Np mrd loader

Record Information
Version2.0
Created at2024-09-11 23:05:41 UTC
Updated at2024-09-11 23:05:41 UTC
NP-MRD IDNP0339694
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-dehydroshikimate
Description3-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. 3-dehydroshikimate was first documented in 2024 (PMID: 39222859). Based on a literature review a small amount of articles have been published on 3-dehydroshikimate (PMID: 39153079) (PMID: 38809816) (PMID: 38780531) (PMID: 38521489).
Structure
Thumb
Synonyms
ValueSource
3-Dehydroshikimic acidGenerator
Chemical FormulaC7H7O5
Average Mass171.1290 Da
Monoisotopic Mass171.02990 Da
IUPAC Name4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylate
Traditional Name4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylate
CAS Registry NumberNot Available
SMILES
OC1CC(=CC(=O)C1O)C([O-])=O
InChI Identifier
InChI=1/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)/p-1
InChI KeySLWWJZMPHJJOPH-UHFFFAOYNA-M
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cyclohexenones. These are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclohexenones
Alternative Parents
Substituents
  • Cyclohexenone
  • Secondary alcohol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organic anion
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1ChemAxon
pKa (Strongest Acidic)3.02ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.66 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.03 m³·mol⁻¹ChemAxon
Polarizability14.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Dehydroshikimic acid
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Liu D, Wang L, Ma L, Wang X, Li S, Zhou J: Metabolic network rewiring and temperature-dependent regulation for enhanced 3-dehydroshikimate production in Escherichia coli. Bioresour Technol. 2024 Nov;412:131403. doi: 10.1016/j.biortech.2024.131403. Epub 2024 Aug 31. [PubMed:39222859 ]
  2. Orn OE, Hagman A, Ismail M, Leiva Eriksson N, Hatti-Kaul R: Enhancing metabolic efficiency via novel constitutive promoters to produce protocatechuic acid in Escherichia coli. Appl Microbiol Biotechnol. 2024 Aug 17;108(1):442. doi: 10.1007/s00253-024-13256-6. [PubMed:39153079 ]
  3. Akyuz Turumtay E, Turumtay H, Tian Y, Lin CY, Chai YN, Louie KB, Chen Y, Lipzen A, Harwood T, Satish Kumar K, Bowen BP, Wang Q, Mansfield SD, Blow MJ, Petzold CJ, Northen TR, Mortimer JC, Scheller HV, Eudes A: Expression of dehydroshikimate dehydratase in poplar induces transcriptional and metabolic changes in the phenylpropanoid pathway. J Exp Bot. 2024 Aug 28;75(16):4960-4977. doi: 10.1093/jxb/erae251. [PubMed:38809816 ]
  4. Senanayake M, Lin CY, Mansfield SD, Eudes A, Davison BH, Pingali SV, O'Neill H: Ectopic Production of 3,4-Dihydroxybenzoate in Planta Affects Cellulose Structure and Organization. Biomacromolecules. 2024 Jun 10;25(6):3542-3553. doi: 10.1021/acs.biomac.4c00187. Epub 2024 May 23. [PubMed:38780531 ]
  5. Wu F, Wang S, Zhou D, Gao S, Song G, Liang Y, Wang Q: Metabolic engineering of Escherichia coli for high-level production of the biodegradable polyester monomer 2-pyrone-4,6-dicarboxylic acid. Metab Eng. 2024 May;83:52-60. doi: 10.1016/j.ymben.2024.03.003. Epub 2024 Mar 21. [PubMed:38521489 ]