NP-MRD: Showing NP-Card for 4R,5R,6S-Trihydroxy-2-hydroxymethyl-2-cyclohexen-1-one 6-(2-hydroxy-6-methylbenzoate) (NP0335918)

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Record Information

Version

2.0

Created at

2024-09-11 03:51:36 UTC

Updated at

2024-09-11 03:51:36 UTC

NP-MRD ID

NP0335918

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4R,5R,6S-Trihydroxy-2-hydroxymethyl-2-cyclohexen-1-one 6-(2-hydroxy-6-methylbenzoate)

Description

4R,5R,6S-Trihydroxy-2-hydroxymethyl-2-cyclohexen-1-one 6-(2-hydroxy-6-methylbenzoate) belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group. Based on a literature review very few articles have been published on 4R,5R,6S-Trihydroxy-2-hydroxymethyl-2-cyclohexen-1-one 6-(2-hydroxy-6-methylbenzoate).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262306232D          

 22 23  0  0  0  0            999 V2000
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   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
    2.8579    2.4750    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
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   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
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 O   0  0  0  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
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  7  1  1  0  0  0  0
  7  3  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 13 10  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 11  1  0  0  0  0
 16  6  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 12  2  0  0  0  0
 20 13  1  0  0  0  0
 21 15  2  0  0  0  0
 22 14  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335918

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C(=O)OC2C(O)C(O)C=C(CO)C2=O)C(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1/C15H16O7/c1-7-3-2-4-9(17)11(7)15(21)22-14-12(19)8(6-16)5-10(18)13(14)20/h2-5,10,13-14,16-18,20H,6H2,1H3

> <INCHI_KEY>
ZJIDZZXKQOJXMR-UHFFFAOYNA-N

> <FORMULA>
C15H16O7

> <MOLECULAR_WEIGHT>
308.286

> <EXACT_MASS>
308.089602855

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.971531900415336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 2-hydroxy-6-methylbenzoate

> <JCHEM_LOGP>
1.0909873286666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.86807923596136

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.84587542617427

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8220782482571414

> <JCHEM_POLAR_SURFACE_AREA>
124.29

> <JCHEM_REFRACTIVITY>
76.3778

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 2-hydroxy-6-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000  10.780   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    7                                                       
CONECT    4    2    9                                                       
CONECT    5    8   10                                                       
CONECT    6    8   16                                                       
CONECT    7    1    3   11                                                  
CONECT    8    5    6   12                                                  
CONECT    9    4   11   17                                                  
CONECT   10    5   13   18                                                  
CONECT   11    7    9   15                                                  
CONECT   12    8   14   19                                                  
CONECT   13   10   14   20                                                  
CONECT   14   12   13   22                                                  
CONECT   15   11   21   22                                                  
CONECT   16    6                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   15                                                            
CONECT   22   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
4R,5R,6S-Trihydroxy-2-hydroxymethyl-2-cyclohexen-1-one 6-(2-hydroxy-6-methylbenzoic acid)	Generator

Chemical Formula

C₁₅H₁₆O₇

Average Mass

308.2860 Da

Monoisotopic Mass

308.08960 Da

IUPAC Name

5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 2-hydroxy-6-methylbenzoate

Traditional Name

5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 2-hydroxy-6-methylbenzoate

CAS Registry Number

Not Available

SMILES

CC1=C(C(=O)OC2C(O)C(O)C=C(CO)C2=O)C(O)=CC=C1

InChI Identifier

InChI=1/C15H16O7/c1-7-3-2-4-9(17)11(7)15(21)22-14-12(19)8(6-16)5-10(18)13(14)20/h2-5,10,13-14,16-18,20H,6H2,1H3

InChI Key

ZJIDZZXKQOJXMR-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

o-Hydroxybenzoic acid esters

Alternative Parents

Substituents

O-hydroxybenzoic acid ester
Salicylic acid or derivatives
Benzoyl
M-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Phenol
Toluene
Cyclitol or derivatives
Vinylogous acid
Ketone
Cyclic ketone
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
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	1.09	ChemAxon
pKa (Strongest Acidic)	9.85	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.38 m³·mol⁻¹	ChemAxon
Polarizability	29.97 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4R,5R,6S-Trihydroxy-2-hydroxymethyl-2-cyclohexen-1-one 6-(2-hydroxy-6-methylbenzoate) (NP0335918)

MOL for NP0335918 (4R,5R,6S-Trihydroxy-2-hydroxymethyl-2-cyclohexen-1-one 6-(2-hydroxy-6-methylbenzoate))

3D MOL for NP0335918 (4R,5R,6S-Trihydroxy-2-hydroxymethyl-2-cyclohexen-1-one 6-(2-hydroxy-6-methylbenzoate))

3D SDF for NP0335918 (4R,5R,6S-Trihydroxy-2-hydroxymethyl-2-cyclohexen-1-one 6-(2-hydroxy-6-methylbenzoate))

3D-SDF for NP0335918 (4R,5R,6S-Trihydroxy-2-hydroxymethyl-2-cyclohexen-1-one 6-(2-hydroxy-6-methylbenzoate))

PDB for NP0335918 (4R,5R,6S-Trihydroxy-2-hydroxymethyl-2-cyclohexen-1-one 6-(2-hydroxy-6-methylbenzoate))

3D PDB for NP0335918 (4R,5R,6S-Trihydroxy-2-hydroxymethyl-2-cyclohexen-1-one 6-(2-hydroxy-6-methylbenzoate))

SMILES for NP0335918 (4R,5R,6S-Trihydroxy-2-hydroxymethyl-2-cyclohexen-1-one 6-(2-hydroxy-6-methylbenzoate))

INCHI for NP0335918 (4R,5R,6S-Trihydroxy-2-hydroxymethyl-2-cyclohexen-1-one 6-(2-hydroxy-6-methylbenzoate))

Structure for NP0335918 (4R,5R,6S-Trihydroxy-2-hydroxymethyl-2-cyclohexen-1-one 6-(2-hydroxy-6-methylbenzoate))

3D Structure for NP0335918 (4R,5R,6S-Trihydroxy-2-hydroxymethyl-2-cyclohexen-1-one 6-(2-hydroxy-6-methylbenzoate))