(5S,6R,8S,8aS)-6,8a-dihydroxy-5-(2-hydroxypropan-2-yl)-3,8-dimethyl-1,4,5,6,7,8-hexahydroazulen-2-one

Details

• Internal ID: c760440b-d2ed-434f-a971-995116322190
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Guaianes
• IUPAC Name: (5S,6R,8S,8aS)-6,8a-dihydroxy-5-(2-hydroxypropan-2-yl)-3,8-dimethyl-1,4,5,6,7,8-hexahydroazulen-2-one
• SMILES (Canonical): CC1CC(C(CC2=C(C(=O)CC12O)C)C(C)(C)O)O
• SMILES (Isomeric): C[C@H]1C[C@H]([C@H](CC2=C(C(=O)C[C@]12O)C)C(C)(C)O)O
• InChI: InChI=1S/C15H24O4/c1-8-5-12(16)11(14(3,4)18)6-10-9(2)13(17)7-15(8,10)19/h8,11-12,16,18-19H,5-7H2,1-4H3/t8-,11-,12+,15-/m0/s1
• InChI Key: BMNVAUVOOUYDDR-VCJARVCASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₄
• Molecular Weight: 268.35 g/mol
• Exact Mass: 268.16745924 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.18
• 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	+	0.9918	99.18%
Caco-2	+	0.6505	65.05%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6045	60.45%
OATP2B1 inhibitior	-	0.8548	85.48%
OATP1B1 inhibitior	+	0.9403	94.03%
OATP1B3 inhibitior	+	0.9159	91.59%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8052	80.52%
P-glycoprotein inhibitior	-	0.9082	90.82%
P-glycoprotein substrate	-	0.7274	72.74%
CYP3A4 substrate	+	0.5443	54.43%
CYP2C9 substrate	-	0.8086	80.86%
CYP2D6 substrate	-	0.8738	87.38%
CYP3A4 inhibition	-	0.7898	78.98%
CYP2C9 inhibition	-	0.7343	73.43%
CYP2C19 inhibition	-	0.7783	77.83%
CYP2D6 inhibition	-	0.9427	94.27%
CYP1A2 inhibition	-	0.7407	74.07%
CYP2C8 inhibition	-	0.9478	94.78%
CYP inhibitory promiscuity	-	0.8901	89.01%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5737	57.37%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.7033	70.33%
Skin irritation	+	0.5179	51.79%
Skin corrosion	-	0.9349	93.49%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6455	64.55%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.5041	50.41%
skin sensitisation	-	0.6893	68.93%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.7086	70.86%
Acute Oral Toxicity (c)	I	0.4102	41.02%
Estrogen receptor binding	-	0.6220	62.20%
Androgen receptor binding	-	0.6132	61.32%
Thyroid receptor binding	+	0.6418	64.18%
Glucocorticoid receptor binding	-	0.4718	47.18%
Aromatase binding	-	0.7371	73.71%
PPAR gamma	-	0.5525	55.25%
Honey bee toxicity	-	0.8849	88.49%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9846	98.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	93.82%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.73%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.24%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.07%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.64%	97.25%
CHEMBL1902	P62942	FK506-binding protein 1A	89.08%	97.05%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	88.24%	93.04%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.93%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	84.88%	97.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.29%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.20%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.78%	96.09%

Plants that contains it

• Daucus carota

Cross-Links

• PubChem: 45102166
• LOTUS: LTS0121281
• wikiData: Q104938463