2-Hydroxybutyric Acid
PubChem CID: 11266
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| Compound Synonyms | 2-Hydroxybutyric acid, 2-HYDROXYBUTANOIC ACID, 600-15-7, dl-2-hydroxy-n-butyric acid, DL-2-Hydroxybutyric Acid, Butanoic acid, 2-hydroxy-, alpha-Hydroxybutyric acid, 565-70-8, alpha-Hydroxybutyrate, 2-hydroxy-butanoic acid, Butyric acid, 2-hydroxy-, (1)-2-Hydroxybutyric acid, O0ADR0I4H5, alpha-Hydroxy-n-butyric acid, CHEBI:1148, Hydroxybutyric acid, NSC 6495, NSC-6495, alpha-hydroxybutanoic acid, EINECS 209-985-3, MFCD00070502, DL-2-Hydroxybutanoic acid, .alpha.-Hydroxybutyric acid, (RS)-2-Hydroxybutyric acid, 2-Hydroxy-butyric acid anion, (+/-)-2-hydroxybutanoic acid, .alpha.-Hydroxy-n-butyric acid, BUTANOIC ACID, 2-HYDROXY-, (+/-)-, S-2-hydroxybutyric acid, (R)-alpha-Hydroxybutyric acid, UNII-O0ADR0I4H5, ethylglycolic acid, -hydroxybutyric acid, DL2Hydroxybutyric acid, 2-hydroxy-butyric acid, alpha-hydroxy butyric acid, SCHEMBL6963, ?-HYDROXYBUTYRIC ACID, CHEMBL567588, DTXSID8041903, (+/-)alpha-hydoxy butyric acid, Butyric acid, 2-hydroxy-(8CI), NSC6495, Butanoic acid, 2-hydroxy-(9CI), (R)-(+)-2-Hydroxybutanoic acid, 2-Hydroxybutanoic acid, AldrichCPR, BCP33336, LMFA01050004, s6119, AKOS000121162, AKOS016053528, FH35031, SB44466, SB44876, SY066872, SY234828, DB-017417, DB-066029, HY-113381, CS-0062339, H0227, NS00034281, NS00120051, EN300-27738, D90822, BC3EA1BE-590C-48AC-ACE7-8989B8E96BFC, Q3288610, Z246073650, DL-2-Hydroxybutyric Acid (contains Polymolecular esterification product) |
|---|---|
| Topological Polar Surface Area | 57.5 |
| Hydrogen Bond Donor Count | 2.0 |
| Heavy Atom Count | 7.0 |
| Description | 2-Hydroxybutyric acid is an organic acid that is involved in propanoate metabolism. It is produced in mammalian tissues (principaly hepatic) that catabolize L-threonine or synthesize glutathione. Oxidative stress or detoxification demands can dramatically increase the rate of hepatic glutathione synthesis. Under such metabolic stress conditions, supplies of L-cysteine for glutathione synthesis become limiting, so homocysteine is diverted from the transmethylation pathway forming methionine into the transsulfuration pathway forming cystathionine. 2-Hydroxybutyrate is released as a by-product when cystathionine is cleaved to cysteine that is incorporated into glutathione. 2-Hydroxybutyric acid is often found in the urine of patients suffering from lactic acidosis and ketoacidosis. 2-Hydroxybutyric acid generally appears at high concentrations in situations related to deficient energy metabolism (e.g., birth asphyxia) and also in inherited metabolic diseases affecting the central nervous system during neonatal development, such as "cerebral" lactic acidosis, glutaric aciduria type II, dihydrolipoyl dehydrogenase (E3) deficiency, and propionic acidemia. More recently it has been noted that elevated levels of alpha-hydroxybutyrate in the plasma is a good marker for early stage type II diabetes (PMID: 19166731). It was concluded from studies done in the mid 1970's that an increased NADH2/NAD ratio was the most important factor for the production of 2-hydorxybutyric acid (PMID: 168632) [HMDB] |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 69.3 |
| Database Name | cmaup_ingredients;fooddb_chem_all;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Uniprot Id | Q7Z4W1, Q969S8, O60669, P53987, O15427 |
| Iupac Name | 2-hydroxybutanoic acid |
| Prediction Hob | 1.0 |
| Class | Fatty Acyls |
| Xlogp | 0.1 |
| Superclass | Lipids and lipid-like molecules |
| Subclass | Fatty acids and conjugates |
| Molecular Formula | C4H8O3 |
| Prediction Swissadme | 0.0 |
| Inchi Key | AFENDNXGAFYKQO-UHFFFAOYSA-N |
| Fcsp3 | 0.75 |
| Logs | 0.384 |
| Rotatable Bond Count | 2.0 |
| State | Solid |
| Logd | -1.321 |
| Synonyms | (RS)-2-Hydroxybutyrate, (RS)-2-Hydroxybutyric acid, 2-hydroxy-Butanoate, 2-hydroxy-Butanoic acid, 2-hydroxy-DL-Butyrate, 2-hydroxy-DL-Butyric acid, 2-Hydroxy-n-butyrate, 2-Hydroxy-n-butyric acid, 2-Hydroxybutanoate, 2-Hydroxybutanoic acid, 2-Hydroxybutyrate, a-Hydroxy-n-butyrate, a-Hydroxy-n-butyric acid, a-Hydroxybutanoate, a-Hydroxybutanoic acid, a-Hydroxybutyrate, a-Hydroxybutyric acid, alpha-hydroxy-n-butyrate, alpha-hydroxy-n-butyric acid, alpha-Hydroxybutanoate, alpha-Hydroxybutanoic acid, alpha-Hydroxybutyrate, alpha-Hydroxybutyric acid, DL-2-Hydroxybutanoate, DL-2-Hydroxybutanoic acid, DL-a-Hydroxybutyrate, DL-a-Hydroxybutyric acid, DL-alpha-Hydroxybutyrate, DL-alpha-Hydroxybutyric acid, α-hydroxybutanoate, α-hydroxybutanoic acid, α-hydroxybutyrate, α-hydroxybutyric acid |
| Substituent Name | Hydroxy fatty acid, Hydroxy acid, Alpha-hydroxy acid, Secondary alcohol, Monocarboxylic acid or derivatives, Carboxylic acid, Carboxylic acid derivative, Hydrocarbon derivative, Organooxygen compound, Carbonyl group, Alcohol, Aliphatic acyclic compound |
| Compound Name | 2-Hydroxybutyric Acid |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 104.047 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 104.047 |
| Hydrogen Bond Acceptor Count | 3.0 |
| Molecular Weight | 104.1 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 1.0 |
| Total Bond Stereocenter Count | 0.0 |
| Esol | -0.3912509999999998 |
| Inchi | InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7) |
| Smiles | CCC(C(=O)O)O |
| Nring | 0.0 |
| Defined Bond Stereocenter Count | 0.0 |
- 1. Outgoing r'ship
FOUND_INto/from Aloe Africana (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 2. Outgoing r'ship
FOUND_INto/from Aloe Barbadensis (Plant) Rel Props:Source_db:npass_chem_all - 3. Outgoing r'ship
FOUND_INto/from Aloe Ferox (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 4. Outgoing r'ship
FOUND_INto/from Aloe Spicata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 5. Outgoing r'ship
FOUND_INto/from Aloe Vera (Plant) Rel Props:Source_db:cmaup_ingredients - 6. Outgoing r'ship
FOUND_INto/from Chlamydomonas Reinhardtii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all