NP-MRD: Showing NP-Card for (+)-Buxabenzamidienine (NP0067667)

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Record Information

Version

1.0

Created at

2022-04-28 12:30:35 UTC

Updated at

2022-04-28 12:30:35 UTC

NP-MRD ID

NP0067667

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Buxabenzamidienine

Description

Buxabenzamidienine belongs to the class of organic compounds known as buxus alkaloids. These are alkaloids with a triterpenoid-steroid pregnane type structure with C-4 methyl groups, a 9beta,10beta-cycloartenol system, and a degraded C-20 side chain. Structurally, they are derivatives of either a 9beta,10beta-cyclo-4,4,14alpha-trimethyl-5alpha-pregnane or a 9(10->19)abeo 4,4,14alpha-trimethyl-5alpha-pregnane system. (+)-Buxabenzamidienine is found in Buxus papillosa, Buxus papilosa and Buxus sempervirens. It was first documented in 2011 (PMID: 22050684). Based on a literature review very few articles have been published on Buxabenzamidienine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214302D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282214302D          

 36 40  0  0  1  0            999 V2000
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   -0.2144   -1.9585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061   -2.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5124   -3.1887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9164   -3.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9081   -4.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6184   -4.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3370   -4.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3453   -3.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6350   -2.7978    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  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  6  1  6  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  4  1  1  0  0  0
 14 15  1  0  0  0  0
  1 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 10 26  1  6  0  0  0
  9 27  1  1  0  0  0
  1 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067667

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]([C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4C(CC[C@H](NC(=O)C5=CC=CC=C5)C4(C)C)=CC3=CC[C@]12C)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C33H48N2O/c1-22(35(6)7)26-18-20-33(5)28-15-14-27-24(21-25(28)17-19-32(26,33)4)13-16-29(31(27,2)3)34-30(36)23-11-9-8-10-12-23/h8-12,17,21-22,26-29H,13-16,18-20H2,1-7H3,(H,34,36)/t22-,26+,27+,28+,29-,32+,33-/m0/s1

> <INCHI_KEY>
PDEYVCIISSAEBG-DVSQZFJSSA-N

> <FORMULA>
C33H48N2O

> <MOLECULAR_WEIGHT>
488.76

> <EXACT_MASS>
488.376664174

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
61.26600163495008

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(6S,8R,11R,12S,15S,16R)-15-[(1S)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethyltetracyclo[9.7.0.0^{3,8}.0^{12,16}]octadeca-1(18),2-dien-6-yl]benzamide

> <ALOGPS_LOGP>
6.96

> <JCHEM_LOGP>
6.430706290000001

> <ALOGPS_LOGS>
-6.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.090403157879553

> <JCHEM_PKA_STRONGEST_BASIC>
10.29940528697761

> <JCHEM_POLAR_SURFACE_AREA>
32.34

> <JCHEM_REFRACTIVITY>
152.60409999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.91e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(6S,8R,11R,12S,15S,16R)-15-[(1S)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethyltetracyclo[9.7.0.0^{3,8}.0^{12,16}]octadeca-1(18),2-dien-6-yl]benzamide

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       0.926  -2.872   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.910  -1.333   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.236  -0.549   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.577  -1.306   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.772  -0.333   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.276  -0.661   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.131   0.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.668   0.520   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.350  -0.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.495  -2.141   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.959  -2.042   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.304  -3.436   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.806  -3.794   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.593  -2.846   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.267  -3.629   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.004  -4.981   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.558  -4.996   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.450  -3.350   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.894  -2.816   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.832  -1.277   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.041  -0.323   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.819   1.201   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      13.472  -0.893   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      14.681   0.061   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.694  -2.417   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.779  -3.505   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.334   0.324   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      -0.400  -3.656   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      -0.385  -5.196   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.957  -5.952   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.711  -5.979   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.695  -7.519   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.021  -8.302   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.362  -7.546   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.378  -6.006   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -3.052  -5.223   0.000  0.00  0.00           C+0
CONECT    1    2   15   28                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   20   27                                             
CONECT   10    9   11   18   26                                             
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    4   15                                                  
CONECT   15   14    1   16   17                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   10   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    9   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   10                                                            
CONECT   27    9                                                            
CONECT   28    1   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₈N₂O

Average Mass

488.7600 Da

Monoisotopic Mass

488.37666 Da

IUPAC Name

N-[(6S,8R,11R,12S,15S,16R)-15-[(1S)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethyltetracyclo[9.7.0.0^{3,8}.0^{12,16}]octadeca-1(18),2-dien-6-yl]benzamide

Traditional Name

N-[(6S,8R,11R,12S,15S,16R)-15-[(1S)-1-(dimethylamino)ethyl]-7,7,12,16-tetramethyltetracyclo[9.7.0.0^{3,8}.0^{12,16}]octadeca-1(18),2-dien-6-yl]benzamide

CAS Registry Number

Not Available

SMILES

C[C@@H]([C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4C(CC[C@H](NC(=O)C5=CC=CC=C5)C4(C)C)=CC3=CC[C@]12C)N(C)C

InChI Identifier

InChI=1S/C33H48N2O/c1-22(35(6)7)26-18-20-33(5)28-15-14-27-24(21-25(28)17-19-32(26,33)4)13-16-29(31(27,2)3)34-30(36)23-11-9-8-10-12-23/h8-12,17,21-22,26-29H,13-16,18-20H2,1-7H3,(H,34,36)/t22-,26+,27+,28+,29-,32+,33-/m0/s1

InChI Key

PDEYVCIISSAEBG-DVSQZFJSSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 papillosa	LOTUS Database	35616633
Buxus papilosa	Plant	KNApSAcK
Buxus sempervirens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as buxus alkaloids. These are alkaloids with a triterpenoid-steroid pregnane type structure with C-4 methyl groups, a 9beta,10beta-cycloartenol system, and a degraded C-20 side chain. Structurally, they are derivatives of either a 9beta,10beta-cyclo-4,4,14alpha-trimethyl-5alpha-pregnane or a 9(10->19)abeo 4,4,14alpha-trimethyl-5alpha-pregnane system.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

Buxus alkaloids

Alternative Parents

Substituents

Abeo-9(10->19)-4,4-14(alpha)-trimethyl-5(alpha)-pregnane-skeleton
Abeoabietane diterpenoid
Diterpenoid
Benzamide
Benzoic acid or derivatives
Benzoyl
Benzenoid
Monocyclic benzene moiety
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Hydrocarbon derivative
Organic nitrogen compound
Amine
Organic oxygen compound
Organic oxide
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	6.96	ALOGPS
logP	6.43	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	15.09	ChemAxon
pKa (Strongest Basic)	10.3	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	4	ChemAxon
Refractivity	152.6 m³·mol⁻¹	ChemAxon
Polarizability	61.27 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00025468

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

101606430

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Orhan IE, Khan MT, Erdem SA, Kartal M, Sener B: Selective cholinesterase inhibitors from Buxus sempervirens L. and their molecular docking studies. Curr Comput Aided Drug Des. 2011 Dec;7(4):276-86. doi: 10.2174/157340911798260296. [PubMed:22050684 ]

Showing NP-Card for (+)-Buxabenzamidienine (NP0067667)

MOL for NP0067667 ((+)-Buxabenzamidienine)

3D MOL for NP0067667 ((+)-Buxabenzamidienine)

3D SDF for NP0067667 ((+)-Buxabenzamidienine)

3D-SDF for NP0067667 ((+)-Buxabenzamidienine)

PDB for NP0067667 ((+)-Buxabenzamidienine)

3D PDB for NP0067667 ((+)-Buxabenzamidienine)

SMILES for NP0067667 ((+)-Buxabenzamidienine)

INCHI for NP0067667 ((+)-Buxabenzamidienine)

Structure for NP0067667 ((+)-Buxabenzamidienine)

3D Structure for NP0067667 ((+)-Buxabenzamidienine)