Showing Compound Card for Lathosterol (CDB005345)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (6)transporters (1) Show 10 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:33:54 UTC
Updated at2020-12-07 19:11:59 UTC
CannabisDB IDCDB005345
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameLathosterol
DescriptionLathosterol, also known as gamma-cholesterol or (7)-cholestenol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, lathosterol is considered to be a sterol lipid molecule. Lathosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Lathosterol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
gamma-CholesterolChEBI
5alpha-Cholest-7-en-3beta-olKegg
g-CholesterolGenerator
Γ-cholesterolGenerator
5a-Cholest-7-en-3b-olGenerator
5Α-cholest-7-en-3β-olGenerator
(3beta)-Cholest-7-en-3-olHMDB
(3beta,5alpha)-Cholest-7-en-3-olHMDB
(3beta,alpha)-Cholest-7-en-3-olHMDB
(7)-CholestenolHMDB
3b-Hydroxy-5-cholesteneHMDB
3beta-Hydroxy-5alpha-cholest-7-eneHMDB
5-a-Cholest-7-en-3-beta-olHMDB
5-alpha-Cholest-7-en-3-beta-olHMDB
7-Cholesten-3-beta-olHMDB
7-CholestenolHMDB
7-CholesterolHMDB
Cholest-7-en-3-olHMDB
Cholest-7-en-3beta-olHMDB
Cholest-7-en-olHMDB
Cholesterol - syntheticHMDB
Cholesterol extra pureHMDB
Cholesterol GRHMDB
Cholesterol pharmaHMDB
Cholesterol,NF gradeHMDB
delta(7)-CholestenolHMDB
DELTA7-Cholesten-3beta-olHMDB
DELTA7-CholestenolHMDB
gamma-CholestenolHMDB
LathosterolChEBI
Chemical FormulaC27H46O
Average Molecular Weight386.65
Monoisotopic Molecular Weight386.3549
IUPAC Name(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-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)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
CAS Registry Number80-99-9
SMILES
[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h10,18-21,23-25,28H,6-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25+,26+,27-/m1/s1
InChI KeyIZVFFXVYBHFIHY-SKCNUYALSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • Cholesterol
  • 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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point122.0 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.4ALOGPS
logP7.11ChemAxon
logS-7ALOGPS
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
Refractivity120.62 m³·mol⁻¹ChemAxon
Polarizability50.52 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-MSLathosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-1019000000-45e8f26aff61be3d325aSpectrum
Predicted GC-MSLathosterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-3004900000-efe936a9ed1a83aa429cSpectrum
Predicted GC-MSLathosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0009000000-88fe25051d65e99ecb322016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05p9-3149000000-d25373f7179ed89b61dc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c00-6359000000-8bff83f3efe22597deab2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-82b1527837d67c6be40a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-e2badd995ee41a69b18f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ldi-1009000000-96f6e67651380e1c959e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-178681247f50782398982021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avu-9233000000-247b9ee1da8d484a4da62021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9710000000-8ebbaf147cf1232af8792021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-c037f2d2f217e99b79ac2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-c037f2d2f217e99b79ac2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0009000000-fbd8e8ecfb898bb732a52021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Lathosterol oxidaseSC5DL11q23.3O75845 details
Methylsterol monooxygenase 1MSMO14q32-q34Q15800 details
Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylatingNSDHLXq28Q15738 details
3-keto-steroid reductaseHSD17B71q23P56937 details
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomeraseEBPXp11.23-p11.22Q15125 details
Delta(24)-sterol reductaseDHCR241p32.3Q15392 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomeraseEBPXp11.23-p11.22Q15125 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Lathosterol oxidaseSC5DL11q23.3O75845 details
Methylsterol monooxygenase 1MSMO14q32-q34Q15800 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomeraseEBPXp11.23-p11.22Q15125 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001170
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022463
KNApSAcK IDC00023744
Chemspider ID59151
KEGG Compound IDC01189
BioCyc IDNot Available
BiGG ID37036
Wikipedia LinkLathosterol
METLIN ID6052
PubChem Compound65728
PDB IDNot Available
ChEBI ID17168
References
General ReferencesNot Available

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
Enzyme Details
2. Methylsterol monooxygenase 1
General function:
Involved in iron ion binding
Specific function:
Not Available
Gene Name:
MSMO1
Uniprot ID:
Q15800
Molecular weight:
19470.325
Enzyme Details
3. Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
Not Available
Gene Name:
NSDHL
Uniprot ID:
Q15738
Molecular weight:
41899.99
Enzyme Details
4. 3-keto-steroid reductase
General function:
Involved in oxidoreductase activity
Specific function:
Responsible for the reduction of the keto group on the C-3 of sterols.
Gene Name:
HSD17B7
Uniprot ID:
P56937
Molecular weight:
38205.77
Enzyme Details
5. 3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase
General function:
Involved in cholestenol delta-isomerase activity
Specific function:
Catalyzes the conversion of Delta(8)-sterols to their corresponding Delta(7)-isomers.
Gene Name:
EBP
Uniprot ID:
Q15125
Molecular weight:
26352.615
Enzyme Details
6. Delta(24)-sterol reductase
General function:
Energy production and conversion
Specific function:
Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:
DHCR24
Uniprot ID:
Q15392
Molecular weight:
60100.805

Transporters

Enzyme Details
1. 3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase
General function:
Involved in cholestenol delta-isomerase activity
Specific function:
Catalyzes the conversion of Delta(8)-sterols to their corresponding Delta(7)-isomers.
Gene Name:
EBP
Uniprot ID:
Q15125
Molecular weight:
26352.615