NP-MRD: Showing NP-Card for 3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid (NP0194508)

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Record Information

Version

2.0

Created at

2022-09-04 12:10:34 UTC

Updated at

2022-09-04 12:10:34 UTC

NP-MRD ID

NP0194508

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid

Description

Licoagroside B, also known as tachiogroside b, 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. 3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid is found in Glycine max, Glycyrrhiza glabra and Helichrysum arenarium. 3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid was first documented in 2018 (PMID: 29783188). Based on a literature review very few articles have been published on licoagroside B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042214102D          

 30 31  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   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
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 O   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
   -2.8579   -4.9500    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
   -2.1434   -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
   -0.7145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  1  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
  1  2  1  0  0  0  0
  2  3  1  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  2  0  0  0  0
  6  8  1  0  0  0  0
  2  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 10 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END

     RDKit          3D

 54 55  0  0  0  0  0  0  0  0999 V2000
   -4.1455    1.7147    1.8776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2382    1.2512    0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4693    1.1730    1.3928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4616    0.7712    0.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2143    0.4082   -0.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9202    0.4774   -1.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6868    0.1508   -2.3195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8951    0.9005   -0.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5569    0.9997   -0.7395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6736   -0.1199   -0.5558 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7863    0.2109    0.4030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5931   -0.4881    0.4694 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1060   -0.2283    1.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3909   -0.7024    1.8919 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5557   -0.1579    1.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4749    0.8918    0.6929 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8793   -0.7892    1.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0105   -0.0570    0.8848 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2895   -0.8148    1.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0546    1.2385    1.3636 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8976   -0.0648   -0.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0249    0.6621   -1.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1572    0.1359   -1.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8481    1.9510   -1.7184 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1249   -0.4563   -0.8018 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3086   -1.2413   -0.7920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7898   -1.1107   -1.8577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1645   -1.1159   -3.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0685   -0.3889   -1.9046 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9824   -1.2260   -2.5958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6009    2.2764    2.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4365    2.3409    1.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6532    0.8353    2.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4775    0.7229    1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0490    0.0804   -1.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2883   -0.9549   -0.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9924   -1.5919    0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0789    0.8667    2.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5176   -0.7057    2.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1568   -0.8098    2.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8600   -1.8724    1.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5504   -1.4686    0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1278   -0.0735    1.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1363   -1.3873    2.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570    1.3861    2.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9669    0.4174   -0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9428   -1.1432   -0.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1809    2.7639   -1.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3837    0.5420   -1.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6206   -1.2960   -1.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9668   -2.1388   -1.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6859   -1.7351   -3.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9594    0.5346   -2.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2110   -1.9593   -1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  1
 18 21  1  0
 21 22  1  0
 22 24  1  0
 22 23  2  0
 12 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
 29 10  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 10 36  1  1
 12 37  1  1
 13 38  1  0
 13 39  1  0
 17 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 24 48  1  0
 25 49  1  6
 26 50  1  0
 27 51  1  1
 28 52  1  0
 29 53  1  6
 30 54  1  0
  5 35  1  0
  4 34  1  0
M  END


  Mrv1652309042214102D          

 30 31  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   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
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 O   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
   -2.8579   -4.9500    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
   -2.1434   -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
   -0.7145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  1  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
  1  2  1  0  0  0  0
  2  3  1  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  2  0  0  0  0
  6  8  1  0  0  0  0
  2  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 10 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0194508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O[C@@H]2O[C@H](COC(=O)CC(C)(O)CC(O)=O)[C@@H](O)[C@H](O)[C@H]2O)C(=O)C=CO1

> <INCHI_IDENTIFIER>
InChI=1S/C18H24O12/c1-8-16(9(19)3-4-27-8)30-17-15(25)14(24)13(23)10(29-17)7-28-12(22)6-18(2,26)5-11(20)21/h3-4,10,13-15,17,23-26H,5-7H2,1-2H3,(H,20,21)/t10-,13-,14+,15-,17+,18?/m1/s1

> <INCHI_KEY>
WCVUIHQUPRXYKT-RGCIIANRSA-N

> <FORMULA>
C18H24O12

> <MOLECULAR_WEIGHT>
432.378

> <EXACT_MASS>
432.126776213

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
40.22288619564588

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-methyl-4-oxo-4H-pyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid

> <JCHEM_LOGP>
-1.838476957000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.200338125491346

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.753163151531036

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0083920901482806

> <JCHEM_POLAR_SURFACE_AREA>
189.27999999999997

> <JCHEM_REFRACTIVITY>
96.78080000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -6.668 -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  C   UNK     0      -4.565 -10.574   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.105  -7.906   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334  -8.470   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.667 -10.780   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   29                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   12   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   10   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid	ChEBI
Maltol 3-O-[6-O-(3-hydroxy-3-methylglutaroyl)]-beta-D-glucopyranoside	ChEBI
Tachiogroside b	ChEBI
3-Hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoate	Generator
Maltol 3-O-[6-O-(3-hydroxy-3-methylglutaroyl)]-b-D-glucopyranoside	Generator
Maltol 3-O-[6-O-(3-hydroxy-3-methylglutaroyl)]-β-D-glucopyranoside	Generator

Chemical Formula

C₁₈H₂₄O₁₂

Average Mass

432.3780 Da

Monoisotopic Mass

432.12678 Da

IUPAC Name

3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-methyl-4-oxo-4H-pyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid

Traditional Name

3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid

CAS Registry Number

Not Available

SMILES

CC1=C(O[C@@H]2O[C@H](COC(=O)CC(C)(O)CC(O)=O)[C@@H](O)[C@H](O)[C@H]2O)C(=O)C=CO1

InChI Identifier

InChI=1S/C18H24O12/c1-8-16(9(19)3-4-27-8)30-17-15(25)14(24)13(23)10(29-17)7-28-12(22)6-18(2,26)5-11(20)21/h3-4,10,13-15,17,23-26H,5-7H2,1-2H3,(H,20,21)/t10-,13-,14+,15-,17+,18?/m1/s1

InChI Key

WCVUIHQUPRXYKT-RGCIIANRSA-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
Glycine max	LOTUS Database	35616633
Glycyrrhiza glabra	LOTUS Database	35616633
Helichrysum arenarium	LOTUS Database	35616633

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
Glycosyl compound
O-glycosyl compound
Fatty acid ester
Pyranone
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Pyran
Fatty acyl
Heteroaromatic compound
Tertiary alcohol
Secondary alcohol
Cyclic ketone
Carboxylic acid ester
Oxacycle
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Carboxylic acid
Acetal
Carbonyl group
Organic oxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	-1.8	ChemAxon
pKa (Strongest Acidic)	3.75	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	96.78 m³·mol⁻¹	ChemAxon
Polarizability	40.22 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00019031

Chemspider ID

20057435

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22297602

PDB ID

Not Available

ChEBI ID

142266

Good Scents ID

Not Available

References

General References

Kozachok S, Pecio L, Kolodziejczyk-Czepas J, Marchyshyn S, Nowak P, Moldoch J, Oleszek W: gamma-Pyrone compounds: flavonoids and maltol glucoside derivatives from Herniaria glabra L. collected in the Ternopil region of the Ukraine. Phytochemistry. 2018 Aug;152:213-222. doi: 10.1016/j.phytochem.2018.05.009. Epub 2018 May 21. [PubMed:29783188 ]
LOTUS database [Link]

Showing NP-Card for 3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid (NP0194508)

MOL for NP0194508 (3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid)

3D MOL for NP0194508 (3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid)

3D SDF for NP0194508 (3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid)

3D-SDF for NP0194508 (3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid)

PDB for NP0194508 (3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid)

3D PDB for NP0194508 (3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid)

SMILES for NP0194508 (3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid)

INCHI for NP0194508 (3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid)

Structure for NP0194508 (3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid)

3D Structure for NP0194508 (3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[(2-methyl-4-oxopyran-3-yl)oxy]oxan-2-yl]methoxy}pentanoic acid)