[(1R,3S,5S,8R,9S,10R,13R,14S,17R)-10-formyl-3,5,14-trihydroxy-13-methyl-17-(6-oxopyran-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-1-yl] acetate

Details

• Internal ID: c3782895-174d-485a-a5a4-2645e1cfe57b
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Bufanolides and derivatives
• IUPAC Name: [(1R,3S,5S,8R,9S,10R,13R,14S,17R)-10-formyl-3,5,14-trihydroxy-13-methyl-17-(6-oxopyran-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-1-yl] acetate
• SMILES (Canonical): CC(=O)OC1CC(CC2(C1(C3CCC4(C(CCC4(C3CC2)O)C5=COC(=O)C=C5)C)C=O)O)O
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H](C[C@@]2([C@]1([C@H]3CC[C@@]4([C@H](CC[C@@]4([C@@H]3CC2)O)C5=COC(=O)C=C5)C)C=O)O)O
• InChI: InChI=1S/C26H34O8/c1-15(28)34-21-11-17(29)12-24(31)9-6-20-19(25(21,24)14-27)5-8-23(2)18(7-10-26(20,23)32)16-3-4-22(30)33-13-16/h3-4,13-14,17-21,29,31-32H,5-12H2,1-2H3/t17-,18+,19-,20+,21+,23+,24-,25-,26-/m0/s1
• InChI Key: RKMAEUSVJAICNS-LYKPKXNDSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₄O₈
• Molecular Weight: 474.50 g/mol
• Exact Mass: 474.22536804 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 2.08
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9528	95.28%
Caco-2	-	0.7644	76.44%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7847	78.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8343	83.43%
OATP1B3 inhibitior	+	0.8947	89.47%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9358	93.58%
BSEP inhibitior	+	0.9221	92.21%
P-glycoprotein inhibitior	-	0.5795	57.95%
P-glycoprotein substrate	-	0.7206	72.06%
CYP3A4 substrate	+	0.7157	71.57%
CYP2C9 substrate	-	0.8002	80.02%
CYP2D6 substrate	-	0.8599	85.99%
CYP3A4 inhibition	-	0.5722	57.22%
CYP2C9 inhibition	-	0.8705	87.05%
CYP2C19 inhibition	-	0.9002	90.02%
CYP2D6 inhibition	-	0.9404	94.04%
CYP1A2 inhibition	-	0.7370	73.70%
CYP2C8 inhibition	+	0.5690	56.90%
CYP inhibitory promiscuity	-	0.9196	91.96%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6507	65.07%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.9627	96.27%
Skin irritation	-	0.6263	62.63%
Skin corrosion	-	0.9032	90.32%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6490	64.90%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.6301	63.01%
skin sensitisation	-	0.9230	92.30%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.4730	47.30%
Acute Oral Toxicity (c)	I	0.5617	56.17%
Estrogen receptor binding	+	0.9283	92.83%
Androgen receptor binding	+	0.7613	76.13%
Thyroid receptor binding	+	0.5134	51.34%
Glucocorticoid receptor binding	+	0.7721	77.21%
Aromatase binding	+	0.7086	70.86%
PPAR gamma	-	0.4944	49.44%
Honey bee toxicity	-	0.6389	63.89%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9889	98.89%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.39%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.13%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.12%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.19%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.36%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.02%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.76%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.17%	100.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	88.55%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.13%	95.89%
CHEMBL4208	P20618	Proteasome component C5	85.84%	90.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.74%	93.04%
CHEMBL340	P08684	Cytochrome P450 3A4	84.33%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.42%	99.23%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.17%	82.69%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.39%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.41%	97.14%

Plants that contains it

• Fritillaria pallidiflora
• Kalanchoe daigremontiana
• Koelreuteria paniculata

Cross-Links

• PubChem: 21768174
• NPASS: NPC255180
• LOTUS: LTS0252313
• wikiData: Q105238506