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Showing NP-Card for (R)-2,7(14),9-Bisabolatrien-11-ol (NP0048309)

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Record Information
Version2.0
Created at2022-03-17 20:54:25 UTC
Updated at2022-03-17 20:54:25 UTC
NP-MRD IDNP0048309
Secondary Accession NumbersNone
Natural Product Identification
Common Name(R)-2,7(14),9-Bisabolatrien-11-ol
Description(R)-2,7(14),9-Bisabolatrien-11-ol, also known as helianthol a or O-benzoylecgonine, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units (R)-2,7(14),9-Bisabolatrien-11-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (R)-2,7(14),9-Bisabolatrien-11-ol has been detected, but not quantified in, jerusalem artichokes and root vegetables. This could make (R)-2,7(14),9-bisabolatrien-11-ol a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048309 ((R)-2,7(14),9-Bisabolatrien-11-ol)


  Mrv0541 05061308412D          

 16 16  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  5  2  0  0  0  0
 12  1  1  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13  2  2  0  0  0  0
 13  6  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  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 11  1  0  0  0  0
 16 15  1  0  0  0  0
M  END
Download

3D MOL for NP0048309 ((R)-2,7(14),9-Bisabolatrien-11-ol)

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3D SDF for NP0048309 ((R)-2,7(14),9-Bisabolatrien-11-ol)

  Mrv0541 05061308412D          

 16 16  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  5  2  0  0  0  0
 12  1  1  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13  2  2  0  0  0  0
 13  6  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  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 11  1  0  0  0  0
 16 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048309

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CCC(CC1)C(=C)C\C=C\C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-12-7-9-14(10-8-12)13(2)6-5-11-15(3,4)16/h5,7,11,14,16H,2,6,8-10H2,1,3-4H3/b11-5+

> <INCHI_KEY>
UMHJVDDWUSONQN-VZUCSPMQSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.3505

> <EXACT_MASS>
220.18271539

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.18718838036358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-2-methyl-6-(4-methylcyclohex-3-en-1-yl)hepta-3,6-dien-2-ol

> <ALOGPS_LOGP>
4.84

> <JCHEM_LOGP>
3.6079775263333342

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.859962976882002

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5478521939118117

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
72.2316

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-2-methyl-6-(4-methylcyclohex-3-en-1-yl)hepta-3,6-dien-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0048309 ((R)-2,7(14),9-Bisabolatrien-11-ol)
Download
PDB for NP0048309 ((R)-2,7(14),9-Bisabolatrien-11-ol)
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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.461   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.541   8.470   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   13                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5    6   11                                                       
CONECT    6    5   13                                                       
CONECT    7    9   12                                                       
CONECT    8   10   12                                                       
CONECT    9    7   14                                                       
CONECT   10    8   14                                                       
CONECT   11    5   15                                                       
CONECT   12    1    7    8                                                  
CONECT   13    2    6   14                                                  
CONECT   14    9   10   13                                                  
CONECT   15    3    4   11   16                                             
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

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3D PDB for NP0048309 ((R)-2,7(14),9-Bisabolatrien-11-ol)
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SMILES for NP0048309 ((R)-2,7(14),9-Bisabolatrien-11-ol)
CC1=CCC(CC1)C(=C)C\C=C\C(C)(C)O
Download
INCHI for NP0048309 ((R)-2,7(14),9-Bisabolatrien-11-ol)
InChI=1S/C15H24O/c1-12-7-9-14(10-8-12)13(2)6-5-11-15(3,4)16/h5,7,11,14,16H,2,6,8-10H2,1,3-4H3/b11-5+
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View in JSmol
Synonyms
ValueSource
Helianthol aHMDB
O-BenzoylecgonineHMDB
Pseudocgonine benzoate (ester)HMDB
[R-(e)]-2-Methyl-6-(4-methyl-3-cyclohexen-1-yl)-4,6-heptadien-2-olHMDB
Chemical FormulaC15H24O
Average Mass220.3505 Da
Monoisotopic Mass220.18272 Da
IUPAC Name(3E)-2-methyl-6-(4-methylcyclohex-3-en-1-yl)hepta-3,6-dien-2-ol
Traditional Name(3E)-2-methyl-6-(4-methylcyclohex-3-en-1-yl)hepta-3,6-dien-2-ol
CAS Registry Number72916-06-4
SMILES
CC1=CCC(CC1)C(=C)C\C=C\C(C)(C)O
InChI Identifier
InChI=1S/C15H24O/c1-12-7-9-14(10-8-12)13(2)6-5-11-15(3,4)16/h5,7,11,14,16H,2,6,8-10H2,1,3-4H3/b11-5+
InChI KeyUMHJVDDWUSONQN-VZUCSPMQSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Helianthus tuberosusFooDB
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
  • Bisabolane sesquiterpenoid
    • 

  • Sesquiterpenoid
    • 

  • Tertiary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • 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
logP4.84ALOGPS
logP3.61ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)17.86ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.23 m³·mol⁻¹ChemAxon
Polarizability27.19 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035739  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014468  
KNApSAcK IDC00011637  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101417476  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References