Np mrd loader

Showing NP-Card for umbellulone (NP0307696)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-09-11 01:00:20 UTC
Updated at2022-09-11 01:00:20 UTC
NP-MRD IDNP0307696
Secondary Accession NumbersNone
Natural Product Identification
Common Nameumbellulone
Description4-Methyl-1-(propan-2-yl)bicyclo[3.1.0]Hex-3-en-2-one belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. umbellulone is found in Chrysanthemum indicum, Daucus carota, Mentha longifolia, Ocimum gratissimum, Pimenta racemosa, Tanacetum vulgare and Umbellularia californica. 4-Methyl-1-(propan-2-yl)bicyclo[3.1.0]Hex-3-en-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0307696 (umbellulone)


  Mrv1533004191519542D          

 11 12  0  0  0  0            999 V2000
   -0.5992   -1.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213   -1.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062   -2.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569   -0.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1576   -0.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    0.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415    0.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8264   -0.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415   -1.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964   -1.8060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964    1.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 11  1  0  0  0  0
M  END
Download

3D MOL for NP0307696 (umbellulone)

     RDKit          3D

 25 26  0  0  0  0  0  0  0  0999 V2000
    3.2900    0.0167    0.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167   -0.3444    0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7943   -1.2750   -0.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3971   -1.2967   -1.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0721   -2.1497   -1.9429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2885   -0.1821   -0.4597 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7097   -0.3936    0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6821    0.1692   -0.9675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8609    0.3527    1.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232    1.1661   -0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7373    0.3591    0.4520 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6745    0.9954    0.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0242   -0.7859    0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0383    0.1112    1.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814   -1.9353   -1.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9356   -1.4520    0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6838   -0.3234   -0.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3162    0.0040   -2.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7638    1.2702   -0.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2844   -0.2327    2.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4005    1.3548    1.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9208    0.4837    1.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2971    2.0835   -0.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9125    1.3303   -1.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5259    0.6737    1.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  1  0
  6  7  1  1
  6 10  1  0
 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  0
  9 20  1  0
  9 21  1  0
  9 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  1
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
M  END
Download

3D SDF for NP0307696 (umbellulone)


  Mrv1533004191519542D          

 11 12  0  0  0  0            999 V2000
   -0.5992   -1.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213   -1.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062   -2.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569   -0.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1576   -0.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    0.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415    0.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8264   -0.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415   -1.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964   -1.8060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964    1.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0307696

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C12CC1C(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

> <INCHI_KEY>
LTTVJAQLCIHAFV-UHFFFAOYSA-N

> <FORMULA>
C10H14O

> <MOLECULAR_WEIGHT>
150.221

> <EXACT_MASS>
150.104465071

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.462157527032094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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>
45.3922

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
umbellulone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0307696 (umbellulone)

Download
PDB for NP0307696 (umbellulone)
HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -1.118  -2.999   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.413  -2.838   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.318  -4.083   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.039  -1.431   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.294  -0.661   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.039   0.109   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.504   0.585   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.409  -0.661   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.504  -1.907   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.980  -3.371   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.980   2.050   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6    9                                             
CONECT    5    4    6                                                       
CONECT    6    5    4    7                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    7                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

Download
3D PDB for NP0307696 (umbellulone)
Download
SMILES for NP0307696 (umbellulone)
CC(C)C12CC1C(C)=CC2=O
Download
INCHI for NP0307696 (umbellulone)
InChI=1S/C10H14O/c1-6(2)10-5-8(10)7(3)4-9(10)11/h4,6,8H,5H2,1-3H3
Download
View in JSmol
Synonyms
ValueSource
UmbelluloneMeSH
(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 Name4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hex-3-en-2-one
Traditional Nameumbellulone
CAS Registry NumberNot Available
SMILES
CC(C)C12CC1C(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
InChI KeyLTTVJAQLCIHAFV-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
Chrysanthemum indicumLOTUS Database
Daucus carotaLOTUS Database
Mentha longifoliaLOTUS Database
Ocimum gratissimumLOTUS Database
Pimenta racemosaLOTUS Database
Tanacetum vulgareLOTUS Database
Umbellularia californicaLOTUS 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
  • 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 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
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
Polarizability17.46 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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91195  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]