NP-MRD: Showing NP-Card for 3',4',5'-Trimethoxycinnamyl alcohol (NP0335245)

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Record Information

Version

2.0

Created at

2024-09-11 00:43:34 UTC

Updated at

2024-09-11 00:43:34 UTC

NP-MRD ID

NP0335245

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3',4',5'-Trimethoxycinnamyl alcohol

Description

3',4',5'-Trimethoxycinnamyl alcohol, also known as 3-(3,4,5-trimethoxyphenyl)-2-propen-1-ol, belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety. 3',4',5'-Trimethoxycinnamyl alcohol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3',4',5'-Trimethoxycinnamyl alcohol has been detected, but not quantified in, herbs and spices. This could make 3',4',5'-trimethoxycinnamyl alcohol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241208362D          

 16 16  0  0  0  0            999 V2000
   -0.3567   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0713   -0.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7848   -1.0308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7848   -1.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4995    0.6185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0714   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3581   -0.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3581    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567    0.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0713    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7848    0.6185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4995    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567    1.4432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3581    1.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  2  0  0  0  0
  2  3  1  0  0  0  0
  2 12  2  0  0  0  0
  3  4  1  0  0  0  0
  5  6  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  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335245

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C/CO)=CC(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C12H16O4/c1-14-10-7-9(5-4-6-13)8-11(15-2)12(10)16-3/h4-5,7-8,13H,6H2,1-3H3/b5-4-

> <INCHI_KEY>
HZDDMDAKGIRCPP-PLNGDYQASA-N

> <FORMULA>
C12H16O4

> <MOLECULAR_WEIGHT>
224.253

> <EXACT_MASS>
224.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
24.044083980971926

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-ol

> <ALOGPS_LOGP>
2.08

> <JCHEM_LOGP>
1.3427979250000002

> <ALOGPS_LOGS>
-2.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.622574789380156

> <JCHEM_PKA_STRONGEST_BASIC>
-2.526485787125119

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
62.58210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.59e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

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      -0.666  -1.924   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.000  -1.155   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.332  -1.924   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -3.332  -3.464   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.666   1.155   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.334   0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.334  -1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.000  -1.924   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.668  -1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.668   0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.666   1.155   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.000   0.385   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.332   1.155   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.666   0.385   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.666   2.694   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.668   3.464   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    6                                                            
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    1    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12    2   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   11   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
3-(3,4,5-Trimethoxyphenyl)-2-propen-1-ol	HMDB

Chemical Formula

C₁₂H₁₆O₄

Average Mass

224.2530 Da

Monoisotopic Mass

224.10486 Da

IUPAC Name

(2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-ol

Traditional Name

(2Z)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-ol

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C/CO)=CC(OC)=C1OC

InChI Identifier

InChI=1S/C12H16O4/c1-14-10-7-9(5-4-6-13)8-11(15-2)12(10)16-3/h4-5,7-8,13H,6H2,1-3H3/b5-4-

InChI Key

HZDDMDAKGIRCPP-PLNGDYQASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamyl alcohols

Sub Class

Not Available

Direct Parent

Cinnamyl alcohols

Alternative Parents

Substituents

Cinnamyl alcohol
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ether
Primary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
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	2.08	ALOGPS
logP	1.34	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	15.62	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	62.58 m³·mol⁻¹	ChemAxon
Polarizability	24.04 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0040890

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020726

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102246983

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3',4',5'-Trimethoxycinnamyl alcohol (NP0335245)

MOL for NP0335245 (3',4',5'-Trimethoxycinnamyl alcohol)

3D MOL for NP0335245 (3',4',5'-Trimethoxycinnamyl alcohol)

3D SDF for NP0335245 (3',4',5'-Trimethoxycinnamyl alcohol)

3D-SDF for NP0335245 (3',4',5'-Trimethoxycinnamyl alcohol)

PDB for NP0335245 (3',4',5'-Trimethoxycinnamyl alcohol)

3D PDB for NP0335245 (3',4',5'-Trimethoxycinnamyl alcohol)

SMILES for NP0335245 (3',4',5'-Trimethoxycinnamyl alcohol)

INCHI for NP0335245 (3',4',5'-Trimethoxycinnamyl alcohol)

Structure for NP0335245 (3',4',5'-Trimethoxycinnamyl alcohol)

3D Structure for NP0335245 (3',4',5'-Trimethoxycinnamyl alcohol)