NP-MRD: Showing NP-Card for n-{1-[9a,11a-dimethyl-7-(methylamino)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl}-n-methylacetamide (NP0291824)

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Record Information

Version

2.0

Created at

2022-09-09 23:03:42 UTC

Updated at

2022-09-09 23:03:42 UTC

NP-MRD ID

NP0291824

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-{1-[9a,11a-dimethyl-7-(methylamino)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl}-n-methylacetamide

Description

N-{1-[2,15-dimethyl-5-(methylamino)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl]ethyl}-N-methylacetamide 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-[9a,11a-dimethyl-7-(methylamino)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl}-n-methylacetamide is found in Sarcococca saligna. N-{1-[2,15-dimethyl-5-(methylamino)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl]ethyl}-N-methylacetamide is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161502022D          

 28 31  0  0  0  0            999 V2000
    0.9533    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2336   -0.5346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9503   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9215    0.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7336    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -0.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -0.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -1.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4373   -2.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1264   -2.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2545   -1.9175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5654   -1.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7609   -2.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5781   -2.4560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4500   -3.3330    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
  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
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  6  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
 15 16  1  0  0  0  0
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 16 18  1  0  0  0  0
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  6 27  1  0  0  0  0
 11 27  1  0  0  0  0
  8 28  1  0  0  0  0
  3 28  1  0  0  0  0
M  END

     RDKit          3D

 72 75  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1533004161502022D          

 28 31  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0291824

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNC1CCC2(C)C(CCC3C4CCC(C(C)N(C)C(C)=O)C4(C)CCC23)C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H44N2O/c1-16(27(6)17(2)28)21-9-10-22-20-8-7-18-15-19(26-5)11-13-24(18,3)23(20)12-14-25(21,22)4/h16,18-23,26H,7-15H2,1-6H3

> <INCHI_KEY>
WRFQFEGHCJALCO-UHFFFAOYSA-N

> <FORMULA>
C25H44N2O

> <MOLECULAR_WEIGHT>
388.64

> <EXACT_MASS>
388.345364045

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
48.73896875143859

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{1-[2,15-dimethyl-5-(methylamino)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethyl}-N-methylacetamide

> <ALOGPS_LOGP>
4.93

> <JCHEM_LOGP>
4.040776601333335

> <ALOGPS_LOGS>
-5.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.698928055119307

> <JCHEM_POLAR_SURFACE_AREA>
32.34

> <JCHEM_REFRACTIVITY>
116.36489999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.79e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-{1-[2,15-dimethyl-5-(methylamino)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethyl}-N-methylacetamide

> <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  C   UNK     0       1.780   0.451   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.303  -0.998   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.819  -1.269   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.342  -2.717   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.858  -2.988   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.851  -1.811   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.374  -3.259   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.327  -0.363   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.320   0.815   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.836   0.544   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.359  -0.905   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.875  -1.176   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.091  -0.231   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.366  -1.095   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.938  -2.574   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.883  -3.790   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.303  -5.217   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      15.408  -3.579   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      15.989  -2.153   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.354  -4.795   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      17.879  -4.585   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      15.773  -6.222   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.399  -2.624   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.070  -4.010   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.406  -3.802   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.890  -3.531   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.367  -2.082   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.811  -0.092   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   27                                             
CONECT    7    6                                                            
CONECT    8    6    9   28                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   27                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   15   12   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    6   11                                                  
CONECT   28    8    3                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₄₄N₂O

Average Mass

388.6400 Da

Monoisotopic Mass

388.34536 Da

IUPAC Name

N-{1-[2,15-dimethyl-5-(methylamino)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethyl}-N-methylacetamide

Traditional Name

N-{1-[2,15-dimethyl-5-(methylamino)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethyl}-N-methylacetamide

CAS Registry Number

Not Available

SMILES

CNC1CCC2(C)C(CCC3C4CCC(C(C)N(C)C(C)=O)C4(C)CCC23)C1

InChI Identifier

InChI=1S/C25H44N2O/c1-16(27(6)17(2)28)21-9-10-22-20-8-7-18-15-19(26-5)11-13-24(18,3)23(20)12-14-25(21,22)4/h16,18-23,26H,7-15H2,1-6H3

InChI Key

WRFQFEGHCJALCO-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 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
Tertiary carboxylic acid amide
Acetamide
Carboxamide group
Amino acid or derivatives
Secondary amine
Secondary aliphatic amine
Carboxylic acid derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
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	4.93	ALOGPS
logP	4.04	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Basic)	10.7	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	3	ChemAxon
Refractivity	116.36 m³·mol⁻¹	ChemAxon
Polarizability	48.74 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

75017001

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-[9a,11a-dimethyl-7-(methylamino)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl}-n-methylacetamide (NP0291824)

MOL for NP0291824 (n-{1-[9a,11a-dimethyl-7-(methylamino)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl}-n-methylacetamide)

3D MOL for NP0291824 (n-{1-[9a,11a-dimethyl-7-(methylamino)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl}-n-methylacetamide)

3D SDF for NP0291824 (n-{1-[9a,11a-dimethyl-7-(methylamino)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl}-n-methylacetamide)

3D-SDF for NP0291824 (n-{1-[9a,11a-dimethyl-7-(methylamino)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl}-n-methylacetamide)

PDB for NP0291824 (n-{1-[9a,11a-dimethyl-7-(methylamino)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl}-n-methylacetamide)

3D PDB for NP0291824 (n-{1-[9a,11a-dimethyl-7-(methylamino)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl}-n-methylacetamide)

SMILES for NP0291824 (n-{1-[9a,11a-dimethyl-7-(methylamino)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl}-n-methylacetamide)

INCHI for NP0291824 (n-{1-[9a,11a-dimethyl-7-(methylamino)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl}-n-methylacetamide)

Structure for NP0291824 (n-{1-[9a,11a-dimethyl-7-(methylamino)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl}-n-methylacetamide)

3D Structure for NP0291824 (n-{1-[9a,11a-dimethyl-7-(methylamino)-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethyl}-n-methylacetamide)