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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-09-04 16:11:35 UTC
Update Date2022-03-07 02:49:34 UTC
HMDB IDHMDB0006927
Secondary Accession Numbers
  • HMDB06927
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 humans, 2-methyl-3-hydroxy-5-formylpyridine-4-carboxylate is involved in the metabolic disorder called the hypophosphatasia pathway. A pyridinemonocarboxylic acid that is pyridine-4-carboxylic acid substituted by a methyl group, hydroxy group and formyl group at positions 2,3 and 5, respectively.
Structure
Data?1582752415
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
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability54.54 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+208.19831661259
DarkChem[M-H]-201.62631661259
DeepCCS[M-2H]-240.56130932474
DeepCCS[M+Na]+215.98530932474
AllCCS[M+H]+213.132859911
AllCCS[M+H-H2O]+211.232859911
AllCCS[M+NH4]+214.832859911
AllCCS[M+Na]+215.232859911
AllCCS[M-H]-213.532859911
AllCCS[M+Na-2H]-215.632859911
AllCCS[M+HCOO]-218.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4a-Methylzymosterol-4-carboxylic acidC[C@@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)(C1CC3)C(O)=O3338.6Standard polar33892256
4a-Methylzymosterol-4-carboxylic acidC[C@@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)(C1CC3)C(O)=O3345.7Standard non polar33892256
4a-Methylzymosterol-4-carboxylic acidC[C@@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)(C1CC3)C(O)=O3566.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4a-Methylzymosterol-4-carboxylic acid,1TMS,isomer #1CC(C)=CCC[C@H](C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)[C@@](C)(C(=O)O)C1CC33593.7Semi standard non polar33892256
4a-Methylzymosterol-4-carboxylic acid,1TMS,isomer #2CC(C)=CCC[C@H](C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)[C@@](C)(C(=O)O[Si](C)(C)C)C1CC33509.0Semi standard non polar33892256
4a-Methylzymosterol-4-carboxylic acid,2TMS,isomer #1CC(C)=CCC[C@H](C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)[C@@](C)(C(=O)O[Si](C)(C)C)C1CC33515.8Semi standard non polar33892256
4a-Methylzymosterol-4-carboxylic acid,1TBDMS,isomer #1CC(C)=CCC[C@H](C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@](C)(C(=O)O)C1CC33808.6Semi standard non polar33892256
4a-Methylzymosterol-4-carboxylic acid,1TBDMS,isomer #2CC(C)=CCC[C@H](C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)C1CC33760.9Semi standard non polar33892256
4a-Methylzymosterol-4-carboxylic acid,2TBDMS,isomer #1CC(C)=CCC[C@H](C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)C1CC34002.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-2009500000-d95a96ec50d214c4a7ad2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00di-3001290000-49cf623a8c01d727af892017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 10V, Positive-QTOFsplash10-004i-0003900000-ede2074ebef5c7b4f5ef2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 20V, Positive-QTOFsplash10-056r-3009600000-668782b6420b243b39ab2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 40V, Positive-QTOFsplash10-0ar9-4129200000-aa72815365e75b94ccbc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 10V, Negative-QTOFsplash10-0006-0003900000-8cabb8e5bbac4a6dfdf52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 20V, Negative-QTOFsplash10-002e-0009500000-4c342723259093956de92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 40V, Negative-QTOFsplash10-0059-1009200000-1be86c464989109fde9d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 10V, Negative-QTOFsplash10-0006-0000900000-a071385ec6b10bec98022021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 20V, Negative-QTOFsplash10-0006-0005900000-7395cb3ac36e70ff026a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 40V, Negative-QTOFsplash10-00ku-3004900000-d631319845841e3d35f22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 10V, Positive-QTOFsplash10-0006-0005900000-201f4ae9e2e8593bb4202021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 20V, Positive-QTOFsplash10-0gwo-4249500000-9b29d5f0aa9ef228b7572021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4a-Methylzymosterol-4-carboxylic acid 40V, Positive-QTOFsplash10-0a4l-9778000000-4438f729f0f6c14e77d92021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in iron ion binding
Specific function:
Not Available
Gene Name:
MSMO1
Uniprot ID:
Q15800
Molecular weight:
19470.325
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
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