Showing Compound Card for Dattelic acid (CDB005192)

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Record Information
Version1.0
Created at2020-04-17 19:18:34 UTC
Updated at2020-11-18 16:39:29 UTC
CannabisDB IDCDB005192
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDattelic acid
DescriptionDattelic acid, also known as dattelate or dactylifric acid, belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. A carboxylic ester obtained by formal condensation of the carboxy group of (E)-caffeic acid with the 5-hydroxy group of shikimic acid. Dattelic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Dattelic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5-Caffeoylshikimic acidChEBI
5-CaffeoylshikimateGenerator
DattelateGenerator
Dactylifric acidHMDB
5-O-CaffeoylshikimateHMDB
5-O-Caffeoylshikimic acidHMDB
CaffeoylshikimateHMDB
Caffeoylshikimic acidHMDB
trans-5-O-Caffeoylshikimic acidHMDB
trans-Caffeic acid 5-O-shikimateHMDB
5-[(e)-Caffeoyl]shikimateHMDB
Dattelic acidHMDB
Chemical FormulaC16H16O8
Average Molecular Weight336.3
Monoisotopic Molecular Weight336.0845
IUPAC Name(3R,4R,5R)-5-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
Traditional Name5-O-caffeoylshikimic acid
CAS Registry Number73263-62-4
SMILES
O[C@@H]1C=C(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@@H]1O)C(O)=O
InChI Identifier
InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-6,12-13,15,17-19,21H,7H2,(H,22,23)/b4-2+/t12-,13-,15-/m1/s1
InChI KeyQMPHZIPNNJOWQI-GDDAOPKQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Cyclitol or derivatives
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • 1,2-diol
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.17ALOGPS
logP0.79ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.94ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.49 m³·mol⁻¹ChemAxon
Polarizability32.33 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDattelic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-03dr-0900000000-027d1582ffcfcbcc8a662020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-03di-0900000000-7d436c53d76aac0087352020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-0359000000-a6e04662b2dd608e99a32021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-0921000000-d01231ac2163cb94472a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1910000000-84945d7f7dc8798c6fa22021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03y0-0907000000-95d3be88a395a4fa7c312021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-0933000000-09eaf74af70551c0fd062021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-0900000000-6fa17ca3359a11a2eb392021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0033999
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012233
KNApSAcK IDC00002720
Chemspider ID4445076
KEGG Compound IDC10434
BioCyc IDCAFFEOYLSHIKIMATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281762
PDB IDNot Available
ChEBI ID2106
References
General ReferencesNot Available