(E)-5-[(1S,4aR,6R,8aR)-6-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid

Details

• Internal ID: 5ed7d2b7-dad2-4713-9fd8-10a89f171eaf
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (E)-5-[(1S,4aR,6R,8aR)-6-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid
• SMILES (Canonical): CC(=CC(=O)O)CCC1C(=C)CCC2C1(CCC(C2(C)C)O)C
• SMILES (Isomeric): C/C(=C\C(=O)O)/CC[C@H]1C(=C)CC[C@@H]2[C@@]1(CC[C@H](C2(C)C)O)C
• InChI: InChI=1S/C20H32O3/c1-13(12-18(22)23)6-8-15-14(2)7-9-16-19(3,4)17(21)10-11-20(15,16)5/h12,15-17,21H,2,6-11H2,1,3-5H3,(H,22,23)/b13-12+/t15-,16-,17+,20+/m0/s1
• InChI Key: LNWOKEZJIRLIDO-YDQXQCNRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.50 g/mol
• Exact Mass: 320.23514488 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.57
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9956	99.56%
Caco-2	+	0.7413	74.13%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8128	81.28%
OATP2B1 inhibitior	-	0.8625	86.25%
OATP1B1 inhibitior	+	0.8749	87.49%
OATP1B3 inhibitior	+	0.8703	87.03%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.6507	65.07%
P-glycoprotein inhibitior	-	0.7862	78.62%
P-glycoprotein substrate	-	0.8470	84.70%
CYP3A4 substrate	+	0.6459	64.59%
CYP2C9 substrate	-	0.7928	79.28%
CYP2D6 substrate	-	0.9050	90.50%
CYP3A4 inhibition	-	0.6803	68.03%
CYP2C9 inhibition	-	0.9015	90.15%
CYP2C19 inhibition	-	0.8585	85.85%
CYP2D6 inhibition	-	0.9554	95.54%
CYP1A2 inhibition	-	0.9401	94.01%
CYP2C8 inhibition	-	0.7204	72.04%
CYP inhibitory promiscuity	-	0.8490	84.90%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6834	68.34%
Eye corrosion	-	0.9943	99.43%
Eye irritation	-	0.7056	70.56%
Skin irritation	+	0.5839	58.39%
Skin corrosion	-	0.9611	96.11%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7468	74.68%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.7226	72.26%
skin sensitisation	+	0.5693	56.93%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.8225	82.25%
Acute Oral Toxicity (c)	III	0.6607	66.07%
Estrogen receptor binding	+	0.6527	65.27%
Androgen receptor binding	+	0.6713	67.13%
Thyroid receptor binding	+	0.6494	64.94%
Glucocorticoid receptor binding	+	0.7479	74.79%
Aromatase binding	+	0.5609	56.09%
PPAR gamma	+	0.6627	66.27%
Honey bee toxicity	-	0.8404	84.04%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	98.07%	83.82%
CHEMBL221	P23219	Cyclooxygenase-1	94.03%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.39%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.86%	100.00%
CHEMBL2061	P19793	Retinoid X receptor alpha	85.80%	91.67%
CHEMBL2581	P07339	Cathepsin D	84.55%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.04%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.74%	94.45%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.42%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.31%	91.19%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.49%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.08%	95.56%

Plants that contains it

• Metasequoia glyptostroboides

Cross-Links

• PubChem: 162916164
• LOTUS: LTS0210367
• wikiData: Q105154546