[(3R,4R,4aR,5S,6R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5,6,10-trihydroxy-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-4-(2-methylpropanoyloxy)-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-3-yl] (2Z)-3,7-dimethylocta-2,6-dienoate

Details

• Internal ID: 27084b55-2006-4500-b79c-743eb297fe22
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(3R,4R,4aR,5S,6R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5,6,10-trihydroxy-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-4-(2-methylpropanoyloxy)-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-3-yl] (2Z)-3,7-dimethylocta-2,6-dienoate
• SMILES (Canonical): CC(C)C(=O)OC1C(C(CC2C1(C(C(C3(C2=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C)O)O)CO)(C)C)OC(=O)C=C(C)CCC=C(C)C
• SMILES (Isomeric): CC(C)C(=O)O[C@H]1[C@@H](C(C[C@@H]2[C@]1([C@@H]([C@@H]([C@@]3(C2=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)C)O)O)CO)(C)C)OC(=O)/C=C(/C)\CCC=C(C)C
• InChI: InChI=1S/C44H70O8/c1-25(2)14-13-15-27(5)22-33(47)51-36-37(52-38(50)26(3)4)44(24-45)29(23-39(36,6)7)28-16-17-31-41(10)20-19-32(46)40(8,9)30(41)18-21-42(31,11)43(28,12)34(48)35(44)49/h14,16,22,26,29-32,34-37,45-46,48-49H,13,15,17-21,23-24H2,1-12H3/b27-22-/t29-,30-,31+,32-,34-,35+,36-,37-,41-,42+,43-,44-/m0/s1
• InChI Key: ROGMOVZUSCCKTE-AHSRYKPQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₇₀O₈
• Molecular Weight: 727.00 g/mol
• Exact Mass: 726.50706919 g/mol
• Topological Polar Surface Area (TPSA): 134.00 Ų
• XlogP: 9.20
• Atomic LogP (AlogP): 7.48
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9579	95.79%
Caco-2	-	0.8438	84.38%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8995	89.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8332	83.32%
OATP1B3 inhibitior	-	0.5316	53.16%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5818	58.18%
BSEP inhibitior	+	0.9685	96.85%
P-glycoprotein inhibitior	+	0.7947	79.47%
P-glycoprotein substrate	+	0.5591	55.91%
CYP3A4 substrate	+	0.7274	72.74%
CYP2C9 substrate	-	0.7952	79.52%
CYP2D6 substrate	-	0.8992	89.92%
CYP3A4 inhibition	-	0.7984	79.84%
CYP2C9 inhibition	-	0.7601	76.01%
CYP2C19 inhibition	-	0.8999	89.99%
CYP2D6 inhibition	-	0.9433	94.33%
CYP1A2 inhibition	-	0.8745	87.45%
CYP2C8 inhibition	+	0.6196	61.96%
CYP inhibitory promiscuity	-	0.9441	94.41%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7441	74.41%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9113	91.13%
Skin irritation	-	0.5211	52.11%
Skin corrosion	-	0.9578	95.78%
Ames mutagenesis	-	0.6664	66.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.4558	45.58%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.5980	59.80%
skin sensitisation	-	0.8894	88.94%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7447	74.47%
Acute Oral Toxicity (c)	III	0.7777	77.77%
Estrogen receptor binding	+	0.7349	73.49%
Androgen receptor binding	+	0.7624	76.24%
Thyroid receptor binding	+	0.5269	52.69%
Glucocorticoid receptor binding	+	0.8096	80.96%
Aromatase binding	+	0.7025	70.25%
PPAR gamma	+	0.7515	75.15%
Honey bee toxicity	-	0.6709	67.09%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9916	99.16%

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	99.11%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.82%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	97.35%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.73%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.83%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.59%	97.25%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.30%	91.07%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	88.92%	94.33%
CHEMBL299	P17252	Protein kinase C alpha	88.60%	98.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.27%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.85%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	87.06%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.94%	95.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.03%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.72%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.06%	92.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.00%	96.77%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.81%	99.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.15%	91.24%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.14%	91.03%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	83.11%	85.30%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.76%	94.00%
CHEMBL5028	O14672	ADAM10	81.01%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.29%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.22%	82.69%
CHEMBL1937	Q92769	Histone deacetylase 2	80.01%	94.75%

Plants that contains it

• Peperomia trineura
• Symplocos paniculata

Cross-Links

• PubChem: 16099384
• LOTUS: LTS0194575
• wikiData: Q105291449