Methyl (2R)-2-[(4aR,6aS,7R,8S,9aS,10aS,12aR)-8-hydroxy-1,1,4a,6a,10a-pentamethyl-2-oxo-2,3,4,4a,4b,5,6,6a,6b,7,8,9a,10,10a,12,12a-hexadecahydro-1H-naphtho[2',1':4,5]indeno[2,1-b]furan-7-yl]-6-methyl-5-heptenoate

Details

• Internal ID: 0a5ab519-564d-479e-86ff-19272010a18a
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives
• IUPAC Name: methyl (2R)-2-[(2S,4S,6S,7R,8S,9S,13R,18R)-6-hydroxy-2,9,13,17,17-pentamethyl-16-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-1(20)-en-7-yl]-6-methylhept-5-enoate
• SMILES (Canonical): CC(=CCCC(C1C2C(CC3(C2(CCC4C3=CCC5C4(CCC(=O)C5(C)C)C)C)C)OC1O)C(=O)OC)C
• SMILES (Isomeric): CC(=CCC[C@H]([C@H]1[C@@H]2[C@H](C[C@]3([C@]2(CCC4C3=CC[C@@H]5[C@@]4(CCC(=O)C5(C)C)C)C)C)O[C@@H]1O)C(=O)OC)C
• InChI: InChI=1S/C33H50O5/c1-19(2)10-9-11-20(28(35)37-8)26-27-23(38-29(26)36)18-33(7)22-12-13-24-30(3,4)25(34)15-16-31(24,5)21(22)14-17-32(27,33)6/h10,12,20-21,23-24,26-27,29,36H,9,11,13-18H2,1-8H3/t20-,21?,23+,24+,26+,27+,29+,31-,32+,33-/m1/s1
• InChI Key: TYLGSFWEJKPDQE-VBLNRODASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₀O₅
• Molecular Weight: 526.70 g/mol
• Exact Mass: 526.36582469 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 6.50
• Atomic LogP (AlogP): 6.64
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• Methyl (2R)-2-[(4aR,6aS,7R,8S,9aS,10aS,12aR)-8-hydroxy-1,1,4a,6a,10a-pentamethyl-2-oxo-2,3,4,4a,4b,5,6,6a,6b,7,8,9a,10,10a,12,12a-hexadecahydro-1H-naphtho[2',1':4,5]indeno[2,1-b]furan-7-yl]-6-methyl-5-heptenoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9873	98.73%
Caco-2	-	0.6325	63.25%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8259	82.59%
OATP2B1 inhibitior	-	0.7212	72.12%
OATP1B1 inhibitior	+	0.8406	84.06%
OATP1B3 inhibitior	-	0.2158	21.58%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.9780	97.80%
P-glycoprotein inhibitior	+	0.7498	74.98%
P-glycoprotein substrate	-	0.5467	54.67%
CYP3A4 substrate	+	0.7139	71.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8681	86.81%
CYP3A4 inhibition	+	0.5690	56.90%
CYP2C9 inhibition	-	0.7661	76.61%
CYP2C19 inhibition	-	0.8460	84.60%
CYP2D6 inhibition	-	0.9209	92.09%
CYP1A2 inhibition	-	0.5679	56.79%
CYP2C8 inhibition	+	0.5585	55.85%
CYP inhibitory promiscuity	-	0.7504	75.04%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6078	60.78%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9281	92.81%
Skin irritation	+	0.5058	50.58%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	-	0.5882	58.82%
Human Ether-a-go-go-Related Gene inhibition	+	0.6562	65.62%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.5428	54.28%
skin sensitisation	-	0.8029	80.29%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.6208	62.08%
Acute Oral Toxicity (c)	III	0.6993	69.93%
Estrogen receptor binding	+	0.7634	76.34%
Androgen receptor binding	+	0.7517	75.17%
Thyroid receptor binding	+	0.6216	62.16%
Glucocorticoid receptor binding	+	0.8154	81.54%
Aromatase binding	+	0.7399	73.99%
PPAR gamma	+	0.6795	67.95%
Honey bee toxicity	-	0.7410	74.10%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9947	99.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.41%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.75%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	89.88%	90.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.79%	92.62%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.65%	82.69%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.31%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.26%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.23%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.84%	91.19%
CHEMBL2581	P07339	Cathepsin D	86.15%	98.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.32%	91.07%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.24%	99.17%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	84.45%	97.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.97%	94.33%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.74%	96.38%
CHEMBL1937	Q92769	Histone deacetylase 2	83.43%	94.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.10%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.92%	95.89%
CHEMBL5028	O14672	ADAM10	82.47%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	82.43%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.40%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.64%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.60%	89.34%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	80.70%	96.00%

Plants that contains it

• Melia volkensii

Cross-Links

• PubChem: 490539
• LOTUS: LTS0160633
• wikiData: Q105267398