(2R,3R,4S,5S,6R)-2-[(2S)-2-[(2S,4aR,4bS,7S,8S,8aS)-7-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-3,4,4a,5,6,7,8a,9-octahydro-1H-phenanthren-2-yl]-2-hydroxyethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 77cc4ac8-185f-45a2-8bf9-f0ae0f9bc7c2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(2S)-2-[(2S,4aR,4bS,7S,8S,8aS)-7-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-3,4,4a,5,6,7,8a,9-octahydro-1H-phenanthren-2-yl]-2-hydroxyethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1(CCC2C(=CCC3C2(CCC(C3(C)CO)O)C)C1)C(COC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): C[C@@]1(CC[C@@H]2C(=CC[C@H]3[C@]2(CC[C@@H]([C@]3(C)CO)O)C)C1)[C@@H](CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C26H44O9/c1-24(19(30)12-34-23-22(33)21(32)20(31)16(11-27)35-23)8-6-15-14(10-24)4-5-17-25(15,2)9-7-18(29)26(17,3)13-28/h4,15-23,27-33H,5-13H2,1-3H3/t15-,16-,17+,18+,19-,20-,21+,22-,23-,24+,25+,26-/m1/s1
• InChI Key: UTXLOPQCWLMVMN-UJQKAVTMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₄O₉
• Molecular Weight: 500.60 g/mol
• Exact Mass: 500.29853298 g/mol
• Topological Polar Surface Area (TPSA): 160.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.08
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6995	69.95%
Caco-2	-	0.8049	80.49%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7301	73.01%
OATP2B1 inhibitior	-	0.5819	58.19%
OATP1B1 inhibitior	+	0.8849	88.49%
OATP1B3 inhibitior	-	0.2812	28.12%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.7838	78.38%
P-glycoprotein inhibitior	-	0.5974	59.74%
P-glycoprotein substrate	-	0.7048	70.48%
CYP3A4 substrate	+	0.6726	67.26%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.8956	89.56%
CYP2C9 inhibition	-	0.9100	91.00%
CYP2C19 inhibition	-	0.8740	87.40%
CYP2D6 inhibition	-	0.9403	94.03%
CYP1A2 inhibition	-	0.8475	84.75%
CYP2C8 inhibition	-	0.6049	60.49%
CYP inhibitory promiscuity	-	0.9490	94.90%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6894	68.94%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9521	95.21%
Skin irritation	-	0.6067	60.67%
Skin corrosion	-	0.9507	95.07%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7340	73.40%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.7226	72.26%
skin sensitisation	-	0.9097	90.97%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.6041	60.41%
Acute Oral Toxicity (c)	III	0.6489	64.89%
Estrogen receptor binding	+	0.5642	56.42%
Androgen receptor binding	+	0.6926	69.26%
Thyroid receptor binding	+	0.5539	55.39%
Glucocorticoid receptor binding	+	0.5938	59.38%
Aromatase binding	+	0.6122	61.22%
PPAR gamma	-	0.5479	54.79%
Honey bee toxicity	-	0.7091	70.91%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6950	69.50%
Fish aquatic toxicity	+	0.9053	90.53%

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	97.75%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.41%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.94%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.16%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.52%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.15%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.48%	97.36%
CHEMBL2581	P07339	Cathepsin D	87.67%	98.95%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	86.73%	94.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.46%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	86.06%	90.17%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.44%	96.61%
CHEMBL1937	Q92769	Histone deacetylase 2	84.34%	94.75%
CHEMBL226	P30542	Adenosine A1 receptor	83.56%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.61%	89.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.32%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.85%	92.62%
CHEMBL2360	P00492	Hypoxanthine-guanine phosphoribosyltransferase	81.00%	87.38%
CHEMBL4581	P52732	Kinesin-like protein 1	81.00%	93.18%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.75%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.05%	86.33%

Plants that contains it

• Palafoxia arida

Cross-Links

• PubChem: 163075807
• LOTUS: LTS0161159
• wikiData: Q105279164