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Record Information
Version2.0
Created at2022-09-03 06:21:32 UTC
Updated at2022-09-03 06:21:32 UTC
NP-MRD IDNP0170239
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3s,5as,5br,7ar,8r,9r,11ar,11br,13s,13as)-8-ethyl-13-hydroxy-3,5b,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-9-yl acetate
DescriptionAcetic acid (21S)-13beta,24-dimethyl-12alpha-hydroxy-19-oxo-20-oxa-27,28,29,30-tetranorhopane-17-ene-3alpha-yl ester belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions. (3s,5as,5br,7ar,8r,9r,11ar,11br,13s,13as)-8-ethyl-13-hydroxy-3,5b,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-9-yl acetate is found in Phyllospongia lamellosa. Based on a literature review very few articles have been published on Acetic acid (21S)-13beta,24-dimethyl-12alpha-hydroxy-19-oxo-20-oxa-27,28,29,30-tetranorhopane-17-ene-3alpha-yl ester.
Structure
Thumb
Synonyms
ValueSource
Acetate (21S)-13b,24-dimethyl-12a-hydroxy-19-oxo-20-oxa-27,28,29,30-tetranorhopane-17-ene-3a-yl esterGenerator
Acetate (21S)-13beta,24-dimethyl-12alpha-hydroxy-19-oxo-20-oxa-27,28,29,30-tetranorhopane-17-ene-3alpha-yl esterGenerator
Acetate (21S)-13β,24-dimethyl-12α-hydroxy-19-oxo-20-oxa-27,28,29,30-tetranorhopane-17-ene-3α-yl esterGenerator
Acetic acid (21S)-13b,24-dimethyl-12a-hydroxy-19-oxo-20-oxa-27,28,29,30-tetranorhopane-17-ene-3a-yl esterGenerator
Acetic acid (21S)-13β,24-dimethyl-12α-hydroxy-19-oxo-20-oxa-27,28,29,30-tetranorhopane-17-ene-3α-yl esterGenerator
Chemical FormulaC29H44O5
Average Mass472.6660 Da
Monoisotopic Mass472.31887 Da
IUPAC Name(1R,2S,6S,10S,11S,13R,14R,17R,18R,19R)-18-ethyl-11-hydroxy-1,6,10,14,18-pentamethyl-8-oxo-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5(9)-en-17-yl acetate
Traditional Name(1R,2S,6S,10S,11S,13R,14R,17R,18R,19R)-18-ethyl-11-hydroxy-1,6,10,14,18-pentamethyl-8-oxo-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5(9)-en-17-yl acetate
CAS Registry NumberNot Available
SMILES
CC[C@@]1(C)[C@@H](CC[C@@]2(C)[C@H]1CC[C@@]1(C)[C@@H]3CCC4=C(C(=O)O[C@H]4C)[C@@]3(C)[C@@H](O)C[C@H]21)OC(C)=O
InChI Identifier
InChI=1S/C29H44O5/c1-8-26(4)19-11-13-28(6)20-10-9-18-16(2)33-25(32)24(18)29(20,7)22(31)15-21(28)27(19,5)14-12-23(26)34-17(3)30/h16,19-23,31H,8-15H2,1-7H3/t16-,19-,20-,21+,22-,23+,26+,27-,28-,29+/m0/s1
InChI KeyDMEJTJRZMKFCQV-QTFXJGTNSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Phyllospongia lamellosaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesterterpenoids
Direct ParentScalarane sesterterpenoids
Alternative Parents
Substituents
  • Scalarane sesterterpenoid
  • Steroid lactone
  • 2-hydroxysteroid
  • Hydroxysteroid
  • 7-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • 16-oxasteroid
  • Steroid
  • 2-furanone
  • Dicarboxylic acid or derivatives
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Cyclic alcohol
  • Dihydrofuran
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • 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
logP5.1ALOGPS
logP4.93ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)13.35ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity130.43 m³·mol⁻¹ChemAxon
Polarizability54.62 ųChemAxon
Number of Rings5ChemAxon
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 ID10201793
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21586427
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]