NP-MRD: Showing NP-Card for 1,14-Bis(dihydrocaffeoyl)spermine (NP0070017)

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Record Information

Version

2.0

Created at

2022-04-28 15:18:06 UTC

Updated at

2022-04-28 15:18:06 UTC

NP-MRD ID

NP0070017

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,14-Bis(dihydrocaffeoyl)spermine

Description

Kukoamine A belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 1,14-Bis(dihydrocaffeoyl)spermine is found in ASolanum tuberosum, Lychium chinense, Lycium chinense and Solanum tuberosum . Kukoamine A is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061305122D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 05061305122D          

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    9.2881    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  1  1  0  0  0  0
 14  2  1  0  0  0  0
 15  3  1  0  0  0  0
 16  4  1  0  0  0  0
 17  3  1  0  0  0  0
 18  4  1  0  0  0  0
 21  5  1  0  0  0  0
 21  7  1  0  0  0  0
 21 19  2  0  0  0  0
 22  6  1  0  0  0  0
 22  8  1  0  0  0  0
 22 20  2  0  0  0  0
 23  9  1  0  0  0  0
 24 10  1  0  0  0  0
 25 19  1  0  0  0  0
 25 23  2  0  0  0  0
 26 20  1  0  0  0  0
 26 24  2  0  0  0  0
 27 11  1  0  0  0  0
 28 12  1  0  0  0  0
 29 13  1  0  0  0  0
 29 15  1  0  0  0  0
 30 14  1  0  0  0  0
 30 16  1  0  0  0  0
 31 17  1  0  0  0  0
 31 27  2  0  0  0  0
 32 18  1  0  0  0  0
 32 28  2  0  0  0  0
 33 23  1  0  0  0  0
 34 24  1  0  0  0  0
 35 25  1  0  0  0  0
 36 26  1  0  0  0  0
 37 27  1  0  0  0  0
 38 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0070017

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O\C(CCC1=CC(O)=C(O)C=C1)=N/CCCNCCCCNCCC\N=C(/O)CCC1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H42N4O6/c33-23-9-5-21(19-25(23)35)7-11-27(37)31-17-3-15-29-13-1-2-14-30-16-4-18-32-28(38)12-8-22-6-10-24(34)26(36)20-22/h5-6,9-10,19-20,29-30,33-36H,1-4,7-8,11-18H2,(H,31,37)(H,32,38)

> <INCHI_KEY>
IOLDDENZPBFBHV-UHFFFAOYSA-N

> <FORMULA>
C28H42N4O6

> <MOLECULAR_WEIGHT>
530.6563

> <EXACT_MASS>
530.310435096

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
62.1288355308615

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(Z)-3-(3,4-dihydroxyphenyl)-N-(3-{[4-({3-[(Z)-[3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino]propyl}amino)butyl]amino}propyl)propimidic acid

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
-1.6893248818899154

> <ALOGPS_LOGS>
-4.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
4

> <JCHEM_PKA>
7.648368417977821

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.056652001570929

> <JCHEM_PKA_STRONGEST_BASIC>
13.04490368540411

> <JCHEM_POLAR_SURFACE_AREA>
170.16

> <JCHEM_REFRACTIVITY>
149.0586

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(Z)-3-(3,4-dihydroxyphenyl)-N-(3-{[4-({3-[(Z)-[3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino]propyl}amino)butyl]amino}propyl)propimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.338   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -13.337   9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.671   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.669   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.672   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -14.671   8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.337   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.004  10.780   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -12.003   6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.004   9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -12.003   8.470   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.672  10.780   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -14.671   6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.338  11.550   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -13.337   6.160   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       5.335   9.240   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0      -1.334   8.470   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0      10.669   9.240   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0      -6.668   8.470   0.000  0.00  0.00           N+0
HETATM   33  O   UNK     0      20.005  11.550   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0     -16.004   6.160   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      17.338  13.090   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0     -13.337   4.620   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -8.002  10.780   0.000  0.00  0.00           O+0
CONECT    1    2   13                                                       
CONECT    2    1   14                                                       
CONECT    3   15   17                                                       
CONECT    4   16   18                                                       
CONECT    5    9   21                                                       
CONECT    6   10   22                                                       
CONECT    7   11   21                                                       
CONECT    8   12   22                                                       
CONECT    9    5   23                                                       
CONECT   10    6   24                                                       
CONECT   11    7   27                                                       
CONECT   12    8   28                                                       
CONECT   13    1   29                                                       
CONECT   14    2   30                                                       
CONECT   15    3   29                                                       
CONECT   16    4   30                                                       
CONECT   17    3   31                                                       
CONECT   18    4   32                                                       
CONECT   19   21   25                                                       
CONECT   20   22   26                                                       
CONECT   21    5    7   19                                                  
CONECT   22    6    8   20                                                  
CONECT   23    9   25   33                                                  
CONECT   24   10   26   34                                                  
CONECT   25   19   23   35                                                  
CONECT   26   20   24   36                                                  
CONECT   27   11   31   37                                                  
CONECT   28   12   32   38                                                  
CONECT   29   13   15                                                       
CONECT   30   14   16                                                       
CONECT   31   17   27                                                       
CONECT   32   18   28                                                       
CONECT   33   23                                                            
CONECT   34   24                                                            
CONECT   35   25                                                            
CONECT   36   26                                                            
CONECT   37   27                                                            
CONECT   38   28                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

View in JSmol

Synonyms

Value	Source
1,14-Bis(dihydrocaffeoyl)spermine	HMDB
N(1),N(12)-Bis(dihydrocaffeoyl)spermine	MeSH

Chemical Formula

C₂₈H₄₂N₄O₆

Average Mass

530.6563 Da

Monoisotopic Mass

530.31044 Da

IUPAC Name

(Z)-3-(3,4-dihydroxyphenyl)-N-(3-{[4-({3-[(Z)-[3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino]propyl}amino)butyl]amino}propyl)propimidic acid

Traditional Name

(Z)-3-(3,4-dihydroxyphenyl)-N-(3-{[4-({3-[(Z)-[3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino]propyl}amino)butyl]amino}propyl)propimidic acid

CAS Registry Number

Not Available

SMILES

O\C(CCC1=CC(O)=C(O)C=C1)=N/CCCNCCCCNCCC\N=C(/O)CCC1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C28H42N4O6/c33-23-9-5-21(19-25(23)35)7-11-27(37)31-17-3-15-29-13-1-2-14-30-16-4-18-32-28(38)12-8-22-6-10-24(34)26(36)20-22/h5-6,9-10,19-20,29-30,33-36H,1-4,7-8,11-18H2,(H,31,37)(H,32,38)

InChI Key

IOLDDENZPBFBHV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
ASolanum tuberosum	-	KNApSAcK
Lychium chinense	-	KNApSAcK
Lycium chinense	Plant	KNApSAcK
Solanum tuberosum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Fatty acyl
Fatty amide
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Secondary amine
Secondary aliphatic amine
Amine
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

amine (CHEBI:81220 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.24	ALOGPS
logP	-1.7	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.06	ChemAxon
pKa (Strongest Basic)	13.04	ChemAxon
Physiological Charge	4	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	170.16 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	149.06 m³·mol⁻¹	ChemAxon
Polarizability	62.13 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon