NP-MRD: Showing NP-Card for 4,5-Dihydropiperlonguminine (NP0084726)

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Record Information

Version

2.0

Created at

2022-04-29 05:23:55 UTC

Updated at

2022-04-29 05:23:55 UTC

NP-MRD ID

NP0084726

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-Dihydropiperlonguminine

Description

4,5-Dihydropiperlonguminine 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. 4,5-Dihydropiperlonguminine is a moderately basic compound (based on its pKa). Outside of the human body, 4,5-Dihydropiperlonguminine has been detected, but not quantified in, herbs and spices. 4,5-Dihydropiperlonguminine is found in Piper longum , Piper swartzianum and Piper tuberculatum. This could make 4,5-dihydropiperlonguminine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
   -5.1700   -1.1260   -0.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3198    0.0041    0.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8044    0.3750    0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6017    1.2147    0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2017    0.9587   -0.1832 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3133    0.6021    0.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7452    0.4971    2.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9014    0.3443    0.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2886    0.4080   -0.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633    0.1344   -0.6696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8266   -0.2170    0.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2703   -0.4654    0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7303   -1.7301   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0541   -1.9337   -0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9298   -0.8728   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5141    0.3878    0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1760    0.5723    0.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6122    1.2279    0.0727 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6857    0.5089   -0.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2944   -0.8503   -0.4661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9907   -1.8640   -0.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1778   -1.6173   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2765   -0.7308   -1.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0202   -0.2100    1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9987    0.9136   -0.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9917    1.0956    1.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4472   -0.5095    0.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7641    2.1076    0.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0712    1.3996   -0.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8159    1.0356   -1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2818    0.0777    1.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8462    0.6644   -1.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3722   -0.6022   -1.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6248    1.1032   -1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7297    0.6244    1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4106   -1.1425    1.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9736   -2.5131   -0.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3786   -2.9297   -0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8450    1.5716    0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8628    0.8546   -1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5741    0.6311    0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 20  1  0
 20 19  1  0
 19 18  1  0
 18 16  1  0
 16 17  2  0
 17 12  1  0
 16 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 19 40  1  0
 19 41  1  0
 17 39  1  0
M  END


  Mrv0541 02241210482D          

 20 21  0  0  0  0            999 V2000
   -2.5803    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8665   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8665   -0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5803   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2939   -0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2939   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0804    0.2529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5644   -0.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0804   -1.0821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1515    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4379   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2771    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9921   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7057    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7057    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4207   -0.0014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1344    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8494   -0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8494   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5644    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084726

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CNC(=O)\C=C\CCC1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO3/c1-12(2)10-17-16(18)6-4-3-5-13-7-8-14-15(9-13)20-11-19-14/h4,6-9,12H,3,5,10-11H2,1-2H3,(H,17,18)/b6-4+

> <INCHI_KEY>
CSGDXLXTJVRNEA-GQCTYLIASA-N

> <FORMULA>
C16H21NO3

> <MOLECULAR_WEIGHT>
275.3428

> <EXACT_MASS>
275.152143543

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.76725673496084

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-5-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)pent-2-enamide

> <ALOGPS_LOGP>
3.27

> <JCHEM_LOGP>
3.226793685666667

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.508281064792207

> <JCHEM_PKA_STRONGEST_BASIC>
2.3463140797056727

> <JCHEM_POLAR_SURFACE_AREA>
47.56

> <JCHEM_REFRACTIVITY>
78.49190000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-5-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)pent-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  C   UNK     0      -4.817   0.767   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.484  -0.003   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.484  -1.543   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.817  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.149  -1.543   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.149  -0.003   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.617   0.472   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -8.520  -0.775   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -7.617  -2.020   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.149   0.767   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.817  -0.003   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.517   0.767   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.852  -0.003   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.184   0.767   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.184   2.310   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       4.519  -0.003   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       5.851   0.767   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.186  -1.543   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.186  -0.003   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.520   0.767   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    5    8                                                       
CONECT   10    2   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   19                                                       
CONECT   18   19                                                            
CONECT   19   17   18   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
56-Dihydropiperlonguminine	HMDB
5-(1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)-2-pentenamide, 9ci	HMDB
Da,b-dihydropiperlonguminine	HMDB
N-Isobutyl-5-(3,4-methylenedioxyphenyl)-2-pentenamide, 8ci	HMDB
(2E)-5-(2H-1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)pent-2-enimidate	Generator
4,5-Dihydropiperlonguminine	MeSH

Chemical Formula

C₁₆H₂₁NO₃

Average Mass

275.3428 Da

Monoisotopic Mass

275.15214 Da

IUPAC Name

(2E)-5-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)pent-2-enamide

Traditional Name

(2E)-5-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)pent-2-enamide

CAS Registry Number

Not Available

SMILES

CC(C)CNC(=O)\C=C\CCC1=CC=C2OCOC2=C1

InChI Identifier

InChI=1S/C16H21NO3/c1-12(2)10-17-16(18)6-4-3-5-13-7-8-14-15(9-13)20-11-19-14/h4,6-9,12H,3,5,10-11H2,1-2H3,(H,17,18)/b6-4+

InChI Key

CSGDXLXTJVRNEA-GQCTYLIASA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Piper longum	Plant	KNApSAcK
Piper swartzianum	LOTUS Database	35616633
Piper tuberculatum	LOTUS Database	35616633

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-acyl-amine
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Acetal
Carboxylic acid derivative
Oxacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
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	3.27	ALOGPS
logP	3.23	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	15.51	ChemAxon
pKa (Strongest Basic)	2.35	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.56 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	78.49 m³·mol⁻¹	ChemAxon
Polarizability	31.77 Å³	ChemAxon
Number of Rings	2	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

HMDB0041488

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021456

KNApSAcK ID

Not Available

Chemspider ID

22914129

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12682184

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4,5-Dihydropiperlonguminine (NP0084726)

MOL for NP0084726 (4,5-Dihydropiperlonguminine)

3D MOL for NP0084726 (4,5-Dihydropiperlonguminine)

3D SDF for NP0084726 (4,5-Dihydropiperlonguminine)

3D-SDF for NP0084726 (4,5-Dihydropiperlonguminine)

PDB for NP0084726 (4,5-Dihydropiperlonguminine)

3D PDB for NP0084726 (4,5-Dihydropiperlonguminine)

SMILES for NP0084726 (4,5-Dihydropiperlonguminine)

INCHI for NP0084726 (4,5-Dihydropiperlonguminine)

Structure for NP0084726 (4,5-Dihydropiperlonguminine)

3D Structure for NP0084726 (4,5-Dihydropiperlonguminine)