Showing NP-Card for Mannitol (NP0000500)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:42:35 UTC
NP-MRD IDNP0000500
Secondary Accession NumbersNone
Natural Product Identification
Common NameMannitol
DescriptionMannitol, or hexan-1,2,3,4,5,6-hexol (C6H8(OH)6), is an alcohol and a sugar (sugar alcohol), or a polyol, it is a stereoisomer of sorbitol and is similar to the C5 xylitol. The structure of mannitol is made of a straight chain of six carbon atoms, each of which is substituted with a hydroxyl group. Mannitol is one of the most abundant energy and carbon storage molecules in nature, it is produced by a wide range of organisms such as bacteria, fungi and plants (PMID: 19578847 ). In medicine, mannitol is used as a diuretic and renal diagnostic aid. Mannitol has little significant energy value as it is largely eliminated from the body before any metabolism can take place. It can be used to treat oliguria associated with kidney failure or other manifestations of inadequate renal function and has been used for determination of glomerular filtration rate. Mannitol is also commonly used as a research tool in cell biological studies, usually to control osmolarity. Mannitol has a tendency to lose a hydrogen ion in aqueous solutions, which causes the solution to become acidic. For this, it is not uncommon to add a weak base, such as sodium bicarbonate, to the solution to adjust its pH. Mannitol is a non-permeating molecule i.E., It cannot cross biological membranes. Mannitol is an osmotic diuretic agent and a weak renal vasodilator. Mannitol is found to be associated with cytochrome c oxidase deficiency and ribose-5-phosphate isomerase deficiency, which are inborn errors of metabolism. Mannitol is also a microbial metabolite found in Aspergillus, Candida, Clostridium, Gluconobacter, Lactobacillus, Lactococcus, Leuconostoc, Pseudomonas, Rhodobacteraceae, Saccharomyces, Streptococcus, Torulaspora and Zymomonas (PMID: 15240312 ; PMID: 29480337 ).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000500 (Mannitol)

  Mrv1652309272007452D          

 12 11  0  0  0  0            999 V2000
 9991.0969 9991.6652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9991.8108 9991.2533    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9992.5263 9991.6652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9993.2417 9991.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9551 9991.6652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.5263 9992.4899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.8108 9990.4280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9990.3822 9991.2533    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9989.6675 9991.6652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.9529 9991.2533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9990.3822 9990.4280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.0969 9992.4899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  1 12  1  1  0  0  0
  2  3  1  0  0  0  0
  2  7  1  1  0  0  0
  3  4  1  0  0  0  0
  3  6  1  6  0  0  0
  4  5  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  6  0  0  0
  9 10  1  0  0  0  0
M  END
Download

3D MOL for NP0000500 (Mannitol)

HMDB0000765
     RDKit          3D
Mannitol
 26 25  0  0  0  0  0  0  0  0999 V2000
    3.0120   -1.2124   -1.1462 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0508   -0.2204   -0.9990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6290   -0.1659    0.4318 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7923    0.1320    1.1837 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6354    0.8923    0.7554 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1607    2.1566    0.4027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6867    0.7804    0.0786 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4840    1.8365    0.5566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4365   -0.4826    0.2908 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7658   -1.6227   -0.1437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7039   -0.4029   -0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4609   -1.5528   -0.3648 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9679   -1.8395   -0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342   -0.4541   -1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4883    0.7361   -1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3021   -1.1525    0.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814    0.1160    2.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4892    0.9142    1.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8093    2.4183   -0.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5767    0.9543   -1.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9609    2.4946    1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7230   -0.6571    1.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8026   -1.6260   -1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3213   -0.3921   -1.6278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2424    0.5258   -0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9879   -2.1762    0.2702 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
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  1
  4 17  1  0
  5 18  1  1
  6 19  1  0
  7 20  1  6
  8 21  1  0
  9 22  1  1
 10 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
M  END
Download

3D SDF for NP0000500 (Mannitol)

  Mrv1652309272007452D          

 12 11  0  0  0  0            999 V2000
 9991.0969 9991.6652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9991.8108 9991.2533    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9992.5263 9991.6652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9993.2417 9991.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9551 9991.6652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.5263 9992.4899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.8108 9990.4280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9990.3822 9991.2533    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9989.6675 9991.6652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.9529 9991.2533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9990.3822 9990.4280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.0969 9992.4899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  1 12  1  1  0  0  0
  2  3  1  0  0  0  0
  2  7  1  1  0  0  0
  3  4  1  0  0  0  0
  3  6  1  6  0  0  0
  4  5  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  6  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000500

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4-,5-,6-/m1/s1

> <INCHI_KEY>
FBPFZTCFMRRESA-KVTDHHQDSA-N

> <FORMULA>
C6H14O6

> <MOLECULAR_WEIGHT>
182.1718

> <EXACT_MASS>
182.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.040202393955006

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol

> <ALOGPS_LOGP>
-2.68

> <JCHEM_LOGP>
-3.7300188486666666

> <ALOGPS_LOGS>
0.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.37874915684328

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.585200956788803

> <JCHEM_PKA_STRONGEST_BASIC>
-2.974211614825128

> <JCHEM_POLAR_SURFACE_AREA>
121.38000000000001

> <JCHEM_REFRACTIVITY>
38.40359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.29e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mannitol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000500 (Mannitol)

HMDB0000765
     RDKit          3D
Mannitol
 26 25  0  0  0  0  0  0  0  0999 V2000
    3.0120   -1.2124   -1.1462 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0508   -0.2204   -0.9990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6290   -0.1659    0.4318 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7923    0.1320    1.1837 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6354    0.8923    0.7554 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1607    2.1566    0.4027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6867    0.7804    0.0786 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4840    1.8365    0.5566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4365   -0.4826    0.2908 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7658   -1.6227   -0.1437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7039   -0.4029   -0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4609   -1.5528   -0.3648 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9679   -1.8395   -0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342   -0.4541   -1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4883    0.7361   -1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3021   -1.1525    0.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814    0.1160    2.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4892    0.9142    1.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8093    2.4183   -0.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5767    0.9543   -1.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9609    2.4946    1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7230   -0.6571    1.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8026   -1.6260   -1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3213   -0.3921   -1.6278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2424    0.5258   -0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9879   -2.1762    0.2702 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
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  1
  4 17  1  0
  5 18  1  1
  6 19  1  0
  7 20  1  6
  8 21  1  0
  9 22  1  1
 10 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
M  END
Download

PDB for NP0000500 (Mannitol)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8650.0488651.108   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8651.3808650.339   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8652.7168651.108   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8654.0518650.339   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8655.3838651.108   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8652.7168652.648   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8651.3808648.799   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8648.7148650.339   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8647.3798651.108   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8646.0458650.339   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8648.7148648.799   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8650.0488652.648   0.000  0.00  0.00           O+0
CONECT    1    2    8   12                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3                                                            
CONECT    7    2                                                            
CONECT    8    1    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8                                                            
CONECT   12    1                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for NP0000500 (Mannitol)

COMPND    HMDB0000765
HETATM    1  O1  UNL     1       3.012  -1.212  -1.146  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.051  -0.220  -0.999  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.629  -0.166   0.432  1.00  0.00           C  
HETATM    4  O2  UNL     1       2.792   0.132   1.184  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.635   0.892   0.755  1.00  0.00           C  
HETATM    6  O3  UNL     1       1.161   2.157   0.403  1.00  0.00           O  
HETATM    7  C4  UNL     1      -0.687   0.780   0.079  1.00  0.00           C  
HETATM    8  O4  UNL     1      -1.484   1.836   0.557  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.436  -0.483   0.291  1.00  0.00           C  
HETATM   10  O5  UNL     1      -0.766  -1.623  -0.144  1.00  0.00           O  
HETATM   11  C6  UNL     1      -2.704  -0.403  -0.567  1.00  0.00           C  
HETATM   12  O6  UNL     1      -3.461  -1.553  -0.365  1.00  0.00           O  
HETATM   13  H1  UNL     1       2.968  -1.839  -0.357  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.234  -0.454  -1.701  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.488   0.736  -1.309  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.302  -1.152   0.808  1.00  0.00           H  
HETATM   17  H5  UNL     1       2.581   0.116   2.146  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.489   0.914   1.848  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.809   2.418  -0.479  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.577   0.954  -1.007  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.961   2.495   1.073  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.723  -0.657   1.349  1.00  0.00           H  
HETATM   23  H11 UNL     1      -0.803  -1.626  -1.128  1.00  0.00           H  
HETATM   24  H12 UNL     1      -2.321  -0.392  -1.628  1.00  0.00           H  
HETATM   25  H13 UNL     1      -3.242   0.526  -0.364  1.00  0.00           H  
HETATM   26  H14 UNL     1      -2.988  -2.176   0.270  1.00  0.00           H  
CONECT    1    2   13
CONECT    2    3   14   15
CONECT    3    4    5   16
CONECT    4   17
CONECT    5    6    7   18
CONECT    6   19
CONECT    7    8    9   20
CONECT    8   21
CONECT    9   10   11   22
CONECT   10   23
CONECT   11   12   24   25
CONECT   12   26
END
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SMILES for NP0000500 (Mannitol)

OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
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INCHI for NP0000500 (Mannitol)

InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4-,5-,6-/m1/s1
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View in JSmol
Synonyms
Chemical FormulaC6H14O6
Average Mass182.1718 Da
Monoisotopic Mass182.07904 Da
IUPAC Name(2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol
Traditional Namemannitol
CAS Registry Number69-65-8
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4-,5-,6-/m1/s1
InChI KeyFBPFZTCFMRRESA-KVTDHHQDSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
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
Not Available
Species
Species of Origin
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point166 °CNot Available
Boiling Point290.00 to 295.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility216 mg/mL at 25 °CYalkowsky, S. H., & Dannenfelser, R. M. (1992). Aquasol database of aqueous solubility. College of Pharmacy, University of Arizona, Tucson, AZ, 189.
LogP-3.10Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility229 g/LALOGPS
logP-2.7ALOGPS
logP-3.7ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)12.59ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area121.38 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.4 m³·mol⁻¹ChemAxon
Polarizability17.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000765
DrugBank IDDB00742
Phenol Explorer Compound IDNot Available
FoodDB IDFDB112364
KNApSAcK IDC00001165
Chemspider ID6015
KEGG Compound IDC00392
BioCyc IDMANNITOL
BiGG IDNot Available
Wikipedia LinkMannitol
METLIN ID142
PubChem Compound6251
PDB IDNot Available
ChEBI ID16899
Good Scents IDrw1030941
References
General References