NP-MRD: Showing NP-Card for n-[(1e)-2-(4-methoxyphenyl)ethenyl]carboximidic acid (NP0223816)

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Record Information

Version

2.0

Created at

2022-09-06 02:01:14 UTC

Updated at

2022-09-06 02:01:15 UTC

NP-MRD ID

NP0223816

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(1e)-2-(4-methoxyphenyl)ethenyl]carboximidic acid

Description

Tuberin belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Tuberin is a very strong basic compound (based on its pKa). In humans, tuberin is involved in leucine stimulation on insulin signaling. Outside of the human body, Tuberin has been detected, but not quantified in, alcoholic beverages and potato. This could make tuberin a potential biomarker for the consumption of these foods. Hamartin coded by the gene TSC1 functions as a facilitator of Hsp90 in chaperoning of Tuberin, therefore preventing its ubiquitination and degradation in the proteasome. The defective degradation of glycogen by the autophagy-lysosome pathway is, at least in part, independent of impaired regulation of mTORC1 and is restored by the combined use of PKB/Akt and mTORC1 pharmacological inhibitors. Pharmacological inhibition of ERK1/2 restores GSK3β activity and protein synthesis levels in a model of tuberous sclerosis. Mutations in TSC2 can cause Lymphangioleiomyomatosis, a disease caused by the enlargement of tissue in the lungs, creating cysts and tumours and causing difficulty breathing. Because Tuberin regulates cell size, along with the protein Hamartin, mutations to TSC1 and TSC2 genes may prevent the control of cell growth in the lungs of individuals. TSC2 functions within a multi-protein complex knowns as the TSC complex which consists of the core proteins TSC2, TSC1, and TBC1D7. Defects in the autophagy-lysosome pathway are associated with excessive ubiquitination and degradation of LC3 and LAMP1/2 proteins. Cells from individuals with pathogenic mutations in the TSC2 gene display depletion of lysosomes, impairment of autophagy, and abnormal accumulation of glycogen. Mutations in this gene lead to tuberous sclerosis. Its gene product is believed to be a tumor suppressor and is able to stimulate specific GTPases. n-[(1e)-2-(4-methoxyphenyl)ethenyl]carboximidic acid is found in Haplophyllum tuberculatum and Streptomyces amakusaensis. Alternative splicing results in multiple transcript variants encoding different isoforms of the protein.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533007131513542D          

 15 15  0  0  0  0            999 V2000
   -0.0000    2.4750    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
    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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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
   -0.0000   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   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
    1.4289   -1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  6  2  0  0  0  0
  9  2  2  0  0  0  0
  9  3  1  0  0  0  0
  9  6  1  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  2  0  0  0  0
  8 12  1  4  0  0  0
 13  1  1  0  0  0  0
 13 10  1  0  0  0  0
 14  6  1  0  0  0  0
 15  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223816

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(N=CO)=C(\[H])C1=CC=C(OC)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO2/c1-13-10-4-2-9(3-5-10)6-7-11-8-12/h2-8H,1H3,(H,11,12)/b7-6+

> <INCHI_KEY>
SZCZSKMCTGEJKI-VOTSOKGWSA-N

> <FORMULA>
C10H11NO2

> <MOLECULAR_WEIGHT>
177.203

> <EXACT_MASS>
177.078978598

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.19249472576978

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(E)-2-(4-methoxyphenyl)ethenyl]carboximidic acid

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
-0.7304886923112932

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.534078508922205

> <JCHEM_PKA_STRONGEST_BASIC>
11.894450315343734

> <JCHEM_POLAR_SURFACE_AREA>
41.82000000000001

> <JCHEM_REFRACTIVITY>
51.31770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(E)-2-(4-methoxyphenyl)ethenyl]carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -0.000   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  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -0.000  -4.620   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0       2.667  -3.080   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0      -1.334  -2.310   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2    4    9                                                       
CONECT    3    5    9                                                       
CONECT    4    2   10                                                       
CONECT    5    3   10                                                       
CONECT    6    7    9   14                                                  
CONECT    7    6   11   15                                                  
CONECT    8   11   12                                                       
CONECT    9    2    3    6                                                  
CONECT   10    4    5   13                                                  
CONECT   11    7    8                                                       
CONECT   12    8                                                            
CONECT   13    1   10                                                       
CONECT   14    6                                                            
CONECT   15    7                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
Tuberous sclerosis 2 protein	MeSH
Tuberin	MeSH
Tuberous sclerosis 2 protein, human	MeSH
Tuberous sclerosis 2 protein, mouse	MeSH
TSC2 Protein, rat	MeSH
TSC2 Protein, human	MeSH
Tuberin protein, human	MeSH
TSC2 Protein, mouse	MeSH
Tuberous sclerosis 2 protein, rat	MeSH
Tuberous sclerosis complex 2 protein	MeSH

Chemical Formula

C₁₀H₁₁NO₂

Average Mass

177.2030 Da

Monoisotopic Mass

177.07898 Da

IUPAC Name

N-[(E)-2-(4-methoxyphenyl)ethenyl]carboximidic acid

Traditional Name

N-[(E)-2-(4-methoxyphenyl)ethenyl]carboximidic acid

CAS Registry Number

Not Available

SMILES

[H]\C(N=CO)=C(\[H])C1=CC=C(OC)C=C1

InChI Identifier

InChI=1S/C10H11NO2/c1-13-10-4-2-9(3-5-10)6-7-11-8-12/h2-8H,1H3,(H,11,12)/b7-6+

InChI Key

SZCZSKMCTGEJKI-VOTSOKGWSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Haplophyllum tuberculatum	LOTUS Database	35616633
Streptomyces aMAKUSAENSIS	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Anisole
Methoxybenzene
Styrene
Alkyl aryl ether
Monocyclic benzene moiety
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Ether
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic 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	2.31	ALOGPS
logP	-0.73	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	-2.5	ChemAxon
pKa (Strongest Basic)	11.89	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	3	ChemAxon
Refractivity	51.32 m³·mol⁻¹	ChemAxon
Polarizability	19.19 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

FDB017898

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

TSC2

METLIN ID

Not Available

PubChem Compound

5352006

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[(1e)-2-(4-methoxyphenyl)ethenyl]carboximidic acid (NP0223816)

MOL for NP0223816 (n-[(1e)-2-(4-methoxyphenyl)ethenyl]carboximidic acid)

3D MOL for NP0223816 (n-[(1e)-2-(4-methoxyphenyl)ethenyl]carboximidic acid)

3D SDF for NP0223816 (n-[(1e)-2-(4-methoxyphenyl)ethenyl]carboximidic acid)

3D-SDF for NP0223816 (n-[(1e)-2-(4-methoxyphenyl)ethenyl]carboximidic acid)

PDB for NP0223816 (n-[(1e)-2-(4-methoxyphenyl)ethenyl]carboximidic acid)

3D PDB for NP0223816 (n-[(1e)-2-(4-methoxyphenyl)ethenyl]carboximidic acid)

SMILES for NP0223816 (n-[(1e)-2-(4-methoxyphenyl)ethenyl]carboximidic acid)

INCHI for NP0223816 (n-[(1e)-2-(4-methoxyphenyl)ethenyl]carboximidic acid)

Structure for NP0223816 (n-[(1e)-2-(4-methoxyphenyl)ethenyl]carboximidic acid)

3D Structure for NP0223816 (n-[(1e)-2-(4-methoxyphenyl)ethenyl]carboximidic acid)