ChemFOnt: Showing chemical card for 2-Methyl-1-hydroxybutyl-ThPP (CFc000007840)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:23 UTC

Chemfont ID

CFc000007840

Molecule Identification

Common Name

2-Methyl-1-hydroxybutyl-ThPP

Definition

2-Methyl-1-hydroxybutyl-ThPP is an intermediate in Valine, leucine and isoleucine degradation. 2-Methyl-1-hydroxybutyl-ThPP is the second to last step for the synthesis of (S)-2-Methylbutanoyl-CoA. 2-Methyl-1-hydroxybutyl-ThPP is converted from (S)-3-Methyl-2-oxopentanoic acid via the enzyme 2-oxoisovalerate dehydrogenase E1 component, alpha subunit(EC 1.2.4.4). It is then converted to S-(2-Methylbutanoyl)-dihydrolipoamide-E via the same enzyme.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Methyl-1-hydroxybutyl-TPP	Kegg

Chemical Formula

C₁₇H₂₉N₄O₈P₂S

Average Molecular Weight

511.447

Monoisotopic Molecular Weight

511.118132638

IUPAC Name

3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-2-[(2S)-1-hydroxy-2-methylbutyl]-4-methyl-1,3-thiazol-3-ium

Traditional Name

3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-2-[(2S)-1-hydroxy-2-methylbutyl]-4-methyl-1,3-thiazol-3-ium

CAS Registry Number

None

SMILES

CC[C@H](C)C(O)C1=[N+](CC2=CN=C(C)N=C2N)C(C)=C(CCOP(O)(=O)OP(O)(O)=O)S1

InChI Identifier

InChI=1S/C17H28N4O8P2S/c1-5-10(2)15(22)17-21(9-13-8-19-12(4)20-16(13)18)11(3)14(32-17)6-7-28-31(26,27)29-30(23,24)25/h8,10,15,22H,5-7,9H2,1-4H3,(H4-,18,19,20,23,24,25,26,27)/p+1/t10-,15?/m0/s1

InChI Key

CUBSXOWPMAOFDG-MYHCZTBNSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Thiamine phosphates

Alternative Parents

Substituents

Thiamine-phosphate
Organic pyrophosphate
2,4,5-trisubstituted 1,3-thiazole
Aminopyrimidine
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Imidolactam
Heteroaromatic compound
Azole
Thiazole
Secondary alcohol
Azacycle
Hydrocarbon derivative
Amine
Organic oxide
Primary amine
Alcohol
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Aromatic alcohol
Organic oxygen compound
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

thiamine phosphate (CHEBI:80223 )

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0012310)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.074 g/L	ALOGPS
logP	-0.18	ALOGPS
logP	-5.6	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	1.78	ChemAxon
pKa (Strongest Basic)	5.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.2 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	130.18 m³·mol⁻¹	ChemAxon
Polarizability	48.11 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012310

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028932

KNApSAcK ID

Not Available

Chemspider ID

35031876

KEGG Compound ID

C15978

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23724627

PDB ID

Not Available

ChEBI ID

80223

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 2-Methyl-1-hydroxybutyl-ThPP (CFc000007840)

MOL for CFc000007840 (2-Methyl-1-hydroxybutyl-ThPP)

3D MOL for CFc000007840 (2-Methyl-1-hydroxybutyl-ThPP)

3D SDF for CFc000007840 (2-Methyl-1-hydroxybutyl-ThPP)

3D-SDF for CFc000007840 (2-Methyl-1-hydroxybutyl-ThPP)

PDB for CFc000007840 (2-Methyl-1-hydroxybutyl-ThPP)

3D PDB for CFc000007840 (2-Methyl-1-hydroxybutyl-ThPP)

SMILES for CFc000007840 (2-Methyl-1-hydroxybutyl-ThPP)

INCHI for CFc000007840 (2-Methyl-1-hydroxybutyl-ThPP)

Structure for CFc000007840 (2-Methyl-1-hydroxybutyl-ThPP)

3D Structure for CFc000007840 (2-Methyl-1-hydroxybutyl-ThPP)