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Showing NP-Card for Lactitol (NP0339507)

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Record Information
Version2.0
Created at2024-09-11 22:10:53 UTC
Updated at2024-09-11 22:10:53 UTC
NP-MRD IDNP0339507
Secondary Accession NumbersNone
Natural Product Identification
Common NameLactitol
DescriptionLactitol, also known as importal or oponaf, 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. Lactitol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Lactitol is found, on average, in the highest concentration within milk (cow). Lactitol has also been detected, but not quantified in, herbs and spices. Lactitol was first documented in 1987 (PMID: 2885579). This could make lactitol a potential biomarker for the consumption of these foods (PMID: 10654158) (PMID: 1596932) (PMID: 21853265) (PMID: 23165913).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339507 (Lactitol)


  Mrv1652307301920052D          

 23 23  0  0  1  0            999 V2000
    6.4003   -7.0465    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4003   -7.8831    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1113   -8.3014    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8224   -7.8831    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8224   -7.0465    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1113   -6.6283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6474   -6.6283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5753   -8.3014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6474   -8.3014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1113   -9.1379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5753   -6.6283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5335   -5.7917    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2864   -5.3734    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9975   -5.7917    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7085   -5.3734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4196   -5.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8224   -5.3734    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1113   -5.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4003   -5.3734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2864   -4.5369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9975   -6.6283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8224   -4.5369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9314   -7.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
 12 11  1  6  0  0  0
  5  6  1  0  0  0  0
 12 13  1  0  0  0  0
  6  1  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  1  7  1  1  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
  4  8  1  6  0  0  0
 17 18  1  0  0  0  0
  1  2  1  0  0  0  0
 18 19  1  0  0  0  0
  2  9  1  1  0  0  0
 13 20  1  6  0  0  0
  2  3  1  0  0  0  0
 14 21  1  6  0  0  0
  3 10  1  1  0  0  0
 17 22  1  1  0  0  0
  3  4  1  0  0  0  0
  5 11  1  1  0  0  0
  7 23  1  0  0  0  0
M  END
Download

3D MOL for NP0339507 (Lactitol)

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3D SDF for NP0339507 (Lactitol)

  Mrv1652307301920052D          

 23 23  0  0  1  0            999 V2000
    6.4003   -7.0465    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4003   -7.8831    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1113   -8.3014    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8224   -7.8831    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8224   -7.0465    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1113   -6.6283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6474   -6.6283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5753   -8.3014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6474   -8.3014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1113   -9.1379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5753   -6.6283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5335   -5.7917    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2864   -5.3734    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9975   -5.7917    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7085   -5.3734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4196   -5.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8224   -5.3734    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1113   -5.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4003   -5.3734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2864   -4.5369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9975   -6.6283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8224   -4.5369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9314   -7.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
 12 11  1  6  0  0  0
  5  6  1  0  0  0  0
 12 13  1  0  0  0  0
  6  1  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  1  7  1  1  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
  4  8  1  6  0  0  0
 17 18  1  0  0  0  0
  1  2  1  0  0  0  0
 18 19  1  0  0  0  0
  2  9  1  1  0  0  0
 13 20  1  6  0  0  0
  2  3  1  0  0  0  0
 14 21  1  6  0  0  0
  3 10  1  1  0  0  0
 17 22  1  1  0  0  0
  3  4  1  0  0  0  0
  5 11  1  1  0  0  0
  7 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339507

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H24O11/c13-1-4(16)7(18)11(5(17)2-14)23-12-10(21)9(20)8(19)6(3-15)22-12/h4-21H,1-3H2/t4-,5+,6+,7+,8-,9-,10+,11+,12-/m0/s1

> <INCHI_KEY>
VQHSOMBJVWLPSR-JVCRWLNRSA-N

> <FORMULA>
C12H24O11

> <MOLECULAR_WEIGHT>
344.3124

> <EXACT_MASS>
344.13186161

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
31.980754155713647

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5R)-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexane-1,2,3,5,6-pentol

> <JCHEM_LOGP>
-5.500854494333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.710069436426757

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.099718922094596

> <JCHEM_PKA_STRONGEST_BASIC>
-2.974505917782067

> <JCHEM_POLAR_SURFACE_AREA>
200.52999999999997

> <JCHEM_REFRACTIVITY>
70.8169

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
lactitol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0339507 (Lactitol)
Download
PDB for NP0339507 (Lactitol)
HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0      11.947 -13.153   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.947 -14.715   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.274 -15.496   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.602 -14.715   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.602 -13.153   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      13.274 -12.373   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.542 -12.373   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      16.007 -15.496   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      10.542 -15.496   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      13.274 -17.057   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      16.007 -12.373   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      15.929 -10.811   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.335 -10.030   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.662 -10.811   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.989 -10.030   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      21.317 -10.811   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      14.602 -10.030   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.274 -10.811   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.947 -10.030   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      17.335  -8.469   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      18.662 -12.373   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      14.602  -8.469   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.205 -13.174   0.000  0.00  0.00           O+0
CONECT    1    6    7    2                                                  
CONECT    2    1    9    3                                                  
CONECT    3    2   10    4                                                  
CONECT    4    5    8    3                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    1                                                       
CONECT    7    1   23                                                       
CONECT    8    4                                                            
CONECT    9    2                                                            
CONECT   10    3                                                            
CONECT   11   12    5                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   12   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22   17                                                            
CONECT   23    7                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

Download
3D PDB for NP0339507 (Lactitol)
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SMILES for NP0339507 (Lactitol)
OC[C@H](O)[C@@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)CO
Download
INCHI for NP0339507 (Lactitol)
InChI=1S/C12H24O11/c13-1-4(16)7(18)11(5(17)2-14)23-12-10(21)9(20)8(19)6(3-15)22-12/h4-21H,1-3H2/t4-,5+,6+,7+,8-,9-,10+,11+,12-/m0/s1
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View in JSmol
Synonyms
ValueSource
D-LactitolChEBI
ImportalChEBI
LactitolumChEBI
Neda lactiv importalHMDB
4-O-beta-D-Galactopyranosyl-D-glucitolHMDB
EmportalHMDB
OponafHMDB
4-O-Β-D-galactopyranosyl-D-glucitolHMDB
LactitolHMDB
Chemical FormulaC12H24O11
Average Mass344.3124 Da
Monoisotopic Mass344.13186 Da
IUPAC Name(2S,3R,4R,5R)-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexane-1,2,3,5,6-pentol
Traditional Namelactitol
CAS Registry NumberNot Available
SMILES
OC[C@H](O)[C@@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)CO
InChI Identifier
InChI=1S/C12H24O11/c13-1-4(16)7(18)11(5(17)2-14)23-12-10(21)9(20)8(19)6(3-15)22-12/h4-21H,1-3H2/t4-,5+,6+,7+,8-,9-,10+,11+,12-/m0/s1
InChI KeyVQHSOMBJVWLPSR-JVCRWLNRSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acyl glycosides  
Direct ParentFatty acyl glycosides of mono- and disaccharides  
Alternative Parents
Substituents
  • Fatty acyl glycoside of mono- or disaccharide
    • 

  • Alkyl glycoside
    • 

  • Disaccharide
    • 

  • Glycosyl compound
    • 

  • O-glycosyl compound
    • 

  • Fatty alcohol
    • 

  • Sugar alcohol
    • 

  • Oxane
    • 

  • Secondary alcohol
    • 

  • Acetal
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Polyol
    • 

  • Organooxygen compound
    • 

  • Primary alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-5.5ChemAxon
pKa (Strongest Acidic)12.1ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area200.53 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity70.82 m³·mol⁻¹ChemAxon
Polarizability31.98 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040937  
DrugBank IDDB12942  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020779  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD0-2460  
BiGG IDNot Available
Wikipedia LinkLactitol  
METLIN IDNot Available
PubChem Compound157355  
PDB IDNot Available
ChEBI ID75323  
Good Scents IDNot Available
References
General References
  1. Soontornchai S, Sirichakwal P, Puwastien P, Tontisirin K, Kruger D, Grossklaus R: Lactitol tolerance in healthy Thai adults. Eur J Nutr. 1999 Oct;38(5):218-26. doi: 10.1007/s003940050064. [PubMed:10654158  ] 
  2. Kivikoski J, Pitkanen I, Valkonen J, Heikkila H: Crystal structure of lactitol (4-O-beta-D-galactopyranosyl-D-glucitol). Carbohydr Res. 1992 Jan;223:45-51. doi: 10.1016/0008-6215(92)80004-k. [PubMed:1596932  ] 
  3. Bjorklund M, Ouwehand AC, Forssten SD, Nikkila J, Tiihonen K, Rautonen N, Lahtinen SJ: Gut microbiota of healthy elderly NSAID users is selectively modified with the administration of Lactobacillus acidophilus NCFM and lactitol. Age (Dordr). 2012 Aug;34(4):987-99. doi: 10.1007/s11357-011-9294-5. Epub 2011 Aug  19. [PubMed:21853265  ] 
  4. Chen C, Yu X, Lu H, Xiao D, Mao W, Li L: Antioxidant protective effects of lactitol against endotoxemia in patients with chronic viral hepatitis. Mol Med Rep. 2013 Feb;7(2):401-5. doi: 10.3892/mmr.2012.1188. Epub 2012 Nov 16. [PubMed:23165913  ] 
  5. Authors unspecified: Lactitol. Lancet. 1987 Jul 11;2(8550):81-2. [PubMed:2885579  ]