Acetoxolone

Details

• Internal ID: 8e1be289-516f-4b7c-b723-3173888584c0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-acetyloxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
• SMILES (Canonical): CC(=O)OC1CCC2(C(C1(C)C)CCC3(C2C(=O)C=C4C3(CCC5(C4CC(CC5)(C)C(=O)O)C)C)C)C
• SMILES (Isomeric): CC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]3([C@@H]2C(=O)C=C4[C@]3(CC[C@@]5([C@H]4C[C@@](CC5)(C)C(=O)O)C)C)C)C
• InChI: InChI=1S/C32H48O5/c1-19(33)37-24-10-11-30(6)23(27(24,2)3)9-12-32(8)25(30)22(34)17-20-21-18-29(5,26(35)36)14-13-28(21,4)15-16-31(20,32)7/h17,21,23-25H,9-16,18H2,1-8H3,(H,35,36)/t21-,23-,24-,25+,28+,29-,30-,31+,32+/m0/s1
• InChI Key: FTQDJVZNPJRVPG-XWEVEMRCSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₈O₅
• Molecular Weight: 512.70 g/mol
• Exact Mass: 512.35017463 g/mol
• Topological Polar Surface Area (TPSA): 80.70 Ų
• XlogP: 7.00
• Atomic LogP (AlogP): 6.98
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• Acetylglycyrrhetinic acid
• Glycyrrhetinyl acetate
• Acetylglycyrrhetic acid
• Glycyrrhetic acid acetate
• Glycyrrhetinic acid acetate
• 6277-14-1
• (3beta,20beta)-3-Acetoxy-11-oxoolean-12-en-29-oic acid
• Uralenic acid, acetate
• EINECS 228-475-1
• NSC 35349
• NSC-35349
• 3-Acetyl-18-beta-glycyrrhetinic acid
• UNII-CWW961Q19K
• CHEMBL207413
• CWW961Q19K
• CHEBI:81306
• DGS 0110A
• DGS-0110A
• C32H48O5
• (3-beta,20-beta)-3-(Acetyloxy)-11-oxo-olean-12-en-29-oic acid
• Olean-12-en-29-oic acid, 3-(acetyloxy)-11-oxo-, (3-beta,20-beta)-
• ACETOXOLONE [MI]
• ACETOXOLONE [WHO-DD]
• (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-acetyloxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
• SCHEMBL135617
• DTXSID801031583
• NSC35349
• BDBM50188385
• AKOS016036176
• DB13640
• LS-98287
• 3-O-ACETYL-18.BETA.-GLYCYRRHETIC ACID
• C17734
• 3beta-(Acetyloxy)-11-oxoolean-12-en-30-oic acid
• Q4673282
• 3-beta-hydroxy-11-oxoolean-12-en-30-oic acid acetate
• Olean-12-en-30-oic acid, 3-.beta.-hydroxy-11-oxo-, acetate
• Olean-12-en-30-oic acid, 3-beta-hydroxy-11-oxo-, acetate
• (3-beta,20-beta)-3-(Acetyloxy)-11-oxoolean-12-en-29-oic acid
• 3.BETA.-HYDROXY-11-OXOOLEAN-12-EN-30-OIC ACID ACETATE
• (3.BETA.,20.BETA.)-3-(ACETYLOXY)-11-OXOOLEAN-12-EN-29-OIC ACID
• (3beta,18beta,20beta)-3-(Acetyloxy)-11-oxo-olean-12-en-29-oic acid
• Olean-12-en-30-oic acid, 3-beta-hydroxy-11-oxo-, acetate (7CI,8CI)
• OLEAN-12-EN-29-OIC ACID, 3-(ACETYLOXY)-11-OXO-, (3.BETA.,20.BETA.)-
• (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-acetoxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
• (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-acetoxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid
• 10-acetyloxy-2,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9932	99.32%
Caco-2	-	0.6155	61.55%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.9143	91.43%
OATP2B1 inhibitior	-	0.7177	71.77%
OATP1B1 inhibitior	-	0.7975	79.75%
OATP1B3 inhibitior	-	0.5699	56.99%
MATE1 inhibitior	-	0.5200	52.00%
OCT2 inhibitior	-	0.6071	60.71%
BSEP inhibitior	+	0.9396	93.96%
P-glycoprotein inhibitior	+	0.7391	73.91%
P-glycoprotein substrate	-	0.8515	85.15%
CYP3A4 substrate	+	0.6954	69.54%
CYP2C9 substrate	-	0.8058	80.58%
CYP2D6 substrate	-	0.9141	91.41%
CYP3A4 inhibition	-	0.8067	80.67%
CYP2C9 inhibition	-	0.8398	83.98%
CYP2C19 inhibition	-	0.8914	89.14%
CYP2D6 inhibition	-	0.9524	95.24%
CYP1A2 inhibition	-	0.7163	71.63%
CYP2C8 inhibition	+	0.4724	47.24%
CYP inhibitory promiscuity	-	0.9277	92.77%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Non-required	0.6575	65.75%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.9424	94.24%
Skin irritation	+	0.5901	59.01%
Skin corrosion	-	0.9664	96.64%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4168	41.68%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.7217	72.17%
skin sensitisation	-	0.5494	54.94%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.6839	68.39%
Acute Oral Toxicity (c)	III	0.8121	81.21%
Estrogen receptor binding	+	0.5784	57.84%
Androgen receptor binding	+	0.6960	69.60%
Thyroid receptor binding	+	0.6463	64.63%
Glucocorticoid receptor binding	+	0.8508	85.08%
Aromatase binding	+	0.7706	77.06%
PPAR gamma	+	0.6478	64.78%
Honey bee toxicity	-	0.7716	77.16%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5550	55.50%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4235	P28845	11-beta-hydroxysteroid dehydrogenase 1	800 nM; 3450 nM; 800 nM; 7138 nM; 7100 nM	IC50; IC50; IC50; IC50; IC50	PMID: 16759088; PMID: 16759088; via Super-PRED; PMID: 20851614; PMID: 21376605
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	201 nM; 750 nM; 750 nM; 201 nM	IC50; IC50; IC50; IC50	PMID: 16759088; PMID: 20851614; PMID: 21376605; via Super-PRED
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	49860 nM	IC50	PMID: 26900660
CHEMBL3180	O00748	Carboxylesterase 2	40510 nM	IC50	PMID: 26900660
CHEMBL3181	P14061	Estradiol 17-beta-dehydrogenase 1	18800 nM	IC50	PMID: 16759088
CHEMBL2789	P37059	Estradiol 17-beta-dehydrogenase 2	3780 nM	IC50	PMID: 16759088

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.24%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.33%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.69%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.94%	82.69%
CHEMBL2581	P07339	Cathepsin D	88.99%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	87.94%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.83%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.03%	93.00%
CHEMBL221	P23219	Cyclooxygenase-1	86.11%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.70%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.13%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.10%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.62%	99.23%

Plants that contains it

• Glycyrrhiza uralensis
• Mitracarpus hirtus

Cross-Links

• PubChem: 94320
• NPASS: NPC74751
• ChEMBL: CHEMBL207413
• LOTUS: LTS0060051
• wikiData: Q4673282