NP-MRD: Showing NP-Card for cis-Caftaric acid (NP0047149)

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Record Information

Version

2.0

Created at

2022-03-17 20:35:27 UTC

Updated at

2022-03-17 20:35:27 UTC

NP-MRD ID

NP0047149

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cis-Caftaric acid

Description

cis-Caftaric acid is found in Allium obliquum , Fumaria capreolata , Fumaria officinalis , Fumaria schleicheri, Fumaria vaillantii , Syringodium filiforme, Thymus comosus, Thymus vulgaris , Vitis labrusca and Vitis vinifera.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533007131513492D          

 26 26  0  0  1  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    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
   -0.7145    2.8875    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  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  1  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
    0.0000   -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    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    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
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  4  1  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  2  0  0  0  0
 10 17  1  6  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
 20 13  2  0  0  0  0
 21 13  1  0  0  0  0
 22  9  1  0  0  0  0
 11 22  1  1  0  0  0
 23  2  1  0  0  0  0
 24  4  1  0  0  0  0
 10 25  1  6  0  0  0
 11 26  1  6  0  0  0
M  END


  Mrv1533007131513492D          

 26 26  0  0  1  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    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
   -0.7145    2.8875    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  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  1  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
    0.0000   -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    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    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
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  4  1  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  2  0  0  0  0
 10 17  1  6  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
 20 13  2  0  0  0  0
 21 13  1  0  0  0  0
 22  9  1  0  0  0  0
 11 22  1  1  0  0  0
 23  2  1  0  0  0  0
 24  4  1  0  0  0  0
 10 25  1  6  0  0  0
 11 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0047149

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2-/t10-,11+/m1/s1

> <INCHI_KEY>
SWGKAHCIOQPKFW-ADAMHKFESA-N

> <FORMULA>
C13H12O9

> <MOLECULAR_WEIGHT>
312.23

> <EXACT_MASS>
312.048131966

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.400632642045238

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R)-2-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
0.5979601859999999

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.484001795143949

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9580286110976193

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3456129955412335

> <JCHEM_POLAR_SURFACE_AREA>
161.59

> <JCHEM_REFRACTIVITY>
69.7429

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-2-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   5.390   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.334   0.770   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0      -5.335   3.080   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -5.335   0.000   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.334  -0.770   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.334  -0.770   0.000  0.00  0.00           H+0
CONECT    1    3    6                                                       
CONECT    2    4    6   23                                                  
CONECT    3    1    7                                                       
CONECT    4    2    9   24                                                  
CONECT    5    6    8                                                       
CONECT    6    1    2    5                                                  
CONECT    7    3    8   14                                                  
CONECT    8    5    7   15                                                  
CONECT    9    4   16   22                                                  
CONECT   10   11   12   17   25                                             
CONECT   11   10   13   22   26                                             
CONECT   12   10   18   19                                                  
CONECT   13   11   20   21                                                  
CONECT   14    7                                                            
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   12                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   13                                                            
CONECT   22    9   11                                                       
CONECT   23    2                                                            
CONECT   24    4                                                            
CONECT   25   10                                                            
CONECT   26   11                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R)-cis-Caffeoyl tartaric acid	ChEBI
(2S,3R)-cis-Caffeoyl tartarate	Generator
cis-Caftarate	Generator
cis-Caftaric acid	ChEBI
(2S,3R)-cis-Caftarate	Generator

Chemical Formula

C₁₃H₁₂O₉

Average Mass

312.2300 Da

Monoisotopic Mass

312.04813 Da

IUPAC Name

(2S,3R)-2-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

Traditional Name

(2S,3R)-2-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2-/t10-,11+/m1/s1

InChI Key

SWGKAHCIOQPKFW-ADAMHKFESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Allium obliquum	Plant	KNApSAcK
Fumaria capreolata	Plant	KNApSAcK
Fumaria officinalis	Plant	KNApSAcK
Fumaria schleicheri	Plant	KNApSAcK
Fumaria vaillantii	Plant	KNApSAcK
Syringodium filiforme	Plant	KNApSAcK
Thymus comosus	Plant	KNApSAcK
Thymus vulgaris	Plant	KNApSAcK
Vitis labrusca	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

catechols (CHEBI:76082 )
cinnamate ester (CHEBI:76082 )
dicarboxylic acid (CHEBI:76082 )
tetraric acid derivative (CHEBI:76082 )

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	1.68	ALOGPS
logP	0.6	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	2.96	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	161.59 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	69.74 m³·mol⁻¹	ChemAxon
Polarizability	27.4 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

FDB007549

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

72551521

PDB ID

Not Available

ChEBI ID

76082

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for cis-Caftaric acid (NP0047149)

MOL for NP0047149 (cis-Caftaric acid)

3D MOL for NP0047149 (cis-Caftaric acid)

3D SDF for NP0047149 (cis-Caftaric acid)

3D-SDF for NP0047149 (cis-Caftaric acid)

PDB for NP0047149 (cis-Caftaric acid)

3D PDB for NP0047149 (cis-Caftaric acid)

SMILES for NP0047149 (cis-Caftaric acid)

INCHI for NP0047149 (cis-Caftaric acid)

Structure for NP0047149 (cis-Caftaric acid)

3D Structure for NP0047149 (cis-Caftaric acid)