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Showing NP-Card for 2-[(2r,5s)-5-methyloxolan-2-yl]propan-2-ol (NP0313732)

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Record Information
Version2.0
Created at2022-09-11 11:27:48 UTC
Updated at2022-09-11 11:27:48 UTC
NP-MRD IDNP0313732
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-[(2r,5s)-5-methyloxolan-2-yl]propan-2-ol
DescriptionPityol belongs to the class of organic compounds known as oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms. 2-[(2r,5s)-5-methyloxolan-2-yl]propan-2-ol is found in Pityophthorus pityographus. 2-[(2r,5s)-5-methyloxolan-2-yl]propan-2-ol was first documented in 2003 (PMID: 12737268). Based on a literature review a small amount of articles have been published on Pityol (PMID: 23885894) (PMID: 22764125) (PMID: 17598543).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0313732 (2-[(2r,5s)-5-methyloxolan-2-yl]propan-2-ol)


  Mrv1652309112213272D          

 10 10  0  0  1  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8146   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9971   -0.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3378   -1.3076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  6  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  5 10  1  0  0  0  0
  2 10  1  0  0  0  0
M  END
Download

3D MOL for NP0313732 (2-[(2r,5s)-5-methyloxolan-2-yl]propan-2-ol)

     RDKit          3D

 26 26  0  0  0  0  0  0  0  0999 V2000
    2.8475    1.0167    0.9847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7866    0.7159   -0.0473 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9056   -0.7530   -0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4256   -1.0485   -0.6560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1483   -0.2526    0.5244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6228   -0.1934    0.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3420    0.6609    1.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9910    0.2277   -1.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1161   -1.5092    0.4979 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5100    0.9364    0.4057 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8309    1.0390    0.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7093    1.9629    1.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9320    0.1334    1.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9892    1.2807   -0.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1736   -1.3302    0.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5242   -0.9445   -1.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1694   -0.5466   -1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1901   -2.1042   -0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1412   -0.7968    1.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4443    0.4482    1.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2444    1.7508    1.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1082    0.3820    2.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8733   -0.6857   -1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0922    0.4282   -1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3975    1.0791   -1.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550   -1.8974    1.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5 10  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  6
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  1
  7 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
M  END
Download

3D SDF for NP0313732 (2-[(2r,5s)-5-methyloxolan-2-yl]propan-2-ol)


  Mrv1652309112213272D          

 10 10  0  0  1  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8146   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9971   -0.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3378   -1.3076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  6  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  5 10  1  0  0  0  0
  2 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0313732

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@@H](O1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C8H16O2/c1-6-4-5-7(10-6)8(2,3)9/h6-7,9H,4-5H2,1-3H3/t6-,7+/m0/s1

> <INCHI_KEY>
GDFJZYRQAYBNLM-NKWVEPMBSA-N

> <FORMULA>
C8H16O2

> <MOLECULAR_WEIGHT>
144.214

> <EXACT_MASS>
144.115029755

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
16.792207036164104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2R,5S)-5-methyloxolan-2-yl]propan-2-ol

> <JCHEM_LOGP>
1.013738677333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.326074576780918

> <JCHEM_PKA_STRONGEST_BASIC>
-3.093574980116026

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
39.9918

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2R,5S)-5-methyloxolan-2-yl]propan-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0313732 (2-[(2r,5s)-5-methyloxolan-2-yl]propan-2-ol)

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PDB for NP0313732 (2-[(2r,5s)-5-methyloxolan-2-yl]propan-2-ol)
HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.521  -2.782   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.861  -0.631   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.631  -2.441   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    5    2                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0313732 (2-[(2r,5s)-5-methyloxolan-2-yl]propan-2-ol)
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SMILES for NP0313732 (2-[(2r,5s)-5-methyloxolan-2-yl]propan-2-ol)
C[C@H]1CC[C@@H](O1)C(C)(C)O
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INCHI for NP0313732 (2-[(2r,5s)-5-methyloxolan-2-yl]propan-2-ol)
InChI=1S/C8H16O2/c1-6-4-5-7(10-6)8(2,3)9/h6-7,9H,4-5H2,1-3H3/t6-,7+/m0/s1
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View in JSmol
Synonyms
ValueSource
2-(1-Hydroxy-1-methylethyl)-5-methyltetrahydrofuranMeSH
Chemical FormulaC8H16O2
Average Mass144.2140 Da
Monoisotopic Mass144.11503 Da
IUPAC Name2-[(2R,5S)-5-methyloxolan-2-yl]propan-2-ol
Traditional Name2-[(2R,5S)-5-methyloxolan-2-yl]propan-2-ol
CAS Registry NumberNot Available
SMILES
C[C@H]1CC[C@@H](O1)C(C)(C)O
InChI Identifier
InChI=1S/C8H16O2/c1-6-4-5-7(10-6)8(2,3)9/h6-7,9H,4-5H2,1-3H3/t6-,7+/m0/s1
InChI KeyGDFJZYRQAYBNLM-NKWVEPMBSA-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
Pityophthorus pityographusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassOxolanes  
Sub ClassNot Available
Direct ParentOxolanes  
Alternative Parents
Substituents
  • Tertiary alcohol
    • 

  • Oxolane
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP1.01ChemAxon
pKa (Strongest Acidic)14.33ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.99 m³·mol⁻¹ChemAxon
Polarizability16.79 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9084948  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10909691  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Lopez S, Iturrondobeitia JC, Goldarazena A: Field response of the twig beetle, Pityophthorus pubescens, to the aggregation pheromone, (E)-(+)-pityol, is not inhibited by (E)-(-)-pityol, and evidence of monogyny. J Insect Sci. 2013;13:15. doi: 10.1673/031.013.1501. [PubMed:23885894  ] 
  2. Lopez S, Quero C, Iturrondobeitia JC, Guerrero A, Goldarazena A: Electrophysiological and behavioural responses of Pityophthorus pubescens (Coleoptera: Scolytinae) to (E,E)-alpha-farnesene, (R)-(+)-limonene and (S)-(-)-verbenone in Pinus radiata (Pinaceae) stands in northern Spain. Pest Manag Sci. 2013 Jan;69(1):40-7. doi: 10.1002/ps.3359. Epub 2012 Jul 5. [PubMed:22764125  ] 
  3. Miller DR: Limonene: attractant kairomone for white pine cone beetles (Coleoptera: Scolytidae) in an eastern white pine seed orchard in western North Carolina. J Econ Entomol. 2007 Jun;100(3):815-22. doi:  10.1603/0022-0493(2007)100[815:lakfwp]2.0.co;2. [PubMed:17598543  ] 
  4. Miller DR, Crowe CM, Asaro C, Debarr GL: Dose and enantiospecific responses of white pine cone beetles, Conophthorus coniperda, to alpha-Pinene in an eastern white pine seed orchard. J Chem Ecol. 2003 Feb;29(2):437-51. doi: 10.1023/a:1022642314029. [PubMed:12737268  ] 
  5. LOTUS database [Link]