Β-Hydroxybutyryl-CoA

β-Hydroxybutyryl-CoA (or 3-hydroxybutyryl-coenzyme A) is an intermediate in the fermentation of butyric acid, and in the metabolism of lysine and tryptophan.^[1][2] The L-3-hydroxybutyl-CoA (or (S)-3-hydroxybutanoyl-CoA) enantiomer is also the second to last intermediate in beta oxidation of even-numbered, straight chain, and saturated fatty acids.^[3]

β-Hydroxybutyryl-CoA

Names
IUPAC name {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-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
Identifiers
CAS Number	2871-66-1 N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:37050
ChemSpider	559120
DrugBank	DB03612
KEGG	C05116
PubChem CID	644065
CompTox Dashboard (EPA)	DTXSID90951355
InChI InChI=1/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 Key: QHHKKMYHDBRONY-JYMPOPDUBN
SMILES CC(CC(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)O)O
Properties
Chemical formula	C25H42N7O18P3S
Molar mass	853.625 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

See also

• Crotonyl-coenzyme A
• Acetoacetyl CoA
• Beta-hydroxybutyryl-CoA dehydrogenase

References

1. Numa, S.; Ishimura, Y.; Nishizuka, Y.; Hayaishi, O. (1961-10-23). "beta-Hydroxybutyryl-CoA, an intermediate in glutarate catabolism". Biochemical and Biophysical Research Communications. 6: 38–43. doi:10.1016/0006-291x(61)90181-4. ISSN 0006-291X. PMID 14480702.
2. Liu, Shumeng; Yu, Huajing; Liu, Yongqing; Liu, Xinhua; Zhang, Yu; Bu, Chen; Yuan, Shuai; Chen, Zhe; Xie, Guojia; Li, Wanjin; Xu, Bosen; Yang, Jianguo; He, Lin; Jin, Tong; Xiong, Yundong (2017-09-07). "Chromodomain Protein CDYL Acts as a Crotonyl-CoA Hydratase to Regulate Histone Crotonylation and Spermatogenesis". Molecular Cell. 67 (5): 853–866.e5. doi:10.1016/j.molcel.2017.07.011. ISSN 1097-4164. PMID 28803779.
3. van Rijt, Willemijn J.; Van Hove, Johan L. K.; Vaz, Frédéric M.; Havinga, Rick; Allersma, Derk P.; Zijp, Tanja R.; Bedoyan, Jirair K.; Heiner-Fokkema, M. R.; Reijngoud, Dirk-Jan; Geraghty, Michael T.; Wanders, Ronald J. A.; Oosterveer, Maaike H.; Derks, Terry G. J. (July 2021). "Enantiomer-specific pharmacokinetics of D,L-3-hydroxybutyrate: Implications for the treatment of multiple acyl-CoA dehydrogenase deficiency". Journal of Inherited Metabolic Disease. 44 (4): 926–938. doi:10.1002/jimd.12365. ISSN 1573-2665. PMC 8359440. PMID 33543789.