NP-MRD: Showing NP-Card for [(1s,2s)-3-oxo-2-[(2z)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid (NP0237352)

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Record Information

Version

1.0

Created at

2022-09-06 20:28:14 UTC

Updated at

2022-09-06 20:28:14 UTC

NP-MRD ID

NP0237352

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,2s)-3-oxo-2-[(2z)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid

Description

Tuberonic acid glucoside belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. [(1s,2s)-3-oxo-2-[(2z)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid is found in Phyllanthus emblica and Solanum tuberosum. It was first documented in 2010 (PMID: 20715141). Based on a literature review a significant number of articles have been published on Tuberonic acid glucoside (PMID: 30807743) (PMID: 26241499) (PMID: 21521631) (PMID: 20570296).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062222282D          

 27 28  0  0  1  0            999 V2000
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  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
    1.4289   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0964   -5.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -6.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -6.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5315   -6.8870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615   -5.4349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0231   -5.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946   -4.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9793   -4.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5924   -4.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3770   -4.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9901   -4.9672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7747   -4.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3878   -5.2643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1724   -5.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7855   -5.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5701   -5.3064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3439   -4.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1286   -3.9474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7308   -3.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9024   -2.8434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9462   -3.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3331   -3.3533    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
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  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
  8 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  1  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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

     RDKit          3D

 55 56  0  0  0  0  0  0  0  0999 V2000
   -5.5907   -3.3614   -0.1901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2433   -2.5142   -0.8473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3546   -2.9530   -1.5372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8390   -1.0969   -0.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5964   -0.9182   -0.0404 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8215   -1.3215    1.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9660   -0.3609    2.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9491    0.8725    1.3945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8185    1.9933    1.8182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1195    0.4980   -0.0243 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7308    0.5192   -0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2869    1.9059   -0.6663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1977    2.2965   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3009    1.3986    0.6493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0669    1.5234   -0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9270    0.6812    0.6035 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1902    0.7432    0.0145 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5197   -0.5435   -0.3664 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6193   -0.5618   -1.1904 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9372   -2.0391   -1.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8190   -2.5829   -2.0681 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7892    0.1630   -0.6338 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2094    1.1601   -1.5264 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5940    0.7191    0.7394 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0073   -0.2029    1.7008 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2107    1.2346    1.0069 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8129    0.7854    2.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7501   -2.4350   -2.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5663   -0.8236   -1.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6338   -0.4216   -0.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8311   -1.6220   -0.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8757   -1.1636    1.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4845   -2.3552    1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4314   -0.1850    3.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9485   -0.7714    2.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8044    1.1945   -0.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1581   -0.2289   -0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9339    0.2086   -1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9429    2.6411   -1.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9443    3.3504   -0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5132    0.3415    0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1714    1.7030    1.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4176    2.5584    0.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8974    1.2244   -1.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1716    1.4626   -0.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3231   -0.1137   -2.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8666   -2.1675   -2.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0526   -2.5421   -0.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4928   -3.3899   -1.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6514   -0.5664   -0.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9352    0.9455   -2.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2889    1.5975    0.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3753    0.2884    2.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1444    2.3427    1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4849    0.8896    2.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  1  0
 10  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
 17 26  1  0
 26 27  1  0
 26 24  1  0
 24 25  1  0
 24 22  1  0
 22 23  1  0
 22 19  1  0
  8 10  1  0
 21 49  1  0
 20 47  1  0
 20 48  1  0
 19 46  1  6
 17 45  1  6
 15 43  1  0
 15 44  1  0
 14 41  1  0
 14 42  1  0
 13 40  1  0
 12 39  1  0
 11 37  1  0
 11 38  1  0
 10 36  1  6
  5 31  1  6
  4 29  1  0
  4 30  1  0
  3 28  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 26 54  1  1
 27 55  1  0
 24 52  1  6
 25 53  1  0
 22 50  1  1
 23 51  1  0
M  END


  Mrv1652309062222282D          

 27 28  0  0  1  0            999 V2000
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  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
    1.4289   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0964   -5.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -6.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -6.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5315   -6.8870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615   -5.4349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0231   -5.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946   -4.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9793   -4.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5924   -4.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3770   -4.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9901   -4.9672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7747   -4.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3878   -5.2643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1724   -5.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7855   -5.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5701   -5.3064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3439   -4.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1286   -3.9474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7308   -3.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9024   -2.8434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9462   -3.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3331   -3.3533    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
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  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
  8 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  1  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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0237352

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OCC\C=C/C[C@H]2[C@H](CC(O)=O)CCC2=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H28O9/c19-9-13-15(23)16(24)17(25)18(27-13)26-7-3-1-2-4-11-10(8-14(21)22)5-6-12(11)20/h1-2,10-11,13,15-19,23-25H,3-9H2,(H,21,22)/b2-1-/t10-,11-,13?,15?,16?,17?,18?/m0/s1

> <INCHI_KEY>
JFDNMLUPLXZXGV-DKCJQCKPSA-N

> <FORMULA>
C18H28O9

> <MOLECULAR_WEIGHT>
388.413

> <EXACT_MASS>
388.173332482

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
39.485647288598756

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1S,2S)-3-oxo-2-[(2Z)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid

> <JCHEM_LOGP>
-0.7932033846666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.210972766837358

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.4626287129632365

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083411872574

> <JCHEM_POLAR_SURFACE_AREA>
153.75

> <JCHEM_REFRACTIVITY>
92.89850000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2S)-3-oxo-2-[(2Z)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.913 -10.145   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.437 -11.610   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.897 -11.610   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.992 -12.856   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.421 -10.145   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.043  -9.669   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.363  -8.163   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.828  -7.687   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.972  -8.718   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.437  -8.242   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.581  -9.272   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -7.046  -8.796   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -8.191  -9.827   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -9.655  -9.351   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -10.800 -10.381   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -12.264  -9.905   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -9.975  -7.844   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -11.440  -7.369   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -8.831  -6.814   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -9.151  -5.308   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -7.366  -7.290   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -6.222  -6.259   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   17   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
Tuberonate glucoside	Generator
Tuberonic acid beta-D-glucoside	MeSH

Chemical Formula

C₁₈H₂₈O₉

Average Mass

388.4130 Da

Monoisotopic Mass

388.17333 Da

IUPAC Name

2-[(1S,2S)-3-oxo-2-[(2Z)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid

Traditional Name

[(1S,2S)-3-oxo-2-[(2Z)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid

CAS Registry Number

Not Available

SMILES

OCC1OC(OCC\C=C/C[C@H]2[C@H](CC(O)=O)CCC2=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C18H28O9/c19-9-13-15(23)16(24)17(25)18(27-13)26-7-3-1-2-4-11-10(8-14(21)22)5-6-12(11)20/h1-2,10-11,13,15-19,23-25H,3-9H2,(H,21,22)/b2-1-/t10-,11-,13?,15?,16?,17?,18?/m0/s1

InChI Key

JFDNMLUPLXZXGV-DKCJQCKPSA-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
Phyllanthus emblica	LOTUS Database	35616633
Solanum tuberosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Jasmonic acid
Fatty acyl glycoside of mono- or disaccharide
Hexose monosaccharide
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Oxane
Monosaccharide
Cyclic ketone
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
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	-0.79	ChemAxon
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	92.9 m³·mol⁻¹	ChemAxon
Polarizability	39.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00001326

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

133554324

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fateh AH, Mohamed Z, Chik Z, Alsalahi A, Md Zin SR, Alshawsh MA: Prenatal developmental toxicity evaluation of Verbena officinalis during gestation period in female Sprague-Dawley rats. Chem Biol Interact. 2019 May 1;304:28-42. doi: 10.1016/j.cbi.2019.02.016. Epub 2019 Feb 23. [PubMed:30807743 ]
Hua Y, Ekkhara W, Sansenya S, Srisomsap C, Roytrakul S, Saburi W, Takeda R, Matsuura H, Mori H, Ketudat Cairns JR: Identification of rice Os4BGlu13 as a beta-glucosidase which hydrolyzes gibberellin A4 1-O-beta-d-glucosyl ester, in addition to tuberonic acid glucoside and salicylic acid derivative glucosides. Arch Biochem Biophys. 2015 Oct 1;583:36-46. doi: 10.1016/j.abb.2015.07.021. Epub 2015 Aug 1. [PubMed:26241499 ]
Sansenya S, Opassiri R, Kuaprasert B, Chen CJ, Cairns JR: The crystal structure of rice (Oryza sativa L.) Os4BGlu12, an oligosaccharide and tuberonic acid glucoside-hydrolyzing beta-glucosidase with significant thioglucohydrolase activity. Arch Biochem Biophys. 2011 Jun 1;510(1):62-72. doi: 10.1016/j.abb.2011.04.005. Epub 2011 Apr 16. [PubMed:21521631 ]
Quirantes-Pine R, Arraez-Roman D, Segura-Carretero A, Fernandez-Gutierrez A: Characterization of phenolic and other polar compounds in a lemon verbena extract by capillary electrophoresis-electrospray ionization-mass spectrometry. J Sep Sci. 2010 Sep;33(17-18):2818-27. doi: 10.1002/jssc.201000228. [PubMed:20715141 ]
Wakuta S, Hamada S, Ito H, Matsuura H, Nabeta K, Matsui H: Identification of a beta-glucosidase hydrolyzing tuberonic acid glucoside in rice (Oryza sativa L.). Phytochemistry. 2010 Aug;71(11-12):1280-8. doi: 10.1016/j.phytochem.2010.04.025. [PubMed:20570296 ]
LOTUS database [Link]

Showing NP-Card for [(1s,2s)-3-oxo-2-[(2z)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid (NP0237352)

MOL for NP0237352 ([(1s,2s)-3-oxo-2-[(2z)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid)

3D MOL for NP0237352 ([(1s,2s)-3-oxo-2-[(2z)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid)

3D SDF for NP0237352 ([(1s,2s)-3-oxo-2-[(2z)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid)

3D-SDF for NP0237352 ([(1s,2s)-3-oxo-2-[(2z)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid)

PDB for NP0237352 ([(1s,2s)-3-oxo-2-[(2z)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid)

3D PDB for NP0237352 ([(1s,2s)-3-oxo-2-[(2z)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid)

SMILES for NP0237352 ([(1s,2s)-3-oxo-2-[(2z)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid)

INCHI for NP0237352 ([(1s,2s)-3-oxo-2-[(2z)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid)

Structure for NP0237352 ([(1s,2s)-3-oxo-2-[(2z)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid)

3D Structure for NP0237352 ([(1s,2s)-3-oxo-2-[(2z)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-en-1-yl]cyclopentyl]acetic acid)