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Showing Compound (5alpha,6beta,14alpha,20R,22R)-5,6,14,20,27-Pentahydroxy-1-oxowith-24-enolide (FDB011210)

Record Information
Version1.0
Creation date2010-04-08 22:09:31 UTC
Update date2019-11-26 03:04:41 UTC
Primary IDFDB011210
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(5alpha,6beta,14alpha,20R,22R)-5,6,14,20,27-Pentahydroxy-1-oxowith-24-enolide
Description(5alpha,6beta,14alpha,20R,22R)-5,6,14,20,27-Pentahydroxy-1-oxowith-24-enolide belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. Based on a literature review a small amount of articles have been published on (5alpha,6beta,14alpha,20R,22R)-5,6,14,20,27-Pentahydroxy-1-oxowith-24-enolide.
CAS Number222609-97-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.44 g/LALOGPS
logP1.4ALOGPS
logP1.18ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)13.07ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity131.31 m³·mol⁻¹ChemAxon
Polarizability55.14 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC28H42O8
IUPAC name6-(1-hydroxy-1-{7,8,11-trihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}ethyl)-3-(hydroxymethyl)-4-methyl-5,6-dihydro-2H-pyran-2-one
InChI IdentifierInChI=1S/C28H42O8/c1-15-12-22(36-23(32)16(15)14-29)26(4,33)19-8-11-27(34)18-13-21(31)28(35)9-5-6-20(30)25(28,3)17(18)7-10-24(19,27)2/h17-19,21-22,29,31,33-35H,5-14H2,1-4H3
InChI KeyAYSGOPOJGPEGSU-UHFFFAOYSA-N
Isomeric SMILESCC1=C(CO)C(=O)OC(C1)C(C)(O)C1CCC2(O)C3CC(O)C4(O)CCCC(=O)C4(C)C3CCC12C
Average Molecular Weight506.6283
Monoisotopic Molecular Weight506.28796832
Classification
Description Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentWithanolides and derivatives
Alternative Parents
Substituents
  • Withanolide-skeleton
  • 26-hydroxysteroid
  • 20-hydroxysteroid
  • 14-hydroxysteroid
  • 6-hydroxysteroid
  • 5-hydroxysteroid
  • Hydroxysteroid
  • 1-oxosteroid
  • Oxosteroid
  • Dihydropyranone
  • Pyran
  • Cyclic alcohol
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Ketone
  • Oxacycle
  • Polyol
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Primary alcohol
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Route of exposure:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(5alpha,6beta,14alpha,20R,22R)-5,6,14,20,27-Pentahydroxy-1-oxowith-24-enolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002r-1246900000-9b83d706ba13049f34e7Spectrum
Predicted GC-MS(5alpha,6beta,14alpha,20R,22R)-5,6,14,20,27-Pentahydroxy-1-oxowith-24-enolide, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-2243419000-56842deecb780fba4f2dSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0001920000-a97e8a0ae06c93eb90862016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-2124900000-e53bd18dae7d0bd7c6842016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007p-9137500000-29936e31d1747660a44a2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0002970000-35ce10a76bc9045f05512016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zor-0608910000-127a8851953f382b77522016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001r-9302000000-c80b1af715f919ea3d812016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000390000-1f00086190caef706c1c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6u-1203910000-abc9a4684b146453ca012021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9700810000-49785d57e2a489ae95042021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0000970000-8de23dbacd6b265cfb772021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-8905000000-9a55c16b4438fbcaca8a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0095-7924000000-5937c4a4c056d0b539d12021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33198
CRC / DFC (Dictionary of Food Compounds) IDGDY40-I:GDY75-W
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference