NP-MRD: Showing NP-Card for Musk ambrette (NP0085934)

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Record Information

Version

2.0

Created at

2022-04-29 06:21:16 UTC

Updated at

2022-04-29 06:21:16 UTC

NP-MRD ID

NP0085934

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Musk ambrette

Description

1-Tert-butyl-2-methoxy-4-methyl-3,5-dinitrobenzene belongs to the class of organic compounds known as dinitrotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and exactly two nitro groups. Musk ambrette is found in Piper nigrum and Senegalia berlandieri. 1-Tert-butyl-2-methoxy-4-methyl-3,5-dinitrobenzene is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 35  0  0  0  0  0  0  0  0999 V2000
   -0.3028   -2.7356    1.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1346   -2.1238   -0.0016 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056   -0.8142   -0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5090    0.2745   -0.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9852    0.1293   -0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6015    1.5392   -0.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5624   -0.4596    1.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4824   -0.6417   -1.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0973    1.5199   -0.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4594    1.7105   -0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0115    3.0147   -0.3610 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.1102    3.1413   -0.9345 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4165    4.1458    0.1394 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.2348    0.5769   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7238    0.7216   -0.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7069   -0.6930   -0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5408   -1.8318    0.0159 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.6540   -2.5725   -0.9664 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2206   -2.1421    1.1458 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.2210   -2.0508    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4980   -3.5133    1.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2956   -3.2318    1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3301    2.0014   -1.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4025    2.1673    0.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7131    1.3392   -0.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8386   -0.3597    1.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5171    0.1039    1.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8596   -1.5137    0.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5464   -0.3283   -1.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9023   -0.2996   -2.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4899   -1.7209   -1.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800    2.3775   -0.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849    1.4786    0.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1085    1.0021   -1.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2012   -0.2116    0.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 16  2  0
 16 14  1  0
 14 15  1  0
 14 10  2  0
 10  9  1  0
  9  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  5  8  1  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
 16 17  1  0
 17 19  1  0
 17 18  2  0
  4  3  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
  9 32  1  0
  6 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
M  CHG  4  11   1  13  -1  17   1  19  -1
M  END


  Mrv1533004171520002D          

 19 19  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  5  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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
M  CHG  4  14   1  16  -1  17   1  19  -1
M  END
> <DATABASE_ID>
NP0085934

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C(C)=C(C=C1C(C)(C)C)[N+]([O-])=O)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N2O5/c1-7-9(13(15)16)6-8(12(2,3)4)11(19-5)10(7)14(17)18/h6H,1-5H3

> <INCHI_KEY>
SUAUILGSCPYJCS-UHFFFAOYSA-N

> <FORMULA>
C12H16N2O5

> <MOLECULAR_WEIGHT>
268.269

> <EXACT_MASS>
268.105921623

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
26.172574733086137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-tert-butyl-2-methoxy-4-methyl-3,5-dinitrobenzene

> <ALOGPS_LOGP>
3.32

> <JCHEM_LOGP>
3.754020589

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.017804863452627

> <JCHEM_POLAR_SURFACE_AREA>
95.51

> <JCHEM_REFRACTIVITY>
68.86929999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-tert-butyl-2-methoxy-4-methyl-3,5-dinitrobenzene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.564   3.644   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.104   0.976   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+1
HETATM   15  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O-1
HETATM   17  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+1
HETATM   18  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    7   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    4   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
Musk ambrette	MeSH
Musk ambrette (artificial)	MeSH
2-Methoxy-3,5-dinitro-4-methyl-t-butylbenzene	MeSH

Chemical Formula

C₁₂H₁₆N₂O₅

Average Mass

268.2690 Da

Monoisotopic Mass

268.10592 Da

IUPAC Name

1-tert-butyl-2-methoxy-4-methyl-3,5-dinitrobenzene

Traditional Name

1-tert-butyl-2-methoxy-4-methyl-3,5-dinitrobenzene

CAS Registry Number

Not Available

SMILES

COC1=C(C(C)=C(C=C1C(C)(C)C)[N+]([O-])=O)[N+]([O-])=O

InChI Identifier

InChI=1S/C12H16N2O5/c1-7-9(13(15)16)6-8(12(2,3)4)11(19-5)10(7)14(17)18/h6H,1-5H3

InChI Key

SUAUILGSCPYJCS-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, 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
Piper nigrum L.	Plant	KNApSAcK
Senegalia berlandieri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dinitrotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and exactly two nitro groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Toluenes

Direct Parent

Dinitrotoluenes

Alternative Parents

Substituents

Dinitrotoluene
Nitrophenyl ether
Nitrobenzene
Methoxyaniline
Phenylpropane
Phenoxy compound
Nitroaromatic compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
C-nitro compound
Organic nitro compound
Ether
Organic oxoazanium
Organic 1,3-dipolar compound
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organonitrogen compound
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

C-nitro compound (CHEBI:82495 )

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	3.32	ALOGPS
logP	3.75	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	95.51 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.87 m³·mol⁻¹	ChemAxon
Polarizability	26.17 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C19461

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6753

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Musk ambrette (NP0085934)

MOL for NP0085934 (Musk ambrette)

3D MOL for NP0085934 (Musk ambrette)

3D SDF for NP0085934 (Musk ambrette)

3D-SDF for NP0085934 (Musk ambrette)

PDB for NP0085934 (Musk ambrette)

3D PDB for NP0085934 (Musk ambrette)

SMILES for NP0085934 (Musk ambrette)

INCHI for NP0085934 (Musk ambrette)

Structure for NP0085934 (Musk ambrette)

3D Structure for NP0085934 (Musk ambrette)