NP-MRD: Showing NP-Card for (2E,4E,8E)-Piperamide-C9:3 (NP0335573)

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Record Information

Version

2.0

Created at

2024-09-11 02:13:45 UTC

Updated at

2024-09-11 02:13:45 UTC

NP-MRD ID

NP0335573

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2E,4E,8E)-Piperamide-C9:3

Description

(2E,4E,8E)-Piperamide-C9:3, Also known as piperamide-C9:3 (2E,4E,8E), belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms (2E,4E,8E)-Piperamide-C9:3 Is a moderately basic compound (based on its pKa). Outside of the human body, (2E,4E,8E)-Piperamide-C9:3 Has been detected, but not quantified in, herbs and spices and pepper (spice). This could make (2E,4E,8E)-piperamide-C9:3 A potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310342D          

 24 26  0  0  0  0            999 V2000
    6.1368    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5859    5.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1734    5.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0339    4.6144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3665    5.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 12 11  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 17  9  1  0  0  0  0
 17 11  1  0  0  0  0
 17 15  2  0  0  0  0
 18 12  1  0  0  0  0
 19 15  1  0  0  0  0
 19 18  2  0  0  0  0
 20 10  1  0  0  0  0
 21 13  1  0  0  0  0
 21 14  1  0  0  0  0
 21 20  1  0  0  0  0
 22 20  2  0  0  0  0
 23 16  1  0  0  0  0
 23 18  1  0  0  0  0
 24 16  1  0  0  0  0
 24 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335573

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C(\C=C\C=C\CC\C=C/C1=CC2=C(OCO2)C=C1)N1CCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO3/c22-20(21-13-7-8-14-21)10-6-4-2-1-3-5-9-17-11-12-18-19(15-17)24-16-23-18/h2,4-6,9-12,15H,1,3,7-8,13-14,16H2/b4-2+,9-5-,10-6+

> <INCHI_KEY>
XWQSYLYFCJTIEL-JWXNOOABSA-N

> <FORMULA>
C20H23NO3

> <MOLECULAR_WEIGHT>
325.4015

> <EXACT_MASS>
325.167793607

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.7859683203351

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,8Z)-9-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)nona-2,4,8-trien-1-one

> <ALOGPS_LOGP>
4.40

> <JCHEM_LOGP>
3.7490953886666665

> <ALOGPS_LOGS>
-4.63

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.0702111430660985

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
97.82260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,8Z)-9-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)nona-2,4,8-trien-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      11.455   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.455   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.122   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.789   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.122   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.789   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.894   9.758   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.124  11.092   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.123   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.863   8.614   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.617  10.772   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.123   8.470   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      15.456   9.240   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      12.789   9.240   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    9                                                       
CONECT    6    4   10                                                       
CONECT    7    8   13                                                       
CONECT    8    7   14                                                       
CONECT    9    5   17                                                       
CONECT   10    6   20                                                       
CONECT   11   12   17                                                       
CONECT   12   11   18                                                       
CONECT   13    7   21                                                       
CONECT   14    8   21                                                       
CONECT   15   17   19                                                       
CONECT   16   23   24                                                       
CONECT   17    9   11   15                                                  
CONECT   18   12   19   23                                                  
CONECT   19   15   18   24                                                  
CONECT   20   10   21   22                                                  
CONECT   21   13   14   20                                                  
CONECT   22   20                                                            
CONECT   23   16   18                                                       
CONECT   24   16   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
Piperamide-C9:3 (2E,4E,8E)	HMDB

Chemical Formula

C₂₀H₂₃NO₃

Average Mass

325.4015 Da

Monoisotopic Mass

325.16779 Da

IUPAC Name

(2E,4E,8Z)-9-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)nona-2,4,8-trien-1-one

Traditional Name

(2E,4E,8Z)-9-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)nona-2,4,8-trien-1-one

CAS Registry Number

Not Available

SMILES

O=C(\C=C\C=C\CC\C=C/C1=CC2=C(OCO2)C=C1)N1CCCC1

InChI Identifier

InChI=1S/C20H23NO3/c22-20(21-13-7-8-14-21)10-6-4-2-1-3-5-9-17-11-12-18-19(15-17)24-16-23-18/h2,4-6,9-12,15H,1,3,7-8,13-14,16H2/b4-2+,9-5-,10-6+

InChI Key

XWQSYLYFCJTIEL-JWXNOOABSA-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 benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
N-acylpyrrolidine
Styrene
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	4.4	ALOGPS
logP	3.75	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	2.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	97.82 m³·mol⁻¹	ChemAxon
Polarizability	36.79 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0038644

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018039

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

131752410

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (2E,4E,8E)-Piperamide-C9:3 (NP0335573)

MOL for NP0335573 ((2E,4E,8E)-Piperamide-C9:3)

3D MOL for NP0335573 ((2E,4E,8E)-Piperamide-C9:3)

3D SDF for NP0335573 ((2E,4E,8E)-Piperamide-C9:3)

3D-SDF for NP0335573 ((2E,4E,8E)-Piperamide-C9:3)

PDB for NP0335573 ((2E,4E,8E)-Piperamide-C9:3)

3D PDB for NP0335573 ((2E,4E,8E)-Piperamide-C9:3)

SMILES for NP0335573 ((2E,4E,8E)-Piperamide-C9:3)

INCHI for NP0335573 ((2E,4E,8E)-Piperamide-C9:3)

Structure for NP0335573 ((2E,4E,8E)-Piperamide-C9:3)

3D Structure for NP0335573 ((2E,4E,8E)-Piperamide-C9:3)