Np mrd loader

Showing NP-Card for (-)-trans-p-menthan-cis-ol (NP0186357)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-09-04 02:11:06 UTC
Updated at2022-09-04 02:11:06 UTC
NP-MRD IDNP0186357
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-trans-p-menthan-cis-ol
DescriptionP-Menthan-1-ol, also known as dihydroterpineol, 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. P-Menthan-1-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, p-Menthan-1-ol has been detected, but not quantified in, herbs and spices. (-)-trans-p-menthan-cis-ol is found in Clinopodium serpyllifolium. This could make p-menthan-1-ol a potential biomarker for the consumption of these foods.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0186357 ((-)-trans-p-menthan-cis-ol)


  Mrv0541 05061309312D          

 11 11  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    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
    0.0000    0.0000    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    0.8250    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  3  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
M  END
Download

3D MOL for NP0186357 ((-)-trans-p-menthan-cis-ol)

     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.6384   -1.0993   -1.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1334    0.0866   -0.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473    0.1443    0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6376    0.1022   -0.2437 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0565   -1.1268    0.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291   -1.1319   -0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0026    0.2283    0.2053 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4697    0.1632    0.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9572    0.9650   -0.9994 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1790    1.0190    1.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1561    1.2975    0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367   -2.0627   -0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2181   -1.0096   -2.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7477   -0.9327   -1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4227    0.9971   -0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8920    1.1553    1.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4738   -0.6204    1.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9199   -0.1416    0.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312    0.1908   -1.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1682   -1.1468    1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5101   -2.0746    0.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4299   -1.3644   -1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9733   -1.9438    0.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6174   -0.7862    1.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1246    0.2399   -0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6289    1.0092    1.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639    1.5286   -1.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6949    2.0037    1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0953    0.5333    2.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9100    1.6322    1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0339    2.1445   -0.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4 11  1  0
 11 10  1  0
 10  7  1  0
  7  8  1  0
  7  9  1  6
  7  6  1  0
  6  5  1  0
  5  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  6
 11 30  1  0
 11 31  1  0
 10 28  1  0
 10 29  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  6 22  1  0
  6 23  1  0
  5 20  1  0
  5 21  1  0
M  END
Download

3D SDF for NP0186357 ((-)-trans-p-menthan-cis-ol)


  Mrv0541 05061309312D          

 11 11  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    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
    0.0000    0.0000    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    0.8250    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  3  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0186357

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1CCC(C)(O)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C10H20O/c1-8(2)9-4-6-10(3,11)7-5-9/h8-9,11H,4-7H2,1-3H3

> <INCHI_KEY>
CMLYGGFIXXLYQT-UHFFFAOYSA-N

> <FORMULA>
C10H20O

> <MOLECULAR_WEIGHT>
156.2652

> <EXACT_MASS>
156.151415262

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
19.57561304447013

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-methyl-4-(propan-2-yl)cyclohexan-1-ol

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
2.5798769889999997

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.926903249683292

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0811725185885273

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
47.6119

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-isopropyl-1-methylcyclohexan-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0186357 ((-)-trans-p-menthan-cis-ol)

Download
PDB for NP0186357 ((-)-trans-p-menthan-cis-ol)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.324   3.490   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3   10                                                            
CONECT    4    6    9                                                       
CONECT    5    7    9                                                       
CONECT    6    4   10                                                       
CONECT    7    5   10                                                       
CONECT    8    1    2    9                                                  
CONECT    9    4    5    8                                                  
CONECT   10    3    6    7   11                                             
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

Download
3D PDB for NP0186357 ((-)-trans-p-menthan-cis-ol)
Download
SMILES for NP0186357 ((-)-trans-p-menthan-cis-ol)
CC(C)C1CCC(C)(O)CC1
Download
INCHI for NP0186357 ((-)-trans-p-menthan-cis-ol)
InChI=1S/C10H20O/c1-8(2)9-4-6-10(3,11)7-5-9/h8-9,11H,4-7H2,1-3H3
Download
View in JSmol
Synonyms
ValueSource
1-Methyl-4-(1-methylethyl)-cis-cyclohexanolHMDB
1-Methyl-4-(1-methylethyl)-cyclohexanolHMDB
1-Methyl-4-(1-methylethyl)-trans-cyclohexanolHMDB
1-Methyl-4-(1-methylethyl)cyclohexanolHMDB
1-Methyl-4-(1-methylethyl)cyclohexanol, 9ciHMDB
1-Methyl-4-(isopropyl)cyclohexan-1-olHMDB
4-Isopropyl-1-methylcyclohexanolHMDB
Cyclohexane, 1-methyl-4-(1-methylethyl)-, hydroxy deriv.HMDB
Dihydro-b-terpineolHMDB
DihydroterpineolHMDB
p-Mentan-1-olHMDB
trans-p-Menthan-1-olHMDB
Chemical FormulaC10H20O
Average Mass156.2652 Da
Monoisotopic Mass156.15142 Da
IUPAC Name1-methyl-4-(propan-2-yl)cyclohexan-1-ol
Traditional Name4-isopropyl-1-methylcyclohexan-1-ol
CAS Registry NumberNot Available
SMILES
CC(C)C1CCC(C)(O)CC1
InChI Identifier
InChI=1S/C10H20O/c1-8(2)9-4-6-10(3,11)7-5-9/h8-9,11H,4-7H2,1-3H3
InChI KeyCMLYGGFIXXLYQT-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Clinopodium serpyllifoliumLOTUS 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
    • 

  • Cyclohexanol
    • 

  • Tertiary alcohol
    • 

  • Cyclic 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
logP3.09ALOGPS
logP2.58ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)18.93ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.61 m³·mol⁻¹ChemAxon
Polarizability19.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0037020  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB016000  
KNApSAcK IDNot Available
Chemspider ID80716  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound89437  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]