NP-MRD: Showing NP-Card for 4-Hydroxy-3-methoxycinnamaldehyde (NP0002734)

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Record Information

Version

2.0

Created at

2020-11-23 19:39:06 UTC

Updated at

2024-09-03 04:16:32 UTC

NP-MRD ID

NP0002734

Natural Product DOI

https://doi.org/10.57994/0700

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Hydroxy-3-methoxycinnamaldehyde

Provided By

BMRB

Description

Coniferaldehyde belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Coniferaldehyde is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 4-Hydroxy-3-methoxycinnamaldehyde was first documented in 2012 (PMID: 22466741). Based on a literature review very few articles have been published on Coniferaldehyde (PMID: 22034160).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    2.0370   -2.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6179   -1.2056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7106   -0.0111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2225   -0.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6848    0.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1729    0.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7537   -0.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2418   -0.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1491    0.4295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1040    2.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3842    2.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2914    1.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7795    1.5604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4200   -3.1694    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6541   -2.0077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4562   -3.9715    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583   -1.5825    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0802    2.0010    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8465   -1.7710    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8227   -2.1479    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0112    3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9650    3.9494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6868    0.3659    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
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  5 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12  3  1  0
  1 14  1  6
  1 15  1  0
  1 16  1  0
  4 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
 10 21  1  0
 11 22  1  0
 13 23  1  0
M  END
> <DATABASE_ID>
NP0002734

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C([H])=O)C([H])=C1OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h2-7,12H,1H3/b3-2+

> <INCHI_KEY>
DKZBBWMURDFHNE-NSCUHMNNSA-N

> <FORMULA>
C10H10O3

> <MOLECULAR_WEIGHT>
178.1846

> <EXACT_MASS>
178.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.379866786522083

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
1.5162334203333336

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.515601076850212

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2891797272383405

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
50.57860000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.47e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
coniferaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.207  -2.054   0.832  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.615  -0.823   0.253  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.634   0.092  -0.119  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.275  -0.186   0.069  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.715   0.704  -0.292  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.139   0.431  -0.104  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.623  -0.673   0.421  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.086  -0.801   0.545  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.529  -1.873   1.053  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.279   1.895  -0.854  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.049   2.204  -1.054  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.014   1.292  -0.683  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.356   1.603  -0.885  0.00  0.00           O+0
HETATM   14  H   UNK     0      -3.104  -2.658   1.093  0.00  0.00           H+0
HETATM   15  H   UNK     0      -1.694  -1.835   1.790  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.570  -2.653   0.160  0.00  0.00           H+0
HETATM   17  H   UNK     0      -0.030  -1.122   0.506  0.00  0.00           H+0
HETATM   18  H   UNK     0       2.836   1.215  -0.430  0.00  0.00           H+0
HETATM   19  H   UNK     0       1.951  -1.429   0.735  0.00  0.00           H+0
HETATM   20  H   UNK     0       4.743  -0.013   0.216  0.00  0.00           H+0
HETATM   21  H   UNK     0       1.050   2.621  -1.150  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.345   3.149  -1.498  0.00  0.00           H+0
HETATM   23  H   UNK     0      -4.059   0.915  -0.603  0.00  0.00           H+0
CONECT    1    2   14   15   16                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8                                                            
CONECT   10    5   11   21                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11   13    3                                                  
CONECT   13   12   23                                                       
CONECT   14    1                                                            
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17    4                                                            
CONECT   18    6                                                            
CONECT   19    7                                                            
CONECT   20    8                                                            
CONECT   21   10                                                            
CONECT   22   11                                                            
CONECT   23   13                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Value	Source
(e)-Coniferaldehyde	ChEBI
4-Hydroxy-3-methoxycinnamaldehyde	ChEBI
Ferulaldehyde	ChEBI
Coniferaldehyde	ChEBI
trans-Coniferyl aldehyde	ChEBI, MeSH, HMDB
Coniferyl aldehyde	MeSH, HMDB
4-HM-CA	MeSH, HMDB
Coniferaldehyde, (e)-isomer	MeSH, HMDB
Coniferylaldehyde	MeSH, HMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenal	HMDB
(2E)-4-Hydroxy-3-methoxycinnamaldehyde	HMDB
(E)-3-(4-Hydroxy-3-methoxyphenyl)acrylaldehyde	HMDB
(E)-3-(4-Hydroxy-m-methoxyphenyl)prop-2-enal	HMDB
(E)-Coniferyl aldehyde	HMDB
(E)-Ferulaldehyde	HMDB
2-Methoxy-4-(3-oxo-1-propenyl)phenol	HMDB
3-(4-Hydroxy-3-methoxyphenyl)-2-propenal	HMDB
3-(4-Hydroxy-3-methoxyphenyl)acrolein	HMDB
3-(4-Hydroxy-3-methoxyphenyl)propenal	HMDB
3-Methoxy-4-hydroxycinnamaldehyde	HMDB
4-Hydroxy-3-methoxy-trans-cinnamaldehyde	HMDB
4-Hydroxy-3-methoxyzimtaldehyde	HMDB
E-Coniferyl aldehyde	HMDB
Ferulic aldehyde	HMDB
Ferulyl aldehyde	HMDB
p-Coniferaldehyde	HMDB
trans-Coniferaldehyde	HMDB
trans-Ferulaldehyde	HMDB

Chemical Formula

C₁₀H₁₀O₃

Average Mass

178.1846 Da

Monoisotopic Mass

178.06299 Da

IUPAC Name

(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enal

Traditional Name

coniferaldehyde

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(\C=C\C=O)=C1

InChI Identifier

InChI=1S/C10H10O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h2-7,12H,1H3/b3-2+

InChI Key

DKZBBWMURDFHNE-NSCUHMNNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	jtkp6n@mail.missouri.edu	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	jtkp6n@mail.missouri.edu	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Not Available	Not Available	2023-06-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Not Available	Not Available	2023-06-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
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

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

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

Methoxyphenols

Direct Parent

Methoxyphenols

Alternative Parents

Not Available

Substituents

Not Available

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	2.22	ALOGPS
logP	1.52	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	9.52	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	50.58 m³·mol⁻¹	ChemAxon
Polarizability	18.38 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

HMDB0141782

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Coniferyl_aldehyde

METLIN ID

Not Available

PubChem Compound

PDB ID

ChEBI ID

Good Scents ID

References

General References

Shreaz S, Bhatia R, Khan N, Muralidhar S, Manzoor N, Khan LA: Influences of cinnamic aldehydes on H(+) extrusion activity and ultrastructure of Candida. J Med Microbiol. 2013 Feb;62(Pt 2):232-240. doi: 10.1099/jmm.0.036145-0. Epub 2011 Oct 27. [PubMed:22034160 ]
Devkota HP, Watanabe M, Watanabe T, Yahara S: Phenolic compounds from the aerial parts of Diplomorpha canescens. Chem Pharm Bull (Tokyo). 2012;60(4):554-6. doi: 10.1248/cpb.60.554. [PubMed:22466741 ]

Showing NP-Card for 4-Hydroxy-3-methoxycinnamaldehyde (NP0002734)

MOL for NP0002734 (4-Hydroxy-3-methoxycinnamaldehyde)

3D MOL for NP0002734 (4-Hydroxy-3-methoxycinnamaldehyde)

3D SDF for NP0002734 (4-Hydroxy-3-methoxycinnamaldehyde)

3D-SDF for NP0002734 (4-Hydroxy-3-methoxycinnamaldehyde)

PDB for NP0002734 (4-Hydroxy-3-methoxycinnamaldehyde)

3D PDB for NP0002734 (4-Hydroxy-3-methoxycinnamaldehyde)

SMILES for NP0002734 (4-Hydroxy-3-methoxycinnamaldehyde)

INCHI for NP0002734 (4-Hydroxy-3-methoxycinnamaldehyde)

Structure for NP0002734 (4-Hydroxy-3-methoxycinnamaldehyde)

3D Structure for NP0002734 (4-Hydroxy-3-methoxycinnamaldehyde)