NP-MRD: Showing NP-Card for 3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid (NP0334426)

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Record Information

Version

2.0

Created at

2024-09-09 23:36:46 UTC

Updated at

2024-09-09 23:36:46 UTC

NP-MRD ID

NP0334426

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid

Description

NULL

Structure

MOL SDF PDB SMILES InChI

  Mrv1652310151921552D          

 17 17  0  0  0  0            999 V2000
    1.2822    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4790   -2.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -2.9975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2995   -2.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12 11  1  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15 12  2  0  0  0  0
 16 12  1  0  0  0  0
 17  8  1  0  0  0  0
 17  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334426

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC1=C(C)C(C(O)=O)=C(CCC(O)=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C12H16O5/c1-3-4-8-7(2)11(12(15)16)9(17-8)5-6-10(13)14/h3-6H2,1-2H3,(H,13,14)(H,15,16)

> <INCHI_KEY>
WMCQWXZMVIETAO-UHFFFAOYSA-N

> <FORMULA>
C12H16O5

> <MOLECULAR_WEIGHT>
240.2524

> <EXACT_MASS>
240.099773622

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.26012299065896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic acid

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
2.2975586346666668

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.784928733133732

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8672044770544063

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9255026501474064

> <JCHEM_POLAR_SURFACE_AREA>
87.74

> <JCHEM_REFRACTIVITY>
61.083600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2-carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-OCT-19         0                                  
HETATM    1  C   UNK     0       2.393   5.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.011  -2.943   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.894  -4.188   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.268  -5.595   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.426  -4.027   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.109  -2.943   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.267  -1.375   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    7                                                            
CONECT    3    1    4                                                       
CONECT    4    3    8                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    2    8   11                                                  
CONECT    8    4    7   17                                                  
CONECT    9    5   11   17                                                  
CONECT   10    6   13   14                                                  
CONECT   11    7    9   12                                                  
CONECT   12   11   15   16                                                  
CONECT   13   10                                                            
CONECT   14   10                                                            
CONECT   15   12                                                            
CONECT   16   12                                                            
CONECT   17    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
CMPF	ChEBI
3-Carboxy-4-methyl-5-propyl-2-furanpropionate	Generator
3-Carboxy-4-methyl-5-propyl-2-furan-propanoate	HMDB
U(3,3)	HMDB
CMPFPA	HMDB
3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid	HMDB
Propylurofuranic acid	HMDB
3-Carboxy-4-methyl-5-propyl-2-furanpropanoate	HMDB
2-(2-Carboxyethyl)-4-methyl-4-propylfuran-3-carboxylic acid	HMDB
3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid	HMDB, ChEBI

Chemical Formula

C₁₂H₁₆O₅

Average Mass

240.2524 Da

Monoisotopic Mass

240.09977 Da

IUPAC Name

2-(2-carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic acid

Traditional Name

2-(2-carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCCC1=C(C)C(C(O)=O)=C(CCC(O)=O)O1

InChI Identifier

InChI=1S/C12H16O5/c1-3-4-8-7(2)11(12(15)16)9(17-8)5-6-10(13)14/h3-6H2,1-2H3,(H,13,14)(H,15,16)

InChI Key

WMCQWXZMVIETAO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoid fatty acids. These are fatty acids containing a 5-alkylfuran-2-alkanoic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Furanoid fatty acids

Alternative Parents

Substituents

Furanoid fatty acid
Furoic acid or derivatives
Furan-3-carboxylic acid
Furan-3-carboxylic acid or derivatives
Furoic acid
Dicarboxylic acid or derivatives
Furan
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:41254 )
furoic acid (CHEBI:41254 )
Heterocyclic fatty acids (LMFA01150004 )

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	2.3	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.74 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	61.08 m³·mol⁻¹	ChemAxon
Polarizability	25.26 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

HMDB0061112

DrugBank ID

DB07517

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB093609

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

123979

PDB ID

Not Available

ChEBI ID

41254

Good Scents ID

Not Available

References

General References

Niwa T: Organic acids and the uremic syndrome: protein metabolite hypothesis in the progression of chronic renal failure. Semin Nephrol. 1996 May;16(3):167-82. [PubMed:8734460 ]
Sakai T, Takadate A, Otagiri M: Characterization of binding site of uremic toxins on human serum albumin. Biol Pharm Bull. 1995 Dec;18(12):1755-61. doi: 10.1248/bpb.18.1755. [PubMed:8787801 ]
Tsutsumi Y, Deguchi T, Takano M, Takadate A, Lindup WE, Otagiri M: Renal disposition of a furan dicarboxylic acid and other uremic toxins in the rat. J Pharmacol Exp Ther. 2002 Nov;303(2):880-7. doi: 10.1124/jpet.303.2.880. [PubMed:12388676 ]
Niwa T: Recent progress in the analysis of uremic toxins by mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Sep 1;877(25):2600-6. doi: 10.1016/j.jchromb.2008.11.032. Epub 2008 Nov 27. [PubMed:19083276 ]
Deguchi T, Ohtsuki S, Otagiri M, Takanaga H, Asaba H, Mori S, Terasaki T: Major role of organic anion transporter 3 in the transport of indoxyl sulfate in the kidney. Kidney Int. 2002 May;61(5):1760-8. doi: 10.1046/j.1523-1755.2002.00318.x. [PubMed:11967025 ]

Showing NP-Card for 3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid (NP0334426)

MOL for NP0334426 (3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid)

3D MOL for NP0334426 (3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid)

3D SDF for NP0334426 (3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid)

3D-SDF for NP0334426 (3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid)

PDB for NP0334426 (3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid)

3D PDB for NP0334426 (3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid)

SMILES for NP0334426 (3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid)

INCHI for NP0334426 (3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid)

Structure for NP0334426 (3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid)

3D Structure for NP0334426 (3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid)