3-[[(4aS,5R,8S,8aR)-8-hydroxy-5-methyl-8-propan-2-yl-4,4a,5,6,7,8a-hexahydro-3H-naphthalen-2-yl]methoxy]-3-oxopropanoic acid

Details

• Internal ID: 6c6bf14b-69ed-4a9f-96a6-be3534d94f8f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: 3-[[(4aS,5R,8S,8aR)-8-hydroxy-5-methyl-8-propan-2-yl-4,4a,5,6,7,8a-hexahydro-3H-naphthalen-2-yl]methoxy]-3-oxopropanoic acid
• SMILES (Canonical): CC1CCC(C2C1CCC(=C2)COC(=O)CC(=O)O)(C(C)C)O
• SMILES (Isomeric): C[C@@H]1CC[C@@]([C@@H]2[C@H]1CCC(=C2)COC(=O)CC(=O)O)(C(C)C)O
• InChI: InChI=1S/C18H28O5/c1-11(2)18(22)7-6-12(3)14-5-4-13(8-15(14)18)10-23-17(21)9-16(19)20/h8,11-12,14-15,22H,4-7,9-10H2,1-3H3,(H,19,20)/t12-,14+,15+,18+/m1/s1
• InChI Key: SAXZVTNJSXEHAJ-FHIHXZLISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₈O₅
• Molecular Weight: 324.40 g/mol
• Exact Mass: 324.19367399 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.77
• H-Bond Acceptor: 4
• 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	+	0.9914	99.14%
Caco-2	+	0.4923	49.23%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8954	89.54%
OATP2B1 inhibitior	-	0.8629	86.29%
OATP1B1 inhibitior	+	0.9148	91.48%
OATP1B3 inhibitior	+	0.8371	83.71%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6525	65.25%
BSEP inhibitior	+	0.7411	74.11%
P-glycoprotein inhibitior	-	0.8405	84.05%
P-glycoprotein substrate	-	0.6219	62.19%
CYP3A4 substrate	+	0.5896	58.96%
CYP2C9 substrate	-	0.6031	60.31%
CYP2D6 substrate	-	0.8843	88.43%
CYP3A4 inhibition	-	0.8048	80.48%
CYP2C9 inhibition	-	0.7380	73.80%
CYP2C19 inhibition	-	0.8575	85.75%
CYP2D6 inhibition	-	0.9350	93.50%
CYP1A2 inhibition	-	0.8187	81.87%
CYP2C8 inhibition	-	0.7726	77.26%
CYP inhibitory promiscuity	-	0.8944	89.44%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6543	65.43%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.8716	87.16%
Skin irritation	-	0.6190	61.90%
Skin corrosion	-	0.9730	97.30%
Ames mutagenesis	-	0.8024	80.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.4350	43.50%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.5201	52.01%
skin sensitisation	-	0.7673	76.73%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.9043	90.43%
Acute Oral Toxicity (c)	III	0.5082	50.82%
Estrogen receptor binding	+	0.7396	73.96%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5771	57.71%
Glucocorticoid receptor binding	+	0.6358	63.58%
Aromatase binding	-	0.5250	52.50%
PPAR gamma	+	0.5891	58.91%
Honey bee toxicity	-	0.8963	89.63%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.78%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.28%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	94.54%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.14%	97.25%
CHEMBL2581	P07339	Cathepsin D	92.39%	98.95%
CHEMBL4227	P25090	Lipoxin A4 receptor	89.41%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	85.63%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.46%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	83.19%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.47%	97.09%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.04%	94.33%

Plants that contains it

• Fabiana imbricata

Cross-Links

• PubChem: 162984407
• LOTUS: LTS0111784
• wikiData: Q105249216