3-[(1R,2S,3S,6E)-3-hydroxy-2-[(3E,7E)-5-hydroxy-4,8,12-trimethyltrideca-3,7,11-trienyl]-2,3-dimethyl-6-(1-oxopropan-2-ylidene)cyclohexyl]propyl (9E,12E)-octadeca-9,12-dienoate

Details

• Internal ID: a3ea57e8-124a-498b-ad1d-ee9ec7acfcff
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesterterpenoids
• IUPAC Name: 3-[(1R,2S,3S,6E)-3-hydroxy-2-[(3E,7E)-5-hydroxy-4,8,12-trimethyltrideca-3,7,11-trienyl]-2,3-dimethyl-6-(1-oxopropan-2-ylidene)cyclohexyl]propyl (9E,12E)-octadeca-9,12-dienoate
• SMILES (Canonical): CCCCCC=CCC=CCCCCCCCC(=O)OCCCC1C(=C(C)C=O)CCC(C1(C)CCC=C(C)C(CC=C(C)CCC=C(C)C)O)(C)O
• SMILES (Isomeric): CCCCC/C=C/C/C=C/CCCCCCCC(=O)OCCC[C@@H]1/C(=C(\C)/C=O)/CC[C@]([C@@]1(C)CC/C=C(\C)/C(C/C=C(\C)/CCC=C(C)C)O)(C)O
• InChI: InChI=1S/C48H80O5/c1-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-31-46(51)53-37-26-30-44-43(42(6)38-49)34-36-48(8,52)47(44,7)35-25-29-41(5)45(50)33-32-40(4)28-24-27-39(2)3/h13-14,16-17,27,29,32,38,44-45,50,52H,9-12,15,18-26,28,30-31,33-37H2,1-8H3/b14-13+,17-16+,40-32+,41-29+,43-42+/t44-,45?,47+,48+/m1/s1
• InChI Key: OKJNXNRPQNRJBB-FMEMFQLLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₈₀O₅
• Molecular Weight: 737.10 g/mol
• Exact Mass: 736.60057565 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 13.20
• Atomic LogP (AlogP): 12.98
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 28

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9899	98.99%
Caco-2	-	0.8253	82.53%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.9260	92.60%
OATP2B1 inhibitior	+	0.5707	57.07%
OATP1B1 inhibitior	+	0.7855	78.55%
OATP1B3 inhibitior	+	0.9221	92.21%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6275	62.75%
BSEP inhibitior	+	0.9704	97.04%
P-glycoprotein inhibitior	+	0.7685	76.85%
P-glycoprotein substrate	+	0.6654	66.54%
CYP3A4 substrate	+	0.7344	73.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9078	90.78%
CYP3A4 inhibition	-	0.6458	64.58%
CYP2C9 inhibition	-	0.7743	77.43%
CYP2C19 inhibition	-	0.8980	89.80%
CYP2D6 inhibition	-	0.8752	87.52%
CYP1A2 inhibition	-	0.9060	90.60%
CYP2C8 inhibition	+	0.7428	74.28%
CYP inhibitory promiscuity	-	0.8599	85.99%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6561	65.61%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9076	90.76%
Skin irritation	-	0.6644	66.44%
Skin corrosion	-	0.9832	98.32%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8338	83.38%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.6724	67.24%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.7059	70.59%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.8200	82.00%
Acute Oral Toxicity (c)	III	0.5663	56.63%
Estrogen receptor binding	+	0.8119	81.19%
Androgen receptor binding	+	0.6811	68.11%
Thyroid receptor binding	+	0.5152	51.52%
Glucocorticoid receptor binding	+	0.7320	73.20%
Aromatase binding	+	0.5735	57.35%
PPAR gamma	+	0.6829	68.29%
Honey bee toxicity	-	0.7900	79.00%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6678	66.78%
Fish aquatic toxicity	+	0.9962	99.62%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.09%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.22%	94.45%
CHEMBL2581	P07339	Cathepsin D	97.94%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.97%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.70%	91.11%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	96.26%	92.86%
CHEMBL221	P23219	Cyclooxygenase-1	96.18%	90.17%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	95.67%	92.08%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	93.44%	91.24%
CHEMBL4227	P25090	Lipoxin A4 receptor	92.72%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	89.32%	100.00%
CHEMBL299	P17252	Protein kinase C alpha	88.65%	98.03%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	88.07%	85.94%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	87.31%	97.50%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	87.19%	97.29%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	86.13%	96.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.51%	98.75%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.25%	93.56%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	85.06%	96.90%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	84.80%	95.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.61%	95.89%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.54%	94.62%
CHEMBL239	Q07869	Peroxisome proliferator-activated receptor alpha	84.33%	90.75%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	83.89%	85.30%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.67%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.67%	97.09%
CHEMBL3891	P07384	Calpain 1	83.13%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.80%	89.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.58%	95.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.24%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	81.52%	92.50%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.32%	93.03%
CHEMBL2996	Q05655	Protein kinase C delta	81.13%	97.79%
CHEMBL340	P08684	Cytochrome P450 3A4	81.03%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.46%	100.00%
CHEMBL230	P35354	Cyclooxygenase-2	80.21%	89.63%

Plants that contains it

• Iris tectorum

Cross-Links

• PubChem: 101663363
• LOTUS: LTS0000478
• wikiData: Q105193593