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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:37 UTC

Update Date

2022-03-07 02:53:07 UTC

HMDB ID

HMDB0031811

Secondary Accession Numbers

HMDB31811

Metabolite Identification

Common Name

3,5-Dimethylphenyl methylcarbamate

Description

3,5-Dimethylphenyl methylcarbamate, also known as 3,5-xylenyl N-methylcarbamic acid or 3,5-XMC, belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group. Based on a literature review very few articles have been published on 3,5-Dimethylphenyl methylcarbamate.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652305261923582D          

 13 13  0  0  0  0            999 V2000
    0.7145    2.0625    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
   -1.4289   -2.4750    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
    0.0000    0.8250    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
    0.7145    1.2375    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
    0.0000    0.0000    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 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  7  4  2  0  0  0  0
  7  5  1  0  0  0  0
  8  2  1  0  0  0  0
  8  4  1  0  0  0  0
  8  6  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 11  3  1  4  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031811

> <DATABASE_NAME>
hmdb

> <SMILES>
CN=C(O)OC1=CC(C)=CC(C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H13NO2/c1-7-4-8(2)6-9(5-7)13-10(12)11-3/h4-6H,1-3H3,(H,11,12)

> <INCHI_KEY>
CVQODEWAPZVVBU-UHFFFAOYSA-N

> <FORMULA>
C10H13NO2

> <MOLECULAR_WEIGHT>
179.2157

> <EXACT_MASS>
179.094628665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.519968949088288

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(3,5-dimethylphenoxy)-N-methylmethanimidic acid

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
3.0064316578525783

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.157619618406315

> <JCHEM_PKA_STRONGEST_BASIC>
2.5948589673331637

> <JCHEM_POLAR_SURFACE_AREA>
41.82000000000001

> <JCHEM_REFRACTIVITY>
51.367900000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-3,5-dimethylphenoxy-N-methylmethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   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  N   UNK     0      -2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3   11                                                            
CONECT    4    7    8                                                       
CONECT    5    7    9                                                       
CONECT    6    8    9                                                       
CONECT    7    1    4    5                                                  
CONECT    8    2    4    6                                                  
CONECT    9    5    6   13                                                  
CONECT   10   11   12   13                                                  
CONECT   11    3   10                                                       
CONECT   12   10                                                            
CONECT   13    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0031811
HETATM    1  C1  UNL     1       2.811  -0.482   1.039  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.190  -0.834  -0.283  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.692  -0.320  -1.330  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.087  -0.681  -2.634  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.728   0.628  -1.161  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.492   0.385  -0.630  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.373   1.471  -0.496  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.630   1.339   0.021  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.529   2.513   0.155  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.115   0.119   0.441  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.284  -0.967   0.320  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.743  -2.312   0.754  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.001  -0.819  -0.211  1.00  0.00           C  
HETATM   14  H1  UNL     1       3.710  -0.266   1.685  1.00  0.00           H  
HETATM   15  H2  UNL     1       2.246   0.472   1.049  1.00  0.00           H  
HETATM   16  H3  UNL     1       2.186  -1.249   1.569  1.00  0.00           H  
HETATM   17  H4  UNL     1       3.879  -0.140  -3.008  1.00  0.00           H  
HETATM   18  H5  UNL     1      -0.035   2.424  -0.809  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.075   2.600  -0.816  1.00  0.00           H  
HETATM   20  H7  UNL     1      -3.276   2.393   0.959  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.926   3.439   0.242  1.00  0.00           H  
HETATM   22  H9  UNL     1      -3.108  -0.001   0.853  1.00  0.00           H  
HETATM   23  H10 UNL     1      -0.951  -2.803   1.381  1.00  0.00           H  
HETATM   24  H11 UNL     1      -2.687  -2.206   1.319  1.00  0.00           H  
HETATM   25  H12 UNL     1      -1.930  -2.993  -0.102  1.00  0.00           H  
HETATM   26  H13 UNL     1       0.639  -1.710  -0.306  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3
CONECT    3    4    5
CONECT    4   17
CONECT    5    6
CONECT    6    7    7   13
CONECT    7    8   18
CONECT    8    9   10   10
CONECT    9   19   20   21
CONECT   10   11   22
CONECT   11   12   13   13
CONECT   12   23   24   25
CONECT   13   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,5-Dimethylphenyl N-methylcarbamate	ChEBI
3,5-XMC	ChEBI
3,5-Xylenol, methylcarbamate	ChEBI
3,5-Xylenyl N-methylcarbamate	ChEBI
3,5-Xylyl methylcarbamate	ChEBI
3,5-Xylyl N-methylcarbamate	ChEBI
Methylcarbamic acid 3,5-xylyl ester	ChEBI
N-Methyl-3,5-xylyl carbamate	ChEBI
Cosban	Kegg
3,5-Dimethylphenyl N-methylcarbamic acid	Generator
3,5-Xylenol, methylcarbamic acid	Generator
3,5-Xylenyl N-methylcarbamic acid	Generator
3,5-Xylyl methylcarbamic acid	Generator
3,5-Xylyl N-methylcarbamic acid	Generator
Methylcarbamate 3,5-xylyl ester	Generator
N-Methyl-3,5-xylyl carbamic acid	Generator
3,5-Dimethylphenyl methylcarbamic acid	Generator
3,5-Dimethylphenol methylcarbamate	HMDB
3,5-Dimethylphenyl methylcarbamate (9ci)	HMDB
3,5-Xylyl methylcarbamate (8ci)	HMDB
3,5-Xylylester kyseliny methylkarbaminove	HMDB
Carbamic acid, methyl-, 3,5-xylyl ester	HMDB
Carbaron	HMDB
Macbal	HMDB
Maqbal	HMDB
Maqbarl	HMDB
Phenol, 3,5-dimethyl-, methylcarbamate	HMDB
Phenol, 3,5-dimethyl-, methylcarbamate (9ci)	HMDB
Profam	HMDB
XMC	HMDB
XMC (Pesticide)	HMDB
XMC, JMAF	HMDB

Chemical Formula

C₁₀H₁₃NO₂

Average Molecular Weight

179.2157

Monoisotopic Molecular Weight

179.094628665

IUPAC Name

1-(3,5-dimethylphenoxy)-N-methylmethanimidic acid

Traditional Name

1-3,5-dimethylphenoxy-N-methylmethanimidic acid

CAS Registry Number

2655-14-3

SMILES

CN=C(O)OC1=CC(C)=CC(C)=C1

InChI Identifier

InChI=1S/C10H13NO2/c1-7-4-8(2)6-9(5-7)13-10(12)11-3/h4-6H,1-3H3,(H,11,12)

InChI Key

CVQODEWAPZVVBU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenyl methylcarbamates

Direct Parent

Phenyl methylcarbamates

Alternative Parents

Substituents

Phenyl methylcarbamate
Phenoxy compound
M-xylene
Xylene
Carbamic acid ester
Carbonic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

carbamate ester (CHEBI:38571 )
Carbamate insecticides (C18771 )

Ontology

Physiological effect

Health effect

Circulatory system disorder

Vascular disorder

Hypertension (HMDB: HMDB0031811)
Hypotension (HMDB: HMDB0031811)

Blood and lymphatic system disorder

Hypoglycemia (HMDB: HMDB0031811)

Observation

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Mood disorder

Major depressive disorder (HMDB: HMDB0031811)

Neurotic, stress-related, or somatoform disorder

Anxiety (HMDB: HMDB0031811)

Coma (HMDB: HMDB0031811)

Disposition

Biological location

Cellular substructure

Route of exposure

Parenteral

Dermal (HMDB: HMDB0031811)
Inhalation (HMDB: HMDB0031811)

Enteral

Ingestion (HMDB: HMDB0031811)

Source

Endogenous

Endogenous (HMDB: HMDB0031811)

Exogenous

Food

Food (HMDB: HMDB0031811)

Synthetic

Synthetic (HMDB: HMDB0031811)

Exogenous (HMDB: HMDB0031811)

Process

Not Available

Role

Industrial application

Agrochemical (HMDB: HMDB0031811)

Agriculture

Pesticide

Carbamate insecticide (HMDB: HMDB0031811)

Biological role

Modulator

Inhibitor

EC 3.1.1.7 (acetylcholinesterase) inhibitor (HMDB: HMDB0031811)

Environmental role

Environmental contaminant (HMDB: HMDB0031811)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	99 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.47 mg/mL at 20 °C	Not Available
LogP	2.23	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.73 g/L	ALOGPS
logP	2.58	ALOGPS
logP	3.01	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.16	ChemAxon
pKa (Strongest Basic)	2.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.82 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	51.37 m³·mol⁻¹	ChemAxon
Polarizability	19.52 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	142.823	31661259
DarkChem	[M-H]-	140.833	31661259
DeepCCS	[M+H]+	139.456	30932474
DeepCCS	[M-H]-	136.566	30932474
DeepCCS	[M-2H]-	173.302	30932474
DeepCCS	[M+Na]+	148.841	30932474
AllCCS	[M+H]+	137.6	32859911
AllCCS	[M+H-H2O]+	133.4	32859911
AllCCS	[M+NH4]+	141.6	32859911
AllCCS	[M+Na]+	142.7	32859911
AllCCS	[M-H]-	139.2	32859911
AllCCS	[M+Na-2H]-	140.1	32859911
AllCCS	[M+HCOO]-	141.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	4.65 minutes	32390414
Predicted by Siyang on May 30, 2022	12.8024 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.52 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1506.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	394.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	147.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	241.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	148.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	534.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	627.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	90.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1077.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	402.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1401.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	320.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	371.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	350.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	168.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	47.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,5-Dimethylphenyl methylcarbamate	CN=C(O)OC1=CC(C)=CC(C)=C1	2384.7	Standard polar	33892256
3,5-Dimethylphenyl methylcarbamate	CN=C(O)OC1=CC(C)=CC(C)=C1	1550.0	Standard non polar	33892256
3,5-Dimethylphenyl methylcarbamate	CN=C(O)OC1=CC(C)=CC(C)=C1	1550.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,5-Dimethylphenyl methylcarbamate,1TMS,isomer #1	CN=C(OC1=CC(C)=CC(C)=C1)O[Si](C)(C)C	1511.1	Semi standard non polar	33892256
3,5-Dimethylphenyl methylcarbamate,1TBDMS,isomer #1	CN=C(OC1=CC(C)=CC(C)=C1)O[Si](C)(C)C(C)(C)C	1727.7	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008485

KNApSAcK ID

Not Available

Chemspider ID

16606

KEGG Compound ID

C18771

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

17563

PDB ID

Not Available

ChEBI ID

38571

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 3,5-Dimethylphenyl methylcarbamate (HMDB0031811)

MOL for HMDB0031811 (3,5-Dimethylphenyl methylcarbamate)

3D MOL for HMDB0031811 (3,5-Dimethylphenyl methylcarbamate)

3D SDF for HMDB0031811 (3,5-Dimethylphenyl methylcarbamate)

3D-SDF for HMDB0031811 (3,5-Dimethylphenyl methylcarbamate)

PDB for HMDB0031811 (3,5-Dimethylphenyl methylcarbamate)

3D PDB for HMDB0031811 (3,5-Dimethylphenyl methylcarbamate)

SMILES for HMDB0031811 (3,5-Dimethylphenyl methylcarbamate)

INCHI for HMDB0031811 (3,5-Dimethylphenyl methylcarbamate)

Structure for HMDB0031811 (3,5-Dimethylphenyl methylcarbamate)

3D Structure for HMDB0031811 (3,5-Dimethylphenyl methylcarbamate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized