(E)-5-[(1S,4aR,7R,8aS)-7-hydroxy-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid

Details

• Internal ID: f69378ba-c1b4-42b1-8500-a0761223c313
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (E)-5-[(1S,4aR,7R,8aS)-7-hydroxy-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid
• SMILES (Canonical): CC(=CC(=O)O)CCC1C(=CCC2C1(CC(CC2(C)C)O)C)CO
• SMILES (Isomeric): C/C(=C\C(=O)O)/CC[C@@H]1C(=CC[C@H]2[C@@]1(C[C@@H](CC2(C)C)O)C)CO
• InChI: InChI=1S/C20H32O4/c1-13(9-18(23)24)5-7-16-14(12-21)6-8-17-19(2,3)10-15(22)11-20(16,17)4/h6,9,15-17,21-22H,5,7-8,10-12H2,1-4H3,(H,23,24)/b13-9+/t15-,16-,17-,20-/m1/s1
• InChI Key: ZQBRPFALTAJQEA-FCVDOSRFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.50 g/mol
• Exact Mass: 336.23005950 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.54
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9891	98.91%
Caco-2	+	0.6172	61.72%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8286	82.86%
OATP2B1 inhibitior	-	0.8674	86.74%
OATP1B1 inhibitior	+	0.8445	84.45%
OATP1B3 inhibitior	+	0.8354	83.54%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.5051	50.51%
BSEP inhibitior	+	0.6493	64.93%
P-glycoprotein inhibitior	-	0.8144	81.44%
P-glycoprotein substrate	-	0.6986	69.86%
CYP3A4 substrate	+	0.5903	59.03%
CYP2C9 substrate	-	0.8058	80.58%
CYP2D6 substrate	-	0.9065	90.65%
CYP3A4 inhibition	-	0.7216	72.16%
CYP2C9 inhibition	-	0.9152	91.52%
CYP2C19 inhibition	-	0.9419	94.19%
CYP2D6 inhibition	-	0.9205	92.05%
CYP1A2 inhibition	-	0.8842	88.42%
CYP2C8 inhibition	-	0.6717	67.17%
CYP inhibitory promiscuity	-	0.8545	85.45%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7069	70.69%
Eye corrosion	-	0.9945	99.45%
Eye irritation	-	0.9246	92.46%
Skin irritation	+	0.5415	54.15%
Skin corrosion	-	0.9741	97.41%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3876	38.76%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.7601	76.01%
skin sensitisation	-	0.7005	70.05%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.5965	59.65%
Acute Oral Toxicity (c)	III	0.8685	86.85%
Estrogen receptor binding	+	0.7155	71.55%
Androgen receptor binding	+	0.6510	65.10%
Thyroid receptor binding	+	0.5893	58.93%
Glucocorticoid receptor binding	+	0.7759	77.59%
Aromatase binding	+	0.6564	65.64%
PPAR gamma	+	0.6032	60.32%
Honey bee toxicity	-	0.8044	80.44%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9894	98.94%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	97.34%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.16%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.78%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.31%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.06%	94.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.93%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	85.88%	90.17%
CHEMBL2581	P07339	Cathepsin D	85.42%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.86%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.66%	100.00%

Plants that contains it

• Dodonaea microzyga

Cross-Links

• PubChem: 162859095
• LOTUS: LTS0011813
• wikiData: Q105381374