(3R,6E,10Z,14E)-10-(acetyloxymethyl)-16-hydroxy-14-(hydroxymethyl)-3,6-dimethyl-2-methylidenehexadeca-6,10,14-trienoic acid

Details

• Internal ID: 32c1936f-35b6-427e-b3d6-4431e1808c56
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Acyclic diterpenoids
• IUPAC Name: (3R,6E,10Z,14E)-10-(acetyloxymethyl)-16-hydroxy-14-(hydroxymethyl)-3,6-dimethyl-2-methylidenehexadeca-6,10,14-trienoic acid
• SMILES (Canonical): CC(CCC(=CCCC(=CCCC(=CCO)CO)COC(=O)C)C)C(=C)C(=O)O
• SMILES (Isomeric): C[C@H](CC/C(=C/CC/C(=C/CC/C(=C\CO)/CO)/COC(=O)C)/C)C(=C)C(=O)O
• InChI: InChI=1S/C23H36O6/c1-17(11-12-18(2)19(3)23(27)28)7-5-9-22(16-29-20(4)26)10-6-8-21(15-25)13-14-24/h7,10,13,18,24-25H,3,5-6,8-9,11-12,14-16H2,1-2,4H3,(H,27,28)/b17-7+,21-13+,22-10-/t18-/m1/s1
• InChI Key: PIUYIJJDDFMMLN-YQZOUTSOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₆O₆
• Molecular Weight: 408.50 g/mol
• Exact Mass: 408.25118886 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.95
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8841	88.41%
Caco-2	-	0.6369	63.69%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7377	73.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9127	91.27%
OATP1B3 inhibitior	+	0.9258	92.58%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7467	74.67%
P-glycoprotein inhibitior	+	0.5922	59.22%
P-glycoprotein substrate	-	0.6669	66.69%
CYP3A4 substrate	+	0.5641	56.41%
CYP2C9 substrate	+	0.8005	80.05%
CYP2D6 substrate	-	0.9033	90.33%
CYP3A4 inhibition	-	0.5883	58.83%
CYP2C9 inhibition	-	0.7915	79.15%
CYP2C19 inhibition	-	0.8481	84.81%
CYP2D6 inhibition	-	0.8772	87.72%
CYP1A2 inhibition	-	0.8074	80.74%
CYP2C8 inhibition	-	0.8697	86.97%
CYP inhibitory promiscuity	-	0.8926	89.26%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7223	72.23%
Carcinogenicity (trinary)	Non-required	0.7087	70.87%
Eye corrosion	-	0.8744	87.44%
Eye irritation	-	0.8202	82.02%
Skin irritation	-	0.6663	66.63%
Skin corrosion	-	0.9864	98.64%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6477	64.77%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	-	0.5947	59.47%
skin sensitisation	-	0.6952	69.52%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	-	0.9111	91.11%
Mitochondrial toxicity	-	0.8500	85.00%
Nephrotoxicity	+	0.4805	48.05%
Acute Oral Toxicity (c)	IV	0.5312	53.12%
Estrogen receptor binding	+	0.7013	70.13%
Androgen receptor binding	-	0.6360	63.60%
Thyroid receptor binding	+	0.6164	61.64%
Glucocorticoid receptor binding	+	0.6685	66.85%
Aromatase binding	-	0.5061	50.61%
PPAR gamma	+	0.6453	64.53%
Honey bee toxicity	-	0.8534	85.34%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7255	72.55%
Fish aquatic toxicity	+	0.9952	99.52%

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	96.03%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.10%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.59%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.22%	99.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.06%	93.00%
CHEMBL340	P08684	Cytochrome P450 3A4	87.95%	91.19%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.37%	96.47%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.82%	96.00%
CHEMBL4040	P28482	MAP kinase ERK2	82.60%	83.82%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.58%	93.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.00%	86.33%

Plants that contains it

• Helogyne apaloidea

Cross-Links

• PubChem: 163017675
• LOTUS: LTS0109602
• wikiData: Q105209739