NP-MRD: Showing NP-Card for n-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid (NP0204033)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 23:37:56 UTC

Updated at

2022-09-04 23:37:56 UTC

NP-MRD ID

NP0204033

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid

Description

N-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)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-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid is found in Iochroma cyaneum, Nicotiana tabacum, Selaginella moellendorffii and Solanum tuberosum. N-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
   -6.8892    0.6787    0.1947 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4335    0.7242    0.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8036   -0.2944   -0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2968   -0.3532   -0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6496    0.9591   -0.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2380    0.8987   -0.6309 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4767   -0.0621   -0.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9056   -1.3603   -0.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9799    0.1805   -0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073   -0.7750    0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2430   -0.5904    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0861   -1.6614    0.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4555   -1.5342    0.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0583   -0.3249    0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4477   -0.1721    0.2092 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2778    0.7353   -0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8242    1.9803   -0.4676 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8895    0.5933   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0551    1.0437   -0.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1312   -0.3512    0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0653    1.7479    0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1922    0.5030    1.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1741   -1.3026   -0.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1025   -0.1416   -1.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0173   -0.6436    0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9449   -1.1324   -1.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9084    1.2741   -1.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0528    1.7734   -0.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6028   -1.7437    0.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3228    1.1554   -0.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4166   -1.7599    0.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6412   -2.6255    0.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0931   -2.3741    0.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8725    0.7205   -0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2378    2.7653   -0.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2864    1.4689   -0.4936 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 18  2  0
 18 16  1  0
 16 17  1  0
 16 14  2  0
 14 15  1  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 18 36  1  0
 17 35  1  0
 15 34  1  0
 13 33  1  0
 12 32  1  0
M  END


  Mrv1652308231919332D          

 18 18  0  0  0  0            999 V2000
   -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
   -7.1447    4.9500    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
   -7.8592    4.5375    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
   -2.8579    4.9500    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
   -6.4302    4.5375    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
   -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
    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
   -8.5737    3.3000    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
   -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
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  9  2  0  0  0  0
 11  5  1  0  0  0  0
 12  9  1  0  0  0  0
 12 11  2  0  0  0  0
  6 13  1  4  0  0  0
 14  7  1  0  0  0  0
 15  8  1  4  0  0  0
 15 13  2  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204033

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCCCN=C(O)C=CC1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H18N2O3/c14-7-1-2-8-15-13(18)6-4-10-3-5-11(16)12(17)9-10/h3-6,9,16-17H,1-2,7-8,14H2,(H,15,18)

> <INCHI_KEY>
KTZNZCYTXQYEHT-UHFFFAOYSA-N

> <FORMULA>
C13H18N2O3

> <MOLECULAR_WEIGHT>
250.298

> <EXACT_MASS>
250.131742448

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.116787902587337

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid

> <ALOGPS_LOGP>
0.63

> <JCHEM_LOGP>
-0.7463086238300551

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
9.229545346127157

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.629756219306289

> <JCHEM_PKA_STRONGEST_BASIC>
12.692453214693018

> <JCHEM_POLAR_SURFACE_AREA>
99.07000000000001

> <JCHEM_REFRACTIVITY>
71.72210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-AUG-19         0                                  
HETATM    1  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -13.337   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.669   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -14.671   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -12.003   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -12.003   8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -14.671   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -13.337   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.000   9.240   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      -6.668   8.470   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0     -16.004   6.160   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0     -13.337   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -8.002  10.780   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    8                                                       
CONECT    3    5   10                                                       
CONECT    4    6   10                                                       
CONECT    5    3   11                                                       
CONECT    6    4   13                                                       
CONECT    7    1   14                                                       
CONECT    8    2   15                                                       
CONECT    9   10   12                                                       
CONECT   10    3    4    9                                                  
CONECT   11    5   12   16                                                  
CONECT   12    9   11   17                                                  
CONECT   13    6   15   18                                                  
CONECT   14    7                                                            
CONECT   15    8   13                                                       
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
N-(4-Aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidate	Generator

Chemical Formula

C₁₃H₁₈N₂O₃

Average Mass

250.2980 Da

Monoisotopic Mass

250.13174 Da

IUPAC Name

N-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid

Traditional Name

N-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid

CAS Registry Number

Not Available

SMILES

NCCCCN=C(O)C=CC1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C13H18N2O3/c14-7-1-2-8-15-13(18)6-4-10-3-5-11(16)12(17)9-10/h3-6,9,16-17H,1-2,7-8,14H2,(H,15,18)

InChI Key

KTZNZCYTXQYEHT-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
Iochroma cyaneum	LOTUS Database	35616633
Nicotiana tabacum	LOTUS Database	35616633
Selaginella moellendorffii	LOTUS Database	35616633
Solanum tuberosum	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
Styrene
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Amine
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
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	0.63	ALOGPS
logP	-0.75	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.63	ChemAxon
pKa (Strongest Basic)	12.69	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.07 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	71.72 m³·mol⁻¹	ChemAxon
Polarizability	28.12 Å³	ChemAxon
Number of Rings	1	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

HMDB0139613

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB093087

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-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid (NP0204033)

MOL for NP0204033 (n-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid)

3D MOL for NP0204033 (n-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid)

3D SDF for NP0204033 (n-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid)

3D-SDF for NP0204033 (n-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid)

PDB for NP0204033 (n-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid)

3D PDB for NP0204033 (n-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid)

SMILES for NP0204033 (n-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid)

INCHI for NP0204033 (n-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid)

Structure for NP0204033 (n-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid)

3D Structure for NP0204033 (n-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enimidic acid)