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Showing NP-Card for 1-p-Menthene-8,9-diol (NP0046519)

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Record Information
Version2.0
Created at2022-03-17 20:04:35 UTC
Updated at2022-03-17 20:04:35 UTC
NP-MRD IDNP0046519
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-p-Menthene-8,9-diol
Description1-P-Menthene-8,9-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. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. 1-P-Menthene-8,9-diol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1-p-Menthene-8,9-diol has been detected, but not quantified in, caraway. 1-p-Menthene-8,9-diol is found in Spodoptera litura. This could make 1-p-menthene-8,9-diol a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046519 (1-p-Menthene-8,9-diol)

Limonene 8,9-diol
  Mrv1572001071617212D          

 12 12  0  0  0  0            999 V2000
    2.8857   -3.5714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0607   -3.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2357   -2.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2357   -0.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4107   -0.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4107   -2.1429    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
    0.9357   -3.2715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643   -2.4465    0.0000 C   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
  3 11  1  0  0  0  0
  3 12  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
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3D MOL for NP0046519 (1-p-Menthene-8,9-diol)

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3D SDF for NP0046519 (1-p-Menthene-8,9-diol)
Limonene 8,9-diol
  Mrv1572001071617212D          

 12 12  0  0  0  0            999 V2000
    2.8857   -3.5714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0607   -3.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2357   -2.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2357   -0.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4107   -0.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4107   -2.1429    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
    0.9357   -3.2715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643   -2.4465    0.0000 C   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
  3 11  1  0  0  0  0
  3 12  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046519

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CCC(CC1)C(C)(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O2/c1-8-3-5-9(6-4-8)10(2,12)7-11/h3,9,11-12H,4-7H2,1-2H3

> <INCHI_KEY>
ZJALAEQNHJQSTN-UHFFFAOYSA-N

> <FORMULA>
C10H18O2

> <MOLECULAR_WEIGHT>
170.252

> <EXACT_MASS>
170.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
20.028276555430327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-methylcyclohex-3-en-1-yl)propane-1,2-diol

> <ALOGPS_LOGP>
1.54

> <JCHEM_LOGP>
1.1273875409999996

> <ALOGPS_LOGS>
-1.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.37727116331218

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.865555775118555

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0717693617306594

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
50.005599999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-methylcyclohex-3-en-1-yl)propane-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0046519 (1-p-Menthene-8,9-diol)
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PDB for NP0046519 (1-p-Menthene-8,9-diol)
HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Limonene 8,9-diol                                 
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  O   UNK     0       5.387  -6.667   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.847  -6.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.080  -5.333   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.307  -4.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.307  -1.333   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.767  -1.333   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.767  -4.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.747  -6.107   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.413  -4.567   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11   12                                             
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    4    8                                                       
CONECT   10    7                                                            
CONECT   11    3                                                            
CONECT   12    3                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0046519 (1-p-Menthene-8,9-diol)
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SMILES for NP0046519 (1-p-Menthene-8,9-diol)
CC1=CCC(CC1)C(C)(O)CO
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INCHI for NP0046519 (1-p-Menthene-8,9-diol)
InChI=1S/C10H18O2/c1-8-3-5-9(6-4-8)10(2,12)7-11/h3,9,11-12H,4-7H2,1-2H3
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Synonyms
ValueSource
P-Menth-1-ene-8,9-diolMeSH
Para-menth-1-ene-8,9-diolMeSH
4-Menth-1-ene-8,9-diolMeSH
Chemical FormulaC10H18O2
Average Mass170.2520 Da
Monoisotopic Mass170.13068 Da
IUPAC Name2-(4-methylcyclohex-3-en-1-yl)propane-1,2-diol
Traditional Name2-(4-methylcyclohex-3-en-1-yl)propane-1,2-diol
CAS Registry NumberNot Available
SMILES
CC1=CCC(CC1)C(C)(O)CO
InChI Identifier
InChI=1S/C10H18O2/c1-8-3-5-9(6-4-8)10(2,12)7-11/h3,9,11-12H,4-7H2,1-2H3
InChI KeyZJALAEQNHJQSTN-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Carum carviFooDB
Spodoptera lituraLOTUS Database
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
    • 

  • Tertiary alcohol
    • 

  • 1,2-diol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • 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
logP1.54ALOGPS
logP1.13ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)13.87ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.01 m³·mol⁻¹ChemAxon
Polarizability20.03 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0061293  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004773  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound93024  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available