NP-MRD: Showing NP-Card for n-[(1s,3as,3br,5as,7r,8s,9as,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-8-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]benzenecarboximidic acid (NP0219578)

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Record Information

Version

2.0

Created at

2022-09-05 20:37:33 UTC

Updated at

2022-09-05 20:37:33 UTC

NP-MRD ID

NP0219578

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(1s,3as,3br,5as,7r,8s,9as,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-8-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]benzenecarboximidic acid

Description

CHEMBL343365 belongs to the class of organic compounds known as hydroxysteroids. Hydroxysteroids are compounds containing an steroid backbone, with at least one hydrogen substituted by a hydroxyl group. n-[(1s,3as,3br,5as,7r,8s,9as,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-8-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]benzenecarboximidic acid is found in Sarcococca saligna. Based on a literature review very few articles have been published on CHEMBL343365.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052222372D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309052222372D          

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    1.4338   -2.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  4  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 10 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
  7 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  3 30  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  1  0  0  0
  2 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219578

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]([C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](N=C(O)C5=CC=CC=C5)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H46N2O2/c1-19(32(4)5)23-13-14-24-22-12-11-21-17-26(31-28(34)20-9-7-6-8-10-20)27(33)18-30(21,3)25(22)15-16-29(23,24)2/h6-10,19,21-27,33H,11-18H2,1-5H3,(H,31,34)/t19-,21-,22-,23+,24-,25-,26+,27-,29+,30-/m0/s1

> <INCHI_KEY>
XIHQWIIPJIXLEO-FXHHUKKCSA-N

> <FORMULA>
C30H46N2O2

> <MOLECULAR_WEIGHT>
466.71

> <EXACT_MASS>
466.355928729

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
57.374600025863344

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(1S,2S,4S,5R,7S,10R,11S,14S,15S)-14-[(1S)-1-(dimethylamino)ethyl]-4-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]benzenecarboximidic acid

> <JCHEM_LOGP>
3.978062275392675

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
14.583060854529464

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.598845371144709

> <JCHEM_PKA_STRONGEST_BASIC>
10.30899776038205

> <JCHEM_POLAR_SURFACE_AREA>
56.06000000000001

> <JCHEM_REFRACTIVITY>
139.3166

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-[(1S,2S,4S,5R,7S,10R,11S,14S,15S)-14-[(1S)-1-(dimethylamino)ethyl]-4-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]benzenecarboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         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  N   UNK     0      16.362  -3.071   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      16.832  -5.696   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      18.871  -3.977   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.394  -2.529   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.910  -2.257   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.903  -3.435   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.380  -4.883   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.864  -5.154   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       3.257  -5.652   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.676  -4.226   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4   30                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   25                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   12   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   10   26   27                                             
CONECT   26   25                                                            
CONECT   27   25    7   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    3    6   31                                             
CONECT   31   30                                                            
CONECT   32    2   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₆N₂O₂

Average Mass

466.7100 Da

Monoisotopic Mass

466.35593 Da

IUPAC Name

N-[(1S,2S,4S,5R,7S,10R,11S,14S,15S)-14-[(1S)-1-(dimethylamino)ethyl]-4-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]benzenecarboximidic acid

Traditional Name

N-[(1S,2S,4S,5R,7S,10R,11S,14S,15S)-14-[(1S)-1-(dimethylamino)ethyl]-4-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]benzenecarboximidic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]([C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](N=C(O)C5=CC=CC=C5)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C)N(C)C

InChI Identifier

InChI=1S/C30H46N2O2/c1-19(32(4)5)23-13-14-24-22-12-11-21-17-26(31-28(34)20-9-7-6-8-10-20)27(33)18-30(21,3)25(22)15-16-29(23,24)2/h6-10,19,21-27,33H,11-18H2,1-5H3,(H,31,34)/t19-,21-,22-,23+,24-,25-,26+,27-,29+,30-/m0/s1

InChI Key

XIHQWIIPJIXLEO-FXHHUKKCSA-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 hydroxysteroids. Hydroxysteroids are compounds containing an steroid backbone, with at least one hydrogen substituted by a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

Hydroxysteroids

Alternative Parents

Substituents

22-azasteroid
Pregnane-skeleton
Steroidal alkaloid
Pregnane-type alkaloid
2-hydroxysteroid
Hydroxysteroid
Azasteroid
Benzamide
Benzoic acid or derivatives
Alkaloid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Amino acid or derivatives
Tertiary aliphatic amine
Carboxamide group
Tertiary amine
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Alcohol
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen 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	3.98	ChemAxon
pKa (Strongest Acidic)	8.6	ChemAxon
pKa (Strongest Basic)	10.31	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	56.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	139.32 m³·mol⁻¹	ChemAxon
Polarizability	57.37 Å³	ChemAxon
Number of Rings	5	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

9038881

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10863593

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[(1s,3as,3br,5as,7r,8s,9as,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-8-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]benzenecarboximidic acid (NP0219578)

MOL for NP0219578 (n-[(1s,3as,3br,5as,7r,8s,9as,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-8-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]benzenecarboximidic acid)

3D MOL for NP0219578 (n-[(1s,3as,3br,5as,7r,8s,9as,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-8-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]benzenecarboximidic acid)

3D SDF for NP0219578 (n-[(1s,3as,3br,5as,7r,8s,9as,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-8-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]benzenecarboximidic acid)

3D-SDF for NP0219578 (n-[(1s,3as,3br,5as,7r,8s,9as,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-8-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]benzenecarboximidic acid)

PDB for NP0219578 (n-[(1s,3as,3br,5as,7r,8s,9as,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-8-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]benzenecarboximidic acid)

3D PDB for NP0219578 (n-[(1s,3as,3br,5as,7r,8s,9as,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-8-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]benzenecarboximidic acid)

SMILES for NP0219578 (n-[(1s,3as,3br,5as,7r,8s,9as,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-8-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]benzenecarboximidic acid)

INCHI for NP0219578 (n-[(1s,3as,3br,5as,7r,8s,9as,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-8-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]benzenecarboximidic acid)

Structure for NP0219578 (n-[(1s,3as,3br,5as,7r,8s,9as,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-8-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]benzenecarboximidic acid)

3D Structure for NP0219578 (n-[(1s,3as,3br,5as,7r,8s,9as,9bs,11as)-1-[(1s)-1-(dimethylamino)ethyl]-8-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]benzenecarboximidic acid)