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

Details

• Internal ID: c9108197-4976-4641-b0e4-a3b8d6ef73fa
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4aS,7R,8aS)-7,8a-dihydroxy-4a-methyl-8-methylidene-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC12CCC(CC1(C(=C)C(CC2)O)O)C(=C)C(=O)O
• SMILES (Isomeric): C[C@@]12CC[C@H](C[C@]1(C(=C)[C@@H](CC2)O)O)C(=C)C(=O)O
• InChI: InChI=1S/C15H22O4/c1-9(13(17)18)11-4-6-14(3)7-5-12(16)10(2)15(14,19)8-11/h11-12,16,19H,1-2,4-8H2,3H3,(H,17,18)/t11-,12-,14+,15-/m1/s1
• InChI Key: FCBNTAJEZHMKMS-RJZRQDKASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.88
• 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	+	0.9836	98.36%
Caco-2	+	0.5118	51.18%
Blood Brain Barrier	-	0.7473	74.73%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7221	72.21%
OATP2B1 inhibitior	-	0.8521	85.21%
OATP1B1 inhibitior	+	0.9220	92.20%
OATP1B3 inhibitior	+	0.7963	79.63%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6728	67.28%
BSEP inhibitior	-	0.8863	88.63%
P-glycoprotein inhibitior	-	0.9489	94.89%
P-glycoprotein substrate	-	0.8317	83.17%
CYP3A4 substrate	+	0.5494	54.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8918	89.18%
CYP3A4 inhibition	-	0.8303	83.03%
CYP2C9 inhibition	-	0.8896	88.96%
CYP2C19 inhibition	-	0.8666	86.66%
CYP2D6 inhibition	-	0.9312	93.12%
CYP1A2 inhibition	-	0.8225	82.25%
CYP2C8 inhibition	-	0.8732	87.32%
CYP inhibitory promiscuity	-	0.9412	94.12%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6008	60.08%
Eye corrosion	-	0.9900	99.00%
Eye irritation	+	0.6453	64.53%
Skin irritation	+	0.5331	53.31%
Skin corrosion	-	0.9167	91.67%
Ames mutagenesis	-	0.7137	71.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6910	69.10%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.6532	65.32%
skin sensitisation	-	0.6540	65.40%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.7406	74.06%
Acute Oral Toxicity (c)	III	0.3569	35.69%
Estrogen receptor binding	+	0.6291	62.91%
Androgen receptor binding	-	0.4907	49.07%
Thyroid receptor binding	-	0.5875	58.75%
Glucocorticoid receptor binding	+	0.7470	74.70%
Aromatase binding	+	0.5725	57.25%
PPAR gamma	-	0.5754	57.54%
Honey bee toxicity	-	0.9356	93.56%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9947	99.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	95.01%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.56%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.98%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.86%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	81.04%	91.19%
CHEMBL2581	P07339	Cathepsin D	80.32%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.20%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.01%	95.89%

Plants that contains it

• Chiliadenus montanus

Cross-Links

• PubChem: 13895639
• LOTUS: LTS0069415
• wikiData: Q104993052