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Showing NP-Card for cis-1,2-cyclohexanediol (NP0002752)

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Record Information
Version2.0
Created at2020-11-23 19:39:31 UTC
Updated at2021-08-12 19:52:02 UTC
NP-MRD IDNP0002752
Secondary Accession NumbersNone
Natural Product Identification
Common Namecis-1,2-cyclohexanediol
Provided ByBMRBBMRB logo
DescriptionCis-cyclohexane-1,2-diol is also known as cis-1,2-dihydroxycyclohexane or grandidentol. Cis-cyclohexane-1,2-diol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. cis-1,2-cyclohexanediol was first documented in 1961 (PMID: 13779722). Based on a literature review a small amount of articles have been published on cis-cyclohexane-1,2-diol (PMID: 34580694).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002752 (cis-1,2-cyclohexanediol)


     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
    1.6859   -1.9461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0203   -0.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1879   -1.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5619   -0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7276    0.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5194    1.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3515    0.7932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1829   -2.0418    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4597   -0.1798    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8973   -2.5263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0193   -2.7394    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9160   -2.3465    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0588   -0.7932    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1670    0.1798    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3932    1.9461    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6046    2.5263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3120    2.7394    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2087    2.3465    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1829    2.0418    0.0000 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  2  1  0
  1  9  1  0
  2 10  1  6
  3 11  1  6
  3 12  1  0
  4 13  1  1
  4 14  1  0
  5 15  1  6
  5 16  1  0
  6 17  1  1
  6 18  1  0
  7 19  1  6
  8 20  1  0
M  END
Download

3D MOL for NP0002752 (cis-1,2-cyclohexanediol)

NP0002752
     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
   -1.4440   -0.4908    1.1867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2015   -0.1533   -0.1411 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7312    1.2730   -0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4864    1.4548    0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5650    0.4603    0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0744   -0.9475    0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1071   -1.0285   -0.7266 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5384   -2.3280   -0.8663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4098   -0.5592    1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1248   -0.2475   -0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5208    1.9523    0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5405    1.5312   -1.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1863    1.3857    1.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8886    2.4654    0.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2950    0.5029    1.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0353    0.7372   -0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8143   -1.3736    1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9265   -1.5588   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1976   -0.6059   -1.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8512   -2.4696   -1.8083 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  2  1  0
  1  9  1  0
  2 10  1  6
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  6
  8 20  1  0
M  END
Download

3D SDF for NP0002752 (cis-1,2-cyclohexanediol)


     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
    1.6859   -1.9461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0203   -0.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1879   -1.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5619   -0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7276    0.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5194    1.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3515    0.7932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1829   -2.0418    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4597   -0.1798    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8973   -2.5263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0193   -2.7394    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9160   -2.3465    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0588   -0.7932    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1670    0.1798    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3932    1.9461    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6046    2.5263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3120    2.7394    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2087    2.3465    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1829    2.0418    0.0000 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  2  1  0
  1  9  1  0
  2 10  1  6
  3 11  1  6
  3 12  1  0
  4 13  1  1
  4 14  1  0
  5 15  1  6
  5 16  1  0
  6 17  1  1
  6 18  1  0
  7 19  1  6
  8 20  1  0
M  END
> <DATABASE_ID>
NP0002752

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CCCC[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O2/c7-5-3-1-2-4-6(5)8/h5-8H,1-4H2/t5-,6+

> <INCHI_KEY>
PFURGBBHAOXLIO-OLQVQODUSA-N

> <FORMULA>
C6H12O2

> <MOLECULAR_WEIGHT>
116.16

> <EXACT_MASS>
116.083729626

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
12.712615389244677

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S)-cyclohexane-1,2-diol

> <JCHEM_LOGP>
0.20578985600000005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.347902938415569

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.909715126583048

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1440200835291483

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
30.636999999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
cis-1,2-cyclohexanediol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002752 (cis-1,2-cyclohexanediol)

NP0002752
     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
   -1.4440   -0.4908    1.1867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2015   -0.1533   -0.1411 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7312    1.2730   -0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4864    1.4548    0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5650    0.4603    0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0744   -0.9475    0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1071   -1.0285   -0.7266 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5384   -2.3280   -0.8663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4098   -0.5592    1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1248   -0.2475   -0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5208    1.9523    0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5405    1.5312   -1.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1863    1.3857    1.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8886    2.4654    0.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2950    0.5029    1.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0353    0.7372   -0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8143   -1.3736    1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9265   -1.5588   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1976   -0.6059   -1.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8512   -2.4696   -1.8083 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  2  1  0
  1  9  1  0
  2 10  1  6
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  6
  8 20  1  0
M  END
Download

PDB for NP0002752 (cis-1,2-cyclohexanediol)

HEADER    PROTEIN                                 23-NOV-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-NOV-20         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   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  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6    7                                                  
CONECT    6    4    5    8                                                  
CONECT    7    5                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for NP0002752 (cis-1,2-cyclohexanediol)

COMPND    NP0002752
HETATM    1  O1  UNL     1      -1.444  -0.491   1.187  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.201  -0.153  -0.141  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.731   1.273  -0.241  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.486   1.455   0.631  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.565   0.460   0.330  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.074  -0.947   0.203  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.107  -1.028  -0.727  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.538  -2.328  -0.866  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.410  -0.559   1.369  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.125  -0.248  -0.746  1.00  0.00           H  
HETATM   11  H3  UNL     1      -1.521   1.952   0.172  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.540   1.531  -1.297  1.00  0.00           H  
HETATM   13  H5  UNL     1       0.186   1.386   1.685  1.00  0.00           H  
HETATM   14  H6  UNL     1       0.889   2.465   0.414  1.00  0.00           H  
HETATM   15  H7  UNL     1       2.295   0.503   1.176  1.00  0.00           H  
HETATM   16  H8  UNL     1       2.035   0.737  -0.642  1.00  0.00           H  
HETATM   17  H9  UNL     1       0.814  -1.374   1.185  1.00  0.00           H  
HETATM   18  H10 UNL     1       1.927  -1.559  -0.184  1.00  0.00           H  
HETATM   19  H11 UNL     1       0.198  -0.606  -1.699  1.00  0.00           H  
HETATM   20  H12 UNL     1      -0.851  -2.470  -1.808  1.00  0.00           H  
CONECT    1    2    9
CONECT    2    3    7   10
CONECT    3    4   11   12
CONECT    4    5   13   14
CONECT    5    6   15   16
CONECT    6    7   17   18
CONECT    7    8   19
CONECT    8   20
END
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SMILES for NP0002752 (cis-1,2-cyclohexanediol)

O[C@H]1CCCC[C@H]1O
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INCHI for NP0002752 (cis-1,2-cyclohexanediol)

InChI=1S/C6H12O2/c7-5-3-1-2-4-6(5)8/h5-8H,1-4H2/t5-,6+
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View in JSmol
Synonyms
ValueSource
cis-1,2-CyclohexanediolChEBI
cis-1,2-DihydroxycyclohexaneChEBI
GrandidentolChEBI
cis-Cyclohexane-1,2-diolKEGG
1,2-CyclohexanediolMeSH
1,2-Cyclohexanediol, (trans)-isomerMeSH
trans-1,2-CyclohexanediolMeSH
1,2-Cyclohexanediol, (cis)-isomerMeSH
Chemical FormulaC6H12O2
Average Mass116.1600 Da
Monoisotopic Mass116.08373 Da
IUPAC Name(1R,2S)-cyclohexane-1,2-diol
Traditional Namecis-1,2-cyclohexanediol
CAS Registry NumberNot Available
SMILES
O[C@H]1CCCC[C@H]1O
InChI Identifier
InChI=1S/C6H12O2/c7-5-3-1-2-4-6(5)8/h5-8H,1-4H2/t5-,6+
InChI KeyPFURGBBHAOXLIO-OLQVQODUSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
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
logP0.21ChemAxon
pKa (Strongest Acidic)13.91ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.64 m³·mol⁻¹ChemAxon
Polarizability12.71 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 IDNot Available
Chemspider ID83866
KEGG Compound IDC12313
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCyclohexane-1,2-diol
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID32329
Good Scents IDNot Available
References
General References
  1. VALENTA Z, KHALEQUE A, RASHID MH: Cis-Cyclohexane-1,2-diol in the beaver gland. Experientia. 1961 Mar 15;17:130. doi: 10.1007/BF02160827. [PubMed:13779722 ]
  2. Hartwig B, Suhm MA: Subtle hydrogen bonds: benchmarking with OH stretching fundamentals of vicinal diols in the gas phase. Phys Chem Chem Phys. 2021 Oct 6;23(38):21623-21640. doi: 10.1039/d1cp03367k. [PubMed:34580694 ]