(3S,3aR,4R,6aR,8S,9aR,9bR)-3-methyl-2,6,9-trimethylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-4,8-diol

Details

• Internal ID: e6656dd5-df39-4516-8758-457ef1b9465a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Guaianes
• IUPAC Name: (3S,3aR,4R,6aR,8S,9aR,9bR)-3-methyl-2,6,9-trimethylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-4,8-diol
• SMILES (Canonical): CC1C2C(CC(=C)C3CC(C(=C)C3C2OC1=C)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@@H](CC(=C)[C@@H]3C[C@@H](C(=C)[C@@H]3[C@H]2OC1=C)O)O
• InChI: InChI=1S/C16H22O3/c1-7-5-13(18)15-8(2)10(4)19-16(15)14-9(3)12(17)6-11(7)14/h8,11-18H,1,3-6H2,2H3/t8-,11+,12+,13-,14+,15-,16-/m1/s1
• InChI Key: UJDFNGCIJHGKNW-QJTLGEBBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₃
• Molecular Weight: 262.34 g/mol
• Exact Mass: 262.15689456 g/mol
• Topological Polar Surface Area (TPSA): 49.70 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 2.03
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9930	99.30%
Caco-2	-	0.6847	68.47%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Lysosomes	0.4501	45.01%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.8610	86.10%
OATP1B3 inhibitior	+	0.9633	96.33%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9677	96.77%
P-glycoprotein inhibitior	-	0.9083	90.83%
P-glycoprotein substrate	-	0.7126	71.26%
CYP3A4 substrate	+	0.5395	53.95%
CYP2C9 substrate	-	0.7979	79.79%
CYP2D6 substrate	-	0.6951	69.51%
CYP3A4 inhibition	-	0.8619	86.19%
CYP2C9 inhibition	-	0.8757	87.57%
CYP2C19 inhibition	-	0.7472	74.72%
CYP2D6 inhibition	-	0.9429	94.29%
CYP1A2 inhibition	-	0.5865	58.65%
CYP2C8 inhibition	-	0.8834	88.34%
CYP inhibitory promiscuity	-	0.6634	66.34%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9008	90.08%
Carcinogenicity (trinary)	Non-required	0.3901	39.01%
Eye corrosion	-	0.9242	92.42%
Eye irritation	-	0.7874	78.74%
Skin irritation	-	0.5840	58.40%
Skin corrosion	-	0.8471	84.71%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6800	68.00%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.6409	64.09%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.6541	65.41%
Acute Oral Toxicity (c)	III	0.4777	47.77%
Estrogen receptor binding	+	0.5333	53.33%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5144	51.44%
Aromatase binding	-	0.6619	66.19%
PPAR gamma	-	0.7394	73.94%
Honey bee toxicity	-	0.7596	75.96%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.7437	74.37%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL241	Q14432	Phosphodiesterase 3A	87.08%	92.94%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.83%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.04%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	85.88%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.51%	96.09%
CHEMBL1871	P10275	Androgen Receptor	82.87%	96.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.24%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.05%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.51%	95.89%
CHEMBL1977	P11473	Vitamin D receptor	80.15%	99.43%
CHEMBL308	P06493	Cyclin-dependent kinase 1	80.04%	91.73%

Plants that contains it

• Crepis crocea

Cross-Links

• PubChem: 163190654
• LOTUS: LTS0103090
• wikiData: Q105273873