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Showing NP-Card for limonene-1,2-epoxide (NP0296342)

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Record Information
Version2.0
Created at2022-09-10 05:51:52 UTC
Updated at2022-09-10 05:51:53 UTC
NP-MRD IDNP0296342
Secondary Accession NumbersNone
Natural Product Identification
Common Namelimonene-1,2-epoxide
Description limonene-1,2-epoxide is found in Aloysia triphylla, Origanum minutiflorum, Perilla frutescens, Solanum tuberosum and Tagetes minuta.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0296342 (limonene-1,2-epoxide)

 
  Mrv1533006051516592D          
 
 11 12  0  0  1  0            999 V2000
   16.9909   -8.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7023   -9.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6130   -8.6783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2728   -9.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9909   -8.1014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7023  -10.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2728  -10.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9909  -10.6198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.9909  -11.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2761  -11.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7057  -11.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  4  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  2  3  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
Download

3D MOL for NP0296342 (limonene-1,2-epoxide)

     RDKit          3D

 27 28  0  0  0  0  0  0  0  0999 V2000
    1.7650    1.1730   -1.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9264    0.3402   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1712    0.4273    0.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058   -0.6929    0.0659 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1345   -0.7874   -0.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3709    0.0243   -0.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9225   -0.3022    0.6940 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1914    0.4155    1.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7644   -1.6528    0.9980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0350   -0.7332    1.6960 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3887   -0.4071    1.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5628    1.9189   -1.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9013    1.1531   -1.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5560    1.4584    0.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9486   -0.2735    0.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9211    0.2343    1.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4461   -1.7057    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4902   -1.8785   -1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1800   -0.6041   -2.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1469   -0.2956   -1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2388    1.1137   -0.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3591    1.2742    0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1574    0.8592    2.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0819   -0.2537    0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461   -0.6433    2.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961    0.7075    1.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0699   -0.8694    2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11  4  1  0
 10  7  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  1 12  1  0
  1 13  1  0
  4 17  1  1
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
 10 25  1  1
 11 26  1  0
 11 27  1  0
M  END
Download

3D SDF for NP0296342 (limonene-1,2-epoxide)

 
  Mrv1533006051516592D          
 
 11 12  0  0  1  0            999 V2000
   16.9909   -8.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7023   -9.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6130   -8.6783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2728   -9.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9909   -8.1014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7023  -10.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2728  -10.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9909  -10.6198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.9909  -11.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2761  -11.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7057  -11.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  4  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  2  3  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296342

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@@H]1CCC2(C)OC2C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3/t8-,9?,10?/m1/s1

> <INCHI_KEY>
CCEFMUBVSUDRLG-XNWIYYODSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.237

> <EXACT_MASS>
152.120115135

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
17.75418921129649

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
2.319031143333333

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.224524158920892

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
45.24079999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-limonene oxide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0296342 (limonene-1,2-epoxide)

Download
PDB for NP0296342 (limonene-1,2-epoxide)
HEADER    PROTEIN                                 05-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-JUN-15         0                                  
HETATM    1  C   UNK     0      31.716 -16.745   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      33.044 -17.508   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      32.878 -16.199   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      30.376 -17.508   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.716 -15.123   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.044 -19.053   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      30.376 -19.053   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.716 -19.824   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.716 -21.363   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.382 -22.132   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.051 -22.132   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6    3                                                  
CONECT    3    1    2                                                       
CONECT    4    1    7                                                       
CONECT    5    1                                                            
CONECT    6    2    8                                                       
CONECT    7    4    8                                                       
CONECT    8    6    9    7                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0296342 (limonene-1,2-epoxide)
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SMILES for NP0296342 (limonene-1,2-epoxide)
CC(=C)[C@@H]1CCC2(C)OC2C1
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INCHI for NP0296342 (limonene-1,2-epoxide)
InChI=1S/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3/t8-,9?,10?/m1/s1
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View in JSmol
Synonyms
ValueSource
(+)-Limonene oxideChEBI
(4R)-4-Isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptaneChEBI
(4R)-Limonene-1,2-epoxideChEBI
(R)-(+)-Limonene oxideChEBI
1,2-Epoxy-4betah-p-menth-8-eneChEBI
Limonene oxideChEBI
Limonene-1,2-epoxideChEBI
Limonene-1,2-epoxide, cis-isomerMeSH
Limonene-1,2-epoxide, trans-isomerMeSH
Limonene-1,2-oxideMeSH
Limonene-1,2-epoxide, trans-(+)-isomerMeSH
LimoxideMeSH
Limonene-1,2-epoxide, cis-(+)-isomerMeSH
Limonene-1,2-epoxide, (1R-(1alpha,4beta,6alpha))-isomerMeSH
Limonene-1,2-epoxide, (1S-(1alpha,4alpha,6alpha))-isomerMeSH
Chemical FormulaC10H16O
Average Mass152.2370 Da
Monoisotopic Mass152.12012 Da
IUPAC Name(4R)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane
Traditional Name(+)-limonene oxide
CAS Registry NumberNot Available
SMILES
CC(=C)[C@@H]1CCC2(C)OC2C1
InChI Identifier
InChI=1S/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3/t8-,9?,10?/m1/s1
InChI KeyCCEFMUBVSUDRLG-XNWIYYODSA-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
Aloysia triphyllaLOTUS Database
Origanum minutiflorumLOTUS Database
Perilla frutescensLOTUS Database
Solanum tuberosumLOTUS Database
Tagetes minutaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassOxepanes  
Sub ClassNot Available
Direct ParentOxepanes  
Alternative Parents
Substituents
  • Oxepane
    • 

  • Oxacycle
    • 

  • 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
logP2.81ALOGPS
logP2.32ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.24 m³·mol⁻¹ChemAxon
Polarizability17.75 ųChemAxon
Number of Rings2ChemAxon
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 IDC00035852  
Chemspider IDNot Available
KEGG Compound IDC07271  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound441245  
PDB IDNot Available
ChEBI ID35672  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]