NP-MRD: Showing NP-Card for (2r,3r,4s,5s,6r)-2-{[(5s,6e,9e)-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6,9-trien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0202898)

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Record Information

Version

2.0

Created at

2022-09-04 22:13:12 UTC

Updated at

2022-09-04 22:13:12 UTC

NP-MRD ID

NP0202898

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4s,5s,6r)-2-{[(5s,6e,9e)-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6,9-trien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

Amarantholidoside I belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. (2r,3r,4s,5s,6r)-2-{[(5s,6e,9e)-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6,9-trien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Amaranthus retroflexus. Based on a literature review very few articles have been published on Amarantholidoside I.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052200132D          

 29 29  0  0  1  0            999 V2000
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    4.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  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
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
  7 18  1  1  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  1  0  0  0
M  END

     RDKit          3D

 65 65  0  0  0  0  0  0  0  0999 V2000
    1.2447    2.7468   -2.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    2.1136   -1.9111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1305    2.5688   -0.5309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1876    4.0494   -0.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2557    2.3879    0.2705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0467    1.8772    0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8351    0.3770    0.2075 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3469    0.0200    0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2877   -0.7908    0.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2029   -1.3939   -0.8202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4515   -1.0969    1.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7296   -0.6757    0.7803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5068    0.2107    1.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7931    0.6738    0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1749    1.9676    1.4583 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8629   -0.3548    1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6693    0.8825   -0.5693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0143   -0.1620    0.6931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6661   -0.9649   -0.2436 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8787   -0.3924   -0.4840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8815   -1.2353   -0.8896 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1656   -0.4300   -0.9366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2465   -1.2267   -1.3455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1217   -2.3900    0.0532 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0859   -3.5711   -0.6949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0130   -2.4971    1.0886 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1151   -1.4257    1.9441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7143   -2.3562    0.3072 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6834   -3.2942   -0.7289 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4528    2.4603   -3.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8120    3.5868   -2.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1788    1.2822   -2.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6593    4.3115    0.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7037    4.6663   -0.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9931    4.2469   -1.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0740    2.8642    1.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2152    2.3420    1.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9295    2.0611   -0.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7190    0.0129   -0.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4615    0.4297    1.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8883   -2.2646   -0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4910   -0.6678   -1.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1784   -1.8124   -0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -0.6966    2.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4987   -2.2224    1.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0467   -1.0808   -0.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1725    0.6053    2.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2888    2.0850    1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9120    1.8715    2.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6439    2.8502    1.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8820    0.0185    0.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7490   -0.6683    2.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7230   -1.2821    0.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7007    0.0316   -1.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1045   -1.0135   -1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6767   -1.5604   -1.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3933    0.0365    0.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1004    0.4044   -1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1652   -1.2978   -2.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0901   -2.3496    0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8352   -3.4114   -1.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0713   -3.4800    1.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0286   -1.2879    2.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8316   -2.5007    0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3656   -4.1879   -0.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  0
  6  3  1  0
  3  4  1  0
  3  5  1  1
  3  2  1  0
  2  1  2  3
  7 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 19  1  0
 10 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 13 47  1  0
 15 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  0
  8 40  1  0
  7 39  1  6
  6 37  1  0
  6 38  1  0
  4 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  2 32  1  0
  1 30  1  0
  1 31  1  0
 19 55  1  6
 21 56  1  6
 22 57  1  0
 22 58  1  0
 23 59  1  0
 24 60  1  1
 25 61  1  0
 26 62  1  1
 27 63  1  0
 28 64  1  1
 29 65  1  0
M  END


  Mrv1652309052200132D          

 29 29  0  0  1  0            999 V2000
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    4.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  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
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
  7 18  1  1  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0202898

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H36O8/c1-6-21(5,27)11-14(10-13(2)8-7-9-20(3,4)26)28-19-18(25)17(24)16(23)15(12-22)29-19/h6-7,9-10,14-19,22-27H,1,8,11-12H2,2-5H3/b9-7+,13-10+/t14-,15-,16-,17+,18-,19-,21?/m1/s1

> <INCHI_KEY>
HARVFBHVMLFMBX-PTRYXRMWSA-N

> <FORMULA>
C21H36O8

> <MOLECULAR_WEIGHT>
416.511

> <EXACT_MASS>
416.241018119

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
44.59684458595184

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(5S,6E,9E)-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6,9-trien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
-0.038783391333333195

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.185162726876388

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.208392613098757

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5466040498455924

> <JCHEM_POLAR_SURFACE_AREA>
139.84

> <JCHEM_REFRACTIVITY>
109.8431

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(5S,6E,9E)-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6,9-trien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.897   5.954   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.437   3.286   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.565  10.574   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.105   7.906   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18    7   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   19   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₆O₈

Average Mass

416.5110 Da

Monoisotopic Mass

416.24102 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[(5S,6E,9E)-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6,9-trien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2R,3R,4S,5S,6R)-2-{[(5S,6E,9E)-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6,9-trien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H36O8/c1-6-21(5,27)11-14(10-13(2)8-7-9-20(3,4)26)28-19-18(25)17(24)16(23)15(12-22)29-19/h6-7,9-10,14-19,22-27H,1,8,11-12H2,2-5H3/b9-7+,13-10+/t14-,15-,16-,17+,18-,19-,21?/m1/s1

InChI Key

HARVFBHVMLFMBX-PTRYXRMWSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Amaranthus retroflexus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Farsesane sesquiterpenoid
Sesquiterpenoid
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Fatty acyl
Monosaccharide
Oxane
Tertiary alcohol
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-0.039	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	139.84 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	109.84 m³·mol⁻¹	ChemAxon
Polarizability	44.6 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9728246

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11553468

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,4s,5s,6r)-2-{[(5s,6e,9e)-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6,9-trien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0202898)

MOL for NP0202898 ((2r,3r,4s,5s,6r)-2-{[(5s,6e,9e)-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6,9-trien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0202898 ((2r,3r,4s,5s,6r)-2-{[(5s,6e,9e)-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6,9-trien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0202898 ((2r,3r,4s,5s,6r)-2-{[(5s,6e,9e)-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6,9-trien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0202898 ((2r,3r,4s,5s,6r)-2-{[(5s,6e,9e)-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6,9-trien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0202898 ((2r,3r,4s,5s,6r)-2-{[(5s,6e,9e)-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6,9-trien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0202898 ((2r,3r,4s,5s,6r)-2-{[(5s,6e,9e)-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6,9-trien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0202898 ((2r,3r,4s,5s,6r)-2-{[(5s,6e,9e)-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6,9-trien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0202898 ((2r,3r,4s,5s,6r)-2-{[(5s,6e,9e)-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6,9-trien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0202898 ((2r,3r,4s,5s,6r)-2-{[(5s,6e,9e)-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6,9-trien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0202898 ((2r,3r,4s,5s,6r)-2-{[(5s,6e,9e)-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6,9-trien-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)