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Showing NP-Card for Isovalerylsarcosine (NP0086867)

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Record Information
Version1.0
Created at2022-05-11 16:33:14 UTC
Updated at2022-05-11 16:33:14 UTC
NP-MRD IDNP0086867
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsovalerylsarcosine
DescriptionIsovalerylsarcosine, also known as isopentanoylsarcosine, belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. An N-acyl-amino acid resulting from the formal condensation of carboxy group of isovaleric acid with the amino group of sarcosine. It was first documented in 1983 (PMID: 6197208). Isovalerylsarcosine is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 28005947).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086867 (Isovalerylsarcosine)


  Mrv0541 02231219212D          

 12 11  0  0  0  0            999 V2000
   16.3257   -9.7520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0401  -10.9895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1834   -8.9271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4690  -10.1646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6122   -9.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7546   -9.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8979  -10.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4690  -10.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3267  -10.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6122   -8.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0401  -10.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1834   -9.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2 11  2  0  0  0  0
  3 12  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  4 12  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
M  END
Download

3D MOL for NP0086867 (Isovalerylsarcosine)

     RDKit          3D

 27 26  0  0  0  0  0  0  0  0999 V2000
    3.4230   -0.6735   -0.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2020    0.2150   -0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1356    0.6739    1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9304   -0.4831   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2007    0.4572   -0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0181    1.6211   -0.0041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5233    0.0360   -0.6527 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854   -1.3196   -1.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6015    0.9815   -0.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1422    0.9303    0.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0874    1.6823    1.2518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5694    0.0302    1.7938 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1880   -0.2607    0.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8543   -0.5963   -1.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2280   -1.7211   -0.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3843    1.0917   -0.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167    0.1996    1.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1551    0.4261    1.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245    1.7847    1.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9142   -0.8781   -1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7480   -1.3286    0.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5751   -1.2730   -1.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1834   -1.9496   -0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9088   -1.7906   -1.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4085    0.6878   -1.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2568    2.0269   -0.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0797   -0.5699    2.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 12  1  0
 10 11  2  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 12 27  1  0
M  END
Download

3D SDF for NP0086867 (Isovalerylsarcosine)


  Mrv0541 02231219212D          

 12 11  0  0  0  0            999 V2000
   16.3257   -9.7520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0401  -10.9895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1834   -8.9271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4690  -10.1646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6122   -9.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7546   -9.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8979  -10.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4690  -10.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3267  -10.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6122   -8.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0401  -10.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1834   -9.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2 11  2  0  0  0  0
  3 12  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  4 12  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086867

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)N(C)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H15NO3/c1-6(2)4-7(10)9(3)5-8(11)12/h6H,4-5H2,1-3H3,(H,11,12)

> <INCHI_KEY>
GPFSWCRCPHKNBU-UHFFFAOYSA-N

> <FORMULA>
C8H15NO3

> <MOLECULAR_WEIGHT>
173.2096

> <EXACT_MASS>
173.105193351

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
17.991203626219665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(N,3-dimethylbutanamido)acetic acid

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
0.3271707199999999

> <ALOGPS_LOGS>
-0.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.248005066984846

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8644733090266451

> <JCHEM_POLAR_SURFACE_AREA>
57.61

> <JCHEM_REFRACTIVITY>
44.120400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.73e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isovalerylsarcosine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0086867 (Isovalerylsarcosine)

Download
PDB for NP0086867 (Isovalerylsarcosine)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      30.475 -18.204   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      31.808 -20.514   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      35.809 -16.664   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      34.475 -18.974   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      38.476 -18.204   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.142 -18.204   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      37.143 -18.974   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      34.475 -20.514   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      39.810 -18.974   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      38.476 -16.664   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.808 -18.974   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.809 -18.204   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4    6    8   12                                                  
CONECT    5    7    9   10                                                  
CONECT    6    4   11                                                       
CONECT    7    5   12                                                       
CONECT    8    4                                                            
CONECT    9    5                                                            
CONECT   10    5                                                            
CONECT   11    1    2    6                                                  
CONECT   12    3    4    7                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0086867 (Isovalerylsarcosine)
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SMILES for NP0086867 (Isovalerylsarcosine)
CC(C)CC(=O)N(C)CC(O)=O
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INCHI for NP0086867 (Isovalerylsarcosine)
InChI=1S/C8H15NO3/c1-6(2)4-7(10)9(3)5-8(11)12/h6H,4-5H2,1-3H3,(H,11,12)
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View in JSmol
Synonyms
ValueSource
(3-Methylbutanoyl)sarcosineChEBI
IsopentanoylsarcosineChEBI
N-(3-Methylbutanoyl)sarcosineChEBI
N-IsopentanoylsarcosineChEBI
N-IsovalerylsarcosineHMDB
IsovalerylsarcosineChEBI
Chemical FormulaC8H15NO3
Average Mass173.2096 Da
Monoisotopic Mass173.10519 Da
IUPAC Name2-(N,3-dimethylbutanamido)acetic acid
Traditional Nameisovalerylsarcosine
CAS Registry NumberNot Available
SMILES
CC(C)CC(=O)N(C)CC(O)=O
InChI Identifier
InChI=1S/C8H15NO3/c1-6(2)4-7(10)9(3)5-8(11)12/h6H,4-5H2,1-3H3,(H,11,12)
InChI KeyGPFSWCRCPHKNBU-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentN-acyl-alpha amino acids  
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
    • 

  • N-acyl-amine
    • 

  • Tertiary carboxylic acid amide
    • 

  • Carboxamide group
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.44ALOGPS
logP0.33ChemAxon
logS-0.8ALOGPS
pKa (Strongest Acidic)4.25ChemAxon
pKa (Strongest Basic)-0.86ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.61 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity44.12 m³·mol⁻¹ChemAxon
Polarizability17.99 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002087  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022838  
KNApSAcK IDNot Available
Chemspider ID121068  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6480  
PubChem Compound137394  
PDB IDNot Available
ChEBI ID136917  
Good Scents IDNot Available
References
General References
  1. Lehnert W: N-Isovalerylalanine and N-isovalerylsarcosine: two new minor metabolites in isovaleric acidemia. Clin Chim Acta. 1983 Oct 31;134(1-2):207-12. [PubMed:6197208  ] 
  2. Chen DY, Chen YM, Chien HJ, Lin CC, Hsieh CW, Chen HH, Hung WT, Lai CC: Metabolic Disturbances in Adult-Onset Still's Disease Evaluated Using Liquid Chromatography/Mass Spectrometry-Based Metabolomic Analysis. PLoS One. 2016 Dec 22;11(12):e0168147. doi: 10.1371/journal.pone.0168147. eCollection 2016. [PubMed:28005947  ]