MiMeDB: Showing metabocard for SB 253518 (MMDBc0019466)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 09:31:36 UTC

Update Date

2022-08-31 06:45:28 UTC

Metabolite ID

MMDBc0019466

Metabolite Identification

Common Name

SB 253518

Description

SB 253518 belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. SB 253518 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152111312D          

 51 53  0  0  1  0            999 V2000
   -1.4071  -11.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7376   -6.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6927  -11.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0218  -11.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363  -11.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4508  -11.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1652  -11.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8797  -11.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5942  -11.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086  -11.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0231  -11.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7376  -11.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4521  -11.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6791   -7.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4521  -10.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1271   -8.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4328   -8.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8810  -10.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7389  -10.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7376   -7.6547    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1665  -10.1297    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5396   -9.3092    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4534  -10.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5955  -10.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0244  -10.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0231   -8.0672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0231   -8.8922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7376   -9.3047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4521   -8.8922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.7591   -9.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3099  -10.5422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3466   -9.1377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5955   -9.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0244   -9.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086   -7.6547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086   -9.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7376  -10.1297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5795   -9.9384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4521   -8.0672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1665   -9.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2070  -10.4653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1665  -11.7797    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4521   -9.7172    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7389  -11.3672    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0231   -7.2422    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1665  -10.9547    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7326   -9.4808    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086   -8.4797    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7376   -8.4797    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0231   -9.7172    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1665   -8.4797    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 15 13  2  0  0  0  0
 16 14  1  0  0  0  0
 17 14  1  0  0  0  0
 20  2  1  6  0  0  0
 21 15  1  0  0  0  0
 21 18  1  0  0  0  0
 22 16  1  0  0  0  0
 23 19  2  0  0  0  0
 23 22  1  0  0  0  0
 24 18  1  0  0  0  0
 25 19  1  0  0  0  0
 26 20  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 28  1  0  0  0  0
 31 24  2  0  0  0  0
 31 25  1  4  0  0  0
 32 17  1  0  0  0  0
 32 22  1  0  0  0  0
 32 30  1  0  0  0  0
 33 24  1  0  0  0  0
 34 25  2  0  0  0  0
 26 35  1  1  0  0  0
 27 36  1  1  0  0  0
 28 37  1  6  0  0  0
 38 30  2  0  0  0  0
 39 20  1  0  0  0  0
 39 29  1  0  0  0  0
 21 40  1  1  0  0  0
 29 40  1  1  0  0  0
 41 23  1  0  0  0  0
 41 30  1  0  0  0  0
 42 13  1  0  0  0  0
 43 15  1  0  0  0  0
 44 19  1  0  0  0  0
 20 45  1  1  0  0  0
 21 46  1  1  0  0  0
 22 47  1  6  0  0  0
 26 48  1  6  0  0  0
 27 49  1  1  0  0  0
 28 50  1  1  0  0  0
 29 51  1  6  0  0  0
M  END


  Mrv1652305152111312D          

 51 53  0  0  1  0            999 V2000
   -1.4071  -11.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7376   -6.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6927  -11.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0218  -11.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363  -11.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4508  -11.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1652  -11.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8797  -11.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5942  -11.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086  -11.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0231  -11.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7376  -11.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4521  -11.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6791   -7.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4521  -10.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1271   -8.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4328   -8.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8810  -10.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7389  -10.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7376   -7.6547    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1665  -10.1297    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5396   -9.3092    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4534  -10.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5955  -10.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0244  -10.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0231   -8.0672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0231   -8.8922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7376   -9.3047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4521   -8.8922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.7591   -9.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3099  -10.5422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3466   -9.1377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5955   -9.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0244   -9.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086   -7.6547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086   -9.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7376  -10.1297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5795   -9.9384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4521   -8.0672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1665   -9.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2070  -10.4653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1665  -11.7797    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4521   -9.7172    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7389  -11.3672    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0231   -7.2422    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1665  -10.9547    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7326   -9.4808    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086   -8.4797    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7376   -8.4797    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0231   -9.7172    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1665   -8.4797    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 15 13  2  0  0  0  0
 16 14  1  0  0  0  0
 17 14  1  0  0  0  0
 20  2  1  6  0  0  0
 21 15  1  0  0  0  0
 21 18  1  0  0  0  0
 22 16  1  0  0  0  0
 23 19  2  0  0  0  0
 23 22  1  0  0  0  0
 24 18  1  0  0  0  0
 25 19  1  0  0  0  0
 26 20  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 28  1  0  0  0  0
 31 24  2  0  0  0  0
 31 25  1  4  0  0  0
 32 17  1  0  0  0  0
 32 22  1  0  0  0  0
 32 30  1  0  0  0  0
 33 24  1  0  0  0  0
 34 25  2  0  0  0  0
 26 35  1  1  0  0  0
 27 36  1  1  0  0  0
 28 37  1  6  0  0  0
 38 30  2  0  0  0  0
 39 20  1  0  0  0  0
 39 29  1  0  0  0  0
 21 40  1  1  0  0  0
 29 40  1  1  0  0  0
 41 23  1  0  0  0  0
 41 30  1  0  0  0  0
 42 13  1  0  0  0  0
 43 15  1  0  0  0  0
 44 19  1  0  0  0  0
 20 45  1  1  0  0  0
 21 46  1  1  0  0  0
 22 47  1  6  0  0  0
 26 48  1  6  0  0  0
 27 49  1  1  0  0  0
 28 50  1  1  0  0  0
 29 51  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0019466

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(CCCCCCCCCCC)=C([H])[C@@]([H])(CC(O)=NC(=O)C(\[H])=C1\OC(=O)N2CCC[C@]12[H])O[C@]1([H])O[C@@]([H])(C)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48N2O9/c1-3-4-5-6-7-8-9-10-11-12-13-15-21(40-29-28(37)27(36)26(35)20(2)39-29)18-24(33)31-25(34)19-23-22-16-14-17-32(22)30(38)41-23/h13,15,19-22,26-29,35-37H,3-12,14,16-18H2,1-2H3,(H,31,33,34)/b15-13+,23-19+/t20-,21-,22+,26-,27+,28+,29-/m0/s1

> <INCHI_KEY>
LVTDKRIMXLJUAE-JTQWKVPKSA-N

> <FORMULA>
C30H48N2O9

> <MOLECULAR_WEIGHT>
580.719

> <EXACT_MASS>
580.335981134

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
63.88044529650715

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4E)-N-{2-[(1E,7aR)-3-oxo-hexahydropyrrolo[1,2-c][1,3]oxazol-1-ylidene]acetyl}-3-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexadec-4-enimidic acid

> <ALOGPS_LOGP>
3.69

> <JCHEM_LOGP>
3.8450827763333315

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.22390822048191

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.213285203171741

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6293277869322247

> <JCHEM_POLAR_SURFACE_AREA>
158.34999999999997

> <JCHEM_REFRACTIVITY>
152.70080000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4E)-N-{2-[(1E,7aR)-3-oxo-tetrahydropyrrolo[1,2-c][1,3]oxazol-1-ylidene]acetyl}-3-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexadec-4-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      -2.627 -21.989   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.710 -12.749   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.293 -21.219   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.041 -21.989   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.374 -21.219   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.708 -21.989   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.042 -21.219   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.375 -21.989   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.709 -21.219   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.043 -21.989   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.376 -21.219   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.710 -21.989   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.044 -21.219   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.801 -14.899   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.044 -19.679   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.771 -16.044   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.208 -15.526   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.711 -19.679   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.046 -19.679   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.710 -14.289   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.378 -18.909   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.541 -17.377   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.380 -18.909   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.045 -18.909   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.712 -18.909   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.376 -15.059   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.376 -16.599   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.710 -17.369   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.044 -16.599   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      23.817 -18.391   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      17.379 -19.679   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0      23.047 -17.057   0.000  0.00  0.00           N+0
HETATM   33  O   UNK     0      16.045 -17.369   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      18.712 -17.369   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       8.043 -14.289   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       8.043 -17.369   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      10.710 -18.909   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      25.348 -18.552   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      12.044 -15.059   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      13.378 -17.369   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      22.786 -19.535   0.000  0.00  0.00           O+0
HETATM   42  H   UNK     0      13.378 -21.989   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0      12.044 -18.139   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0      20.046 -21.219   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0       9.376 -13.519   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      13.378 -20.449   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      20.034 -17.697   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0       8.043 -15.829   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0      10.710 -15.829   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0       9.376 -18.139   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0      13.378 -15.829   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2   20                                                            
CONECT    3    1    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                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   15   42                                                  
CONECT   14   16   17                                                       
CONECT   15   13   21   43                                                  
CONECT   16   14   22                                                       
CONECT   17   14   32                                                       
CONECT   18   21   24                                                       
CONECT   19   23   25   44                                                  
CONECT   20    2   26   39   45                                             
CONECT   21   15   18   40   46                                             
CONECT   22   16   23   32   47                                             
CONECT   23   19   22   41                                                  
CONECT   24   18   31   33                                                  
CONECT   25   19   31   34                                                  
CONECT   26   20   27   35   48                                             
CONECT   27   26   28   36   49                                             
CONECT   28   27   29   37   50                                             
CONECT   29   28   39   40   51                                             
CONECT   30   32   38   41                                                  
CONECT   31   24   25                                                       
CONECT   32   17   22   30                                                  
CONECT   33   24                                                            
CONECT   34   25                                                            
CONECT   35   26                                                            
CONECT   36   27                                                            
CONECT   37   28                                                            
CONECT   38   30                                                            
CONECT   39   20   29                                                       
CONECT   40   21   29                                                       
CONECT   41   23   30                                                       
CONECT   42   13                                                            
CONECT   43   15                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   26                                                            
CONECT   49   27                                                            
CONECT   50   28                                                            
CONECT   51   29                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  106    0
END

Synonyms

Not Available

Molecular Formula

C₃₀H₄₈N₂O₉

Average Mass

580.719

Monoisotopic Mass

580.335981134

IUPAC Name

(3R,4E)-N-{2-[(1E,7aR)-3-oxo-hexahydropyrrolo[1,2-c][1,3]oxazol-1-ylidene]acetyl}-3-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexadec-4-enimidic acid

Traditional Name

(3R,4E)-N-{2-[(1E,7aR)-3-oxo-tetrahydropyrrolo[1,2-c][1,3]oxazol-1-ylidene]acetyl}-3-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexadec-4-enimidic acid

CAS Registry Number

Not Available

SMILES

[H]C(CCCCCCCCCCC)=C([H])[C@@]([H])(CC(O)=NC(=O)C(\[H])=C1\OC(=O)N2CCC[C@]12[H])O[C@]1([H])O[C@@]([H])(C)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O

InChI Identifier

InChI=1S/C30H48N2O9/c1-3-4-5-6-7-8-9-10-11-12-13-15-21(40-29-28(37)27(36)26(35)20(2)39-29)18-24(33)31-25(34)19-23-22-16-14-17-32(22)30(38)41-23/h13,15,19-22,26-29,35-37H,3-12,14,16-18H2,1-2H3,(H,31,33,34)/b15-13+,23-19+/t20-,21-,22+,26-,27+,28+,29-/m0/s1

InChI Key

LVTDKRIMXLJUAE-JTQWKVPKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide
N-acyl-amine
Oxane
Oxazolidinone
Carboxylic acid imide
Dicarboximide
Enol ester
Carboxylic acid imide, n-unsubstituted
Oxazolidine
Carbamic acid ester
Pyrrolidine
Secondary alcohol
Carbonic acid derivative
Azacycle
Acetal
Oxacycle
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Organonitrogen compound
Organic oxygen compound
Alcohol
Organooxygen compound
Organopnictogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.028 g/L	ALOGPS
logP	3.69	ALOGPS
logP	3.85	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	7.21	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	158.35 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	152.7 m³·mol⁻¹	ChemAxon
Polarizability	63.88 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

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human subgingival plaque	Metabolic reconstruction

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78442781

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139588501

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for SB 253518 (MMDBc0019466)

MOL for #<Metabolite:0x00007fdb707c3910>

3D MOL for #<Metabolite:0x00007fdb707c3910>

3D SDF for #<Metabolite:0x00007fdb707c3910>

3D-SDF for #<Metabolite:0x00007fdb707c3910>

PDB for #<Metabolite:0x00007fdb707c3910>

3D PDB for #<Metabolite:0x00007fdb707c3910>

SMILES for #<Metabolite:0x00007fdb707c3910>

INCHI for #<Metabolite:0x00007fdb707c3910>

Structure for #<Metabolite:0x00007fdb707c3910>

3D Structure for #<Metabolite:0x00007fdb707c3910>