NP-MRD: Showing NP-Card for (2e)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal (NP0214453)

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Record Information

Version

2.0

Created at

2022-09-05 13:45:20 UTC

Updated at

2022-09-05 13:45:20 UTC

NP-MRD ID

NP0214453

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal

Description

3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal, also known as 4-hydroxy-3-prenylcinnamaldehyde, belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal. 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal has been detected, but not quantified in, citrus. (2e)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal is found in Boronia pinnata. This could make 3-[4-hydroxy-3-(3-methyl-2-butenyl)phenyl]-2-propenal a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.9412   -0.9209    0.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1953    0.2745    0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9994    1.5512    0.7336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9146    0.3100    1.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -0.8400    1.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1275   -0.5949    0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3783   -0.2542    0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4005   -0.0345   -0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7511    0.3267    0.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1343    0.4826    1.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5240    0.8501    1.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3836    1.0265    0.7722 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1371   -0.1644   -1.7057 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8993   -0.5025   -2.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1338   -0.7241   -1.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010   -1.0670   -1.7435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2911   -0.7533   -0.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4057   -1.8651    0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8525   -1.0589    0.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7089    1.6208   -0.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3049    2.3903    0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5336    1.5040    1.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4651    1.2719    1.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4465   -1.8125    0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5628   -0.9102    2.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5329   -0.1660    1.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5301    0.4884   -0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    0.3391    2.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8009    0.9688    2.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9598    0.0121   -2.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7300   -0.5960   -3.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560   -1.1526   -2.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6 15  2  0
 15 16  1  0
 15 14  1  0
 14 13  2  0
 13  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  8  7  2  0
  7  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
 16 32  1  0
 14 31  1  0
 13 30  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
  7 26  1  0
M  END


  Mrv0541 05061312092D          

 16 16  0  0  0  0            999 V2000
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
   -0.7145    2.0625    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
   -0.7145    1.2375    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
    1.4289   -2.4750    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    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
    0.0000    0.8250    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
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  3  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  5  2  0  0  0  0
 12  4  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  2  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  2  0  0  0  0
 15  9  2  0  0  0  0
 16 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0214453

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C=CC(\C=C\C=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O2/c1-11(2)5-7-13-10-12(4-3-9-15)6-8-14(13)16/h3-6,8-10,16H,7H2,1-2H3/b4-3+

> <INCHI_KEY>
FNDJBOATFIWAJR-ONEGZZNKSA-N

> <FORMULA>
C14H16O2

> <MOLECULAR_WEIGHT>
216.2756

> <EXACT_MASS>
216.115029756

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.848800406390694

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
3.4024716853333334

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.849162083924986

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3466227847943095

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
68.3582

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal

> <JCHEM_VEBER_RULE>
1

$$$$

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      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3    4    9                                                       
CONECT    4    3   12                                                       
CONECT    5    7   11                                                       
CONECT    6    8   12                                                       
CONECT    7    5   13                                                       
CONECT    8    6   14                                                       
CONECT    9    3   15                                                       
CONECT   10   12   13                                                       
CONECT   11    1    2    5                                                  
CONECT   12    4    6   10                                                  
CONECT   13    7   10   14                                                  
CONECT   14    8   13   16                                                  
CONECT   15    9                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-3-prenylcinnamaldehyde	HMDB
3-(4-Hydroxy-3-(3-methyl-2-butenyl)phenyl)-2-propenal	HMDB
3-HMBP-2-Propenal	MeSH

Chemical Formula

C₁₄H₁₆O₂

Average Mass

216.2756 Da

Monoisotopic Mass

216.11503 Da

IUPAC Name

(2E)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal

Traditional Name

(2E)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C=CC(\C=C\C=O)=C1

InChI Identifier

InChI=1S/C14H16O2/c1-11(2)5-7-13-10-12(4-3-9-15)6-8-14(13)16/h3-6,8-10,16H,7H2,1-2H3/b4-3+

InChI Key

FNDJBOATFIWAJR-ONEGZZNKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Boronia pinnata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamaldehydes

Sub Class

Not Available

Direct Parent

Cinnamaldehydes

Alternative Parents

Substituents

Cinnamaldehyde
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.55	ALOGPS
logP	3.4	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.85	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.36 m³·mol⁻¹	ChemAxon
Polarizability	24.85 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0040833

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020655

KNApSAcK ID

Not Available

Chemspider ID

4947663

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6443694

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal (NP0214453)

MOL for NP0214453 ((2e)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal)

3D MOL for NP0214453 ((2e)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal)

3D SDF for NP0214453 ((2e)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal)

3D-SDF for NP0214453 ((2e)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal)

PDB for NP0214453 ((2e)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal)

3D PDB for NP0214453 ((2e)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal)

SMILES for NP0214453 ((2e)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal)

INCHI for NP0214453 ((2e)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal)

Structure for NP0214453 ((2e)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal)

3D Structure for NP0214453 ((2e)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enal)