NP-MRD: Showing NP-Card for n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-3-phenylprop-2-enimidic acid (NP0288950)

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Record Information

Version

2.0

Created at

2022-09-09 18:53:58 UTC

Updated at

2022-09-09 18:53:58 UTC

NP-MRD ID

NP0288950

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-3-phenylprop-2-enimidic acid

Description

N-{14-[1-(dimethylamino)ethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl}-3-phenylprop-2-enimidic acid belongs to the class of organic compounds known as azasteroids and derivatives. These are steroid derivatives in which one carbon atom in the steroidal skeleton has been substituted with a nitrogen atom. n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-3-phenylprop-2-enimidic acid is found in Pachysandra axillaris. N-{14-[1-(dimethylamino)ethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl}-3-phenylprop-2-enimidic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231515272D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004231515272D          

 35 39  0  0  0  0            999 V2000
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   11.4822   -0.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2943   -0.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8261   -0.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5458   -1.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7337   -1.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -2.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  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
  9 10  1  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
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  7 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
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 25 23  1  4  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0288950

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C1CCC2C3CCC4CC(CCC4(C)C3CCC12C)NC(=O)C=CC1=CC=CC=C1)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C32H48N2O/c1-22(34(4)5)27-14-15-28-26-13-12-24-21-25(33-30(35)16-11-23-9-7-6-8-10-23)17-19-31(24,2)29(26)18-20-32(27,28)3/h6-11,16,22,24-29H,12-15,17-21H2,1-5H3,(H,33,35)

> <INCHI_KEY>
KSLAHDQBEHULIV-UHFFFAOYSA-N

> <FORMULA>
C32H48N2O

> <MOLECULAR_WEIGHT>
476.749

> <EXACT_MASS>
476.376664174

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
59.222500950395684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{14-[1-(dimethylamino)ethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}-3-phenylprop-2-enamide

> <ALOGPS_LOGP>
6.09

> <JCHEM_LOGP>
6.559580447333336

> <ALOGPS_LOGS>
-7.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.00302130246982

> <JCHEM_PKA_STRONGEST_BASIC>
10.300296126852876

> <JCHEM_POLAR_SURFACE_AREA>
32.34

> <JCHEM_REFRACTIVITY>
147.17909999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.00e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-{14-[1-(dimethylamino)ethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}-3-phenylprop-2-enamide

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      16.362  -3.071   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.832  -5.696   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      18.871  -3.977   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.394  -2.529   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.910  -2.257   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.433  -0.809   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.949  -0.538   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      23.942  -1.715   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      23.419  -3.164   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      21.903  -3.435   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       3.257  -5.652   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.676  -4.226   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16   17                                             
CONECT   16   15                                                            
CONECT   17   15    7   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    3    6   21                                             
CONECT   21   20                                                            
CONECT   22   12   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33    2   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
N-{14-[1-(dimethylamino)ethyl]-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-5-yl}-3-phenylprop-2-enimidate	Generator
N-{14-[1-(dimethylamino)ethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}-3-phenylprop-2-enimidate	Generator

Chemical Formula

C₃₂H₄₈N₂O

Average Mass

476.7490 Da

Monoisotopic Mass

476.37666 Da

IUPAC Name

N-{14-[1-(dimethylamino)ethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}-3-phenylprop-2-enamide

Traditional Name

N-{14-[1-(dimethylamino)ethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}-3-phenylprop-2-enamide

CAS Registry Number

Not Available

SMILES

CC(C1CCC2C3CCC4CC(CCC4(C)C3CCC12C)NC(=O)C=CC1=CC=CC=C1)N(C)C

InChI Identifier

InChI=1S/C32H48N2O/c1-22(34(4)5)27-14-15-28-26-13-12-24-21-25(33-30(35)16-11-23-9-7-6-8-10-23)17-19-31(24,2)29(26)18-20-32(27,28)3/h6-11,16,22,24-29H,12-15,17-21H2,1-5H3,(H,33,35)

InChI Key

KSLAHDQBEHULIV-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
Pachysandra axillaris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azasteroids and derivatives. These are steroid derivatives in which one carbon atom in the steroidal skeleton has been substituted with a nitrogen atom.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Azasteroids and derivatives

Direct Parent

Azasteroids and derivatives

Alternative Parents

Substituents

22-azasteroid
Pregnane-skeleton
Pregnane-type alkaloid
Steroidal alkaloid
Azasteroid
Cinnamic acid amide
Cinnamic acid or derivatives
Alkaloid or derivatives
Styrene
Monocyclic benzene moiety
Benzenoid
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	6.09	ALOGPS
logP	6.56	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	16	ChemAxon
pKa (Strongest Basic)	10.3	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.34 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	147.18 m³·mol⁻¹	ChemAxon
Polarizability	59.22 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

75244640

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-3-phenylprop-2-enimidic acid (NP0288950)

MOL for NP0288950 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-3-phenylprop-2-enimidic acid)

3D MOL for NP0288950 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-3-phenylprop-2-enimidic acid)

3D SDF for NP0288950 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-3-phenylprop-2-enimidic acid)

3D-SDF for NP0288950 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-3-phenylprop-2-enimidic acid)

PDB for NP0288950 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-3-phenylprop-2-enimidic acid)

3D PDB for NP0288950 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-3-phenylprop-2-enimidic acid)

SMILES for NP0288950 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-3-phenylprop-2-enimidic acid)

INCHI for NP0288950 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-3-phenylprop-2-enimidic acid)

Structure for NP0288950 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-3-phenylprop-2-enimidic acid)

3D Structure for NP0288950 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-3-phenylprop-2-enimidic acid)