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Showing NP-Card for α-pinene oxide (NP0324655)

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Record Information
Version1.0
Created at2022-09-12 04:52:18 UTC
Updated at2022-09-12 04:52:18 UTC
NP-MRD IDNP0324655
Secondary Accession NumbersNone
Natural Product Identification
Common Nameα-pinene oxide
DescriptionAlpha-Pinene-oxide, also known as 2-pinene oxide or 2,3-epoxy-pinane, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. α-pinene oxide is found in Daucus carota, Homo sapiens and Pistacia atlantica. It was first documented in 1987 (PMID: 3667521). Alpha-Pinene-oxide is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 12576684) (PMID: 16321051).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0324655 (α-pinene oxide)


  Mrv0541 02231219472D          

 11 13  0  0  0  0            999 V2000
   11.0503  -11.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2076  -11.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4781   -8.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6553   -8.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5939  -10.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3042   -8.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9802  -10.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6251  -10.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7990   -9.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0503   -9.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8559  -10.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for NP0324655 (α-pinene oxide)

     RDKit          3D

 27 29  0  0  0  0  0  0  0  0999 V2000
    2.2017   -1.1731    0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0659   -0.2347   -0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328    0.3169   -1.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8114    0.7765    1.0161 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1193    1.8128    0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4018    1.2713   -0.0364 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2517    0.5913    0.8318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4414   -0.1165   -0.2009 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3564   -0.9163   -1.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2666   -0.8576    0.3317 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0407   -0.3355    1.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0173   -2.1630   -0.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1652   -0.7249   -0.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3462   -1.3640    1.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4016   -0.4742   -2.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2442    0.8268   -1.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9625    1.0833   -1.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6736    1.1657    1.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3753    2.3921   -0.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3592    2.5080    1.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9689    2.0134   -0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3159   -2.0057   -0.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4129   -0.6329   -1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0706   -0.8992   -2.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2482   -1.9439    0.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8683    0.0745    2.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6427   -0.9910    2.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  6
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4 11  1  0
 11 10  1  0
 10  2  1  0
  2  1  1  0
  2  3  1  0
  6  8  1  0
  2  4  1  0
 10  8  1  0
  9 22  1  0
  9 23  1  0
  9 24  1  0
  6 21  1  6
  5 19  1  0
  5 20  1  0
  4 18  1  1
 11 26  1  0
 11 27  1  0
 10 25  1  1
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
M  END
Download

3D SDF for NP0324655 (α-pinene oxide)


  Mrv0541 02231219472D          

 11 13  0  0  0  0            999 V2000
   11.0503  -11.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2076  -11.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4781   -8.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6553   -8.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5939  -10.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3042   -8.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9802  -10.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6251  -10.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7990   -9.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0503   -9.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8559  -10.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0324655

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12OC1CC1CC2C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-9(2)6-4-7(9)10(3)8(5-6)11-10/h6-8H,4-5H2,1-3H3

> <INCHI_KEY>
NQFUSWIGRKFAHK-UHFFFAOYSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.2334

> <EXACT_MASS>
152.120115134

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
17.87941079230503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,7,7-trimethyl-3-oxatricyclo[4.1.1.0²,⁴]octane

> <ALOGPS_LOGP>
2.77

> <JCHEM_LOGP>
1.9788336679999998

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.226627812474885

> <JCHEM_POLAR_SURFACE_AREA>
12.53

> <JCHEM_REFRACTIVITY>
43.4058

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-pinene oxide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0324655 (α-pinene oxide)

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PDB for NP0324655 (α-pinene oxide)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      20.627 -21.067   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      22.788 -20.839   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.292 -15.116   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.757 -16.002   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.642 -20.329   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.968 -16.327   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.496 -19.819   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.567 -18.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.891 -17.559   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.627 -18.572   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.864 -19.073   0.000  0.00  0.00           C+0
CONECT    1    5    7                                                       
CONECT    2    5                                                            
CONECT    3    6                                                            
CONECT    4    6                                                            
CONECT    5    1    2    7    8                                             
CONECT    6    3    4    8    9                                             
CONECT    7    1    5   10                                                  
CONECT    8    5    6   11                                                  
CONECT    9    6   10   11                                                  
CONECT   10    7    9                                                       
CONECT   11    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   26    0
END

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3D PDB for NP0324655 (α-pinene oxide)
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SMILES for NP0324655 (α-pinene oxide)
CC12OC1CC1CC2C1(C)C
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INCHI for NP0324655 (α-pinene oxide)
InChI=1S/C10H16O/c1-9(2)6-4-7(9)10(3)8(5-6)11-10/h6-8H,4-5H2,1-3H3
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View in JSmol
Synonyms
ValueSource
2,7,7-Trimethyl-3-oxatricyclo[4.1.1.0(2,4)]octaneChEBI
2-Pinene oxideChEBI
alpha-Pinene epoxideChEBI
a-Pinene epoxideGenerator
Α-pinene epoxideGenerator
a-Pinene-oxideGenerator
Α-pinene-oxideGenerator
2,3-Epoxy-pinaneHMDB
2,3-EpoxypinaneHMDB
alpha-Pinene 2,3-oxideHMDB
alpha-Pinene oxideHMDB
Pinene oxideHMDB
alpha-Pinane oxideHMDB
a-Pinene oxideHMDB
Α-pinene oxideHMDB
alpha-Pinene-oxideChEBI
Chemical FormulaC10H16O
Average Mass152.2334 Da
Monoisotopic Mass152.12012 Da
IUPAC Name2,7,7-trimethyl-3-oxatricyclo[4.1.1.0²,⁴]octane
Traditional Nameα-pinene oxide
CAS Registry NumberNot Available
SMILES
CC12OC1CC1CC2C1(C)C
InChI Identifier
InChI=1S/C10H16O/c1-9(2)6-4-7(9)10(3)8(5-6)11-10/h6-8H,4-5H2,1-3H3
InChI KeyNQFUSWIGRKFAHK-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
Daucus carotaLOTUS Database
Homo sapiensLOTUS Database
Pistacia atlanticaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentBicyclic monoterpenoids  
Alternative Parents
Substituents
  • Pinane monoterpenoid
    • 

  • Oxepane
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Oxirane
    • 

  • Dialkyl ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
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
logP2.77ALOGPS
logP1.98ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.41 m³·mol⁻¹ChemAxon
Polarizability17.88 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003667  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023213  
KNApSAcK IDNot Available
Chemspider ID82629  
KEGG Compound IDC02759  
BioCyc IDALPHA-PINENE-OXIDE  
BiGG ID40512  
Wikipedia LinkNot Available
METLIN ID6974  
PubChem Compound91508  
PDB IDNot Available
ChEBI ID29060  
Good Scents IDNot Available
References
General References
  1. Vaddi HK, Ho PC, Chan YW, Chan SY: Oxide terpenes as human skin penetration enhancers of haloperidol from ethanol and propylene glycol and their modes of action on stratum corneum. Biol Pharm Bull. 2003 Feb;26(2):220-8. [PubMed:12576684  ] 
  2. Boontawan A, Stuckey DC: Mass transfer of terpenes through a silicone rubber membrane in a liquid-liquid contacting system. Biotechnol Prog. 2005 Nov-Dec;21(6):1680-7. doi: 10.1021/bp0501827. [PubMed:16321051  ] 
  3. Griffiths ET, Bociek SM, Harries PC, Jeffcoat R, Sissons DJ, Trudgill PW: Bacterial metabolism of alpha-pinene: pathway from alpha-pinene oxide to acyclic metabolites in Nocardia sp. strain P18.3. J Bacteriol. 1987 Nov;169(11):4972-9. doi: 10.1128/jb.169.11.4972-4979.1987. [PubMed:3667521  ] 
  4. LOTUS database [Link]