NP-MRD: Showing NP-Card for 3,4-Dihydroxyphenyl caffeate (NP0081757)

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Record Information

Version

2.0

Created at

2022-04-29 02:50:00 UTC

Updated at

2022-04-29 02:50:00 UTC

NP-MRD ID

NP0081757

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4-Dihydroxyphenyl caffeate

Description

3,4-Dihydroxyphenyl caffeate belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. 3,4-Dihydroxyphenyl caffeate is found in Froelichia floridana. 3,4-Dihydroxyphenyl caffeate was first documented in 2014 (PMID: 24472393). Based on a literature review very few articles have been published on 3,4-dihydroxyphenyl caffeate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -1.3686   -0.0154   -2.4165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7098   -0.0737   -1.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7392    0.0582   -1.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3878   -0.0079   -0.1850 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8361    0.1158   -0.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6558    0.3142   -1.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0357    0.4288   -0.9942 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6025    0.3396    0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9682    0.4464    0.4615 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983    0.1382    1.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3837    0.0508    2.6286 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382    0.0317    1.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4589   -0.2774   -0.1820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8410   -0.4056   -0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4330   -1.6426   -0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8261   -1.7388   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6075   -0.6202   -0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9884   -0.7070   -0.2598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0263    0.6149   -0.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7899    1.7496    0.0267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6689    0.6980   -0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2589    0.2127   -2.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7981   -0.1665    0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2761    0.3914   -2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6838    0.5863   -1.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5502    0.5933   -0.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7631   -0.0968    3.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8166   -0.1251    2.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549   -2.5583   -0.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2673   -2.7087   -0.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6043    0.0654   -0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3765    2.6525    0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1708    1.6565    0.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 19  2  0
 19 20  1  0
 19 21  1  0
 21 14  2  0
 14 13  1  0
 13  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 12  2  0
 12 10  1  0
 10 11  1  0
 10  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  6  5  1  0
 18 31  1  0
 20 32  1  0
 21 33  1  0
  3 22  1  0
  4 23  1  0
 12 28  1  0
 11 27  1  0
  9 26  1  0
  7 25  1  0
  6 24  1  0
 15 29  1  0
 16 30  1  0
M  END


  Mrv1652304292204502D          

 21 22  0  0  0  0            999 V2000
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   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
    0.7145    2.0625    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    0.8250    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
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  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
  7 12  1  0  0  0  0
 10 13  1  0  0  0  0
  9 14  1  0  0  0  0
  1 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  1 19  1  0  0  0  0
 17 20  1  0  0  0  0
 16 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0081757

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(O)C=C(OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O6/c16-11-4-1-9(7-13(11)18)2-6-15(20)21-10-3-5-12(17)14(19)8-10/h1-8,16-19H/b6-2+

> <INCHI_KEY>
NIYQPBJUTVQCLM-QHHAFSJGSA-N

> <FORMULA>
C15H12O6

> <MOLECULAR_WEIGHT>
288.255

> <EXACT_MASS>
288.063388106

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.496168758458516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
2.9590108113333335

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.40465520032042

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.769766195007456

> <JCHEM_PKA_STRONGEST_BASIC>
-6.251351331219479

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
75.53020000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dihydroxyphenyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334  13.090   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.001  11.550   0.000  0.00  0.00           O+0
CONECT    1    2   15   19                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   10                                                            
CONECT   14    9                                                            
CONECT   15    1   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18    1                                                       
CONECT   20   17                                                            
CONECT   21   16                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
3,4-Dihydroxyphenyl caffeic acid	Generator

Chemical Formula

C₁₅H₁₂O₆

Average Mass

288.2550 Da

Monoisotopic Mass

288.06339 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC1=C(O)C=C(OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C=C1

InChI Identifier

InChI=1S/C15H12O6/c16-11-4-1-9(7-13(11)18)2-6-15(20)21-10-3-5-12(17)14(19)8-10/h1-8,16-19H/b6-2+

InChI Key

NIYQPBJUTVQCLM-QHHAFSJGSA-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
Froelichia floridana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Phenol ester
Catechol
Phenoxy compound
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Fatty acid ester
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

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	2.61	ALOGPS
logP	2.96	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.77	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	75.53 m³·mol⁻¹	ChemAxon
Polarizability	28.5 Å³	ChemAxon
Number of Rings	2	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00048279

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

102519768

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Al-Qudah MA, Al-Jaber HI, Abu Zarga MH, Abu Orabi ST: Flavonoid and phenolic compounds from Salvia palaestina L. growing wild in Jordan and their antioxidant activities. Phytochemistry. 2014 Mar;99:115-20. doi: 10.1016/j.phytochem.2014.01.001. Epub 2014 Jan 25. [PubMed:24472393 ]

Showing NP-Card for 3,4-Dihydroxyphenyl caffeate (NP0081757)

MOL for NP0081757 (3,4-Dihydroxyphenyl caffeate)

3D MOL for NP0081757 (3,4-Dihydroxyphenyl caffeate)

3D SDF for NP0081757 (3,4-Dihydroxyphenyl caffeate)

3D-SDF for NP0081757 (3,4-Dihydroxyphenyl caffeate)

PDB for NP0081757 (3,4-Dihydroxyphenyl caffeate)

3D PDB for NP0081757 (3,4-Dihydroxyphenyl caffeate)

SMILES for NP0081757 (3,4-Dihydroxyphenyl caffeate)

INCHI for NP0081757 (3,4-Dihydroxyphenyl caffeate)

Structure for NP0081757 (3,4-Dihydroxyphenyl caffeate)

3D Structure for NP0081757 (3,4-Dihydroxyphenyl caffeate)