NP-MRD: Showing NP-Card for n-{1-[1-(dimethylamino)ethyl]-2-hydroxy-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl}-3-methylbut-2-enimidic acid (NP0198937)

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Record Information

Version

2.0

Created at

2022-09-04 17:29:01 UTC

Updated at

2022-09-04 17:29:02 UTC

NP-MRD ID

NP0198937

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-{1-[1-(dimethylamino)ethyl]-2-hydroxy-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl}-3-methylbut-2-enimidic acid

Description

N-{14-[1-(dimethylamino)ethyl]-13-hydroxy-2,15-dimethyl-6-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-4-en-5-yl}-3-methylbut-2-enimidic acid belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. n-{1-[1-(dimethylamino)ethyl]-2-hydroxy-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl}-3-methylbut-2-enimidic acid is found in Pachysandra axillaris. N-{14-[1-(dimethylamino)ethyl]-13-hydroxy-2,15-dimethyl-6-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-4-en-5-yl}-3-methylbut-2-enimidic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151519552D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004151519552D          

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  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  8 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
  3 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0198937

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C1C(O)CC2C3CCC4C(=O)C(NC(=O)C=C(C)C)=CCC4(C)C3CCC12C)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H44N2O3/c1-16(2)14-24(32)29-22-11-13-27(4)19-10-12-28(5)21(18(19)8-9-20(27)26(22)33)15-23(31)25(28)17(3)30(6)7/h11,14,17-21,23,25,31H,8-10,12-13,15H2,1-7H3,(H,29,32)

> <INCHI_KEY>
ZYTVGXYHWPMUEB-UHFFFAOYSA-N

> <FORMULA>
C28H44N2O3

> <MOLECULAR_WEIGHT>
456.671

> <EXACT_MASS>
456.335193285

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
54.39239941407622

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{14-[1-(dimethylamino)ethyl]-13-hydroxy-2,15-dimethyl-6-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-5-yl}-3-methylbut-2-enamide

> <ALOGPS_LOGP>
4.06

> <JCHEM_LOGP>
3.6536106240000015

> <ALOGPS_LOGS>
-4.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.882294437450568

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.122685197681996

> <JCHEM_PKA_STRONGEST_BASIC>
9.070531360328275

> <JCHEM_POLAR_SURFACE_AREA>
69.64

> <JCHEM_REFRACTIVITY>
134.99529999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-{14-[1-(dimethylamino)ethyl]-13-hydroxy-2,15-dimethyl-6-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-5-yl}-3-methylbut-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-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  O   UNK     0       3.851  -2.645   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      14.377  -0.716   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      16.362  -3.071   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      16.832  -5.696   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      18.871  -3.977   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      19.864  -5.154   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.380  -4.883   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      19.341  -6.603   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       3.257  -5.652   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.676  -4.226   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   22                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   11   18   19                                             
CONECT   18   17                                                            
CONECT   19   17    8   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    3    7   23                                             
CONECT   23   22                                                            
CONECT   24   14   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31    2   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
N-{14-[1-(dimethylamino)ethyl]-13-hydroxy-2,15-dimethyl-6-oxotetracyclo[8.7.0.0,.0,]heptadec-4-en-5-yl}-3-methylbut-2-enimidate	Generator
N-{14-[1-(dimethylamino)ethyl]-13-hydroxy-2,15-dimethyl-6-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-5-yl}-3-methylbut-2-enimidate	Generator

Chemical Formula

C₂₈H₄₄N₂O₃

Average Mass

456.6710 Da

Monoisotopic Mass

456.33519 Da

IUPAC Name

N-{14-[1-(dimethylamino)ethyl]-13-hydroxy-2,15-dimethyl-6-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-5-yl}-3-methylbut-2-enamide

Traditional Name

N-{14-[1-(dimethylamino)ethyl]-13-hydroxy-2,15-dimethyl-6-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-5-yl}-3-methylbut-2-enamide

CAS Registry Number

Not Available

SMILES

CC(C1C(O)CC2C3CCC4C(=O)C(NC(=O)C=C(C)C)=CCC4(C)C3CCC12C)N(C)C

InChI Identifier

InChI=1S/C28H44N2O3/c1-16(2)14-24(32)29-22-11-13-27(4)19-10-12-28(5)21(18(19)8-9-20(27)26(22)33)15-23(31)25(28)17(3)30(6)7/h11,14,17-21,23,25,31H,8-10,12-13,15H2,1-7H3,(H,29,32)

InChI Key

ZYTVGXYHWPMUEB-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 oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

Oxosteroids

Alternative Parents

Substituents

22-azasteroid
Pregnane-skeleton
Pregnane-type alkaloid
Steroidal alkaloid
Hydroxysteroid
Oxosteroid
4-oxosteroid
16-hydroxysteroid
Azasteroid
Alkaloid or derivatives
Cyclohexenone
N-acyl-amine
Cyclic alcohol
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxamide group
Ketone
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Organic nitrogen compound
Alcohol
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Amine
Organic oxygen compound
Carbonyl group
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	4.06	ALOGPS
logP	3.65	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	13.12	ChemAxon
pKa (Strongest Basic)	9.07	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.64 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	135 m³·mol⁻¹	ChemAxon
Polarizability	54.39 Å³	ChemAxon
Number of Rings	4	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

75244639

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]-2-hydroxy-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl}-3-methylbut-2-enimidic acid (NP0198937)

MOL for NP0198937 (n-{1-[1-(dimethylamino)ethyl]-2-hydroxy-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl}-3-methylbut-2-enimidic acid)

3D MOL for NP0198937 (n-{1-[1-(dimethylamino)ethyl]-2-hydroxy-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl}-3-methylbut-2-enimidic acid)

3D SDF for NP0198937 (n-{1-[1-(dimethylamino)ethyl]-2-hydroxy-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl}-3-methylbut-2-enimidic acid)

3D-SDF for NP0198937 (n-{1-[1-(dimethylamino)ethyl]-2-hydroxy-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl}-3-methylbut-2-enimidic acid)

PDB for NP0198937 (n-{1-[1-(dimethylamino)ethyl]-2-hydroxy-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl}-3-methylbut-2-enimidic acid)

3D PDB for NP0198937 (n-{1-[1-(dimethylamino)ethyl]-2-hydroxy-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl}-3-methylbut-2-enimidic acid)

SMILES for NP0198937 (n-{1-[1-(dimethylamino)ethyl]-2-hydroxy-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl}-3-methylbut-2-enimidic acid)

INCHI for NP0198937 (n-{1-[1-(dimethylamino)ethyl]-2-hydroxy-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl}-3-methylbut-2-enimidic acid)

Structure for NP0198937 (n-{1-[1-(dimethylamino)ethyl]-2-hydroxy-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl}-3-methylbut-2-enimidic acid)

3D Structure for NP0198937 (n-{1-[1-(dimethylamino)ethyl]-2-hydroxy-9a,11a-dimethyl-6-oxo-1h,2h,3h,3ah,3bh,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl}-3-methylbut-2-enimidic acid)