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Record Information
Version2.0
Created at2022-09-12 14:35:53 UTC
Updated at2022-09-12 14:35:53 UTC
NP-MRD IDNP0329824
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,2s,6s,7s,9r,13s,17s)-15-(hydroxymethyl)-4-methoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-4,14-diene-3,11,16-trione
Description18-Hydroxyquassin belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. (1s,2s,6s,7s,9r,13s,17s)-15-(hydroxymethyl)-4-methoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-4,14-diene-3,11,16-trione is found in Quassia amara. Based on a literature review very few articles have been published on 18-Hydroxyquassin.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC22H28O6
Average Mass388.4600 Da
Monoisotopic Mass388.18859 Da
IUPAC Name(1S,2S,6S,7S,9R,13S,17S)-15-(hydroxymethyl)-4-methoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-4,14-diene-3,11,16-trione
Traditional Name(1S,2S,6S,7S,9R,13S,17S)-15-(hydroxymethyl)-4-methoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-4,14-diene-3,11,16-trione
CAS Registry NumberNot Available
SMILES
COC1=C[C@@H](C)[C@@H]2C[C@H]3OC(=O)C[C@H]4C(C)=C(CO)C(=O)[C@@H]([C@@]34C)[C@@]2(C)C1=O
InChI Identifier
InChI=1S/C22H28O6/c1-10-6-15(27-5)20(26)22(4)13(10)7-16-21(3)14(8-17(24)28-16)11(2)12(9-23)18(25)19(21)22/h6,10,13-14,16,19,23H,7-9H2,1-5H3/t10-,13+,14+,16-,19+,21-,22+/m1/s1
InChI KeyDHIMAWQFCVIDLK-XJTLZAITSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Quassia amaraLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentQuassinoids
Alternative Parents
Substituents
  • Polycyclic triterpenoid
  • Triterpenoid
  • C-20 quassinoid skeleton
  • Quassinoid
  • Naphthopyran
  • Naphthalene
  • Cyclohexenone
  • Delta_valerolactone
  • Delta valerolactone
  • Pyran
  • Oxane
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP1.76ChemAxon
pKa (Strongest Acidic)14.95ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area89.9 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity103.62 m³·mol⁻¹ChemAxon
Polarizability40.99 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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 LinkNot Available
METLIN IDNot Available
PubChem Compound101703196
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]