NP-MRD: Showing NP-Card for n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-n,3,4-trimethylpent-2-enamide (NP0216275)

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Record Information

Version

2.0

Created at

2022-09-05 16:10:01 UTC

Updated at

2022-09-05 16:10:01 UTC

NP-MRD ID

NP0216275

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-n,3,4-trimethylpent-2-enamide

Description

N-{14-[1-(dimethylamino)ethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl}-N,3,4-trimethylpent-2-enamide 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}-n,3,4-trimethylpent-2-enamide is found in Sarcococca hookeriana and Sarcococca saligna. N-{14-[1-(dimethylamino)ethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl}-N,3,4-trimethylpent-2-enamide is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251506502D          

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M  END

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M  END


  Mrv1533004251506502D          

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    7.4373   -2.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2545   -1.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1264   -2.7946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6327   -3.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3091   -2.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -1.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4662   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -1.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -1.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3927    1.7932    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  4  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 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
 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
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 22 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 13 32  1  0  0  0  0
 18 32  1  0  0  0  0
 15 33  1  0  0  0  0
 10 33  1  0  0  0  0
  4 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0216275

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(C)=CC(=O)N(C)C1CCC2(C)C(CCC3C4CCC(C(C)N(C)C)C4(C)CCC23)C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H54N2O/c1-20(2)21(3)18-29(34)33(9)24-14-16-30(5)23(19-24)10-11-25-27-13-12-26(22(4)32(7)8)31(27,6)17-15-28(25)30/h18,20,22-28H,10-17,19H2,1-9H3

> <INCHI_KEY>
WCBPBBFIAODRLI-UHFFFAOYSA-N

> <FORMULA>
C31H54N2O

> <MOLECULAR_WEIGHT>
470.786

> <EXACT_MASS>
470.423614367

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
59.76188149000021

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <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}-N,3,4-trimethylpent-2-enamide

> <ALOGPS_LOGP>
5.88

> <JCHEM_LOGP>
6.541701573333334

> <ALOGPS_LOGS>
-6.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.30029698798619

> <JCHEM_POLAR_SURFACE_AREA>
23.550000000000004

> <JCHEM_REFRACTIVITY>
145.4124

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.28e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-{14-[1-(dimethylamino)ethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}-N,3,4-trimethylpent-2-enamide

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -2.299   3.889   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.776   2.441   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.768   1.264   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.260   2.170   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.264   0.722   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.780   0.451   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.772   1.628   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       2.303  -0.998   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.310  -2.175   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.819  -1.269   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.342  -2.717   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.858  -2.988   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.851  -1.811   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.374  -3.259   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.327  -0.363   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.320   0.815   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.836   0.544   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.359  -0.905   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.875  -1.176   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.091  -0.231   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.366  -1.095   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.938  -2.574   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.883  -3.790   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.408  -3.579   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      13.303  -5.217   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      14.248  -6.432   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.777  -5.427   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.399  -2.624   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.070  -4.010   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.406  -3.802   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.890  -3.531   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.367  -2.082   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.811  -0.092   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.733   3.347   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   34                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   33                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   32                                             
CONECT   14   13                                                            
CONECT   15   13   16   33                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   32                                                  
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22   19   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   13   18                                                  
CONECT   33   15   10                                                       
CONECT   34    4                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₅₄N₂O

Average Mass

470.7860 Da

Monoisotopic Mass

470.42361 Da

IUPAC Name

N-{14-[1-(dimethylamino)ethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}-N,3,4-trimethylpent-2-enamide

Traditional Name

N-{14-[1-(dimethylamino)ethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}-N,3,4-trimethylpent-2-enamide

CAS Registry Number

Not Available

SMILES

CC(C)C(C)=CC(=O)N(C)C1CCC2(C)C(CCC3C4CCC(C(C)N(C)C)C4(C)CCC23)C1

InChI Identifier

InChI=1S/C31H54N2O/c1-20(2)21(3)18-29(34)33(9)24-14-16-30(5)23(19-24)10-11-25-27-13-12-26(22(4)32(7)8)31(27,6)17-15-28(25)30/h18,20,22-28H,10-17,19H2,1-9H3

InChI Key

WCBPBBFIAODRLI-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
Sarcococca hookeriana	LOTUS Database	35616633
Sarcococca saligna	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
Alkaloid or derivatives
N-acyl-amine
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Amine
Organopnictogen compound
Organic nitrogen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	5.88	ALOGPS
logP	6.54	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Basic)	10.3	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	145.41 m³·mol⁻¹	ChemAxon
Polarizability	59.76 Å³	ChemAxon
Number of Rings	4	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

75289208

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}-n,3,4-trimethylpent-2-enamide (NP0216275)

MOL for NP0216275 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-n,3,4-trimethylpent-2-enamide)

3D MOL for NP0216275 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-n,3,4-trimethylpent-2-enamide)

3D SDF for NP0216275 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-n,3,4-trimethylpent-2-enamide)

3D-SDF for NP0216275 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-n,3,4-trimethylpent-2-enamide)

PDB for NP0216275 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-n,3,4-trimethylpent-2-enamide)

3D PDB for NP0216275 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-n,3,4-trimethylpent-2-enamide)

SMILES for NP0216275 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-n,3,4-trimethylpent-2-enamide)

INCHI for NP0216275 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-n,3,4-trimethylpent-2-enamide)

Structure for NP0216275 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-n,3,4-trimethylpent-2-enamide)

3D Structure for NP0216275 (n-{1-[1-(dimethylamino)ethyl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl}-n,3,4-trimethylpent-2-enamide)