5-[(3S,8R,9S,10R,12S,13S,14S,17R)-12,14-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: 9c878789-5720-49bf-90b5-e23492708fec
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Bufanolides and derivatives
• IUPAC Name: 5-[(3S,8R,9S,10R,12S,13S,14S,17R)-12,14-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=C1CCC3C2CC(C4(C3(CCC4C5=COC(=O)C=C5)O)C)O)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): C[C@]12CC[C@@H](C=C1CC[C@@H]3[C@@H]2C[C@@H]([C@]4([C@@]3(CC[C@@H]4C5=COC(=O)C=C5)O)C)O)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)4-5-19-20(28)12-22(32)29(2)18(8-10-30(19,29)37)15-3-6-23(33)38-14-15/h3,6,11,14,17-22,24-27,31-32,34-37H,4-5,7-10,12-13H2,1-2H3/t17-,18+,19+,20-,21+,22-,24+,25-,26+,27+,28-,29-,30-/m0/s1
• InChI Key: XKNRCIXILGHSLP-LWDMKCRBSA-N
• Popularity: 1 reference 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: 0.20
• 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	-	0.9196	91.96%
Blood Brain Barrier	-	0.6400	64.00%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.8468	84.68%
OATP2B1 inhibitior	-	0.7241	72.41%
OATP1B1 inhibitior	+	0.8511	85.11%
OATP1B3 inhibitior	+	0.8810	88.10%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8379	83.79%
BSEP inhibitior	+	0.6805	68.05%
P-glycoprotein inhibitior	-	0.4301	43.01%
P-glycoprotein substrate	-	0.6307	63.07%
CYP3A4 substrate	+	0.7048	70.48%
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	+	0.5928	59.28%
CYP inhibitory promiscuity	-	0.8364	83.64%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6106	61.06%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9421	94.21%
Skin irritation	-	0.5949	59.49%
Skin corrosion	-	0.9426	94.26%
Ames mutagenesis	-	0.7070	70.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8418	84.18%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6397	63.97%
skin sensitisation	-	0.9052	90.52%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.7322	73.22%
Acute Oral Toxicity (c)	I	0.6567	65.67%
Estrogen receptor binding	+	0.8502	85.02%
Androgen receptor binding	+	0.7528	75.28%
Thyroid receptor binding	-	0.5756	57.56%
Glucocorticoid receptor binding	+	0.6620	66.20%
Aromatase binding	+	0.6636	66.36%
PPAR gamma	+	0.5907	59.07%
Honey bee toxicity	-	0.7390	73.90%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
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
CHEMBL3137262	O60341	LSD1/CoREST complex	97.64%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.61%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.14%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	95.44%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.31%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.07%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.50%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.14%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.21%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.26%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.47%	89.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.63%	91.24%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.29%	94.00%
CHEMBL2581	P07339	Cathepsin D	83.38%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.23%	99.23%

Plants that contains it

• Drimia maritima

Cross-Links

• PubChem: 162991352
• LOTUS: LTS0116781
• wikiData: Q105329595