NP-MRD: Showing NP-Card for n-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}carboximidic acid (NP0234955)

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Record Information

Version

2.0

Created at

2022-09-06 17:18:58 UTC

Updated at

2022-09-06 17:18:58 UTC

NP-MRD ID

NP0234955

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}carboximidic acid

Description

N-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]Octadeca-1(18),2-dien-15-yl]ethyl}carboximidic acid 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. n-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}carboximidic acid is found in Buxus sempervirens. N-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]Octadeca-1(18),2-dien-15-yl]ethyl}carboximidic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161520442D          

 31 34  0  0  0  0            999 V2000
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M  END

     RDKit          3D

 75 78  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1533004161520442D          

 31 34  0  0  0  0            999 V2000
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 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0234955

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(NC=O)C1C(O)CC2(C)C3CCC4C(CCC(N(C)C)C4(C)C)=CC3=CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44N2O2/c1-17(28-16-30)24-22(31)15-27(5)21-10-9-20-18(14-19(21)12-13-26(24,27)4)8-11-23(29(6)7)25(20,2)3/h12,14,16-17,20-24,31H,8-11,13,15H2,1-7H3,(H,28,30)

> <INCHI_KEY>
KIKPXXYWOBPSRR-UHFFFAOYSA-N

> <FORMULA>
C27H44N2O2

> <MOLECULAR_WEIGHT>
428.661

> <EXACT_MASS>
428.340278665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.85159105353115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}formamide

> <ALOGPS_LOGP>
4.52

> <JCHEM_LOGP>
3.1826713436666663

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.077187098325904

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.831577225990266

> <JCHEM_PKA_STRONGEST_BASIC>
10.325511318643217

> <JCHEM_POLAR_SURFACE_AREA>
52.57

> <JCHEM_REFRACTIVITY>
129.01379999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.29e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}formamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -1.518  -7.007   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.740  -5.483   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -3.171  -4.913   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -4.379  -5.868   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.810  -5.298   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.531  -4.529   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.593  -2.990   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.874  -2.135   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.852  -2.456   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.806  -3.665   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.522  -2.301   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.343  -3.764   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.997  -2.370   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.495  -2.012   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.708  -2.961   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.724  -4.500   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.530  -5.473   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.025  -5.145   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.170  -6.426   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.633  -6.326   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.951  -4.946   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.033  -6.130   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.065  -5.257   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.391  -4.474   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.376  -2.934   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      10.701  -2.150   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      10.686  -0.610   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.043  -2.907   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.034  -2.177   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.744  -0.810   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.298  -0.825   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7   21                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12   21                                             
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   29                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    6   10   22                                             
CONECT   22   21                                                            
CONECT   23   16   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   25   15   30   31                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
N-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0,.0,]octadeca-1(18),2-dien-15-yl]ethyl}carboximidate	Generator
N-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}carboximidate	Generator

Chemical Formula

C₂₇H₄₄N₂O₂

Average Mass

428.6610 Da

Monoisotopic Mass

428.34028 Da

IUPAC Name

N-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}formamide

Traditional Name

N-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}formamide

CAS Registry Number

Not Available

SMILES

CC(NC=O)C1C(O)CC2(C)C3CCC4C(CCC(N(C)C)C4(C)C)=CC3=CCC12C

InChI Identifier

InChI=1S/C27H44N2O2/c1-17(28-16-30)24-22(31)15-27(5)21-10-9-20-18(14-19(21)12-13-26(24,27)4)8-11-23(29(6)7)25(20,2)3/h12,14,16-17,20-24,31H,8-11,13,15H2,1-7H3,(H,28,30)

InChI Key

KIKPXXYWOBPSRR-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
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
Cyclic alcohol
Amino acid or derivatives
Carboxamide group
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Alcohol
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
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	4.52	ALOGPS
logP	3.18	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	14.83	ChemAxon
pKa (Strongest Basic)	10.33	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.57 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	129.01 m³·mol⁻¹	ChemAxon
Polarizability	51.85 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

22297629

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-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}carboximidic acid (NP0234955)

MOL for NP0234955 (n-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}carboximidic acid)

3D MOL for NP0234955 (n-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}carboximidic acid)

3D SDF for NP0234955 (n-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}carboximidic acid)

3D-SDF for NP0234955 (n-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}carboximidic acid)

PDB for NP0234955 (n-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}carboximidic acid)

3D PDB for NP0234955 (n-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}carboximidic acid)

SMILES for NP0234955 (n-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}carboximidic acid)

INCHI for NP0234955 (n-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}carboximidic acid)

Structure for NP0234955 (n-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}carboximidic acid)

3D Structure for NP0234955 (n-{1-[6-(dimethylamino)-14-hydroxy-7,7,12,16-tetramethyltetracyclo[9.7.0.0³,⁸.0¹²,¹⁶]octadeca-1(18),2-dien-15-yl]ethyl}carboximidic acid)