NP-MRD: Showing NP-Card for 5-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid (NP0216951)

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Record Information

Version

2.0

Created at

2022-09-05 17:07:13 UTC

Updated at

2022-09-05 17:07:13 UTC

NP-MRD ID

NP0216951

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid

Description

5-Methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. 5-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid is found in Bletilla striata and Dactylorhiza hatagirea. 5-Methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251508262D          

 43 45  0  0  0  0            999 V2000
   -1.6500   -3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645   -4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645   -5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789   -3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7934   -4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1803   -4.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3518   -5.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7388   -6.2275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6068   -6.4601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5079   -4.7289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5079   -5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7934   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7934   -6.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789   -7.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789   -8.0289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5079   -7.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5079   -8.0289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2224   -6.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9368   -7.2039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2224   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9368   -5.5539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2059   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7934   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7934   -0.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5559    0.6849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7934    1.3993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7934    2.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2059    3.5427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684    2.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    3.5427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5559   -0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684   -1.4586    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
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 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 31 40  1  0  0  0  0
 40 41  1  0  0  0  0
 29 42  1  0  0  0  0
 42 43  2  0  0  0  0
 26 43  1  0  0  0  0
M  END

     RDKit          3D

 83 85  0  0  0  0  0  0  0  0999 V2000
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   -4.2149   -3.1678   -0.4896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9275   -2.6172   -1.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1192   -2.3982    0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2909   -1.1648    0.8587 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2004   -1.3422    2.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2800   -0.0457    2.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1096   -1.0280    2.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0079   -0.8243    0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9893   -0.5044   -0.7476 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3896    1.1841   -1.2368 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7698    3.4738    0.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004251508262D          

 43 45  0  0  0  0            999 V2000
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   -3.3518   -5.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7934   -6.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789   -7.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789   -8.0289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5079   -7.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5079   -8.0289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2224   -6.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9368   -7.2039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2224   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9368   -5.5539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2059   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0309   -3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7934   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2059   -2.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7934   -1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2059   -0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7934   -0.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684   -0.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    0.6849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684    1.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7934    1.3993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2059    2.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0309    2.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4434    2.8283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7934    2.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2059    3.5427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684    2.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    3.5427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    2.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    2.1138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684   -1.4586    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 31 40  1  0  0  0  0
 40 41  1  0  0  0  0
 29 42  1  0  0  0  0
 42 43  2  0  0  0  0
 26 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0216951

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(CC(O)=O)(OC1OC(CO)C(O)C(O)C1O)C(=O)OCC1=CC=C(OC2OC(CO)C(O)C(O)C2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O16/c1-12(2)7-27(8-17(30)31,43-25-23(37)21(35)19(33)16(10-29)42-25)26(38)39-11-13-3-5-14(6-4-13)40-24-22(36)20(34)18(32)15(9-28)41-24/h3-6,12,15-16,18-25,28-29,32-37H,7-11H2,1-2H3,(H,30,31)

> <INCHI_KEY>
ZGNUJHGCJSHIQU-UHFFFAOYSA-N

> <FORMULA>
C27H40O16

> <MOLECULAR_WEIGHT>
620.601

> <EXACT_MASS>
620.231635208

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
60.9900051799354

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid

> <ALOGPS_LOGP>
-1.37

> <JCHEM_LOGP>
-1.8988672730000027

> <ALOGPS_LOGS>
-2.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.90460568080448

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9958696894349193

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343686494

> <JCHEM_POLAR_SURFACE_AREA>
262.35999999999996

> <JCHEM_REFRACTIVITY>
139.1824

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.53e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -3.080  -7.287   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.414  -8.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.414  -9.597   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.747  -7.287   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.081  -8.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.937  -9.088   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.257 -10.594   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.112 -11.625   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -6.733 -12.059   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -8.415  -8.827   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -8.415 -10.367   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -7.081 -11.137   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -7.081 -12.677   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.747 -13.447   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.747 -14.987   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -8.415 -13.447   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -8.415 -14.987   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -9.748 -12.677   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0     -11.082 -13.447   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -9.748 -11.137   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -11.082 -10.367   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -7.851  -6.724   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -9.391  -6.724   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -7.081  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -7.851  -4.056   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -7.081  -2.723   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.851  -1.389   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -7.081  -0.055   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.541  -0.055   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.771   1.278   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.541   2.612   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -7.081   2.612   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -7.851   3.946   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -9.391   3.946   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -10.161   5.279   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -7.081   5.279   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -7.851   6.613   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -5.541   5.279   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -4.771   6.613   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -4.771   3.946   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -3.231   3.946   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -4.771  -1.389   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -5.541  -2.723   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   10   22                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   11   21                                                  
CONECT   21   20                                                            
CONECT   22    5   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   43                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   42                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   40                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   31   41                                                  
CONECT   41   40                                                            
CONECT   42   29   43                                                       
CONECT   43   42   26                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

View in JSmol

Synonyms

Value	Source
5-Methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoate	Generator

Chemical Formula

C₂₇H₄₀O₁₆

Average Mass

620.6010 Da

Monoisotopic Mass

620.23164 Da

IUPAC Name

5-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid

Traditional Name

5-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)CC(CC(O)=O)(OC1OC(CO)C(O)C(O)C1O)C(=O)OCC1=CC=C(OC2OC(CO)C(O)C(O)C2O)C=C1

InChI Identifier

InChI=1S/C27H40O16/c1-12(2)7-27(8-17(30)31,43-25-23(37)21(35)19(33)16(10-29)42-25)26(38)39-11-13-3-5-14(6-4-13)40-24-22(36)20(34)18(32)15(9-28)41-24/h3-6,12,15-16,18-25,28-29,32-37H,7-11H2,1-2H3,(H,30,31)

InChI Key

ZGNUJHGCJSHIQU-UHFFFAOYSA-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
Bletilla striata	LOTUS Database	35616633
Orchis hatagirea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Mexicanolide
Prostaglandin skeleton
Steroid lactone
Eicosanoid
Hexacarboxylic acid or derivatives
Oxosteroid
2-oxosteroid
3-oxasteroid
Steroid
Naphthopyran
Naphthalene
Delta valerolactone
Delta_valerolactone
Fatty acyl
Oxane
Pyran
Tertiary alcohol
Methyl ester
Heteroaromatic compound
Furan
Cyclic alcohol
Lactone
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	-1.4	ALOGPS
logP	-1.9	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	262.36 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	139.18 m³·mol⁻¹	ChemAxon
Polarizability	60.99 Å³	ChemAxon
Number of Rings	3	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9986365

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid (NP0216951)

MOL for NP0216951 (5-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid)

3D MOL for NP0216951 (5-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid)

3D SDF for NP0216951 (5-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid)

3D-SDF for NP0216951 (5-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid)

PDB for NP0216951 (5-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid)

3D PDB for NP0216951 (5-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid)

SMILES for NP0216951 (5-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid)

INCHI for NP0216951 (5-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid)

Structure for NP0216951 (5-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid)

3D Structure for NP0216951 (5-methyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid)