NP-MRD: Showing NP-Card for 1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r,3s)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate (NP0331025)

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Record Information

Version

2.0

Created at

2022-09-12 16:57:28 UTC

Updated at

2022-09-12 16:57:29 UTC

NP-MRD ID

NP0331025

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r,3s)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate

Description

Loroglossin belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. 1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r,3s)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate is found in Cremastra appendiculata, Gymnadenia conopsea and Dactylorhiza hatagirea. 1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r,3s)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate was first documented in 2004 (PMID: 14989381). Based on a literature review a significant number of articles have been published on Loroglossin (PMID: 21322946) (PMID: 19894516) (PMID: 19772750) (PMID: 18507346) (PMID: 16934540).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122218572D          

 52 55  0  0  1  0            999 V2000
    9.7006   -3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -5.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717   -3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -4.3974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9697   -5.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -4.3974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -5.6349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -6.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -6.8724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -7.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -8.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -8.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -9.3474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -9.7599    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4138  -10.5849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993  -10.9974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6993  -11.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849  -12.2349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849  -10.5849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2704  -10.9974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -9.7599    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2704   -9.3474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -9.3474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6993   -8.5224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -8.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -7.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -3.6829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3197   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3822   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3197   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822    1.3184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6697    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822    2.7474    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6697    3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447    3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072    2.7474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3197    3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3197    2.0329    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072    1.3184    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3197    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3197   -0.8250    0.0000 C   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
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
 14 27  1  0  0  0  0
 27 28  2  0  0  0  0
 11 28  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  6  0  0  0
 43 44  1  0  0  0  0
 42 45  1  0  0  0  0
 45 46  1  1  0  0  0
 45 47  1  0  0  0  0
 47 48  1  6  0  0  0
 47 49  1  0  0  0  0
 40 49  1  0  0  0  0
 49 50  1  1  0  0  0
 38 51  1  0  0  0  0
 51 52  2  0  0  0  0
 35 52  1  0  0  0  0
M  END


  Mrv1652309122218572D          

 52 55  0  0  1  0            999 V2000
    9.7006   -3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -5.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717   -3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -4.3974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9697   -5.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -4.3974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -5.6349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -6.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -6.8724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -7.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -8.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -8.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -9.3474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -9.7599    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4138  -10.5849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993  -10.9974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6993  -11.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849  -12.2349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849  -10.5849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2704  -10.9974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -9.7599    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2704   -9.3474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -9.3474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6993   -8.5224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -8.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -7.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -3.6829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3197   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3822   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3197   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822    1.3184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6697    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822    2.7474    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6697    3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447    3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072    2.7474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3197    3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3197    2.0329    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072    1.3184    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3197    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3197   -0.8250    0.0000 C   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
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
 14 27  1  0  0  0  0
 27 28  2  0  0  0  0
 11 28  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  6  0  0  0
 43 44  1  0  0  0  0
 42 45  1  0  0  0  0
 45 46  1  1  0  0  0
 45 47  1  0  0  0  0
 47 48  1  6  0  0  0
 47 49  1  0  0  0  0
 40 49  1  0  0  0  0
 49 50  1  1  0  0  0
 38 51  1  0  0  0  0
 51 52  2  0  0  0  0
 35 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331025

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@@](O)([C@H](O)C(=O)OCC1=CC=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1)C(=O)OCC1=CC=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C34H46O18/c1-16(2)11-34(46,33(45)48-15-18-5-9-20(10-6-18)50-32-28(42)26(40)24(38)22(13-36)52-32)29(43)30(44)47-14-17-3-7-19(8-4-17)49-31-27(41)25(39)23(37)21(12-35)51-31/h3-10,16,21-29,31-32,35-43,46H,11-15H2,1-2H3/t21-,22-,23-,24-,25+,26+,27-,28-,29-,31-,32-,34-/m1/s1

> <INCHI_KEY>
QABASLXUKXNHMC-PIFIRMJRSA-N

> <FORMULA>
C34H46O18

> <MOLECULAR_WEIGHT>
742.724

> <EXACT_MASS>
742.268414641

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
73.29067273210731

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,4-bis[(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2R,3S)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate

> <JCHEM_LOGP>
-1.5444563296666671

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.805209991188121

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.914738584422341

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648395345629174

> <JCHEM_POLAR_SURFACE_AREA>
291.82

> <JCHEM_REFRACTIVITY>
171.61430000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
loroglossin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      18.108  -7.438   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.774  -8.208   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.774  -9.748   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.440  -7.438   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.107  -8.208   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.877  -9.542   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      12.773  -8.978   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.439  -8.208   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      12.773 -10.518   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      11.439 -11.288   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.439 -12.828   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.773 -13.598   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.773 -15.138   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.439 -15.908   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.439 -17.448   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.106 -18.218   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.106 -19.758   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.772 -20.528   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.772 -22.068   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.438 -22.838   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.438 -19.758   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.105 -20.528   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.438 -18.218   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.105 -17.448   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.772 -17.448   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.772 -15.908   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.106 -15.138   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.106 -13.598   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.337  -6.875   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      11.797  -6.875   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      14.107  -5.541   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      15.647  -5.541   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      13.337  -4.207   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      11.797  -4.207   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.027  -2.874   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.487  -2.874   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.717  -1.540   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.487  -0.206   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       8.717   1.127   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       9.487   2.461   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       8.717   3.795   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       9.487   5.128   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       8.717   6.462   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       7.177   6.462   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      11.027   5.128   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      11.797   6.462   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      11.797   3.795   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      13.337   3.795   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      11.027   2.461   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      11.797   1.127   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      11.027  -0.206   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      11.797  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   29                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   28                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25                                                            
CONECT   27   14   28                                                       
CONECT   28   27   11                                                       
CONECT   29    5   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   52                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   51                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   49                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   45                                                  
CONECT   43   42   44                                                       
CONECT   44   43                                                            
CONECT   45   42   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   40   50                                                  
CONECT   50   49                                                            
CONECT   51   38   52                                                       
CONECT   52   51   35                                                       
MASTER        0    0    0    0    0    0    0    0   52    0  110    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₄₆O₁₈

Average Mass

742.7240 Da

Monoisotopic Mass

742.26841 Da

IUPAC Name

1,4-bis[(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2R,3S)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate

Traditional Name

loroglossin

CAS Registry Number

Not Available

SMILES

CC(C)C[C@@](O)([C@H](O)C(=O)OCC1=CC=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1)C(=O)OCC1=CC=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1

InChI Identifier

InChI=1S/C34H46O18/c1-16(2)11-34(46,33(45)48-15-18-5-9-20(10-6-18)50-32-28(42)26(40)24(38)22(13-36)52-32)29(43)30(44)47-14-17-3-7-19(8-4-17)49-31-27(41)25(39)23(37)21(12-35)51-31/h3-10,16,21-29,31-32,35-43,46H,11-15H2,1-2H3/t21-,22-,23-,24-,25+,26+,27-,28-,29-,31-,32-,34-/m1/s1

InChI Key

QABASLXUKXNHMC-PIFIRMJRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cremastra appendiculata	LOTUS Database	35616633
Gymnadenia conopsea	LOTUS Database	35616633
Orchis hatagirea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Benzyloxycarbonyl
Phenoxy compound
Phenol ether
Beta-hydroxy acid
Fatty acid ester
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Hydroxy acid
Monosaccharide
Oxane
Benzenoid
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Organic oxide
Alcohol
Hydrocarbon derivative
Carbonyl group
Primary alcohol
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	-1.5	ChemAxon
pKa (Strongest Acidic)	10.91	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	291.82 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	171.61 m³·mol⁻¹	ChemAxon
Polarizability	73.29 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00030690

Chemspider ID

161601

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

185907

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yue Z, Zi J, Zhu C, Lin S, Yang Y, Shi J: [Constituents of Gymnadenia conopsea]. Zhongguo Zhong Yao Za Zhi. 2010 Nov;35(21):2852-61. [PubMed:21322946 ]
Yang B, Li S, Zhang R, Wang Y, Shi J: [Quantitative analysis of four active constituents in Tibetan herb Gymnadenia conopsea by high-performance liquid chromatography]. Zhongguo Zhong Yao Za Zhi. 2009 Jul;34(14):1819-22. [PubMed:19894516 ]
Li M, Guo SX, Wang CL, Xiao PG: Quantitative determination of five glucosyloxybenzyl 2-isobutylmalates in the tubers of Gymnadenia conopsea and Coeloglossum viride var. bracteatum by HPLC. J Chromatogr Sci. 2009 Sep;47(8):709-13. doi: 10.1093/chromsci/47.8.709. [PubMed:19772750 ]
Liu J, Yu ZB, Ye YH, Zhou YW: [Chemical constituents from the tuber of Cremastra appendiculata]. Yao Xue Xue Bao. 2008 Feb;43(2):181-4. [PubMed:18507346 ]
Cai M, Zhou Y, Gesang S, Bianba C, Ding LS: Chemical fingerprint analysis of rhizomes of Gymnadenia conopsea by HPLC-DAD-MSn. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Dec 5;844(2):301-7. doi: 10.1016/j.jchromb.2006.07.043. Epub 2006 Aug 23. [PubMed:16934540 ]
Huang SY, Li GQ, Shi JG, Mo SY: Chemical constituents of the rhizomes of Coeloglossum viride var. bracteatum. J Asian Nat Prod Res. 2004 Mar;6(1):49-61. doi: 10.1080/1028602031000119826. [PubMed:14989381 ]
LOTUS database [Link]

Showing NP-Card for 1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r,3s)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate (NP0331025)

MOL for NP0331025 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r,3s)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate)

3D MOL for NP0331025 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r,3s)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate)

3D SDF for NP0331025 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r,3s)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate)

3D-SDF for NP0331025 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r,3s)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate)

PDB for NP0331025 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r,3s)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate)

3D PDB for NP0331025 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r,3s)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate)

SMILES for NP0331025 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r,3s)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate)

INCHI for NP0331025 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r,3s)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate)

Structure for NP0331025 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r,3s)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate)

3D Structure for NP0331025 (1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r,3s)-2,3-dihydroxy-2-(2-methylpropyl)butanedioate)