NP-MRD: Showing NP-Card for caffeoylmalic acid (NP0178420)

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Record Information

Version

2.0

Created at

2022-09-03 16:24:43 UTC

Updated at

2022-09-03 16:24:43 UTC

NP-MRD ID

NP0178420

Secondary Accession Numbers

None

Natural Product Identification

Common Name

caffeoylmalic acid

Description

2-{[3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid 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. caffeoylmalic acid is found in Liochlaena subulata, Marrubium velutinum, Panzerina lanata, Parietaria officinalis, Pyrus pyrifolia, Raphanus sativus, Trifolium pratense and Trifolium subterraneum. 2-{[3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
    6.0180    2.2229    0.3073 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3727    1.2129   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0215    0.2662   -0.8251 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9779    1.0719    0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362   -0.2548   -0.0165 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9694   -0.1089    0.4360 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9190   -0.2508   -0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1871   -0.5106   -1.6294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4672   -0.1055    0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4228   -0.2519   -0.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8428   -0.1296   -0.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8108   -0.3029   -1.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1563   -0.2002   -1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5781    0.0843    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9492    0.1831    0.2329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6605    0.2599    1.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0972    0.5452    2.2847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3168    0.1530    0.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9792   -1.3342    0.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3240   -1.9225    1.7072 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2820   -1.7357    0.6024 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0231    0.3031   -1.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3603    1.9174   -0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8228    1.2094    1.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4087   -0.4827   -1.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6512    0.1145    1.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1947   -0.4764   -1.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4726   -0.5298   -2.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8992   -0.3403   -2.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3403    0.3896    1.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4516    0.6836    3.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5778    0.2944    1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8869   -1.9747    1.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
  5 19  1  0
 19 21  1  0
 19 20  2  0
 18 11  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  6
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  1  0
M  END


  Mrv1533004181501362D          

 21 21  0  0  0  0            999 V2000
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  7  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 11 18  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0178420

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC(OC(=O)C=CC1=CC=C(O)C(O)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O8/c14-8-3-1-7(5-9(8)15)2-4-12(18)21-10(13(19)20)6-11(16)17/h1-5,10,14-15H,6H2,(H,16,17)(H,19,20)

> <INCHI_KEY>
PMKQSEYPLQIEAY-UHFFFAOYSA-N

> <FORMULA>
C13H12O8

> <MOLECULAR_WEIGHT>
296.231

> <EXACT_MASS>
296.053217346

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.958984237249382

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.3131186466666667

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.010506366272061

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.070120323000287

> <JCHEM_PKA_STRONGEST_BASIC>
-6.283762288194251

> <JCHEM_POLAR_SURFACE_AREA>
141.35999999999999

> <JCHEM_REFRACTIVITY>
68.4047

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.004 -13.860   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   11                                                       
CONECT   19    5   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioate	Generator

Chemical Formula

C₁₃H₁₂O₈

Average Mass

296.2310 Da

Monoisotopic Mass

296.05322 Da

IUPAC Name

2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

Traditional Name

2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CC(OC(=O)C=CC1=CC=C(O)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C13H12O8/c14-8-3-1-7(5-9(8)15)2-4-12(18)21-10(13(19)20)6-11(16)17/h1-5,10,14-15H,6H2,(H,16,17)(H,19,20)

InChI Key

PMKQSEYPLQIEAY-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Jungermannia subulata	LOTUS Database	35616633
Marrubium velutinum	LOTUS Database	35616633
Panzerina lanata	LOTUS Database	35616633
Parietaria officinalis	LOTUS Database	35616633
Pyrus pyrifolia	LOTUS Database	35616633
Raphanus sativus	LOTUS Database	35616633
Trifolium pratense	LOTUS Database	35616633
Trifolium subterraneum	LOTUS Database	35616633

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
Tricarboxylic acid or derivatives
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	1.87	ALOGPS
logP	1.31	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.07	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	141.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	68.4 m³·mol⁻¹	ChemAxon
Polarizability	26.96 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

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

4484594

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for caffeoylmalic acid (NP0178420)

MOL for NP0178420 (caffeoylmalic acid)

3D MOL for NP0178420 (caffeoylmalic acid)

3D SDF for NP0178420 (caffeoylmalic acid)

3D-SDF for NP0178420 (caffeoylmalic acid)

PDB for NP0178420 (caffeoylmalic acid)

3D PDB for NP0178420 (caffeoylmalic acid)

SMILES for NP0178420 (caffeoylmalic acid)

INCHI for NP0178420 (caffeoylmalic acid)

Structure for NP0178420 (caffeoylmalic acid)

3D Structure for NP0178420 (caffeoylmalic acid)