Showing Metabocard for (2S,3S)-3-hydroxy-2-methylbutanoyl-CoA (BASm0002579)

Common Name(2s,3s)-3-hydroxy-2-methylbutanoyl-coa
Description2-Methyl-3-hydroxybutyryl-CoA (CAS: 6701-38-8) belongs to the class of organic compounds known as (S)-3-hydroxyacyl-CoAs. These are organic compounds containing an (S)-3-hydroxyl acylated coenzyme A derivative. Thus, 2-methyl-3-hydroxybutyryl-CoA is considered to be a fatty ester lipid molecule. 2-Methyl-3-hydroxybutyryl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Methyl-3-hydroxybutyryl-CoA is a substrate for 3-hydroxyacyl-CoA dehydrogenase type II, enoyl-CoA hydratase, trifunctional enzyme alpha subunit, short-chain 3-hydroxyacyl-CoA dehydrogenase, and peroxisomal bifunctional enzyme.
Structure
Molecular FormulaC26H44N7O18P3S
Average Mass867.65000
Monoisotopic Mass867.16764
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-3-({2-[(2-{[(2S,3S)-3-hydroxy-2-methylbutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-3-({2-[(2-{[(2s,3s)-3-hydroxy-2-methylbutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number1169932-06-2
SMILESC[C@H](O)[C@H](C)C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)([O-])[O-]
InChI IdentifierInChI=1S/C26H44N7O18P3S/c1-13(14(2)34)25(39)55-8-7-28-16(35)5-6-29-23(38)20(37)26(3,4)10-48-54(45,46)51-53(43,44)47-9-15-19(50-52(40,41)42)18(36)24(49-15)33-12-32-17-21(27)30-11-31-22(17)33/h11-15,18-20,24,34,36-37H,5-10H2,1-4H3,(H,28,35)(H,29,38)(H,43,44)(H,45,46)(H2,27,30,31)(H2,40,41,42)/t13-,14-,15+,18+,19+,20-,24+/m0/s1
InChI KeyPEKYNTFSOBAABV-LQUDNSJZSA-N
CHEBI IDCHEBI:57312
HMDB IDHMDB0001356
Pathways
NameSMPDB/PathBank
Valine, leucine and isoleucine degradation
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency
3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency
3-Methylglutaconic Aciduria Type I
3-Methylglutaconic Aciduria Type III
3-Methylglutaconic Aciduria Type IV
Beta-Ketothiolase Deficiency
Maple Syrup Urine Disease
Methylmalonic Aciduria
Propionic Acidemia
3-Methylcrotonyl Coa Carboxylase Deficiency Type I
Isovaleric Aciduria
Methylmalonate Semialdehyde Dehydrogenase Deficiency
3-hydroxyisobutyric acid dehydrogenase deficiency
3-hydroxyisobutyric aciduria
Isobutyryl-coa dehydrogenase deficiency
Isovaleric acidemia
StateSolid
Water Solubility3.96e+00 g/l
logP-0.48
logS-2.34
pKa (Strongest Acidic)0.83
pKa (Strongest Basic)4.95
Hydrogen Acceptor Count18
Hydrogen Donor Count10
Polar Surface Area383.86 Ų
Rotatable Bond Count22
Physiological Charge-4
Formal Charge0
Refractivity187.60 m³·mol⁻¹
Polarizability77.15

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