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Record Information
Version2.0
Created at2022-03-17 20:09:06 UTC
Updated at2022-03-17 20:09:06 UTC
NP-MRD IDNP0046633
Secondary Accession NumbersNone
Natural Product Identification
Common Name24-Methylene-24-dihydrolanosterol
Description24-Methylene-24-dihydrolanosterol, also known as (3beta)-24-methylidenelanost-8-en-3-ol or obtusifoldienol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 24-Methylene-24-dihydrolanosterol is found in Agaricus campestris , Alternaria gaisen, Alternaria kikuchiana, Eremogone kansuensis, Botrytis cinerea, Candida albicans, Candida utilis, Euphorbia acrurensis, Euphorbia antiquorum , Euphorbia echinus, Euphorbia falcata L. , Euphorbia kansui, Euphorbia lathyris , Euphorbia obtusifolia, Euphorbia regis-tubae, Euphorbia resinfera, Euphorbia tinctoria , Euphorbia tirucalli , Eutypa lata, Leptoshaeria maculans, Leptosphaeria maculans, Monilinia fructigena, Neolitsea sericea, Neurospora crassa, Panax ginseng, Phycomyces blakesleeanus, Antrodia camphorata and Venturia inaequalis. 24-Methylene-24-dihydrolanosterol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
(3beta)-24-Methylidenelanost-8-en-3-olChEBI
24-Methylene-24,25-dihydrolanosterolChEBI
24-Methylenelanost-8-en-3beta-olChEBI
ObtusifoldienolChEBI
(3b)-24-Methylidenelanost-8-en-3-olGenerator
(3Β)-24-methylidenelanost-8-en-3-olGenerator
24-Methylenelanost-8-en-3b-olGenerator
24-Methylenelanost-8-en-3β-olGenerator
Ebericol, (14)C-labeledMeSH
EuphorbolMeSH
24-Methylenelanost-8-en-3 beta-olMeSH
EbericolMeSH
Chemical FormulaC31H52O
Average Mass440.7440 Da
Monoisotopic Mass440.40182 Da
IUPAC Name(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
Traditional Name(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
CAS Registry NumberNot Available
SMILES
[H][C@@]12CCC3=C(CC[C@]4(C)[C@H](CC[C@@]34C)[C@H](C)CCC(=C)C(C)C)[C@@]1(C)CC[C@H](O)C2(C)C
InChI Identifier
InChI=1S/C31H52O/c1-20(2)21(3)10-11-22(4)23-14-18-31(9)25-12-13-26-28(5,6)27(32)16-17-29(26,7)24(25)15-19-30(23,31)8/h20,22-23,26-27,32H,3,10-19H2,1-2,4-9H3/t22-,23-,26+,27+,29-,30-,31+/m1/s1
InChI KeyXJLZCPIILZRCPS-ANMPWZFDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agaricus campestrisFungi
Alternaria gaisenLOTUS Database
Alternaria kikuchianaFungi
Arenaria kansuensisLOTUS Database
Botrytis cinereaLOTUS Database
Candida albicansFungi
Candida utilisFungi
Cucumis sativus L.FooDB
Euphorbia acrurensisPlant
Euphorbia antiquorumPlant
Euphorbia echinusPlant
Euphorbia falcata L.Plant
Euphorbia kansuiLOTUS Database
Euphorbia lathyrisPlant
Euphorbia obtusifoliaPlant
Euphorbia regis-tubaePlant
Euphorbia resinferaPlant
Euphorbia tinctoriaPlant
Euphorbia tirucalliPlant
Eutypa lataLOTUS Database
Leptoshaeria maculans-
Leptosphaeria maculansLOTUS Database
Monilinia fructigenaLOTUS Database
Neolitsea sericeaPlant
Neurospora crassaFungi
Panax ginsengLOTUS Database
Phycomyces blakesleeanusFungi
Taiwanofungus camphoratusFungi
Venturia inaequalisLOTUS Database
Chemical Taxonomy
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
  • 14-alpha-methylsteroid
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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
logP7.85ALOGPS
logP8.05ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity138.02 m³·mol⁻¹ChemAxon
Polarizability56.69 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005281
KNApSAcK IDC00023805
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9803310
PDB IDNot Available
ChEBI ID70315
Good Scents IDNot Available
References
General References