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Showing NP-Card for Chavicol (NP0047854)

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Record Information
Version2.0
Created at2022-03-17 20:47:02 UTC
Updated at2022-03-17 20:47:03 UTC
NP-MRD IDNP0047854
Secondary Accession NumbersNone
Natural Product Identification
Common NameChavicol
DescriptionChavicol, also known as p-allylphenol or alpha -propylene, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. Chavicol is an extremely weak basic (essentially neutral) compound (based on its pKa). Chavicol is a medicinal and phenolic tasting compound. Outside of the human body, Chavicol is found, on average, in the highest concentration within a few different foods, such as cloves, sweet marjorams, and sweet basils and in a lower concentration in pineapples. Chavicol has also been detected, but not quantified in, several different foods, such as allspices, chinese cinnamons, fats and oils, and gingers. This could make chavicol a potential biomarker for the consumption of these foods. Chavicol is found in Agastache rugosa, Alnus pendula, Alpinia conchigera, Alpinia galanga, Cinnamomum burmannii, Cyperus conglomeratus, Illicium difengpi, Jackiella javanica, Magnolia garrettii, Magnolia obovata, Mandragora officinarum, Nicotiana bonariensis, Ocimum sanctum , Osmorhiza aristata, Pimenta racemosa, Pinus contorta, Piper betle , Solidago odora, Tagetes lucida, Viburnum furcatum and Viburnum japonicum. A phenylpropanoid that is phenol substituted by a prop-2-enyl group at position 4.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047854 (Chavicol)


  Mrv1652305291811322D          

 10 10  0  0  0  0            999 V2000
    0.5000    1.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2145    1.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000   -0.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2145    0.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2145    0.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9289   -0.1063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2145    1.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9289    1.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6434    1.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3579    1.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  2  0  0  0  0
  2  5  2  0  0  0  0
  5  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
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3D MOL for NP0047854 (Chavicol)

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3D SDF for NP0047854 (Chavicol)

  Mrv1652305291811322D          

 10 10  0  0  0  0            999 V2000
    0.5000    1.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2145    1.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000   -0.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2145    0.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2145    0.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9289   -0.1063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2145    1.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9289    1.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6434    1.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3579    1.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  2  0  0  0  0
  2  5  2  0  0  0  0
  5  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047854

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(CC=C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7,10H,1,3H2

> <INCHI_KEY>
RGIBXDHONMXTLI-UHFFFAOYSA-N

> <FORMULA>
C9H10O

> <MOLECULAR_WEIGHT>
134.1751

> <EXACT_MASS>
134.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.951158099886104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(prop-2-en-1-yl)phenol

> <ALOGPS_LOGP>
2.46

> <JCHEM_LOGP>
2.768251227333333

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.50147367907245

> <JCHEM_PKA_STRONGEST_BASIC>
-5.958425173561264

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
42.3262

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.46e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chavicol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047854 (Chavicol)
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PDB for NP0047854 (Chavicol)
HEADER    PROTEIN                                 29-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-MAY-18         0                                  
HETATM    1  C   UNK     0       0.933   2.882   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.400   2.112   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.933  -0.198   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.267   0.572   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.400   0.572   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.734  -0.198   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.267   2.112   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.601   2.882   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.934   2.112   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.268   2.882   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    5                                                       
CONECT    3    5    4                                                       
CONECT    4    3    7                                                       
CONECT    5    2    3    6                                                  
CONECT    6    5                                                            
CONECT    7    1    4    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0047854 (Chavicol)
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SMILES for NP0047854 (Chavicol)
OC1=CC=C(CC=C)C=C1
Download
INCHI for NP0047854 (Chavicol)
InChI=1S/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7,10H,1,3H2
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Synonyms
ValueSource
4-(2-Propenyl)phenolChEBI
4-(Prop-2-enyl)-phenolChEBI
4-AllylphenolChEBI
gamma-(p-Hydroxyphenyl)-alpha-propyleneChEBI
p-AllylphenolChEBI
p-ChavicolChEBI
p-HydroxyallylbenzeneChEBI
g-(p-Hydroxyphenyl)-a-propyleneGenerator
Γ-(p-hydroxyphenyl)-α-propyleneGenerator
3-(p-Hydroxyphenyl)-1-propeneHMDB
4-(2-Propenyl)-phenolHMDB
alpha -PropyleneHMDB
Laquo gammaraquo -(p-hydroxyphenyl)-alpha -propyleneHMDB
p-Allyl-phenolHMDB
p-HydroxyallylpropeneHMDB
Phenol, 4-(2-propenyl)- (9ci)HMDB
Phenol, p-allyl- (8ci)HMDB
Chemical FormulaC9H10O
Average Mass134.1751 Da
Monoisotopic Mass134.07316 Da
IUPAC Name4-(prop-2-en-1-yl)phenol
Traditional Namechavicol
CAS Registry Number501-92-8
SMILES
OC1=CC=C(CC=C)C=C1
InChI Identifier
InChI=1S/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7,10H,1,3H2
InChI KeyRGIBXDHONMXTLI-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agastache rugosaLOTUS Database
Alnus pendulaLOTUS Database
Alpinia conchigeraLOTUS Database
Alpinia galangaLOTUS Database
Ananas comosusFooDB
Cinnamomum aromaticumFooDB
Cinnamomum burmanniLOTUS Database
Cyperus conglomeratusLOTUS Database
Illicium difengpiLOTUS Database
Jackiella javanica-
Magnolia garrettiiLOTUS Database
Magnolia obovataLOTUS Database
Mandragora officinarumLOTUS Database
Nicotiana bonariensisPlant
Ocimum basilicumFooDB
Ocimum tenuiflorumPlant
Origanum majoranaFooDB
Osmorhiza aristataLOTUS Database
Pimenta dioicaFooDB
Pimenta racemosaLOTUS Database
Pinus contortaLOTUS Database
Piper betlePlant
Solidago odoraLOTUS Database
Syzygium aromaticumFooDB
Tagetes lucidaLOTUS Database
Viburnum furcatumLOTUS Database
Viburnum japonicumLOTUS Database
Zingiber officinaleFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenols  
Sub Class1-hydroxy-2-unsubstituted benzenoids  
Direct Parent1-hydroxy-2-unsubstituted benzenoids  
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • 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
logP2.46ALOGPS
logP2.77ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.33 m³·mol⁻¹ChemAxon
Polarizability14.95 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034107  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012373  
KNApSAcK IDC00000621  
Chemspider ID21105856  
KEGG Compound IDC16930  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChavicol  
METLIN IDNot Available
PubChem Compound68148  
PDB IDNot Available
ChEBI ID50158  
Good Scents IDNot Available
References
General ReferencesNot Available