NP-MRD: Showing NP-Card for 5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 3-hydroxybenzoate (NP0219329)

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Record Information

Version

1.0

Created at

2022-09-05 20:17:22 UTC

Updated at

2022-09-05 20:17:22 UTC

NP-MRD ID

NP0219329

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

5,6-Dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 3-hydroxybenzoate belongs to the class of organic compounds known as m-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is meta-substituted with a hydroxy group. 5,6-Dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 3-hydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004181501352D          

 21 22  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 O   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
    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
    2.1434   -3.7125    0.0000 C   0  0  0  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  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
    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 O   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 O   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  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
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 O   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
    0.7145   -2.8875    0.0000 C   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  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  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  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  1  0  0  0  0
 17 19  2  0  0  0  0
 13 19  1  0  0  0  0
  9 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0219329

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1=CC(O)C(O)C(OC(=O)C2=CC=CC(O)=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O7/c15-6-8-5-10(17)12(19)13(11(8)18)21-14(20)7-2-1-3-9(16)4-7/h1-5,10,12-13,15-17,19H,6H2

> <INCHI_KEY>
SNBAWTHXVVSPPU-UHFFFAOYSA-N

> <FORMULA>
C14H14O7

> <MOLECULAR_WEIGHT>
294.259

> <EXACT_MASS>
294.073952791

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.631946888095577

> <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 3-hydroxybenzoate

> <ALOGPS_LOGP>
-0.01

> <JCHEM_LOGP>
-0.07243406066666641

> <ALOGPS_LOGS>
-1.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.806391095021437

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.126297357971756

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8220782465047893

> <JCHEM_POLAR_SURFACE_AREA>
124.29000000000002

> <JCHEM_REFRACTIVITY>
71.33659999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.25e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+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  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   13                                                       
CONECT   20    9    3   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
5,6-Dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 3-hydroxybenzoic acid	Generator

Chemical Formula

C₁₄H₁₄O₇

Average Mass

294.2590 Da

Monoisotopic Mass

294.07395 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OCC1=CC(O)C(O)C(OC(=O)C2=CC=CC(O)=C2)C1=O

InChI Identifier

InChI=1S/C14H14O7/c15-6-8-5-10(17)12(19)13(11(8)18)21-14(20)7-2-1-3-9(16)4-7/h1-5,10,12-13,15-17,19H,6H2

InChI Key

SNBAWTHXVVSPPU-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is meta-substituted with a hydroxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

m-Hydroxybenzoic acid esters

Alternative Parents

Substituents

M-hydroxybenzoic acid ester
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
Phenol
Cyclohexenone
1-hydroxy-2-unsubstituted benzenoid
Cyclitol or derivatives
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
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	-0.01	ALOGPS
logP	-0.072	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	9.13	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	71.34 m³·mol⁻¹	ChemAxon
Polarizability	27.63 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

LOTUS database [Link]

Showing NP-Card for 5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 3-hydroxybenzoate (NP0219329)

MOL for NP0219329 (5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 3-hydroxybenzoate)

3D MOL for NP0219329 (5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 3-hydroxybenzoate)

3D SDF for NP0219329 (5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 3-hydroxybenzoate)

3D-SDF for NP0219329 (5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 3-hydroxybenzoate)

PDB for NP0219329 (5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 3-hydroxybenzoate)

3D PDB for NP0219329 (5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 3-hydroxybenzoate)

SMILES for NP0219329 (5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 3-hydroxybenzoate)

INCHI for NP0219329 (5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 3-hydroxybenzoate)

Structure for NP0219329 (5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 3-hydroxybenzoate)

3D Structure for NP0219329 (5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 3-hydroxybenzoate)