NP-MRD: Showing NP-Card for 3,5-Dimethoxytoluene (NP0085710)

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Record Information

Version

2.0

Created at

2022-04-29 06:11:26 UTC

Updated at

2022-04-29 06:11:26 UTC

NP-MRD ID

NP0085710

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,5-Dimethoxytoluene

Description

3,5-Dimethoxytoluene, also known as DMT or orcinol dimethyl ether, belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups. 3,5-Dimethoxytoluene is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,5-Dimethoxytoluene is found in Ligusticum jeholense and Solanum peruvianum. 3,5-Dimethoxytoluene was first documented in 2002 (PMID: 12123815). These are organic compounds contaiing a methoxybenzene or a derivative thereof (PMID: 12177504) (PMID: 16361520) (PMID: 18413608) (PMID: 23973758).

Structure

MOL 3D MOL SDF PDB SMILES InChI

77844
  Mrv0541 12191221372D          

 23 23  0  0  0  0            999 V2000
    1.6500   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.4620    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.5428    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9215    0.4620    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2522   -1.4742    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -1.2870    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7637   -0.5883    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1385   -1.8563    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.3678    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1615   -1.8563    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0493    1.4133    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    2.1120    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5378    2.2992    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1 10  1  0  0  0  0
  2  5  1  0  0  0  0
  2 11  1  0  0  0  0
  3  6  2  0  0  0  0
  3  7  1  0  0  0  0
  3  9  1  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  2  0  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8 14  1  0  0  0  0
  9 15  1  0  0  0  0
  9 16  1  0  0  0  0
  9 17  1  0  0  0  0
 10 18  1  0  0  0  0
 10 19  1  0  0  0  0
 10 20  1  0  0  0  0
 11 21  1  0  0  0  0
 11 22  1  0  0  0  0
 11 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085710

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C(OC([H])([H])[H])C([H])=C(C([H])=C1OC([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C9H12O2/c1-7-4-8(10-2)6-9(5-7)11-3/h4-6H,1-3H3

> <INCHI_KEY>
RIZBLVRXRWHLFA-UHFFFAOYSA-N

> <FORMULA>
C9H12O2

> <MOLECULAR_WEIGHT>
152.1904

> <EXACT_MASS>
152.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
16.83841989566584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3-dimethoxy-5-methylbenzene

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
2.171324674

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.534991701295333

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
44.0256

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3-dimethoxy-5-methylbenzene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-DEC-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 77844                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-DEC-12         0                                  
HETATM    1  O   UNK     0       3.080  -1.925   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.747   2.695   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.081  -1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.414  -1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.747   1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081   0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747  -1.925   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414   0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415  -1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080  -3.465   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   3.465   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       7.908   0.862   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0       5.747  -2.880   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0       3.587   0.862   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       7.937  -2.752   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       9.242  -2.402   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       8.892  -1.098   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       2.125  -3.465   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       3.080  -4.420   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       4.035  -3.465   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       7.559   2.638   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       7.908   3.942   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       6.604   4.292   0.000  0.00  0.00           H+0
CONECT    1    4   10                                                       
CONECT    2    5   11                                                       
CONECT    3    6    7    9                                                  
CONECT    4    1    7    8                                                  
CONECT    5    2    6    8                                                  
CONECT    6    3    5   12                                                  
CONECT    7    3    4   13                                                  
CONECT    8    4    5   14                                                  
CONECT    9    3   15   16   17                                             
CONECT   10    1   18   19   20                                             
CONECT   11    2   21   22   23                                             
CONECT   12    6                                                            
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16    9                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   10                                                            
CONECT   20   10                                                            
CONECT   21   11                                                            
CONECT   22   11                                                            
CONECT   23   11                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Value	Source
1,5-Dimethoxy-3-methylbenzene	ChEBI
5-Methylresorcinol dimethyl ether	ChEBI
DMT	ChEBI
Orcinol dimethyl ether	ChEBI

Chemical Formula

C₉H₁₂O₂

Average Mass

152.1904 Da

Monoisotopic Mass

152.08373 Da

IUPAC Name

1,3-dimethoxy-5-methylbenzene

Traditional Name

1,3-dimethoxy-5-methylbenzene

CAS Registry Number

Not Available

SMILES

[H]C1=C(OC([H])([H])[H])C([H])=C(C([H])=C1OC([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C9H12O2/c1-7-4-8(10-2)6-9(5-7)11-3/h4-6H,1-3H3

InChI Key

RIZBLVRXRWHLFA-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
Ligusticum jeholense	Plant	KNApSAcK
Solanum peruvianum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Methoxybenzenes

Direct Parent

Dimethoxybenzenes

Alternative Parents

Substituents

M-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Phenol ether
Anisole
Toluene
Alkyl aryl ether
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

a small molecule (CPD-9502 )

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	2.53	ALOGPS
logP	2.17	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.03 m³·mol⁻¹	ChemAxon
Polarizability	16.84 Å³	ChemAxon
Number of Rings	1	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

HMDB0059853

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

CPD-9502

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

77844

PDB ID

Not Available

ChEBI ID

141217

Good Scents ID

Not Available

References

General References

Scalliet G, Journot N, Jullien F, Baudino S, Magnard JL, Channeliere S, Vergne P, Dumas C, Bendahmane M, Cock JM, Hugueney P: Biosynthesis of the major scent components 3,5-dimethoxytoluene and 1,3,5-trimethoxybenzene by novel rose O-methyltransferases. FEBS Lett. 2002 Jul 17;523(1-3):113-8. doi: 10.1016/s0014-5793(02)02956-3. [PubMed:12123815 ]
Lavid N, Wang J, Shalit M, Guterman I, Bar E, Beuerle T, Menda N, Shafir S, Zamir D, Adam Z, Vainstein A, Weiss D, Pichersky E, Lewinsohn E: O-methyltransferases involved in the biosynthesis of volatile phenolic derivatives in rose petals. Plant Physiol. 2002 Aug;129(4):1899-907. doi: 10.1104/pp.005330. [PubMed:12177504 ]
Scalliet G, Lionnet C, Le Bechec M, Dutron L, Magnard JL, Baudino S, Bergougnoux V, Jullien F, Chambrier P, Vergne P, Dumas C, Cock JM, Hugueney P: Role of petal-specific orcinol O-methyltransferases in the evolution of rose scent. Plant Physiol. 2006 Jan;140(1):18-29. doi: 10.1104/pp.105.070961. Epub 2005 Dec 16. [PubMed:16361520 ]
Scalliet G, Piola F, Douady CJ, Rety S, Raymond O, Baudino S, Bordji K, Bendahmane M, Dumas C, Cock JM, Hugueney P: Scent evolution in Chinese roses. Proc Natl Acad Sci U S A. 2008 Apr 15;105(15):5927-32. doi: 10.1073/pnas.0711551105. Epub 2008 Apr 14. [PubMed:18413608 ]
Li C, Xu F, Cao C, Shang MY, Zhang CY, Yu J, Liu GX, Wang X, Cai SQ: Comparative analysis of two species of Asari Radix et Rhizoma by electronic nose, headspace GC-MS and chemometrics. J Pharm Biomed Anal. 2013 Nov;85:231-8. doi: 10.1016/j.jpba.2013.07.034. Epub 2013 Aug 7. [PubMed:23973758 ]

Showing NP-Card for 3,5-Dimethoxytoluene (NP0085710)

MOL for NP0085710 (3,5-Dimethoxytoluene)

3D MOL for NP0085710 (3,5-Dimethoxytoluene)

3D SDF for NP0085710 (3,5-Dimethoxytoluene)

3D-SDF for NP0085710 (3,5-Dimethoxytoluene)

PDB for NP0085710 (3,5-Dimethoxytoluene)

3D PDB for NP0085710 (3,5-Dimethoxytoluene)

SMILES for NP0085710 (3,5-Dimethoxytoluene)

INCHI for NP0085710 (3,5-Dimethoxytoluene)

Structure for NP0085710 (3,5-Dimethoxytoluene)

3D Structure for NP0085710 (3,5-Dimethoxytoluene)