NP-MRD: Showing NP-Card for (-)-Robustaside D (NP0075732)

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Record Information

Version

2.0

Created at

2022-04-28 20:58:31 UTC

Updated at

2022-04-28 20:58:31 UTC

NP-MRD ID

NP0075732

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Robustaside D

Description

Robustaside D belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. (-)-Robustaside D is found in Grevillea robusta and Grevillea robusta A.Cunn. (-)-Robustaside D was first documented in 2011 (PMID: 21155593). Based on a literature review very few articles have been published on robustaside D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222582D          

 31 33  0  0  1  0            999 V2000
    1.1767   -4.5844    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8912   -4.9969    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8912   -5.8219    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1767   -6.2344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4622   -5.8219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4622   -4.9969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2522   -4.5844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2522   -3.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9667   -3.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9667   -2.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2522   -2.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4622   -2.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4622   -3.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2522   -1.2844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1767   -7.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8912   -7.4719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8912   -8.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1767   -8.7094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -8.7094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -9.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3201   -9.9469    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1326  -10.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4147  -10.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8844  -11.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1666  -12.2727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0720  -11.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7898  -10.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6023   -9.1717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -6.2344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -4.5844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1767   -3.7594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
  4 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 21 27  1  0  0  0  0
 21 28  1  1  0  0  0
  3 29  1  6  0  0  0
  2 30  1  1  0  0  0
  1 31  1  6  0  0  0
M  END

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
   -6.2082   -2.3705    2.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3499   -1.4793    2.2898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0105   -1.7625    2.8225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1076   -0.8358    3.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3990    0.5680    2.6991 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3102    1.2828    3.9008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4231    1.1068    1.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5606    0.9272    0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5949    1.4618   -0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5929    2.1163   -0.1907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7574    1.2633   -1.9062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9754    1.6725   -2.9662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4227    1.1669   -3.0205 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1808    1.5126   -1.9627 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3199    0.7889   -1.7280 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0874   -0.0223   -0.6223 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7316    0.0770    0.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7052    0.9682    0.9305 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2757    0.9488    2.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8980    0.0486    3.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4642    0.0314    4.4409 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9161   -0.8489    2.8211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3438   -0.8445    1.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8403   -0.0047   -2.8779 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6973    0.7493   -3.6797 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8225   -0.6543   -3.7352 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0215   -2.0379   -3.8713 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4290   -0.3545   -3.2230 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4763   -0.6370   -4.2533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7523    0.8039    2.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6749   -0.0967    1.9647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8175   -2.8164    3.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1487   -1.0994    3.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2050    1.5637    4.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5780    1.6607    2.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4063    0.3721    0.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9448    2.7808   -3.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802    1.3030   -3.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9301    1.5733   -3.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1054    1.5196   -1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0431    1.7008    0.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0383    1.6707    2.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2979   -0.5529    4.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5833   -1.5882    3.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5733   -1.5446    1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4902   -0.8225   -2.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3869    1.2330   -3.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8609   -0.2499   -4.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8794   -2.3233   -3.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1931   -0.8919   -2.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0801   -1.3725   -4.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0251    1.8390    1.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6589    0.1746    1.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 13  1  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  2  0
  7  5  1  0
  5  6  1  1
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 31  1  0
 31 30  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 15 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 30  5  1  0
 23 17  1  0
 29 51  1  0
 28 50  1  1
 13 39  1  6
 12 37  1  0
 12 38  1  0
  8 36  1  0
  7 35  1  0
  6 34  1  0
  4 33  1  0
  3 32  1  0
 31 53  1  0
 30 52  1  0
 15 40  1  1
 18 41  1  0
 19 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  1
 25 47  1  0
 26 48  1  6
 27 49  1  0
M  END


  Mrv1652304282222582D          

 31 33  0  0  1  0            999 V2000
    1.1767   -4.5844    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8912   -4.9969    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8912   -5.8219    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1767   -6.2344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4622   -5.8219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4622   -4.9969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2522   -4.5844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2522   -3.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9667   -3.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9667   -2.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2522   -2.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4622   -2.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4622   -3.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2522   -1.2844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1767   -7.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8912   -7.4719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8912   -8.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1767   -8.7094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -8.7094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -9.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3201   -9.9469    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1326  -10.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4147  -10.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8844  -11.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1666  -12.2727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0720  -11.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7898  -10.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6023   -9.1717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -6.2344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -4.5844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1767   -3.7594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
  4 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 21 27  1  0  0  0  0
 21 28  1  1  0  0  0
  3 29  1  6  0  0  0
  2 30  1  1  0  0  0
  1 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0075732

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](COC(=O)\C=C\C2(O)C=CC(=O)C=C2)O[C@@H](OC2=CC=C(O)C=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O10/c22-12-1-3-14(4-2-12)30-20-19(27)18(26)17(25)15(31-20)11-29-16(24)7-10-21(28)8-5-13(23)6-9-21/h1-10,15,17-20,22,25-28H,11H2/b10-7+/t15-,17-,18+,19-,20-/m1/s1

> <INCHI_KEY>
KQIQKULTIAJZKL-VHFDLOJPSA-N

> <FORMULA>
C21H22O10

> <MOLECULAR_WEIGHT>
434.397

> <EXACT_MASS>
434.121296908

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
41.419790092604956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl (2E)-3-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)prop-2-enoate

> <ALOGPS_LOGP>
0.38

> <JCHEM_LOGP>
0.4859460873333334

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.182148620389066

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.820372083165651

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4538193333118707

> <JCHEM_POLAR_SURFACE_AREA>
162.98

> <JCHEM_REFRACTIVITY>
106.83539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
robustaside D

> <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       2.197  -8.558   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.530  -9.328   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.530 -10.868   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.197 -11.638   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.863 -10.868   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.863  -9.328   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.471  -8.558   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.471  -7.018   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.805  -6.248   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.805  -4.708   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.471  -3.938   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.863  -4.708   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.863  -6.248   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.471  -2.398   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.197 -13.178   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.530 -13.948   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.530 -15.488   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.197 -16.258   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.864 -16.258   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.864 -17.798   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.198 -18.568   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.714 -18.835   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.241 -20.282   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.251 -21.462   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.778 -22.909   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.734 -21.194   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.208 -19.747   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.724 -17.121   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.864 -11.638   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.864  -8.558   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.197  -7.018   0.000  0.00  0.00           O+0
CONECT    1    2    6   31                                                  
CONECT    2    1    3   30                                                  
CONECT    3    2    4   29                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11                                                            
CONECT   15    4   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   27   28                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   21                                                       
CONECT   28   21                                                            
CONECT   29    3                                                            
CONECT   30    2                                                            
CONECT   31    1                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₁₀

Average Mass

434.3970 Da

Monoisotopic Mass

434.12130 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl (2E)-3-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)prop-2-enoate

Traditional Name

robustaside D

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](COC(=O)\C=C\C2(O)C=CC(=O)C=C2)O[C@@H](OC2=CC=C(O)C=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C21H22O10/c22-12-1-3-14(4-2-12)30-20-19(27)18(26)17(25)15(31-20)11-29-16(24)7-10-21(28)8-5-13(23)6-9-21/h1-10,15,17-20,22,25-28H,11H2/b10-7+/t15-,17-,18+,19-,20-/m1/s1

InChI Key

KQIQKULTIAJZKL-VHFDLOJPSA-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
Grevillea robusta	LOTUS Database	35616633
Grevillea robusta A.Cunn	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Saccharolipid
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
4-alkoxyphenol
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Monosaccharide
Oxane
Fatty acyl
Benzenoid
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Cyclic ketone
Carboxylic acid ester
Ketone
Organoheterocyclic compound
Polyol
Acetal
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Organooxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

cyclic ketone (CHEBI:70146 )
phenols (CHEBI:70146 )
beta-D-glucoside (CHEBI:70146 )
monosaccharide derivative (CHEBI:70146 )
enoate ester (CHEBI:70146 )

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	0.38	ALOGPS
logP	0.49	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.82	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	106.84 m³·mol⁻¹	ChemAxon
Polarizability	41.42 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00037742

Chemspider ID

22913722

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

38358972

PDB ID

Not Available

ChEBI ID

70146

Good Scents ID

Not Available

References

General References

Ovenden SP, Cobbe M, Kissell R, Birrell GW, Chavchich M, Edstein MD: Phenolic glycosides with antimalarial activity from Grevillea "Poorinda Queen". J Nat Prod. 2011 Jan 28;74(1):74-8. doi: 10.1021/np100737q. Epub 2010 Dec 14. [PubMed:21155593 ]

Showing NP-Card for (-)-Robustaside D (NP0075732)

MOL for NP0075732 ((-)-Robustaside D)

3D MOL for NP0075732 ((-)-Robustaside D)

3D SDF for NP0075732 ((-)-Robustaside D)

3D-SDF for NP0075732 ((-)-Robustaside D)

PDB for NP0075732 ((-)-Robustaside D)

3D PDB for NP0075732 ((-)-Robustaside D)

SMILES for NP0075732 ((-)-Robustaside D)

INCHI for NP0075732 ((-)-Robustaside D)

Structure for NP0075732 ((-)-Robustaside D)

3D Structure for NP0075732 ((-)-Robustaside D)