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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:48:02 UTC

Update Date

2023-02-21 17:21:38 UTC

HMDB ID

HMDB0032131

Secondary Accession Numbers

HMDB0125527
HMDB32131

Metabolite Identification

Common Name

3,5-Dihydroxycinnamic acid

Description

3,5-Dihydroxycinnamic acid (DHA) (CAS: 28374-93-8) is found in fruits. It can be isolated from peach buds. BioTransformer predicts that 3,5-dihydroxycinnamic acid is a product of 3,4,5-trihydroxycinnamic acid metabolism via a -4p-dehydroxylation-of-substituted-benzene reaction occurring in human gut microbiota and catalyzed by a dehydroxylase enzyme (PMID: 30612223 ). 3,5-Dihydroxycinnamic acid is an alkylresorcinol metabolite. It is a potential urinary biomarker of whole grain intake (PMID: 28444884 ).

Structure

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

  Mrv1652308071918062D          

 13 13  0  0  0  0            999 V2000
    1.7860    0.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008    0.0015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571    0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571   -0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0715    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3569    0.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5007    0.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -2.0622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  4  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11  4  1  0  0  0  0
  6 12  1  0  0  0  0
  8 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032131

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O4/c10-7-3-6(1-2-9(12)13)4-8(11)5-7/h1-5,10-11H,(H,12,13)/b2-1+

> <INCHI_KEY>
MFFCZSWTQMCKFP-OWOJBTEDSA-N

> <FORMULA>
C9H8O4

> <MOLECULAR_WEIGHT>
180.159

> <EXACT_MASS>
180.042258738

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
17.360742979074175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(3,5-dihydroxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
1.5289556166666665

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.167249502959805

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6346470217964715

> <JCHEM_PKA_STRONGEST_BASIC>
-5.6785511467900855

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
47.021699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(3,5-dihydroxyphenyl)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-AUG-19         0                                  
HETATM    1  C   UNK     0       3.334   0.772   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.668   0.003   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.334   2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.001   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.334   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.334  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.667  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.000   0.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.666   0.771   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.668   0.770   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.001  -3.849   0.000  0.00  0.00           O+0
CONECT    1    2    3   10                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    5    9   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8    4                                                       
CONECT   10    1   11                                                       
CONECT   11   10    4                                                       
CONECT   12    6                                                            
CONECT   13    8                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,5-Dihydroxycinnamate	Generator
(2E)-3-(3,5-Dihydroxyphenyl)prop-2-enoate	HMDB
(2E)-3-(3,5-Dihydroxyphenyl)-2-propenoic acid	HMDB
(e)-3-(3,5-Dihydroxyphenyl)acrylic acid	HMDB
3-(3,5-Dihydroxyphenyl)-2-propenoic acid	HMDB
3-(3,5-Dihydroxyphenyl)prop-2-enoic acid	HMDB
DHCA	HMDB
3,5-Dihydroxycinnamic acid	HMDB

Chemical Formula

C₉H₈O₄

Average Molecular Weight

180.159

Monoisotopic Molecular Weight

180.042258738

IUPAC Name

(2E)-3-(3,5-dihydroxyphenyl)prop-2-enoic acid

Traditional Name

(2E)-3-(3,5-dihydroxyphenyl)prop-2-enoic acid

CAS Registry Number

127791-54-2

SMILES

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

InChI Identifier

InChI=1S/C9H8O4/c10-7-3-6(1-2-9(12)13)4-8(11)5-7/h1-5,10-11H,(H,12,13)/b2-1+

InChI Key

MFFCZSWTQMCKFP-OWOJBTEDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Coumaric acid or derivatives
Hydroxycinnamic acid
Styrene
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0125527)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	245 - 246 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.45 g/L	ALOGPS
logP	1.47	ALOGPS
logP	1.53	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	3.63	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.02 m³·mol⁻¹	ChemAxon
Polarizability	17.36 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	136.91	30932474
DeepCCS	[M-H]-	134.515	30932474
DeepCCS	[M-2H]-	169.068	30932474
DeepCCS	[M+Na]+	143.527	30932474
AllCCS	[M+H]+	138.0	32859911
AllCCS	[M+H-H2O]+	133.7	32859911
AllCCS	[M+NH4]+	141.9	32859911
AllCCS	[M+Na]+	143.1	32859911
AllCCS	[M-H]-	134.1	32859911
AllCCS	[M+Na-2H]-	134.8	32859911
AllCCS	[M+HCOO]-	135.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,5-Dihydroxycinnamic acid	OC(=O)\C=C\C1=CC(O)=CC(O)=C1	3863.7	Standard polar	33892256
3,5-Dihydroxycinnamic acid	OC(=O)\C=C\C1=CC(O)=CC(O)=C1	1914.2	Standard non polar	33892256
3,5-Dihydroxycinnamic acid	OC(=O)\C=C\C1=CC(O)=CC(O)=C1	2068.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,5-Dihydroxycinnamic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C/C1=CC(O)=CC(O)=C1	2126.2	Semi standard non polar	33892256
3,5-Dihydroxycinnamic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC(/C=C/C(=O)O)=C1	2099.2	Semi standard non polar	33892256
3,5-Dihydroxycinnamic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C/C1=CC(O)=CC(O[Si](C)(C)C)=C1	2160.9	Semi standard non polar	33892256
3,5-Dihydroxycinnamic acid,2TMS,isomer #2	C[Si](C)(C)OC1=CC(/C=C/C(=O)O)=CC(O[Si](C)(C)C)=C1	2123.2	Semi standard non polar	33892256
3,5-Dihydroxycinnamic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C/C1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1	2142.4	Semi standard non polar	33892256
3,5-Dihydroxycinnamic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC(O)=CC(O)=C1	2367.1	Semi standard non polar	33892256
3,5-Dihydroxycinnamic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(/C=C/C(=O)O)=C1	2355.7	Semi standard non polar	33892256
3,5-Dihydroxycinnamic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1	2685.5	Semi standard non polar	33892256
3,5-Dihydroxycinnamic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C1	2648.1	Semi standard non polar	33892256
3,5-Dihydroxycinnamic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1	2887.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Dihydroxycinnamic acid GC-MS (3 TMS) - 70eV, Positive	splash10-00di-7049000000-ce53965ec25e00b0ce9b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Dihydroxycinnamic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-1900000000-d1d04d41b41d04d6945f	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Dihydroxycinnamic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Dihydroxycinnamic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 10V, Positive-QTOF	splash10-03di-0900000000-c1e096bdfab218e1788c	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 20V, Positive-QTOF	splash10-03dr-0900000000-3929e25bd302c5c206fc	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 40V, Positive-QTOF	splash10-00kr-6900000000-c72175f2a9a913be8c64	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 10V, Negative-QTOF	splash10-004i-0900000000-9ece1386317b857876d9	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 20V, Negative-QTOF	splash10-01ti-0900000000-d7db5e5f87f2edb1249b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 40V, Negative-QTOF	splash10-08gu-1900000000-0e0d1ce16d754f6cbdef	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 10V, Negative-QTOF	splash10-004r-0900000000-7f3073eac44d6b5f6242	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 20V, Negative-QTOF	splash10-000i-0900000000-98a352782abfdde7d3ea	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 40V, Negative-QTOF	splash10-000x-9600000000-cb090793e1bcf572facb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 10V, Positive-QTOF	splash10-03di-0900000000-3102fe8873d972cc4dd9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 20V, Positive-QTOF	splash10-01p9-1900000000-462d2391c15d8c9c830a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxycinnamic acid 40V, Positive-QTOF	splash10-0ftu-9700000000-a51ee75ddeef062d742e	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28444884	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031414

KNApSAcK ID

Not Available

Chemspider ID

4947733

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3,5-Dihydroxycinnamic acid

METLIN ID

Not Available

PubChem Compound

6443769

PDB ID

Not Available

ChEBI ID

189723

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5. [PubMed:30612223 ]
Wierzbicka R, Zamaratskaia G, Kamal-Eldin A, Landberg R: Novel urinary alkylresorcinol metabolites as biomarkers of whole grain intake in free-living Swedish adults. Mol Nutr Food Res. 2017 Jul;61(7). doi: 10.1002/mnfr.201700015. Epub 2017 Jun 14. [PubMed:28444884 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 3,5-Dihydroxycinnamic acid (HMDB0032131)

MOL for HMDB0032131 (3,5-Dihydroxycinnamic acid)

3D MOL for HMDB0032131 (3,5-Dihydroxycinnamic acid)

3D SDF for HMDB0032131 (3,5-Dihydroxycinnamic acid)

3D-SDF for HMDB0032131 (3,5-Dihydroxycinnamic acid)

PDB for HMDB0032131 (3,5-Dihydroxycinnamic acid)

3D PDB for HMDB0032131 (3,5-Dihydroxycinnamic acid)

SMILES for HMDB0032131 (3,5-Dihydroxycinnamic acid)

INCHI for HMDB0032131 (3,5-Dihydroxycinnamic acid)

Structure for HMDB0032131 (3,5-Dihydroxycinnamic acid)

3D Structure for HMDB0032131 (3,5-Dihydroxycinnamic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra