2-[(2R,4aR,8R,8aS)-8,8a-dihydroxy-4a,8-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid

Details

• Internal ID: fd730dd5-8d3f-41f0-b609-47f7691a1481
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4aR,8R,8aS)-8,8a-dihydroxy-4a,8-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC12CCCC(C1(CC(CC2)C(=C)C(=O)O)O)(C)O
• SMILES (Isomeric): C[C@]12CCC[C@@]([C@@]1(C[C@@H](CC2)C(=C)C(=O)O)O)(C)O
• InChI: InChI=1S/C15H24O4/c1-10(12(16)17)11-5-8-13(2)6-4-7-14(3,18)15(13,19)9-11/h11,18-19H,1,4-9H2,2-3H3,(H,16,17)/t11-,13-,14-,15+/m1/s1
• InChI Key: BWSMNSAZRMJSSZ-NGFQHRJXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₄
• Molecular Weight: 268.35 g/mol
• Exact Mass: 268.16745924 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.10
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9807	98.07%
Caco-2	+	0.7041	70.41%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8211	82.11%
OATP2B1 inhibitior	-	0.8495	84.95%
OATP1B1 inhibitior	+	0.9361	93.61%
OATP1B3 inhibitior	+	0.8517	85.17%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6641	66.41%
BSEP inhibitior	-	0.8751	87.51%
P-glycoprotein inhibitior	-	0.9585	95.85%
P-glycoprotein substrate	-	0.8453	84.53%
CYP3A4 substrate	+	0.5704	57.04%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8993	89.93%
CYP3A4 inhibition	-	0.7885	78.85%
CYP2C9 inhibition	-	0.9319	93.19%
CYP2C19 inhibition	-	0.8904	89.04%
CYP2D6 inhibition	-	0.9345	93.45%
CYP1A2 inhibition	-	0.8654	86.54%
CYP2C8 inhibition	-	0.9046	90.46%
CYP inhibitory promiscuity	-	0.9752	97.52%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6459	64.59%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.6377	63.77%
Skin irritation	+	0.6097	60.97%
Skin corrosion	-	0.9365	93.65%
Ames mutagenesis	-	0.7337	73.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6125	61.25%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.5585	55.85%
skin sensitisation	-	0.6118	61.18%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6319	63.19%
Acute Oral Toxicity (c)	III	0.5591	55.91%
Estrogen receptor binding	+	0.7968	79.68%
Androgen receptor binding	+	0.5930	59.30%
Thyroid receptor binding	-	0.5656	56.56%
Glucocorticoid receptor binding	+	0.6687	66.87%
Aromatase binding	+	0.6581	65.81%
PPAR gamma	+	0.5458	54.58%
Honey bee toxicity	-	0.9144	91.44%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9968	99.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.95%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.58%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.54%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	85.44%	90.17%
CHEMBL217	P14416	Dopamine D2 receptor	84.11%	95.62%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.63%	82.69%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.54%	96.38%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.31%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.88%	91.19%
CHEMBL2581	P07339	Cathepsin D	80.87%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.28%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.20%	95.56%

Plants that contains it

• Laggera crispata

Cross-Links

• PubChem: 162860101
• LOTUS: LTS0215073
• wikiData: Q104947628