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Showing NP-Card for Carotol (NP0048539)

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Record Information
Version2.0
Created at2022-03-17 20:58:03 UTC
Updated at2022-03-17 20:58:03 UTC
NP-MRD IDNP0048539
Secondary Accession NumbersNone
Natural Product Identification
Common NameCarotol
DescriptionCarotol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Carotol is an extremely weak basic (essentially neutral) compound (based on its pKa). Carotol is a mild and pleasant tasting compound. Outside of the human body, Carotol is found, on average, in the highest concentration within wild carrots and carrots. Carotol has also been detected, but not quantified in, parsley and root vegetables. This could make carotol a potential biomarker for the consumption of these foods. Additionally, studies have shown that carotol may be involved in allelopathic interactions expressing activity as a antifungal, herbicidal and insecticidal agent. This later reaction, regardless of how plausible it may appear to be on paper, is energetically undesired and through the diligent work of M. Soucek and coworkers it was shown that the cyclization from FPP to carotol is the most probable biosynthesis route. Carotol was first isolated by scientists Asahina and Tsukamoto in 1925. ; It has been proposed that there is a direct cyclisation of farnesyl pyrophosphate (FPP) to the carotol (carotane backbone). This type of cyclisation is unconventional for the typical chemistry of sesquiterpenes. The only other proposed mechanism requires a complex ten-membered ring with a methyl migration. This sesquiterpene alcohol is thought to be formed in carrot seeds (Daucus carota L., Umbelliferae) during the vegetation period. Carotol is found in Alpinia latilabris, Eryngium foetidum, Ferula ovina, Ligusticum sinense, Micromeria sinaica and Thymus vulgaris. It is one of the primary components found in carrot seed oil comprising approximately 40% of this essential oil.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0048539 (Carotol)


  Mrv0541 05061309122D          

 16 17  0  0  0  0            999 V2000
    0.8611   -1.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2201   -2.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603    1.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680   -1.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603   -1.4297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14  4  1  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
M  END
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3D MOL for NP0048539 (Carotol)

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3D SDF for NP0048539 (Carotol)

  Mrv0541 05061309122D          

 16 17  0  0  0  0            999 V2000
    0.8611   -1.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2201   -2.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603    1.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680   -1.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603   -1.4297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14  4  1  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048539

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1CCC2(C)CC=C(C)CCC12O

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-11(2)13-7-9-14(4)8-5-12(3)6-10-15(13,14)16/h5,11,13,16H,6-10H2,1-4H3

> <INCHI_KEY>
XZYQCFABZDVOPN-UHFFFAOYSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.3663

> <EXACT_MASS>
222.198365454

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.505297290574735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-3a-ol

> <ALOGPS_LOGP>
4.65

> <JCHEM_LOGP>
3.785609167666667

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.26190218001724463

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
69.12599999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carotol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048539 (Carotol)
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PDB for NP0048539 (Carotol)
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       1.607  -3.414   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.144  -4.238   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.968  -0.384   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.779   1.902   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.760  -1.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.114  -3.094   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590  -1.629   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.779  -2.669   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   14                                                            
CONECT    5    8   12                                                       
CONECT    6   10   12                                                       
CONECT    7    9   13                                                       
CONECT    8    5   14                                                       
CONECT    9    7   14                                                       
CONECT   10    6   15                                                       
CONECT   11    1    2   13                                                  
CONECT   12    3    5    6                                                  
CONECT   13    7   11   15                                                  
CONECT   14    4    8    9   15                                             
CONECT   15   10   13   14   16                                             
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

Download
3D PDB for NP0048539 (Carotol)
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SMILES for NP0048539 (Carotol)
CC(C)C1CCC2(C)CC=C(C)CCC12O
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INCHI for NP0048539 (Carotol)
InChI=1S/C15H26O/c1-11(2)13-7-9-14(4)8-5-12(3)6-10-15(13,14)16/h5,11,13,16H,6-10H2,1-4H3
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Synonyms
ValueSource
(+)-CarotolHMDB
cis-Dauc-8-en-5beta -ol (carotol)HMDB
Chemical FormulaC15H26O
Average Mass222.3663 Da
Monoisotopic Mass222.19837 Da
IUPAC Name6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-3a-ol
Traditional Namecarotol
CAS Registry Number465-28-1
SMILES
CC(C)C1CCC2(C)CC=C(C)CCC12O
InChI Identifier
InChI=1S/C15H26O/c1-11(2)13-7-9-14(4)8-5-12(3)6-10-15(13,14)16/h5,11,13,16H,6-10H2,1-4H3
InChI KeyXZYQCFABZDVOPN-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Alpinia latilabrisLOTUS Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
    • David M. Alabran, Howard R. Moskowitz, and Ahmed F. Mabrouk. Carrot-Root Oil Components and Their...
Eryngium foetidumLOTUS Database
Ferula ovinaLOTUS Database
Ligusticum sinenseLOTUS Database
Micromeria sinaicaLOTUS Database
Petroselinum crispumFooDB
Thymus vulgarisLOTUS 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
  • Daucane sesquiterpenoid
    • 

  • Sesquiterpenoid
    • 

  • Tertiary alcohol
    • 

  • Cyclic alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP4.65ALOGPS
logP3.79ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)0.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.13 m³·mol⁻¹ChemAxon
Polarizability27.51 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036579  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015487  
KNApSAcK IDC00003109  
Chemspider ID253697  
KEGG Compound IDC09628  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarotol  
METLIN IDNot Available
PubChem Compound287687  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References