ChemFOnt: Showing chemical card for 4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid (CFc000166734)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 00:00:10 UTC

Chemfont ID

CFc000166734

Molecule Identification

Common Name

4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid

Definition

4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid, also known as 3-dehydroshikimate, belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4,5-Dihydroxy-3-oxocyclohex-1-ene-1-carboxylate	Generator
3-Dehydroshikimate	MeSH
3-Dehydroshikimic acid	MeSH

Chemical Formula

C₇H₈O₅

Average Molecular Weight

172.136

Monoisotopic Molecular Weight

172.037173358

IUPAC Name

4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid

Traditional Name

4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC1CC(=CC(=O)C1O)C(O)=O

InChI Identifier

InChI=1S/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)

InChI Key

SLWWJZMPHJJOPH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	137 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1	ChemAxon
logS	-0.1	ALOGPS
pKa (Strongest Acidic)	3.21	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	38.19 m³·mol⁻¹	ChemAxon
Polarizability	14.93 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0186467

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid (CFc000166734)

MOL for CFc000166734 (4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid)

3D MOL for CFc000166734 (4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid)

3D SDF for CFc000166734 (4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid)

3D-SDF for CFc000166734 (4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid)

PDB for CFc000166734 (4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid)

3D PDB for CFc000166734 (4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid)

SMILES for CFc000166734 (4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid)

INCHI for CFc000166734 (4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid)

Structure for CFc000166734 (4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid)

3D Structure for CFc000166734 (4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid)