NP-MRD: Showing NP-Card for Tataroside (NP0073762)

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Record Information

Version

2.0

Created at

2022-04-28 18:59:10 UTC

Updated at

2022-04-28 18:59:10 UTC

NP-MRD ID

NP0073762

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tataroside

Description

(3R,3aR,9S,11aS)-3-hydroxy-6-(hydroxymethyl)-3,10-dimethyl-9-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Tataroside is found in Lactuca tatarica C.A.Mey. Based on a literature review very few articles have been published on (3R,3aR,9S,11aS)-3-hydroxy-6-(hydroxymethyl)-3,10-dimethyl-9-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220592D          

 31 33  0  0  1  0            999 V2000
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9139    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0945    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3919   -0.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6216   -1.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  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
  1 10  1  0  0  0  0
 10 11  1  1  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 16 19  1  6  0  0  0
 15 20  1  1  0  0  0
 14 21  1  6  0  0  0
 21 22  1  0  0  0  0
  9 23  1  0  0  0  0
  7 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  6  0  0  0
  3 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 63 65  0  0  0  0  0  0  0  0999 V2000
    0.6650    1.9184    0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3776    1.3835   -0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6046    1.8451    0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8246    1.5616   -0.7071 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5969    2.7996   -0.8160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2172    2.9247    0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5755    4.0109    0.9089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3887    1.5903    1.0332 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8442    1.2872    1.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7091    1.5805    2.2143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8398    0.7208   -0.0610 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5175   -0.6657    0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4767   -0.8576    1.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4487   -1.8440    0.9197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2196   -3.0456    1.8496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8153   -2.6391    3.0921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7152   -1.8132   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6749   -0.8184   -1.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1717    0.3916   -0.9837 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4210   -0.0788   -0.6436 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4413    0.1630   -1.5261 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9271   -0.9813   -2.1431 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8323   -1.6297   -1.3543 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3316   -1.9651    0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3903   -2.6301    0.6766 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1203   -0.8808   -1.3452 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8755   -1.2518   -2.4818 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8924    0.5807   -1.3805 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7781    1.2604   -0.5075 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5163    1.0471   -0.9902 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3562    2.3229   -1.5290 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1689    2.5639    1.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2169    1.0713    1.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3786    2.5760    0.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7897    2.5955    0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6610    1.3619   -1.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8915    0.2147    1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4551    1.4433    0.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2107    1.8933    2.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0607    0.9666    2.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6943    0.6273   -0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4997   -1.0401    0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4614   -1.2936   -0.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0138    0.0682    1.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9314   -1.3077    2.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5281   -3.7739    1.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2042   -3.5898    1.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0599   -3.1877    3.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0023   -2.6771   -0.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6455   -0.6294   -1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1649   -1.4061   -2.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2985    0.8957   -1.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9604    0.7286   -2.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0296   -2.6195   -1.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0491   -1.0990    0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5270   -2.7191   -0.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1898   -2.7824    1.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7645   -1.1393   -0.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5976   -0.7135   -3.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407    0.9711   -2.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6446    2.2336   -0.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4926    1.1884    0.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9375    2.2915   -2.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  1
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 19  2  1  0
 30 21  1  0
 11  4  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  4 36  1  6
  9 37  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  6
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  6
 21 53  1  6
 23 54  1  6
 24 55  1  0
 24 56  1  0
 25 57  1  0
 26 58  1  1
 27 59  1  0
 28 60  1  6
 29 61  1  0
 30 62  1  1
 31 63  1  0
M  END


  Mrv1652304282220592D          

 31 33  0  0  1  0            999 V2000
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9139    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0945    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3919   -0.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6216   -1.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  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
  1 10  1  0  0  0  0
 10 11  1  1  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 16 19  1  6  0  0  0
 15 20  1  1  0  0  0
 14 21  1  6  0  0  0
 21 22  1  0  0  0  0
  9 23  1  0  0  0  0
  7 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  6  0  0  0
  3 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073762

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C/[C@@H]2OC(=O)[C@](C)(O)[C@@H]2CC\C(CO)=C/C[C@@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O10/c1-10-7-14-12(21(2,28)20(27)31-14)5-3-11(8-22)4-6-13(10)29-19-18(26)17(25)16(24)15(9-23)30-19/h4,7,12-19,22-26,28H,3,5-6,8-9H2,1-2H3/b10-7+,11-4+/t12-,13+,14+,15-,16-,17+,18-,19-,21-/m1/s1

> <INCHI_KEY>
JDSFNHPEWCEHFB-DVLNSLILSA-N

> <FORMULA>
C21H32O10

> <MOLECULAR_WEIGHT>
444.477

> <EXACT_MASS>
444.19954723

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
44.89387919447663

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,3aR,9S,11aS)-3-hydroxy-6-(hydroxymethyl)-3,10-dimethyl-9-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <ALOGPS_LOGP>
-1.13

> <JCHEM_LOGP>
-1.5476355130000008

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.497449724550798

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.941849308097709

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9711025860619769

> <JCHEM_POLAR_SURFACE_AREA>
166.14

> <JCHEM_REFRACTIVITY>
107.3787

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aR,9S,11aS)-3-hydroxy-6-(hydroxymethyl)-3,10-dimethyl-9-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <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       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.336   6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.002   9.240   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.573   0.294   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.465   2.016   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.370   0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.910   0.770   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.598  -1.518   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.160  -1.986   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   27                                                  
CONECT    7    6    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9    1   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17                                                            
CONECT   19   16                                                            
CONECT   20   15                                                            
CONECT   21   14   22                                                       
CONECT   22   21                                                            
CONECT   23    9                                                            
CONECT   24    7   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    6   28   29                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    3   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₂O₁₀

Average Mass

444.4770 Da

Monoisotopic Mass

444.19955 Da

IUPAC Name

(3R,3aR,9S,11aS)-3-hydroxy-6-(hydroxymethyl)-3,10-dimethyl-9-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

Traditional Name

(3R,3aR,9S,11aS)-3-hydroxy-6-(hydroxymethyl)-3,10-dimethyl-9-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

CAS Registry Number

Not Available

SMILES

C\C1=C/[C@@H]2OC(=O)[C@](C)(O)[C@@H]2CC\C(CO)=C/C[C@@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C21H32O10/c1-10-7-14-12(21(2,28)20(27)31-14)5-3-11(8-22)4-6-13(10)29-19-18(26)17(25)16(24)15(9-23)30-19/h4,7,12-19,22-26,28H,3,5-6,8-9H2,1-2H3/b10-7+,11-4+/t12-,13+,14+,15-,16-,17+,18-,19-,21-/m1/s1

InChI Key

JDSFNHPEWCEHFB-DVLNSLILSA-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
Lactuca tatarica C.A.Mey.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Terpene glycoside
Germacranolide
Sesquiterpenoid
Germacrane sesquiterpenoid
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Oxane
Monosaccharide
Gamma butyrolactone
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.1	ALOGPS
logP	-1.5	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	11.94	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.38 m³·mol⁻¹	ChemAxon
Polarizability	44.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

162878193

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Tataroside (NP0073762)

MOL for NP0073762 (Tataroside)

3D MOL for NP0073762 (Tataroside)

3D SDF for NP0073762 (Tataroside)

3D-SDF for NP0073762 (Tataroside)

PDB for NP0073762 (Tataroside)

3D PDB for NP0073762 (Tataroside)

SMILES for NP0073762 (Tataroside)

INCHI for NP0073762 (Tataroside)

Structure for NP0073762 (Tataroside)

3D Structure for NP0073762 (Tataroside)