NP-MRD: Showing NP-Card for Subaphylline (NP0047653)

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Record Information

Version

2.0

Created at

2022-03-17 20:43:44 UTC

Updated at

2022-03-17 20:43:44 UTC

NP-MRD ID

NP0047653

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Subaphylline

Description

Subaphylline 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. Subaphylline is a very strong basic compound (based on its pKa). Outside of the human body, Subaphylline is found, on average, in the highest concentration within sweet oranges. Subaphylline has also been detected, but not quantified in, several different foods, such as mandarin orange (clementine, tangerine), fruits, potato, pineapples, and corns. Subaphylline is found in Citrus aurantium , Citrus paradisi , Gomphrena globosa , Oryza sativa and Salsola subaphylla. This could make subaphylline a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241219132D          

 19 19  0  0  0  0            999 V2000
    0.0004    2.0929    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6563    2.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3952    2.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4773    1.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2161    0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2161    0.0406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2161    0.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4773   -0.4511    0.0000 C   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
   -0.0817   -1.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7384   -1.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4773   -1.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2161   -1.6825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2161   -2.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6563   -1.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3952   -1.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4773   -0.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026    0.2049    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 18  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  2  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047653

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(\C=C/C(=O)NCCCCN)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H20N2O3/c1-19-13-10-11(4-6-12(13)17)5-7-14(18)16-9-3-2-8-15/h4-7,10,17H,2-3,8-9,15H2,1H3,(H,16,18)/b7-5-

> <INCHI_KEY>
SFUVCMKSYKHYLD-ALCCZGGFSA-N

> <FORMULA>
C14H20N2O3

> <MOLECULAR_WEIGHT>
264.3202

> <EXACT_MASS>
264.147392516

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.91081569865409

> <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-methoxyphenyl)prop-2-enamide

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
0.3113241993134673

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.933109387168052

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.595294353133518

> <JCHEM_PKA_STRONGEST_BASIC>
10.197490271468649

> <JCHEM_POLAR_SURFACE_AREA>
84.58000000000001

> <JCHEM_REFRACTIVITY>
75.6827

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.89e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-N-(4-aminobutyl)-3-(4-hydroxy-3-methoxyphenyl)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   3.907   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   3.907   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.758   2.374   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.137   1.608   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       4.137   0.076   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      -4.137   0.076   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.758  -0.842   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.378  -0.077   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.153  -0.842   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.153  -2.374   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.378  -3.141   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.758  -2.374   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.137  -3.141   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.137  -4.673   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       2.604  -2.221   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.758  -0.689   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.685   0.382   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   18                                                       
CONECT    7    8                                                            
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13    8   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   11   17                                                       
CONECT   17   16   18                                                       
CONECT   18    6   17   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
4-Oxy-3-methoxycinnamylputrescine	HMDB
Feruloylputrescine	HMDB
N-(4-Aminobutyl)-4-hydroxy-3-methoxy-cinnamamide	HMDB
N-(4-Aminobutyl)-4-hydroxy-3-methoxycinnamamide	HMDB
N-(4-Hydroxy-3-methoxycinnamoyl)-1,4-butanediamine	HMDB
N-Feruloylputrescine	HMDB
Subaphyllin	HMDB
trans-N-Feruloylputrescine	HMDB
(2Z)-N-(4-Aminobutyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidate	Generator

Chemical Formula

C₁₄H₂₀N₂O₃

Average Mass

264.3202 Da

Monoisotopic Mass

264.14739 Da

IUPAC Name

(2Z)-N-(4-aminobutyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide

Traditional Name

(2Z)-N-(4-aminobutyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide

CAS Registry Number

501-13-3

SMILES

COC1=C(O)C=CC(\C=C/C(=O)NCCCCN)=C1

InChI Identifier

InChI=1S/C14H20N2O3/c1-19-13-10-11(4-6-12(13)17)5-7-14(18)16-9-3-2-8-15/h4-7,10,17H,2-3,8-9,15H2,1H3,(H,16,18)/b7-5-

InChI Key

SFUVCMKSYKHYLD-ALCCZGGFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ananas comosus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus aurantium	Plant	KNApSAcK
Citrus paradisi	Plant	KNApSAcK
Citrus reticulata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gomphrena globosa	Plant	KNApSAcK
Oryza sativa	Plant	KNApSAcK
Persea americana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salsola subaphylla	Plant	KNApSAcK
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zea mays L.	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
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
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	0.9	ALOGPS
logP	0.31	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.6	ChemAxon
pKa (Strongest Basic)	10.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	84.58 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	75.68 m³·mol⁻¹	ChemAxon
Polarizability	28.91 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

HMDB0033463

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92339985

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Subaphylline (NP0047653)

MOL for NP0047653 (Subaphylline)

3D MOL for NP0047653 (Subaphylline)

3D SDF for NP0047653 (Subaphylline)

3D-SDF for NP0047653 (Subaphylline)

PDB for NP0047653 (Subaphylline)

3D PDB for NP0047653 (Subaphylline)

SMILES for NP0047653 (Subaphylline)

INCHI for NP0047653 (Subaphylline)

Structure for NP0047653 (Subaphylline)

3D Structure for NP0047653 (Subaphylline)