Glycodeoxycholic Acid

Details

• Internal ID: 0d4d94b3-57bf-4d04-97a6-2ac1eb6f71b8
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Glycinated bile acids and derivatives
• IUPAC Name: 2-[[(4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid
• InChI: InChI=1S/C26H43NO5/c1-15(4-9-23(30)27-14-24(31)32)19-7-8-20-18-6-5-16-12-17(28)10-11-25(16,2)21(18)13-22(29)26(19,20)3/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17-,18+,19-,20+,21+,22+,25+,26-/m1/s1
• InChI Key: WVULKSPCQVQLCU-BUXLTGKBSA-N
• Popularity: 290 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₃NO₅
• Molecular Weight: 449.60 g/mol
• Exact Mass: 449.31412347 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.59
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• Deoxycholylglycine
• Glycodeoxycholate
• 360-65-6
• Glycodesoxycholic acid
• GDCA
• Deoxycholic acid glycine conjugate
• Deoxyglycocholic acid
• Glycyldeoxycholic acid
• CHEMBL258605
• CHEBI:27471
• DS124M0828
• Sodium glycyldeoxycholate
• Glycodeoxycholate (Sodium)
• N-(3alpha,12alpha-dihydroxy-5beta-cholan-24-oyl)glycine
• Glycine, N-(3.alpha.,12.alpha.-dihydroxy-5.beta.-cholan-24-oyl)-
• Glykodesoxycholsaeure
• Glykodesoxycholsaeure [German]
• UNII-DS124M0828
• Glycine, N-((3alpha,5beta,12alpha)-3,12-dihydroxy-24-oxocholan-24-yl)-
• GLYCINE, N-((3.ALPHA.,5.BETA.,12.ALPHA.)-3,12-DIHYDROXY-24-OXOCHOLAN-24-YL)-
• Glycine, N-[(3.alpha.,5.beta.,12.alpha.)-3,12-dihydroxy-24-oxocholan-24-yl]-
• Glycine, N-[(3a,5b,12a)-3,12-dihydroxy-24-oxocholan-24-yl]-
• Glykodesoxycholsaure
• 5-beta-Cholan-24-oic acid, glycodeoxy-
• Cholane, glycine deriv.
• Spectrum5_002013
• bmse000644
• GLYCODEOXYCHOLIC_ACID
• SCHEMBL24841
• GTPL4714
• BDBM50375587
• LMST05030006
• AKOS025290392
• 2-[[(4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid
• HY-125731
• CS-0093438
• C05464
• F20550
• G-5420
• Q5572601
• 3alpha,12alpha-Dihydroxy-5beta-cholan-24-oylglycine
• BRD-K68144790-001-01-2
• N-(3alpha,12alpha-dihydroxy-5beta-cholan-24-oyl)-glycine
• GLYCINE, N-(3-alpha,12-alpha-DIHYDROXY-5-beta-CHOLAN-24-YL)-
• 3.ALPHA.,12.ALPHA.-DIHYDROXY-5.BETA.-CHOLANIC ACID-24-GLYCINE
• 5.beta.-Cholan-24-amide, N-(carboxymethyl)-3.alpha.,12.alpha.-dihydroxy-
• N-((3-alpha,5-beta,12-alpha)-3,12-Dihydroxy-24-oxocholan-24-yl)-glycine
• 2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9010	90.10%
Caco-2	-	0.8991	89.91%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7881	78.81%
OATP2B1 inhibitior	+	1.0000	100.00%
OATP1B1 inhibitior	+	0.8336	83.36%
OATP1B3 inhibitior	+	0.9371	93.71%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8064	80.64%
BSEP inhibitior	+	0.6213	62.13%
P-glycoprotein inhibitior	-	0.5606	56.06%
P-glycoprotein substrate	+	0.6542	65.42%
CYP3A4 substrate	+	0.7251	72.51%
CYP2C9 substrate	+	0.5320	53.20%
CYP2D6 substrate	-	0.8412	84.12%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9382	93.82%
CYP2C8 inhibition	-	0.6612	66.12%
CYP inhibitory promiscuity	-	0.8426	84.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6707	67.07%
Eye corrosion	-	0.9941	99.41%
Eye irritation	-	0.9012	90.12%
Skin irritation	-	0.7388	73.88%
Skin corrosion	-	0.9552	95.52%
Ames mutagenesis	-	0.5701	57.01%
Human Ether-a-go-go-Related Gene inhibition	-	0.5260	52.60%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.5217	52.17%
skin sensitisation	-	0.9078	90.78%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.9216	92.16%
Acute Oral Toxicity (c)	III	0.6594	65.94%
Estrogen receptor binding	-	0.7766	77.66%
Androgen receptor binding	+	0.7564	75.64%
Thyroid receptor binding	+	0.7966	79.66%
Glucocorticoid receptor binding	+	0.8032	80.32%
Aromatase binding	+	0.7034	70.34%
PPAR gamma	+	0.5556	55.56%
Honey bee toxicity	-	0.7512	75.12%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9167	91.67%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	97.76%	90.17%
CHEMBL220	P22303	Acetylcholinesterase	97.18%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.12%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.15%	98.95%
CHEMBL2179	P04062	Beta-glucocerebrosidase	93.49%	85.31%
CHEMBL237	P41145	Kappa opioid receptor	92.90%	98.10%
CHEMBL1914	P06276	Butyrylcholinesterase	92.66%	95.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.76%	91.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.93%	90.71%
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	88.35%	88.81%
CHEMBL340	P08684	Cytochrome P450 3A4	88.32%	91.19%
CHEMBL2094135	Q96BI3	Gamma-secretase	87.53%	98.05%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.37%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.88%	97.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.52%	100.00%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	86.51%	96.00%
CHEMBL233	P35372	Mu opioid receptor	86.46%	97.93%
CHEMBL236	P41143	Delta opioid receptor	86.25%	99.35%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	85.86%	96.38%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.83%	95.89%
CHEMBL238	Q01959	Dopamine transporter	85.18%	95.88%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	84.86%	96.03%
CHEMBL2514	O95665	Neurotensin receptor 2	84.82%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.76%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.59%	99.23%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.44%	82.69%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	83.93%	97.86%
CHEMBL274	P51681	C-C chemokine receptor type 5	83.57%	98.77%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.91%	89.05%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	82.53%	99.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.29%	97.50%
CHEMBL4246	P42680	Tyrosine-protein kinase TEC	81.52%	82.05%
CHEMBL1075317	P61964	WD repeat-containing protein 5	81.07%	96.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.04%	96.47%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	80.65%	96.67%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.62%	94.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.59%	93.56%
CHEMBL3921	Q9Y251	Heparanase	80.56%	94.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.32%	93.00%
CHEMBL5028	O14672	ADAM10	80.29%	97.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.16%	96.77%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 3035026
• LOTUS: LTS0217717
• wikiData: Q5572601