NP-MRD: Showing NP-Card for 5-(2h-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one (NP0327982)

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Record Information

Version

2.0

Created at

2022-09-12 11:02:35 UTC

Updated at

2022-09-12 11:02:35 UTC

NP-MRD ID

NP0327982

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(2h-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

Description

NSC 242267 belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. 5-(2h-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one is found in Aglaia perviridis, Piper betle, Piper capense, Piper cubeba, Piper guineense, Piper longum, Piper nigrum, Piper retrofractum, Piper swartzianum and Piper tuberculatum. NSC 242267 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161501492D          

 21 23  0  0  0  0            999 V2000
    5.4957    5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    4.4104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  5  4  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 15  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327982

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C(C=CC=CC1=CC=C2OCOC2=C1)N1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2

> <INCHI_KEY>
MXXWOMGUGJBKIW-UHFFFAOYSA-N

> <FORMULA>
C17H19NO3

> <MOLECULAR_WEIGHT>
285.343

> <EXACT_MASS>
285.136493476

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
31.970686964203328

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

> <ALOGPS_LOGP>
3.38

> <JCHEM_LOGP>
2.777311050333333

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.13200194795020026

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
82.90299999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0      10.259  10.543   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.259   9.003   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      11.592   8.233   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      12.926   9.003   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.260   8.233   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.260   6.693   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.926   5.923   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.592   6.693   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10   15                                                  
CONECT   15   14    7                                                       
CONECT   16    2   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₉NO₃

Average Mass

285.3430 Da

Monoisotopic Mass

285.13649 Da

IUPAC Name

5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

Traditional Name

5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

CAS Registry Number

Not Available

SMILES

O=C(C=CC=CC1=CC=C2OCOC2=C1)N1CCCCC1

InChI Identifier

InChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2

InChI Key

MXXWOMGUGJBKIW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aglaia perviridis	LOTUS Database	35616633
Piper betle	LOTUS Database	35616633
Piper capense	LOTUS Database	35616633
Piper cubeba	LOTUS Database	35616633
Piper guineense	LOTUS Database	35616633
Piper longum	LOTUS Database	35616633
Piper nigrum	LOTUS Database	35616633
Piper retrofractum	LOTUS Database	35616633
Piper swartzianum	LOTUS Database	35616633
Piper tuberculatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Benzodioxole
N-acyl-piperidine
Alkaloid or derivatives
Styrene
Piperidine
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (N-EE-PIPEROYL-PIPERIDINE )

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	3.38	ALOGPS
logP	2.78	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-0.13	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	3	ChemAxon
Refractivity	82.9 m³·mol⁻¹	ChemAxon
Polarizability	31.97 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

4840

PDB ID

Not Available

ChEBI ID

93043

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(2h-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one (NP0327982)

MOL for NP0327982 (5-(2h-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one)

3D MOL for NP0327982 (5-(2h-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one)

3D SDF for NP0327982 (5-(2h-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one)

3D-SDF for NP0327982 (5-(2h-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one)

PDB for NP0327982 (5-(2h-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one)

3D PDB for NP0327982 (5-(2h-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one)

SMILES for NP0327982 (5-(2h-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one)

INCHI for NP0327982 (5-(2h-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one)

Structure for NP0327982 (5-(2h-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one)

3D Structure for NP0327982 (5-(2h-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one)