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Showing NP-Card for Humuladienone (NP0049056)

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Record Information
Version2.0
Created at2022-03-17 21:06:25 UTC
Updated at2022-03-17 21:06:25 UTC
NP-MRD IDNP0049056
Secondary Accession NumbersNone
Natural Product Identification
Common NameHumuladienone
DescriptionHumuladienone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Humuladienone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Humuladienone has been detected, but not quantified in, alcoholic beverages and wild celeries. Humuladienone is found in Helichrysum odoratissimum. This could make humuladienone a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049056 (Humuladienone)


  Mrv0541 05061310172D          

 16 16  0  0  0  0            999 V2000
    3.4464   -0.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3051   -1.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2811    1.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343    1.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2334    0.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371   -0.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0524   -0.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8710   -1.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0215    0.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929    1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4152    1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8401   -0.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4770   -1.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0833   -1.5863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5424    0.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9019   -2.3911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  5  2  0  0  0  0
 11  9  1  0  0  0  0
 12  1  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13  2  1  0  0  0  0
 13  6  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 14  2  0  0  0  0
M  END
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3D MOL for NP0049056 (Humuladienone)

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3D SDF for NP0049056 (Humuladienone)

  Mrv0541 05061310172D          

 16 16  0  0  0  0            999 V2000
    3.4464   -0.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3051   -1.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2811    1.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343    1.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2334    0.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371   -0.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0524   -0.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8710   -1.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0215    0.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929    1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4152    1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8401   -0.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4770   -1.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0833   -1.5863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5424    0.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9019   -2.3911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  5  2  0  0  0  0
 11  9  1  0  0  0  0
 12  1  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13  2  1  0  0  0  0
 13  6  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0049056

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C\C=C/C(C)(C)C\C=C(C)/CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-12-7-8-14(16)13(2)6-5-10-15(3,4)11-9-12/h5,9-10,13H,6-8,11H2,1-4H3/b10-5-,12-9-

> <INCHI_KEY>
XWFINABYEHNSEP-CGBKSYCJSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.3505

> <EXACT_MASS>
220.18271539

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.96515040008012

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4Z,8Z)-2,6,6,9-tetramethylcycloundeca-4,8-dien-1-one

> <ALOGPS_LOGP>
4.59

> <JCHEM_LOGP>
4.360608042666666

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.417562088120462

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
71.3658

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4Z,8Z)-2,6,6,9-tetramethylcycloundeca-4,8-dien-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0049056 (Humuladienone)
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PDB for NP0049056 (Humuladienone)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.433  -1.587   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.570  -2.406   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.391   3.034   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.611   2.928   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.436   1.085   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.189  -0.258   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.831  -1.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.493  -2.503   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.640   0.959   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.480   2.217   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.508   2.004   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.302  -0.543   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.890  -1.917   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.022  -2.961   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.879   1.573   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.684  -4.463   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   13                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5    6   10                                                       
CONECT    6    5   13                                                       
CONECT    7    8   12                                                       
CONECT    8    7   14                                                       
CONECT    9   11   12                                                       
CONECT   10    5   15                                                       
CONECT   11    9   15                                                       
CONECT   12    1    7    9                                                  
CONECT   13    2    6   14                                                  
CONECT   14    8   13   16                                                  
CONECT   15    3    4   10   11                                             
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

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3D PDB for NP0049056 (Humuladienone)
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SMILES for NP0049056 (Humuladienone)
CC1C\C=C/C(C)(C)C\C=C(C)/CCC1=O
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INCHI for NP0049056 (Humuladienone)
InChI=1S/C15H24O/c1-12-7-8-14(16)13(2)6-5-10-15(3,4)11-9-12/h5,9-10,13H,6-8,11H2,1-4H3/b10-5-,12-9-
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SynonymsNot Available
Chemical FormulaC15H24O
Average Mass220.3505 Da
Monoisotopic Mass220.18272 Da
IUPAC Name(4Z,8Z)-2,6,6,9-tetramethylcycloundeca-4,8-dien-1-one
Traditional Name(4Z,8Z)-2,6,6,9-tetramethylcycloundeca-4,8-dien-1-one
CAS Registry Number24405-90-1
SMILES
CC1C\C=C/C(C)(C)C\C=C(C)/CCC1=O
InChI Identifier
InChI=1S/C15H24O/c1-12-7-8-14(16)13(2)6-5-10-15(3,4)11-9-12/h5,9-10,13H,6-8,11H2,1-4H3/b10-5-,12-9-
InChI KeyXWFINABYEHNSEP-CGBKSYCJSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Apium graveolensFooDB
Helichrysum odoratissimumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentSesquiterpenoids  
Alternative Parents
Substituents
  • Humulane sesquiterpenoid
    • 

  • Sesquiterpenoid
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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
logP4.59ALOGPS
logP4.36ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.37 m³·mol⁻¹ChemAxon
Polarizability26.97 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038208  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB017450  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101297706  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References