(5S,5aS,7R,8aR,9S)-7-(hydroxymethyl)-5,7-dimethyl-4,5a,6,8,8a,9-hexahydroazuleno[5,6-c]furan-5,9-diol

Details

• Internal ID: 1bd66784-3035-43c9-a483-d0f53557e54a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (5S,5aS,7R,8aR,9S)-7-(hydroxymethyl)-5,7-dimethyl-4,5a,6,8,8a,9-hexahydroazuleno[5,6-c]furan-5,9-diol
• SMILES (Canonical): CC1(CC2C(C1)C(CC3=COC=C3C2O)(C)O)CO
• SMILES (Isomeric): C[C@]1(C[C@@H]2[C@H](C1)[C@@](CC3=COC=C3[C@H]2O)(C)O)CO
• InChI: InChI=1S/C15H22O4/c1-14(8-16)4-10-12(5-14)15(2,18)3-9-6-19-7-11(9)13(10)17/h6-7,10,12-13,16-18H,3-5,8H2,1-2H3/t10-,12+,13+,14-,15+/m1/s1
• InChI Key: LPXNISGTRUGQGS-NZNQWUEYSA-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): 73.80 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.64
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9848	98.48%
Caco-2	+	0.6959	69.59%
Blood Brain Barrier	+	0.6135	61.35%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Lysosomes	0.5148	51.48%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.8886	88.86%
OATP1B3 inhibitior	+	0.9508	95.08%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9067	90.67%
BSEP inhibitior	-	0.9116	91.16%
P-glycoprotein inhibitior	-	0.9656	96.56%
P-glycoprotein substrate	-	0.7363	73.63%
CYP3A4 substrate	+	0.5805	58.05%
CYP2C9 substrate	+	0.5814	58.14%
CYP2D6 substrate	-	0.6977	69.77%
CYP3A4 inhibition	-	0.8637	86.37%
CYP2C9 inhibition	-	0.8185	81.85%
CYP2C19 inhibition	-	0.7794	77.94%
CYP2D6 inhibition	-	0.9288	92.88%
CYP1A2 inhibition	-	0.6603	66.03%
CYP2C8 inhibition	-	0.7535	75.35%
CYP inhibitory promiscuity	-	0.9121	91.21%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6075	60.75%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9714	97.14%
Skin irritation	-	0.7893	78.93%
Skin corrosion	-	0.9512	95.12%
Ames mutagenesis	-	0.5578	55.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.4007	40.07%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.5319	53.19%
skin sensitisation	-	0.8257	82.57%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6947	69.47%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.4932	49.32%
Acute Oral Toxicity (c)	III	0.5517	55.17%
Estrogen receptor binding	+	0.7264	72.64%
Androgen receptor binding	-	0.5699	56.99%
Thyroid receptor binding	+	0.5955	59.55%
Glucocorticoid receptor binding	+	0.5502	55.02%
Aromatase binding	-	0.5314	53.14%
PPAR gamma	-	0.6113	61.13%
Honey bee toxicity	-	0.8641	86.41%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8566	85.66%

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	97.62%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.49%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.45%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.89%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.22%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	89.09%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.86%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.16%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	84.99%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.91%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.32%	89.00%

Plants that contains it

• Anastatica hierochuntica
• Maclura cochinchinensis

Cross-Links

• PubChem: 14488477
• NPASS: NPC18235
• LOTUS: LTS0232374
• wikiData: Q105155391