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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:11:51 UTC

Update Date

2022-03-07 02:55:57 UTC

HMDB ID

HMDB0038850

Secondary Accession Numbers

HMDB38850

Metabolite Identification

Common Name

Cycasin

Description

Allolactose 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. Allolactose is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0038850
     RDKit          3D
Cycasin
 33 33  0  0  0  0  0  0  0  0999 V2000
    5.3034    1.0363    0.6316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8641    0.9243    0.4023 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.9517    1.2563    1.3618 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.5288    0.4931   -0.7618 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1553    0.3269   -1.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3498   -0.0051   -0.0443 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0359   -0.1446   -0.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7560    0.6942    0.2289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0842    0.7029   -0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8296    1.6238    0.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2013    2.8785    0.6578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7284   -0.6422   -0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1042   -1.0616    1.0999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8501   -1.7136   -0.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3513   -2.9659   -0.4380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4149   -1.5921   -0.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2507   -1.9699    1.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4642    1.0588    1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7772    0.1511    0.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6543    1.9742    0.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.5174   -1.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7083    1.2246   -1.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0287    0.0386   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1206    1.1127   -1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9001    1.6622    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6350    1.3126    1.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7809    3.5459    0.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6594   -0.5862   -0.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4331   -0.8215    1.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8857   -1.6196   -1.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1145   -3.2328    0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1854   -2.2528   -1.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1197   -2.8918    1.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
M  CHG  2   2   1   3  -1
M  END


  Mrv0541 05061310422D          

 17 17  0  0  0  0            999 V2000
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  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  3  1  0  0  0  0
 10  1  1  0  0  0  0
 10  9  2  0  0  0  0
 11  2  1  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15 10  2  0  0  0  0
 16  3  1  0  0  0  0
 16  8  1  0  0  0  0
 17  4  1  0  0  0  0
 17  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038850

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(=O)=NCOC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C8H16N2O7/c1-10(15)9-3-16-8-7(14)6(13)5(12)4(2-11)17-8/h4-8,11-14H,2-3H2,1H3/b10-9-

> <INCHI_KEY>
YHLRMABUJXBLCK-KTKRTIGZSA-N

> <FORMULA>
C8H16N2O7

> <MOLECULAR_WEIGHT>
252.2218

> <EXACT_MASS>
252.095750876

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
23.39099998409579

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(hydroxymethyl)-6-{[(methyl-oxo-λ⁵-azanylidene)amino]methoxy}oxane-3,4,5-triol

> <ALOGPS_LOGP>
-2.55

> <JCHEM_LOGP>
-3.190500557666667

> <ALOGPS_LOGS>
-0.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.19908507373373

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.207967404060254

> <JCHEM_PKA_STRONGEST_BASIC>
4.156954711299811

> <JCHEM_POLAR_SURFACE_AREA>
140.48999999999998

> <JCHEM_REFRACTIVITY>
52.0523

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.66e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(hydroxymethyl)-6-{[(methyl-oxo-λ⁵-azanylidene)amino]methoxy}oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038850
     RDKit          3D
Cycasin
 33 33  0  0  0  0  0  0  0  0999 V2000
    5.3034    1.0363    0.6316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8641    0.9243    0.4023 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.9517    1.2563    1.3618 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.5288    0.4931   -0.7618 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1553    0.3269   -1.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3498   -0.0051   -0.0443 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0359   -0.1446   -0.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7560    0.6942    0.2289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0842    0.7029   -0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8296    1.6238    0.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2013    2.8785    0.6578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7284   -0.6422   -0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1042   -1.0616    1.0999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8501   -1.7136   -0.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3513   -2.9659   -0.4380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4149   -1.5921   -0.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2507   -1.9699    1.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4642    1.0588    1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7772    0.1511    0.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6543    1.9742    0.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.5174   -1.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7083    1.2246   -1.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0287    0.0386   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1206    1.1127   -1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9001    1.6622    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6350    1.3126    1.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7809    3.5459    0.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6594   -0.5862   -0.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4331   -0.8215    1.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8857   -1.6196   -1.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1145   -3.2328    0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1854   -2.2528   -1.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1197   -2.8918    1.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
M  CHG  2   2   1   3  -1
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000  -4.620   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      -1.334  -5.390   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2    4   11                                                       
CONECT    3    9   16                                                       
CONECT    4    2    5   17                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7   16   17                                                  
CONECT    9    3   10                                                       
CONECT   10    1    9   15                                                  
CONECT   11    2                                                            
CONECT   12    5                                                            
CONECT   13    6                                                            
CONECT   14    7                                                            
CONECT   15   10                                                            
CONECT   16    3    8                                                       
CONECT   17    4    8                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0038850
HETATM    1  C1  UNL     1       5.303   1.036   0.632  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.864   0.924   0.402  1.00  0.00           N1+
HETATM    3  O1  UNL     1       2.952   1.256   1.362  1.00  0.00           O1-
HETATM    4  N2  UNL     1       3.529   0.493  -0.762  1.00  0.00           N  
HETATM    5  C2  UNL     1       2.155   0.327  -1.143  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.350  -0.005  -0.044  1.00  0.00           O  
HETATM    7  C3  UNL     1       0.036  -0.145  -0.520  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.756   0.694   0.229  1.00  0.00           O  
HETATM    9  C4  UNL     1      -2.084   0.703  -0.182  1.00  0.00           C  
HETATM   10  C5  UNL     1      -2.830   1.624   0.793  1.00  0.00           C  
HETATM   11  O4  UNL     1      -2.201   2.879   0.658  1.00  0.00           O  
HETATM   12  C6  UNL     1      -2.728  -0.642  -0.174  1.00  0.00           C  
HETATM   13  O5  UNL     1      -3.104  -1.062   1.100  1.00  0.00           O  
HETATM   14  C7  UNL     1      -1.850  -1.714  -0.764  1.00  0.00           C  
HETATM   15  O6  UNL     1      -2.351  -2.966  -0.438  1.00  0.00           O  
HETATM   16  C8  UNL     1      -0.415  -1.592  -0.322  1.00  0.00           C  
HETATM   17  O7  UNL     1      -0.251  -1.970   1.008  1.00  0.00           O  
HETATM   18  H1  UNL     1       5.464   1.059   1.731  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.777   0.151   0.187  1.00  0.00           H  
HETATM   20  H3  UNL     1       5.654   1.974   0.146  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.031  -0.517  -1.873  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.708   1.225  -1.601  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.029   0.039  -1.614  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.121   1.113  -1.205  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.900   1.662   0.591  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.635   1.313   1.839  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.781   3.546   0.249  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.659  -0.586  -0.774  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.433  -0.822   1.788  1.00  0.00           H  
HETATM   30  H13 UNL     1      -1.886  -1.620  -1.865  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.114  -3.233   0.492  1.00  0.00           H  
HETATM   32  H15 UNL     1       0.185  -2.253  -1.003  1.00  0.00           H  
HETATM   33  H16 UNL     1       0.120  -2.892   1.075  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4    4
CONECT    4    5
CONECT    5    6   21   22
CONECT    6    7
CONECT    7    8   16   23
CONECT    8    9
CONECT    9   10   12   24
CONECT   10   11   25   26
CONECT   11   27
CONECT   12   13   14   28
CONECT   13   29
CONECT   14   15   16   30
CONECT   15   31
CONECT   16   17   32
CONECT   17   33
END

HMDB0038850
     RDKit          3D
Cycasin
 33 33  0  0  0  0  0  0  0  0999 V2000
    5.3034    1.0363    0.6316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8641    0.9243    0.4023 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.9517    1.2563    1.3618 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.5288    0.4931   -0.7618 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1553    0.3269   -1.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3498   -0.0051   -0.0443 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0359   -0.1446   -0.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7560    0.6942    0.2289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0842    0.7029   -0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8296    1.6238    0.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2013    2.8785    0.6578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7284   -0.6422   -0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1042   -1.0616    1.0999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8501   -1.7136   -0.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3513   -2.9659   -0.4380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4149   -1.5921   -0.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2507   -1.9699    1.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4642    1.0588    1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7772    0.1511    0.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6543    1.9742    0.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.5174   -1.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7083    1.2246   -1.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0287    0.0386   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1206    1.1127   -1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9001    1.6622    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6350    1.3126    1.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7809    3.5459    0.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6594   -0.5862   -0.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4331   -0.8215    1.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8857   -1.6196   -1.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1145   -3.2328    0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1854   -2.2528   -1.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1197   -2.8918    1.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
M  CHG  2   2   1   3  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2-Hydroxy-2-methyl-2beta -D-glucosyloxyazoxymethane	HMDB
b-D-Glucosyloxyazoxymethane	HMDB
beta -D-Glucopyranoside, (methyl-ONN-azoxy)methyl	HMDB
Cycas revoluta glucoside	HMDB
Cykazine	HMDB
Methylazoxymethanol beta -D-glucoside	HMDB
Methylazoxymethanol glucoside	HMDB
Methylazoxymethanolbeta -D-glucoside	HMDB
(Methyl-ONN-azoxy)methyl beta-D-glucopyranoside	MeSH, HMDB
Glucuronate, methylazoxymethanol	MeSH, HMDB
Methylazoxymethanol glucuronate	MeSH, HMDB
Methylazoxymethanol beta D glucoside	MeSH, HMDB
Methylazoxymethanol beta-D-glucoside	MeSH, HMDB
beta-D-Glucoside, methylazoxymethanol	MeSH, HMDB
Cycasin	MeSH

Chemical Formula

C₈H₁₆N₂O₇

Average Molecular Weight

252.2218

Monoisotopic Molecular Weight

252.095750876

IUPAC Name

2-(hydroxymethyl)-6-{[(methyl-oxo-λ⁵-azanylidene)amino]methoxy}oxane-3,4,5-triol

Traditional Name

2-(hydroxymethyl)-6-{[(methyl-oxo-λ⁵-azanylidene)amino]methoxy}oxane-3,4,5-triol

CAS Registry Number

14901-08-7

SMILES

CN(=O)=NCOC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C8H16N2O7/c1-10(15)9-3-16-8-7(14)6(13)5(12)4(2-11)17-8/h4-8,11-14H,2-3H2,1H3/b10-9-

InChI Key

YHLRMABUJXBLCK-KTKRTIGZSA-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
Disaccharide
O-glycosyl compound
Glycosyl compound
Beta-hydroxy aldehyde
Oxane
Alpha-hydroxyaldehyde
Tetrahydrofuran
Secondary alcohol
Hemiacetal
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Organooxygen compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aldehyde
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Not Available

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	154 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	56.6 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.2	ChemAxon
logS	-0.65	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	4.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	140.49 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.05 m³·mol⁻¹	ChemAxon
Polarizability	23.39 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	153.763	30932474
DeepCCS	[M-H]-	151.405	30932474
DeepCCS	[M-2H]-	185.715	30932474
DeepCCS	[M+Na]+	160.34	30932474
AllCCS	[M+H]+	154.3	32859911
AllCCS	[M+H-H2O]+	150.7	32859911
AllCCS	[M+NH4]+	157.7	32859911
AllCCS	[M+Na]+	158.7	32859911
AllCCS	[M-H]-	152.0	32859911
AllCCS	[M+Na-2H]-	152.0	32859911
AllCCS	[M+HCOO]-	152.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cycasin	CN(=O)=NCOC1OC(CO)C(O)C(O)C1O	3440.7	Standard polar	33892256
Cycasin	CN(=O)=NCOC1OC(CO)C(O)C(O)C1O	2345.0	Standard non polar	33892256
Cycasin	CN(=O)=NCOC1OC(CO)C(O)C(O)C1O	2127.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cycasin,1TMS,isomer #1	C[N+]([O-])=NCOC1OC(CO[Si](C)(C)C)C(O)C(O)C1O	2189.2	Semi standard non polar	33892256
Cycasin,1TMS,isomer #2	C[N+]([O-])=NCOC1OC(CO)C(O[Si](C)(C)C)C(O)C1O	2168.2	Semi standard non polar	33892256
Cycasin,1TMS,isomer #3	C[N+]([O-])=NCOC1OC(CO)C(O)C(O[Si](C)(C)C)C1O	2147.2	Semi standard non polar	33892256
Cycasin,1TMS,isomer #4	C[N+]([O-])=NCOC1OC(CO)C(O)C(O)C1O[Si](C)(C)C	2152.3	Semi standard non polar	33892256
Cycasin,2TMS,isomer #1	C[N+]([O-])=NCOC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O	2201.6	Semi standard non polar	33892256
Cycasin,2TMS,isomer #2	C[N+]([O-])=NCOC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O	2202.5	Semi standard non polar	33892256
Cycasin,2TMS,isomer #3	C[N+]([O-])=NCOC1OC(CO[Si](C)(C)C)C(O)C(O)C1O[Si](C)(C)C	2191.1	Semi standard non polar	33892256
Cycasin,2TMS,isomer #4	C[N+]([O-])=NCOC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O	2170.5	Semi standard non polar	33892256
Cycasin,2TMS,isomer #5	C[N+]([O-])=NCOC1OC(CO)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C	2171.6	Semi standard non polar	33892256
Cycasin,2TMS,isomer #6	C[N+]([O-])=NCOC1OC(CO)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2167.6	Semi standard non polar	33892256
Cycasin,3TMS,isomer #1	C[N+]([O-])=NCOC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O	2231.4	Semi standard non polar	33892256
Cycasin,3TMS,isomer #2	C[N+]([O-])=NCOC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C	2257.0	Semi standard non polar	33892256
Cycasin,3TMS,isomer #3	C[N+]([O-])=NCOC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2223.3	Semi standard non polar	33892256
Cycasin,3TMS,isomer #4	C[N+]([O-])=NCOC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2216.6	Semi standard non polar	33892256
Cycasin,4TMS,isomer #1	C[N+]([O-])=NCOC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2276.2	Semi standard non polar	33892256
Cycasin,1TBDMS,isomer #1	C[N+]([O-])=NCOC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O	2412.4	Semi standard non polar	33892256
Cycasin,1TBDMS,isomer #2	C[N+]([O-])=NCOC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	2397.0	Semi standard non polar	33892256
Cycasin,1TBDMS,isomer #3	C[N+]([O-])=NCOC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O	2385.9	Semi standard non polar	33892256
Cycasin,1TBDMS,isomer #4	C[N+]([O-])=NCOC1OC(CO)C(O)C(O)C1O[Si](C)(C)C(C)(C)C	2395.2	Semi standard non polar	33892256
Cycasin,2TBDMS,isomer #1	C[N+]([O-])=NCOC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	2640.1	Semi standard non polar	33892256
Cycasin,2TBDMS,isomer #2	C[N+]([O-])=NCOC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O	2642.9	Semi standard non polar	33892256
Cycasin,2TBDMS,isomer #3	C[N+]([O-])=NCOC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O[Si](C)(C)C(C)(C)C	2637.3	Semi standard non polar	33892256
Cycasin,2TBDMS,isomer #4	C[N+]([O-])=NCOC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O	2631.1	Semi standard non polar	33892256
Cycasin,2TBDMS,isomer #5	C[N+]([O-])=NCOC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C	2629.3	Semi standard non polar	33892256
Cycasin,2TBDMS,isomer #6	C[N+]([O-])=NCOC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	2631.0	Semi standard non polar	33892256
Cycasin,3TBDMS,isomer #1	C[N+]([O-])=NCOC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O	2878.9	Semi standard non polar	33892256
Cycasin,3TBDMS,isomer #2	C[N+]([O-])=NCOC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C	2892.9	Semi standard non polar	33892256
Cycasin,3TBDMS,isomer #3	C[N+]([O-])=NCOC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	2867.9	Semi standard non polar	33892256
Cycasin,3TBDMS,isomer #4	C[N+]([O-])=NCOC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	2853.5	Semi standard non polar	33892256
Cycasin,4TBDMS,isomer #1	C[N+]([O-])=NCOC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3098.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cycasin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0h5r-9850000000-3ae79e36d7b7a3e090ce	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cycasin GC-MS (4 TMS) - 70eV, Positive	splash10-004i-9000760000-b350e12e80c5a64f2924	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cycasin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycasin 10V, Positive-QTOF	splash10-000i-3090000000-19f2d0d91e8917e29604	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycasin 20V, Positive-QTOF	splash10-004u-9140000000-9389db4aa9cad9ab70e5	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycasin 40V, Positive-QTOF	splash10-0006-9220000000-890302a816c15fbbc59c	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycasin 10V, Negative-QTOF	splash10-0f79-3290000000-693da4f26853aa2678dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycasin 20V, Negative-QTOF	splash10-054x-9440000000-c030d7e270a9e1923845	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycasin 40V, Negative-QTOF	splash10-0006-9300000000-f0a64372d5343f3c1093	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycasin 10V, Positive-QTOF	splash10-0udj-4290000000-dab40db05cddba32104d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycasin 20V, Positive-QTOF	splash10-006w-9210000000-045abc302fac26225e78	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycasin 40V, Positive-QTOF	splash10-0a4i-9000000000-040fc93954dfd4504202	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycasin 10V, Negative-QTOF	splash10-0udi-2390000000-1cc076ed764d4f391535	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycasin 20V, Negative-QTOF	splash10-0006-9320000000-eb05cde49a57379db841	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycasin 40V, Negative-QTOF	splash10-0006-9100000000-08add1f5d16d8c289142	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB017861

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Allolactose

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Cycasin (HMDB0038850)

MOL for HMDB0038850 (Cycasin)

3D MOL for HMDB0038850 (Cycasin)

3D SDF for HMDB0038850 (Cycasin)

3D-SDF for HMDB0038850 (Cycasin)

PDB for HMDB0038850 (Cycasin)

3D PDB for HMDB0038850 (Cycasin)

SMILES for HMDB0038850 (Cycasin)

INCHI for HMDB0038850 (Cycasin)

Structure for HMDB0038850 (Cycasin)

3D Structure for HMDB0038850 (Cycasin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra