Showing metabocard for 4a-Methylzymosterol-4-carboxylic acid (BMDB0006927)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:27:36 UTC
Update Date2020-05-21 16:28:43 UTC
BMDB IDBMDB0006927
Secondary Accession Numbers
  • BMDB06927
Metabolite Identification
Common Name4a-Methylzymosterol-4-carboxylic acid
Description2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylate, also known as 5-formyl-3-hydroxy-2-methylpyridine-4-carboxylic acid or 5-formyl-3-hydroxy-2-methylisonicotinate, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. 2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylate is a moderately basic compound (based on its pKa). In cattle, 2-methyl-3-hydroxy-5-formylpyridine-4-carboxylate is involved in the metabolic pathway called the vitamin B6 metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Methyl-3-hydroxy-5-formylpyridine-4-carboxylic acidChEBI
5-Formyl-3-hydroxy-2-methyl-4-pyridinecarboxylic acidChEBI
5-Formyl-3-hydroxy-2-methylisonicotinic acidChEBI
5-Formyl-3-hydroxy-2-methylpyridine-4-carboxylateKegg
5-Formyl-3-hydroxy-2-methyl-4-pyridinecarboxylateGenerator
5-Formyl-3-hydroxy-2-methylisonicotinateGenerator
5-Formyl-3-hydroxy-2-methylpyridine-4-carboxylic acidGenerator
4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-olHMDB
4alpha-Methylzymosterol-4-carboxylic acidHMDB
4a-Methylzymosterol-4-carboxylateGenerator
Chemical FormulaC29H46O3
Average Molecular Weight442.6737
Monoisotopic Molecular Weight442.344695338
IUPAC Name(2S,5S,6S,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2S)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-6-carboxylic acid
Traditional Name(2S,5S,6S,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2S)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-6-carboxylic acid
CAS Registry NumberNot Available
SMILES
C[C@@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)(C1CC3)C(O)=O
InChI Identifier
InChI=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-/m0/s1
InChI KeyMYWAIWDQTCHPTH-IUGQOUSLSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentPyridinecarboxylic acids
Alternative Parents
Substituents
  • Pyridine carboxylic acid
  • 3-pyridine carboxaldehyde
  • Aryl-aldehyde
  • Hydroxypyridine
  • Methylpyridine
  • Vinylogous acid
  • Heteroaromatic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Aldehyde
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability54.54 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-2009500000-d95a96ec50d214c4a7adView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-3001290000-49cf623a8c01d727af89View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0003900000-ede2074ebef5c7b4f5efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-3009600000-668782b6420b243b39abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar9-4129200000-aa72815365e75b94ccbcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0003900000-8cabb8e5bbac4a6dfdf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002e-0009500000-4c342723259093956de9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-1009200000-1be86c464989109fde9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-a071385ec6b10bec9802View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0005900000-7395cb3ac36e70ff026aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-3004900000-d631319845841e3d35f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0005900000-201f4ae9e2e8593bb420View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gwo-4249500000-9b29d5f0aa9ef228b757View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9778000000-4438f729f0f6c14e77d9View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006954
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024160
KNApSAcK IDNot Available
Chemspider ID389728
KEGG Compound IDC06050
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440898
PDB IDNot Available
ChEBI ID28038
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Involved in the sequential removal of two C-4 methyl groups in post-squalene cholesterol biosynthesis.
Gene Name:
NSDHL
Uniprot ID:
Q3ZBE9
Molecular weight:
39902.0
Reactions
4a-Methylzymosterol-4-carboxylic acid + NADP → 3-Keto-4-methylzymosterol + NADPH + Carbon dioxidedetails
Enzyme Details
2. Methylsterol monooxygenase 1
General function:
Not Available
Specific function:
Not Available
Gene Name:
MSMO1
Uniprot ID:
A6H7G3
Molecular weight:
35061.0
Reactions
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + 3 NADPH + 3 Oxygen → 4a-Methylzymosterol-4-carboxylic acid +3 NADP +4 Waterdetails