Muristerone a

Details

• Internal ID: 5667d171-56ea-42dc-9c3e-1c9850657fe5
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives
• IUPAC Name: (2S,3R,5S,9R,10R,11R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3,5,11,14-pentahydroxy-10,13-dimethyl-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
• SMILES (Canonical): CC(C)CCC(C(C)(C1CCC2(C1(CC(C3C2=CC(=O)C4(C3(CC(C(C4)O)O)C)O)O)C)O)O)O
• SMILES (Isomeric): CC(C)CC[C@H]([C@@](C)([C@H]1CC[C@@]2([C@@]1(C[C@H]([C@H]3C2=CC(=O)[C@]4([C@@]3(C[C@@H]([C@@H](C4)O)O)C)O)O)C)O)O)O
• InChI: InChI=1S/C27H44O8/c1-14(2)6-7-20(31)25(5,33)19-8-9-26(34)15-10-21(32)27(35)13-17(29)16(28)11-24(27,4)22(15)18(30)12-23(19,26)3/h10,14,16-20,22,28-31,33-35H,6-9,11-13H2,1-5H3/t16-,17+,18+,19-,20+,22+,23+,24+,25+,26+,27+/m0/s1
• InChI Key: LRJUYAVTHIEHAI-LHBNDURVSA-N
• Popularity: 61 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₄O₈
• Molecular Weight: 496.60 g/mol
• Exact Mass: 496.30361836 g/mol
• Topological Polar Surface Area (TPSA): 159.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.82
• H-Bond Acceptor: 8
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

• 38778-30-2
• (2S,3R,5S,9R,10R,11R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3,5,11,14-pentahydroxy-10,13-dimethyl-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
• Muristerone
• C27H44O8
• 2beta,3beta,5beta,11alpha,14alpha,20R,22R-Heptahydro xycholest-7-en-6-one
• CHEMBL2087139
• SCHEMBL19419608
• DTXSID40959583
• BDBM50488539
• HB3985
• MFCD00056450
• AKOS024457813
• HY-103273
• CS-0026791
• 2,3,5,11,14,20,22-heptahydroxycholest-7-en-6-one
• 5b,7-Cholestene-2b,3b,5a,11a,14,20,22-heptol-6-one
• 2beta,3beta,5beta,11alpha,14alpha,20R,22R-Heptahydroxycholest-7-en-6-one
• (2?,3?,5?,11?,22R)-2,3,5,11,14,20,22-Heptahydroxycholest-7-en-6-one
• (2S,3R,5S,9R,10R,11R,13R,14S,17S)-17-((2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl)-2,3,5,11,14-pentahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6(10H)-one
• Cholest-7-en-6-one, 2,3,5,11,14,20,22-heptahydroxy-, (2beta,3beta,5beta,11alpha,22R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9876	98.76%
Caco-2	-	0.5698	56.98%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7639	76.39%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.9222	92.22%
OATP1B3 inhibitior	+	0.8829	88.29%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.4816	48.16%
P-glycoprotein inhibitior	-	0.6591	65.91%
P-glycoprotein substrate	+	0.5387	53.87%
CYP3A4 substrate	+	0.6823	68.23%
CYP2C9 substrate	-	0.8060	80.60%
CYP2D6 substrate	-	0.8847	88.47%
CYP3A4 inhibition	-	0.8669	86.69%
CYP2C9 inhibition	-	0.8366	83.66%
CYP2C19 inhibition	-	0.7655	76.55%
CYP2D6 inhibition	-	0.9506	95.06%
CYP1A2 inhibition	-	0.9041	90.41%
CYP2C8 inhibition	-	0.7916	79.16%
CYP inhibitory promiscuity	-	0.8821	88.21%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6704	67.04%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.9370	93.70%
Skin irritation	+	0.6255	62.55%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7533	75.33%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.5256	52.56%
skin sensitisation	-	0.7756	77.56%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.8534	85.34%
Acute Oral Toxicity (c)	I	0.5472	54.72%
Estrogen receptor binding	+	0.7798	77.98%
Androgen receptor binding	+	0.7450	74.50%
Thyroid receptor binding	+	0.5885	58.85%
Glucocorticoid receptor binding	+	0.7470	74.70%
Aromatase binding	+	0.6500	65.00%
PPAR gamma	-	0.5744	57.44%
Honey bee toxicity	-	0.8593	85.93%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9906	99.06%

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	99.29%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.73%	97.25%
CHEMBL2581	P07339	Cathepsin D	98.65%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.34%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.47%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.89%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.82%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.36%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.38%	97.14%
CHEMBL1937	Q92769	Histone deacetylase 2	87.31%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.66%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.28%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.85%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.78%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.77%	82.69%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.45%	93.56%
CHEMBL2179	P04062	Beta-glucocerebrosidase	82.35%	85.31%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	82.14%	94.78%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	82.05%	98.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.86%	93.99%
CHEMBL226	P30542	Adenosine A1 receptor	81.33%	95.93%
CHEMBL221	P23219	Cyclooxygenase-1	81.02%	90.17%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.01%	90.24%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.14%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.07%	95.89%

Plants that contains it

• Gomphrena globosa

Cross-Links

• PubChem: 122217
• LOTUS: LTS0065495
• wikiData: Q72493312