4beta-methylzymosterol-4alpha-carboxylic acid (YMDB00610)

Identification
YMDB IDYMDB00610
Name4beta-methylzymosterol-4alpha-carboxylic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol, also known as 4alpha-carboxy-4beta-methyl-zymosterol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol is considered to be a sterol. Based on a literature review a significant number of articles have been published on 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • (3b,4a,5a)-3-Hydroxy-4-methylcholesta-8,24-diene-4-carboxylate
  • (3b,4a,5a)-3-Hydroxy-4-methylcholesta-8,24-diene-4-carboxylic acid
  • (3beta,4alpha,5alpha)-3-Hydroxy-4-methylcholesta-8,24-diene-4-carboxylate
  • (3beta,4alpha,5alpha)-3-Hydroxy-4-methylcholesta-8,24-diene-4-carboxylic acid
  • (3β,4α,5α)-3-hydroxy-4-methylcholesta-8,24-diene-4-carboxylate
  • (3β,4α,5α)-3-hydroxy-4-methylcholesta-8,24-diene-4-carboxylic acid
  • 4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol
  • 4a-Carboxy-4b-methyl-cholesta-8,24-dien-3b-ol
  • 4a-Carboxy-4b-methyl-zymosterol
  • 4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-ol
  • 4alpha-Carboxy-4beta-methyl-cholesta-8,24-dien-3beta-ol
  • 4alpha-Carboxy-4beta-methyl-zymosterol
  • 4b-Methyl-zymosterol-4a-carboxylate
  • 4b-Methyl-zymosterol-4a-carboxylic acid
  • 4beta-Methyl-zymosterol-4alpha-carboxylate
  • 4α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol
  • 4α-carboxy-4β-methyl-cholesta-8,24-dien-3β-ol
  • 4α-carboxy-4β-methyl-zymosterol
  • 4β-methyl-zymosterol-4α-carboxylate
  • 4β-methyl-zymosterol-4α-carboxylic acid
CAS numberNot Available
WeightAverage: 442.6737
Monoisotopic: 442.344695338
InChI KeyMYWAIWDQTCHPTH-LJAIZBFVSA-N
InChIInChI=1S/C29H46O3/c1-18(2)8-7-9-19(3)21-11-12-22-20-10-13-24-28(5,23(20)14-16-27(21,22)4)17-15-25(30)29(24,6)26(31)32/h8,19,21-22,24-25,30H,7,9-17H2,1-6H3,(H,31,32)/t19-,21-,22+,24-,25+,27-,28-,29+/m1/s1
IUPAC Name(2S,5S,6S,7R,11R,14R,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylic acid
Traditional IUPAC Name(2S,5S,6S,7R,11R,14R,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylic acid
Chemical FormulaC29H46O3
SMILES[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@](C)(C(O)=O)[C@]1([H])CC3)[C@H](C)CCC=C(C)C
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
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • 4-carboxy steroid
  • Steroid acid
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 15-hydroxysteroid
  • Steroid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0022 g/LALOGPS
logP6.64ALOGPS
logP6.6ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.59ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity131.79 m³·mol⁻¹ChemAxon
Polarizability54.42 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
NAD + 4beta-methylzymosterol-4alpha-carboxylic acid → NADH + 3-dehydro-4-methylzymosterol + Carbon dioxide + hydron
oxygen + 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + hydron + NADPH → 4beta-methylzymosterol-4alpha-carboxylic acid + NADP + water
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-1009500000-659d37e4a554032db655JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-3001290000-49cf623a8c01d727af89JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0003900000-f0c6600c4e9f4b0ebe5bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1009500000-0b5ddc78f46f99358d6aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-3139200000-0ffe6baaea219aee2a61JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0004900000-3f078b450569105ded83JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002e-0009500000-ec62c372df35c3083214JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-1009200000-7f445ec03fa57924e2f5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-a071385ec6b10bec9802JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0007900000-a679f216bf445402e2f4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-1009300000-0d8a0e3dbdcfdc36b405JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0004900000-6ab84f25551330952892JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-7829500000-6c46f5c397c9c07c620dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0apu-9448000000-f2eb3b928ee415bf05f9JSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID50591
HMDB IDHMDB0062383
Pubchem Compound ID22298938
Kegg IDNot Available
ChemSpider ID24850067
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
3-beta-hydroxy-4-beta-methyl-5-alpha-cholest- 7-ene-4-alpha-carboxylate + NAD(P)(+) = 4-alpha-methyl-5-alpha- cholest-7-en-3-one + CO(2) + NAD(P)H
Gene Name:
ERG26
Uniprot ID:
P53199
Molecular weight:
38706.10156
Reactions
3-beta-hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carboxylate + NAD(P)(+) → 4-alpha-methyl-5-alpha-cholest-7-en-3-one + CO(2) + NAD(P)H.
Protein Details
2. C-4 methylsterol oxidase
General function:
Involved in iron ion binding
Specific function:
Catalyzes the first step in the removal of the two C-4 methyl groups of 4,4-dimethylzymosterol
Gene Name:
ERG25
Uniprot ID:
P53045
Molecular weight:
36478.89844
Reactions
4,4-dimethyl-5-alpha-cholest-7-en-3-beta-ol + NAD(P)H + O(2) → 4-beta-hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol + NAD(P)(+) + H(2)O.
4-beta-hydroxymethyl-4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol + NAD(P)H + O(2) → 3-beta-hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carbaldehyde + NAD(P)(+) + 2 H(2)O.
3-beta-hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carbaldehyde + NAD(P)H + O(2) → 3-beta-hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carboxylate + NAD(P)(+) + H(2)O.