NP-MRD: Showing NP-Card for (R)-Methyl-5-(1-methylethyl)-1-nitro-1,3-cyclohexadiene (NP0057758)

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Record Information

Version

2.0

Created at

2022-04-28 03:09:36 UTC

Updated at

2022-04-28 03:09:36 UTC

NP-MRD ID

NP0057758

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(R)-Methyl-5-(1-methylethyl)-1-nitro-1,3-cyclohexadiene

Description

(R)-2-Nitro-p-mentha-1,5-diene belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes (R)-2-Nitro-p-mentha-1,5-diene is possibly neutral. Outside of the human body, (R)-2-Nitro-p-mentha-1,5-diene has been detected, but not quantified in, a few different foods, such as fats and oils, green vegetables, and herbs and spices. (R)-Methyl-5-(1-methylethyl)-1-nitro-1,3-cyclohexadiene is found in Angelica archangelica . This could make (R)-2-nitro-p-mentha-1,5-diene a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 28  0  0  0  0  0  0  0  0999 V2000
    2.8882   -2.1452   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7691   -1.1279   -0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199   -0.6138    0.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9541   -1.0752    2.2112 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.5845   -2.1040    2.7967 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9905   -0.3196    2.6911 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.2283    0.3896    1.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3558    0.7958   -0.1889 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8447    0.6774   -0.3011 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6241    1.4806    0.6745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2729    1.0882   -1.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2175    0.1603   -1.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829   -0.7159   -1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7654   -1.7508    0.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446   -2.3331   -1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5228   -3.1009    0.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6942    1.2554    1.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4933   -0.0323    1.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1195    1.8990   -0.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1592   -0.3945   -0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6900    1.1799    0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6132    2.5814    0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3592    1.2947    1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6422    1.9407   -2.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2386    0.2187   -2.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3174    1.4557   -1.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2186    0.4663   -2.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5866   -1.1703   -2.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  3  1  0
  3  2  2  0
  2  1  1  0
  2 13  1  0
 13 12  2  0
  3  4  1  0
  4  6  1  0
  4  5  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 12  8  1  0
  8 19  1  6
  7 17  1  0
  7 18  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
 13 28  1  0
 12 27  1  0
  9 20  1  1
 10 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
 11 26  1  0
M  CHG  2   4   1   6  -1
M  END


  Mrv0541 02241208552D          

 14 14  0  0  0  0            999 V2000
    4.1545   -4.0661    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8689   -3.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8689   -2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1545   -2.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1545   -1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4400   -2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4400   -3.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1545   -4.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4400   -5.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8689   -5.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8690   -4.4786    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5834   -2.4161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5834   -1.5911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2978   -2.8286    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  1  7  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  1 11  1  1  0  0  0
  3 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0057758

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC(=C(C)C=C1)N(=O)=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C10H15NO2/c1-7(2)9-5-4-8(3)10(6-9)11(12)13/h4-5,7,9H,6H2,1-3H3/t9-/m1/s1

> <INCHI_KEY>
RIPRCNJJZGOFLC-SECBINFHSA-N

> <FORMULA>
C10H15NO2

> <MOLECULAR_WEIGHT>
181.2316

> <EXACT_MASS>
181.110278729

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
19.851299973159158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R)-2-methyl-1-nitro-5-(propan-2-yl)cyclohexa-1,3-diene

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
2.3865950443333337

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
45.82

> <JCHEM_REFRACTIVITY>
54.19200000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-5-isopropyl-2-methyl-1-nitrocyclohexa-1,3-diene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       7.755  -7.590   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.089  -6.820   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.089  -5.280   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.755  -4.510   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.755  -2.970   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.421  -5.280   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.421  -6.820   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.755  -9.130   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.421  -9.900   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.089  -9.900   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       9.089  -8.360   0.000  0.00  0.00           H+0
HETATM   12  N   UNK     0      10.422  -4.510   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0      10.422  -2.970   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      11.756  -5.280   0.000  0.00  0.00           O+0
CONECT    1    2    7    8   11                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    1                                                       
CONECT    8    1    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    1                                                            
CONECT   12    3   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₅NO₂

Average Mass

181.2316 Da

Monoisotopic Mass

181.11028 Da

IUPAC Name

(5R)-2-methyl-1-nitro-5-(propan-2-yl)cyclohexa-1,3-diene

Traditional Name

(5R)-5-isopropyl-2-methyl-1-nitrocyclohexa-1,3-diene

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC(=C(C)C=C1)N(=O)=O)C(C)C

InChI Identifier

InChI=1S/C10H15NO2/c1-7(2)9-5-4-8(3)10(6-9)11(12)13/h4-5,7,9H,6H2,1-3H3/t9-/m1/s1

InChI Key

RIPRCNJJZGOFLC-SECBINFHSA-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
Angelica archangelica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Organic nitro compound
C-nitro compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxoazanium
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	2.37	ALOGPS
logP	2.39	ChemAxon
logS	-2.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	45.82 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	54.19 m³·mol⁻¹	ChemAxon
Polarizability	19.85 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

HMDB0036090

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014929

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

131751912

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (R)-Methyl-5-(1-methylethyl)-1-nitro-1,3-cyclohexadiene (NP0057758)

MOL for NP0057758 ((R)-Methyl-5-(1-methylethyl)-1-nitro-1,3-cyclohexadiene)

3D MOL for NP0057758 ((R)-Methyl-5-(1-methylethyl)-1-nitro-1,3-cyclohexadiene)

3D SDF for NP0057758 ((R)-Methyl-5-(1-methylethyl)-1-nitro-1,3-cyclohexadiene)

3D-SDF for NP0057758 ((R)-Methyl-5-(1-methylethyl)-1-nitro-1,3-cyclohexadiene)

PDB for NP0057758 ((R)-Methyl-5-(1-methylethyl)-1-nitro-1,3-cyclohexadiene)

3D PDB for NP0057758 ((R)-Methyl-5-(1-methylethyl)-1-nitro-1,3-cyclohexadiene)

SMILES for NP0057758 ((R)-Methyl-5-(1-methylethyl)-1-nitro-1,3-cyclohexadiene)

INCHI for NP0057758 ((R)-Methyl-5-(1-methylethyl)-1-nitro-1,3-cyclohexadiene)

Structure for NP0057758 ((R)-Methyl-5-(1-methylethyl)-1-nitro-1,3-cyclohexadiene)

3D Structure for NP0057758 ((R)-Methyl-5-(1-methylethyl)-1-nitro-1,3-cyclohexadiene)