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Record Information
Version2.0
Created at2022-09-06 07:44:49 UTC
Updated at2022-09-06 07:44:49 UTC
NP-MRD IDNP0228193
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-[(1r,2r,5r)-2-[(1as,4as,7s,8ar)-7-hydroxy-4a-methyl-4-oxo-1ah,5h,6h,7h,8h-naphtho[1,8a-b]oxiren-3-yl]-1-methyl-5-[(2r)-6-methylheptan-2-yl]cyclopentyl]acetaldehyde
Description3Beta-hydroxy-5alpha,6alpha-epoxy-9-oxo-9,10-seco-5-cholest-7-en-11-al belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, 3beta-hydroxy-5alpha,6alpha-epoxy-9-oxo-9,10-seco-5-cholest-7-en-11-al is considered to be a sterol. 2-[(1r,2r,5r)-2-[(1as,4as,7s,8ar)-7-hydroxy-4a-methyl-4-oxo-1ah,5h,6h,7h,8h-naphtho[1,8a-b]oxiren-3-yl]-1-methyl-5-[(2r)-6-methylheptan-2-yl]cyclopentyl]acetaldehyde is found in Spongia agaricina and Spongia matamata. Based on a literature review very few articles have been published on 3beta-hydroxy-5alpha,6alpha-epoxy-9-oxo-9,10-seco-5-cholest-7-en-11-al.
Structure
Thumb
Synonyms
ValueSource
3b-Hydroxy-5a,6a-epoxy-9-oxo-9,10-seco-5-cholest-7-en-11-alGenerator
3Β-hydroxy-5α,6α-epoxy-9-oxo-9,10-seco-5-cholest-7-en-11-alGenerator
Chemical FormulaC27H42O4
Average Mass430.6290 Da
Monoisotopic Mass430.30831 Da
IUPAC Name2-[(1R,2R,5R)-2-[(1bS,4S,5aR,5bS)-4-hydroxy-1b-methyl--oxo-H,1bH,2H,3H,4H,5H,5bH-naphtho[1,8a-b]oxiren--yl]-1-methyl-5-[(2R)-6-methylheptan-2-yl]cyclopentyl]acetaldehyde
Traditional Name2-[(1R,2R,5R)-2-[(1bS,4S,5aR,5bS)-4-hydroxy-1b-methyl--oxo-2H,3H,4H,5H,5bH-naphtho[1,8a-b]oxiren--yl]-1-methyl-5-[(2R)-6-methylheptan-2-yl]cyclopentyl]acetaldehyde
CAS Registry NumberNot Available
SMILES
CC(C)CCC[C@@H](C)[C@H]1CC[C@@H](C2=C[C@@H]3O[C@@]33C[C@@H](O)CC[C@]3(C)C2=O)[C@]1(C)CC=O
InChI Identifier
InChI=1S/C27H42O4/c1-17(2)7-6-8-18(3)21-9-10-22(25(21,4)13-14-28)20-15-23-27(31-23)16-19(29)11-12-26(27,5)24(20)30/h14-15,17-19,21-23,29H,6-13,16H2,1-5H3/t18-,19+,21-,22+,23+,25-,26-,27+/m1/s1
InChI KeyHWTUUAJZGNFIHU-AUZHTAODSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Spongia agaricinaLOTUS Database
Spongia matamataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Cyclopentane sesquiterpenoid
  • Cyclohexenone
  • Alpha-hydrogen aldehyde
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Aldehyde
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • 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
logP5.11ChemAxon
pKa (Strongest Acidic)15.16ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.9 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity123.14 m³·mol⁻¹ChemAxon
Polarizability51.26 ųChemAxon
Number of Rings4ChemAxon
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 ID8725988
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10550597
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]