(3S,4S)-4-[(3R)-3-hydroxy-2-oxo-3-[(2S,3R,5S,9R,10R,12R,13S,14R,17S)-2,3,5,12,14-pentahydroxy-10,13-dimethyl-6-oxo-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]butyl]-3-methyloxolan-2-one

Details

• Internal ID: 3907668d-3a37-4031-98fa-640bc5b7760a
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives
• IUPAC Name: (3S,4S)-4-[(3R)-3-hydroxy-2-oxo-3-[(2S,3R,5S,9R,10R,12R,13S,14R,17S)-2,3,5,12,14-pentahydroxy-10,13-dimethyl-6-oxo-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]butyl]-3-methyloxolan-2-one
• SMILES (Canonical): CC1C(COC1=O)CC(=O)C(C)(C2CCC3(C2(C(CC4C3=CC(=O)C5(C4(CC(C(C5)O)O)C)O)O)C)O)O
• SMILES (Isomeric): C[C@H]1[C@@H](COC1=O)CC(=O)[C@@](C)([C@H]2CC[C@@]3([C@@]2([C@@H](C[C@H]4C3=CC(=O)[C@]5([C@@]4(C[C@@H]([C@@H](C5)O)O)C)O)O)C)O)O
• InChI: InChI=1S/C28H40O10/c1-13-14(12-38-23(13)34)7-21(32)26(4,35)19-5-6-27(36)16-9-22(33)28(37)11-18(30)17(29)10-24(28,2)15(16)8-20(31)25(19,27)3/h9,13-15,17-20,29-31,35-37H,5-8,10-12H2,1-4H3/t13-,14+,15-,17-,18+,19-,20+,24+,25-,26+,27+,28+/m0/s1
• InChI Key: ZYFVAVXYLVLPRL-HMKVZRANSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₀O₁₀
• Molecular Weight: 536.60 g/mol
• Exact Mass: 536.26214747 g/mol
• Topological Polar Surface Area (TPSA): 182.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -0.20
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9533	95.33%
Caco-2	-	0.7456	74.56%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8333	83.33%
OATP2B1 inhibitior	-	0.5726	57.26%
OATP1B1 inhibitior	+	0.8562	85.62%
OATP1B3 inhibitior	+	0.9488	94.88%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5662	56.62%
BSEP inhibitior	+	0.6339	63.39%
P-glycoprotein inhibitior	-	0.4712	47.12%
P-glycoprotein substrate	+	0.6342	63.42%
CYP3A4 substrate	+	0.6739	67.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9048	90.48%
CYP3A4 inhibition	-	0.7332	73.32%
CYP2C9 inhibition	-	0.8652	86.52%
CYP2C19 inhibition	-	0.9027	90.27%
CYP2D6 inhibition	-	0.9483	94.83%
CYP1A2 inhibition	-	0.8930	89.30%
CYP2C8 inhibition	-	0.5719	57.19%
CYP inhibitory promiscuity	-	0.9457	94.57%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4907	49.07%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9349	93.49%
Skin irritation	+	0.7012	70.12%
Skin corrosion	-	0.9336	93.36%
Ames mutagenesis	-	0.6470	64.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5089	50.89%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.5245	52.45%
skin sensitisation	-	0.9236	92.36%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.8539	85.39%
Acute Oral Toxicity (c)	III	0.5792	57.92%
Estrogen receptor binding	+	0.7165	71.65%
Androgen receptor binding	+	0.7692	76.92%
Thyroid receptor binding	+	0.5273	52.73%
Glucocorticoid receptor binding	+	0.7650	76.50%
Aromatase binding	+	0.7069	70.69%
PPAR gamma	-	0.5079	50.79%
Honey bee toxicity	-	0.8296	82.96%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9898	98.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.11%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.69%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.95%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.23%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.65%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.44%	100.00%
CHEMBL2581	P07339	Cathepsin D	91.64%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.52%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.31%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.01%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.66%	82.69%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.02%	96.77%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.61%	97.14%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.94%	96.90%
CHEMBL226	P30542	Adenosine A1 receptor	82.39%	95.93%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.65%	86.92%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.15%	96.61%

Plants that contains it

• Ajuga reptans

Cross-Links

• PubChem: 163029198
• LOTUS: LTS0233762
• wikiData: Q105386096