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

Details

• Internal ID: f8ec3c4d-95ac-4e6c-84f0-87c48511f43f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5S,8R,9S,10R,13R,14S,17R)-5,14-dihydroxy-3-[(2R,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C4CCC5(C(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)C)OC)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@@H](C[C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC[C@@]5([C@H](CC[C@@]5([C@@H]4CC[C@@]3(C2)O)O)C6=CC(=O)OC6)C)C)OC)O
• InChI: InChI=1S/C30H46O8/c1-17-26(32)23(35-4)14-25(37-17)38-19-5-9-27(2)21-6-10-28(3)20(18-13-24(31)36-16-18)8-12-30(28,34)22(21)7-11-29(27,33)15-19/h13,17,19-23,25-26,32-34H,5-12,14-16H2,1-4H3/t17-,19+,20-,21+,22-,23-,25+,26+,27-,28-,29+,30+/m1/s1
• InChI Key: XRWQBDJPMXRDOQ-IGLPKLRXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₆O₈
• Molecular Weight: 534.70 g/mol
• Exact Mass: 534.31926842 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 3.25
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9798	97.98%
Caco-2	-	0.7837	78.37%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8327	83.27%
OATP2B1 inhibitior	-	0.5884	58.84%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9669	96.69%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7347	73.47%
P-glycoprotein inhibitior	+	0.5849	58.49%
P-glycoprotein substrate	+	0.7456	74.56%
CYP3A4 substrate	+	0.6938	69.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9037	90.37%
CYP3A4 inhibition	-	0.8680	86.80%
CYP2C9 inhibition	-	0.9034	90.34%
CYP2C19 inhibition	-	0.9307	93.07%
CYP2D6 inhibition	-	0.9449	94.49%
CYP1A2 inhibition	-	0.8908	89.08%
CYP2C8 inhibition	-	0.7410	74.10%
CYP inhibitory promiscuity	-	0.9083	90.83%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4946	49.46%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9348	93.48%
Skin irritation	+	0.4908	49.08%
Skin corrosion	-	0.9426	94.26%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7188	71.88%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.7768	77.68%
skin sensitisation	-	0.9088	90.88%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.8510	85.10%
Acute Oral Toxicity (c)	I	0.7754	77.54%
Estrogen receptor binding	+	0.7418	74.18%
Androgen receptor binding	+	0.8141	81.41%
Thyroid receptor binding	-	0.5754	57.54%
Glucocorticoid receptor binding	+	0.7171	71.71%
Aromatase binding	+	0.6925	69.25%
PPAR gamma	+	0.5253	52.53%
Honey bee toxicity	-	0.7011	70.11%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9566	95.66%

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	97.78%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.62%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.40%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.00%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.53%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.13%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.70%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.20%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.30%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.92%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	89.70%	95.93%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.03%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.04%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.94%	97.14%
CHEMBL1871	P10275	Androgen Receptor	85.62%	96.43%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.35%	82.69%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.31%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.08%	99.23%
CHEMBL4208	P20618	Proteasome component C5	83.02%	90.00%
CHEMBL2581	P07339	Cathepsin D	80.78%	98.95%

Plants that contains it

• Aconitum brevicalcaratum
• Ammodendron conollyi
• Cirsium dipsacolepis
• Cocculus diversifolius
• Crinum kirkii
• Cytisus scoparius
• Heliomeris longifolia var. annua
• Hypericum triquetrifolium
• Isodon japonicus
• Knightia deplanchei
• Mallotus rhamnifolius
• Malva sylvestris
• Mesembryanthemum emarcidum
• Nerium oleander
• Plantago lanceolata
• Ptilidium ciliare
• Scutellaria seleriana
• Solanum pimpinellifolium
• Teucrium pestalozzae
• Trichotosia subsessilis
• Trifolium apertum
• Tripodanthus acutifolius
• Veronica pectinata

Cross-Links

• PubChem: 11800467
• NPASS: NPC139929
• LOTUS: LTS0006037
• wikiData: Q105340845