NP-MRD: Showing NP-Card for n-[(2r)-2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid (NP0207537)

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Record Information

Version

2.0

Created at

2022-09-05 04:11:01 UTC

Updated at

2022-09-05 04:11:01 UTC

NP-MRD ID

NP0207537

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(R)-Tembamide belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring. n-[(2r)-2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid is found in Clausena brevistyla, Feroniella lucida and Zanthoxylum fagara. n-[(2r)-2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid was first documented in 2019 (PMID: 30900703). Based on a literature review very few articles have been published on (R)-Tembamide.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    6.7540    0.3020    0.2684 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0036   -0.7052   -0.3770 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6422   -0.5594   -0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234    0.5445    0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6530    0.6692   -0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8738   -0.2828   -0.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4236   -0.1577   -0.8118 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1425   -1.3942   -0.4784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1753    0.8806    0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083    0.8766   -0.1246 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4175    0.1111    0.5013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9884   -0.7981    1.4672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8340    0.1771    0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7523   -0.6229    0.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1038   -0.5557    0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5363    0.3389   -0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6336    1.1317   -1.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2854    1.0622   -0.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5123   -1.3899   -1.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9021   -1.5289   -1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6379    1.2675   -0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3062    0.4840    1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8231    0.0171    0.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5911    1.3061    0.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1747    1.5303    0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1858    0.1445   -1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3536   -1.7226    0.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1819    1.9016   -0.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0221    0.6625    1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201   -0.5410    2.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4577   -1.3409    1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8113   -1.1797    1.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5781    0.4003   -0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9575    1.8327   -1.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5928    1.6980   -1.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9573   -2.1714   -1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4174   -2.3882   -1.4992 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  2  0
 11 12  1  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
 12 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


  Mrv1652309052206112D          

 20 21  0  0  1  0            999 V2000
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0207537

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)[C@@H](O)CN=C(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)/t15-/m0/s1

> <INCHI_KEY>
NICURWGAEFHESQ-HNNXBMFYSA-N

> <FORMULA>
C16H17NO3

> <MOLECULAR_WEIGHT>
271.316

> <EXACT_MASS>
271.120843411

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.838042650869397

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(2R)-2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid

> <JCHEM_LOGP>
2.803633212666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.129287876544165

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.209993598447818

> <JCHEM_PKA_STRONGEST_BASIC>
3.9827411103604176

> <JCHEM_POLAR_SURFACE_AREA>
62.05

> <JCHEM_REFRACTIVITY>
77.59310000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2R)-2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -2.667 -13.860   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    6   20                                                       
CONECT   20   19    3                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₇NO₃

Average Mass

271.3160 Da

Monoisotopic Mass

271.12084 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)[C@@H](O)CN=C(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)/t15-/m0/s1

InChI Key

NICURWGAEFHESQ-HNNXBMFYSA-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
Clausena brevistyla	LOTUS Database	35616633
Feroniella lucida	LOTUS Database	35616633
Zanthoxylum fagara	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
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	2.8	ChemAxon
pKa (Strongest Acidic)	8.21	ChemAxon
pKa (Strongest Basic)	3.98	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.05 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.59 m³·mol⁻¹	ChemAxon
Polarizability	29.84 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8260091

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10084553

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang Z, Wu X, Li Z, Huang Z, Chen F: Ketoreductase catalyzed stereoselective bioreduction of alpha-nitro ketones. Org Biomol Chem. 2019 Apr 3;17(14):3575-3580. doi: 10.1039/c9ob00051h. [PubMed:30900703 ]
LOTUS database [Link]

Showing NP-Card for n-[(2r)-2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid (NP0207537)

MOL for NP0207537 (n-[(2r)-2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)

3D MOL for NP0207537 (n-[(2r)-2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)

3D SDF for NP0207537 (n-[(2r)-2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)

3D-SDF for NP0207537 (n-[(2r)-2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)

PDB for NP0207537 (n-[(2r)-2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)

3D PDB for NP0207537 (n-[(2r)-2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)

SMILES for NP0207537 (n-[(2r)-2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)

INCHI for NP0207537 (n-[(2r)-2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)

Structure for NP0207537 (n-[(2r)-2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)

3D Structure for NP0207537 (n-[(2r)-2-hydroxy-2-(4-methoxyphenyl)ethyl]benzenecarboximidic acid)