Np mrd loader

Showing NP-Card for myo-Inositol (NP0000748)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:41:26 UTC
NP-MRD IDNP0000748
Secondary Accession NumbersNone
Natural Product Identification
Common Namemyo-Inositol
DescriptionMyo-Inositol is an inositol isoform. Inositol is a derivative of cyclohexane with six hydroxyl groups, making it a polyol. It also is known as a sugar alcohol, having exactly the same molecular formula as glucose or other hexoses. Inositol exists in nine possible stereoisomers, of which cis-1,2,3,5-trans-4,6-cyclohexanehexol, or myo-inositol is the most widely occurring form in nature. The other known inositols include scyllo-inositol, muco-inositol, D-chiro-inositol, L-chiro-inositol, neo-inositol, allo-inositol, epi-inositol and cis-inositol. Myo-Inositol is found naturally in many foods (particularly in cereals with high bran content) and can be used as a sweetner as it has half the sweetness of sucrose (table sugar). Myo-Inositol was once considered a member of the vitamin B complex and given the name: Vitamin B8. However, because it is produced by the human body from glucose, it is not an essential nutrient, and therefore cannot be called a vitamin. Myo-Inositol is a precursor molecule for a number of secondary messengers including various inositol phosphates. In addition, inositol/myo-inositol is an important component of the lipids known as phosphatidylinositol (PI) phosphatidylinositol phosphate (PIP). Myo-Inositol is synthesized from glucose, via glucose-6-phosphate (G-6-P) in two steps. First, G-6-P is isomerised by an inositol-3-phosphate synthase enzyme to myo-inositol 1-phosphate, which is then dephosphorylated by an inositol monophosphatase enzyme to give free myo-inositol. In humans, myo-inositol is primarily synthesized in the kidneys at a rate of a few grams per day. Myo-Inositol can be used in the management of preterm babies who have or are at a risk of infant respiratory distress syndrome. It is also used as a treatment for polycystic ovary syndrome (PCOS). It works by increasing insulin sensitivity, which helps to improve ovarian function and reduce hyperandrogenism. Reduced levels of myo-inositol have been found in the spinal fluid of depressed patients and levels are significantly reduced in brain samples of suicide victims.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000748 (myo-Inositol)


  Mrv1652309032023572D          

 12 12  0  0  0  0            999 V2000
   -1.4275    0.8257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285   -0.8241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4261    0.8240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4271   -0.8223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012   -1.6481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7157    0.4132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7158   -0.4118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0011   -0.8244    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7133   -0.4118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7134    0.4132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0012    0.8258    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0011    1.6481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  6 11  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
  6  1  1  1  0  0  0
  7  2  1  6  0  0  0
  8  5  1  1  0  0  0
  9  4  1  6  0  0  0
 10  3  1  6  0  0  0
 11 12  1  6  0  0  0
M  END
Download

3D MOL for NP0000748 (myo-Inositol)

HMDB0000211
     RDKit          3D
myo-Inositol
 24 24  0  0  0  0  0  0  0  0999 V2000
   -2.5586    0.8634   -0.4667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4638    0.5151    0.3261 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0406   -0.8853   -0.0476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9983   -1.7617    0.4583 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2844   -1.2589    0.5708 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5999   -2.5389    0.1277 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3287   -0.2924    0.0713 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5870   -0.6252    0.5437 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9706    1.0760    0.5837 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9147    2.0155    0.2181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721    1.5143    0.0671 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3141    1.8309   -1.2767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4373    0.4087   -1.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8254    0.5339    1.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9554   -0.9635   -1.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6849   -1.3126    1.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2378   -1.2859    1.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6685   -2.5717   -0.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3380   -0.3579   -1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5020   -1.1700    1.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9663    1.0277    1.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6969    1.6207   -0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6329    2.4582    0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886    1.1593   -1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11  2  1  0
  1 13  1  0
  2 14  1  1
  3 15  1  6
  4 16  1  0
  5 17  1  1
  6 18  1  0
  7 19  1  6
  8 20  1  0
  9 21  1  1
 10 22  1  0
 11 23  1  1
 12 24  1  0
M  END
Download

3D SDF for NP0000748 (myo-Inositol)


  Mrv1652309032023572D          

 12 12  0  0  0  0            999 V2000
   -1.4275    0.8257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285   -0.8241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4261    0.8240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4271   -0.8223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012   -1.6481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7157    0.4132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7158   -0.4118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0011   -0.8244    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7133   -0.4118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7134    0.4132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0012    0.8258    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0011    1.6481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  6 11  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
  6  1  1  1  0  0  0
  7  2  1  6  0  0  0
  8  5  1  1  0  0  0
  9  4  1  6  0  0  0
 10  3  1  6  0  0  0
 11 12  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0000748

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4+,5-,6-

> <INCHI_KEY>
CDAISMWEOUEBRE-GPIVLXJGSA-N

> <FORMULA>
C6H12O6

> <MOLECULAR_WEIGHT>
180.1559

> <EXACT_MASS>
180.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.141745963720343

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol

> <ALOGPS_LOGP>
-2.59

> <JCHEM_LOGP>
-3.782009652

> <ALOGPS_LOGS>
0.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.908097249605351

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.285497953856298

> <JCHEM_PKA_STRONGEST_BASIC>
-3.645759838065448

> <JCHEM_POLAR_SURFACE_AREA>
121.38000000000001

> <JCHEM_REFRACTIVITY>
35.77499999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.85e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-inositol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000748 (myo-Inositol)

HMDB0000211
     RDKit          3D
myo-Inositol
 24 24  0  0  0  0  0  0  0  0999 V2000
   -2.5586    0.8634   -0.4667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4638    0.5151    0.3261 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0406   -0.8853   -0.0476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9983   -1.7617    0.4583 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2844   -1.2589    0.5708 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5999   -2.5389    0.1277 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3287   -0.2924    0.0713 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5870   -0.6252    0.5437 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9706    1.0760    0.5837 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9147    2.0155    0.2181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721    1.5143    0.0671 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3141    1.8309   -1.2767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4373    0.4087   -1.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8254    0.5339    1.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9554   -0.9635   -1.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6849   -1.3126    1.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2378   -1.2859    1.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6685   -2.5717   -0.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3380   -0.3579   -1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5020   -1.1700    1.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9663    1.0277    1.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6969    1.6207   -0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6329    2.4582    0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886    1.1593   -1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11  2  1  0
  1 13  1  0
  2 14  1  1
  3 15  1  6
  4 16  1  0
  5 17  1  1
  6 18  1  0
  7 19  1  6
  8 20  1  0
  9 21  1  1
 10 22  1  0
 11 23  1  1
 12 24  1  0
M  END
Download

PDB for NP0000748 (myo-Inositol)

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  O   UNK     0      -2.665   1.541   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -2.667  -1.538   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       2.662   1.538   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.664  -1.535   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -0.002  -3.076   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.336   0.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.336  -0.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.002  -1.539   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.331  -0.769   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.332   0.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.002   1.541   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.002   3.076   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3   10                                                            
CONECT    4    9                                                            
CONECT    5    8                                                            
CONECT    6    7   11    1                                                  
CONECT    7    6    8    2                                                  
CONECT    8    7    9    5                                                  
CONECT    9    8   10    4                                                  
CONECT   10    9   11    3                                                  
CONECT   11    6   10   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
Download

3D PDB for NP0000748 (myo-Inositol)

COMPND    HMDB0000211
HETATM    1  O1  UNL     1      -2.559   0.863  -0.467  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.464   0.515   0.326  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.041  -0.885  -0.048  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.998  -1.762   0.458  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.284  -1.259   0.571  1.00  0.00           C  
HETATM    6  O3  UNL     1       0.600  -2.539   0.128  1.00  0.00           O  
HETATM    7  C4  UNL     1       1.329  -0.292   0.071  1.00  0.00           C  
HETATM    8  O4  UNL     1       2.587  -0.625   0.544  1.00  0.00           O  
HETATM    9  C5  UNL     1       0.971   1.076   0.584  1.00  0.00           C  
HETATM   10  O5  UNL     1       1.915   2.016   0.218  1.00  0.00           O  
HETATM   11  C6  UNL     1      -0.372   1.514   0.067  1.00  0.00           C  
HETATM   12  O6  UNL     1      -0.314   1.831  -1.277  1.00  0.00           O  
HETATM   13  H1  UNL     1      -2.437   0.409  -1.346  1.00  0.00           H  
HETATM   14  H2  UNL     1      -1.825   0.534   1.377  1.00  0.00           H  
HETATM   15  H3  UNL     1      -0.955  -0.963  -1.144  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.685  -1.313   1.000  1.00  0.00           H  
HETATM   17  H5  UNL     1       0.238  -1.286   1.670  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.669  -2.572  -0.850  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.338  -0.358  -1.027  1.00  0.00           H  
HETATM   20  H8  UNL     1       2.502  -1.170   1.355  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.966   1.028   1.690  1.00  0.00           H  
HETATM   22  H10 UNL     1       2.697   1.621  -0.223  1.00  0.00           H  
HETATM   23  H11 UNL     1      -0.633   2.458   0.610  1.00  0.00           H  
HETATM   24  H12 UNL     1       0.189   1.159  -1.794  1.00  0.00           H  
CONECT    1    2   13
CONECT    2    3   11   14
CONECT    3    4    5   15
CONECT    4   16
CONECT    5    6    7   17
CONECT    6   18
CONECT    7    8    9   19
CONECT    8   20
CONECT    9   10   11   21
CONECT   10   22
CONECT   11   12   23
CONECT   12   24
END
Download

SMILES for NP0000748 (myo-Inositol)

O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O
Download

INCHI for NP0000748 (myo-Inositol)

InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4+,5-,6-
Download
View in JSmol
Synonyms
ValueSource
(1R,2R,3S,4S,5R,6S)-Cyclohexane-1,2,3,4,5,6-hexolChEBI
1,2,3,4,5,6-HEXAHYDROXY-cyclohexaneChEBI
1,2,3,5/4,6-cyclohexanehexolChEBI
1D-Myo-inositolChEBI
1l-Myo-inositolChEBI
Bios IChEBI
cis-1,2,3,5-trans-4,6-CyclohexanehexolChEBI
CyclohexitolChEBI
D-Myo-inositolChEBI
DamboseChEBI
I-inositolChEBI
InositeChEBI
InositolChEBI
InsChEBI
L-Myo-inositolChEBI
Meat sugarChEBI
Meso-inositolChEBI
MyoinositolChEBI
InositalKegg
Iso-inositolHMDB
MIHMDB
MyoinositeHMDB
PhaseomanniteHMDB
Rat antispectacled eye factorHMDB
Myo inositolHMDB
Vitamin b8HMDB
Myo-inositolHMDB
Chemical FormulaC6H12O6
Average Mass180.1559 Da
Monoisotopic Mass180.06339 Da
IUPAC Name(1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol
Traditional NameL-inositol
CAS Registry Number87-89-8
SMILES
O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4+,5-,6-
InChI KeyCDAISMWEOUEBRE-GPIVLXJGSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-11View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-08-07View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Agave americanaLOTUS Database
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
    • Graeme A. King, Kate G. Henderson, Erin M. O'Donoghue, Wilhelmina Martin, Ross E. Lill. Flavour a...
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaKNApSAcK Database
Basella albaFooDB
Benincasa hispidaFooDB
Bergera koenegii-
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaKNApSAcK Database
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Campanula persicifoliaLOTUS Database
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papayaKNApSAcK Database
Carica papaya L.Plant
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Centella asiaticaLOTUS Database
Centrosema pubescensKNApSAcK Database
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus sinensisKNApSAcK Database
Citrus X sinensis (L.) Osbeck (pro. sp.)Plant
Cocos nuciferaFooDB
Coffea arabicaKNApSAcK Database
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma domesticaKNApSAcK Database
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Dalbergia sissooKNApSAcK Database
Daphnia magnaLOTUS Database
Daphnia pulexLOTUS Database
Daucus carotaKNApSAcK Database
Daucus carota ssp. sativusFooDB
Desmodium intortumKNApSAcK Database
Desmodium uncinatumKNApSAcK Database
Detarium microcarpumLOTUS Database
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Euodia fargesiiLOTUS Database
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Homo sapiensLOTUS Database
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusKNApSAcK Database
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lemna aequinoctialisLOTUS Database
Lens culinarisKNApSAcK Database
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Liriodendron tulipiferaKNApSAcK Database
Litchi chinensisFooDB
Litoria verreauxiiLOTUS Database
Lonicera bournei Hemsl.LOTUS Database
Lotononis angolensisKNApSAcK Database
Lotononis bainesiiKNApSAcK Database
Lotus burttiiLOTUS Database
Lotus corniculatusLOTUS Database
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Macroptilium atropurpureumKNApSAcK Database
Macroptilium bracteatumKNApSAcK Database
Macroptilium lathyroidesKNApSAcK Database
Macrotyloma axillareKNApSAcK Database
Macrotyloma uniflorumKNApSAcK Database
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Marsdenia tomentosaKNApSAcK Database
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaKNApSAcK Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Murraya paniculataKNApSAcK Database
Mus musculusLOTUS Database
Musa acuminataFooDB
Musa x paradisiacaFooDB
Mycoplasma gallisepticumLOTUS Database
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaKNApSAcK Database
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengKNApSAcK Database
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisKNApSAcK Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Populus maximowicziiKNApSAcK Database
Populus nigraKNApSAcK Database
Populus tremulaLOTUS Database
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Primula verisLOTUS Database
Prunus armeniacaFooDB
Prunus aviumKNApSAcK Database
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Pueraria PhaseoloidesKNApSAcK Database
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
Quassia indicaLOTUS Database
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Rhodiola kirilowiiKNApSAcK Database
Rhodiola roseaKNApSAcK Database
Rhynchosia beddomeiKNApSAcK Database
Rhynchosia hirtaKNApSAcK Database
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salacia chinensisLOTUS Database
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Sandoricum koetjapeLOTUS Database
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Sebertia acuminataKNApSAcK Database
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum L.KNApSAcK Database
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumKNApSAcK Database
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaKNApSAcK Database
Struthio camelusFooDB
Stylosanthes guianensisKNApSAcK Database
Stylosanthes humilisKNApSAcK Database
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Theobroma cacaoFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumKNApSAcK Database
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Vahlia capensisLOTUS Database
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Xylopia poilaneiKNApSAcK Database
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Phoma medicaginisKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentCyclohexanols
Alternative Parents
Substituents
  • Cyclohexanol
  • Sugar alcohol
  • Cyclitol or derivatives
  • Cyclic alcohol
  • Polyol
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point225 °CNot Available
Boiling Point339.10 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility143 mg/mL at 19 °CWishart, D. S., Tzur, D., Knox, C., Eisner, R., Guo, A. C., Young, N., ... & Querengesser, L. (2007). HMDB: the human metabolome database. Nucleic acids research, 35(suppl_1), D521-D526.
LogP1.680The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility485 g/LALOGPS
logP-2.6ALOGPS
logP-3.8ChemAxon
logS0.43ALOGPS
pKa (Strongest Acidic)12.29ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area121.38 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.78 m³·mol⁻¹ChemAxon
Polarizability16.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000211
DrugBank IDDB13178
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010547
KNApSAcK IDC00001164
Chemspider ID10239179
KEGG Compound IDC00137
BioCyc IDMYO-INOSITOL
BiGG ID33990
Wikipedia LinkInositol
METLIN ID5221
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID17268
Good Scents IDrw1251521
References
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Shetty HU, Holloway HW, Rapoport SI: Capillary gas chromatography combined with ion trap detection for quantitative profiling of polyols in cerebrospinal fluid and plasma. Anal Biochem. 1995 Jan 1;224(1):279-85. [PubMed:7710082 ]
  3. Kusmierz J, DeGeorge JJ, Sweeney D, May C, Rapoport SI: Quantitative analysis of polyols in human plasma and cerebrospinal fluid. J Chromatogr. 1989 Dec 29;497:39-48. [PubMed:2625478 ]
  4. Gryz EA, Galicka-Latala D, Szczudlik A, Sieradzki J: [Etiopathogenesis of diabetic neuropathy]. Przegl Lek. 2000;57(12):727-31. [PubMed:11398597 ]
  5. Kim MO, Im JH, Choi CG, Lee MC: Proton MR spectroscopic findings in paroxysmal kinesigenic dyskinesia. Mov Disord. 1998 May;13(3):570-5. [PubMed:9613757 ]
  6. Wuarin-Bierman L, Zahnd GR: Current aspects of research on the pathogenesis of diabetic neuropathy. Diabete Metab. 1986 Dec;12(6):319-24. [PubMed:3028879 ]
  7. Reznek RH, Salway JG, Thomas PK: Plasma-myoinositol concentrations in uraemic neuropathy. Lancet. 1977 Mar 26;1(8013):675-6. [PubMed:66475 ]
  8. Scully SE, Stebner FC, Yoest SM: Magnetic resonance spectroscopic findings in neuro-Behcet disease. Neurologist. 2004 Nov;10(6):323-6. [PubMed:15518598 ]
  9. Cordoba J, Hinojosa C, Sampedro F, Alonso J, Rovira A, Quiroga S, Esteban R, Guardia J: Usefulness of magnetic resonance spectroscopy for diagnosis of hepatic encephalopathy in a patient with relapsing confusional syndrome. Dig Dis Sci. 2001 Nov;46(11):2451-5. [PubMed:11713951 ]
  10. Chang L, Ernst T, Leonido-Yee M, Witt M, Speck O, Walot I, Miller EN: Highly active antiretroviral therapy reverses brain metabolite abnormalities in mild HIV dementia. Neurology. 1999 Sep 11;53(4):782-9. [PubMed:10489041 ]
  11. Ashwal S, Holshouser B, Tong K, Serna T, Osterdock R, Gross M, Kido D: Proton spectroscopy detected myoinositol in children with traumatic brain injury. Pediatr Res. 2004 Oct;56(4):630-8. Epub 2004 Aug 4. [PubMed:15295080 ]
  12. Servo C, Pitkanen E: Variation in polyol levels in cerebrospinal fluid and serum in diabetic patients. Diabetologia. 1975 Dec;11(6):575-80. [PubMed:1205026 ]
  13. Utriainen M, Komu M, Vuorinen V, Lehikoinen P, Sonninen P, Kurki T, Utriainen T, Roivainen A, Kalimo H, Minn H: Evaluation of brain tumor metabolism with [11C]choline PET and 1H-MRS. J Neurooncol. 2003 May;62(3):329-38. [PubMed:12777086 ]
  14. Grzelec H: [Pathogenesis and treatment of diabetic neuropathy]. Neurol Neurochir Pol. 1991 Jul-Aug;25(4):477-84. [PubMed:1666426 ]
  15. Ernst T, Itti E, Itti L, Chang L: Changes in cerebral metabolism are detected prior to perfusion changes in early HIV-CMC: A coregistered (1)H MRS and SPECT study. J Magn Reson Imaging. 2000 Dec;12(6):859-65. [PubMed:11105023 ]
  16. Hallman M, Saugstad OD, Porreco RP, Epstein BL, Gluck L: Role of myoinositol in regulation of surfactant phospholipids in the newborn. Early Hum Dev. 1985 Jan;10(3-4):245-54. [PubMed:3838720 ]
  17. Chang L, Lee PL, Yiannoutsos CT, Ernst T, Marra CM, Richards T, Kolson D, Schifitto G, Jarvik JG, Miller EN, Lenkinski R, Gonzalez G, Navia BA: A multicenter in vivo proton-MRS study of HIV-associated dementia and its relationship to age. Neuroimage. 2004 Dec;23(4):1336-47. [PubMed:15589098 ]
  18. Rysz J, Bartnicki P, Blaszczak R, Kujawski K, Cialkowska-Rysz A, Olszewski R, Markuszewski L: [Anti-inflammatory action of myoinositol in renal insufficiency]. Pol Merkur Lekarski. 2006 Feb;20(116):180-3. [PubMed:16708635 ]
  19. Lee PL, Yiannoutsos CT, Ernst T, Chang L, Marra CM, Jarvik JG, Richards TL, Kwok EW, Kolson DL, Simpson D, Tang CY, Schifitto G, Ketonen LM, Meyerhoff DJ, Lenkinski RE, Gonzalez RG, Navia BA: A multi-center 1H MRS study of the AIDS dementia complex: validation and preliminary analysis. J Magn Reson Imaging. 2003 Jun;17(6):625-33. [PubMed:12766890 ]
  20. Galasko GT, Bao Y, Broomfield SJ, Hooper NM, Turner AJ, Larner J: Circulating factors and insulin resistance. I. A novel myoinositol 1,2-cyclic phosphate phosphoglycan insulin antagonist from human plasma is elevated in noninsulin-dependent diabetes mellitus. J Clin Endocrinol Metab. 1995 Aug;80(8):2419-29. [PubMed:7629237 ]
  21. Yiannoutsos CT, Ernst T, Chang L, Lee PL, Richards T, Marra CM, Meyerhoff DJ, Jarvik JG, Kolson D, Schifitto G, Ellis RJ, Swindells S, Simpson DM, Miller EN, Gonzalez RG, Navia BA: Regional patterns of brain metabolites in AIDS dementia complex. Neuroimage. 2004 Nov;23(3):928-35. [PubMed:15528093 ]