NP-MRD: Showing NP-Card for 1-(13-carboximidoyl-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl)-3-phenylprop-2-en-1-one (NP0321161)

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Record Information

Version

2.0

Created at

2022-09-11 23:13:46 UTC

Updated at

2022-09-11 23:13:46 UTC

NP-MRD ID

NP0321161

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(13-carboximidoyl-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl)-3-phenylprop-2-en-1-one

Description

1-(13-Carboximidoyl-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl)-3-phenylprop-2-en-1-one belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid. 1-(13-carboximidoyl-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl)-3-phenylprop-2-en-1-one is found in Incarvillea sinensis. 1-(13-Carboximidoyl-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl)-3-phenylprop-2-en-1-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171519092D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004171519092D          

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 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 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
  3 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  2  0  0  0  0
 29 27  1  4  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321161

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N=CN1CCCCN(CCCNC(=O)CC(NCCC1)C1=CC=CC=C1)C(=O)C=CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H39N5O2/c30-24-33-19-7-8-21-34(29(36)16-15-25-11-3-1-4-12-25)22-10-18-32-28(35)23-27(31-17-9-20-33)26-13-5-2-6-14-26/h1-6,11-16,24,27,30-31H,7-10,17-23H2,(H,32,35)

> <INCHI_KEY>
NFLWYWGWAOASJD-UHFFFAOYSA-N

> <FORMULA>
C29H39N5O2

> <MOLECULAR_WEIGHT>
489.664

> <EXACT_MASS>
489.310375516

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
55.89733179573068

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13-carboximidoyl-8-phenyl-1-(3-phenylprop-2-enoyl)-1,5,9,13-tetraazacycloheptadecan-6-one

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.212680656666666

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.669573666893754

> <JCHEM_PKA_STRONGEST_BASIC>
11.723315821340698

> <JCHEM_POLAR_SURFACE_AREA>
88.53

> <JCHEM_REFRACTIVITY>
157.12719999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-carboximidoyl-8-phenyl-1-(3-phenylprop-2-enoyl)-1,5,9,13-tetraazacycloheptadecan-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  N   UNK     0      -0.373  -2.735   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -0.165  -1.209   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.261  -0.626   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.230   0.518   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.000   1.852   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.506   1.532   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       9.336  -0.770   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.002   7.700   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.669   7.700   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.336   5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    3                                                       
CONECT   21   16   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27    8   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₉N₅O₂

Average Mass

489.6640 Da

Monoisotopic Mass

489.31038 Da

IUPAC Name

13-carboximidoyl-8-phenyl-1-(3-phenylprop-2-enoyl)-1,5,9,13-tetraazacycloheptadecan-6-one

Traditional Name

13-carboximidoyl-8-phenyl-1-(3-phenylprop-2-enoyl)-1,5,9,13-tetraazacycloheptadecan-6-one

CAS Registry Number

Not Available

SMILES

N=CN1CCCCN(CCCNC(=O)CC(NCCC1)C1=CC=CC=C1)C(=O)C=CC1=CC=CC=C1

InChI Identifier

InChI=1S/C29H39N5O2/c30-24-33-19-7-8-21-34(29(36)16-15-25-11-3-1-4-12-25)22-10-18-32-28(35)23-27(31-17-9-20-33)26-13-5-2-6-14-26/h1-6,11-16,24,27,30-31H,7-10,17-23H2,(H,32,35)

InChI Key

NFLWYWGWAOASJD-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Incarvillea sinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Not Available

Direct Parent

Cinnamic acids and derivatives

Alternative Parents

Substituents

Cinnamic acid or derivatives
Styrene
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Cyclic carboximidic acid
Amino acid or derivatives
Carboxamide group
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organoheterocyclic compound
Carboximidamide
Amidine
Carboxylic acid amidine
Secondary amine
Carboxylic acid derivative
Formamidine
Secondary aliphatic amine
Hydrocarbon derivative
Imine
Organonitrogen compound
Organooxygen compound
Amine
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.17	ALOGPS
logP	2.21	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	14.67	ChemAxon
pKa (Strongest Basic)	11.72	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	88.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	157.13 m³·mol⁻¹	ChemAxon
Polarizability	55.9 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(13-carboximidoyl-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl)-3-phenylprop-2-en-1-one (NP0321161)

MOL for NP0321161 (1-(13-carboximidoyl-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl)-3-phenylprop-2-en-1-one)

3D MOL for NP0321161 (1-(13-carboximidoyl-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl)-3-phenylprop-2-en-1-one)

3D SDF for NP0321161 (1-(13-carboximidoyl-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl)-3-phenylprop-2-en-1-one)

3D-SDF for NP0321161 (1-(13-carboximidoyl-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl)-3-phenylprop-2-en-1-one)

PDB for NP0321161 (1-(13-carboximidoyl-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl)-3-phenylprop-2-en-1-one)

3D PDB for NP0321161 (1-(13-carboximidoyl-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl)-3-phenylprop-2-en-1-one)

SMILES for NP0321161 (1-(13-carboximidoyl-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl)-3-phenylprop-2-en-1-one)

INCHI for NP0321161 (1-(13-carboximidoyl-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl)-3-phenylprop-2-en-1-one)

Structure for NP0321161 (1-(13-carboximidoyl-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl)-3-phenylprop-2-en-1-one)

3D Structure for NP0321161 (1-(13-carboximidoyl-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl)-3-phenylprop-2-en-1-one)