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Showing NP-Card for 1-Phenylethanol (NP0047417)

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Record Information
Version2.0
Created at2022-03-17 20:39:52 UTC
Updated at2022-03-17 20:39:52 UTC
NP-MRD IDNP0047417
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-Phenylethanol
Description1-Phenylethanol, also known as styrallyl alcohol or alpha, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. 1-Phenylethanol is an extremely weak basic (essentially neutral) compound (based on its pKa). 1-Phenylethanol is a sweet, acetophenone, and fresh tasting compound. Outside of the human body, 1-Phenylethanol has been detected, but not quantified in, several different foods, such as nuts, pears, alcoholic beverages, tea, and cocoa and cocoa products. This could make 1-phenylethanol a potential biomarker for the consumption of these foods. 1-Phenylethanol is found in Achillea abrotanoides, Castanopsis cuspidata, Cedronella canariensis, Cichorium endivia, Cyperus conglomeratus, Dicranopteris linearis, Gonioctena viminalis, Grosmannia crassivaginata, Hyssopus officinalis, Mus musculus, Peristeria elata, Physarum polycephalum, Platostoma africanum, Plumeria rubra, Sergia lucens, Trifolium pratense and Triticum aestivum. 1-Phenylethanol was first documented in 1994 (PMID: 18618554). An aromatic alcohol that is ethanol substituted by a phenyl group at position 1 (PMID: 16226717) (PMID: 24392725) (PMID: 24945457) (PMID: 18803305) (PMID: 18258789).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047417 (1-Phenylethanol)


  Mrv0541 05061306362D          

  9  9  0  0  0  0            999 V2000
    0.0000    2.4750    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
    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
    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
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  1  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
M  END
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3D MOL for NP0047417 (1-Phenylethanol)

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3D SDF for NP0047417 (1-Phenylethanol)

  Mrv0541 05061306362D          

  9  9  0  0  0  0            999 V2000
    0.0000    2.4750    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
    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
    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
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  1  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047417

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O/c1-7(9)8-5-3-2-4-6-8/h2-7,9H,1H3

> <INCHI_KEY>
WAPNOHKVXSQRPX-UHFFFAOYSA-N

> <FORMULA>
C8H10O

> <MOLECULAR_WEIGHT>
122.1644

> <EXACT_MASS>
122.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
13.711009185364755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-phenylethan-1-ol

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
1.6224710733333327

> <ALOGPS_LOGS>
-0.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.807494219723608

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8830020282928936

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
37.292699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-phenethyl alcohol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047417 (1-Phenylethanol)
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PDB for NP0047417 (1-Phenylethanol)
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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    8                                                       
CONECT    6    4    8                                                       
CONECT    7    1    8    9                                                  
CONECT    8    5    6    7                                                  
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0047417 (1-Phenylethanol)
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SMILES for NP0047417 (1-Phenylethanol)
CC(O)C1=CC=CC=C1
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INCHI for NP0047417 (1-Phenylethanol)
InChI=1S/C8H10O/c1-7(9)8-5-3-2-4-6-8/h2-7,9H,1H3
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Synonyms
ValueSource
(1-Hydroxyethyl)benzeneChEBI
1-Phenethyl alcoholChEBI
alpha-MethylbenzenemethanolChEBI
alpha-Methylbenzyl alcoholChEBI
alpha-PhenylethanolChEBI
alpha-Phenylethyl alcoholChEBI
Methylphenyl carbinolChEBI
Styrallyl alcoholChEBI
a-MethylbenzenemethanolGenerator
Α-methylbenzenemethanolGenerator
a-Methylbenzyl alcoholGenerator
Α-methylbenzyl alcoholGenerator
a-PhenylethanolGenerator
Α-phenylethanolGenerator
a-Phenylethyl alcoholGenerator
Α-phenylethyl alcoholGenerator
(1)-alpha-Methylbenzyl alcoholHMDB
1-(Phenylethyl) alcoholHMDB
1-Phenyl ethyl alcoholHMDB
1-Phenyl-1-hydroxyethaneHMDB
1-Phenyl-ethanolHMDB
1-Phenylethan-1-olHMDB
1-Phenylethyl alcoholHMDB
a-HydroxyethylbenzeneHMDB
a-Methylbenzenemethanol, 9ciHMDB
a-Methylbenzyl alcohol, 8ciHMDB
Alcohol methyl benzylicHMDB
alphaHMDB
alpha-HydroxyethylbenzeneHMDB
alpha-Methyl-benzenemethanolHMDB
alpha-Methyl-benzmethanolHMDB
alpha-Methyl-benzyl alcoholHMDB
alpha-Phenethyl alcoholHMDB
FEMA 2685HMDB
Methyl phenyl carbinolHMDB
Methyl phenyl methanolHMDB
Methylphenyl-methanolHMDB
MethylphenylcarbinolHMDB
Phenethyl alcoholHMDB
PhenylmethylcarbinolHMDB
Sec-phenethyl alcoholHMDB
Styralyl alcoholHMDB
Styrene alcoholHMDB
Chemical FormulaC8H10O
Average Mass122.1644 Da
Monoisotopic Mass122.07316 Da
IUPAC Name1-phenylethan-1-ol
Traditional Nameα-phenethyl alcohol
CAS Registry Number98-85-1
SMILES
CC(O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H10O/c1-7(9)8-5-3-2-4-6-8/h2-7,9H,1H3
InChI KeyWAPNOHKVXSQRPX-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea abrotanoidesLOTUS Database
Agaricus bisporusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Allium cepaFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Allium fistulosumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Castanopsis cuspidataLOTUS Database
Cedronella canariensisLOTUS Database
Cichorium endiviaLOTUS Database
Cyperus conglomeratusLOTUS Database
Dicranopteris linearisLOTUS Database
Gonioctena viminalisLOTUS Database
Grosmannia crassivaginataLOTUS Database
Hyssopus officinalis L.LOTUS Database
Mus musculusLOTUS Database
Peristeria elataLOTUS Database
Physarum polycephalumLOTUS Database
Platostoma africanumLOTUS Database
Pleurotus ostreatusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Plumeria rubraLOTUS Database
Pyrus communisFooDB
    • Christian Chervin, Jim Speirs, Brian Loveys, Brian D Patterson. Influence of low oxygen storage o...
Sergia lucensLOTUS Database
Theobroma cacaoFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Trifolium pratenseLOTUS Database
Triticum aestivumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives  
Alternative Parents
Substituents
  • Monocyclic benzene moiety
    • 

  • Secondary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic alcohol
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
logP1.58ALOGPS
logP1.62ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)14.81ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.29 m³·mol⁻¹ChemAxon
Polarizability13.71 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032619  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010561  
KNApSAcK IDNot Available
Chemspider ID7131  
KEGG Compound IDC07112  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1-Phenylethanol  
METLIN IDNot Available
PubChem Compound7409  
PDB IDNot Available
ChEBI ID669  
Good Scents IDNot Available
References
General References
  1. Vatsis KP, Coon MJ: Oxidative aldehyde deformylation catalyzed by NADPH-cytochrome P450 reductase and the flavoprotein domain of neuronal nitric oxide synthase. Biochem Biophys Res Commun. 2005 Dec 2;337(4):1107-11. doi: 10.1016/j.bbrc.2005.09.167. Epub 2005 Oct 5. [PubMed:16226717  ] 
  2. Li P, He Y, Guang J, Weng L, Zhao JC, Xiang S, Chen B: A homochiral microporous hydrogen-bonded organic framework for highly enantioselective separation of secondary alcohols. J Am Chem Soc. 2014 Jan 15;136(2):547-9. doi: 10.1021/ja4129795. Epub 2014 Jan 6. [PubMed:24392725  ] 
  3. Capraro MG, Franchi P, Lanzalunga O, Lapi A, Lucarini M: Chiral N-hydroxybenzamides as potential catalysts for aerobic asymmetric oxidations. J Org Chem. 2014 Jul 18;79(14):6435-43. doi: 10.1021/jo500844c. Epub 2014 Jul 1. [PubMed:24945457  ] 
  4. Kaur C, Sivakumar V, Yip GW, Ling EA: Expression of syndecan-2 in the amoeboid microglial cells and its involvement in inflammation in the hypoxic developing brain. Glia. 2009 Feb;57(3):336-49. doi: 10.1002/glia.20764. [PubMed:18803305  ] 
  5. Page AJ, O'Donnell TA, Blackshaw LA: Opioid modulation of ferret vagal afferent mechanosensitivity. Am J Physiol Gastrointest Liver Physiol. 2008 Apr;294(4):G963-70. doi: 10.1152/ajpgi.00562.2007. Epub 2008 Feb 7. [PubMed:18258789  ] 
  6. Orsat B, Drtina GJ, Williams MG, Klibanov AM: Effect of support material and enzyme pretreatment on enantioselectivity of immobilized subtilisin in organic solvents. Biotechnol Bioeng. 1994 Nov 20;44(10):1265-9. doi: 10.1002/bit.260441015. [PubMed:18618554  ]