[(3S,6R,8S,9R,10R,13R,14R,17R)-3-[(2R,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-8,14-dihydroxy-10,13-dimethyl-17-(6-oxopyran-3-yl)-2,3,6,7,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-yl] acetate

Details

• Internal ID: e4b512c7-4975-40f1-8189-c53c0ea16dea
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Bufanolides and derivatives
• IUPAC Name: [(3S,6R,8S,9R,10R,13R,14R,17R)-3-[(2R,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-8,14-dihydroxy-10,13-dimethyl-17-(6-oxopyran-3-yl)-2,3,6,7,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C4CCC5(C(CCC5(C4(CC(C3=C2)OC(=O)C)O)O)C6=COC(=O)C=C6)C)C)O)O)OC7C(C(C(C(O7)CO)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(C[C@H](C3=C2)OC(=O)C)O)O)C6=COC(=O)C=C6)C)C)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C38H54O16/c1-17-32(54-34-30(45)28(43)27(42)24(15-39)53-34)29(44)31(46)33(50-17)52-20-7-10-35(3)22(13-20)23(51-18(2)40)14-37(47)25(35)9-11-36(4)21(8-12-38(36,37)48)19-5-6-26(41)49-16-19/h5-6,13,16-17,20-21,23-25,27-34,39,42-48H,7-12,14-15H2,1-4H3/t17-,20-,21+,23+,24+,25+,27+,28-,29-,30+,31+,32-,33-,34-,35-,36+,37-,38+/m0/s1
• InChI Key: UQLIMNOWAULTPJ-ZHDVDOAZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₅₄O₁₆
• Molecular Weight: 766.80 g/mol
• Exact Mass: 766.34118563 g/mol
• Topological Polar Surface Area (TPSA): 251.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -0.51
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9170	91.70%
Caco-2	-	0.8845	88.45%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8297	82.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7991	79.91%
OATP1B3 inhibitior	+	0.8633	86.33%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8276	82.76%
BSEP inhibitior	+	0.7919	79.19%
P-glycoprotein inhibitior	+	0.7302	73.02%
P-glycoprotein substrate	+	0.5272	52.72%
CYP3A4 substrate	+	0.7292	72.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8812	88.12%
CYP3A4 inhibition	-	0.7112	71.12%
CYP2C9 inhibition	-	0.8844	88.44%
CYP2C19 inhibition	-	0.9255	92.55%
CYP2D6 inhibition	-	0.9365	93.65%
CYP1A2 inhibition	-	0.8717	87.17%
CYP2C8 inhibition	+	0.6869	68.69%
CYP inhibitory promiscuity	-	0.8888	88.88%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5817	58.17%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9139	91.39%
Skin irritation	-	0.5531	55.31%
Skin corrosion	-	0.9409	94.09%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7201	72.01%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.6498	64.98%
skin sensitisation	-	0.9209	92.09%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7680	76.80%
Acute Oral Toxicity (c)	I	0.7810	78.10%
Estrogen receptor binding	+	0.8125	81.25%
Androgen receptor binding	+	0.7336	73.36%
Thyroid receptor binding	-	0.5279	52.79%
Glucocorticoid receptor binding	+	0.6735	67.35%
Aromatase binding	+	0.6473	64.73%
PPAR gamma	+	0.7421	74.21%
Honey bee toxicity	-	0.6803	68.03%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5250	52.50%
Fish aquatic toxicity	+	0.9905	99.05%

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	99.09%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.84%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.17%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.21%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.46%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.39%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.99%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.35%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.10%	94.00%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	86.97%	87.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.57%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.53%	97.25%
CHEMBL4208	P20618	Proteasome component C5	86.16%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.03%	97.36%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	85.20%	89.44%
CHEMBL226	P30542	Adenosine A1 receptor	84.17%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.89%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.89%	99.23%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.68%	81.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.44%	94.45%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.01%	89.67%

Plants that contains it

• Drimia maritima

Cross-Links

• PubChem: 10818959
• LOTUS: LTS0070735
• wikiData: Q105277320