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Showing NP-Card for Sarmentine (NP0049245)

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Record Information
Version2.0
Created at2022-03-17 21:09:24 UTC
Updated at2022-03-17 21:09:24 UTC
NP-MRD IDNP0049245
Secondary Accession NumbersNone
Natural Product Identification
Common NameSarmentine
DescriptionSarmentine belongs to the class of organic compounds known as n-acylpyrrolidines. These are n-Acylated Pyrrolidine derivatives. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. Sarmentine is a moderately basic compound (based on its pKa). Outside of the human body, Sarmentine has been detected, but not quantified in, herbs and spices and pepper (spice). Sarmentine is found in Piper sarmentosum and Piperaceae. This could make sarmentine a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049245 (Sarmentine)


  Mrv0541 05061310412D          

 16 16  0  0  0  0            999 V2000
    0.8853    5.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5998    5.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143    5.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0287    5.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7432    5.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4577    5.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1721    5.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1721    6.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9068    8.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4943    9.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8866    7.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3548    7.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6873    9.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8866    7.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6011    8.2627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1721    8.2627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  2  0  0  0  0
M  END
Download

3D MOL for NP0049245 (Sarmentine)

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3D SDF for NP0049245 (Sarmentine)

  Mrv0541 05061310412D          

 16 16  0  0  0  0            999 V2000
    0.8853    5.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5998    5.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143    5.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0287    5.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7432    5.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4577    5.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1721    5.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1721    6.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9068    8.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4943    9.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8866    7.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3548    7.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6873    9.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8866    7.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6011    8.2627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1721    8.2627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0049245

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C=C/C(=O)N1CCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C14H23NO/c1-2-3-4-5-6-7-8-11-14(16)15-12-9-10-13-15/h6-8,11H,2-5,9-10,12-13H2,1H3/b7-6-,11-8+

> <INCHI_KEY>
BFZBGTMIBOQWBA-BQGCWICQSA-N

> <FORMULA>
C14H23NO

> <MOLECULAR_WEIGHT>
221.3385

> <EXACT_MASS>
221.177964363

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.976880866958844

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4Z)-1-(pyrrolidin-1-yl)deca-2,4-dien-1-one

> <ALOGPS_LOGP>
4.15

> <JCHEM_LOGP>
3.271279604999999

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.070215683476251

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
70.8441

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4Z)-1-(pyrrolidin-1-yl)deca-2,4-dien-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0049245 (Sarmentine)
Download
PDB for NP0049245 (Sarmentine)
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       1.653  10.804   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.986  10.034   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.320  10.804   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.654  10.034   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.987  10.804   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.321  10.034   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.655  10.804   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.655  12.344   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.759  15.942   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.989  17.275   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.988  13.114   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.729  14.797   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.483  16.955   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.988  14.654   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      12.322  15.424   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       9.655  15.424   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    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   11                                                       
CONECT    9   10   12                                                       
CONECT   10    9   13                                                       
CONECT   11    8   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   15                                                       
CONECT   14   11   15   16                                                  
CONECT   15   12   13   14                                                  
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

Download
3D PDB for NP0049245 (Sarmentine)
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SMILES for NP0049245 (Sarmentine)
CCCCC\C=C/C=C/C(=O)N1CCCC1
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INCHI for NP0049245 (Sarmentine)
InChI=1S/C14H23NO/c1-2-3-4-5-6-7-8-11-14(16)15-12-9-10-13-15/h6-8,11H,2-5,9-10,12-13H2,1H3/b7-6-,11-8+
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View in JSmol
Synonyms
ValueSource
1-((2E,4E)-1-oxo-2,4-Decadienyl)-pyrrolidineHMDB
1-(1-oxo-2,4-Decadienyl)pyrrolidine, 9ciHMDB
1-(2,4-Decadienoyl)pyrrolidineHMDB
2,4-Decadienoic acid pyrrolidideHMDB
Chemical FormulaC14H23NO
Average Mass221.3385 Da
Monoisotopic Mass221.17796 Da
IUPAC Name(2E,4Z)-1-(pyrrolidin-1-yl)deca-2,4-dien-1-one
Traditional Name(2E,4Z)-1-(pyrrolidin-1-yl)deca-2,4-dien-1-one
CAS Registry Number78910-33-5
SMILES
CCCCC\C=C/C=C/C(=O)N1CCCC1
InChI Identifier
InChI=1S/C14H23NO/c1-2-3-4-5-6-7-8-11-14(16)15-12-9-10-13-15/h6-8,11H,2-5,9-10,12-13H2,1H3/b7-6-,11-8+
InChI KeyBFZBGTMIBOQWBA-BQGCWICQSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Piper nigrum L.FooDB
Piper sarmentosumPlant
Piperaceae-
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acylpyrrolidines. These are n-Acylated Pyrrolidine derivatives. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrrolidines  
Sub ClassN-acylpyrrolidines  
Direct ParentN-acylpyrrolidines  
Alternative Parents
Substituents
  • N-acylpyrrolidine
    • 

  • Tertiary carboxylic acid amide
    • 

  • Carboxamide group
    • 

  • Azacycle
    • 

  • Carboxylic acid derivative
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.15ALOGPS
logP3.27ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)2.07ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity70.84 m³·mol⁻¹ChemAxon
Polarizability26.98 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038840  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018275  
KNApSAcK IDC00031306  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound46935132  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available