(1R,3aR,5S,8S,8aS)-3a-methyl-6-methylidene-1-propan-2-yl-3,4,5,7,8,8a-hexahydro-2H-azulene-1,5,8-triol

Details

• Internal ID: 4df27cd0-cff2-4a6b-982b-1b9e3cca7436
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (1R,3aR,5S,8S,8aS)-3a-methyl-6-methylidene-1-propan-2-yl-3,4,5,7,8,8a-hexahydro-2H-azulene-1,5,8-triol
• SMILES (Canonical): CC(C)C1(CCC2(C1C(CC(=C)C(C2)O)O)C)O
• SMILES (Isomeric): CC(C)[C@@]1(CC[C@]2([C@H]1[C@H](CC(=C)[C@H](C2)O)O)C)O
• InChI: InChI=1S/C15H26O3/c1-9(2)15(18)6-5-14(4)8-12(17)10(3)7-11(16)13(14)15/h9,11-13,16-18H,3,5-8H2,1-2,4H3/t11-,12-,13+,14+,15+/m0/s1
• InChI Key: BTXJIKSSLQOYHS-VQJWOFKYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₆O₃
• Molecular Weight: 254.36 g/mol
• Exact Mass: 254.18819469 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.86
• H-Bond Acceptor: 3
• 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	+	0.9875	98.75%
Caco-2	-	0.5787	57.87%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Lysosomes	0.5828	58.28%
OATP2B1 inhibitior	-	0.8475	84.75%
OATP1B1 inhibitior	+	0.9075	90.75%
OATP1B3 inhibitior	+	0.8497	84.97%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.9670	96.70%
P-glycoprotein inhibitior	-	0.9444	94.44%
P-glycoprotein substrate	-	0.7867	78.67%
CYP3A4 substrate	+	0.5158	51.58%
CYP2C9 substrate	-	0.5811	58.11%
CYP2D6 substrate	-	0.7340	73.40%
CYP3A4 inhibition	-	0.8690	86.90%
CYP2C9 inhibition	-	0.6642	66.42%
CYP2C19 inhibition	-	0.7423	74.23%
CYP2D6 inhibition	-	0.9385	93.85%
CYP1A2 inhibition	-	0.6595	65.95%
CYP2C8 inhibition	-	0.9412	94.12%
CYP inhibitory promiscuity	-	0.8383	83.83%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5821	58.21%
Eye corrosion	-	0.9841	98.41%
Eye irritation	-	0.7054	70.54%
Skin irritation	+	0.5473	54.73%
Skin corrosion	-	0.9333	93.33%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5364	53.64%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	+	0.5522	55.22%
skin sensitisation	-	0.6182	61.82%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.6555	65.55%
Acute Oral Toxicity (c)	I	0.5258	52.58%
Estrogen receptor binding	-	0.5169	51.69%
Androgen receptor binding	-	0.6086	60.86%
Thyroid receptor binding	-	0.5160	51.60%
Glucocorticoid receptor binding	-	0.5352	53.52%
Aromatase binding	+	0.6447	64.47%
PPAR gamma	-	0.7426	74.26%
Honey bee toxicity	-	0.8618	86.18%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9785	97.85%

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	96.67%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.84%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	92.68%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.23%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.41%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.45%	82.69%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.17%	85.14%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	85.53%	99.00%
CHEMBL1937	Q92769	Histone deacetylase 2	85.27%	94.75%
CHEMBL2581	P07339	Cathepsin D	85.15%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.57%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.02%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.32%	97.09%

Plants that contains it

• Ferula sinaica

Cross-Links

• PubChem: 14681670
• LOTUS: LTS0198856
• wikiData: Q104945931