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

Details

• Internal ID: 55b3718f-fc20-4c6d-9d8c-92fbacf91b9c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(5R,10R,14S)-3-[(2R,3S,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-14-hydroxy-10-(hydroxymethyl)-13-methyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)O)C)CO)O)OC)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@@H]([C@@H](O1)OC2CC[C@]3([C@@H](C2)CCC4C3CCC5([C@@]4(CCC5C6=CC(=O)OC6)O)C)CO)O)OC)O
• InChI: InChI=1S/C30H46O9/c1-16-24(33)26(36-3)25(34)27(38-16)39-19-6-10-29(15-31)18(13-19)4-5-22-21(29)7-9-28(2)20(8-11-30(22,28)35)17-12-23(32)37-14-17/h12,16,18-22,24-27,31,33-35H,4-11,13-15H2,1-3H3/t16-,18+,19?,20?,21?,22?,24-,25-,26+,27-,28?,29+,30-/m0/s1
• InChI Key: RUXOGPGQKCWGOH-BGEHYGTQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₆O₉
• Molecular Weight: 550.70 g/mol
• Exact Mass: 550.31418304 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 2.08
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9031	90.31%
Caco-2	-	0.8289	82.89%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7765	77.65%
OATP2B1 inhibitior	-	0.6059	60.59%
OATP1B1 inhibitior	+	0.9275	92.75%
OATP1B3 inhibitior	+	0.9519	95.19%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.4940	49.40%
P-glycoprotein inhibitior	-	0.4736	47.36%
P-glycoprotein substrate	+	0.7143	71.43%
CYP3A4 substrate	+	0.7081	70.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9020	90.20%
CYP3A4 inhibition	-	0.8983	89.83%
CYP2C9 inhibition	-	0.9110	91.10%
CYP2C19 inhibition	-	0.9207	92.07%
CYP2D6 inhibition	-	0.9432	94.32%
CYP1A2 inhibition	-	0.9286	92.86%
CYP2C8 inhibition	-	0.6109	61.09%
CYP inhibitory promiscuity	-	0.8822	88.22%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5625	56.25%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9464	94.64%
Skin irritation	-	0.5713	57.13%
Skin corrosion	-	0.9454	94.54%
Ames mutagenesis	-	0.6424	64.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.8023	80.23%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.9215	92.15%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.7865	78.65%
Acute Oral Toxicity (c)	I	0.8135	81.35%
Estrogen receptor binding	+	0.7733	77.33%
Androgen receptor binding	+	0.8061	80.61%
Thyroid receptor binding	-	0.6097	60.97%
Glucocorticoid receptor binding	+	0.6454	64.54%
Aromatase binding	+	0.6482	64.82%
PPAR gamma	+	0.5240	52.40%
Honey bee toxicity	-	0.6876	68.76%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.8932	89.32%

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	98.67%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.71%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.10%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.41%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.35%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.13%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.37%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.78%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.40%	82.69%
CHEMBL2581	P07339	Cathepsin D	88.09%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.68%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.55%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.42%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.13%	95.56%
CHEMBL3492	P49721	Proteasome Macropain subunit	85.20%	90.24%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.65%	85.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.62%	95.89%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	83.42%	81.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.37%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.02%	97.14%

Plants that contains it

• Aloe vera
• Artemisia annua
• Artemisia scoparia
• Crataegus pinnatifida
• Fagopyrum esculentum
• Ginkgo biloba
• Glycyrrhiza uralensis
• Gynostemma pentaphyllum
• Hippophae rhamnoides
• Houttuynia cordata
• Hypericum ascyron
• Leonurus japonicus
• Ruta graveolens
• Styphnolobium japonicum
• Typha domingensis
• Ziziphus jujuba

Cross-Links

• PubChem: 6325934
• NPASS: NPC158306