(5R,8S,8aS)-5-[(2R)-1,2-dihydroxypropan-2-yl]-3,8-dimethyl-4,5,6,7,8,8a-hexahydro-1H-azulen-2-one

Details

• Internal ID: 8d5afadf-4951-4653-a881-9b268bc3434f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Guaianes
• IUPAC Name: (5R,8S,8aS)-5-[(2R)-1,2-dihydroxypropan-2-yl]-3,8-dimethyl-4,5,6,7,8,8a-hexahydro-1H-azulen-2-one
• SMILES (Canonical): CC1CCC(CC2=C(C(=O)CC12)C)C(C)(CO)O
• SMILES (Isomeric): C[C@H]1CC[C@H](CC2=C(C(=O)C[C@@H]12)C)[C@](C)(CO)O
• InChI: InChI=1S/C15H24O3/c1-9-4-5-11(15(3,18)8-16)6-13-10(2)14(17)7-12(9)13/h9,11-12,16,18H,4-8H2,1-3H3/t9-,11+,12-,15-/m0/s1
• InChI Key: NLSBDWZKYCNOBY-LIBKGXAOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.35 g/mol
• Exact Mass: 252.17254462 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 2.07
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 3aalpha,4,5,6,7,8-Hexahydro-1,4beta-dimethyl-7beta-[(R)-1,2-dihydroxy-1-methylethyl]azulene 2(3H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9913	99.13%
Caco-2	+	0.6889	68.89%
Blood Brain Barrier	+	0.6385	63.85%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7311	73.11%
OATP2B1 inhibitior	-	0.8502	85.02%
OATP1B1 inhibitior	+	0.9090	90.90%
OATP1B3 inhibitior	+	0.9710	97.10%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5676	56.76%
BSEP inhibitior	-	0.7214	72.14%
P-glycoprotein inhibitior	-	0.8730	87.30%
P-glycoprotein substrate	-	0.7626	76.26%
CYP3A4 substrate	+	0.5350	53.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8866	88.66%
CYP3A4 inhibition	-	0.8029	80.29%
CYP2C9 inhibition	-	0.7091	70.91%
CYP2C19 inhibition	-	0.8013	80.13%
CYP2D6 inhibition	-	0.9281	92.81%
CYP1A2 inhibition	-	0.7870	78.70%
CYP2C8 inhibition	-	0.7991	79.91%
CYP inhibitory promiscuity	-	0.9379	93.79%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6536	65.36%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.5571	55.71%
Skin irritation	-	0.5152	51.52%
Skin corrosion	-	0.9513	95.13%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6713	67.13%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.8213	82.13%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.6065	60.65%
Acute Oral Toxicity (c)	III	0.6348	63.48%
Estrogen receptor binding	-	0.4877	48.77%
Androgen receptor binding	-	0.5212	52.12%
Thyroid receptor binding	+	0.5646	56.46%
Glucocorticoid receptor binding	+	0.6225	62.25%
Aromatase binding	-	0.7337	73.37%
PPAR gamma	-	0.6005	60.05%
Honey bee toxicity	-	0.9453	94.53%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9299	92.99%

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	96.22%	97.25%
CHEMBL2581	P07339	Cathepsin D	93.73%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.85%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.08%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.47%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.87%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.82%	95.56%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	83.39%	90.93%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	80.91%	86.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.62%	93.04%

Plants that contains it

• Daphne aurantiaca

Cross-Links

• PubChem: 46211177
• NPASS: NPC280256
• ChEMBL: CHEMBL1095575
• LOTUS: LTS0212391
• wikiData: Q105181534