NP-MRD: Showing NP-Card for Sinapoylputrescine (NP0336255)

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Record Information

Version

2.0

Created at

2024-09-11 05:24:59 UTC

Updated at

2024-09-11 05:24:59 UTC

NP-MRD ID

NP0336255

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sinapoylputrescine

Description

Sinapoylputrescine 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. Sinapoylputrescine is a very strong basic compound (based on its pKa). Outside of the human body, Sinapoylputrescine has been detected, but not quantified in, fruits. This could make sinapoylputrescine a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241211262D          

 21 21  0  0  0  0            999 V2000
   -0.0004    2.0927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6563    2.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3951    2.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4772    1.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2159    0.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2159    0.0406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2159   -1.6824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2159   -2.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4772    1.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7384    0.8615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7384   -0.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0817   -0.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9025    0.2048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4772   -0.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3951   -1.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6563   -1.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0817   -1.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7384   -1.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4772   -1.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4772   -0.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2159    0.0406    0.0000 O   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 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 19  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 20  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336255

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C/C(=O)NCCCCN)=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22N2O4/c1-20-12-9-11(10-13(21-2)15(12)19)5-6-14(18)17-8-4-3-7-16/h5-6,9-10,19H,3-4,7-8,16H2,1-2H3,(H,17,18)/b6-5-

> <INCHI_KEY>
ZYERUQAOCQZPJW-WAYWQWQTSA-N

> <FORMULA>
C15H22N2O4

> <MOLECULAR_WEIGHT>
294.3462

> <EXACT_MASS>
294.157957202

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.44256963677573

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-N-(4-aminobutyl)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enamide

> <ALOGPS_LOGP>
0.95

> <JCHEM_LOGP>
-0.11846795402318908

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.706235694109104

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.210889657369318

> <JCHEM_PKA_STRONGEST_BASIC>
10.002442023684862

> <JCHEM_POLAR_SURFACE_AREA>
93.81000000000002

> <JCHEM_REFRACTIVITY>
82.1459

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-N-(4-aminobutyl)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

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      -0.001   3.906   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.225   4.673   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.604   3.906   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.757   2.374   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.136   1.608   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       4.136   0.076   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      -4.136  -3.140   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.136  -4.673   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.757   2.374   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.378   1.608   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.378  -0.077   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.153  -0.842   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.685   0.382   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.757  -0.689   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.604  -2.221   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.225  -2.987   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.153  -2.374   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.378  -3.140   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.757  -2.374   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.757  -0.842   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.136   0.076   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5   14                                                       
CONECT    7    8   19                                                       
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   17                                                       
CONECT   13   14                                                            
CONECT   14    6   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19    7   18   20                                                  
CONECT   20   11   19   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
N-(3,4-Dihydroxy-5-methoxycinnamoyl)-1,4-butanediamine	HMDB
(2Z)-N-(4-Aminobutyl)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enimidate	Generator

Chemical Formula

C₁₅H₂₂N₂O₄

Average Mass

294.3462 Da

Monoisotopic Mass

294.15796 Da

IUPAC Name

(2Z)-N-(4-aminobutyl)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enamide

Traditional Name

(2Z)-N-(4-aminobutyl)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enamide

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C/C(=O)NCCCCN)=CC(OC)=C1O

InChI Identifier

InChI=1S/C15H22N2O4/c1-20-12-9-11(10-13(21-2)15(12)19)5-6-14(18)17-8-4-3-7-16/h5-6,9-10,19H,3-4,7-8,16H2,1-2H3,(H,17,18)/b6-5-

InChI Key

ZYERUQAOCQZPJW-WAYWQWQTSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
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	0.95	ALOGPS
logP	-0.12	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	10	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	93.81 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	82.15 m³·mol⁻¹	ChemAxon
Polarizability	32.44 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033464

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011506

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

131751429

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Sinapoylputrescine (NP0336255)

MOL for NP0336255 (Sinapoylputrescine)

3D MOL for NP0336255 (Sinapoylputrescine)

3D SDF for NP0336255 (Sinapoylputrescine)

3D-SDF for NP0336255 (Sinapoylputrescine)

PDB for NP0336255 (Sinapoylputrescine)

3D PDB for NP0336255 (Sinapoylputrescine)

SMILES for NP0336255 (Sinapoylputrescine)

INCHI for NP0336255 (Sinapoylputrescine)

Structure for NP0336255 (Sinapoylputrescine)

3D Structure for NP0336255 (Sinapoylputrescine)