NP-MRD: Showing NP-Card for 4-methylaminobenzoyl-L-rhamnopyranoside (NP0332708)

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Record Information

Version

2.0

Created at

2024-03-21 17:34:05 UTC

Updated at

2025-12-21 21:41:03 UTC

NP-MRD ID

NP0332708

Natural Product DOI

https://doi.org/10.57994/1969

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-methylaminobenzoyl-L-rhamnopyranoside

Description

CHEMBL2334067 belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Based on a literature review very few articles have been published on CHEMBL2334067.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03212417342D          

 21 22  0  0  1  0            999 V2000
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  2  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
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   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 C   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
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
 10  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 13 20  1  0  0  0  0
 12 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332708

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNC1=CC=C(C=C1)C(=O)O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H19NO6/c1-7-10(16)11(17)12(18)14(20-7)21-13(19)8-3-5-9(15-2)6-4-8/h3-7,10-12,14-18H,1-2H3/t7-,10-,11+,12+,14-/m0/s1

> <INCHI_KEY>
QTQDEWDRPTZMDX-FNZUUINPSA-N

> <FORMULA>
C14H19NO6

> <MOLECULAR_WEIGHT>
297.307

> <EXACT_MASS>
297.121237336

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
29.80069624506753

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl 4-(methylamino)benzoate

> <JCHEM_LOGP>
0.08244872466666683

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.267075890972063

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.209057788235029

> <JCHEM_PKA_STRONGEST_BASIC>
3.096976712937065

> <JCHEM_POLAR_SURFACE_AREA>
108.25

> <JCHEM_REFRACTIVITY>
74.39550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl 4-(methylamino)benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-MAR-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-MAR-24         0                                  
HETATM    1  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -6.668  -2.310   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   13                                                       
CONECT   21   12                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₉NO₆

Average Mass

297.3070 Da

Monoisotopic Mass

297.12124 Da

IUPAC Name

(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl 4-(methylamino)benzoate

Traditional Name

(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl 4-(methylamino)benzoate

CAS Registry Number

Not Available

SMILES

CNC1=CC=C(C=C1)C(=O)O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C14H19NO6/c1-7-10(16)11(17)12(18)14(20-7)21-13(19)8-3-5-9(15-2)6-4-8/h3-7,10-12,14-18H,1-2H3/t7-,10-,11+,12+,14-/m0/s1

InChI Key

QTQDEWDRPTZMDX-FNZUUINPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Sarani Kankanamge	2024-03-21	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Sarani Kankanamge	2024-03-21	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Sarani Kankanamge	2024-03-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Sarani Kankanamge	2024-03-21	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces virginiae		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Aminobenzoic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Phenylalkylamine
Aniline or substituted anilines
Benzoyl
Secondary aliphatic/aromatic amine
Monocyclic benzene moiety
Benzenoid
Oxane
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Secondary amine
Polyol
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Amine
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	0.082	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	108.25 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.4 m³·mol⁻¹	ChemAxon
Polarizability	29.8 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

29415245

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71524395

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 4-methylaminobenzoyl-L-rhamnopyranoside (NP0332708)

MOL for NP0332708 (4-methylaminobenzoyl-L-rhamnopyranoside )

3D MOL for NP0332708 (4-methylaminobenzoyl-L-rhamnopyranoside )

3D SDF for NP0332708 (4-methylaminobenzoyl-L-rhamnopyranoside )

3D-SDF for NP0332708 (4-methylaminobenzoyl-L-rhamnopyranoside )

PDB for NP0332708 (4-methylaminobenzoyl-L-rhamnopyranoside )

3D PDB for NP0332708 (4-methylaminobenzoyl-L-rhamnopyranoside )

SMILES for NP0332708 (4-methylaminobenzoyl-L-rhamnopyranoside )

INCHI for NP0332708 (4-methylaminobenzoyl-L-rhamnopyranoside )

Structure for NP0332708 (4-methylaminobenzoyl-L-rhamnopyranoside )

3D Structure for NP0332708 (4-methylaminobenzoyl-L-rhamnopyranoside )