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Showing NP-Card for Hexanamide (NP0331900)

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Record Information
Version1.0
Created at2023-10-02 16:07:14 UTC
Updated at2024-04-19 09:55:10 UTC
NP-MRD IDNP0331900
Secondary Accession NumbersNone
Natural Product Identification
Common NameHexanamide
DescriptionHexanamide, also known as caproamide, belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine. It was first documented in 1999 (PMID: 10079066). Hexanamide is a very strong basic compound (based on its pKa) (PMID: 11556902) (PMID: 12773375) (PMID: 21043511).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0331900 (Hexanamide)


  Mrv1572004191603112D          

  8  7  0  0  0  0            999 V2000
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
M  END
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3D MOL for NP0331900 (Hexanamide)

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3D SDF for NP0331900 (Hexanamide)

  Mrv1572004191603112D          

  8  7  0  0  0  0            999 V2000
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331900

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(O)=N

> <INCHI_IDENTIFIER>
InChI=1S/C6H13NO/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H2,7,8)

> <INCHI_KEY>
ALBYIUDWACNRRB-UHFFFAOYSA-N

> <FORMULA>
C6H13NO

> <MOLECULAR_WEIGHT>
115.176

> <EXACT_MASS>
115.099714043

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
13.624461287554297

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
hexanimidic acid

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
-0.8213581174761674

> <ALOGPS_LOGS>
-1.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.3872407871855694

> <JCHEM_PKA_STRONGEST_BASIC>
13.971980476042338

> <JCHEM_POLAR_SURFACE_AREA>
44.08

> <JCHEM_REFRACTIVITY>
43.8324

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0331900 (Hexanamide)
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PDB for NP0331900 (Hexanamide)
HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      11.288   3.437   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0331900 (Hexanamide)
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SMILES for NP0331900 (Hexanamide)
CCCCCC(O)=N
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INCHI for NP0331900 (Hexanamide)
InChI=1S/C6H13NO/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H2,7,8)
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Synonyms
ValueSource
CaproamideChEBI
CapronamideChEBI
HexamideChEBI
HexanoamideChEBI
Hexanoic acid amideChEBI
HexylamideChEBI
N-CaproamideChEBI
N-Caproic amideChEBI
N-CapronamideChEBI
N-HexanamideChEBI
Hexanoate amideGenerator
Chemical FormulaC6H13NO
Average Mass115.1760 Da
Monoisotopic Mass115.09971 Da
IUPAC Namehexanimidic acid
Traditional Namehexanimidic acid
CAS Registry NumberNot Available
SMILES
CCCCCC(O)=N
InChI Identifier
InChI=1S/C6H13NO/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H2,7,8)
InChI KeyALBYIUDWACNRRB-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-02View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-02View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-02View Spectrum
1D NMR[13C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-02View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-02View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty amides  
Direct ParentFatty amides  
Alternative Parents
Substituents
  • Fatty amide
    • 

  • Primary carboxylic acid amide
    • 

  • Carboxamide group
    • 

  • Carboxylic acid derivative
    • 

  • 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 Descriptors
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
logP0.77ALOGPS
logP-0.82ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)0.39ChemAxon
pKa (Strongest Basic)13.97ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area44.08 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity43.83 m³·mol⁻¹ChemAxon
Polarizability13.62 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-10099  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12332  
PDB IDNot Available
ChEBI ID142683  
Good Scents IDNot Available
References
General References
  1. Wilcox BJ, Ritenour-Rodgers KJ, Asser AS, Baumgart LE, Baumgart MA, Boger DL, DeBlassio JL, deLong MA, Glufke U, Henz ME, King L 3rd, Merkler KA, Patterson JE, Robleski JJ, Vederas JC, Merkler DJ: N-acylglycine amidation: implications for the biosynthesis of fatty acid primary amides. Biochemistry. 1999 Mar 16;38(11):3235-45. doi: 10.1021/bi982255j. [PubMed:10079066  ] 
  2. Fournand D, Arnaud A: Aliphatic and enantioselective amidases: from hydrolysis to acyl transfer activity. J Appl Microbiol. 2001 Sep;91(3):381-93. doi: 10.1046/j.1365-2672.2001.01378.x. [PubMed:11556902  ] 
  3. Arand M, Hallberg BM, Zou J, Bergfors T, Oesch F, van der Werf MJ, de Bont JA, Jones TA, Mowbray SL: Structure of Rhodococcus erythropolis limonene-1,2-epoxide hydrolase reveals a novel active site. EMBO J. 2003 Jun 2;22(11):2583-92. doi: 10.1093/emboj/cdg275. [PubMed:12773375  ] 
  4. McIntyre NR, Lowe EW Jr, Belof JL, Ivkovic M, Shafer J, Space B, Merkler DJ: Evidence for substrate preorganization in the peptidylglycine alpha-amidating monooxygenase reaction describing the contribution of ground state structure to hydrogen tunneling. J Am Chem Soc. 2010 Nov 24;132(46):16393-402. doi: 10.1021/ja1019194. Epub 2010  Nov 2. [PubMed:21043511  ]