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Showing NP-Card for N-Acetylputrescine (NP0000452)

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Record Information
Version2.0
Created at2006-05-22 14:17:34 UTC
Updated at2021-06-29 00:47:20 UTC
NP-MRD IDNP0000452
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Acetylputrescine
DescriptionN-Acetylputrescine is a polyamine commonly occurring excreted in normal human urine (PMID 7775374 ). N-Acetylputrescine is the most abundant of all polyamines both in normal individuals and in patients with leukemia (PMID 9464484 ). N-Acetylputrescine is the N-acetylated form of the naturally occurring polyamine called putrescine. The N-acetylation is mediated by the enzyme diamine N-acetyltransferase. Putrescine is related to cadaverine (another polyamine). Both are produced by the breakdown of amino acids in living and dead organisms and both are toxic in large doses. Putrescine and cadaverine are largely responsible for the foul odor of putrefying flesh, but also contribute to the odor of such processes as bad breath and bacterial vaginosis. Putrescine is also found in semen. Putrescine attacks s-adenosyl methionine and converts it to spermidine. Spermidine in turn attacks another s-adenosyl methionine and converts it to spermine. Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase. N-Acetylputrescine can be found in Corynebacterium as well (PMID: 25919117 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000452 (N-Acetylputrescine)


  Mrv1652305271900222D          

  9  8  0  0  0  0            999 V2000
   27.9132   -3.4480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1988   -4.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.6263   -4.2730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.4842   -4.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3408   -4.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7698   -4.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0553   -4.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6277   -4.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9132   -4.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2  4  1  0  0  0  0
  2  9  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
Download

3D MOL for NP0000452 (N-Acetylputrescine)

HMDB0002064
     RDKit          3D
N-Acetylputrescine
 23 22  0  0  0  0  0  0  0  0999 V2000
    3.8911    0.5514    0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465   -0.4359    0.7977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1688   -1.0589    1.8108 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6971   -0.4921    0.0554 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5443   -0.5486   -0.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7050   -0.2048    0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8672   -0.2925   -0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1608    0.0066   -0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1623    1.3365    0.4733 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6705    0.6392    1.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2325    0.1188   -0.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4136    1.5466    0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1753   -1.4846    0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4977    0.2010   -1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3431   -1.5407   -1.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083    0.8198    0.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7942   -0.9054    0.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7369    0.5281   -1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8713   -1.2309   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3713   -0.7404    0.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9612   -0.0870   -0.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7792    1.9869   -0.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4628    1.2871    1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
M  END
Download

3D SDF for NP0000452 (N-Acetylputrescine)


  Mrv1652305271900222D          

  9  8  0  0  0  0            999 V2000
   27.9132   -3.4480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1988   -4.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.6263   -4.2730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.4842   -4.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3408   -4.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7698   -4.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0553   -4.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6277   -4.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9132   -4.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2  4  1  0  0  0  0
  2  9  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000452

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)NCCCCN

> <INCHI_IDENTIFIER>
InChI=1S/C6H14N2O/c1-6(9)8-5-3-2-4-7/h2-5,7H2,1H3,(H,8,9)

> <INCHI_KEY>
KLZGKIDSEJWEDW-UHFFFAOYSA-N

> <FORMULA>
C6H14N2O

> <MOLECULAR_WEIGHT>
130.1882

> <EXACT_MASS>
130.11061308

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
15.281189132520048

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(4-aminobutyl)acetamide

> <ALOGPS_LOGP>
-0.84

> <JCHEM_LOGP>
-1.0262736609999996

> <ALOGPS_LOGS>
0.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.482677381445836

> <JCHEM_PKA_STRONGEST_BASIC>
9.904074103986346

> <JCHEM_POLAR_SURFACE_AREA>
55.120000000000005

> <JCHEM_REFRACTIVITY>
36.8224

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetylputrescine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000452 (N-Acetylputrescine)

HMDB0002064
     RDKit          3D
N-Acetylputrescine
 23 22  0  0  0  0  0  0  0  0999 V2000
    3.8911    0.5514    0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465   -0.4359    0.7977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1688   -1.0589    1.8108 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6971   -0.4921    0.0554 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5443   -0.5486   -0.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7050   -0.2048    0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8672   -0.2925   -0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1608    0.0066   -0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1623    1.3365    0.4733 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6705    0.6392    1.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2325    0.1188   -0.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4136    1.5466    0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1753   -1.4846    0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4977    0.2010   -1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3431   -1.5407   -1.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083    0.8198    0.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7942   -0.9054    0.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7369    0.5281   -1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8713   -1.2309   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3713   -0.7404    0.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9612   -0.0870   -0.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7792    1.9869   -0.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4628    1.2871    1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  9 22  1  0
  9 23  1  0
M  END
Download

PDB for NP0000452 (N-Acetylputrescine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      52.105  -6.436   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      50.771  -8.746   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      44.102  -7.976   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      49.437  -7.976   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      45.436  -8.746   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      48.104  -8.746   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      46.770  -7.976   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      53.438  -8.746   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      52.105  -7.976   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    4    9                                                       
CONECT    3    5                                                            
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    7                                                       
CONECT    7    5    6                                                       
CONECT    8    9                                                            
CONECT    9    1    2    8                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for NP0000452 (N-Acetylputrescine)

COMPND    HMDB0002064
HETATM    1  C1  UNL     1       3.891   0.551   0.287  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.847  -0.436   0.798  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.169  -1.059   1.811  1.00  0.00           O  
HETATM    4  N1  UNL     1       1.697  -0.492   0.055  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.544  -0.549  -0.689  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.705  -0.205   0.144  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.867  -0.292  -0.810  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.161   0.007  -0.108  1.00  0.00           C  
HETATM    9  N2  UNL     1      -3.162   1.337   0.473  1.00  0.00           N  
HETATM   10  H1  UNL     1       4.670   0.639   1.034  1.00  0.00           H  
HETATM   11  H2  UNL     1       4.232   0.119  -0.673  1.00  0.00           H  
HETATM   12  H3  UNL     1       3.414   1.547   0.135  1.00  0.00           H  
HETATM   13  H4  UNL     1       1.175  -1.485   0.867  1.00  0.00           H  
HETATM   14  H5  UNL     1       0.498   0.201  -1.542  1.00  0.00           H  
HETATM   15  H6  UNL     1       0.343  -1.541  -1.212  1.00  0.00           H  
HETATM   16  H7  UNL     1      -0.608   0.820   0.551  1.00  0.00           H  
HETATM   17  H8  UNL     1      -0.794  -0.905   0.994  1.00  0.00           H  
HETATM   18  H9  UNL     1      -1.737   0.528  -1.577  1.00  0.00           H  
HETATM   19  H10 UNL     1      -1.871  -1.231  -1.353  1.00  0.00           H  
HETATM   20  H11 UNL     1      -3.371  -0.740   0.666  1.00  0.00           H  
HETATM   21  H12 UNL     1      -3.961  -0.087  -0.873  1.00  0.00           H  
HETATM   22  H13 UNL     1      -2.779   1.987  -0.241  1.00  0.00           H  
HETATM   23  H14 UNL     1      -2.463   1.287   1.262  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    3    4
CONECT    4    5   13
CONECT    5    6   14   15
CONECT    6    7   16   17
CONECT    7    8   18   19
CONECT    8    9   20   21
CONECT    9   22   23
END
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SMILES for NP0000452 (N-Acetylputrescine)

CC(=O)NCCCCN
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INCHI for NP0000452 (N-Acetylputrescine)

InChI=1S/C6H14N2O/c1-6(9)8-5-3-2-4-7/h2-5,7H2,1H3,(H,8,9)
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View in JSmol
Synonyms
ValueSource
AcetylputrescineHMDB
MonoacetylputrescineHMDB
N-(4-Aminobutyl)acetamideHMDB
N-Acetylputrescine monohydrochlorideHMDB
Chemical FormulaC6H14N2O
Average Mass130.1882 Da
Monoisotopic Mass130.11061 Da
IUPAC NameN-(4-aminobutyl)acetamide
Traditional Nameacetylputrescine
CAS Registry Number18233-70-0
SMILES
CC(=O)NCCCCN
InChI Identifier
InChI=1S/C6H14N2O/c1-6(9)8-5-3-2-4-7/h2-5,7H2,1H3,(H,8,9)
InChI KeyKLZGKIDSEJWEDW-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
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
Chlamydomonas reinhardtiiLOTUS Database
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Remijia peruvianaKNApSAcK Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trypanosoma bruceiLOTUS Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboximidic acids and derivatives
Sub ClassCarboximidic acids
Direct ParentCarboximidic acids
Alternative Parents
Substituents
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility141 g/LALOGPS
logP-0.84ALOGPS
logP-1ChemAxon
logS0.04ALOGPS
pKa (Strongest Acidic)16.48ChemAxon
pKa (Strongest Basic)9.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.12 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity36.82 m³·mol⁻¹ChemAxon
Polarizability15.28 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002064
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022827
KNApSAcK IDC00052356
Chemspider ID109095
KEGG Compound IDC02714
BioCyc IDCPD-569
BiGG ID1445791
Wikipedia LinkNot Available
METLIN ID3252
PubChem Compound122356
PDB IDNot Available
ChEBI ID17768
Good Scents IDNot Available
References
General References
  1. Loser C, Folsch UR, Paprotny C, Creutzfeldt W: Polyamines in colorectal cancer. Evaluation of polyamine concentrations in the colon tissue, serum, and urine of 50 patients with colorectal cancer. Cancer. 1990 Feb 15;65(4):958-66. [PubMed:2297664 ]
  2. Abdel-Monem MM, Ohno K: Polyamine metabolism I: Synthesis of dansyl derivatives of N-(monoaminoalkyl)- and N-(polyaminoalkyl)acetamides and elucidation in urine of a cancer patient. J Pharm Sci. 1977 Aug;66(8):1089-94. [PubMed:197226 ]
  3. Hiramatsu K, Kamei S, Sugimoto M, Kinoshita K, Iwasaki K, Kawakita M: An improved method of determining free and acetylated polyamines by HPLC involving an enzyme reactor and an electrochemical detector. J Biochem. 1994 Mar;115(3):584-9. [PubMed:8056776 ]
  4. Nguyen AQ, Schneider J, Reddy GK, Wendisch VF: Fermentative production of the diamine putrescine: system metabolic engineering of corynebacterium glutamicum. Metabolites. 2015 Apr 24;5(2):211-31. doi: 10.3390/metabo5020211. [PubMed:25919117 ]