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Showing NP-Card for beta-Betulenol (NP0048593)

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Record Information
Version2.0
Created at2022-03-17 20:58:56 UTC
Updated at2022-03-17 20:58:56 UTC
NP-MRD IDNP0048593
Secondary Accession NumbersNone
Natural Product Identification
Common Namebeta-Betulenol
DescriptionBeta-Betulenol, also known as β-betulenol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Beta-Betulenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, beta-Betulenol has been detected, but not quantified in, herbs and spices and peppermints. beta-Betulenol is found in Betula pendula, Betula pubescens, Centaurea atropurpurea, Curcuma mangga , Juniperus oxycedrus , Piper nigrum , Psidium guajava and Xylopia sericea . This could make beta-betulenol a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048593 (beta-Betulenol)


  Mrv0541 05061309202D          

 16 17  0  0  0  0            999 V2000
    3.1162    1.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3484   -0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734   -1.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0557    0.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412    1.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3378   -0.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412   -1.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287   -1.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734    0.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6877   -1.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287    0.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0557   -0.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9984    0.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9984   -0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734   -0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4629   -1.1396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 11  1  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15  2  1  0  0  0  0
 15  3  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
M  END
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3D MOL for NP0048593 (beta-Betulenol)

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3D SDF for NP0048593 (beta-Betulenol)

  Mrv0541 05061309202D          

 16 17  0  0  0  0            999 V2000
    3.1162    1.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3484   -0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734   -1.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0557    0.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412    1.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3378   -0.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412   -1.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287   -1.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734    0.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6877   -1.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287    0.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0557   -0.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9984    0.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9984   -0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734   -0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4629   -1.1396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 11  1  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15  2  1  0  0  0  0
 15  3  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC2C1CC\C(CO)=C/CCC2=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-11-5-4-6-12(10-16)7-8-14-13(11)9-15(14,2)3/h6,13-14,16H,1,4-5,7-10H2,2-3H3/b12-6+

> <INCHI_KEY>
MGIQTXDHQJGPEZ-WUXMJOGZSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.3505

> <EXACT_MASS>
220.18271539

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.12289509952959

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(4E)-11,11-dimethyl-8-methylidenebicyclo[7.2.0]undec-4-en-4-yl]methanol

> <ALOGPS_LOGP>
4.01

> <JCHEM_LOGP>
3.238538235000001

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.884794320379342

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9743909642660755

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
69.2271

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(4E)-11,11-dimethyl-8-methylidenebicyclo[7.2.0]undec-4-en-4-yl]methanol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048593 (beta-Betulenol)
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PDB for NP0048593 (beta-Betulenol)
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       5.817   3.067   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.517  -0.987   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.057  -2.527   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.437   1.230   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.104   2.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.964  -0.217   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.104  -2.434   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.587  -2.167   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.057   0.553   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.617  -2.654   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.587   1.733   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.437  -1.664   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.597   0.553   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.597  -0.987   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.057  -0.987   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.064  -2.127   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   15                                                            
CONECT    3   15                                                            
CONECT    4    5    6                                                       
CONECT    5    4   11                                                       
CONECT    6    4   12                                                       
CONECT    7    8   12                                                       
CONECT    8    7   14                                                       
CONECT    9   13   15                                                       
CONECT   10   12   16                                                       
CONECT   11    1    5   13                                                  
CONECT   12    6    7   10                                                  
CONECT   13    9   11   14                                                  
CONECT   14    8   13   15                                                  
CONECT   15    2    3    9   14                                             
CONECT   16   10                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

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3D PDB for NP0048593 (beta-Betulenol)
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SMILES for NP0048593 (beta-Betulenol)
CC1(C)CC2C1CC\C(CO)=C/CCC2=C
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INCHI for NP0048593 (beta-Betulenol)
InChI=1S/C15H24O/c1-11-5-4-6-12(10-16)7-8-14-13(11)9-15(14,2)3/h6,13-14,16H,1,4-5,7-10H2,2-3H3/b12-6+
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View in JSmol
Synonyms
ValueSource
b-BetulenolGenerator
Β-betulenolGenerator
6,10,10-Trimethyl-2-methylenebicyclo[7.2.0]undec-5-en-3-ol, 9ciHMDB
Bicyclo[7.2.0]undec-5-en-3-ol, 6,10,10-trimethyl-2-methylene- (9ci)HMDB
cis-beta-BetulenolHMDB
D-beta-BetulenolHMDB
Chemical FormulaC15H24O
Average Mass220.3505 Da
Monoisotopic Mass220.18272 Da
IUPAC Name[(4E)-11,11-dimethyl-8-methylidenebicyclo[7.2.0]undec-4-en-4-yl]methanol
Traditional Name[(4E)-11,11-dimethyl-8-methylidenebicyclo[7.2.0]undec-4-en-4-yl]methanol
CAS Registry Number487-87-6
SMILES
CC1(C)CC2C1CC\C(CO)=C/CCC2=C
InChI Identifier
InChI=1S/C15H24O/c1-11-5-4-6-12(10-16)7-8-14-13(11)9-15(14,2)3/h6,13-14,16H,1,4-5,7-10H2,2-3H3/b12-6+
InChI KeyMGIQTXDHQJGPEZ-WUXMJOGZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Betula pendulaLOTUS Database
Betula pubescensLOTUS Database
Centaurea atropurpureaPlant
Curcuma manggaPlant
Juniperus oxycedrusPlant
Mentha x piperitaFooDB
Piper nigrum L.Plant
Psidium guajavaPlant
Xylopia sericeaPlant
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
  • Caryophyllane sesquiterpenoid
    • 

  • Sesquiterpenoid
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • 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
logP4.01ALOGPS
logP3.24ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)16.88ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.23 m³·mol⁻¹ChemAxon
Polarizability27.12 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036788  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015730  
KNApSAcK IDNot Available
Chemspider ID4474649  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5315299  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References