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Showing NP-Card for (1r,2r,3s,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol (NP0255216)

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Record Information
Version2.0
Created at2022-09-07 19:37:56 UTC
Updated at2022-09-07 19:37:57 UTC
NP-MRD IDNP0255216
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,2r,3s,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol
DescriptionNeo-inositol belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. Neo-Inositol is one of the stereoisomers of inositol. Neo-inositol is an extremely weak basic (essentially neutral) compound (based on its pKa). It is one of the nine isomeric forms of cyclohexanehexol; a group of small and chemically very stable polar molecules that have versatile properties. (1r,2r,3s,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol is found in Croton celtidifolius. (1r,2r,3s,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol was first documented in 2000 (PMID: 10724534). This stereoisomer is naturally occurring, but only in small amounts.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0255216 ((1r,2r,3s,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol)


  Mrv1652311071918372D          

 12 12  0  0  0  0            999 V2000
   -1.4276    0.8258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -0.8241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4262    0.8240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4272   -0.8223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012   -1.6482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7157    0.4132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7158   -0.4118    0.0000 C   0  0  1  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  1  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    0.8259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0011    1.6482    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  6  0  0  0
  7  2  1  1  0  0  0
  8  5  1  1  0  0  0
  9  4  1  1  0  0  0
 10  3  1  6  0  0  0
 11 12  1  6  0  0  0
M  END
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3D MOL for NP0255216 ((1r,2r,3s,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol)

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3D SDF for NP0255216 ((1r,2r,3s,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol)

  Mrv1652311071918372D          

 12 12  0  0  0  0            999 V2000
   -1.4276    0.8258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -0.8241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4262    0.8240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4272   -0.8223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012   -1.6482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7157    0.4132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7158   -0.4118    0.0000 C   0  0  1  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  1  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    0.8259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0011    1.6482    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  6  0  0  0
  7  2  1  1  0  0  0
  8  5  1  1  0  0  0
  9  4  1  1  0  0  0
 10  3  1  6  0  0  0
 11 12  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0255216

> <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-DCLYFUHFSA-N

> <FORMULA>
C6H12O6

> <MOLECULAR_WEIGHT>
180.156

> <EXACT_MASS>
180.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.077854222839257

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3S,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>
35.775

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.85e+02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0255216 ((1r,2r,3s,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol)
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PDB for NP0255216 ((1r,2r,3s,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol)
HEADER    PROTEIN                                 07-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-NOV-19         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  -3.077   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   1.542   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.002   3.077   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

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3D PDB for NP0255216 ((1r,2r,3s,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol)
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SMILES for NP0255216 ((1r,2r,3s,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol)
O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O
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INCHI for NP0255216 ((1r,2r,3s,4s,5s,6s)-cyclohexane-1,2,3,4,5,6-hexol)
InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4-,5-,6-
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View in JSmol
Synonyms
ValueSource
(1S,2R,3R,4S,5S,6S)-Cyclohexane-1,2,3,4,5,6-hexolChEBI
1,2,3/4,5,6-cyclohexanehexolChEBI
neo-InositolHMDB
Chemical FormulaC6H12O6
Average Mass180.1560 Da
Monoisotopic Mass180.06339 Da
IUPAC Name(1R,2R,3S,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol
Traditional Name(1R,2R,3S,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol
CAS Registry NumberNot Available
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-DCLYFUHFSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Croton celtidifoliusLOTUS 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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability16.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0240208  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10199749  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNeo-Inositol  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID25492  
Good Scents IDNot Available
References
General References
  1. Hudlicky T, Restrepo-Sanchez N, Kary PD, Jaramillo-Gomez LM: A short, stereoselective synthesis of neo-inositol. Carbohydr Res. 2000 Feb 25;324(3):200-3. doi: 10.1016/s0008-6215(99)00289-x. [PubMed:10724534  ] 
  2. LOTUS database [Link]