(3R,4S,5S,6R)-2-[[(1R,3aS,4S,5Z,9S,10E,12aS)-4-hydroxy-6-(hydroxymethyl)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-2,3,4,7,8,9,12,12a-octahydro-1H-cyclopenta[11]annulen-9-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: f338e745-87bd-4e72-a204-a7f9a84797bf
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: (3R,4S,5S,6R)-2-[[(1R,3aS,4S,5Z,9S,10E,12aS)-4-hydroxy-6-(hydroxymethyl)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-2,3,4,7,8,9,12,12a-octahydro-1H-cyclopenta[11]annulen-9-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1=CCC2C(CCC2(C(C=C(CCC1COC3C(C(C(C(O3)CO)O)O)O)CO)O)C)C(C)(C)O
• SMILES (Isomeric): C/C/1=C\C[C@H]2[C@@H](CC[C@@]2([C@H](/C=C(/CC[C@@H]1COC3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)\CO)O)C)C(C)(C)O
• InChI: InChI=1S/C27H46O9/c1-15-5-8-19-18(26(2,3)34)9-10-27(19,4)21(30)11-16(12-28)6-7-17(15)14-35-25-24(33)23(32)22(31)20(13-29)36-25/h5,11,17-25,28-34H,6-10,12-14H2,1-4H3/b15-5+,16-11-/t17-,18-,19+,20-,21+,22-,23+,24-,25?,27+/m1/s1
• InChI Key: AQNPUNCGNBFMBN-PYTOJNKKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₆O₉
• Molecular Weight: 514.60 g/mol
• Exact Mass: 514.31418304 g/mol
• Topological Polar Surface Area (TPSA): 160.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): 0.63
• 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	+	0.6716	67.16%
Caco-2	-	0.8141	81.41%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7743	77.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8687	86.87%
OATP1B3 inhibitior	+	0.8484	84.84%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.6075	60.75%
P-glycoprotein inhibitior	-	0.5945	59.45%
P-glycoprotein substrate	-	0.6956	69.56%
CYP3A4 substrate	+	0.7017	70.17%
CYP2C9 substrate	-	0.7890	78.90%
CYP2D6 substrate	-	0.8406	84.06%
CYP3A4 inhibition	-	0.9460	94.60%
CYP2C9 inhibition	-	0.7883	78.83%
CYP2C19 inhibition	-	0.8428	84.28%
CYP2D6 inhibition	-	0.9364	93.64%
CYP1A2 inhibition	-	0.7921	79.21%
CYP2C8 inhibition	+	0.5456	54.56%
CYP inhibitory promiscuity	-	0.8958	89.58%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6853	68.53%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9542	95.42%
Skin irritation	-	0.6701	67.01%
Skin corrosion	-	0.9514	95.14%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8025	80.25%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.7239	72.39%
skin sensitisation	-	0.8840	88.40%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.8888	88.88%
Acute Oral Toxicity (c)	III	0.5346	53.46%
Estrogen receptor binding	+	0.6867	68.67%
Androgen receptor binding	+	0.6310	63.10%
Thyroid receptor binding	+	0.5429	54.29%
Glucocorticoid receptor binding	+	0.6077	60.77%
Aromatase binding	+	0.6252	62.52%
PPAR gamma	-	0.5096	50.96%
Honey bee toxicity	-	0.8151	81.51%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9128	91.28%

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	98.53%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.72%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	95.23%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.83%	97.09%
CHEMBL220	P22303	Acetylcholinesterase	91.85%	94.45%
CHEMBL1871	P10275	Androgen Receptor	91.11%	96.43%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.98%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.32%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	89.76%	94.73%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	89.33%	89.05%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.78%	94.00%
CHEMBL2996	Q05655	Protein kinase C delta	88.59%	97.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.34%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.64%	100.00%
CHEMBL4581	P52732	Kinesin-like protein 1	84.04%	93.18%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.76%	93.04%
CHEMBL1977	P11473	Vitamin D receptor	82.79%	99.43%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.29%	97.14%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.19%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.75%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.61%	86.33%

Plants that contains it

• Chrozophora plicata

Cross-Links

• PubChem: 162817254
• LOTUS: LTS0257884
• wikiData: Q104916961