NP-MRD: Showing NP-Card for n-{4-[n-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid (NP0326874)

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Record Information

Version

1.0

Created at

2022-09-12 08:53:52 UTC

Updated at

2022-09-12 08:53:53 UTC

NP-MRD ID

NP0326874

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-{4-[n-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid

Description

N-{4-[N-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid 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. n-{4-[n-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid is found in Betula pendula. N-{4-[N-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241512022D          

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M  END

     RDKit          3D

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  Mrv1533004241512022D          

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 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  2  0  0  0  0
 24 32  1  0  0  0  0
  5 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0326874

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C=CC(=O)NCCCCN(CCCN)C(=O)C=CC2=CC=C(O)C(OC)=C2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H35N3O6/c1-35-24-18-20(6-10-22(24)31)8-12-26(33)29-15-3-4-16-30(17-5-14-28)27(34)13-9-21-7-11-23(32)25(19-21)36-2/h6-13,18-19,31-32H,3-5,14-17,28H2,1-2H3,(H,29,33)

> <INCHI_KEY>
KVWGMVKLGMSMQY-UHFFFAOYSA-N

> <FORMULA>
C27H35N3O6

> <MOLECULAR_WEIGHT>
497.592

> <EXACT_MASS>
497.252585859

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
55.535231588859695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{4-[N-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide

> <ALOGPS_LOGP>
2.97

> <JCHEM_LOGP>
1.2105843394527063

> <ALOGPS_LOGS>
-5.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.32881148978351

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.848285383323505

> <JCHEM_PKA_STRONGEST_BASIC>
9.367063255335713

> <JCHEM_POLAR_SURFACE_AREA>
134.35

> <JCHEM_REFRACTIVITY>
141.6987

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-{4-[N-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -2.909 -10.677   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.397 -10.386   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.389 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.123 -11.259   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.132 -12.423   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.644 -12.132   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.652 -13.296   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.164 -13.005   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.172 -14.169   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       6.668 -11.550   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       8.181 -11.259   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.685  -9.804   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.197  -9.513   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.701  -8.058   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      12.213  -7.767   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      13.221  -8.931   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.717 -10.386   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.726 -11.550   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      13.221 -13.005   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      12.717  -6.311   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.709  -5.147   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.230  -6.020   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.734  -4.565   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.246  -4.274   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.750  -2.819   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.262  -2.528   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.270  -3.692   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      20.783  -3.401   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      18.766  -5.147   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      19.775  -6.311   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      19.270  -7.767   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.254  -5.438   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.628 -13.878   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.115 -14.169   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.893 -13.005   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.405 -13.296   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   33                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   15   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   24                                                       
CONECT   33    5   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    3   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Value	Source
N-{4-[N-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidate	Generator

Chemical Formula

C₂₇H₃₅N₃O₆

Average Mass

497.5920 Da

Monoisotopic Mass

497.25259 Da

IUPAC Name

N-{4-[N-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide

Traditional Name

N-{4-[N-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide

CAS Registry Number

Not Available

SMILES

COC1=CC(C=CC(=O)NCCCCN(CCCN)C(=O)C=CC2=CC=C(O)C(OC)=C2)=CC=C1O

InChI Identifier

InChI=1S/C27H35N3O6/c1-35-24-18-20(6-10-22(24)31)8-12-26(33)29-15-3-4-16-30(17-5-14-28)27(34)13-9-21-7-11-23(32)25(19-21)36-2/h6-13,18-19,31-32H,3-5,14-17,28H2,1-2H3,(H,29,33)

InChI Key

KVWGMVKLGMSMQY-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Betula pendula	LOTUS Database	35616633

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
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Ether
Carboxylic acid derivative
Primary aliphatic amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Amine
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Primary 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	2.97	ALOGPS
logP	1.21	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	9.85	ChemAxon
pKa (Strongest Basic)	9.37	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.35 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	141.7 m³·mol⁻¹	ChemAxon
Polarizability	55.54 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-{4-[n-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid (NP0326874)

MOL for NP0326874 (n-{4-[n-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid)

3D MOL for NP0326874 (n-{4-[n-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid)

3D SDF for NP0326874 (n-{4-[n-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid)

3D-SDF for NP0326874 (n-{4-[n-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid)

PDB for NP0326874 (n-{4-[n-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid)

3D PDB for NP0326874 (n-{4-[n-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid)

SMILES for NP0326874 (n-{4-[n-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid)

INCHI for NP0326874 (n-{4-[n-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid)

Structure for NP0326874 (n-{4-[n-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid)

3D Structure for NP0326874 (n-{4-[n-(3-aminopropyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]butyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid)