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Showing NP-Card for 4-Hydroxypiperitone (NP0046823)

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Record Information
Version2.0
Created at2022-03-17 20:30:06 UTC
Updated at2022-03-17 20:30:07 UTC
NP-MRD IDNP0046823
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Hydroxypiperitone
Description4-Hydroxypiperitone 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. 4-Hydroxypiperitone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4-Hydroxypiperitone is found, on average, in the highest concentration within spearmints. This could make 4-hydroxypiperitone a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046823 (4-Hydroxypiperitone)


  Mrv1533007131513432D          

 12 12  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   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
    0.7145    1.2375    0.0000 C   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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
M  END
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3D MOL for NP0046823 (4-Hydroxypiperitone)

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3D SDF for NP0046823 (4-Hydroxypiperitone)

  Mrv1533007131513432D          

 12 12  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   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
    0.7145    1.2375    0.0000 C   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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0046823

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1CC(O)C(C)CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h6-9,11H,4-5H2,1-3H3

> <INCHI_KEY>
NCNOFEZLRJLBDH-UHFFFAOYSA-N

> <FORMULA>
C10H18O2

> <MOLECULAR_WEIGHT>
170.252

> <EXACT_MASS>
170.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
19.79583022866865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-5-methyl-2-(propan-2-yl)cyclohexan-1-one

> <ALOGPS_LOGP>
1.07

> <JCHEM_LOGP>
1.741022603666667

> <ALOGPS_LOGS>
-1.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.102397350815373

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.917187475112208

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8349511284908004

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
48.11260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-2-isopropyl-5-methylcyclohexan-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0046823 (4-Hydroxypiperitone)
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PDB for NP0046823 (4-Hydroxypiperitone)
HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   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   0.000   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  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    6                                                            
CONECT    3    7                                                            
CONECT    4    7   10                                                       
CONECT    5    8    9                                                       
CONECT    6    1    2    8                                                  
CONECT    7    3    4    9                                                  
CONECT    8    5    6   10                                                  
CONECT    9    5    7   11                                                  
CONECT   10    4    8   12                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0046823 (4-Hydroxypiperitone)
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SMILES for NP0046823 (4-Hydroxypiperitone)
CC(C)C1CC(O)C(C)CC1=O
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INCHI for NP0046823 (4-Hydroxypiperitone)
InChI=1S/C10H18O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h6-9,11H,4-5H2,1-3H3
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SynonymsNot Available
Chemical FormulaC10H18O2
Average Mass170.2520 Da
Monoisotopic Mass170.13068 Da
IUPAC Name4-hydroxy-5-methyl-2-(propan-2-yl)cyclohexan-1-one
Traditional Name4-hydroxy-2-isopropyl-5-methylcyclohexan-1-one
CAS Registry NumberNot Available
SMILES
CC(C)C1CC(O)C(C)CC1=O
InChI Identifier
InChI=1S/C10H18O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h6-9,11H,4-5H2,1-3H3
InChI KeyNCNOFEZLRJLBDH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Mentha spicataFooDB
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
    • 

  • Cyclic alcohol
    • 

  • Cyclic ketone
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP1.07ALOGPS
logP1.74ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)14.92ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.11 m³·mol⁻¹ChemAxon
Polarizability19.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0182601  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006069  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound525916  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available