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Showing NP-Card for (E)-8(9)-p-Menthen-1,2-diol (NP0046283)

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Record Information
Version2.0
Created at2022-03-17 19:55:32 UTC
Updated at2022-03-17 19:55:33 UTC
NP-MRD IDNP0046283
Secondary Accession NumbersNone
Natural Product Identification
Common Name(E)-8(9)-p-Menthen-1,2-diol
Description(E)-8(9)-p-Menthen-1,2-diol belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. (E)-8(9)-p-Menthen-1,2-diol is found in Citrus sudachi and Ferula jaeschkeana . The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes (E)-8(9)-p-Menthen-1,2-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046283 ((E)-8(9)-p-Menthen-1,2-diol)


  Mrv0541 02241212462D          

 12 12  0  0  0  0            999 V2000
   -1.7421   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0276   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0276   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4565   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4565   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0645    0.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4565   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0276   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3131   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1224    0.1422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  6  0  0  0
  4  8  1  1  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  2 11  1  0  0  0  0
  1 12  1  1  0  0  0
M  END
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3D MOL for NP0046283 ((E)-8(9)-p-Menthen-1,2-diol)

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3D SDF for NP0046283 ((E)-8(9)-p-Menthen-1,2-diol)

  Mrv0541 02241212462D          

 12 12  0  0  0  0            999 V2000
   -1.7421   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0276   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0276   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4565   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4565   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0645    0.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4565   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0276   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3131   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1224    0.1422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  6  0  0  0
  4  8  1  1  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  2 11  1  0  0  0  0
  1 12  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0046283

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@H]1CC[C@@](C)(O)C(O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O2/c1-7(2)8-4-5-10(3,12)9(11)6-8/h8-9,11-12H,1,4-6H2,2-3H3/t8-,9?,10+/m0/s1

> <INCHI_KEY>
WKZWTZTZWGWEGE-DJBFQZMMSA-N

> <FORMULA>
C10H18O2

> <MOLECULAR_WEIGHT>
170.2487

> <EXACT_MASS>
170.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
19.420138449895962

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol

> <ALOGPS_LOGP>
1.11

> <JCHEM_LOGP>
1.1573275709999997

> <ALOGPS_LOGS>
-1.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.138001665059903

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.72647686245353

> <JCHEM_PKA_STRONGEST_BASIC>
-3.207704561297077

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
48.7509

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0046283 ((E)-8(9)-p-Menthen-1,2-diol)
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PDB for NP0046283 ((E)-8(9)-p-Menthen-1,2-diol)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.252  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.918  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.918  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.252  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.585  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.585  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.854   0.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.252  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.585  -6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.918  -6.160   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.584  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.095   0.265   0.000  0.00  0.00           O+0
CONECT    1    2    6    7   12                                             
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    1                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    2                                                            
CONECT   12    1                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0046283 ((E)-8(9)-p-Menthen-1,2-diol)
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SMILES for NP0046283 ((E)-8(9)-p-Menthen-1,2-diol)
CC(=C)[C@H]1CC[C@@](C)(O)C(O)C1
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INCHI for NP0046283 ((E)-8(9)-p-Menthen-1,2-diol)
InChI=1S/C10H18O2/c1-7(2)8-4-5-10(3,12)9(11)6-8/h8-9,11-12H,1,4-6H2,2-3H3/t8-,9?,10+/m0/s1
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SynonymsNot Available
Chemical FormulaC10H18O2
Average Mass170.2487 Da
Monoisotopic Mass170.13068 Da
IUPAC Name(1R,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol
Traditional Name(1R,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol
CAS Registry NumberNot Available
SMILES
CC(=C)[C@H]1CC[C@@](C)(O)C(O)C1
InChI Identifier
InChI=1S/C10H18O2/c1-7(2)8-4-5-10(3,12)9(11)6-8/h8-9,11-12H,1,4-6H2,2-3H3/t8-,9?,10+/m0/s1
InChI KeyWKZWTZTZWGWEGE-DJBFQZMMSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Apium graveolensFooDB
Citrus sudachiPlant
Ferula jaeschkeanaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentMenthane monoterpenoids  
Alternative Parents
Substituents
  • P-menthane monoterpenoid
    • 

  • Monocyclic monoterpenoid
    • 

  • Cyclohexanol
    • 

  • Tertiary alcohol
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • 1,2-diol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • 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
logP1.11ALOGPS
logP1.16ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)13.73ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.75 m³·mol⁻¹ChemAxon
Polarizability19.42 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003886  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound130762593  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available