NP-MRD: Showing NP-Card for 3,4-Dihydroxycinnamaldehyde (NP0054993)

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Record Information

Version

2.0

Created at

2022-04-28 01:10:28 UTC

Updated at

2022-04-28 01:10:28 UTC

NP-MRD ID

NP0054993

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4-Dihydroxycinnamaldehyde

Description

(2E)-3-(3,4-dihydroxyphenyl)prop-2-enal, also known as caffeyl aldehyde or (e)-3,4-dihydroxycinnamaldehyde, 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 (2E)-3-(3,4-dihydroxyphenyl)prop-2-enal is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,4-Dihydroxycinnamaldehyde is found in Apis cerana, Arabidopsis thaliana, Carica papaya , Daphnia pulex, Ilex paraguariensis , Petasites tricholobus , Populus trichocarpa and Tachigali paniculata. 3,4-Dihydroxycinnamaldehyde was first documented in 2002 (PMID: 12423886). A cinnamaldehyde that is (E)-cinnamaldehyde substituted at positions 3 and 4 on the phenyl ring by hydroxy groups (PMID: 20876124).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652308231922102D          

 14 14  0  0  0  0            999 V2000
    0.0000   -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
    1.4289    0.0000    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
    0.0000   -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
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  3  2  0  0  0  0
  5  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  3  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  5  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  1  1  0  0  0  0
 14  2  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054993

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(C=O)=C(\[H])C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O3/c10-5-1-2-7-3-4-8(11)9(12)6-7/h1-6,11-12H/b2-1+

> <INCHI_KEY>
AXMVYSVVTMKQSL-OWOJBTEDSA-N

> <FORMULA>
C9H8O3

> <MOLECULAR_WEIGHT>
164.16

> <EXACT_MASS>
164.047344118

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.367278108474228

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enal

> <ALOGPS_LOGP>
1.71

> <JCHEM_LOGP>
1.3703393643333333

> <ALOGPS_LOGS>
-1.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.470391734777284

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.009777968477161

> <JCHEM_PKA_STRONGEST_BASIC>
-4.409664764474442

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
46.0963

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.56e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
caffeyl aldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-AUG-19         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0      -1.334  -2.310   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0       2.667  -3.080   0.000  0.00  0.00           H+0
CONECT    1    2    5   13                                                  
CONECT    2    1    7   14                                                  
CONECT    3    4    7                                                       
CONECT    4    3    8                                                       
CONECT    5    1   10                                                       
CONECT    6    7    9                                                       
CONECT    7    2    3    6                                                  
CONECT    8    4    9   11                                                  
CONECT    9    6    8   12                                                  
CONECT   10    5                                                            
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13    1                                                            
CONECT   14    2                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
(2E)-3-(3,4-Dihydroxyphenyl)acrylaldehyde	ChEBI
(e)-3,4-Dihydroxycinnamaldehyde	ChEBI
(e)-Caffeyl aldehyde	ChEBI
Caffeic aldehyde	ChEBI
Caffeyl aldehyde	ChEBI
trans-3,4-Dihydroxycinnamaldehyde	ChEBI
3,4-Dihydroxycinnamaldehyde	Kegg

Chemical Formula

C₉H₈O₃

Average Mass

164.1600 Da

Monoisotopic Mass

164.04734 Da

IUPAC Name

(2E)-3-(3,4-dihydroxyphenyl)prop-2-enal

Traditional Name

caffeyl aldehyde

CAS Registry Number

Not Available

SMILES

[H]\C(C=O)=C(\[H])C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C9H8O3/c10-5-1-2-7-3-4-8(11)9(12)6-7/h1-6,11-12H/b2-1+

InChI Key

AXMVYSVVTMKQSL-OWOJBTEDSA-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, 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

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Arabidopsis thaliana	Plant	KNApSAcK
Carica papaya L.	Plant	KNApSAcK
Daphnia pulex	LOTUS Database	35616633
Ilex paraguariensis	Plant	KNApSAcK
Petasites tricholobus	Plant	KNApSAcK
Populus trichocarpa	Plant	KNApSAcK
Tachigali paniculata	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
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Alpha,beta-unsaturated aldehyde
Enal
Aldehyde
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

catechols (CHEBI:28323 )
cinnamaldehydes (CHEBI:28323 )
Caffeate derivatives (C10945 )

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	1.71	ALOGPS
logP	1.37	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.01	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	46.1 m³·mol⁻¹	ChemAxon
Polarizability	16.37 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

HMDB0141767

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00007511

Chemspider ID

4445164

KEGG Compound ID

C10945

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Caffeic aldehyde

METLIN ID

Not Available

PubChem Compound

5281871

PDB ID

Not Available

ChEBI ID

28323

Good Scents ID

Not Available

References

General References

Guo D, Chen F, Dixon RA: Monolignol biosynthesis in microsomal preparations from lignifying stems of alfalfa (Medicago sativa L.). Phytochemistry. 2002 Nov;61(6):657-67. doi: 10.1016/s0031-9422(02)00375-8. [PubMed:12423886 ]
Zhou R, Jackson L, Shadle G, Nakashima J, Temple S, Chen F, Dixon RA: Distinct cinnamoyl CoA reductases involved in parallel routes to lignin in Medicago truncatula. Proc Natl Acad Sci U S A. 2010 Oct 12;107(41):17803-8. doi: 10.1073/pnas.1012900107. Epub 2010 Sep 27. [PubMed:20876124 ]

Showing NP-Card for 3,4-Dihydroxycinnamaldehyde (NP0054993)

MOL for NP0054993 (3,4-Dihydroxycinnamaldehyde)

3D MOL for NP0054993 (3,4-Dihydroxycinnamaldehyde)

3D SDF for NP0054993 (3,4-Dihydroxycinnamaldehyde)

3D-SDF for NP0054993 (3,4-Dihydroxycinnamaldehyde)

PDB for NP0054993 (3,4-Dihydroxycinnamaldehyde)

3D PDB for NP0054993 (3,4-Dihydroxycinnamaldehyde)

SMILES for NP0054993 (3,4-Dihydroxycinnamaldehyde)

INCHI for NP0054993 (3,4-Dihydroxycinnamaldehyde)

Structure for NP0054993 (3,4-Dihydroxycinnamaldehyde)

3D Structure for NP0054993 (3,4-Dihydroxycinnamaldehyde)