3beta-[[(2S,3R,5R)-3-Hydroxy-3-(methoxycarbonyl)-5-methyltetrahydrofuran-2-yl]oxy]-2alpha,14-dihydroxy-10-hydroperoxy-19-nor-5alpha-carda-20(22)-enolide

Details

• Internal ID: 83092cfd-9d83-4579-bf0a-6b55874780d8
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones
• IUPAC Name: methyl (2S,3R,5R)-2-[[(2R,3R,5S,8R,9S,10R,13R,14S,17R)-10-hydroperoxy-2,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-3-hydroxy-5-methyloxolane-3-carboxylate
• SMILES (Canonical): CC1CC(C(O1)OC2CC3CCC4C(C3(CC2O)OO)CCC5(C4(CCC5C6=CC(=O)OC6)O)C)(C(=O)OC)O
• SMILES (Isomeric): C[C@@H]1C[C@@]([C@@H](O1)O[C@@H]2C[C@@H]3CC[C@@H]4[C@@H]([C@]3(C[C@H]2O)OO)CC[C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)(C(=O)OC)O
• InChI: InChI=1S/C29H42O11/c1-15-12-27(33,24(32)36-3)25(38-15)39-22-11-17-4-5-20-19(28(17,40-35)13-21(22)30)6-8-26(2)18(7-9-29(20,26)34)16-10-23(31)37-14-16/h10,15,17-22,25,30,33-35H,4-9,11-14H2,1-3H3/t15-,17+,18-,19+,20-,21-,22-,25+,26-,27+,28-,29+/m1/s1
• InChI Key: NTWQXIKROQBTKK-WZYSMWLRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₂O₁₁
• Molecular Weight: 566.60 g/mol
• Exact Mass: 566.27271215 g/mol
• Topological Polar Surface Area (TPSA): 161.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.86
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9799	97.99%
Caco-2	-	0.8153	81.53%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7939	79.39%
OATP2B1 inhibitior	-	0.7179	71.79%
OATP1B1 inhibitior	+	0.8697	86.97%
OATP1B3 inhibitior	+	0.9620	96.20%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8614	86.14%
BSEP inhibitior	+	0.6705	67.05%
P-glycoprotein inhibitior	+	0.6310	63.10%
P-glycoprotein substrate	+	0.7770	77.70%
CYP3A4 substrate	+	0.7356	73.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9010	90.10%
CYP3A4 inhibition	-	0.7728	77.28%
CYP2C9 inhibition	-	0.8082	80.82%
CYP2C19 inhibition	-	0.8855	88.55%
CYP2D6 inhibition	-	0.9410	94.10%
CYP1A2 inhibition	-	0.8553	85.53%
CYP2C8 inhibition	+	0.5464	54.64%
CYP inhibitory promiscuity	-	0.9083	90.83%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4229	42.29%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.9414	94.14%
Skin irritation	-	0.5812	58.12%
Skin corrosion	-	0.9220	92.20%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6965	69.65%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.7018	70.18%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.5942	59.42%
Acute Oral Toxicity (c)	I	0.5832	58.32%
Estrogen receptor binding	+	0.7261	72.61%
Androgen receptor binding	+	0.8184	81.84%
Thyroid receptor binding	-	0.5731	57.31%
Glucocorticoid receptor binding	+	0.7250	72.50%
Aromatase binding	+	0.7374	73.74%
PPAR gamma	+	0.5766	57.66%
Honey bee toxicity	-	0.7130	71.30%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9851	98.51%

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	98.15%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.08%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.32%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.96%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.76%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.31%	82.69%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.78%	92.94%
CHEMBL204	P00734	Thrombin	90.61%	96.01%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.53%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.02%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.62%	97.09%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	87.33%	81.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.03%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	83.55%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.28%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	82.16%	92.50%
CHEMBL4208	P20618	Proteasome component C5	81.18%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.90%	95.56%
CHEMBL2581	P07339	Cathepsin D	80.89%	98.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.88%	94.33%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.28%	93.04%

Plants that contains it

• Anemone narcissiflora
• Asclepias curassavica
• Hyperbaena columbica
• Viburnum lantanoides

Cross-Links

• PubChem: 101376173
• NPASS: NPC294041
• LOTUS: LTS0207755
• wikiData: Q105185713