NP-MRD: Showing NP-Card for Methyl ferulate (NP0002814)

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Record Information

Version

2.0

Created at

2020-11-23 19:41:06 UTC

Updated at

2021-08-19 23:59:26 UTC

NP-MRD ID

NP0002814

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methyl ferulate

Provided By

BMRB

Description

Trans-methylferulate, also known as methyl ferulic acid, belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Trans-methylferulate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Methyl ferulate is found in Actaea racemosa, Aristolochia cucurbitifolia, Aristolochia elegans, Aristolochia foveolata, Aristolochia kaempferi, Aristolochia kankauensis, Artemisia capillaris, Aster indicus, Brucea javanica, Buddleja globosa, Pisonia umbellifera, Cestrum parqui, Citrus medica, Citrus sudachi , Coreopsis grandiflora, Guatteria foliosa, Houttuynia cordata, Humulus japonicus, Iris milesii, Ligularia dentata, Ligularia fischeri, Meum athamanticum, Murraya paniculata, Penstemon whippleanus, Phellodendron chinense, Phyllanthus oligospermus, Pinus massoniana, Pisonia aculeata, Rhus semialata , Sabia japonica, Severinia buxifolia , Spiraea formosana , Stemona japonica, Stereospermum acuminatissimum, Tamarix aphylla, Taraxacum mongolicum, Tetragonia tetragonoides and Zanthoxylum wutaiense. Based on a literature review very few articles have been published on trans-methylferulate.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 27 27  0  0  0  0  0  0  0  0999 V2000
    5.6443    0.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1553    0.8026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2537   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8412   -1.7765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7647   -0.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8632   -1.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6258   -1.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5274   -2.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0164   -2.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6038   -0.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0928   -0.6884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7023    0.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2897    1.7093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3882    2.9081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2133    0.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8256    2.1102    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4629   -0.8678    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1333    0.4399    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1773    1.1653    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4506   -2.7939    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9399   -3.8114    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9179   -3.4487    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6802    0.6918    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5870    3.8097    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1893    2.0066    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4866    4.1070    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3117    1.3466    0.0000 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15  7  1  0
  1 16  1  6
  1 17  1  0
  1 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
  9 22  1  0
 11 23  1  0
 14 24  1  6
 14 25  1  0
 14 26  1  0
 15 27  1  0
M  END
> <DATABASE_ID>
NP0002814

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\C=C\C1=CC(OC)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O4/c1-14-10-7-8(3-5-9(10)12)4-6-11(13)15-2/h3-7,12H,1-2H3/b6-4+

> <INCHI_KEY>
AUJXJFHANFIVKH-GQCTYLIASA-N

> <FORMULA>
C11H12O4

> <MOLECULAR_WEIGHT>
208.213

> <EXACT_MASS>
208.073558866

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.533366242815294

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
2.054077062

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.86784918730006

> <JCHEM_PKA_STRONGEST_BASIC>
-4.888620088905742

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
56.27310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-NOV-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-NOV-20         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -6.930   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       1.334  -2.310   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  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   15                                                            
CONECT    3    5    8                                                       
CONECT    4    6    8                                                       
CONECT    5    3    9                                                       
CONECT    6    4   11                                                       
CONECT    7    8   10                                                       
CONECT    8    3    4    7                                                  
CONECT    9    5   10   12                                                  
CONECT   10    7    9   14                                                  
CONECT   11    6   13   15                                                  
CONECT   12    9                                                            
CONECT   13   11                                                            
CONECT   14    1   10                                                       
CONECT   15    2   11                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    NP0002814
HETATM    1  C1  UNL     1       5.679   0.661   0.358  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.495  -0.086   0.342  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.285   0.563   0.196  1.00  0.00           C  
HETATM    4  O2  UNL     1       3.283   1.809   0.081  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.035  -0.193   0.176  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.871   0.416   0.037  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.421  -0.243   0.005  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.574  -1.596   0.118  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.832  -2.196   0.084  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.937  -1.397  -0.069  1.00  0.00           C  
HETATM   11  O3  UNL     1      -4.205  -1.931  -0.111  1.00  0.00           O  
HETATM   12  C9  UNL     1      -2.837  -0.016  -0.189  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.967   0.777  -0.343  1.00  0.00           O  
HETATM   14  C10 UNL     1      -3.807   2.174  -0.460  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.565   0.517  -0.147  1.00  0.00           C  
HETATM   16  H1  UNL     1       6.518  -0.023   0.634  1.00  0.00           H  
HETATM   17  H2  UNL     1       5.672   1.439   1.176  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.911   1.145  -0.602  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.026  -1.267   0.274  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.908   1.502  -0.061  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.285  -2.241   0.239  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.879  -3.266   0.179  1.00  0.00           H  
HETATM   23  H8  UNL     1      -4.316  -2.928  -0.027  1.00  0.00           H  
HETATM   24  H9  UNL     1      -4.733   2.671  -0.815  1.00  0.00           H  
HETATM   25  H10 UNL     1      -3.050   2.331  -1.283  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.391   2.636   0.448  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.455   1.606  -0.239  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   19
CONECT    6    7   20
CONECT    7    8    8   15
CONECT    8    9   21
CONECT    9   10   10   22
CONECT   10   11   12
CONECT   11   23
CONECT   12   13   15   15
CONECT   13   14
CONECT   14   24   25   26
CONECT   15   27
END

View in JSmol

Synonyms

Value	Source
3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid methyl ester	ChEBI
4-Hydroxy-3-methoxy-cinnamic acid methyl ester	ChEBI
Methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)acrylate	ChEBI
Methyl ferulate	ChEBI
3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate methyl ester	Generator
4-Hydroxy-3-methoxy-cinnamate methyl ester	Generator
Methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid	Generator
Methyl ferulic acid	Generator
trans-Methylferulic acid	Generator

Chemical Formula

C₁₁H₁₂O₄

Average Mass

208.2130 Da

Monoisotopic Mass

208.07356 Da

IUPAC Name

methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Traditional Name

methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)\C=C\C1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C11H12O4/c1-14-10-7-8(3-5-9(10)12)4-6-11(13)15-2/h3-7,12H,1-2H3/b6-4+

InChI Key

AUJXJFHANFIVKH-GQCTYLIASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Actaea racemosa	LOTUS Database	35616633
Allium cepa	FooDB	KNAPSACK
Aristolochia cucurbitifolia	LOTUS Database	35616633
Aristolochia elegans	LOTUS Database	35616633
Aristolochia foveolata	LOTUS Database	35616633
Aristolochia kaempferi	LOTUS Database	35616633
Aristolochia kankauensis	LOTUS Database	35616633
Artemisia capillaris	LOTUS Database	35616633
Aster indicus	LOTUS Database	35616633
Atalantia buxifolia	KNApSAcK Database	22123792
Brucea javanica	LOTUS Database	35616633
Buddleja globosa	LOTUS Database	35616633
Ceodes umbellifera	LOTUS Database	35616633
Cestrum parqui	LOTUS Database	35616633
Citrus medica	LOTUS Database	35616633
Citrus sudachi	Plant	KNApSAcK
Coreopsis grandiflora	LOTUS Database	35616633
Guatteria foliosa	LOTUS Database	35616633
Hibiscus taiwanensis	KNApSAcK Database	22123792
Houttuynia cordata	LOTUS Database	35616633
Humulus japonicus	LOTUS Database	35616633
Iris milesii	LOTUS Database	35616633
Ligularia dentata	LOTUS Database	35616633
Ligularia dentata Hara	KNApSAcK Database	22123792
Ligularia fischeri	LOTUS Database	35616633
Meum athamanticum	LOTUS Database	35616633
Murraya paniculata	LOTUS Database	35616633
Palicourea coriacea	KNApSAcK Database	22123792
Penstemon whippleanus	LOTUS Database	35616633
Phellodendron amurense var.wilsonii	KNApSAcK Database	22123792
Phellodendron chinense	LOTUS Database	35616633
Phyllanthus oligospermus	Plant	KNApSAcK
Pinus massoniana	LOTUS Database	35616633
Pisonia aculeata	LOTUS Database	35616633
Rhus semialata	Plant	KNApSAcK
Sabia japonica	LOTUS Database	35616633
Severinia buxifolia	Plant	KNApSAcK
Spiraea formosana	Plant	KNApSAcK
Stemona japonica	LOTUS Database	35616633
Stereospermum acuminatissimum	LOTUS Database	35616633
Tamarix aphylla	LOTUS Database	35616633
Taraxacum formosanum	KNApSAcK Database	22123792
Taraxacum mongolicum	LOTUS Database	35616633
Tetragonia tetragonioides	LOTUS Database	35616633
Zanthoxylum wutaiense	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Methoxyphenol
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:67379 )
cinnamate ester (CHEBI:67379 )
methyl ester (CHEBI:67379 )
monomethoxybenzene (CHEBI:67379 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	338.00 to 339.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1398 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.209 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	2.05	ChemAxon
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	56.27 m³·mol⁻¹	ChemAxon
Polarizability	21.53 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00029337

Chemspider ID

4512663

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

67379

Good Scents ID

rw1394591

References

General References

Showing NP-Card for Methyl ferulate (NP0002814)

MOL for NP0002814 (Methyl ferulate)

3D MOL for NP0002814 (Methyl ferulate)

3D SDF for NP0002814 (Methyl ferulate)

3D-SDF for NP0002814 (Methyl ferulate)

PDB for NP0002814 (Methyl ferulate)

3D PDB for NP0002814 (Methyl ferulate)

SMILES for NP0002814 (Methyl ferulate)

INCHI for NP0002814 (Methyl ferulate)

Structure for NP0002814 (Methyl ferulate)

3D Structure for NP0002814 (Methyl ferulate)