Showing Compound Card for 5α-Stigmasta-7,24(28)-dien-3β-ol (CDB000287)

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Record Information
Version1.0
Created at2020-03-19 00:29:00 UTC
Updated at2020-12-07 19:07:19 UTC
CannabisDB IDCDB000287
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name5α-Stigmasta-7,24(28)-dien-3β-ol
Description5α-Stigmasta-7,24(28)-dien-3β-ol is a steroid derivative characterized by a hydroxyl group in position C-3 of the steroid skeleton, and unsaturated bonds in position 7-8 the B ring, and position 24-25 in the alkyl substituent. It belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol-like molecules with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24 and a trans double bond in position C22. 5α-Stigmasta-7,24(28)-dien-3β-ol is a neutral, hydrophobic molecule that is insoluble in water. 5α-Stigmasta-7,24(28)-dien-3β-ol is a naturally occurring phytosterol found in plants. Phytosterols have a cholesterol-like structure consisting of four fused rings as a core structure and an acyclic side chain. Phytosterols differ only in carbon side chains and/or the presence or absence of a double bond. They play a similar role to cholesterol in stabilizing membrane lipids in plants. Phytosterols derive from the same biosynthetic precursor as the triterpenoids (2,3-oxidosqualene) and their biosynthesis also proceeds via the mevalonic acid pathway (MVA), mainly in the cytosol. In humans the intake of naturally occurring phytosterols ranges between ~200–300 mg/day depending on eating habits (PMID: 28702423 ). Phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines) and can reduce cholesterol in human subjects by up to 15% (PMID: 28702423 ). They may also have a role in cancer prevention and treatment (PMID: 26086253 ). Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. 5α-Stigmasta-7,24(28)-dien-3β-ol is one of the phytosterols found in cannabis plants and oils (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
7-DehydroavenasterolKEGG
Δ7-AvenasterolGenerator
(24Z)-24-Ethyl-5alpha-cholesta-7,24(28)-dien-3beta-olHMDB
(24Z)-5alpha-Stigmasta-7,24(28)-dien-3beta-olHMDB
(Z)-5alpha-Stigmasta-7,24(28)-dien-3beta-olHMDB
24Z-EthylidenelathosterolHMDB
3beta-Hydroxy-5alpha-stigmasta-7,24(28)Z-dieneHMDB
5alpha-Stigmasta-7,24(28)-dien-3-olHMDB
5alpha-Stigmasta-7,24(28)-dien-3beta-olHMDB
5alpha-Stigmasta-7,Z-24(28)-diene-3.beta-olHMDB
AvenasterolHMDB
Z-24-Ethylidene-5alpha-cholest-7-en-3beta-olHMDB
(24Z)-24-Ethyl-5α-cholesta-7,24(28)-dien-3β-olHMDB
(24Z)-5α-Stigmasta-7,24(28)-dien-3β-olHMDB
(3beta,5alpha,24Z)-Stigmasta-7,24(28)-dien-3-olHMDB
(3β,5α,24Z)-Stigmasta-7,24(28)-dien-3-olHMDB
(Z)-5α-Stigmasta-7,24(28)-dien-3β-olHMDB
3β-Hydroxy-5α-stigmasta-7,24(28)Z-dieneHMDB
5alpha-Stigmasta-7,Z-24(28)-diene-3beta-olHMDB
5α-Stigmasta-7,24(28)-dien-3-olHMDB
5α-Stigmasta-7,Z-24(28)-diene-3β-olHMDB
Z-24-Ethylidene-5α-cholest-7-en-3β-olHMDB
delta7-AvenasterolHMDB
Chemical FormulaC29H48O
Average Molecular Weight412.7
Monoisotopic Molecular Weight412.3705
IUPAC Name(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R,5Z)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
Traditional Name(1R,2S,5S,7S,11R,14R,15R)-14-[(2R,5Z)-5-isopropylhept-5-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
CAS Registry Number23290-26-8
SMILES
C\C=C(\CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C
InChI Identifier
InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,11,19-20,22-23,25-27,30H,8-10,12-18H2,1-6H3/b21-7-/t20-,22+,23+,25-,26+,27+,28+,29-/m1/s1
InChI KeyMCWVPSBQQXUCTB-OQTIOYDCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassStigmastanes and derivatives
Direct ParentStigmastanes and derivatives
Alternative Parents
Substituents
  • Triterpenoid
  • Stigmastane-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • Delta-7-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.62ALOGPS
logP7.44ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)18.36ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity130.62 m³·mol⁻¹ChemAxon
Polarizability53.66 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5α-Stigmasta-7,24(28)-dien-3β-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f7k-1019000000-bccf5d01490277f0f41cSpectrum
Predicted GC-MS5α-Stigmasta-7,24(28)-dien-3β-ol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06di-2104900000-4f71a97ae7d9183e13f1Spectrum
Predicted GC-MS5α-Stigmasta-7,24(28)-dien-3β-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-1019500000-d9db27d1f0676bf070122017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-4149100000-10c29ad26226f06b51252017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-6197000000-0dad9f7452e27e74d08d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-322cae85ce921a9ef9e22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0005900000-7f1c49cc0c1fb7a57fb42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-2019000000-1b7f3a8af79353d7fab52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-363450e12a0ea926276e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-cc7acf42f15043b109102021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1002900000-210aa86d26d8154c16912021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-f7a69cb97e748b0859232021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0hgc-6249000000-91042d4ec3cdcf8772582021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0537-9310000000-7475a41fd48ab4cbf80d2021-09-23View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Lathosterol oxidaseSC5DL11q23.3O75845 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Lathosterol oxidaseSC5DL11q23.3O75845 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0006851
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030685
KNApSAcK IDC00007322
Chemspider ID24850097
KEGG Compound IDC15782
BioCyc IDCPD-4125
BiGG IDNot Available
Wikipedia LinkAvenasterol
METLIN IDNot Available
PubChem Compound12795736
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Jesch ED, Carr TP: Food Ingredients That Inhibit Cholesterol Absorption. Prev Nutr Food Sci. 2017 Jun;22(2):67-80. doi: 10.3746/pnf.2017.22.2.67. Epub 2017 Jun 30. [PubMed:28702423 ]
  3. Ramprasath VR, Awad AB: Role of Phytosterols in Cancer Prevention and Treatment. J AOAC Int. 2015 May-Jun;98(3):735-738. doi: 10.5740/jaoacint.SGERamprasath. [PubMed:26086253 ]

Enzymes

Enzyme Details
1. Lathosterol oxidase
General function:
Involved in iron ion binding
Specific function:
Catalyzes a dehydrogenation to introduce C5-6 double bond into lathosterol.
Gene Name:
SC5DL
Uniprot ID:
O75845
Molecular weight:
35300.55