4-Amino-3-hydroxybutyric acid

Details

• Internal ID: 5975c1d6-768f-48a2-9ded-aefd45e5a3ab
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Amino acids and derivatives > Gamma amino acids and derivatives
• IUPAC Name: 4-amino-3-hydroxybutanoic acid
• SMILES (Canonical): C(C(CN)O)C(=O)O
• SMILES (Isomeric): C(C(CN)O)C(=O)O
• InChI: InChI=1S/C4H9NO3/c5-2-3(6)1-4(7)8/h3,6H,1-2,5H2,(H,7,8)
• InChI Key: YQGDEPYYFWUPGO-UHFFFAOYSA-N
• Popularity: 130 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄H₉NO₃
• Molecular Weight: 119.12 g/mol
• Exact Mass: 119.058243149 g/mol
• Topological Polar Surface Area (TPSA): 83.60 Ų
• XlogP: -4.10
• Atomic LogP (AlogP): -1.22
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• 4-Amino-3-hydroxybutyric acid
• 4-Amino-3-hydroxybutanoic acid
• Gabob
• DL-4-Amino-3-hydroxybutyric acid
• Gamibetal
• 352-21-6
• Gabomade
• 3-Hydroxy-GABA
• Gamma-amino-beta-hydroxybutyric acid
• Buksamin
• Gaboril
• Butanoic acid, 4-amino-3-hydroxy-
• Gabimex
• Gaminal
• Idramina
• Bogil
• Buxamine
• Gabobe
• 3-Hydroxy-4-aminobutyric acid
• aminohydroxybutyric acid
• NSC 40244
• 4-Amino-3-hydroxy-butyric acid
• BUTYRIC ACID, 4-AMINO-3-HYDROXY-
• Gamma-amino-beta-hydroxybutyric acid [JAN]
• MFCD00008141
• 4-amino-3-hydroxybutyrate
• 1ZHM019FLD
• .gamma.-Amino-.beta.-hydroxybutyric acid
• 4-Amino-3-hydroxybutanoicacid
• DTXSID1045877
• CHEBI:16080
• 4-Amino-3-hydroxybutanoate
• dl-4-amino-3-hydroxybutanoic acid
• (S)-4-Amino-3-Hydroxybutyric acid
• NSC-40244
• NCGC00094987-01
• .beta.-Hydroxy-.gamma.-aminobutyric acid
• Buxamin
• beta-Oxy-gaba
• Buxamine (VAN)
• gamma-Amino-beta-hydroxybutyric acid (JAN)
• beta-Hydroxy-gamma-aminobutyrate
• gamma-Amino-beta-hydroxybutyrate
• 4-amino-3-hydroxy-butanoic acid
• beta-Hydroxy-alpha-aminobutyric acid
• D,L-4-Amino-3-hydroxybutyric acid
• EINECS 206-518-5
• EINECS 213-106-9
• (+-)-4-Amino-3-hydroxybutyric acid
• UNII-1ZHM019FLD
• MFCD00672884
• .beta.-Hydroxy-GABA
• Spectrum_001276
• Spectrum2_001129
• Spectrum3_001548
• Spectrum4_000301
• Spectrum5_001124
• SCHEMBL38621
• BSPBio_002996
• KBioGR_000882
• KBioSS_001756
• CHEMBL93515
• DivK1c_000116
• SPECTRUM1503041
• SPBio_000997
• DTXCID9025877
• 3-hydroxy-4-amino butanoic acid
• HMS500F18
• KBio1_000116
• KBio2_001756
• KBio2_004324
• KBio2_006892
• KBio3_002496
• YQGDEPYYFWUPGO-UHFFFAOYSA-
• 3-Hydroxy-4-Amino Butyric Acid
• gamma-amino-3-hydroxybutyric acid
• NINDS_000116
• 4-Amino-3-hydroxybutanoic acid #
• HMS1922A11
• Pharmakon1600-01503041
• rac-4-amino-3-hydroxybutyric acid
• (S)-4-Amino-3-hydroxybutyricacid
• HY-B1427
• NSC40244
• Tox21_111375
• AB3028
• CCG-40012
• NSC758215
• .beta.-Hydroxy-.gamma.-aminobutyrate
• .gamma.-Amino-.beta.-hydroxybutyrate
• 4-Amino-3-hydroxybutyric acid, 98%
• AKOS015892786
• (+/-)-4-amino-3-hydroxybutyric acid
• NSC-758215
• IDI1_000116
• NCGC00094987-02
• NCGC00094987-03
• AS-44677
• CAS-924-49-2
• SY045503
• SY050892
• SY110230
• (.+/-.)-4-Amino-3-hydroxybutyric acid
• SBI-0051753.P002
• .gamma.-Amino-.beta.-hydroxy-n-butyric acid
• 4-AMINO-3-HYDROXYBUTYRIC ACID [MI]
• A0318
• CS-0013138
• FT-0632015
• FT-0636332
• FT-0636333
• FT-0716832
• 4-AMINO-3-HYDROXYBUTYRIC ACID [INCI]
• EN300-96299
• 4-AMINO-3-HYDROXYBUTYRIC ACID [MART.]
• C03678
• D00174
• 4-AMINO-3-HYDROXYBUTYRIC ACID [WHO-DD]
• AB00052302_02
• BUTYRIC ACID, 4-AMINO-3-HYDROXY-, DL-
• A844239
• Butanoic acid, 4-amino-3-hydroxy-, (.+/-.)-
• SR-01000872771
• Q5520257
• SR-01000872771-1
• BUTANOIC ACID, 4-AMINO-3-HYDROXY-, (+/-)-
• Z1255390571
• 80297B30-DF98-4F62-A800-277359B3BBE8
• InChI=1/C4H9NO3/c5-2-3(6)1-4(7)8/h3,6H,1-2,5H2,(H,7,8)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7696	76.96%
Caco-2	-	0.7699	76.99%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Lysosomes	0.4903	49.03%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.9705	97.05%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9607	96.07%
P-glycoprotein inhibitior	-	0.9863	98.63%
P-glycoprotein substrate	-	0.9787	97.87%
CYP3A4 substrate	-	0.7837	78.37%
CYP2C9 substrate	-	0.5894	58.94%
CYP2D6 substrate	-	0.7141	71.41%
CYP3A4 inhibition	-	0.9324	93.24%
CYP2C9 inhibition	-	0.9594	95.94%
CYP2C19 inhibition	-	0.9212	92.12%
CYP2D6 inhibition	-	0.9338	93.38%
CYP1A2 inhibition	-	0.9310	93.10%
CYP2C8 inhibition	-	0.9949	99.49%
CYP inhibitory promiscuity	-	0.9747	97.47%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7920	79.20%
Carcinogenicity (trinary)	Non-required	0.5907	59.07%
Eye corrosion	-	0.9391	93.91%
Eye irritation	+	0.9266	92.66%
Skin irritation	-	0.7397	73.97%
Skin corrosion	-	0.9324	93.24%
Ames mutagenesis	-	0.8124	81.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.8204	82.04%
Micronuclear	-	0.7626	76.26%
Hepatotoxicity	+	0.6159	61.59%
skin sensitisation	-	0.9485	94.85%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	-	0.8111	81.11%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7211	72.11%
Acute Oral Toxicity (c)	IV	0.6269	62.69%
Estrogen receptor binding	-	0.9506	95.06%
Androgen receptor binding	-	0.8671	86.71%
Thyroid receptor binding	-	0.8442	84.42%
Glucocorticoid receptor binding	-	0.8336	83.36%
Aromatase binding	-	0.8514	85.14%
PPAR gamma	-	0.7082	70.82%
Honey bee toxicity	-	0.9390	93.90%
Biodegradation	+	0.8000	80.00%
Crustacea aquatic toxicity	-	0.9700	97.00%
Fish aquatic toxicity	-	0.9824	98.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.93%	96.09%
CHEMBL2581	P07339	Cathepsin D	85.26%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.28%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.50%	99.17%
CHEMBL1255126	O15151	Protein Mdm4	81.86%	90.20%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.79%	85.14%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	80.49%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 2149
• LOTUS: LTS0027836
• wikiData: Q5520257