(2R,3R,4S,5S,6R)-2-[[(3S,8S,9S,10R,13S,14S,16S,17S)-16-hydroxy-17-[(1S)-1-hydroxyethyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 21b2f203-0c0a-4f8a-aaf7-737102d04dd6
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(3S,8S,9S,10R,13S,14S,16S,17S)-16-hydroxy-17-[(1S)-1-hydroxyethyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(C1C(CC2C1(CCC3C2CC=C4C3(CCC(C4)OC5C(C(C(C(O5)CO)O)O)O)C)C)O)O
• SMILES (Isomeric): C[C@@H]([C@H]1[C@H](C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)C)O)O
• InChI: InChI=1S/C27H44O8/c1-13(29)21-19(30)11-18-16-5-4-14-10-15(6-8-26(14,2)17(16)7-9-27(18,21)3)34-25-24(33)23(32)22(31)20(12-28)35-25/h4,13,15-25,28-33H,5-12H2,1-3H3/t13-,15-,16+,17-,18-,19-,20+,21-,22+,23-,24+,25+,26-,27-/m0/s1
• InChI Key: MMAFNNBLJJXUCU-PIZSPIDASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₄O₈
• Molecular Weight: 496.60 g/mol
• Exact Mass: 496.30361836 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 1.10
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8234	82.34%
Caco-2	-	0.8405	84.05%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7076	70.76%
OATP2B1 inhibitior	-	0.7207	72.07%
OATP1B1 inhibitior	+	0.9113	91.13%
OATP1B3 inhibitior	+	0.8604	86.04%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6542	65.42%
BSEP inhibitior	-	0.8193	81.93%
P-glycoprotein inhibitior	-	0.5727	57.27%
P-glycoprotein substrate	-	0.5788	57.88%
CYP3A4 substrate	+	0.7173	71.73%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.8839	88.39%
CYP2C9 inhibition	-	0.8944	89.44%
CYP2C19 inhibition	-	0.9073	90.73%
CYP2D6 inhibition	-	0.9379	93.79%
CYP1A2 inhibition	-	0.8463	84.63%
CYP2C8 inhibition	+	0.5305	53.05%
CYP inhibitory promiscuity	-	0.9050	90.50%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6914	69.14%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9591	95.91%
Skin irritation	+	0.5291	52.91%
Skin corrosion	-	0.9463	94.63%
Ames mutagenesis	-	0.8670	86.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7138	71.38%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.8533	85.33%
skin sensitisation	-	0.9238	92.38%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.9032	90.32%
Acute Oral Toxicity (c)	III	0.4201	42.01%
Estrogen receptor binding	+	0.6479	64.79%
Androgen receptor binding	+	0.6958	69.58%
Thyroid receptor binding	-	0.5329	53.29%
Glucocorticoid receptor binding	+	0.6571	65.71%
Aromatase binding	+	0.5799	57.99%
PPAR gamma	-	0.5420	54.20%
Honey bee toxicity	-	0.7478	74.78%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9322	93.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.06%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	97.92%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.02%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.97%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.50%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.61%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.59%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.30%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.18%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.52%	95.89%
CHEMBL237	P41145	Kappa opioid receptor	89.05%	98.10%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.44%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.45%	93.56%
CHEMBL2996	Q05655	Protein kinase C delta	85.35%	97.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.29%	89.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	83.62%	94.23%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.88%	89.05%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.16%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.44%	97.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.06%	95.56%

Plants that contains it

• Balanites aegyptiaca

Cross-Links

• PubChem: 162898949
• LOTUS: LTS0006667
• wikiData: Q105167418