NP-MRD: Showing NP-Card for Daucic acid (NP0047306)

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Record Information

Version

2.0

Created at

2022-03-17 20:37:59 UTC

Updated at

2022-03-17 20:37:59 UTC

NP-MRD ID

NP0047306

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Daucic acid

Description

Daucic acid, also known as daucate, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Daucic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Daucic acid has been detected, but not quantified in, several different foods, such as carrots, sunflowers, wild carrots, root vegetables, and cereals and cereal products. Daucic acid was first documented in 2003 (PMID: 14673913). This could make daucic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061306032D          

 14 14  0  0  0  0            999 V2000
    1.4289    0.8250    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    0.0000    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
    0.0000    0.0000    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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -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
   -1.4289    0.0000    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  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  2  1  0  0  0  0
  9  4  1  0  0  0  0
 10  6  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 13  7  1  0  0  0  0
 14  3  1  0  0  0  0
 14  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047306

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C=C(OC(C1O)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O7/c8-2-1-3(6(10)11)14-5(4(2)9)7(12)13/h1-2,4-5,8-9H,(H,10,11)(H,12,13)

> <INCHI_KEY>
KUKCUROTFRBUNU-UHFFFAOYSA-N

> <FORMULA>
C7H8O7

> <MOLECULAR_WEIGHT>
204.1342

> <EXACT_MASS>
204.02700261

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
16.97865698500809

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4-dihydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid

> <ALOGPS_LOGP>
-0.98

> <JCHEM_LOGP>
-1.8191723806666664

> <ALOGPS_LOGS>
-0.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.6074530279457178

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.850376014220201

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4288327994727084

> <JCHEM_POLAR_SURFACE_AREA>
124.29000000000002

> <JCHEM_REFRACTIVITY>
40.9518

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.34e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dihydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic 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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4    8                                                  
CONECT    3    1    6   14                                                  
CONECT    4    2    5    9                                                  
CONECT    5    4    7   14                                                  
CONECT    6    3   10   11                                                  
CONECT    7    5   12   13                                                  
CONECT    8    2                                                            
CONECT    9    4                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
CONECT   13    7                                                            
CONECT   14    3    5                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
Daucate	Generator
(-)-Daucic acid	HMDB
2,6-Anhydro-3-deoxy-D-lyxo-hept-2-enaric acid	HMDB
2,6-Anhydro-3-deoxy-D-xylo-hept-2-enaric acid, 9ci	HMDB
3,4-Dihydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylate	Generator
Daucic acid	MeSH

Chemical Formula

C₇H₈O₇

Average Mass

204.1342 Da

Monoisotopic Mass

204.02700 Da

IUPAC Name

3,4-dihydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid

Traditional Name

3,4-dihydroxy-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid

CAS Registry Number

34098-52-7

SMILES

OC1C=C(OC(C1O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C7H8O7/c8-2-1-3(6(10)11)14-5(4(2)9)7(12)13/h1-2,4-5,8-9H,(H,10,11)(H,12,13)

InChI Key

KUKCUROTFRBUNU-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Daucus carota	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daucus carota ssp. sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Helianthus annuus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Pyran
Dicarboxylic acid or derivatives
1,2-diol
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-0.98	ALOGPS
logP	-1.8	ChemAxon
logS	-0.34	ALOGPS
pKa (Strongest Acidic)	2.85	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	40.95 m³·mol⁻¹	ChemAxon
Polarizability	16.98 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031665

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008325

KNApSAcK ID

Not Available

Chemspider ID

4475394

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5316316

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lichtenthaler FW, Nakamura K, Klotz J: (-)-Daucic acid: revision of configuration, synthesis, and biosynthetic implications. Angew Chem Int Ed Engl. 2003;42(47):5838-43. doi: 10.1002/anie.200352718. [PubMed:14673913 ]

Showing NP-Card for Daucic acid (NP0047306)

MOL for NP0047306 (Daucic acid)

3D MOL for NP0047306 (Daucic acid)

3D SDF for NP0047306 (Daucic acid)

3D-SDF for NP0047306 (Daucic acid)

PDB for NP0047306 (Daucic acid)

3D PDB for NP0047306 (Daucic acid)

SMILES for NP0047306 (Daucic acid)

INCHI for NP0047306 (Daucic acid)

Structure for NP0047306 (Daucic acid)

3D Structure for NP0047306 (Daucic acid)