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Showing NP-Card for (1R,4R)-p-Mentha-2,8-dien-1-ol (NP0048142)

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Record Information
Version2.0
Created at2022-03-17 20:51:46 UTC
Updated at2022-03-17 20:51:46 UTC
NP-MRD IDNP0048142
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1R,4R)-p-Mentha-2,8-dien-1-ol
Description(1R,4R)-p-Mentha-2,8-dien-1-ol 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 (1R,4R)-p-Mentha-2,8-dien-1-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (1R,4R)-p-Mentha-2,8-dien-1-ol has been detected, but not quantified in, caraway and citrus. This could make (1R,4R)-p-mentha-2,8-dien-1-ol a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048142 ((1R,4R)-p-Mentha-2,8-dien-1-ol)


  Mrv0541 02241208242D          

 11 11  0  0  0  0            999 V2000
    0.7975    0.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7971   -0.0507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826   -0.4632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6316   -0.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6319    0.7743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826    1.1868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4488    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6319   -1.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0828   -1.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7970   -1.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6123    1.8182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  3  9  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6 11  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
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3D MOL for NP0048142 ((1R,4R)-p-Mentha-2,8-dien-1-ol)

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3D SDF for NP0048142 ((1R,4R)-p-Mentha-2,8-dien-1-ol)

  Mrv0541 02241208242D          

 11 11  0  0  0  0            999 V2000
    0.7975    0.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7971   -0.0507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826   -0.4632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6316   -0.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6319    0.7743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826    1.1868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4488    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6319   -1.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0828   -1.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7970   -1.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6123    1.8182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  3  9  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6 11  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0048142

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-8(2)9-4-6-10(3,11)7-5-9/h4,6,9,11H,1,5,7H2,2-3H3/t9-,10-/m0/s1

> <INCHI_KEY>
MKPMHJQMNACGDI-UWVGGRQHSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.2334

> <EXACT_MASS>
152.120115134

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
17.991903054739

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
2.026216981333333

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.247779344243927

> <JCHEM_PKA_STRONGEST_BASIC>
-1.378221314827706

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
48.352000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.70e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048142 ((1R,4R)-p-Mentha-2,8-dien-1-ol)
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PDB for NP0048142 ((1R,4R)-p-Mentha-2,8-dien-1-ol)
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       1.489   1.444   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.488  -0.095   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.154  -0.865   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.179  -0.096   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.180   1.445   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.154   2.215   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.838   3.395   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.180  -3.176   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.155  -2.406   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.488  -3.174   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.143   3.394   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7   11                                             
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    3    8   10                                                  
CONECT   10    9                                                            
CONECT   11    6                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0048142 ((1R,4R)-p-Mentha-2,8-dien-1-ol)
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SMILES for NP0048142 ((1R,4R)-p-Mentha-2,8-dien-1-ol)
CC(=C)[C@@H]1CC[C@@](C)(O)C=C1
Download
INCHI for NP0048142 ((1R,4R)-p-Mentha-2,8-dien-1-ol)
InChI=1S/C10H16O/c1-8(2)9-4-6-10(3,11)7-5-9/h4,6,9,11H,1,5,7H2,2-3H3/t9-,10-/m0/s1
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Synonyms
ValueSource
(+)-trans-p-Mentha-2,8-dien-1-olHMDB
Chemical FormulaC10H16O
Average Mass152.2334 Da
Monoisotopic Mass152.12012 Da
IUPAC Name(1R,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol
Traditional Name(1R,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol
CAS Registry Number52154-82-2
SMILES
CC(=C)[C@@H]1CC[C@@](C)(O)C=C1
InChI Identifier
InChI=1S/C10H16O/c1-8(2)9-4-6-10(3,11)7-5-9/h4,6,9,11H,1,5,7H2,2-3H3/t9-,10-/m0/s1
InChI KeyMKPMHJQMNACGDI-UWVGGRQHSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Carum carviFooDB
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
    • 

  • 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
logP2.58ALOGPS
logP2.03ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)18.25ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.35 m³·mol⁻¹ChemAxon
Polarizability17.99 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035077  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013701  
KNApSAcK IDC00010886  
Chemspider ID99851  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound111274  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References