NP-MRD: Showing NP-Card for Promecarb (NP0045105)

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Record Information

Version

1.0

Created at

2022-03-10 18:58:03 UTC

Updated at

2022-03-10 22:22:14 UTC

NP-MRD ID

NP0045105

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Promecarb

Description

Promecarb, also known as 3-methyl-5-(1-methylethyl)-Phenol methylcarbamate, belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group. Promecarb is a very weakly acidic compound (based on its pKa). It is an odorless, colorless, crystalline solid and it was used as a non-systemic contact insecticide. Promecarb is a carbamate pesticide. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment (https://Journals.Flvc.Org/edis/article/view/114999). Promecarb is no longer approved for sale or use in the USA. Promecarb's mechanism of action is through the inhibition of the enzyme acetylcholine esterase. Acetylcholine esterase (ACE) is an enzyme that breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions; its breakdown allows the muscle or organ to relax. The inhibition of ACE results in the accumulation of acetyl choline at motor nerves synapses, causing overstimulation of the nicotinic and muscarinic receptors at the neuromuscular junction. Promecarb has also been detected as a volatile component of cannabis samples obtained in police seizures (PMID: 26657499 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 32  0  0  0  0  0  0  0  0999 V2000
    5.0742   -1.5966   -0.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0207   -0.9497   -1.1606 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8196   -0.4972   -0.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6587   -0.6627    0.6925 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8212    0.1192   -1.2815 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.5566   -0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670    1.8428   -0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5892    2.2863    0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6785    3.6644    1.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6395    1.3925    0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5912    0.1162    0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7865   -0.7658    0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1889   -1.1352   -1.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4647   -2.0419    0.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4254   -0.3070   -0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0789   -1.3276   -0.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9589   -2.6942   -0.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9357   -1.3414    0.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1306   -0.8030   -2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4155    2.5106   -0.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4427    4.3558    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7054    3.8939    1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0245    3.8269    1.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5450    1.7807    1.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5919   -0.2349    0.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7943   -0.2987   -1.6831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7790   -2.0722   -1.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2424   -1.2419   -1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4238   -2.5812    1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0674   -1.7767    1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8101   -2.7022    0.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -1.3158   -0.9748 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 15  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 15  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  7 20  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 15 32  1  0
 12 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
M  END


  Mrv1652303202019002D          

 15 15  0  0  0  0            999 V2000
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  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
    2.1434   -0.4125    0.0000 O   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
    0.7145   -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
   -0.7145   -0.4125    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045105

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H17NO2/c1-8(2)10-5-9(3)6-11(7-10)15-12(14)13-4/h5-8H,1-4H3,(H,13,14)

> <INCHI_KEY>
DTAPQAJKAFRNJB-UHFFFAOYSA-N

> <FORMULA>
C12H17NO2

> <MOLECULAR_WEIGHT>
207.2689

> <EXACT_MASS>
207.125928793

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
23.656515803484258

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methyl-5-(propan-2-yl)phenyl N-methylcarbamate

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
3.229067862333333

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.771932067943105

> <JCHEM_POLAR_SURFACE_AREA>
38.33

> <JCHEM_REFRACTIVITY>
59.995799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-isopropyl-5-methylphenyl N-methylcarbamate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667   0.000   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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11    6                                                       
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
3-Methyl-5-isopropylphenyl N-methylcarbamate	MeSH
Carbamult	MeSH
m-Cym-5-yl methylcarbamate	MeSH
3-Cym-5-yl methylcarbamate	MeSH

Chemical Formula

C₁₂H₁₇NO₂

Average Mass

207.2689 Da

Monoisotopic Mass

207.12593 Da

IUPAC Name

3-methyl-5-(propan-2-yl)phenyl N-methylcarbamate

Traditional Name

3-isopropyl-5-methylphenyl N-methylcarbamate

CAS Registry Number

2631-37-0

SMILES

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

InChI Identifier

InChI=1S/C12H17NO2/c1-8(2)10-5-9(3)6-11(7-10)15-12(14)13-4/h5-8H,1-4H3,(H,13,14)

InChI Key

DTAPQAJKAFRNJB-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
Cannabis sativa	NULL	Not Available

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
Cumene
Phenylpropane
Phenoxy compound
Toluene
Carbamic acid ester
Carbonic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

alkylbenzene (CHEBI:82096 )
Carbamate insecticide (C18956 )

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	2.82	ALOGPS
logP	3.23	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	14.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60 m³·mol⁻¹	ChemAxon
Polarizability	23.66 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C18956

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Promecarb

METLIN ID

Not Available

PubChem Compound

17516

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Showing NP-Card for Promecarb (NP0045105)

MOL for NP0045105 (Promecarb)

3D MOL for NP0045105 (Promecarb)

3D SDF for NP0045105 (Promecarb)

3D-SDF for NP0045105 (Promecarb)

PDB for NP0045105 (Promecarb)

3D PDB for NP0045105 (Promecarb)

SMILES for NP0045105 (Promecarb)

INCHI for NP0045105 (Promecarb)

Structure for NP0045105 (Promecarb)

3D Structure for NP0045105 (Promecarb)