Np mrd loader

Showing NP-Card for 3-Phenyl-2-propen-1-ol (NP0137409)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-05-30 16:51:39 UTC
Updated at2022-05-30 16:51:39 UTC
NP-MRD IDNP0137409
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Phenyl-2-propen-1-ol
DescriptionCinnamyl alcohol, also known as styrylcarbinol or zimtalcohol, belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety. Cinnamyl alcohol is an extremely weak basic (essentially neutral) compound (based on its pKa). Cinnamyl alcohol is a sweet, balsam, and bitter tasting compound. Outside of the human body, Cinnamyl alcohol is found, on average, in the highest concentration within ceylon cinnamons and star anises. Cinnamyl alcohol has also been detected, but not quantified in, several different foods, such as papaya, new zealand spinachs, wax apples, wild celeries, and eggplants. This could make cinnamyl alcohol a potential biomarker for the consumption of these foods. 3-Phenyl-2-propen-1-ol is found in Bidens graveolens, Cinnamomum aromaticum, Cinnamomum burmannii, Cinnamomum sieboldii, Cinnamomum verum, Cinnamomum yabunikkei, Citrullus lanatus, Coreopsis woytkowskii, Cryptocarya amygdalina, Ficus carica, Illicium verum, Lavandula angustifolia, Rhodiola rosea, Rhodiola sachalinensis, Syzygium jambos and Tetrapanax papyrifer. 3-Phenyl-2-propen-1-ol was first documented in 2013 (PMID: 23421457). A primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C=C bond unspecified) (PMID: 24190481).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0137409 (3-Phenyl-2-propen-1-ol)


  Mrv0541 02241217042D          

 10 10  0  0  0  0            999 V2000
    0.3296    1.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721   -0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -1.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  3  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
Download

3D MOL for NP0137409 (3-Phenyl-2-propen-1-ol)

     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
    3.8908   -0.8363   -0.7116 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1262   -0.6264    0.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6774   -0.7699    0.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8845    0.2539    0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5572    0.2777    0.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2856    1.4361    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6397    1.4738    0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2577    0.3568   -0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5564   -0.7742   -0.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1842   -0.8251   -0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5647   -0.1047   -0.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3906   -1.3889    1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2911    0.3717    0.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802   -1.6907   -0.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2996    1.2031    0.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7404    2.2933    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1950    2.3825    0.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3292    0.3911   -0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0300   -1.6780   -1.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6297   -1.7455   -0.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  4 15  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
M  END
Download

3D SDF for NP0137409 (3-Phenyl-2-propen-1-ol)


  Mrv0541 02241217042D          

 10 10  0  0  0  0            999 V2000
    0.3296    1.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721   -0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -1.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  3  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0137409

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC=CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2

> <INCHI_KEY>
OOCCDEMITAIZTP-UHFFFAOYSA-N

> <FORMULA>
C9H10O

> <MOLECULAR_WEIGHT>
134.1751

> <EXACT_MASS>
134.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
15.201600156828054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-phenylprop-2-en-1-ol

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
1.8158117219999996

> <ALOGPS_LOGS>
-1.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.62297059992013

> <JCHEM_PKA_STRONGEST_BASIC>
-2.526312659594935

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
43.19250000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-phenyl-2-propen-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0137409 (3-Phenyl-2-propen-1-ol)

Download
PDB for NP0137409 (3-Phenyl-2-propen-1-ol)
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  O   UNK     0       0.615   3.464   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.615   1.924   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.001   1.154   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.001  -0.386   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.615  -1.154   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.615  -0.386   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.001  -1.154   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.001  -2.694   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.615  -3.464   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.615  -2.694   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    5    9                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

Download
3D PDB for NP0137409 (3-Phenyl-2-propen-1-ol)
Download
SMILES for NP0137409 (3-Phenyl-2-propen-1-ol)
OCC=CC1=CC=CC=C1
Download
INCHI for NP0137409 (3-Phenyl-2-propen-1-ol)
InChI=1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2
Download
View in JSmol
Synonyms
ValueSource
3-Phenyl-2-propen-1-olChEBI
StyrylcarbinolChEBI
ZimtalcoholChEBI
1-Phenyl-1-propen-3-olHMDB
3-Phenyl-2-propene-1-olHMDB
3-Phenyl-2-propenolHMDB
3-Phenylallyl alcoholHMDB
3-Phenylprop-2-en-1-olHMDB
Cinnamic alcoholHMDB
Cinnamyl alcohol, 8ciHMDB
FEMA 2294HMDB
gamma-Phenylallyl alcoholHMDB
Phenyl-2-propen-1-olHMDB
Phenyl-2-propenolHMDB
Phenylallyl alcoholHMDB
StyroneHMDB
Styryl alcoholHMDB
Cinnamyl alcohol, (e)-isomerHMDB
Cinnamyl alcohol, titanium (4+) saltHMDB
Chemical FormulaC9H10O
Average Mass134.1751 Da
Monoisotopic Mass134.07316 Da
IUPAC Name3-phenylprop-2-en-1-ol
Traditional Name3-phenyl-2-propen-1-ol
CAS Registry NumberNot Available
SMILES
OCC=CC1=CC=CC=C1
InChI Identifier
InChI=1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2
InChI KeyOOCCDEMITAIZTP-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Bidens graveolensLOTUS Database
Cinnamomum aromaticumLOTUS Database
Cinnamomum burmanniLOTUS Database
Cinnamomum sieboldiiLOTUS Database
Cinnamomum verumLOTUS Database
Cinnamomum yabunikkeiLOTUS Database
Citrullus lanatusLOTUS Database
Coreopsis woytkowskiiLOTUS Database
Cryptocarya amygdalinaLOTUS Database
Ficus caricaLOTUS Database
Illicium verumLOTUS Database
Lavandula angustifoliaLOTUS Database
Rhodiola roseaLOTUS Database
Rhodiola sachalinensisLOTUS Database
Syzygium jambosLOTUS Database
Tetrapanax papyriferLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCinnamyl alcohols  
Sub ClassNot Available
Direct ParentCinnamyl alcohols  
Alternative Parents
Substituents
  • Cinnamyl alcohol
    • 

  • Styrene
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary 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
logP1.93ALOGPS
logP1.82ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)15.62ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.19 m³·mol⁻¹ChemAxon
Polarizability15.2 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029697  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000887  
KNApSAcK IDC00042390  
Chemspider ID4444146  
KEGG Compound IDC02394  
BioCyc IDCINNAMYL-ALC  
BiGG IDNot Available
Wikipedia LinkCinnamyl_alcohol  
METLIN IDNot Available
PubChem Compound5280511  
PDB IDNot Available
ChEBI ID17177  
Good Scents IDNot Available
References
General References
  1. Niklasson IB, Delaine T, Islam MN, Karlsson R, Luthman K, Karlberg AT: Cinnamyl alcohol oxidizes rapidly upon air exposure. Contact Dermatitis. 2013 Mar;68(3):129-38. doi: 10.1111/cod.12009. [PubMed:23421457  ] 
  2. Grech-Baran M, Syklowska-Baranek K, Krajewska-Patan A, Wyrwal A, Pietrosiuk A: Biotransformation of cinnamyl alcohol to rosavins by non-transformed wild type and hairy root cultures of Rhodiola kirilowii. Biotechnol Lett. 2014 Mar;36(3):649-56. doi: 10.1007/s10529-013-1401-5. Epub 2013 Nov 5. [PubMed:24190481  ]