(1S,4aR,5S,8aS)-5-[(E)-5-hydroxy-3-methylpent-3-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid

Details

• Internal ID: 0f3b8546-8040-44e1-a276-8150a2f07d12
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1S,4aR,5S,8aS)-5-[(E)-5-hydroxy-3-methylpent-3-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• SMILES (Canonical): CC(=CCO)CCC1C(=C)CCC2C1(CCCC2(C)C(=O)O)C
• SMILES (Isomeric): C/C(=C\CO)/CC[C@H]1C(=C)CC[C@H]2[C@@]1(CCC[C@]2(C)C(=O)O)C
• InChI: InChI=1S/C20H32O3/c1-14(10-13-21)6-8-16-15(2)7-9-17-19(16,3)11-5-12-20(17,4)18(22)23/h10,16-17,21H,2,5-9,11-13H2,1,3-4H3,(H,22,23)/b14-10+/t16-,17-,19+,20-/m0/s1
• InChI Key: DOYKMKZYLAAOGH-UGUQBNQJSA-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: 4.60
• Atomic LogP (AlogP): 4.57
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9900	99.00%
Caco-2	+	0.8582	85.82%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6483	64.83%
OATP2B1 inhibitior	-	0.8629	86.29%
OATP1B1 inhibitior	+	0.7894	78.94%
OATP1B3 inhibitior	-	0.2208	22.08%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.5491	54.91%
BSEP inhibitior	+	0.7048	70.48%
P-glycoprotein inhibitior	-	0.7077	70.77%
P-glycoprotein substrate	-	0.8027	80.27%
CYP3A4 substrate	+	0.6102	61.02%
CYP2C9 substrate	-	0.6197	61.97%
CYP2D6 substrate	-	0.8732	87.32%
CYP3A4 inhibition	-	0.5838	58.38%
CYP2C9 inhibition	-	0.6188	61.88%
CYP2C19 inhibition	-	0.7708	77.08%
CYP2D6 inhibition	-	0.9064	90.64%
CYP1A2 inhibition	-	0.8062	80.62%
CYP2C8 inhibition	-	0.6586	65.86%
CYP inhibitory promiscuity	-	0.6900	69.00%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6467	64.67%
Eye corrosion	-	0.9828	98.28%
Eye irritation	-	0.8045	80.45%
Skin irritation	-	0.7192	71.92%
Skin corrosion	-	0.9789	97.89%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7374	73.74%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.7819	78.19%
skin sensitisation	-	0.5499	54.99%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.6187	61.87%
Acute Oral Toxicity (c)	III	0.6356	63.56%
Estrogen receptor binding	+	0.5934	59.34%
Androgen receptor binding	+	0.5978	59.78%
Thyroid receptor binding	+	0.6638	66.38%
Glucocorticoid receptor binding	+	0.6993	69.93%
Aromatase binding	+	0.5903	59.03%
PPAR gamma	+	0.5634	56.34%
Honey bee toxicity	-	0.9165	91.65%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
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	97.01%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.68%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.17%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.86%	97.25%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.23%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	85.39%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.63%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.13%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.39%	96.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.99%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.39%	100.00%

Plants that contains it

• Cryptomeria japonica
• Platycladus orientalis

Cross-Links

• PubChem: 162890675
• LOTUS: LTS0274482
• wikiData: Q104986321