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Showing NP-Card for (1r,2r,4s,5s)-6-methoxycyclohexane-1,2,3,4,5-pentol (NP0150508)

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Record Information
Version2.0
Created at2022-09-02 06:38:08 UTC
Updated at2022-09-02 06:38:09 UTC
NP-MRD IDNP0150508
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,2r,4s,5s)-6-methoxycyclohexane-1,2,3,4,5-pentol
Description1-O-methyl-muco-inositol belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. (1r,2r,4s,5s)-6-methoxycyclohexane-1,2,3,4,5-pentol is found in Croton cortesianus. (1r,2r,4s,5s)-6-methoxycyclohexane-1,2,3,4,5-pentol was first documented in 1989 (PMID: 24272011). Based on a literature review very few articles have been published on 1-O-methyl-muco-inositol (PMID: 33874155).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0150508 ((1r,2r,4s,5s)-6-methoxycyclohexane-1,2,3,4,5-pentol)


  Mrv1652309022208382D          

 13 13  0  0  1  0            999 V2000
    0.0000    2.4750    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   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
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  1  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
    0.0000    0.8250    0.0000 C   0  0  1  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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  1  0  0  0
M  END
Download

3D MOL for NP0150508 ((1r,2r,4s,5s)-6-methoxycyclohexane-1,2,3,4,5-pentol)

     RDKit          3D

 27 27  0  0  0  0  0  0  0  0999 V2000
    3.2390    0.4251    0.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0257    0.3499    0.9877 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9579    0.1250    0.1162 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0663    1.3176    0.1901 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4196    2.2223   -0.8199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3856    1.0410    0.0658 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0785    2.0979   -0.4954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6547   -0.2290   -0.7218 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0418   -0.3749   -0.7928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0900   -1.3446    0.1354 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3489   -2.5970   -0.4518 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466   -1.1789    0.4449 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0525   -2.1869   -0.2548 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792    1.2458   -0.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0220    0.5375    1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4206   -0.5366   -0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4050    0.0668   -0.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2225    1.8777    1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7024    3.0882   -0.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7962    0.8681    1.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9464    2.2188   -0.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2286   -0.2135   -1.7256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3842   -0.7564    0.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7025   -1.3281    1.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0046   -3.2621    0.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5051   -1.4328    1.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977   -2.0410   -1.2367 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
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  6
  4 18  1  1
  5 19  1  0
  6 20  1  1
  7 21  1  0
  8 22  1  6
  9 23  1  0
 10 24  1  1
 11 25  1  0
 12 26  1  1
 13 27  1  0
M  END
Download

3D SDF for NP0150508 ((1r,2r,4s,5s)-6-methoxycyclohexane-1,2,3,4,5-pentol)


  Mrv1652309022208382D          

 13 13  0  0  1  0            999 V2000
    0.0000    2.4750    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   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
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  1  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
    0.0000    0.8250    0.0000 C   0  0  1  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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0150508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1[C@@H](O)[C@@H](O)C(O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2?,3-,4+,5-,6+,7?

> <INCHI_KEY>
DSCFFEYYQKSRSV-QQTVYWKESA-N

> <FORMULA>
C7H14O6

> <MOLECULAR_WEIGHT>
194.183

> <EXACT_MASS>
194.079038171

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.132588997416907

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,5S)-6-methoxycyclohexane-1,2,3,4,5-pentol

> <ALOGPS_LOGP>
-2.67

> <JCHEM_LOGP>
-3.138883148333333

> <ALOGPS_LOGS>
0.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.999964550804691

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.360891065931447

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6457717234067664

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
40.526199999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.44e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,5S)-6-methoxycyclohexane-1,2,3,4,5-pentol

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0150508 ((1r,2r,4s,5s)-6-methoxycyclohexane-1,2,3,4,5-pentol)

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PDB for NP0150508 ((1r,2r,4s,5s)-6-methoxycyclohexane-1,2,3,4,5-pentol)
HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   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  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    3   13                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0150508 ((1r,2r,4s,5s)-6-methoxycyclohexane-1,2,3,4,5-pentol)
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SMILES for NP0150508 ((1r,2r,4s,5s)-6-methoxycyclohexane-1,2,3,4,5-pentol)
COC1[C@@H](O)[C@@H](O)C(O)[C@@H](O)[C@H]1O
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INCHI for NP0150508 ((1r,2r,4s,5s)-6-methoxycyclohexane-1,2,3,4,5-pentol)
InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2?,3-,4+,5-,6+,7?
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View in JSmol
SynonymsNot Available
Chemical FormulaC7H14O6
Average Mass194.1830 Da
Monoisotopic Mass194.07904 Da
IUPAC Name(1R,2R,4S,5S)-6-methoxycyclohexane-1,2,3,4,5-pentol
Traditional Name(1R,2R,4S,5S)-6-methoxycyclohexane-1,2,3,4,5-pentol
CAS Registry NumberNot Available
SMILES
COC1[C@@H](O)[C@@H](O)C(O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2?,3-,4+,5-,6+,7?
InChI KeyDSCFFEYYQKSRSV-QQTVYWKESA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Croton cortesianusLOTUS 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
    • 

  • Cyclitol or derivatives
    • 

  • Cyclic alcohol
    • 

  • Polyol
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
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-2.7ALOGPS
logP-3.1ChemAxon
logS0.45ALOGPS
pKa (Strongest Acidic)12.36ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.53 m³·mol⁻¹ChemAxon
Polarizability18.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00040932  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6551016  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Richter A, Popp M: The physiological importance of accumulation of cyclitols in Viscum album L. New Phytol. 1992 Jul;121(3):431-438. doi: 10.1111/j.1469-8137.1992.tb02943.x. [PubMed:33874155  ] 
  2. Neilson MJ, Richards GN: Chemical composition of degrading mangrove leaf litter and changes produced after consumption by mangrove crabNeosarmatium smithi (Crustacea: Decapoda: Sesarmidae). J Chem Ecol. 1989 Apr;15(4):1267-83. doi: 10.1007/BF01014829. [PubMed:24272011  ] 
  3. LOTUS database [Link]