NP-MRD: Showing NP-Card for Caffeoylferuloylspermidine (NP0047655)

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Record Information

Version

2.0

Created at

2022-03-17 20:43:45 UTC

Updated at

2022-03-17 20:43:46 UTC

NP-MRD ID

NP0047655

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Caffeoylferuloylspermidine

Description

Caffeoylferuloylspermidine belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. Caffeoylferuloylspermidine is a very strong basic compound (based on its pKa). Outside of the human body, Caffeoylferuloylspermidine has been detected, but not quantified in, common hazelnuts and nuts. This could make caffeoylferuloylspermidine a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 08271307242D          

 35 36  0  0  0  0            999 V2000
   -7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.0125    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
    3.5724    3.7125    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
  3  2  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 13  2  1  0  0  0  0
 14  4  1  0  0  0  0
 15  3  1  0  0  0  0
 16  4  1  0  0  0  0
 19  5  1  0  0  0  0
 19  7  1  0  0  0  0
 19 17  2  0  0  0  0
 20  6  1  0  0  0  0
 20  8  1  0  0  0  0
 20 18  2  0  0  0  0
 21  9  1  0  0  0  0
 22 10  1  0  0  0  0
 23 17  1  0  0  0  0
 23 21  2  0  0  0  0
 24 18  1  0  0  0  0
 24 22  2  0  0  0  0
 25 12  1  0  0  0  0
 26 11  1  0  0  0  0
 27 13  1  0  0  0  0
 27 14  1  0  0  0  0
 28 15  1  0  0  0  0
 28 25  1  0  0  0  0
 29 16  1  0  0  0  0
 29 26  1  0  0  0  0
 30 21  1  0  0  0  0
 31 22  1  0  0  0  0
 32 23  1  0  0  0  0
 33 25  2  0  0  0  0
 34 26  2  0  0  0  0
 35  1  1  0  0  0  0
 35 24  1  0  0  0  0
M  END


  Mrv0541 08271307242D          

 35 36  0  0  0  0            999 V2000
   -7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.0125    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
    3.5724    3.7125    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
  3  2  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 13  2  1  0  0  0  0
 14  4  1  0  0  0  0
 15  3  1  0  0  0  0
 16  4  1  0  0  0  0
 19  5  1  0  0  0  0
 19  7  1  0  0  0  0
 19 17  2  0  0  0  0
 20  6  1  0  0  0  0
 20  8  1  0  0  0  0
 20 18  2  0  0  0  0
 21  9  1  0  0  0  0
 22 10  1  0  0  0  0
 23 17  1  0  0  0  0
 23 21  2  0  0  0  0
 24 18  1  0  0  0  0
 24 22  2  0  0  0  0
 25 12  1  0  0  0  0
 26 11  1  0  0  0  0
 27 13  1  0  0  0  0
 27 14  1  0  0  0  0
 28 15  1  0  0  0  0
 28 25  1  0  0  0  0
 29 16  1  0  0  0  0
 29 26  1  0  0  0  0
 30 21  1  0  0  0  0
 31 22  1  0  0  0  0
 32 23  1  0  0  0  0
 33 25  2  0  0  0  0
 34 26  2  0  0  0  0
 35  1  1  0  0  0  0
 35 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047655

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(\C=C\C(=O)NCCCCNCCCNC(=O)\C=C\C2=CC(O)=C(O)C=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H33N3O6/c1-35-24-18-20(6-10-22(24)31)8-12-25(33)28-15-3-2-13-27-14-4-16-29-26(34)11-7-19-5-9-21(30)23(32)17-19/h5-12,17-18,27,30-32H,2-4,13-16H2,1H3,(H,28,33)(H,29,34)/b11-7+,12-8+

> <INCHI_KEY>
YUUGXIVVDZSRNR-MKICQXMISA-N

> <FORMULA>
C26H33N3O6

> <MOLECULAR_WEIGHT>
483.5567

> <EXACT_MASS>
483.236935803

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
55.17105173712231

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-(3,4-dihydroxyphenyl)-N-[3-({4-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}amino)propyl]prop-2-enamide

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
0.9391313455684137

> <ALOGPS_LOGS>
-5.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.388773325584513

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.800866001943183

> <JCHEM_PKA_STRONGEST_BASIC>
9.098705988085937

> <JCHEM_POLAR_SURFACE_AREA>
140.14999999999998

> <JCHEM_REFRACTIVITY>
137.0943

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.44e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(3,4-dihydroxyphenyl)-N-[3-({4-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}amino)propyl]prop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-AUG-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-AUG-13         0                                  
HETATM    1  C   UNK     0     -14.671   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003   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       9.336   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      13.337   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       8.002   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      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -12.003   6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -12.003   8.470   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337  10.780   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -14.671   6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.003  11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -13.337   6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       0.000   9.240   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0      -6.668   8.470   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0       5.335   9.240   0.000  0.00  0.00           N+0
HETATM   30  O   UNK     0      14.671  11.550   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0     -16.004   6.160   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      12.003  13.090   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -8.002  10.780   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0     -13.337   4.620   0.000  0.00  0.00           O+0
CONECT    1   35                                                            
CONECT    2    3   13                                                       
CONECT    3    2   15                                                       
CONECT    4   14   16                                                       
CONECT    5    9   19                                                       
CONECT    6   10   20                                                       
CONECT    7   11   19                                                       
CONECT    8   12   20                                                       
CONECT    9    5   21                                                       
CONECT   10    6   22                                                       
CONECT   11    7   26                                                       
CONECT   12    8   25                                                       
CONECT   13    2   27                                                       
CONECT   14    4   27                                                       
CONECT   15    3   28                                                       
CONECT   16    4   29                                                       
CONECT   17   19   23                                                       
CONECT   18   20   24                                                       
CONECT   19    5    7   17                                                  
CONECT   20    6    8   18                                                  
CONECT   21    9   23   30                                                  
CONECT   22   10   24   31                                                  
CONECT   23   17   21   32                                                  
CONECT   24   18   22   35                                                  
CONECT   25   12   28   33                                                  
CONECT   26   11   29   34                                                  
CONECT   27   13   14                                                       
CONECT   28   15   25                                                       
CONECT   29   16   26                                                       
CONECT   30   21                                                            
CONECT   31   22                                                            
CONECT   32   23                                                            
CONECT   33   25                                                            
CONECT   34   26                                                            
CONECT   35    1   24                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Value	Source
(2E)-3-(3,4-Dihydroxyphenyl)-N-{3-[(4-{[(2E)-1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-ylidene]amino}butyl)amino]propyl}prop-2-enimidate	HMDB
N1-Caffeoyl-N10-feruloylspermidine	HMDB
Caffeoylferuloylspermidine	HMDB

Chemical Formula

C₂₆H₃₃N₃O₆

Average Mass

483.5567 Da

Monoisotopic Mass

483.23694 Da

IUPAC Name

(2E)-3-(3,4-dihydroxyphenyl)-N-[3-({4-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}amino)propyl]prop-2-enamide

Traditional Name

(2E)-3-(3,4-dihydroxyphenyl)-N-[3-({4-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}amino)propyl]prop-2-enamide

CAS Registry Number

124935-81-5

SMILES

COC1=C(O)C=CC(\C=C\C(=O)NCCCCNCCCNC(=O)\C=C\C2=CC(O)=C(O)C=C2)=C1

InChI Identifier

InChI=1S/C26H33N3O6/c1-35-24-18-20(6-10-22(24)31)8-12-25(33)28-15-3-2-13-27-14-4-16-29-26(34)11-7-19-5-9-21(30)23(32)17-19/h5-12,17-18,27,30-32H,2-4,13-16H2,1H3,(H,28,33)(H,29,34)/b11-7+,12-8+

InChI Key

YUUGXIVVDZSRNR-MKICQXMISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Corylus avellana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids and derivatives

Alternative Parents

Substituents

Cinnamic acid amide
Hydroxycinnamic acid or derivatives
Methoxyphenol
Phenoxy compound
Catechol
Phenol ether
Styrene
Methoxybenzene
Anisole
Alkyl aryl ether
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Secondary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Secondary amine
Ether
Carboxylic acid derivative
Secondary aliphatic amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	2.29	ALOGPS
logP	0.94	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	9.8	ChemAxon
pKa (Strongest Basic)	9.1	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	140.15 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	137.09 m³·mol⁻¹	ChemAxon
Polarizability	55.17 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

External Links

HMDB ID

HMDB0033470

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011512

KNApSAcK ID

Not Available

Chemspider ID

30777008

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751431

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Caffeoylferuloylspermidine (NP0047655)

MOL for NP0047655 (Caffeoylferuloylspermidine)

3D MOL for NP0047655 (Caffeoylferuloylspermidine)

3D SDF for NP0047655 (Caffeoylferuloylspermidine)

3D-SDF for NP0047655 (Caffeoylferuloylspermidine)

PDB for NP0047655 (Caffeoylferuloylspermidine)

3D PDB for NP0047655 (Caffeoylferuloylspermidine)

SMILES for NP0047655 (Caffeoylferuloylspermidine)

INCHI for NP0047655 (Caffeoylferuloylspermidine)

Structure for NP0047655 (Caffeoylferuloylspermidine)

3D Structure for NP0047655 (Caffeoylferuloylspermidine)