NP-MRD: Showing NP-Card for 2-O-Caffeoylhydroxycitric acid (NP0049672)

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Record Information

Version

2.0

Created at

2022-03-17 21:16:15 UTC

Updated at

2022-03-17 21:16:15 UTC

NP-MRD ID

NP0049672

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-O-Caffeoylhydroxycitric acid

Description

2-O-Caffeoylhydroxycitric acid belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. 2-O-Caffeoylhydroxycitric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-O-Caffeoylhydroxycitric acid has been detected, but not quantified in, several different foods, such as cereals and cereal products, corns, fats and oils, and fruits. 2-O-Caffeoylhydroxycitric acid is found in Spondias mombin . This could make 2-O-caffeoylhydroxycitric acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061311572D          

 26 26  0  0  0  0            999 V2000
   -3.2529   -0.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8831    0.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0394   -1.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2997    1.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8727   -0.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696    0.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2425   -1.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6591   -0.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9299    5.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5133    2.3322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9403    3.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5600    4.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0290   -2.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8623   -1.0688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5133    6.2595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1330    5.8896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3101    2.5458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5237    3.3427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1538    4.7229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902    2.9156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1798    3.9260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767    4.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9299    2.9156    0.0000 O   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
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  5  2  0  0  0  0
  8  3  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  6  1  0  0  0  0
 11  4  1  0  0  0  0
 13 12  1  0  0  0  0
 15  6  1  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  2  0  0  0  0
 19 10  1  0  0  0  0
 20 11  2  0  0  0  0
 21 13  2  0  0  0  0
 22 13  1  0  0  0  0
 23 14  2  0  0  0  0
 24 14  1  0  0  0  0
 25 15  1  0  0  0  0
 26 11  1  0  0  0  0
 26 12  1  0  0  0  0
M  END


  Mrv0541 05061311572D          

 26 26  0  0  0  0            999 V2000
   -3.2529   -0.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8831    0.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0394   -1.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2997    1.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8727   -0.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696    0.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2425   -1.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6591   -0.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9299    5.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5133    2.3322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9403    3.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5600    4.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0290   -2.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8623   -1.0688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5133    6.2595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1330    5.8896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3101    2.5458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5237    3.3427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1538    4.7229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902    2.9156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1798    3.9260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767    4.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9299    2.9156    0.0000 O   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
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  5  2  0  0  0  0
  8  3  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  6  1  0  0  0  0
 11  4  1  0  0  0  0
 13 12  1  0  0  0  0
 15  6  1  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  2  0  0  0  0
 19 10  1  0  0  0  0
 20 11  2  0  0  0  0
 21 13  2  0  0  0  0
 22 13  1  0  0  0  0
 23 14  2  0  0  0  0
 24 14  1  0  0  0  0
 25 15  1  0  0  0  0
 26 11  1  0  0  0  0
 26 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049672

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O11/c16-8-3-1-7(5-9(8)17)2-4-11(20)26-12(13(21)22)15(25,14(23)24)6-10(18)19/h1-5,12,16-17,25H,6H2,(H,18,19)(H,21,22)(H,23,24)/b4-2+

> <INCHI_KEY>
OUWOVSUGDPWIBY-DUXPYHPUSA-N

> <FORMULA>
C15H14O11

> <MOLECULAR_WEIGHT>
370.2651

> <EXACT_MASS>
370.05361129

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
32.647450538137505

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropane-1,2,3-tricarboxylic acid

> <ALOGPS_LOGP>
1.45

> <JCHEM_LOGP>
0.3889141619999997

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.307531128476228

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8680808650348317

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5894545120764745

> <JCHEM_POLAR_SURFACE_AREA>
198.88999999999996

> <JCHEM_REFRACTIVITY>
80.49159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropane-1,2,3-tricarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -6.072  -0.799   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.382   1.777   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.674  -2.287   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.293   2.866   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.496  -0.109   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   9.108   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.983   0.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.186  -2.686   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.097  -1.597   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.602  10.595   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.691   4.353   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.489   7.329   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.823   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.912   8.019   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.787  -4.173   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.610  -1.995   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -4.691  11.684   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.115  10.994   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -6.179   4.752   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.578   6.240   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -5.887   8.816   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.222   5.442   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.336   7.329   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.823   9.108   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -3.602   5.442   0.000  0.00  0.00           O+0
CONECT    1    3    7                                                       
CONECT    2    4    7                                                       
CONECT    3    1    8                                                       
CONECT    4    2   11                                                       
CONECT    5    7    9                                                       
CONECT    6   10   15                                                       
CONECT    7    1    2    5                                                  
CONECT    8    3    9   16                                                  
CONECT    9    5    8   17                                                  
CONECT   10    6   18   19                                                  
CONECT   11    4   20   26                                                  
CONECT   12   13   15   26                                                  
CONECT   13   12   21   22                                                  
CONECT   14   15   23   24                                                  
CONECT   15    6   12   14   25                                             
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   10                                                            
CONECT   20   11                                                            
CONECT   21   13                                                            
CONECT   22   13                                                            
CONECT   23   14                                                            
CONECT   24   14                                                            
CONECT   25   15                                                            
CONECT   26   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

View in JSmol

Synonyms

Value	Source
2-O-Caffeoylhydroxycitrate	Generator
1-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropane-1,2,3-tricarboxylate	Generator

Chemical Formula

C₁₅H₁₄O₁₁

Average Mass

370.2651 Da

Monoisotopic Mass

370.05361 Da

IUPAC Name

1-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropane-1,2,3-tricarboxylic acid

Traditional Name

1-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropane-1,2,3-tricarboxylic acid

CAS Registry Number

62345-87-3

SMILES

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

InChI Identifier

InChI=1S/C15H14O11/c16-8-3-1-7(5-9(8)17)2-4-11(20)26-12(13(21)22)15(25,14(23)24)6-10(18)19/h1-5,12,16-17,25H,6H2,(H,18,19)(H,21,22)(H,23,24)/b4-2+

InChI Key

OUWOVSUGDPWIBY-DUXPYHPUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Spondias mombin	Plant	KNApSAcK
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Coumaric acid or derivatives
Cinnamic acid or derivatives
Styrene
Catechol
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monosaccharide
Monocyclic benzene moiety
Alpha-hydroxy acid
Hydroxy acid
Benzenoid
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
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	1.45	ALOGPS
logP	0.39	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	2.87	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	198.89 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	80.49 m³·mol⁻¹	ChemAxon
Polarizability	32.65 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0040572

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020350

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

24797519

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-O-Caffeoylhydroxycitric acid (NP0049672)

MOL for NP0049672 (2-O-Caffeoylhydroxycitric acid)

3D MOL for NP0049672 (2-O-Caffeoylhydroxycitric acid)

3D SDF for NP0049672 (2-O-Caffeoylhydroxycitric acid)

3D-SDF for NP0049672 (2-O-Caffeoylhydroxycitric acid)

PDB for NP0049672 (2-O-Caffeoylhydroxycitric acid)

3D PDB for NP0049672 (2-O-Caffeoylhydroxycitric acid)

SMILES for NP0049672 (2-O-Caffeoylhydroxycitric acid)

INCHI for NP0049672 (2-O-Caffeoylhydroxycitric acid)

Structure for NP0049672 (2-O-Caffeoylhydroxycitric acid)

3D Structure for NP0049672 (2-O-Caffeoylhydroxycitric acid)