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Record Information
Version1.0
Created at2022-09-12 08:20:59 UTC
Updated at2022-09-12 08:20:59 UTC
NP-MRD IDNP0326619
Secondary Accession NumbersNone
Natural Product Identification
Common Name{3,4,5-trihydroxy-6-[(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)methoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
Description{3,4,5-Trihydroxy-6-[(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)methoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate 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. {3,4,5-trihydroxy-6-[(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)methoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate is found in Gardenia jasminoides. {3,4,5-Trihydroxy-6-[(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)methoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
{3,4,5-trihydroxy-6-[(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)methoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acidGenerator
Chemical FormulaC27H36O11
Average Mass536.5740 Da
Monoisotopic Mass536.22576 Da
IUPAC Name{3,4,5-trihydroxy-6-[(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)methoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
Traditional Name{3,4,5-trihydroxy-6-[(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)methoxy]oxan-2-yl}methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
CAS Registry NumberNot Available
SMILES
COC1=CC(C=CC(=O)OCC2OC(OCC3C(C)=CC(=O)CC3(C)C)C(O)C(O)C2O)=CC(OC)=C1O
InChI Identifier
InChI=1S/C27H36O11/c1-14-8-16(28)11-27(2,3)17(14)12-37-26-25(33)24(32)23(31)20(38-26)13-36-21(29)7-6-15-9-18(34-4)22(30)19(10-15)35-5/h6-10,17,20,23-26,30-33H,11-13H2,1-5H3
InChI KeySGHMUAWQXUYUAJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Gardenia jasminoidesLOTUS Database
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
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Methoxyphenol
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • Cyclohexenone
  • Alkyl aryl ether
  • Fatty acid ester
  • Phenol
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Monocyclic benzene moiety
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid ester
  • Ketone
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Polyol
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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
logP1.65ALOGPS
logP1.89ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)9.29ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area161.21 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity135.94 m³·mol⁻¹ChemAxon
Polarizability55.75 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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 LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]