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Showing NP-Card for (-)-3-Thujen-2-one (NP0057837)

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Record Information
Version2.0
Created at2022-04-28 03:12:41 UTC
Updated at2022-04-28 03:12:41 UTC
NP-MRD IDNP0057837
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-3-Thujen-2-one
DescriptionUmbellulone belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (-)-3-Thujen-2-one is found in Ocimum gratissimum, Pimenta racemosa, Tanacetum vulgare and Umbellularia californica . (-)-3-Thujen-2-one was first documented in 2020 (PMID: 33131305). Based on a literature review a small amount of articles have been published on Umbellulone (PMID: 35325034) (PMID: 35295808) (PMID: 34830154) (PMID: 32985222).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0057837 ((-)-3-Thujen-2-one)


  Mrv1652304282205122D          

 11 12  0  0  1  0            999 V2000
    1.8264    1.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415    0.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    0.7665    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5569    1.5915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3415    1.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964    2.6310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1576    1.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213    2.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5992    2.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062    3.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964   -0.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  4  7  1  0  0  0  0
  3  7  1  6  0  0  0
  4  8  1  1  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  2 11  1  0  0  0  0
M  END
Download

3D MOL for NP0057837 ((-)-3-Thujen-2-one)

     RDKit          3D

 25 26  0  0  0  0  0  0  0  0999 V2000
    3.3576    0.2665   -0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9931   -0.2232   -0.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6535   -1.4747    0.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1952   -1.5727    0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4291   -2.6410    0.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3348   -0.2154    0.2972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7465    0.0526   -0.0649 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9304    1.4404   -0.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3831   -1.0074   -0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2160    0.7922    1.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7974    0.6467   -0.0417 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9199    0.4687    0.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9623   -0.4491   -0.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3781    1.2257   -0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3070   -2.3569    0.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3332    0.0914    0.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1645    1.6822   -1.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9465    1.4156   -1.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9480    2.2155    0.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7537   -1.3543   -1.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3852   -0.6382   -1.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5732   -1.9044   -0.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7274    0.3548    2.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3357    1.7068    1.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7565    1.4782   -0.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  1  0
  6  7  1  0
  6 10  1  1
 10 11  1  0
 11  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
 11  6  1  0
  4  6  1  0
  8 17  1  0
  8 18  1  0
  8 19  1  0
  7 16  1  1
  9 20  1  0
  9 21  1  0
  9 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  6
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
M  END
Download

3D SDF for NP0057837 ((-)-3-Thujen-2-one)


  Mrv1652304282205122D          

 11 12  0  0  1  0            999 V2000
    1.8264    1.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415    0.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    0.7665    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5569    1.5915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3415    1.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964    2.6310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1576    1.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213    2.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5992    2.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062    3.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964   -0.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  4  7  1  0  0  0  0
  3  7  1  6  0  0  0
  4  8  1  1  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  2 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057837

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@]12C[C@H]1C(C)=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O/c1-6(2)10-5-8(10)7(3)4-9(10)11/h4,6,8H,5H2,1-3H3/t8-,10+/m0/s1

> <INCHI_KEY>
LTTVJAQLCIHAFV-WCBMZHEXSA-N

> <FORMULA>
C10H14O

> <MOLECULAR_WEIGHT>
150.221

> <EXACT_MASS>
150.104465071

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.444842625265085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5S)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hex-3-en-2-one

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
2.494123231333334

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.283064587317984

> <JCHEM_PKA_STRONGEST_BASIC>
-4.868466778643954

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
45.392199999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thujen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0057837 ((-)-3-Thujen-2-one)

Download
PDB for NP0057837 ((-)-3-Thujen-2-one)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       3.409   2.201   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.504   0.955   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.039   1.431   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.039   2.971   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.504   3.447   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.980   4.911   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.294   2.201   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.413   4.378   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.118   4.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.318   5.623   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.980  -0.510   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    7    8                                             
CONECT    5    4    1    6                                                  
CONECT    6    5                                                            
CONECT    7    4    3                                                       
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    2                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

Download
3D PDB for NP0057837 ((-)-3-Thujen-2-one)
Download
SMILES for NP0057837 ((-)-3-Thujen-2-one)
CC(C)[C@]12C[C@H]1C(C)=CC2=O
Download
INCHI for NP0057837 ((-)-3-Thujen-2-one)
InChI=1S/C10H14O/c1-6(2)10-5-8(10)7(3)4-9(10)11/h4,6,8H,5H2,1-3H3/t8-,10+/m0/s1
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View in JSmol
Synonyms
ValueSource
(-)-UmbelluloneKegg
(1R,5S)-4-Methyl-1-propan-2-ylbicyclo(3.1.0)hex-3-en-2-oneMeSH
Chemical FormulaC10H14O
Average Mass150.2210 Da
Monoisotopic Mass150.10447 Da
IUPAC Name(1R,5S)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hex-3-en-2-one
Traditional Namethujen-2-one
CAS Registry NumberNot Available
SMILES
CC(C)[C@]12C[C@H]1C(C)=CC2=O
InChI Identifier
InChI=1S/C10H14O/c1-6(2)10-5-8(10)7(3)4-9(10)11/h4,6,8H,5H2,1-3H3/t8-,10+/m0/s1
InChI KeyLTTVJAQLCIHAFV-WCBMZHEXSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ocimum gratissimumLOTUS Database
Pimenta racemosaLOTUS Database
Tanacetum vulgareLOTUS Database
Umbellularia californicaPlant
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
  • Bicyclic monoterpenoid
    • 

  • Thujane monoterpenoid
    • 

  • Cyclohexenone
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP2.27ALOGPS
logP2.49ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)17.28ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.39 m³·mol⁻¹ChemAxon
Polarizability17.44 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 IDC00011054  
Chemspider ID390930  
KEGG Compound IDC09911  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkUmbellulone  
METLIN IDNot Available
PubChem Compound442504  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Watanabe M, Kopruszinski CM, Moutal A, Ikegami D, Khanna R, Chen Y, Ross S, Mackenzie K, Stratton J, Dodick DW, Navratilova E, Porreca F: Dysregulation of serum prolactin links the hypothalamus with female nociceptors to promote migraine. Brain. 2022 Mar 24. pii: 6553687. doi: 10.1093/brain/awac104. [PubMed:35325034  ] 
  2. Woodman SE, Antonopoulos SR, Durham PL: Inhibition of Nociception in a Preclinical Episodic Migraine Model by Dietary Supplementation of Grape Seed Extract Involves Activation of Endocannabinoid Receptors. Front Pain Res (Lausanne). 2022 Jan 27;3:809352. doi: 10.3389/fpain.2022.809352.  eCollection 2022. [PubMed:35295808  ] 
  3. Nie L, Jiang L, Quinn JP, Grubb BD, Wang M: TRPA1-Mediated Src Family Kinases Activity Facilitates Cortical Spreading Depression Susceptibility and Trigeminovascular System Sensitization. Int J Mol Sci. 2021 Nov 12;22(22). pii: ijms222212273. doi: 10.3390/ijms222212273. [PubMed:34830154  ] 
  4. Kopruszinski CM, Thornton P, Arnold J, Newton P, Lowne D, Navratilova E, Swiokla J, Dodick DW, Dobson C, Gurrell I, Chessell IP, Porreca F: Characterization and preclinical evaluation of a protease activated receptor 2 (PAR2) monoclonal antibody as a preventive therapy for migraine. Cephalalgia. 2020 Dec;40(14):1535-1550. doi: 10.1177/0333102420966581. Epub 2020  Nov 1. [PubMed:33131305  ] 
  5. Kopruszinski CM, Navratilova E, Swiokla J, Dodick DW, Chessell IP, Porreca F: A novel, injury-free rodent model of vulnerability for assessment of acute and preventive therapies reveals temporal contributions of CGRP-receptor activation in migraine-like pain. Cephalalgia. 2021 Mar;41(3):305-317. doi: 10.1177/0333102420959794. Epub 2020 Sep 26. [PubMed:32985222  ]