NP-MRD: Showing NP-Card for n-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid (NP0199673)

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Record Information

Version

2.0

Created at

2022-09-04 18:21:33 UTC

Updated at

2022-09-04 18:21:33 UTC

NP-MRD ID

NP0199673

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid

Description

(±)-Tembamide, also known as tembamide, belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring (±)-Tembamide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (±)-Tembamide has been detected, but not quantified in, fruits. n-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid is found in Aegle marmelos, Clausena brevistyla, Feroniella lucida, Limonia acidissima and Zanthoxylum ailanthoides. This could make (±)-tembamide a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    6.8618    0.3509   -0.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0562   -0.2163   -1.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6660   -0.0517   -1.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8159   -0.5792   -1.9741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4387   -0.4095   -1.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8861    0.2828   -0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4163    0.4509   -0.6981 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0647    1.7491   -0.4326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1235   -0.5751    0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5488   -0.6554    0.3226 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4465    0.3524    0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0273    1.4912    1.0656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8830    0.1359    0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7193    1.2526    0.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0703    1.0546    0.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6329   -0.2046    0.8050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8084   -1.2794    0.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4128   -1.1374    0.6720 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7126    0.8085    0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0953    0.6375    0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9270    0.3132   -0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5930    1.4261    0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6424   -0.1635    0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2512   -1.1279   -2.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073   -0.8369   -2.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0522    0.2306   -1.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5426    2.0815    0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2867   -0.3167    1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3487   -1.5393    0.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9604   -1.5913    0.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2809    2.2463    0.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7052    1.9344    0.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7064   -0.3108    0.8315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2410   -2.2769    0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8034   -2.0282    0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2883    1.3459    0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7215    1.0697    0.8092 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
  4  5  1  0
  5  6  2  0
  6 19  1  0
 19 20  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 20  3  1  0
 18 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
 19 36  1  0
 20 37  1  0
  7 26  1  6
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
M  END


  Mrv0541 02241220052D          

 20 21  0  0  0  0            999 V2000
   -0.7215   -1.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433   -1.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433   -0.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7215   -0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004   -0.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004   -1.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6413   -1.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3631   -1.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3631   -0.4002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0850   -0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0850    0.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3631    1.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3631    2.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0850    2.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8068    2.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8068    1.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0850   -0.0008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8068   -0.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7215   -2.4054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8068   -0.4002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 17  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 19  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 20  2  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0199673

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C(O)CNC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO3/c1-20-14-9-7-12(8-10-14)15(18)11-17-16(19)13-5-3-2-4-6-13/h2-10,15,18H,11H2,1H3,(H,17,19)

> <INCHI_KEY>
NICURWGAEFHESQ-UHFFFAOYSA-N

> <FORMULA>
C16H17NO3

> <MOLECULAR_WEIGHT>
271.3111

> <EXACT_MASS>
271.120843415

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.471029721360935

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzamide

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.9840290856666671

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.070812949099984

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.051203449322479

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9408619444151541

> <JCHEM_POLAR_SURFACE_AREA>
58.559999999999995

> <JCHEM_REFRACTIVITY>
77.07140000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzamide

> <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      -1.347  -2.993   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.694  -2.244   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.694  -0.747   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.347  -0.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.001  -0.747   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.001  -2.244   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.197  -2.993   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.544  -2.244   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.544  -0.747   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.892  -0.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.892   1.496   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.544   2.244   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.544   3.741   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.892   4.490   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.239   3.741   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.239   2.244   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.892  -0.001   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.239  -0.747   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.347  -4.490   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.239  -0.747   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   20                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   11   15                                                       
CONECT   17    3   18                                                       
CONECT   18   17                                                            
CONECT   19    7                                                            
CONECT   20   10                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
Tembamide	HMDB
N-[2-Hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidate	Generator

Chemical Formula

C₁₆H₁₇NO₃

Average Mass

271.3111 Da

Monoisotopic Mass

271.12084 Da

IUPAC Name

N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzamide

Traditional Name

N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzamide

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C(O)CNC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H17NO3/c1-20-14-9-7-12(8-10-14)15(18)11-17-16(19)13-5-3-2-4-6-13/h2-10,15,18H,11H2,1H3,(H,17,19)

InChI Key

NICURWGAEFHESQ-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, 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
Aegle marmelos	LOTUS Database	35616633
Clausena brevistyla	LOTUS Database	35616633
Feroniella lucida	LOTUS Database	35616633
Limonia acidissima	LOTUS Database	35616633
Zanthoxylum ailanthoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzamides

Alternative Parents

Substituents

Benzamide
Anisole
Benzoyl
Phenol ether
Methoxybenzene
Phenoxy compound
Alkyl aryl ether
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Ether
Carboxylic acid derivative
Aromatic alcohol
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen 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	1.87	ALOGPS
logP	1.98	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	14.05	ChemAxon
pKa (Strongest Basic)	-0.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.07 m³·mol⁻¹	ChemAxon
Polarizability	29.47 Å³	ChemAxon
Number of Rings	2	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

HMDB0030639

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002544

KNApSAcK ID

Not Available

Chemspider ID

154600

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

177583

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid (NP0199673)

MOL for NP0199673 (n-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)

3D MOL for NP0199673 (n-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)

3D SDF for NP0199673 (n-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)

3D-SDF for NP0199673 (n-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)

PDB for NP0199673 (n-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)

3D PDB for NP0199673 (n-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)

SMILES for NP0199673 (n-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)

INCHI for NP0199673 (n-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)

Structure for NP0199673 (n-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)

3D Structure for NP0199673 (n-[2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)