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

Details

• Internal ID: 4a8318e0-d6be-47c9-9270-ea3aa89678e3
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Bufanolides and derivatives
• IUPAC Name: 5-[(3S,8S,9R,10R,13R,14R,17S)-8,14-dihydroxy-10,13-dimethyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,6,7,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]pyran-2-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C4CCC5(C(CCC5(C4(CCC3=C2)O)O)C6=COC(=O)C=C6)C)C)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC[C@@]5([C@@H](CC[C@@]5([C@@]4(CCC3=C2)O)O)C6=COC(=O)C=C6)C)C)O)O)O
• InChI: InChI=1S/C30H42O9/c1-16-23(32)24(33)25(34)26(38-16)39-19-7-10-27(2)18(14-19)6-12-29(35)21(27)9-11-28(3)20(8-13-30(28,29)36)17-4-5-22(31)37-15-17/h4-5,14-16,19-21,23-26,32-36H,6-13H2,1-3H3/t16-,19-,20-,21+,23-,24+,25+,26-,27-,28+,29-,30+/m0/s1
• InChI Key: IOUCAHDIONSWJC-ZHUGLHFPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₂O₉
• Molecular Weight: 546.60 g/mol
• Exact Mass: 546.28288291 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 2.13
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9598	95.98%
Caco-2	-	0.9123	91.23%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7620	76.20%
OATP2B1 inhibitior	-	0.7243	72.43%
OATP1B1 inhibitior	+	0.8464	84.64%
OATP1B3 inhibitior	+	0.8356	83.56%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9321	93.21%
BSEP inhibitior	+	0.6047	60.47%
P-glycoprotein inhibitior	+	0.5864	58.64%
P-glycoprotein substrate	-	0.6519	65.19%
CYP3A4 substrate	+	0.7091	70.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8666	86.66%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.6081	60.81%
CYP inhibitory promiscuity	-	0.8738	87.38%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5173	51.73%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9427	94.27%
Skin irritation	-	0.5499	54.99%
Skin corrosion	-	0.9294	92.94%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7279	72.79%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.6049	60.49%
skin sensitisation	-	0.8631	86.31%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.7479	74.79%
Acute Oral Toxicity (c)	II	0.7732	77.32%
Estrogen receptor binding	+	0.8500	85.00%
Androgen receptor binding	+	0.7209	72.09%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7139	71.39%
Aromatase binding	+	0.7018	70.18%
PPAR gamma	+	0.5844	58.44%
Honey bee toxicity	-	0.7483	74.83%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9934	99.34%

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	95.63%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.91%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.60%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.49%	86.33%
CHEMBL2581	P07339	Cathepsin D	92.91%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.68%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.68%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.58%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.53%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.15%	93.99%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.78%	100.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.00%	97.36%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.75%	81.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.72%	99.23%
CHEMBL4208	P20618	Proteasome component C5	82.38%	90.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.38%	89.67%

Plants that contains it

• Drimia maritima

Cross-Links

• PubChem: 163046008
• LOTUS: LTS0239980
• wikiData: Q105116885