NP-MRD: Showing NP-Card for n-[(1s,2r,5s,7s,10s,11s,14s,15r,16s,17r,18s,20s,23s)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracosan-7-yl]carboximidic acid (NP0252049)

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Record Information

Version

2.0

Created at

2022-09-07 15:26:31 UTC

Updated at

2022-09-07 15:26:32 UTC

NP-MRD ID

NP0252049

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(1s,2r,5s,7s,10s,11s,14s,15r,16s,17r,18s,20s,23s)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracosan-7-yl]carboximidic acid

Description

N-[(1S,2R,5S,7S,10S,11S,14S,15R,16S,17R,18S,20S,23S)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]Tetracosan-7-yl]carboximidic acid belongs to the class of organic compounds known as solanidines and derivatives. These are steroids with a structure based on the solanidane skeleton. Solanidane arises from the conversion of a cholestane side-chain into a bicyclic system. n-[(1s,2r,5s,7s,10s,11s,14s,15r,16s,17r,18s,20s,23s)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracosan-7-yl]carboximidic acid is found in Solanum pubescens. Based on a literature review very few articles have been published on N-[(1S,2R,5S,7S,10S,11S,14S,15R,16S,17R,18S,20S,23S)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]Tetracosan-7-yl]carboximidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072217262D          

 32 37  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309072217262D          

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    7.5368   -4.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9865   -3.3461    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4420   -2.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  9  7  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
 20 21  1  4  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 12 29  1  0  0  0  0
  9 29  1  0  0  0  0
 29 30  1  1  0  0  0
 10 31  1  1  0  0  0
  6 31  1  6  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252049

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H]2[C@@H](O)C[C@H](C)CN2[C@H]2C[C@H]3[C@@H]4CC[C@H]5C[C@H](CC[C@]5(C)[C@H]4CC[C@]3(C)[C@@H]12)N=CO

> <INCHI_IDENTIFIER>
InChI=1S/C28H46N2O2/c1-16-11-24(32)26-17(2)25-23(30(26)14-16)13-22-20-6-5-18-12-19(29-15-31)7-9-27(18,3)21(20)8-10-28(22,25)4/h15-26,32H,5-14H2,1-4H3,(H,29,31)/t16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26+,27-,28-/m0/s1

> <INCHI_KEY>
FFBKXNVIQQUUJG-NFADKULFSA-N

> <FORMULA>
C28H46N2O2

> <MOLECULAR_WEIGHT>
442.688

> <EXACT_MASS>
442.355928729

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.468501338072755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(1S,2R,5S,7S,10S,11S,14S,15R,16S,17R,18S,20S,23S)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{15,23}.0^{17,22}]tetracosan-7-yl]carboximidic acid

> <JCHEM_LOGP>
1.7227588896042985

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.607734694291537

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.779460885417543

> <JCHEM_PKA_STRONGEST_BASIC>
12.860752092048488

> <JCHEM_POLAR_SURFACE_AREA>
56.06000000000001

> <JCHEM_REFRACTIVITY>
128.50139999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-[(1S,2R,5S,7S,10S,11S,14S,15R,16S,17R,18S,20S,23S)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{15,23}.0^{17,22}]tetracosan-7-yl]carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       7.632  -4.234   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.648  -5.391   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.154  -6.849   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.171  -8.006   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.677  -9.465   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.681  -7.705   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.916  -8.625   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.897 -10.165   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.172  -7.735   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.715  -6.265   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.972  -5.375   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.206  -6.296   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.716  -5.994   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.210  -4.535   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.720  -4.234   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.737  -5.391   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.247  -5.089   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.263  -6.246   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      23.773  -5.944   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      24.790  -7.102   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      26.300  -6.800   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      21.769  -7.705   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.259  -8.006   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.243  -6.849   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.749  -8.308   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.733  -7.151   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.239  -8.610   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.729  -8.911   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.712  -7.754   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.069  -9.153   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      11.175  -6.246   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0      10.158  -5.089   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   31                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   29                                                  
CONECT   10    9   11   31                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   29                                                  
CONECT   13   12   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   18   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   16   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   13   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   12    9   30                                             
CONECT   30   29                                                            
CONECT   31   10    6   32                                                  
CONECT   32   31    2                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Value	Source
N-[(1S,2R,5S,7S,10S,11S,14S,15R,16S,17R,18S,20S,23S)-18-Hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0,.0,.0,.0,]tetracosan-7-yl]carboximidate	Generator

Chemical Formula

C₂₈H₄₆N₂O₂

Average Mass

442.6880 Da

Monoisotopic Mass

442.35593 Da

IUPAC Name

N-[(1S,2R,5S,7S,10S,11S,14S,15R,16S,17R,18S,20S,23S)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{15,23}.0^{17,22}]tetracosan-7-yl]carboximidic acid

Traditional Name

N-[(1S,2R,5S,7S,10S,11S,14S,15R,16S,17R,18S,20S,23S)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{15,23}.0^{17,22}]tetracosan-7-yl]carboximidic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H]2[C@@H](O)C[C@H](C)CN2[C@H]2C[C@H]3[C@@H]4CC[C@H]5C[C@H](CC[C@]5(C)[C@H]4CC[C@]3(C)[C@@H]12)N=CO

InChI Identifier

InChI=1S/C28H46N2O2/c1-16-11-24(32)26-17(2)25-23(30(26)14-16)13-22-20-6-5-18-12-19(29-15-31)7-9-27(18,3)21(20)8-10-28(22,25)4/h15-26,32H,5-14H2,1-4H3,(H,29,31)/t16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26+,27-,28-/m0/s1

InChI Key

FFBKXNVIQQUUJG-NFADKULFSA-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
Solanum pubescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as solanidines and derivatives. These are steroids with a structure based on the solanidane skeleton. Solanidane arises from the conversion of a cholestane side-chain into a bicyclic system.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

Solanidines and derivatives

Alternative Parents

Substituents

Solanidane skeleton
23-hydroxysteroid
Hydroxysteroid
Azasteroid
Indolizidine
Alkaloid or derivatives
Piperidine
N-alkylpyrrolidine
Pyrrolidine
1,2-aminoalcohol
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Carboximidic acid derivative
Carboximidic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	1.72	ChemAxon
pKa (Strongest Acidic)	-2.8	ChemAxon
pKa (Strongest Basic)	12.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	56.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	128.5 m³·mol⁻¹	ChemAxon
Polarizability	54.47 Å³	ChemAxon
Number of Rings	6	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

163060580

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,2r,5s,7s,10s,11s,14s,15r,16s,17r,18s,20s,23s)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracosan-7-yl]carboximidic acid (NP0252049)

MOL for NP0252049 (n-[(1s,2r,5s,7s,10s,11s,14s,15r,16s,17r,18s,20s,23s)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracosan-7-yl]carboximidic acid)

3D MOL for NP0252049 (n-[(1s,2r,5s,7s,10s,11s,14s,15r,16s,17r,18s,20s,23s)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracosan-7-yl]carboximidic acid)

3D SDF for NP0252049 (n-[(1s,2r,5s,7s,10s,11s,14s,15r,16s,17r,18s,20s,23s)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracosan-7-yl]carboximidic acid)

3D-SDF for NP0252049 (n-[(1s,2r,5s,7s,10s,11s,14s,15r,16s,17r,18s,20s,23s)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracosan-7-yl]carboximidic acid)

PDB for NP0252049 (n-[(1s,2r,5s,7s,10s,11s,14s,15r,16s,17r,18s,20s,23s)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracosan-7-yl]carboximidic acid)

3D PDB for NP0252049 (n-[(1s,2r,5s,7s,10s,11s,14s,15r,16s,17r,18s,20s,23s)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracosan-7-yl]carboximidic acid)

SMILES for NP0252049 (n-[(1s,2r,5s,7s,10s,11s,14s,15r,16s,17r,18s,20s,23s)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracosan-7-yl]carboximidic acid)

INCHI for NP0252049 (n-[(1s,2r,5s,7s,10s,11s,14s,15r,16s,17r,18s,20s,23s)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracosan-7-yl]carboximidic acid)

Structure for NP0252049 (n-[(1s,2r,5s,7s,10s,11s,14s,15r,16s,17r,18s,20s,23s)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracosan-7-yl]carboximidic acid)

3D Structure for NP0252049 (n-[(1s,2r,5s,7s,10s,11s,14s,15r,16s,17r,18s,20s,23s)-18-hydroxy-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracosan-7-yl]carboximidic acid)