[(2R,3R,4S,5S,6R)-2-[[(1S,2R,3R,5S,8R,9S,10R,13R,14R,17S)-17-[(2R)-2,5-dihydroxy-6-methylhept-6-en-2-yl]-1,2-dihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] acetate

Details

• Internal ID: a9a5c49c-86b0-4adf-8280-471b289618ee
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(2R,3R,4S,5S,6R)-2-[[(1S,2R,3R,5S,8R,9S,10R,13R,14R,17S)-17-[(2R)-2,5-dihydroxy-6-methylhept-6-en-2-yl]-1,2-dihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] acetate
• SMILES (Canonical): CC(=C)C(CCC(C)(C1CCC2(C1CCC3C2(CCC4C3(C(C(C(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC(=O)C)O)O)C)C)C)O)O
• SMILES (Isomeric): CC(=C)C(CC[C@](C)([C@H]1CC[C@@]2([C@@H]1CC[C@H]3[C@]2(CC[C@@H]4[C@@]3([C@@H]([C@H]([C@@H](C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)OC(=O)C)O)O)C)C)C)O)O
• InChI: InChI=1S/C38H64O11/c1-19(2)23(41)13-17-37(8,46)22-12-15-35(6)21(22)10-11-26-36(35,7)16-14-25-34(4,5)32(29(44)31(45)38(25,26)9)49-33-30(47-20(3)40)28(43)27(42)24(18-39)48-33/h21-33,39,41-46H,1,10-18H2,2-9H3/t21-,22+,23?,24-,25+,26+,27-,28+,29-,30-,31-,32+,33+,35-,36-,37-,38+/m1/s1
• InChI Key: UESHZOAAHHTDCV-ZBZQTYFVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₆₄O₁₁
• Molecular Weight: 696.90 g/mol
• Exact Mass: 696.44486285 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 2.84
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8577	85.77%
Caco-2	-	0.8717	87.17%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7863	78.63%
OATP2B1 inhibitior	-	0.8650	86.50%
OATP1B1 inhibitior	+	0.8147	81.47%
OATP1B3 inhibitior	+	0.8061	80.61%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7318	73.18%
BSEP inhibitior	-	0.6895	68.95%
P-glycoprotein inhibitior	+	0.7782	77.82%
P-glycoprotein substrate	-	0.5367	53.67%
CYP3A4 substrate	+	0.7216	72.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8887	88.87%
CYP3A4 inhibition	-	0.8229	82.29%
CYP2C9 inhibition	-	0.7418	74.18%
CYP2C19 inhibition	-	0.8450	84.50%
CYP2D6 inhibition	-	0.9353	93.53%
CYP1A2 inhibition	-	0.7982	79.82%
CYP2C8 inhibition	+	0.5701	57.01%
CYP inhibitory promiscuity	-	0.9145	91.45%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7335	73.35%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9113	91.13%
Skin irritation	+	0.5221	52.21%
Skin corrosion	-	0.9427	94.27%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7091	70.91%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.6399	63.99%
skin sensitisation	-	0.8895	88.95%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7345	73.45%
Acute Oral Toxicity (c)	III	0.5059	50.59%
Estrogen receptor binding	+	0.6297	62.97%
Androgen receptor binding	+	0.7484	74.84%
Thyroid receptor binding	-	0.5896	58.96%
Glucocorticoid receptor binding	+	0.6305	63.05%
Aromatase binding	+	0.6749	67.49%
PPAR gamma	+	0.7039	70.39%
Honey bee toxicity	-	0.6305	63.05%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9799	97.99%

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	99.32%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.03%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.74%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.52%	94.45%
CHEMBL2581	P07339	Cathepsin D	96.49%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.12%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.00%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.70%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.57%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.20%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	89.15%	100.00%
CHEMBL2996	Q05655	Protein kinase C delta	87.98%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.80%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.08%	97.14%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.95%	91.24%
CHEMBL340	P08684	Cytochrome P450 3A4	84.19%	91.19%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.59%	93.04%
CHEMBL3401	O75469	Pregnane X receptor	83.47%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.38%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.90%	93.56%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.64%	95.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.50%	94.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.80%	82.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.65%	99.17%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.12%	85.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.01%	100.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.59%	89.50%
CHEMBL5255	O00206	Toll-like receptor 4	80.58%	92.50%

Plants that contains it

• Rhoiptelea chiliantha

Cross-Links

• PubChem: 10676175
• LOTUS: LTS0113041
• wikiData: Q105271118