NP-MRD: Showing NP-Card for (2e,4e,7r,8s)-2,7-dimethyl-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid (NP0183015)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 21:51:03 UTC

Updated at

2022-09-03 21:51:03 UTC

NP-MRD ID

NP0183015

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,4e,7r,8s)-2,7-dimethyl-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid

Description

(2E,4E,7R,8S)-2,7-dimethyl-8-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid belongs to the class of organic compounds known as rhamnolipids. These are glycolipids structurally characterized by a glycosyl head group, in this case a rhamnose moiety, and a 3-(hydroxyalkanoyloxy)alkanoic acid (HAA) fatty acid tail. (2e,4e,7r,8s)-2,7-dimethyl-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid is found in Cydonia oblonga. Based on a literature review very few articles have been published on (2E,4E,7R,8S)-2,7-dimethyl-8-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032223512D          

 28 28  0  0  1  0            999 V2000
   -1.4289   -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
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    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
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  2  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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  2  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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 O   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
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  6  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  1  0  0  0
  2 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
M  END

     RDKit          3D

 56 56  0  0  0  0  0  0  0  0999 V2000
    6.4059    1.4732    1.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2835    0.2508    0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1066   -0.3222    0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9248    0.1972    0.9763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7492   -0.4398    0.8122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5160    0.0197    1.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4091    0.3690    0.4597 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8703    1.4332   -0.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941   -0.7552   -0.0584 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1302   -1.6573   -1.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4932   -1.1365   -2.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3341   -0.0054   -2.8712 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1249   -2.0509   -3.2673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6488   -0.2128   -0.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6843   -0.6164    0.3876 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5469   -1.3697   -0.3622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6316   -0.7796   -0.9079 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3749   -0.0284   -2.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4699    0.9950   -2.0613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4216    0.0991    0.0367 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7343   -0.2825    0.1774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7672    0.0898    1.4261 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4344    0.9649    2.2460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3234    0.5115    1.1586 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7389    0.6326    2.4363 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4685   -0.3022   -0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4057   -1.3388   -0.9211 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6927    0.3250   -0.0668 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4610    1.7329    1.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9313    2.3369    0.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9700    1.3549    2.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0630   -1.2175   -0.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9539    1.0757    1.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7848   -1.3100    0.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7601    0.9418    2.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822   -0.6877    2.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3225    0.9593    1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7930    1.2272   -1.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2000    2.2988    0.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0455    1.8887   -1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6471   -1.4110    0.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7059   -2.4442   -1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9244   -2.3440   -0.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9421   -3.0364   -3.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683   -1.3084    1.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3463   -1.6093   -1.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0038   -0.7142   -2.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3178    0.4013   -2.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8653    1.8408   -1.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4017    1.1745   -0.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0056   -0.2304    1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7966   -0.9629    1.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9360    0.5191    2.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2822    1.4772    0.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8311    1.5794    2.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0744    0.4040    0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 26  1  0
 26 28  1  0
 26 27  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 15  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  7 37  1  1
  6 35  1  0
  6 36  1  0
  5 34  1  0
  4 33  1  0
  3 32  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 28 56  1  0
  9 41  1  1
 10 42  1  0
 10 43  1  0
 13 44  1  0
 15 45  1  1
 17 46  1  6
 18 47  1  0
 18 48  1  0
 19 49  1  0
 20 50  1  6
 21 51  1  0
 22 52  1  1
 23 53  1  0
 24 54  1  6
 25 55  1  0
M  END


  Mrv1652309032223512D          

 28 28  0  0  1  0            999 V2000
   -1.4289   -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
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    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
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  2  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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  2  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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 O   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
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  6  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  1  0  0  0
  2 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0183015

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H28O10/c1-9(5-3-4-6-10(2)17(25)26)11(7-13(20)21)27-18-16(24)15(23)14(22)12(8-19)28-18/h3-4,6,9,11-12,14-16,18-19,22-24H,5,7-8H2,1-2H3,(H,20,21)(H,25,26)/b4-3+,10-6+/t9-,11+,12-,14-,15+,16-,18-/m1/s1

> <INCHI_KEY>
WHRWRZSKZMYJOX-GPSLNCNOSA-N

> <FORMULA>
C18H28O10

> <MOLECULAR_WEIGHT>
404.412

> <EXACT_MASS>
404.168247102

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
40.72944481776287

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,7R,8S)-2,7-dimethyl-8-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid

> <JCHEM_LOGP>
-0.33629254133333325

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.784877248217773

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.044256173369905

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083544194518

> <JCHEM_POLAR_SURFACE_AREA>
173.98

> <JCHEM_REFRACTIVITY>
96.1104

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,7R,8S)-2,7-dimethyl-8-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   15   25                                                  
CONECT   25   24                                                            
CONECT   26    2   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   56    0
END

View in JSmol

Synonyms

Value	Source
(2E,4E,7R,8S)-2,7-Dimethyl-8-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioate	Generator

Chemical Formula

C₁₈H₂₈O₁₀

Average Mass

404.4120 Da

Monoisotopic Mass

404.16825 Da

IUPAC Name

(2E,4E,7R,8S)-2,7-dimethyl-8-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid

Traditional Name

(2E,4E,7R,8S)-2,7-dimethyl-8-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H28O10/c1-9(5-3-4-6-10(2)17(25)26)11(7-13(20)21)27-18-16(24)15(23)14(22)12(8-19)28-18/h3-4,6,9,11-12,14-16,18-19,22-24H,5,7-8H2,1-2H3,(H,20,21)(H,25,26)/b4-3+,10-6+/t9-,11+,12-,14-,15+,16-,18-/m1/s1

InChI Key

WHRWRZSKZMYJOX-GPSLNCNOSA-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
Cydonia oblonga	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as rhamnolipids. These are glycolipids structurally characterized by a glycosyl head group, in this case a rhamnose moiety, and a 3-(hydroxyalkanoyloxy)alkanoic acid (HAA) fatty acid tail.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Rhamnolipids

Alternative Parents

Substituents

Rhamnolipid
Mono-rhamnolipid
Fatty acyl glycoside of mono- or disaccharide
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Medium-chain fatty acid
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Sugar acid
Methyl-branched fatty acid
Unsaturated fatty acid
Oxane
Monosaccharide
Fatty acid
Dicarboxylic acid or derivatives
Secondary alcohol
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Carboxylic acid
Oxacycle
Acetal
Organic oxide
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
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	-0.34	ChemAxon
pKa (Strongest Acidic)	4.04	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.98 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	96.11 m³·mol⁻¹	ChemAxon
Polarizability	40.73 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

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

124708085

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e,4e,7r,8s)-2,7-dimethyl-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid (NP0183015)

MOL for NP0183015 ((2e,4e,7r,8s)-2,7-dimethyl-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid)

3D MOL for NP0183015 ((2e,4e,7r,8s)-2,7-dimethyl-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid)

3D SDF for NP0183015 ((2e,4e,7r,8s)-2,7-dimethyl-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid)

3D-SDF for NP0183015 ((2e,4e,7r,8s)-2,7-dimethyl-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid)

PDB for NP0183015 ((2e,4e,7r,8s)-2,7-dimethyl-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid)

3D PDB for NP0183015 ((2e,4e,7r,8s)-2,7-dimethyl-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid)

SMILES for NP0183015 ((2e,4e,7r,8s)-2,7-dimethyl-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid)

INCHI for NP0183015 ((2e,4e,7r,8s)-2,7-dimethyl-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid)

Structure for NP0183015 ((2e,4e,7r,8s)-2,7-dimethyl-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid)

3D Structure for NP0183015 ((2e,4e,7r,8s)-2,7-dimethyl-8-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}deca-2,4-dienedioic acid)