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Showing Compound Diosgenin (FDB012734)

Record Information
Version1.0
Creation date2010-04-08 22:10:20 UTC
Update date2019-11-26 03:07:29 UTC
Primary IDFDB012734
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDiosgenin
DescriptionDiosgenin is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Diosgenin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Diosgenin can be found in a number of food items such as carrot, wild carrot, yam, and bitter gourd, which makes diosgenin a potential biomarker for the consumption of these food products. Diosgenin, a phytosteroid sapogenin, is the product of hydrolysis by acids, strong bases, or enzymes of saponins, extracted from the tubers of Dioscorea wild yam, such as the Kokoro. The sugar-free (aglycone) product of such hydrolysis, diosgenin is used for the commercial synthesis of cortisone, pregnenolone, progesterone, and other steroid products .
CAS Number512-04-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(20R,25R)-Spirost-5-en-3beta-olChEBI
(25R)-Spirost-5-en-3beta-olChEBI
NitogeninChEBI
(3beta,25R)-Spirost-5-en-3-olKegg
(20R,25R)-Spirost-5-en-3b-olGenerator
(20R,25R)-Spirost-5-en-3β-olGenerator
(25R)-Spirost-5-en-3b-olGenerator
(25R)-Spirost-5-en-3β-olGenerator
(3b,25R)-Spirost-5-en-3-olGenerator
(3Β,25R)-spirost-5-en-3-olGenerator
(25R)-Spirost-5-en-3β-olbiospider
«delta»biospider
22α-Spirost-5-en-3β-olbiospider
25d-Spirost-5-en-3b-olbiospider
5,20a,22a,25D-spirosten-3β-olbiospider
5,20alpha,22alpha,25D-Spirosten-3 beta-olbiospider
Dioscorea sapogenindb_source
Diosgenindb_source
Spirost-5-en-3-olbiospider
Spirost-5-en-3-ol deriv.biospider
Spirost-5-en-3-ol, (3β,25R)-biospider
Spirost-5-en-3-ol, (3b,25R)-biospider
Spirost-5-en-3α-Spirost-5-en-3β-olbiospider
Spirost-5-en-3β-ol, (25R)-biospider
Spirost-5-en-3b-ol, (25R)-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.00055 g/LALOGPS
logP4.15ALOGPS
logP4.93ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity120.27 m³·mol⁻¹ChemAxon
Polarizability50.68 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC27H42O3
IUPAC name(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-en-16'-ol
InChI IdentifierInChI=1S/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28H,6-15H2,1-4H3
InChI KeyWQLVFSAGQJTQCK-UHFFFAOYSA-N
Isomeric SMILESCC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CO1
Average Molecular Weight414.6206
Monoisotopic Molecular Weight414.31339521
Classification
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Spirostane skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • Steroid
  • Delta-5-steroid
  • Ketal
  • Oxane
  • Tetrahydrofuran
  • Cyclic alcohol
  • Secondary alcohol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 78.21%; H 10.21%; O 11.58%DFC
Melting PointMp 204-207°DFC
Boiling PointNot Available
Experimental Water Solubility2e-05 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -129 (c, 1.4 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08898
Pubchem Compound ID234096
Pubchem Substance IDNot Available
ChEBI ID495816
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHBL90-H:HKK91-O
EAFUS IDNot Available
Dr. Duke IDDIOSGENIN
BIGG IDNot Available
KNApSAcK IDC00003576
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDiosgenin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti-fatigue52217 An agent that reduces physical and mental exhaustion, enhancing endurance and vitality. It plays a biological role in regulating energy metabolism and mitigating oxidative stress. Therapeutically, anti-fatigue agents are used to manage chronic fatigue syndrome, improve athletic performance, and alleviate symptoms of anemia and other debilitating conditions.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti-stress52217 An agent that reduces stress symptoms, commonly used in managing anxiety disorders, promoting relaxation, and mitigating the biological effects of stress on the body, such as hypertension and immune suppression, with therapeutic applications in mental health and key medical uses in cardiology and neurology.DUKE
EstrogenicAn agent that mimics the effects of estrogen, regulating female reproductive processes and development. Therapeutically, estrogenic agents are used in hormone replacement therapy, contraception, and treating menopausal symptoms, as well as certain cases of osteoporosis and infertility.DUKE
Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.DUKE
HypocholesterolemicAn agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.DUKE
MastogenicA natural process stimulating breast tissue growth and development, playing a biological role in lactation and puberty. Therapeutically, mastogenic agents are used to enhance breast size and density, with medical applications in hormone replacement therapy and breast reconstruction.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.CHEBI
Anti neoplastic35610 An agent that inhibits or suppresses the growth and proliferation of cancer cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce apoptosis, prevent tumor progression, and enhance patient survival. Key medical uses include chemotherapy, radiation therapy, and targeted therapy for various types of cancer, such as leukemia, breast, lung, and colon cancer.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.