5-[(3S,8R,9S,10R,13R,14S,16S,17R)-14,16-dihydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one

Details

• Internal ID: a3ac74f0-9e5f-484a-ba14-6555ada7f987
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Bufanolides and derivatives
• IUPAC Name: 5-[(3S,8R,9S,10R,13R,14S,16S,17R)-14,16-dihydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
• SMILES (Canonical): CC12CCC(C=C1CCC3C2CCC4(C3(CC(C4C5=COC(=O)C=C5)O)O)C)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): C[C@]12CC[C@@H](C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@@]3(C[C@@H]([C@@H]4C5=COC(=O)C=C5)O)O)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C30H42O10/c1-28-9-7-17(39-27-26(36)25(35)24(34)21(13-31)40-27)11-16(28)4-5-19-18(28)8-10-29(2)23(20(32)12-30(19,29)37)15-3-6-22(33)38-14-15/h3,6,11,14,17-21,23-27,31-32,34-37H,4-5,7-10,12-13H2,1-2H3/t17-,18-,19+,20-,21+,23-,24+,25-,26+,27+,28-,29+,30-/m0/s1
• InChI Key: LSMWWMPPULJBQX-NEDFIKGHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₂O₁₀
• Molecular Weight: 562.60 g/mol
• Exact Mass: 562.27779753 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.96
• 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	+	0.9321	93.21%
Caco-2	-	0.9181	91.81%
Blood Brain Barrier	-	0.6400	64.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8468	84.68%
OATP2B1 inhibitior	-	0.7257	72.57%
OATP1B1 inhibitior	+	0.8329	83.29%
OATP1B3 inhibitior	+	0.8810	88.10%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8379	83.79%
BSEP inhibitior	+	0.7191	71.91%
P-glycoprotein inhibitior	-	0.4419	44.19%
P-glycoprotein substrate	-	0.6505	65.05%
CYP3A4 substrate	+	0.7218	72.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8668	86.68%
CYP3A4 inhibition	-	0.8299	82.99%
CYP2C9 inhibition	-	0.9001	90.01%
CYP2C19 inhibition	-	0.9056	90.56%
CYP2D6 inhibition	-	0.9008	90.08%
CYP1A2 inhibition	-	0.8479	84.79%
CYP2C8 inhibition	+	0.6763	67.63%
CYP inhibitory promiscuity	-	0.8364	83.64%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6106	61.06%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9429	94.29%
Skin irritation	-	0.5949	59.49%
Skin corrosion	-	0.9426	94.26%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8421	84.21%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6878	68.78%
skin sensitisation	-	0.9052	90.52%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.7575	75.75%
Acute Oral Toxicity (c)	I	0.6567	65.67%
Estrogen receptor binding	+	0.8593	85.93%
Androgen receptor binding	+	0.7666	76.66%
Thyroid receptor binding	-	0.5585	55.85%
Glucocorticoid receptor binding	+	0.6930	69.30%
Aromatase binding	+	0.6846	68.46%
PPAR gamma	+	0.5926	59.26%
Honey bee toxicity	-	0.7020	70.20%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9872	98.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.21%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.43%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.81%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.83%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.79%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.01%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.43%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.79%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.41%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.17%	85.14%
CHEMBL220	P22303	Acetylcholinesterase	89.05%	94.45%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.30%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.37%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.37%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	83.45%	95.93%

Plants that contains it

• Drimia maritima

Cross-Links

• PubChem: 101985986
• LOTUS: LTS0055176
• wikiData: Q105156645