(1R,4E,8E,12E,16R)-1-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,9,13,17-tetramethyloctadeca-4,8,12-triene-1,16,17-triol

Details

• Internal ID: ba978d84-5ee9-4776-82f5-a0a4f3734997
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1R,4E,8E,12E,16R)-1-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,9,13,17-tetramethyloctadeca-4,8,12-triene-1,16,17-triol
• SMILES (Canonical): CC(=CCCC=C(C)CCC(C1(CCC(O1)C(C)(C)O)C)O)CCC=C(C)CCC(C(C)(C)O)O
• SMILES (Isomeric): C/C(=C\CC/C=C(\C)/CC[C@H]([C@@]1(CC[C@@H](O1)C(C)(C)O)C)O)/CC/C=C(\C)/CC[C@H](C(C)(C)O)O
• InChI: InChI=1S/C30H54O5/c1-22(14-11-15-24(3)16-18-25(31)28(4,5)33)12-9-10-13-23(2)17-19-26(32)30(8)21-20-27(35-30)29(6,7)34/h12-13,15,25-27,31-34H,9-11,14,16-21H2,1-8H3/b22-12+,23-13+,24-15+/t25-,26-,27-,30+/m1/s1
• InChI Key: TWLPOABITNDBEQ-LQPRBJADSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₅₄O₅
• Molecular Weight: 494.70 g/mol
• Exact Mass: 494.39712482 g/mol
• Topological Polar Surface Area (TPSA): 90.20 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 6.15
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9490	94.90%
Caco-2	-	0.7152	71.52%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5417	54.17%
OATP2B1 inhibitior	-	0.7143	71.43%
OATP1B1 inhibitior	+	0.8997	89.97%
OATP1B3 inhibitior	+	0.9533	95.33%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.8625	86.25%
P-glycoprotein inhibitior	-	0.4520	45.20%
P-glycoprotein substrate	-	0.6768	67.68%
CYP3A4 substrate	+	0.6448	64.48%
CYP2C9 substrate	-	0.8005	80.05%
CYP2D6 substrate	-	0.7637	76.37%
CYP3A4 inhibition	-	0.7737	77.37%
CYP2C9 inhibition	-	0.7227	72.27%
CYP2C19 inhibition	-	0.6802	68.02%
CYP2D6 inhibition	-	0.9126	91.26%
CYP1A2 inhibition	-	0.7211	72.11%
CYP2C8 inhibition	-	0.7868	78.68%
CYP inhibitory promiscuity	-	0.8225	82.25%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8200	82.00%
Carcinogenicity (trinary)	Non-required	0.6278	62.78%
Eye corrosion	-	0.9712	97.12%
Eye irritation	-	0.9343	93.43%
Skin irritation	-	0.5915	59.15%
Skin corrosion	-	0.9485	94.85%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5830	58.30%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.5351	53.51%
skin sensitisation	-	0.5563	55.63%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	-	0.5333	53.33%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.5864	58.64%
Acute Oral Toxicity (c)	III	0.6078	60.78%
Estrogen receptor binding	+	0.7025	70.25%
Androgen receptor binding	-	0.6370	63.70%
Thyroid receptor binding	+	0.6436	64.36%
Glucocorticoid receptor binding	+	0.6513	65.13%
Aromatase binding	+	0.7269	72.69%
PPAR gamma	+	0.6471	64.71%
Honey bee toxicity	-	0.6472	64.72%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9019	90.19%

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	98.70%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.38%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.69%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.55%	96.61%
CHEMBL2581	P07339	Cathepsin D	89.99%	98.95%
CHEMBL2094135	Q96BI3	Gamma-secretase	88.52%	98.05%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.47%	94.45%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.46%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	86.97%	94.73%
CHEMBL233	P35372	Mu opioid receptor	86.23%	97.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.92%	97.09%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.87%	95.50%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	84.64%	92.88%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.88%	93.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.59%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.26%	96.77%
CHEMBL284	P27487	Dipeptidyl peptidase IV	82.76%	95.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.73%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.59%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.53%	93.04%
CHEMBL340	P08684	Cytochrome P450 3A4	81.68%	91.19%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	81.65%	92.78%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.32%	95.71%

Plants that contains it

• Bergia capensis
• Tabernaemontana calcarea

Cross-Links

• PubChem: 24801427
• LOTUS: LTS0065726
• wikiData: Q104994709