NP-MRD: Showing NP-Card for (13r)-13-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid (NP0180984)

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Record Information

Version

2.0

Created at

2022-09-03 19:25:47 UTC

Updated at

2022-09-03 19:25:47 UTC

NP-MRD ID

NP0180984

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(13r)-13-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid

Description

(13R)-13-{[(2R,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid belongs to the class of organic compounds known as sophorolipids. These are glycolipids containing a sophorose moiety linked glycosidically to the hydroxyl group of a 17-hydroxy-C18 saturated fatty acid. The carboxyl group of the fatty acid can be linked to the 4'-hydroxyl of the second glucose to form a lactone. (13r)-13-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid is found in Pseudohyphozyma bogoriensis. Based on a literature review very few articles have been published on (13R)-13-{[(2R,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032221252D          

 53 54  0  0  1  0            999 V2000
   -2.6835   -9.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4135   -7.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8734   -7.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033   -5.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8734   -5.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333   -4.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033   -3.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632   -3.0497    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2531   -3.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0169   -3.9852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8271   -4.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0971   -4.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9073   -5.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1773   -5.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9874   -6.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2575   -6.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0676   -6.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3377   -7.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1478   -7.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4178   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2280   -8.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8777   -9.2861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333   -2.2702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.1143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6835   -2.7379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4936   -2.5820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0337   -3.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8439   -3.0497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3839   -3.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1139   -4.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1941   -3.5175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7637   -1.8024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5738   -1.6465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2236   -1.1788    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4936   -0.3993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4135   -1.3347    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8734   -0.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.0685    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9535    0.2244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2236    1.0039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0337    1.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5738    0.5362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3839    0.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9240    0.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6540    1.4717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6835    1.6276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9535    2.4071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8734    1.4717    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3333    2.0953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033    0.6921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7932    0.5362    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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 10 25  1  1  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 28 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 26 38  1  0  0  0  0
 38 39  1  1  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
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  2  0  0  0  0
 42 48  1  0  0  0  0
 48 49  1  1  0  0  0
 48 50  1  0  0  0  0
 50 51  1  6  0  0  0
 50 52  1  0  0  0  0
 40 52  1  0  0  0  0
 52 53  1  1  0  0  0
M  END

     RDKit          3D

121122  0  0  0  0  0  0  0  0999 V2000
    4.8892   -5.2541    2.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3878   -3.8618    2.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2625   -1.3041    4.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2583   -0.1157    3.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8476    0.5287    1.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4718    0.8081    1.1795 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3905    1.4141    2.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1732    2.6981    2.7542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4431    3.4737    3.8213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7739    4.0576    3.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9775    3.2065    3.5316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132    2.1784    4.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4685    1.4049    4.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4074    0.6513    3.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6899   -0.1472    2.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9038    0.7172    2.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7680    1.7028    1.5623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6312    1.0778    0.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4170    1.8125   -0.7629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7316   -0.2879    0.0486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2861   -0.1037    0.4570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9163    0.3995   -0.6752 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.9622   -0.8223   -0.7319 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.6387    0.4377   -2.5128 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7616   -0.1214   -3.0554 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.3121    1.3656   -1.9115 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6483    2.3940   -1.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3172    3.7076   -1.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4886    2.2378   -0.9046 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3429    2.2024   -3.9534 O   0  0  0  0  0  0  0  0  0  0  0  0
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 48116  1  1
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 53121  1  0
M  END


  Mrv1652309032221252D          

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 50 52  1  0  0  0  0
 40 52  1  0  0  0  0
 52 53  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0180984

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCC[C@H](CCCCCCCCCCCC(O)=O)O[C@@H]1O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C38H68O15/c1-4-5-6-7-11-14-17-20-27(21-18-15-12-9-8-10-13-16-19-22-30(41)42)50-38-36(34(46)32(44)29(52-38)24-49-26(3)40)53-37-35(47)33(45)31(43)28(51-37)23-48-25(2)39/h27-29,31-38,43-47H,4-24H2,1-3H3,(H,41,42)/t27-,28-,29-,31-,32-,33+,34+,35-,36-,37+,38-/m1/s1

> <INCHI_KEY>
LGIFCELMJBBHMO-AOGHEHALSA-N

> <FORMULA>
C38H68O15

> <MOLECULAR_WEIGHT>
764.947

> <EXACT_MASS>
764.45582149

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
121

> <JCHEM_AVERAGE_POLARIZABILITY>
86.48119651789776

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(13R)-13-{[(2R,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid

> <JCHEM_LOGP>
4.87785577

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.092285730583939

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952019624194835

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649085064414308

> <JCHEM_POLAR_SURFACE_AREA>
227.96999999999994

> <JCHEM_REFRACTIVITY>
189.48870000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
30

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(13R)-13-{[(2R,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.009 -17.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.505 -14.715   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.497 -13.551   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001 -12.096   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.993 -10.931   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.497  -9.476   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.489  -8.312   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.993  -6.857   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.985  -5.693   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.472  -5.984   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.032  -7.439   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.544  -7.730   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.048  -9.185   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.560  -9.476   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.064 -10.931   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.577 -11.222   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.081 -12.678   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.593 -12.969   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.097 -14.424   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.609 -14.715   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.113 -16.170   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.626 -16.461   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.105 -17.334   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.489  -4.238   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.001  -3.947   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.009  -5.111   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -6.521  -4.820   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -7.530  -5.984   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -9.042  -5.693   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0     -10.050  -6.857   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -9.546  -8.312   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -11.562  -6.566   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -7.026  -3.365   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -8.538  -3.074   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -6.017  -2.200   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.521  -0.745   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -4.505  -2.491   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -3.497  -1.327   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -4.001   0.128   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -5.513   0.419   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -6.017   1.874   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -7.530   2.165   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -8.538   1.001   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0     -10.050   1.292   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -11.058   0.128   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0     -10.554   2.747   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -5.009   3.038   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -5.513   4.493   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -3.497   2.747   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -2.489   3.911   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      -2.993   1.292   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -1.481   1.001   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   25                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   10   26                                                       
CONECT   26   25   27   38                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   34                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   28   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   26   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   52                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   48                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   42   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   40   53                                                  
CONECT   53   52                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  108    0
END

View in JSmol

Synonyms

Value	Source
(13R)-13-{[(2R,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoate	Generator

Chemical Formula

C₃₈H₆₈O₁₅

Average Mass

764.9470 Da

Monoisotopic Mass

764.45582 Da

IUPAC Name

(13R)-13-{[(2R,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid

Traditional Name

(13R)-13-{[(2R,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCC[C@H](CCCCCCCCCCCC(O)=O)O[C@@H]1O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C38H68O15/c1-4-5-6-7-11-14-17-20-27(21-18-15-12-9-8-10-13-16-19-22-30(41)42)50-38-36(34(46)32(44)29(52-38)24-49-26(3)40)53-37-35(47)33(45)31(43)28(51-37)23-48-25(2)39/h27-29,31-38,43-47H,4-24H2,1-3H3,(H,41,42)/t27-,28-,29-,31-,32-,33+,34+,35-,36-,37+,38-/m1/s1

InChI Key

LGIFCELMJBBHMO-AOGHEHALSA-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
Pseudohyphozyma bogoriensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sophorolipids. These are glycolipids containing a sophorose moiety linked glycosidically to the hydroxyl group of a 17-hydroxy-C18 saturated fatty acid. The carboxyl group of the fatty acid can be linked to the 4'-hydroxyl of the second glucose to form a lactone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Sophorolipids

Alternative Parents

Substituents

Sophorolipid
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Disaccharide
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Oxane
Secondary alcohol
Carboxylic acid ester
Oxacycle
Polyol
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Carboxylic acid
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.88	ChemAxon
pKa (Strongest Acidic)	4.95	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	227.97 Å²	ChemAxon
Rotatable Bond Count	30	ChemAxon
Refractivity	189.49 m³·mol⁻¹	ChemAxon
Polarizability	86.48 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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

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

162959182

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (13r)-13-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid (NP0180984)

MOL for NP0180984 ((13r)-13-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid)

3D MOL for NP0180984 ((13r)-13-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid)

3D SDF for NP0180984 ((13r)-13-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid)

3D-SDF for NP0180984 ((13r)-13-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid)

PDB for NP0180984 ((13r)-13-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid)

3D PDB for NP0180984 ((13r)-13-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid)

SMILES for NP0180984 ((13r)-13-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid)

INCHI for NP0180984 ((13r)-13-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid)

Structure for NP0180984 ((13r)-13-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid)

3D Structure for NP0180984 ((13r)-13-{[(2r,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}docosanoic acid)