NP-MRD: Showing NP-Card for n-[(1s,3r,6s,8r,11s,12s,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]-n-methylacetamide (NP0267628)

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Record Information

Version

2.0

Created at

2022-09-08 12:28:07 UTC

Updated at

2022-09-08 12:28:07 UTC

NP-MRD ID

NP0267628

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(1s,3r,6s,8r,11s,12s,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]-n-methylacetamide

Description

Buxaline C belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. n-[(1s,3r,6s,8r,11s,12s,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]-n-methylacetamide is found in Buxus sempervirens. Based on a literature review very few articles have been published on Buxaline C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082214282D          

 32 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309082214282D          

 32 36  0  0  1  0            999 V2000
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  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11 10  1  1  0  0  0
  9 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  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 29 28  1  1  0  0  0
  9 29  1  0  0  0  0
 29 30  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0267628

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]([C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CC[C@H](N(C)C(C)=O)C4(C)C)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H50N2O/c1-19(30(7)8)21-12-14-27(6)23-11-10-22-25(3,4)24(31(9)20(2)32)13-15-28(22)18-29(23,28)17-16-26(21,27)5/h19,21-24H,10-18H2,1-9H3/t19-,21+,22-,23-,24-,26+,27-,28+,29-/m0/s1

> <INCHI_KEY>
CGIJRUQDEIZDPN-WIOFQDPXSA-N

> <FORMULA>
C29H50N2O

> <MOLECULAR_WEIGHT>
442.732

> <EXACT_MASS>
442.392314238

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
55.37776270792015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(1S,3R,6S,8R,11S,12S,15S,16R)-15-[(1S)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-yl]-N-methylacetamide

> <JCHEM_LOGP>
4.858597887333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.299874184293813

> <JCHEM_POLAR_SURFACE_AREA>
23.550000000000004

> <JCHEM_REFRACTIVITY>
133.07629999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-[(1S,3R,6S,8R,11S,12S,15S,16R)-15-[(1S)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-yl]-N-methylacetamide

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.404  -3.802   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.888  -3.531   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.105  -4.708   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      -0.365  -2.082   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -1.357  -0.905   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.151  -1.811   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.675  -0.363   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.191  -0.092   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.183  -1.269   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.707   0.179   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.699  -0.998   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.222   0.451   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.738   0.722   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.731  -0.456   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.403   0.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.270  -0.506   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.216   0.710   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.635   2.137   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      12.741   0.499   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      13.686   1.715   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.321  -0.927   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.698  -1.985   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.424  -2.849   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.208  -1.904   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.839  -3.399   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.692  -2.175   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.169  -3.624   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.653  -3.895   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.660  -2.717   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.144  -2.988   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.362  -4.513   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.002  -4.022   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   30                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   29                                             
CONECT   10    9   11                                                       
CONECT   11   10    9   12   26                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   24                                             
CONECT   15   14                                                            
CONECT   16   14   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   14   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   11   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    9   30                                                  
CONECT   30   29    6   31   32                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₅₀N₂O

Average Mass

442.7320 Da

Monoisotopic Mass

442.39231 Da

IUPAC Name

N-[(1S,3R,6S,8R,11S,12S,15S,16R)-15-[(1S)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-yl]-N-methylacetamide

Traditional Name

N-[(1S,3R,6S,8R,11S,12S,15S,16R)-15-[(1S)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-yl]-N-methylacetamide

CAS Registry Number

Not Available

SMILES

C[C@@H]([C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CC[C@H](N(C)C(C)=O)C4(C)C)N(C)C

InChI Identifier

InChI=1S/C29H50N2O/c1-19(30(7)8)21-12-14-27(6)23-11-10-22-25(3,4)24(31(9)20(2)32)13-15-28(22)18-29(23,28)17-16-26(21,27)5/h19,21-24H,10-18H2,1-9H3/t19-,21+,22-,23-,24-,26+,27-,28+,29-/m0/s1

InChI Key

CGIJRUQDEIZDPN-WIOFQDPXSA-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
Buxus sempervirens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
9(beta),19-cyclo-4,4-14(alpha)-trimethyl-5(alpha)-pregnane-skeleton
22-azasteroid
20-oxosteroid
Steroidal alkaloid
Oxosteroid
Steroid
Azasteroid
Alkaloid or derivatives
Acetamide
Tertiary carboxylic acid amide
Tertiary aliphatic amine
Tertiary amine
Carboxamide group
Amino acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	4.86	ChemAxon
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	3	ChemAxon
Refractivity	133.08 m³·mol⁻¹	ChemAxon
Polarizability	55.38 Å³	ChemAxon
Number of Rings	5	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

68027578

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101603153

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,3r,6s,8r,11s,12s,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]-n-methylacetamide (NP0267628)

MOL for NP0267628 (n-[(1s,3r,6s,8r,11s,12s,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]-n-methylacetamide)

3D MOL for NP0267628 (n-[(1s,3r,6s,8r,11s,12s,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]-n-methylacetamide)

3D SDF for NP0267628 (n-[(1s,3r,6s,8r,11s,12s,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]-n-methylacetamide)

3D-SDF for NP0267628 (n-[(1s,3r,6s,8r,11s,12s,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]-n-methylacetamide)

PDB for NP0267628 (n-[(1s,3r,6s,8r,11s,12s,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]-n-methylacetamide)

3D PDB for NP0267628 (n-[(1s,3r,6s,8r,11s,12s,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]-n-methylacetamide)

SMILES for NP0267628 (n-[(1s,3r,6s,8r,11s,12s,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]-n-methylacetamide)

INCHI for NP0267628 (n-[(1s,3r,6s,8r,11s,12s,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]-n-methylacetamide)

Structure for NP0267628 (n-[(1s,3r,6s,8r,11s,12s,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]-n-methylacetamide)

3D Structure for NP0267628 (n-[(1s,3r,6s,8r,11s,12s,15s,16r)-15-[(1s)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]-n-methylacetamide)