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Showing NP-Card for Aminopropylcadaverine (NP0091972)

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Record Information
Version1.0
Created at2022-05-11 18:53:33 UTC
Updated at2022-05-11 18:53:33 UTC
NP-MRD IDNP0091972
Secondary Accession NumbersNone
Natural Product Identification
Common NameAminopropylcadaverine
DescriptionAminopropylcadaverine, also known as 3-apcad, belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Aminopropylcadaverine is a very strong basic compound (based on its pKa). Aminopropylcadaverine exists in all living organisms, ranging from bacteria to humans. It was first documented in 1986 (PMID: 3514574). A polyazaalkane that is the 1,4,11-triaza derivative of undecane (PMID: 12121990) (PMID: 14982633) (PMID: 2689281) (PMID: 3122732).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0091972 (Aminopropylcadaverine)


  Mrv0541 02241203492D          

 11 10  0  0  0  0            999 V2000
   14.9516  -10.2273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6661   -9.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3806  -10.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0951   -9.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8096  -10.2273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5241   -9.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2386  -10.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9530   -9.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6676  -10.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3820   -9.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0966  -10.2273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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
M  END
Download

3D MOL for NP0091972 (Aminopropylcadaverine)

     RDKit          3D

 32 31  0  0  0  0  0  0  0  0999 V2000
   -5.7007    0.0006    1.0740 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3666    0.5113    1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4199   -0.1282    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9900    0.3343    0.5998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1414   -0.3690   -0.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3209    0.0528   -0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312   -0.6627   -1.3813 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3972   -0.2088   -1.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2469   -0.5805   -0.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6665   -0.0315   -0.4228 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4186   -0.4479    0.7384 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0654    0.6491    0.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6070   -0.9285    0.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3634    1.6205    1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0734    0.3191    2.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7263    0.2223   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4620   -1.2165    0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6482    0.0411    1.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9061    1.4201    0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2718   -1.4437   -0.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5130   -0.0351   -1.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6755   -0.3347    0.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4248    1.1456   -0.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6239   -0.5130   -2.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8540   -0.6566   -2.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4387    0.9073   -1.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8762   -0.1983    0.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3249   -1.6917   -0.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5467    1.0820   -0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072   -0.3249   -1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9638   -1.2920    1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3384    0.3144    1.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
M  END
Download

3D SDF for NP0091972 (Aminopropylcadaverine)


  Mrv0541 02241203492D          

 11 10  0  0  0  0            999 V2000
   14.9516  -10.2273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6661   -9.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3806  -10.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0951   -9.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8096  -10.2273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5241   -9.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2386  -10.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9530   -9.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6676  -10.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3820   -9.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0966  -10.2273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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
M  END
> <DATABASE_ID>
NP0091972

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCCCCNCCCN

> <INCHI_IDENTIFIER>
InChI=1S/C8H21N3/c9-5-2-1-3-7-11-8-4-6-10/h11H,1-10H2

> <INCHI_KEY>
QZBYOYPROVGOGE-UHFFFAOYSA-N

> <FORMULA>
C8H21N3

> <MOLECULAR_WEIGHT>
159.2724

> <EXACT_MASS>
159.173547687

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.904693787528277

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5-aminopentyl)(3-aminopropyl)amine

> <ALOGPS_LOGP>
-0.09

> <JCHEM_LOGP>
-0.7049952750000001

> <ALOGPS_LOGS>
-1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
3

> <JCHEM_PKA_STRONGEST_BASIC>
10.89817484046326

> <JCHEM_POLAR_SURFACE_AREA>
64.07

> <JCHEM_REFRACTIVITY>
49.5694

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aminopropylcadaverine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0091972 (Aminopropylcadaverine)

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PDB for NP0091972 (Aminopropylcadaverine)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      27.910 -19.091   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      29.243 -18.321   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.577 -19.091   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.911 -18.321   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      33.245 -19.091   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      34.578 -18.321   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      35.912 -19.091   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      37.246 -18.321   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      38.580 -19.091   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      39.913 -18.321   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      41.247 -19.091   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0091972 (Aminopropylcadaverine)
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SMILES for NP0091972 (Aminopropylcadaverine)
NCCCCCNCCCN
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INCHI for NP0091972 (Aminopropylcadaverine)
InChI=1S/C8H21N3/c9-5-2-1-3-7-11-8-4-6-10/h11H,1-10H2
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View in JSmol
Synonyms
ValueSource
3-ApcadChEBI
N-(3-Aminopropyl)-1,5-pentanediamineChEBI
N-(3-Aminopropyl)cadaverineChEBI
N-3-Aminopropyl-1,5-diaminopentaneChEBI
Chemical FormulaC8H21N3
Average Mass159.2724 Da
Monoisotopic Mass159.17355 Da
IUPAC Name(5-aminopentyl)(3-aminopropyl)amine
Traditional Nameaminopropylcadaverine
CAS Registry NumberNot Available
SMILES
NCCCCCNCCCN
InChI Identifier
InChI=1S/C8H21N3/c9-5-2-1-3-7-11-8-4-6-10/h11H,1-10H2
InChI KeyQZBYOYPROVGOGE-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 dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.
KingdomOrganic compounds  
Super ClassOrganic nitrogen compounds  
ClassOrganonitrogen compounds  
Sub ClassAmines  
Direct ParentDialkylamines  
Alternative Parents
Substituents
  • Secondary aliphatic amine
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary amine
    • 

  • Primary aliphatic amine
    • 

  • 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
logP-0.09ALOGPS
logP-0.7ChemAxon
logS-1.1ALOGPS
pKa (Strongest Basic)10.9ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area64.07 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity49.57 m³·mol⁻¹ChemAxon
Polarizability20.9 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012189  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028841  
KNApSAcK IDNot Available
Chemspider ID58969  
KEGG Compound IDC16565  
BioCyc IDCPD0-1065  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound65523  
PDB IDNot Available
ChEBI ID64860  
Good Scents IDNot Available
References
General References
  1. Oza SL, Tetaud E, Ariyanayagam MR, Warnon SS, Fairlamb AH: A single enzyme catalyses formation of Trypanothione from glutathione and spermidine in Trypanosoma cruzi. J Biol Chem. 2002 Sep 27;277(39):35853-61. doi: 10.1074/jbc.M204403200. Epub 2002  Jul 16. [PubMed:12121990  ] 
  2. Soksawatmaekhin W, Kuraishi A, Sakata K, Kashiwagi K, Igarashi K: Excretion and uptake of cadaverine by CadB and its physiological functions in Escherichia coli. Mol Microbiol. 2004 Mar;51(5):1401-12. doi: 10.1046/j.1365-2958.2003.03913.x. [PubMed:14982633  ] 
  3. Hamana K, Matsuzaki S, Hosaka K, Yamashita S: Interconversion of polyamines in wild-type strains and mutants of yeasts and the effects of polyamines on their growth. FEMS Microbiol Lett. 1989 Oct 1;52(1-2):231-6. doi: 10.1016/0378-1097(89)90202-4. [PubMed:2689281  ] 
  4. Alhonen-Hongisto L, Hirvonen A, Sinervirta R, Janne J: Cadaverine supplementation during a chronic exposure to difluoromethylornithine allows an overexpression, but prevents gene amplification, of ornithine decarboxylase in L1210 mouse leukaemia cells. Biochem J. 1987 Nov 1;247(3):651-5. doi: 10.1042/bj2470651. [PubMed:3122732  ] 
  5. Igarashi K, Kashiwagi K, Hamasaki H, Miura A, Kakegawa T, Hirose S, Matsuzaki S: Formation of a compensatory polyamine by Escherichia coli polyamine-requiring mutants during growth in the absence of polyamines. J Bacteriol. 1986 Apr;166(1):128-34. doi: 10.1128/jb.166.1.128-134.1986. [PubMed:3514574  ]