Showing Metabocard for (3R)-3-hydroxybutanoyl-CoA (BASm0002582)

Common Name(3r)-3-hydroxybutanoyl-coa
Description3-Hydroxybutyryl-CoA is a substrate for Enoyl-CoA hydratase (mitochondrial), Trifunctional enzyme alpha subunit (mitochondrial) and Peroxisomal bifunctional enzyme.
Structure
Molecular FormulaC25H42N7O18P3S
Average Mass853.62000
Monoisotopic Mass853.15199
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-3-({2-[(2-{[(3R)-3-hydroxybutanoyl]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-{[(3r)-3-hydroxybutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number21804-29-5
SMILESC[C@@H](O)CC(=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/C25H42N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-14,18-20,24,33,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,14-,18-,19-,20+,24-/m1/s1
InChI KeyQHHKKMYHDBRONY-WZZMXTMRSA-N
CHEBI IDCHEBI:57315
HMDB IDHMDB0001166
Pathways
NameSMPDB/PathBank
Lysine degradation
Fatty acid Metabolism
Butyrate Metabolism
Ethylmalonic Encephalopathy
Glutaric Aciduria Type I
Glutaric Aciduria Type I
Short Chain Acyl CoA Dehydrogenase Deficiency (SCAD Deficiency)
Saccharopinuria/Hyperlysinemia II
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids
Hyperlysinemia I, Familial
Hyperlysinemia II or Saccharopinuria
Carnitine palmitoyl transferase deficiency (I)
Long chain acyl-CoA dehydrogenase deficiency (LCAD)
Very-long-chain acyl coa dehydrogenase deficiency (VLCAD)
Carnitine palmitoyl transferase deficiency (II)
Medium chain acyl-coa dehydrogenase deficiency (MCAD)
Trifunctional protein deficiency
Short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (SCHAD)
Pyridoxine dependency with seizures
2-aminoadipic 2-oxoadipic aciduria
StateSolid
Water Solubility4.07e+00 g/l
logP-0.62
logS-2.32
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
Refractivity183.03 m³·mol⁻¹
Polarizability75.89

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