(2S,3R,5R,9R,10R,13R,14R,17S)-2,3,14-trihydroxy-17-[(2R,3R)-2-hydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one

Details

• Internal ID: 443fd6f5-1044-4211-9c00-cbde7d0d0fb0
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (2S,3R,5R,9R,10R,13R,14R,17S)-2,3,14-trihydroxy-17-[(2R,3R)-2-hydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• SMILES (Canonical): CC(C)CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): CC(C)CC[C@H]([C@@](C)([C@H]1CC[C@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)C)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C33H54O11/c1-16(2)6-7-25(44-29-28(40)27(39)26(38)23(15-34)43-29)32(5,41)24-9-11-33(42)18-12-20(35)19-13-21(36)22(37)14-30(19,3)17(18)8-10-31(24,33)4/h12,16-17,19,21-29,34,36-42H,6-11,13-15H2,1-5H3/t17-,19-,21+,22-,23+,24-,25+,26+,27-,28+,29-,30+,31+,32+,33-/m0/s1
• InChI Key: UPMZPXAMHPZSQX-WIKHOFDESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₄O₁₁
• Molecular Weight: 626.80 g/mol
• Exact Mass: 626.36661253 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.56
• H-Bond Acceptor: 11
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9026	90.26%
Caco-2	-	0.7949	79.49%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8474	84.74%
OATP2B1 inhibitior	-	0.5856	58.56%
OATP1B1 inhibitior	+	0.8779	87.79%
OATP1B3 inhibitior	-	0.2724	27.24%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6568	65.68%
BSEP inhibitior	-	0.5840	58.40%
P-glycoprotein inhibitior	+	0.6209	62.09%
P-glycoprotein substrate	+	0.5118	51.18%
CYP3A4 substrate	+	0.7278	72.78%
CYP2C9 substrate	-	0.8067	80.67%
CYP2D6 substrate	-	0.8910	89.10%
CYP3A4 inhibition	-	0.8752	87.52%
CYP2C9 inhibition	-	0.8084	80.84%
CYP2C19 inhibition	-	0.9022	90.22%
CYP2D6 inhibition	-	0.9331	93.31%
CYP1A2 inhibition	-	0.8266	82.66%
CYP2C8 inhibition	+	0.4611	46.11%
CYP inhibitory promiscuity	-	0.9107	91.07%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6947	69.47%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9268	92.68%
Skin irritation	+	0.5185	51.85%
Skin corrosion	-	0.9448	94.48%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7386	73.86%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5883	58.83%
skin sensitisation	-	0.9059	90.59%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.8241	82.41%
Acute Oral Toxicity (c)	III	0.6684	66.84%
Estrogen receptor binding	+	0.6842	68.42%
Androgen receptor binding	+	0.7449	74.49%
Thyroid receptor binding	-	0.5538	55.38%
Glucocorticoid receptor binding	+	0.6063	60.63%
Aromatase binding	+	0.6421	64.21%
PPAR gamma	+	0.5945	59.45%
Honey bee toxicity	-	0.7456	74.56%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9645	96.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.49%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.41%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.29%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.39%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.23%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.70%	96.09%
CHEMBL220	P22303	Acetylcholinesterase	95.09%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.07%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.77%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.36%	97.14%
CHEMBL226	P30542	Adenosine A1 receptor	91.14%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.43%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.10%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.50%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.62%	94.45%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.63%	91.07%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.97%	86.92%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	84.88%	94.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.05%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.02%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.99%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.50%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.00%	93.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.99%	96.21%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.20%	95.71%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.89%	96.90%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	80.78%	100.00%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	80.75%	94.78%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.64%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.60%	92.62%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.10%	100.00%

Plants that contains it

• Rhaponticum carthamoides subsp. carthamoides

Cross-Links

• PubChem: 101851583
• LOTUS: LTS0025245
• wikiData: Q105276876