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Showing NP-Card for 5-Phenylvaleric acid (NP0001374)

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Record Information
Version1.0
Created at2006-05-22 14:17:33 UTC
Updated at2021-10-07 20:38:25 UTC
NP-MRD IDNP0001374
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Phenylvaleric acid
Description5-Phenylvaleric acid, also known as delta-phenylvalerate or benzenepentanoic-acid, is a monocarboxylic acid that is valeric acid substituted by a phenyl group at the delta-position. It is a monocarboxylic acid and a member of benzenes. It derives from a valeric acid. 5-Phenylvaleric acid belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0001374 (5-Phenylvaleric acid)

5PV
  Mrv1652305271900002D          

 13 13  0  0  0  0            999 V2000
   -1.0563   -0.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708   -0.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4853   -0.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4853    0.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708    1.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0563    0.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3419   -0.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3726   -0.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0871   -0.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8015   -0.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5160   -0.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2305   -0.0459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5160   -1.2834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
Download

3D MOL for NP0001374 (5-Phenylvaleric acid)

HMDB0002043
     RDKit          3D
5-Phenylvaleric acid
 27 27  0  0  0  0  0  0  0  0999 V2000
    3.8060   -1.3832    0.4943 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6257   -0.1609    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5435    0.4335   -0.6494 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5350    0.6644    0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3132    0.5390   -0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8970   -0.8845   -0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3279   -1.1419   -0.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5112   -0.4150   -0.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8085    0.8362   -0.9473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9375    1.4769   -0.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7721    0.8690    0.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4832   -0.3944    0.9202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3414   -1.0187    0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4347   -0.0009   -0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3035    0.2866    1.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8850    1.7245    0.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5420    1.2304    0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6334    0.8818   -1.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7532   -1.4674   -0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7840   -1.2658    0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4898   -2.2457   -0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0808   -0.8532   -1.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1823    1.3647   -1.6829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1975    2.4785   -0.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6639    1.3491    0.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1299   -0.8809    1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1305   -2.0223    0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
M  END
Download

3D SDF for NP0001374 (5-Phenylvaleric acid)

5PV
  Mrv1652305271900002D          

 13 13  0  0  0  0            999 V2000
   -1.0563   -0.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708   -0.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4853   -0.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4853    0.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708    1.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0563    0.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3419   -0.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3726   -0.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0871   -0.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8015   -0.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5160   -0.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2305   -0.0459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5160   -1.2834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001374

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CCCCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H14O2/c12-11(13)9-5-4-8-10-6-2-1-3-7-10/h1-3,6-7H,4-5,8-9H2,(H,12,13)

> <INCHI_KEY>
BYHDDXPKOZIZRV-UHFFFAOYSA-N

> <FORMULA>
C11H14O2

> <MOLECULAR_WEIGHT>
178.2277

> <EXACT_MASS>
178.099379692

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.112580185383067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-phenylpentanoic acid

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
2.944700100333333

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.9403773022308055

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
51.1686

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-phenylvaleric acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0001374 (5-Phenylvaleric acid)

Download
PDB for NP0001374 (5-Phenylvaleric acid)
HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 5PV                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -1.972  -0.086   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.305  -0.856   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.639  -0.086   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.639   1.454   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.305   2.224   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.972   1.454   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.638  -0.856   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.696  -0.086   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.029  -0.856   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.363  -0.086   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.697  -0.856   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.030  -0.086   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.697  -2.396   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

Download
3D PDB for NP0001374 (5-Phenylvaleric acid)
Download
SMILES for NP0001374 (5-Phenylvaleric acid)
OC(=O)CCCCC1=CC=CC=C1
Download
INCHI for NP0001374 (5-Phenylvaleric acid)
InChI=1S/C11H14O2/c12-11(13)9-5-4-8-10-6-2-1-3-7-10/h1-3,6-7H,4-5,8-9H2,(H,12,13)
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View in JSmol
Synonyms
ValueSource
Benzenepentanoic-acidChEBI
delta-Phenylvaleric acidChEBI
Phenylpentanoic acidChEBI
Phenylvaleric acidChEBI
delta-PhenylvalerateGenerator
Δ-phenylvalerateGenerator
Δ-phenylvaleric acidGenerator
PhenylpentanoateGenerator
PhenylvalerateGenerator
5-PhenylvalerateGenerator
5-Phenyl valeric acidHMDB
5-Phenyl-pentanoateHMDB
5-Phenyl-pentanoic acidHMDB
5-PhenylpentanoateHMDB
5-Phenylpentanoic acidHMDB
5-Phenzylvaleric acidHMDB
BenzenepentanoateHMDB
Benzenepentanoic acidHMDB
5-PHENYLVALERIC ACIDChEBI
Chemical FormulaC11H14O2
Average Mass178.2277 Da
Monoisotopic Mass178.09938 Da
IUPAC Name5-phenylpentanoic acid
Traditional Name5-phenylvaleric acid
CAS Registry Number2270-20-4
SMILES
OC(=O)CCCCC1=CC=CC=C1
InChI Identifier
InChI=1S/C11H14O2/c12-11(13)9-5-4-8-10-6-2-1-3-7-10/h1-3,6-7H,4-5,8-9H2,(H,12,13)
InChI KeyBYHDDXPKOZIZRV-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)V.dorna832021-08-10View Spectrum
Species
Species of Origin
  • Eubacteria
    • Chemical Taxonomy
    Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
    KingdomOrganic compounds  
    Super ClassLipids and lipid-like molecules  
    ClassFatty Acyls  
    Sub ClassFatty acids and conjugates  
    Direct ParentMedium-chain fatty acids  
    Alternative Parents
    Substituents
    • Medium-chain fatty acid
      • 

    • Benzenoid
      • 

    • Monocyclic benzene moiety
      • 

    • Monocarboxylic acid or derivatives
      • 

    • Carboxylic acid
      • 

    • Carboxylic acid derivative
      • 

    • Organic oxygen compound
      • 

    • Organic oxide
      • 

    • Hydrocarbon derivative
      • 

    • Organooxygen compound
      • 

    • Carbonyl group
      • 

    • Aromatic homomonocyclic compound
    Molecular FrameworkAromatic homomonocyclic compounds
    External Descriptors
    Physical Properties
    StateSolid
    Experimental Properties
    PropertyValueReference
    Melting Point57.5 °CNot Available
    Boiling PointNot AvailableNot Available
    Water Solubility0.61 mg/mL at 25 °CNot Available
    LogP2.94Austin, R. P., Davis, A. M., & Manners, C. N. (1995). Partitioning of ionizing molecules between aqueous buffers and phospholipid vesicles. Journal of pharmaceutical sciences, 84(10), 1180-1183.
    Predicted Properties
    PropertyValueSource
    Water Solubility0.2 g/LALOGPS
    logP10(2.81) g/LALOGPS
    logP10(2.94) g/LChemAxon
    logS10(-2.9) g/LALOGPS
    pKa (Strongest Acidic)4.94ChemAxon
    Physiological Charge-1ChemAxon
    Hydrogen Acceptor Count2ChemAxon
    Hydrogen Donor Count1ChemAxon
    Polar Surface Area37.3 ŲChemAxon
    Rotatable Bond Count5ChemAxon
    Refractivity51.17 m³·mol⁻¹ChemAxon
    Polarizability20.11 ųChemAxon
    Number of Rings1ChemAxon
    BioavailabilityYesChemAxon
    Rule of FiveYesChemAxon
    Ghose FilterYesChemAxon
    Veber's RuleYesChemAxon
    MDDR-like RuleNoChemAxon
    HMDB IDHMDB0002043  
    DrugBank IDDB04051  
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB022814  
    KNApSAcK IDNot Available
    Chemspider ID15886  
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID6456  
    PubChem Compound16757  
    PDB IDNot Available
    ChEBI ID40131  
    Good Scents IDNot Available
    References
    General References
    1. Kim KR, Kim JH, Jeong DH, Paek DJ, Liebich HM: Gas chromatographic profiling analysis of urinary organic acids from nonsmokers and smokers. J Chromatogr B Biomed Sci Appl. 1997 Nov 7;701(1):1-8. [PubMed:9389332  ] 
    2. Mimori S, Okuma Y, Kaneko M, Kawada K, Hosoi T, Ozawa K, Nomura Y, Hamana H: Protective effects of 4-phenylbutyrate derivatives on the neuronal cell death and endoplasmic reticulum stress. Biol Pharm Bull. 2012;35(1):84-90. doi: 10.1248/bpb.35.84. [PubMed:22223342  ] 
    3. DeBold CR, Elwood JC: Mevalonic acid analogs as inhibitors of cholesterol biosynthesis. J Pharm Sci. 1981 Sep;70(9):1007-10. doi: 10.1002/jps.2600700910. [PubMed:6101142  ] 
    4. Rashed Y, Messele SA, Zeng H, Gamal El-Din M: Mesoporous carbon xerogel material for the adsorption of model naphthenic acids: structure effect and kinetics modelling. Environ Technol. 2020 Nov;41(27):3534-3543. doi: 10.1080/09593330.2019.1615130. Epub 2019 May 16. [PubMed:31046640  ] 
    5. Bitner BF, Ray JD, Kener KB, Herring JA, Tueller JA, Johnson DK, Tellez Freitas CM, Fausnacht DW, Allen ME, Thomson AH, Weber KS, McMillan RP, Hulver MW, Brown DA, Tessem JS, Neilson AP: Common gut microbial metabolites of dietary flavonoids exert potent protective activities in beta-cells and skeletal muscle cells. J Nutr Biochem. 2018 Dec;62:95-107. doi: 10.1016/j.jnutbio.2018.09.004. Epub 2018 Sep 15. [PubMed:30286378  ] 
    6. Guadamuro L, Jimenez-Giron AM, Delgado S, Florez AB, Suarez A, Martin-Alvarez PJ, Bartolome B, Moreno-Arribas MV, Mayo B: Profiling of Phenolic Metabolites in Feces from Menopausal Women after Long-Term Isoflavone Supplementation. J Agric Food Chem. 2016 Jan 13;64(1):210-6. doi: 10.1021/acs.jafc.5b05102. Epub 2015 Dec 31. [PubMed:26690567  ] 
    7. Jakobtorweihen S, Zuniga AC, Ingram T, Gerlach T, Keil FJ, Smirnova I: Predicting solute partitioning in lipid bilayers: Free energies and partition coefficients from molecular dynamics simulations and COSMOmic. J Chem Phys. 2014 Jul 28;141(4):045102. doi: 10.1063/1.4890877. [PubMed:25084963  ]