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Showing NP-Card for (-)-β-phellandrene (NP0185115)

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Record Information
Version2.0
Created at2022-09-04 00:25:34 UTC
Updated at2022-09-04 00:25:34 UTC
NP-MRD IDNP0185115
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-β-phellandrene
Description(-)-Beta-phellandrene, also known as b-phellandrene L-form, 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. (-)-β-phellandrene is found in Abies alba, Anthemis aciphylla, Aspergillus candidus, Cedrus libani, Eucalyptus cneorifolia, Picea abies, Picea sitchensis, Pinus monticola, Piper fimbriulatum, Plagiochila rutilans, Rhodiola rosea, Tsuga heterophylla and Valeriana officinalis. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes (-)-beta-phellandrene is possibly neutral.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0185115 ((-)-β-phellandrene)


  Mrv1652309272007282D          

 10 10  0  0  0  0            999 V2000
10001.095610000.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8103 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.095610001.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2396 9998.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.668910000.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.954410000.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9544 9999.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6689 9998.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3834 9999.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.383410000.0009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  1  1  1  0  0  0
  7  4  2  0  0  0  0
M  END
Download

3D MOL for NP0185115 ((-)-β-phellandrene)

     RDKit          3D

 26 26  0  0  0  0  0  0  0  0999 V2000
    3.5274    0.5278   -0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3236   -0.0079   -0.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3937    0.5172   -1.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1113    0.5674   -1.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2493    0.0772    0.2333 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7244    0.1385    0.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1849    1.5245    0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5307   -0.8499   -0.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -1.2175    0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8771   -1.1299    0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8355    1.3420   -0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2093    0.1327    0.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7183    0.8658   -2.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6101    0.9510   -1.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1867    0.8377    0.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9233    0.0500    1.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3891    1.5765   -1.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004    1.8316    0.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3615    2.2259    0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0814   -1.8315   -0.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5005   -0.9878    0.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7852   -0.4665   -1.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1993   -1.4299    1.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0028   -2.0896    0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4121   -1.0601    1.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2553   -2.0955   -0.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  1  0
  6  5  1  0
  5  9  1  0
  9 10  1  0
 10  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  7 17  1  0
  7 18  1  0
  7 19  1  0
  6 16  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
  5 15  1  1
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
M  END
Download

3D SDF for NP0185115 ((-)-β-phellandrene)


  Mrv1652309272007282D          

 10 10  0  0  0  0            999 V2000
10001.095610000.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8103 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.095610001.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2396 9998.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.668910000.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.954410000.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9544 9999.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6689 9998.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3834 9999.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.383410000.0009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  1  1  1  0  0  0
  7  4  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0185115

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8,10H,3,5,7H2,1-2H3/t10-/m1/s1

> <INCHI_KEY>
LFJQCDVYDGGFCH-SNVBAGLBSA-N

> <FORMULA>
C10H16

> <MOLECULAR_WEIGHT>
136.238

> <EXACT_MASS>
136.125200515

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.444509202711764

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R)-3-methylidene-6-(propan-2-yl)cyclohex-1-ene

> <ALOGPS_LOGP>
3.98

> <JCHEM_LOGP>
3.263470476333333

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
46.746900000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-β-phellandrene

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0185115 ((-)-β-phellandrene)

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PDB for NP0185115 ((-)-β-phellandrene)
HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8668.7128667.436   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8670.0468666.666   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8668.7128668.974   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.3818664.359   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8666.0498667.438   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8664.7158666.668   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8664.7158665.128   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8666.0498664.358   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8667.3828665.128   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8667.3828666.668   0.000  0.00  0.00           C+0
CONECT    1    2    3   10                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    7                                                            
CONECT    5    6   10                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    4                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    5    9    1                                                  
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0185115 ((-)-β-phellandrene)
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SMILES for NP0185115 ((-)-β-phellandrene)
CC(C)[C@H]1CCC(=C)C=C1
Download
INCHI for NP0185115 ((-)-β-phellandrene)
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8,10H,3,5,7H2,1-2H3/t10-/m1/s1
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View in JSmol
Synonyms
ValueSource
(-)-3-Methylene-6-(1-methylethyl)cyclohexeneChEBI
(-)-p-Mentha-1(7),2-dieneChEBI
(3R)-3-Isopropyl-6-methylenecyclohexeneChEBI
(R)-3-Isopropyl-6-methylenecyclohexeneChEBI
beta-Phellandrene L-formChEBI
b-Phellandrene L-formGenerator
Β-phellandrene L-formGenerator
(-)-b-PhellandreneGenerator
(-)-Β-phellandreneGenerator
(6R)-3-Methylene-6-(1-methylethyl)cyclohexenePhytoBank
(-)-beta-PhellandrenePhytoBank
l-beta-PhellandrenePhytoBank
l-β-PhellandrenePhytoBank
p-Mentha-1(7),2-dienePhytoBank
3-Methylene-6-(1-methylethyl)cyclohexenePhytoBank
(±)-beta-PhellandrenePhytoBank
(±)-β-PhellandrenePhytoBank
3-Isopropyl-6-methylene-1-cyclohexenePhytoBank
4-Isopropyl-1-methylene-2-cyclohexenePhytoBank
beta-PhellandrenePhytoBank
Chemical FormulaC10H16
Average Mass136.2380 Da
Monoisotopic Mass136.12520 Da
IUPAC Name(6R)-3-methylidene-6-(propan-2-yl)cyclohex-1-ene
Traditional Name(-)-β-phellandrene
CAS Registry NumberNot Available
SMILES
CC(C)[C@H]1CCC(=C)C=C1
InChI Identifier
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8,10H,3,5,7H2,1-2H3/t10-/m1/s1
InChI KeyLFJQCDVYDGGFCH-SNVBAGLBSA-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
Abies albaLOTUS Database
Anthemis aciphyllaLOTUS Database
Aspergillus candidusLOTUS Database
Cedrus libaniLOTUS Database
Eucalyptus cneorifoliaLOTUS Database
Picea abiesLOTUS Database
Picea sitchensisLOTUS Database
Pinus monticolaLOTUS Database
Piper fimbriulatumLOTUS Database
Plagiochila rutilansLOTUS Database
Rhodiola roseaLOTUS Database
Tsuga heterophyllaLOTUS Database
Valeriana officinalisLOTUS 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
    • 

  • Branched unsaturated hydrocarbon
    • 

  • Cycloalkene
    • 

  • Cyclic olefin
    • 

  • Unsaturated aliphatic hydrocarbon
    • 

  • Unsaturated hydrocarbon
    • 

  • Olefin
    • 

  • Hydrocarbon
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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
logP3.98ALOGPS
logP3.26ChemAxon
logS-3.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.75 m³·mol⁻¹ChemAxon
Polarizability17.44 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 IDC00010873  
Chemspider IDNot Available
KEGG Compound IDC11392  
BioCyc IDCPD-8768  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443161  
PDB IDNot Available
ChEBI ID129  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]