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Showing NP-Card for Dihydrocitronellol (NP0048238)

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Record Information
Version2.0
Created at2022-03-17 20:53:18 UTC
Updated at2022-03-17 20:53:18 UTC
NP-MRD IDNP0048238
Secondary Accession NumbersNone
Natural Product Identification
Common NameDihydrocitronellol
Description(R)-Dihydrocitronellol, also known as 3,7-dimethyl-1-octanol or geraniol tetrahydride, belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Thus, (R)-dihydrocitronellol is considered to be a fatty alcohol lipid molecule (R)-Dihydrocitronellol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (R)-Dihydrocitronellol is an aldehydic, bitter, and citrus tasting compound. Outside of the human body, (R)-Dihydrocitronellol is found, on average, in the highest concentration within lemons. Dihydrocitronellol was first documented in 1969 (PMID: 5370660). This could make (R)-dihydrocitronellol a potential biomarker for the consumption of these foods (PMID: 9795085) (PMID: 21959804) (PMID: 4304160) (PMID: 9775437).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048238 (Dihydrocitronellol)


  Mrv0541 02241219222D          

 11 10  0  0  0  0            999 V2000
    1.4287   -0.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7151   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150   -0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150    0.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4288   -0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1437   -0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573   -0.6195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8573   -0.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
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3D MOL for NP0048238 (Dihydrocitronellol)

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3D SDF for NP0048238 (Dihydrocitronellol)

  Mrv0541 02241219222D          

 11 10  0  0  0  0            999 V2000
    1.4287   -0.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7151   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150   -0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150    0.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4288   -0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1437   -0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573   -0.6195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8573   -0.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048238

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCCC(C)CCO

> <INCHI_IDENTIFIER>
InChI=1S/C10H22O/c1-9(2)5-4-6-10(3)7-8-11/h9-11H,4-8H2,1-3H3

> <INCHI_KEY>
PRNCMAKCNVRZFX-UHFFFAOYSA-N

> <FORMULA>
C10H22O

> <MOLECULAR_WEIGHT>
158.2811

> <EXACT_MASS>
158.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
20.971646186749517

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,7-dimethyloctan-1-ol

> <ALOGPS_LOGP>
3.96

> <JCHEM_LOGP>
3.157634798666667

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.109798188842703

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8759742722002013

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
49.6361

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,7-dimethyloctan-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048238 (Dihydrocitronellol)
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PDB for NP0048238 (Dihydrocitronellol)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.667  -1.154   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.335  -0.384   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -1.154   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.335  -0.386   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.335   1.154   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -1.156   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.002  -0.386   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.334  -1.156   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.002   1.156   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.002  -0.384   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.334  -1.154   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    1    9   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0048238 (Dihydrocitronellol)
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SMILES for NP0048238 (Dihydrocitronellol)
CC(C)CCCC(C)CCO
Download
INCHI for NP0048238 (Dihydrocitronellol)
InChI=1S/C10H22O/c1-9(2)5-4-6-10(3)7-8-11/h9-11H,4-8H2,1-3H3
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View in JSmol
Synonyms
ValueSource
2,6-Dimethyl-8-octanolHMDB
3,7-Dimethyl-(.+/-.)-1-octanolHMDB
3,7-Dimethyl-(R)-1-octanolHMDB
3,7-Dimethyl-(S)-1-octanolHMDB
3,7-DIMETHYL-1-octanolHMDB
3,7-Dimethyloctan-1-olHMDB
Dihydro-citronellolHMDB
Dimethyl octanolHMDB
Dimethyl-1-octanolHMDB
Dimethyloctan-2-olHMDB
DimethyloctanolHMDB
Geraniol tetrahydrideHMDB
PelargolHMDB
Perhydro-geraniolHMDB
S-3,7-Dimethyl-1-octanolHMDB
Tetrahydro-geraniolHMDB
DihydrocitronellolMeSH
3,7-Dimethyloctan-1-ol, titanium saltMeSH
TetrahydrogeraniolMeSH
Chemical FormulaC10H22O
Average Mass158.2811 Da
Monoisotopic Mass158.16707 Da
IUPAC Name3,7-dimethyloctan-1-ol
Traditional Name3,7-dimethyloctan-1-ol
CAS Registry Number106-21-8
SMILES
CC(C)CCCC(C)CCO
InChI Identifier
InChI=1S/C10H22O/c1-9(2)5-4-6-10(3)7-8-11/h9-11H,4-8H2,1-3H3
InChI KeyPRNCMAKCNVRZFX-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Citrus limonFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty alcohols  
Direct ParentFatty alcohols  
Alternative Parents
Substituents
  • Fatty alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP3.96ALOGPS
logP3.16ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)17.11ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity49.64 m³·mol⁻¹ChemAxon
Polarizability20.97 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035411  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014093  
KNApSAcK IDNot Available
Chemspider ID7504  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7792  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Joglekar SS, Dhavlikar RS: Microbial transformation of terpenoids. I. Identification of metabolites produced by a pseudomonad from citronellal and citral. Appl Microbiol. 1969 Dec;18(6):1084-7. doi: 10.1128/am.18.6.1084-1087.1969. [PubMed:5370660  ] 
  2. Hanif RM, Qineng P, Zhan G: Penetration enhancing effect of tetrahydrogeraniol on the percutaneous absorption of 5-fluorouracil from gels in excised rat skin. J Control Release. 1998 Nov 13;55(2-3):297-302. doi: 10.1016/s0168-3659(98)00062-5. [PubMed:9795085  ] 
  3. Khan GM, Hussain A, Hanif RM: Preparation and evaluation of 5, 9-dimethyl-2-cyclopropyl-2-decanol as a penetration enhancer for drugs through rat skin. Pak J Pharm Sci. 2011 Oct;24(4):451-7. [PubMed:21959804  ] 
  4. Popjak G, Holloway PW, Bond RP, Roberts M: Analogues of geranyl pyrophosphate as inhibitors of prenyltransferase. Biochem J. 1969 Feb;111(3):333-43. doi: 10.1042/bj1110333. [PubMed:4304160  ] 
  5. Hanif RM, Ping Q, Muo F: Synthesis and effect of two new penetration enhancers on the transdermal delivery of 5-fluorouracil through excised rat skin. Chem Pharm Bull (Tokyo). 1998 Sep;46(9):1428-31. doi: 10.1248/cpb.46.1428. [PubMed:9775437  ]