NP-MRD: Showing NP-Card for Deacetylnomilinate 17-glucoside (NP0084800)

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Record Information

Version

2.0

Created at

2022-04-29 05:26:44 UTC

Updated at

2022-04-29 05:26:44 UTC

NP-MRD ID

NP0084800

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Deacetylnomilinate 17-glucoside

Description

Deacetylnomilinic acid glucoside 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. Deacetylnomilinate 17-glucoside is found in Citrus aurantium and Citrus paradisi . Deacetylnomilinate 17-glucoside was first documented in 2009 (PMID: 19480426). Based on a literature review very few articles have been published on Deacetylnomilinic acid glucoside (PMID: 20864476).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207262D          

 48 52  0  0  1  0            999 V2000
    1.6982   -1.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2537   -1.2996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8092   -0.6896    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0597   -1.4757    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5587    0.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7527    0.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -2.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3102   -2.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8657   -1.6517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6716   -1.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8477   -1.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4956   -2.6338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4776   -2.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6151   -0.8657    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3920   -0.5879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8193   -0.0663    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2290    0.5101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6136    0.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8177    0.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2275    1.5324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6120    1.1789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9487   -2.6956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477   -1.1235    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2716   -1.9295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6616   -1.3740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1444   -1.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9693   -1.1933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998   -1.8079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1972   -0.3374    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5682    0.1964    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7160    1.0081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0871    1.5419    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6898    1.2641    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2864    0.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7999    3.1435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941    2.8874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.2349    2.3536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2086   -0.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405   -0.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2652   -0.8972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5429   -0.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900    0.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4029   -0.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
  9 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  1  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
  7 22  2  0  0  0  0
  2 23  1  0  0  0  0
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 24 25  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 23 29  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  6  0  0  0
 32 31  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
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 35 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
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 40 41  1  0  0  0  0
 39 42  1  0  0  0  0
 32 42  1  0  0  0  0
 30 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 43 47  1  0  0  0  0
 29 48  1  1  0  0  0
M  END

     RDKit          3D

 93 97  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652304292207262D          

 48 52  0  0  1  0            999 V2000
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    2.2537   -1.2996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8092   -0.6896    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0597   -1.4757    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5587    0.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7527    0.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -2.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3102   -2.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8657   -1.6517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6716   -1.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8477   -1.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4956   -2.6338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4776   -2.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6151   -0.8657    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3920   -0.5879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8193   -0.0663    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2290    0.5101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6136    0.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8177    0.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2275    1.5324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6120    1.1789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9487   -2.6956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477   -1.1235    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2716   -1.9295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6616   -1.3740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1444   -1.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9693   -1.1933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998   -1.8079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1972   -0.3374    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5682    0.1964    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7160    1.0081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0871    1.5419    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6898    1.2641    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2864    0.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3187    1.7980    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0956    1.5202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1709    2.6096    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7999    3.1435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941    2.8874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2462    3.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5306    3.9769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2349    2.3536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2086   -0.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405   -0.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2652   -0.8972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5429   -0.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900    0.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4029   -0.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
  9 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  1  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
  7 22  2  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 23 29  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  6  0  0  0
 32 31  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 39 42  1  0  0  0  0
 32 42  1  0  0  0  0
 30 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 43 47  1  0  0  0  0
 29 48  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0084800

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC[C@@](C)([C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C3=COC=C3)[C@@]3(O[C@@H]3C(O)=O)[C@]1(C)C(=O)C[C@@H](C(C)(C)O)[C@]2(C)[C@H](O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H46O15/c1-28(2,43)17-10-19(35)31(5)16(30(17,4)18(34)11-20(36)37)6-8-29(3,32(31)25(47-32)26(41)42)24(14-7-9-44-13-14)46-27-23(40)22(39)21(38)15(12-33)45-27/h7,9,13,15-18,21-25,27,33-34,38-40,43H,6,8,10-12H2,1-5H3,(H,36,37)(H,41,42)/t15-,16-,17+,18-,21-,22+,23-,24+,25-,27+,29+,30-,31+,32-/m1/s1

> <INCHI_KEY>
KHVQVGJVQGOROB-VIWLNRHZSA-N

> <FORMULA>
C32H46O15

> <MOLECULAR_WEIGHT>
670.705

> <EXACT_MASS>
670.283670781

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
93

> <JCHEM_AVERAGE_POLARIZABILITY>
66.4917033077354

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3'S,4aR,5R,6R,8aR)-5-[(1R)-2-carboxy-1-hydroxyethyl]-2-[(R)-(furan-3-yl)({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid

> <ALOGPS_LOGP>
0.75

> <JCHEM_LOGP>
-0.5235191696666701

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.427773928646798

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7364440084577795

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083688337913

> <JCHEM_POLAR_SURFACE_AREA>
257.17999999999995

> <JCHEM_REFRACTIVITY>
155.85229999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.99e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3'S,4aR,5R,6R,8aR)-5-[(1R)-2-carboxy-1-hydroxyethyl]-2-[(R)-furan-3-yl({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3H-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       3.170  -3.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.207  -2.426   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.244  -1.287   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0       5.711  -2.755   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0       4.776   0.180   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.272   0.509   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.674  -3.893   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.179  -4.222   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.216  -3.083   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.720  -3.412   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.049  -1.907   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.392  -4.916   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.225  -3.741   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.748  -1.616   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.198  -1.097   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.129  -0.124   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.028   0.952   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.612   0.292   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.993   1.784   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.891   2.860   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.476   2.201   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.638  -5.032   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.702  -2.097   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.374  -3.602   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.235  -2.565   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.269  -2.236   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.809  -2.227   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.306  -3.375   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.235  -0.630   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.061   0.367   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.337   1.882   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.163   2.878   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.288   2.360   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.401   1.296   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.462   3.356   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -3.912   2.838   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -2.186   4.871   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -3.360   5.868   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -0.736   5.390   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.460   6.905   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       0.990   7.423   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       0.438   4.393   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -0.389  -0.152   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -0.822  -1.630   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -2.362  -1.675   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -2.880  -0.225   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -1.661   0.716   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       0.752  -1.046   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   23                                             
CONECT    3    2    4    5   14                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5   29                                                       
CONECT    7    2    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    9    3   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    7                                                            
CONECT   23    2   24   25   29                                             
CONECT   24   23   25                                                       
CONECT   25   24   23   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   23    6   30   48                                             
CONECT   30   29   31   43                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   42                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   42                                                  
CONECT   40   39   41                                                       
CONECT   41   40                                                            
CONECT   42   39   32                                                       
CONECT   43   30   44   47                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   43                                                       
CONECT   48   29                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  104    0
END

View in JSmol

Synonyms

Value	Source
Deacetylnomilinate glucoside	Generator

Chemical Formula

C₃₂H₄₆O₁₅

Average Mass

670.7050 Da

Monoisotopic Mass

670.28367 Da

IUPAC Name

(1R,2S,3'S,4aR,5R,6R,8aR)-5-[(1R)-2-carboxy-1-hydroxyethyl]-2-[(R)-(furan-3-yl)({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid

Traditional Name

(1R,2S,3'S,4aR,5R,6R,8aR)-5-[(1R)-2-carboxy-1-hydroxyethyl]-2-[(R)-furan-3-yl({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3H-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@]12CC[C@@](C)([C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C3=COC=C3)[C@@]3(O[C@@H]3C(O)=O)[C@]1(C)C(=O)C[C@@H](C(C)(C)O)[C@]2(C)[C@H](O)CC(O)=O

InChI Identifier

InChI=1S/C32H46O15/c1-28(2,43)17-10-19(35)31(5)16(30(17,4)18(34)11-20(36)37)6-8-29(3,32(31)25(47-32)26(41)42)24(14-7-9-44-13-14)46-27-23(40)22(39)21(38)15(12-33)45-27/h7,9,13,15-18,21-25,27,33-34,38-40,43H,6,8,10-12H2,1-5H3,(H,36,37)(H,41,42)/t15-,16-,17+,18-,21-,22+,23-,24+,25-,27+,29+,30-,31+,32-/m1/s1

InChI Key

KHVQVGJVQGOROB-VIWLNRHZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Citrus aurantium	LOTUS Database	35616633
Citrus paradisi	Plant	KNApSAcK

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Saccharolipid
Terpene glycoside
Sesquiterpenoid
Glycosyl compound
O-glycosyl compound
Carbocyclic fatty acid
Beta-hydroxy acid
Hydroxy fatty acid
Fatty acyl
Dicarboxylic acid or derivatives
Hydroxy acid
Oxirane carboxylic acid or derivatives
Oxirane carboxylic acid
Oxane
Monosaccharide
Heteroaromatic compound
Tertiary alcohol
Furan
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Acetal
Polyol
Organic oxygen compound
Carbonyl group
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
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	0.75	ALOGPS
logP	-0.52	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.74	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	257.18 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	155.85 m³·mol⁻¹	ChemAxon
Polarizability	66.49 Å³	ChemAxon
Number of Rings	5	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

C00054395

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

102450060

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Vikram A, Jesudhasan PR, Jayaprakasha GK, Pillai SD, Patil BS: Citrus limonoids interfere with Vibrio harveyi cell-cell signalling and biofilm formation by modulating the response regulator LuxO. Microbiology (Reading). 2011 Jan;157(Pt 1):99-110. doi: 10.1099/mic.0.041228-0. Epub 2010 Sep 23. [PubMed:20864476 ]
Perez JL, Jayaprakasha GK, Valdivia V, Munoz D, Dandekar DV, Ahmad H, Patil BS: Limonin methoxylation influences the induction of glutathione S-transferase and quinone reductase. J Agric Food Chem. 2009 Jun 24;57(12):5279-86. doi: 10.1021/jf803712a. [PubMed:19480426 ]

Showing NP-Card for Deacetylnomilinate 17-glucoside (NP0084800)

MOL for NP0084800 (Deacetylnomilinate 17-glucoside)

3D MOL for NP0084800 (Deacetylnomilinate 17-glucoside)

3D SDF for NP0084800 (Deacetylnomilinate 17-glucoside)

3D-SDF for NP0084800 (Deacetylnomilinate 17-glucoside)

PDB for NP0084800 (Deacetylnomilinate 17-glucoside)

3D PDB for NP0084800 (Deacetylnomilinate 17-glucoside)

SMILES for NP0084800 (Deacetylnomilinate 17-glucoside)

INCHI for NP0084800 (Deacetylnomilinate 17-glucoside)

Structure for NP0084800 (Deacetylnomilinate 17-glucoside)

3D Structure for NP0084800 (Deacetylnomilinate 17-glucoside)