Showing Compound Card for 4a-Methylzymosterol-4-carboxylic acid (CDB005340)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (3) Show 4 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:33:23 UTC
Updated at2020-12-07 19:11:59 UTC
CannabisDB IDCDB005340
Secondary Accession NumbersNot Available
Cannabis Compound 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. 4a-Methylzymosterol-4-carboxylic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight442.67
Monoisotopic Molecular Weight442.3447
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4a-Methylzymosterol-4-carboxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-2009500000-d95a96ec50d214c4a7adSpectrum
Predicted GC-MS4a-Methylzymosterol-4-carboxylic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-3001290000-49cf623a8c01d727af89Spectrum
Predicted GC-MS4a-Methylzymosterol-4-carboxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0003900000-ede2074ebef5c7b4f5ef2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-3009600000-668782b6420b243b39ab2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar9-4129200000-aa72815365e75b94ccbc2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0003900000-8cabb8e5bbac4a6dfdf52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002e-0009500000-4c342723259093956de92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-1009200000-1be86c464989109fde9d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-a071385ec6b10bec98022021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0005900000-7395cb3ac36e70ff026a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-3004900000-d631319845841e3d35f22021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0005900000-201f4ae9e2e8593bb4202021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gwo-4249500000-9b29d5f0aa9ef228b7572021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9778000000-4438f729f0f6c14e77d92021-09-23View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Methylsterol monooxygenase 1MSMO14q32-q34Q15800 details
Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylatingNSDHLXq28Q15738 details
3-keto-steroid reductaseHSD17B71q23P56937 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Methylsterol monooxygenase 1MSMO14q32-q34Q15800 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0006954
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available

Enzymes

Enzyme Details
1. 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
2. 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
3. 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