NP-MRD: Showing NP-Card for trans-caffeic acid (NP0141345)

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Record Information

Version

1.0

Created at

2022-07-18 17:04:01 UTC

Updated at

2022-07-18 17:11:07 UTC

NP-MRD ID

NP0141345

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trans-caffeic acid

Description

Caffeic acid, also known as trans-caffeate or sodium caffeate, 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. Caffeic acid has been detected, but not quantified in, several different foods, such as breakfast cereal, arabica coffees (Coffea arabica), peanuts (Arachis hypogaea), yellow wax beans (Phaseolus vulgaris), and fruits. This could make caffeic acid a potential biomarker for the consumption of these foods. Caffeic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. It was first documented in 2021 (PMID: 34426169). Based on a literature review a significant number of articles have been published on Caffeic acid (PMID: 35751193) (PMID: 34418969) (PMID: 34409742) (PMID: 34408988).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100163D          

 21 21  0  0  0  0            999 V2000
    1.6454   -2.0982    1.1823 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6545   -1.7851    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5851   -1.9289    1.0454 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5963   -1.2184   -0.8015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7347   -0.9823   -1.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7937   -0.4310   -2.8323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8562   -0.8169   -3.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9767   -0.3056   -4.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0340    0.6047   -5.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0944    1.1419   -6.6787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9880    1.0041   -4.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0694    1.9080   -5.0507 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8618    0.5012   -3.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4395   -2.3057    1.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3865   -1.0236   -1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6936   -1.2211   -1.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5990   -1.5302   -3.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037   -0.6279   -5.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8726    0.7710   -7.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3601    2.1161   -5.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431    0.8536   -2.6877 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 13  1  0  0  0  0
 11 12  1  0  0  0  0
  6  5  1  0  0  0  0
 13  6  2  0  0  0  0
  5  4  2  0  0  0  0
  9 11  2  0  0  0  0
  4  2  1  0  0  0  0
  6  7  1  0  0  0  0
  2  3  1  0  0  0  0
  7  8  2  0  0  0  0
  2  1  2  0  0  0  0
  8 18  1  0  0  0  0
 13 21  1  0  0  0  0
  7 17  1  0  0  0  0
 10 19  1  0  0  0  0
 12 20  1  0  0  0  0
  5 16  1  0  0  0  0
  4 15  1  0  0  0  0
  3 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0141345

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+

> <INCHI_KEY>
QAIPRVGONGVQAS-DUXPYHPUSA-N

> <FORMULA>
C9H8O4

> <MOLECULAR_WEIGHT>
180.1574

> <EXACT_MASS>
180.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
17.335364136589572

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
1.5289556166666665

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.276437669500657

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6438401388538604

> <JCHEM_PKA_STRONGEST_BASIC>
-6.283746523508147

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
47.021699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
caffeic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0       1.645  -2.098   1.182  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.655  -1.785   0.551  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.585  -1.929   1.045  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.596  -1.218  -0.802  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.735  -0.982  -1.471  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.794  -0.431  -2.832  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.856  -0.817  -3.669  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.977  -0.306  -4.966  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.034   0.605  -5.423  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.094   1.142  -6.679  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.988   1.004  -4.597  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.069   1.908  -5.051  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.862   0.501  -3.308  0.00  0.00           C+0
HETATM   14  H   UNK     0      -0.440  -2.306   1.938  0.00  0.00           H+0
HETATM   15  H   UNK     0      -0.387  -1.024  -1.211  0.00  0.00           H+0
HETATM   16  H   UNK     0       2.694  -1.221  -1.013  0.00  0.00           H+0
HETATM   17  H   UNK     0       3.599  -1.530  -3.316  0.00  0.00           H+0
HETATM   18  H   UNK     0       3.804  -0.628  -5.590  0.00  0.00           H+0
HETATM   19  H   UNK     0       2.873   0.771  -7.129  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.360   2.116  -5.961  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.043   0.854  -2.688  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    4    3    1                                                  
CONECT    3    2   14                                                       
CONECT    4    5    2   15                                                  
CONECT    5    6    4   16                                                  
CONECT    6    5   13    7                                                  
CONECT    7    6    8   17                                                  
CONECT    8    9    7   18                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   19                                                       
CONECT   11   13   12    9                                                  
CONECT   12   11   20                                                       
CONECT   13   11    6   21                                                  
CONECT   14    3                                                            
CONECT   15    4                                                            
CONECT   16    5                                                            
CONECT   17    7                                                            
CONECT   18    8                                                            
CONECT   19   10                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
3,4-Dihydroxy-trans-cinnamate	ChEBI
3,4-Dihydroxycinnamic acid	ChEBI
trans-Caffeate	ChEBI
3,4-Dihydroxy-trans-cinnamic acid	Generator
3,4-Dihydroxycinnamate	Generator
trans-Caffeic acid	Generator
Caffeate	Generator
Caffeic acid, monosodium salt	HMDB
Caffeic acid, (e)-isomer	HMDB
Sodium caffeate	HMDB
(2E)-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(e)-3,4-Dihydroxycinnamic acid	HMDB
(e)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(e)-3-(3,4-Dihydroxyphenyl)acrylic acid	HMDB
(e)-Caffeic acid	HMDB
3,4-Dihydroxybenzeneacrylic acid	HMDB
3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
3-(3,4-Dihydroxyphenyl)propenoic acid	HMDB
4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene	HMDB
4-(2-Carboxyethenyl)-1,2-dihydroxybenzene	HMDB
4-(2’-carboxyvinyl)-1,2-dihydroxybenzene	HMDB
DHCA	HMDB
trans-3,4-Dihydroxycinnamic acid	HMDB
3',4'-Dihydroxycinnamic acid	HMDB
3-(3,4-Dihydroxyphenyl)acrylic acid	HMDB
CAFFEIC ACID	ChEBI
Caffeic acid	HMDB

Chemical Formula

C₉H₈O₄

Average Mass

180.1574 Da

Monoisotopic Mass

180.04226 Da

IUPAC Name

(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

Traditional Name

caffeic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C(\[H])=C(/[H])C1=C([H])C(O[H])=C(O[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+

InChI Key

QAIPRVGONGVQAS-DUXPYHPUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, simulated)	Ahselim			2022-07-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, experimental)	Ahselim			2022-07-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Catechol
Styrene
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

caffeic acid (CHEBI:16433 )
Caffeate derivatives (C01197 )

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	1.67	ALOGPS
logP	1.53	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	-6.3	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	17.34 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

HMDB0001964

DrugBank ID

DB01880

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Caffeic_acid

METLIN ID

Not Available

PubChem Compound

689043

PDB ID

Not Available

ChEBI ID

16433

Good Scents ID

rw1622341

References

General References

Zhang D, Wang Z, Li J, Zhu J: Exploring the possible molecular targeting mechanism of Saussurea involucrata in the treatment of COVID-19 based on bioinformatics and network pharmacology. Comput Biol Med. 2022 Jul;146:105549. doi: 10.1016/j.compbiomed.2022.105549. Epub 2022 Apr 25. [PubMed:35751193 ]
Zhang SN, He YF, Li XZ, Yang WD, Zhou Y: Biolabel-led research pattern positions the effects and mechanisms of Sophorae Tonkinensis radix et rhizome on lung diseases: A novel strategy for computer-aided herbal medicine research based on omics and bioinformatics. Comput Biol Med. 2021 Sep;136:104769. doi: 10.1016/j.compbiomed.2021.104769. Epub 2021 Aug 18. [PubMed:34426169 ]
Khasin M, Bernhardson LF, O'Neill PM, Palmer NA, Scully ED, Sattler SE, Funnell-Harris DL: Pathogen and drought stress affect cell wall and phytohormone signaling to shape host responses in a sorghum COMT bmr12 mutant. BMC Plant Biol. 2021 Aug 21;21(1):391. doi: 10.1186/s12870-021-03149-5. [PubMed:34418969 ]
Li XZ, Zhang SN, Liu Q, Yang WD, Zhou Y: The active ingredients analysis of Herba Lysimachiae treating osteoarthritis based on the LC-MS/MS technology and public bioinformatics platforms. J Sep Sci. 2021 Oct;44(20):3799-3809. doi: 10.1002/jssc.202100390. Epub 2021 Aug 26. [PubMed:34409742 ]
de Barros PP, Rossoni RD, Garcia MT, Kaminski VL, Loures FV, Fuchs BB, Mylonakis E, Junqueira JC: The Anti-Biofilm Efficacy of Caffeic Acid Phenethyl Ester (CAPE) In Vitro and a Murine Model of Oral Candidiasis. Front Cell Infect Microbiol. 2021 Aug 2;11:700305. doi: 10.3389/fcimb.2021.700305. eCollection 2021. [PubMed:34408988 ]

Showing NP-Card for trans-caffeic acid (NP0141345)

MOL for NP0141345 (trans-caffeic acid)

3D MOL for NP0141345 (trans-caffeic acid)

3D SDF for NP0141345 (trans-caffeic acid)

3D-SDF for NP0141345 (trans-caffeic acid)

PDB for NP0141345 (trans-caffeic acid)

3D PDB for NP0141345 (trans-caffeic acid)

SMILES for NP0141345 (trans-caffeic acid)

INCHI for NP0141345 (trans-caffeic acid)

Structure for NP0141345 (trans-caffeic acid)

3D Structure for NP0141345 (trans-caffeic acid)