UNK     0       5.023   6.122   0.000  0.00  0.00           O+0
HETATM  104  O   UNK     0       5.703   9.126   0.000  0.00  0.00           O+0
HETATM  105  O   UNK     0       8.644  10.039   0.000  0.00  0.00           O+0
HETATM  106  C   UNK     0       5.409   5.287   0.000  0.00  0.00           C+0
HETATM  107  C   UNK     0       3.988   4.693   0.000  0.00  0.00           C+0
HETATM  108  C   UNK     0       3.792   3.165   0.000  0.00  0.00           C+0
HETATM  109  C   UNK     0       5.017   2.232   0.000  0.00  0.00           C+0
HETATM  110  O   UNK     0       2.372   2.571   0.000  0.00  0.00           O+0
HETATM  111  O   UNK     0       2.763   5.626   0.000  0.00  0.00           O+0
HETATM  112  O   UNK     0       4.288   6.343   0.000  0.00  0.00           O+0
CONECT    1    2   12   30                                                  
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   23                                                  
CONECT    7    6    8   20                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    1                                                       
CONECT   13    9   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15    8   17                                                  
CONECT   17   16                                                            
CONECT   18   15                                                            
CONECT   19   14                                                            
CONECT   20    7   21   26                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22    6                                                       
CONECT   24   22                                                            
CONECT   25   21                                                            
CONECT   26   20                                                            
CONECT   27    2   28   98                                                  
CONECT   28   27   29   88                                                  
CONECT   29   28   30                                                       
CONECT   30   29    1   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   39                                                  
CONECT   35   34   36   43                                                  
CONECT   36   35   37   42                                                  
CONECT   37   36   38   41                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38   34                                                       
CONECT   40   38                                                            
CONECT   41   37                                                            
CONECT   42   36                                                            
CONECT   43   35   44                                                       
CONECT   44   43   45   49                                                  
CONECT   45   44   46   87                                                  
CONECT   46   45   47   86                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48   44                                                       
CONECT   50   48   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53                                                       
CONECT   53   52   54   58                                                  
CONECT   54   53   55   74                                                  
CONECT   55   54   56   62                                                  
CONECT   56   55   57   61                                                  
CONECT   57   56   58   59                                                  
CONECT   58   57   53                                                       
CONECT   59   57   60                                                       
CONECT   60   59                                                            
CONECT   61   56                                                            
CONECT   62   55   63                                                       
CONECT   63   62   64   65                                                  
CONECT   64   63                                                            
CONECT   65   63   66   70                                                  
CONECT   66   65   67                                                       
CONECT   67   66   68   73                                                  
CONECT   68   67   69   72                                                  
CONECT   69   68   70   71                                                  
CONECT   70   69   65                                                       
CONECT   71   69                                                            
CONECT   72   68                                                            
CONECT   73   67                                                            
CONECT   74   54   75                                                       
CONECT   75   74   76   77                                                  
CONECT   76   75                                                            
CONECT   77   75   78   82                                                  
CONECT   78   77   79                                                       
CONECT   79   78   80   85                                                  
CONECT   80   79   81   84                                                  
CONECT   81   80   82   83                                                  
CONECT   82   81   77                                                       
CONECT   83   81                                                            
CONECT   84   80                                                            
CONECT   85   79                                                            
CONECT   86   46                                                            
CONECT   87   45                                                            
CONECT   88   28   89                                                       
CONECT   89   88   90                                                       
CONECT   90   89   91   92                                                  
CONECT   91   90                                                            
CONECT   92   90   93  109                                                  
CONECT   93   92   94  106                                                  
CONECT   94   93   95  102                                                  
CONECT   95   94   96   99                                                  
CONECT   96   95   97   98                                                  
CONECT   97   96                                                            
CONECT   98   96   27                                                       
CONECT   99   95  100                                                       
CONECT  100   99  101  105                                                  
CONECT  101  100  102  104                                                  
CONECT  102  101   94  103                                                  
CONECT  103  102                                                            
CONECT  104  101                                                            
CONECT  105  100                                                            
CONECT  106   93  107  112                                                  
CONECT  107  106  108  111                                                  
CONECT  108  107  109  110                                                  
CONECT  109  108   92                                                       
CONECT  110  108                                                            
CONECT  111  107                                                            
CONECT  112  106                                                            
MASTER        0    0    0    0    0    0    0    0  112    0  246    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,19S,20R,22R)-7,8,9,12,13,14,28,29,30,33,34,35-Dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0,.0,.0,.0,.0,]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-20-yl 2-[2,3-dihydroxy-5-({[(2S,3R,4R,5S,6S)-5-hydroxy-6-(hydroxymethyl)-3,4-bis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₆₈H₅₀O₄₄

Average Mass

1571.1040 Da

Monoisotopic Mass

1570.16749 Da

IUPAC Name

(1R,2S,19S,20R,22R)-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0^{2,19}.0^{5,10}.0^{11,16}.0^{26,31}.0^{32,37}]nonatriaconta-5(10),6,8,11(16),12,14,26(31),27,29,32(37),33,35-dodecaen-20-yl 2-[2,3-dihydroxy-5-({[(2S,3R,4R,5S,6S)-5-hydroxy-6-(hydroxymethyl)-3,4-bis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4,5-trihydroxybenzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

OC[C@@H]1O[C@@H](OC(=O)C2=CC(OC3=C(C=C(O)C(O)=C3O)C(=O)O[C@H]3O[C@@H]4COC(=O)C5=C(C(O)=C(O)C(O)=C5)C5=C(C=C(O)C(O)=C5O)C(=O)O[C@H]4[C@@H]4OC(=O)C5=C(C(O)=C(O)C(O)=C5)C5=C(C=C(O)C(O)=C5O)C(=O)O[C@H]34)=C(O)C(O)=C2)[C@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H]1O

InChI Identifier

InChI=1S/C68H50O44/c69-12-33-47(88)55(107-59(94)14-1-22(70)39(80)23(71)2-14)57(109-60(95)15-3-24(72)40(81)25(73)4-15)67(104-33)111-61(96)16-5-26(74)41(82)32(6-16)103-53-21(11-31(79)46(87)52(53)93)66(101)112-68-58-56(108-64(99)19-9-29(77)44(85)50(91)37(19)38-20(65(100)110-58)10-30(78)45(86)51(38)92)54-34(105-68)13-102-62(97)17-7-27(75)42(83)48(89)35(17)36-18(63(98)106-54)8-28(76)43(84)49(36)90/h1-11,33-34,47,54-58,67-93H,12-13H2/t33-,34+,47-,54+,55+,56-,57+,58-,67-,68+/m0/s1

InChI Key

YKLNPEYKZHHXKJ-QRFSJKBVSA-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
Geum japonicum	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
Diphenylether
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
Phenoxy compound
Phenol ether
Catechol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	3.87	ALOGPS
logP	5.19	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	5.9	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	35	ChemAxon
Hydrogen Donor Count	25	ChemAxon
Polar Surface Area	743.84 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	354.32 m³·mol⁻¹	ChemAxon
Polarizability	139.78 Å³	ChemAxon
Number of Rings	12	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

154496619

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Gemin C (NP0074255)

MOL for NP0074255 (Gemin C)

3D MOL for NP0074255 (Gemin C)

3D SDF for NP0074255 (Gemin C)

3D-SDF for NP0074255 (Gemin C)

PDB for NP0074255 (Gemin C)

3D PDB for NP0074255 (Gemin C)

SMILES for NP0074255 (Gemin C)

INCHI for NP0074255 (Gemin C)

Structure for NP0074255 (Gemin C)

3D Structure for NP0074255 (Gemin C)