NP-MRD: Showing NP-Card for Dihydroferulic acid (NP0077580)

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Record Information

Version

2.0

Created at

2022-04-28 22:42:31 UTC

Updated at

2025-02-11 15:43:43 UTC

NP-MRD ID

NP0077580

Natural Product DOI

https://doi.org/10.57994/1438

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihydroferulic acid

Description

Dihydroferulic acid, also known as dihydroconiferylate or DHFA, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. A monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 3 has been replaced by a 4-hydroxy-3-methoxyphenyl group. Dihydroferulic acid is found in Ailanthus altissima, Bulbophyllum vaginatum, Colchicum kotschyi, Curcuma domestica , Dianthus superbus, Melicope semecarpifolia, Picea glauca, Pseudostellaria heterophylla, Stellaria dichotoma and Zingiber officinale. Dihydroferulic acid was first documented in 2001 (PMID: 11368919). Dihydroferulic acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 11693915) (PMID: 17469871) (PMID: 19157126) (PMID: 21676405).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272007472D          

 14 14  0  0  0  0            999 V2000
10017.751910017.8102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10020.611110019.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.325110019.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.041210019.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.755310019.0478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10022.041210020.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10019.896910019.0476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.182510019.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.467910019.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.467910018.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.182310017.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.896910018.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.182210016.9835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10019.898110016.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12  7  1  0  0  0  0
  1 10  1  0  0  0  0
  7  2  1  0  0  0  0
  2  3  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077580

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CCC(O)=O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2,4,6,11H,3,5H2,1H3,(H,12,13)

> <INCHI_KEY>
BOLQJTPHPSDZHR-UHFFFAOYSA-N

> <FORMULA>
C10H12O4

> <MOLECULAR_WEIGHT>
196.1999

> <EXACT_MASS>
196.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.802083951346205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-hydroxy-3-methoxyphenyl)propanoic acid

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
1.5943261829999997

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.946560494761734

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9524008986487043

> <JCHEM_PKA_STRONGEST_BASIC>
-4.892121858205717

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
50.410700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
homovanillinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8699.8038699.912   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8705.1418702.993   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8706.4738702.223   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8707.8108702.993   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8709.1438702.223   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8707.8108704.534   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8703.8088702.222   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8702.4748702.992   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8701.1408702.222   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8701.1408700.682   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8702.4748699.912   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8703.8088700.682   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8702.4748698.369   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8703.8108697.598   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2    7    3                                                       
CONECT    3    4    2                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    8   12    2                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11    1                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
3-(4-Hydroxy-3-methoxyphenyl)propionic acid	ChEBI
Dihydroconiferylic acid	ChEBI
3-(4-Hydroxy-3-methoxyphenyl)propionate	Generator
Dihydroconiferylate	Generator
Dihydroferulate	Generator
Hydroferulate	HMDB
(4-Hydroxy-3-methoxyphenyl)propionic acid	HMDB
3-(3'-Methoxy-4'-hydroxyphenyl)propionic acid	HMDB
3-(3-Methoxy-4-hydroxyphenyl)propanoic acid	HMDB
3-(3-Methoxy-4-hydroxyphenyl)propionic acid	HMDB
3-(3’-methoxy-4’-hydroxyphenyl)propionic acid	HMDB
3-(4-Hydroxy-3-methoxyphenyl)propanoic acid	HMDB
3-Methoxy-4-hydroxyphenylpropionic acid	HMDB
3-Methoxyphloretic acid	HMDB
4-Hydroxy-3-methoxybenzenepropanoic acid	HMDB
DHFA	HMDB
Hydroferulic acid	HMDB
Shorbic acid	HMDB
beta-(4-Hydroxy-3-methoxyphenyl)propionic acid	HMDB
beta-3-Methoxy-4-hydroxyphenylpropionic acid	HMDB
Β-(4-hydroxy-3-methoxyphenyl)propionic acid	HMDB
Β-3-methoxy-4-hydroxyphenylpropionic acid	HMDB
Dihydroferulic acid	HMDB
3-(4'-Hydroxy-3'-methoxyphenyl)propanoic acid
3-(4-Hydroxy-3-methoxyphenyl)dihydrocinnamic acid
4-Hydroxy-3-methoxyhydrocinnamic acid	PhytoBank
4-Hydroxy-3-methoxybenzenepropionic acid	PhytoBank
(4-Hydroxy-3-methoxyphenyl)propanoic acid	PhytoBank
3-(3'-Methoxy-4'-hydroxyphenyl)propanoic acid	PhytoBank
3-(3’-Methoxy-4’-hydroxyphenyl)propanoic acid	PhytoBank
3-Methoxy-4-hydroxyphenylpropanoic acid	PhytoBank
alpha,beta-Dihydroferulic acid	PhytoBank
α,β-Dihydroferulic acid	PhytoBank
beta-(4-Hydroxy-3-methoxyphenyl)propanoic acid	PhytoBank
β-(4-Hydroxy-3-methoxyphenyl)propanoic acid	PhytoBank
beta-3-Methoxy-4-hydroxyphenylpropanoic acid	PhytoBank
β-3-Methoxy-4-hydroxyphenylpropanoic acid	PhytoBank

Chemical Formula

C₁₀H₁₂O₄

Average Mass

196.1999 Da

Monoisotopic Mass

196.07356 Da

IUPAC Name

3-(4-hydroxy-3-methoxyphenyl)propanoic acid

Traditional Name

homovanillinic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(CCC(O)=O)=CC=C1O

InChI Identifier

InChI=1S/C10H12O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2,4,6,11H,3,5H2,1H3,(H,12,13)

InChI Key

BOLQJTPHPSDZHR-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	[email protected]	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-02	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	[email protected]	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-02	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	[email protected]	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-02	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	[email protected]	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-02	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	[email protected]	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-02	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	[email protected]	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-02	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Ailanthus altissima	LOTUS Database	35616633
Bulbophyllum vaginatum	Plant	KNApSAcK
Colchicum kotschyi	LOTUS Database	35616633
Curcuma longa	Plant	KNApSAcK
Dianthus superbus	LOTUS Database	35616633
Melicope semecarpifolia	LOTUS Database	35616633
Picea glauca	LOTUS Database	35616633
Pseudostellaria heterophylla	LOTUS Database	35616633
Stellaria dichotoma	LOTUS Database	35616633
Zingiber officinale	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:86612 )

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	1.03	ALOGPS
logP	1.59	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.95	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	50.41 m³·mol⁻¹	ChemAxon
Polarizability	19.8 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

HMDB0062121

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029987

KNApSAcK ID

C00040946

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

14340

PDB ID

Not Available

ChEBI ID

86612

Good Scents ID

Not Available

References

General References

Rechner AR, Spencer JP, Kuhnle G, Hahn U, Rice-Evans CA: Novel biomarkers of the metabolism of caffeic acid derivatives in vivo. Free Radic Biol Med. 2001 Jun 1;30(11):1213-22. [PubMed:11368919 ]
Larsson S, Nilvebrant NO, Jonsson LJ: Effect of overexpression of Saccharomyces cerevisiae Pad1p on the resistance to phenylacrylic acids and lignocellulose hydrolysates under aerobic and oxygen-limited conditions. Appl Microbiol Biotechnol. 2001 Oct;57(1-2):167-74. doi: 10.1007/s002530100742. [PubMed:11693915 ]
Beck JJ, Kim JH, Campbell BC, Chou SC: Fungicidal activities of dihydroferulic acid alkyl ester analogues. J Nat Prod. 2007 May;70(5):779-82. doi: 10.1021/np0606345. Epub 2007 May 1. [PubMed:17469871 ]
Li Y, Yang XW: [Studies on chemical constituents of root tuber of cultivated Pseudostellaria heterophylla (Zheshen No. 1)]. Zhongguo Zhong Yao Za Zhi. 2008 Oct;33(20):2353-5. [PubMed:19157126 ]
Redeuil K, Smarrito-Menozzi C, Guy P, Rezzi S, Dionisi F, Williamson G, Nagy K, Renouf M: Identification of novel circulating coffee metabolites in human plasma by liquid chromatography-mass spectrometry. J Chromatogr A. 2011 Jul 22;1218(29):4678-88. doi: 10.1016/j.chroma.2011.05.050. Epub 2011 May 26. [PubMed:21676405 ]

Showing NP-Card for Dihydroferulic acid (NP0077580)

MOL for NP0077580 (Dihydroferulic acid)

3D MOL for NP0077580 (Dihydroferulic acid)

3D SDF for NP0077580 (Dihydroferulic acid)

3D-SDF for NP0077580 (Dihydroferulic acid)

PDB for NP0077580 (Dihydroferulic acid)

3D PDB for NP0077580 (Dihydroferulic acid)

SMILES for NP0077580 (Dihydroferulic acid)

INCHI for NP0077580 (Dihydroferulic acid)

Structure for NP0077580 (Dihydroferulic acid)

3D Structure for NP0077580 (Dihydroferulic acid)