2-[(2R,4aS,7S)-7-hydroxy-4a-methyl-8-methylidene-1,2,3,4,7,8a-hexahydronaphthalen-2-yl]prop-2-enoic acid

Details

• Internal ID: 1ffc0f02-11fa-4934-85b5-355a9ca2ae96
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4aS,7S)-7-hydroxy-4a-methyl-8-methylidene-1,2,3,4,7,8a-hexahydronaphthalen-2-yl]prop-2-enoic acid
• InChI: InChI=1S/C15H20O3/c1-9(14(17)18)11-4-6-15(3)7-5-13(16)10(2)12(15)8-11/h5,7,11-13,16H,1-2,4,6,8H2,3H3,(H,17,18)/t11-,12?,13+,15+/m1/s1
• InChI Key: OLROVKXKIOIJDQ-YKURLNKLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.54
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9942	99.42%
Caco-2	+	0.5139	51.39%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7213	72.13%
OATP2B1 inhibitior	-	0.8541	85.41%
OATP1B1 inhibitior	+	0.9040	90.40%
OATP1B3 inhibitior	+	0.9188	91.88%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.5181	51.81%
BSEP inhibitior	-	0.8123	81.23%
P-glycoprotein inhibitior	-	0.9247	92.47%
P-glycoprotein substrate	-	0.7943	79.43%
CYP3A4 substrate	+	0.5845	58.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8836	88.36%
CYP3A4 inhibition	-	0.7841	78.41%
CYP2C9 inhibition	-	0.8641	86.41%
CYP2C19 inhibition	-	0.7769	77.69%
CYP2D6 inhibition	-	0.8974	89.74%
CYP1A2 inhibition	-	0.6375	63.75%
CYP2C8 inhibition	-	0.8404	84.04%
CYP inhibitory promiscuity	-	0.8178	81.78%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5394	53.94%
Eye corrosion	-	0.9843	98.43%
Eye irritation	-	0.5909	59.09%
Skin irritation	+	0.5127	51.27%
Skin corrosion	-	0.9460	94.60%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5317	53.17%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	+	0.5563	55.63%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.6982	69.82%
Acute Oral Toxicity (c)	III	0.7423	74.23%
Estrogen receptor binding	-	0.5833	58.33%
Androgen receptor binding	-	0.5660	56.60%
Thyroid receptor binding	-	0.5747	57.47%
Glucocorticoid receptor binding	+	0.6831	68.31%
Aromatase binding	-	0.6859	68.59%
PPAR gamma	+	0.5342	53.42%
Honey bee toxicity	-	0.9241	92.41%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.79%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.60%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.21%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	89.99%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.33%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.59%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	82.33%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.15%	89.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.11%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.10%	100.00%
CHEMBL2581	P07339	Cathepsin D	80.66%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	80.61%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.30%	99.23%
CHEMBL4208	P20618	Proteasome component C5	80.00%	90.00%

Plants that contains it

• Cheirolophus sempervirens

Cross-Links

• PubChem: 162873903
• LOTUS: LTS0060972
• wikiData: Q105194101