[(3aR,4R,5aS,6S,8R,8aS,9R,9aS)-9-acetyloxy-4,8-dihydroxy-8a-methyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-6-yl] 3-methylbutanoate

Details

• Internal ID: ea6dacd8-2d3d-4b6e-a0d8-1bb9e0ee6296
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [(3aR,4R,5aS,6S,8R,8aS,9R,9aS)-9-acetyloxy-4,8-dihydroxy-8a-methyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-6-yl] 3-methylbutanoate
• SMILES (Canonical): CC(C)CC(=O)OC1CC(C2(C1CC(C3C(C2OC(=O)C)C(=C)C(=O)O3)O)C)O
• SMILES (Isomeric): CC(C)CC(=O)O[C@H]1C[C@H]([C@@]2([C@@H]1C[C@H]([C@H]3[C@H]([C@H]2OC(=O)C)C(=C)C(=O)O3)O)C)O
• InChI: InChI=1S/C21H30O8/c1-9(2)6-16(25)28-14-8-15(24)21(5)12(14)7-13(23)18-17(10(3)20(26)29-18)19(21)27-11(4)22/h9,12-15,17-19,23-24H,3,6-8H2,1-2,4-5H3/t12-,13-,14+,15-,17-,18+,19-,21+/m1/s1
• InChI Key: KLJZYQGJDZOIRP-VHAOZWTISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₈
• Molecular Weight: 410.50 g/mol
• Exact Mass: 410.19406791 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.13
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9710	97.10%
Caco-2	-	0.6308	63.08%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5860	58.60%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8521	85.21%
OATP1B3 inhibitior	+	0.8925	89.25%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9179	91.79%
P-glycoprotein inhibitior	-	0.5372	53.72%
P-glycoprotein substrate	-	0.5180	51.80%
CYP3A4 substrate	+	0.6644	66.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8873	88.73%
CYP3A4 inhibition	+	0.5525	55.25%
CYP2C9 inhibition	-	0.6844	68.44%
CYP2C19 inhibition	-	0.6772	67.72%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.6464	64.64%
CYP2C8 inhibition	-	0.7631	76.31%
CYP inhibitory promiscuity	-	0.9019	90.19%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5602	56.02%
Eye corrosion	-	0.9839	98.39%
Eye irritation	-	0.8813	88.13%
Skin irritation	+	0.4894	48.94%
Skin corrosion	-	0.9288	92.88%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5228	52.28%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.6212	62.12%
skin sensitisation	-	0.7447	74.47%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.8000	80.00%
Acute Oral Toxicity (c)	I	0.3693	36.93%
Estrogen receptor binding	+	0.7602	76.02%
Androgen receptor binding	+	0.5714	57.14%
Thyroid receptor binding	+	0.5487	54.87%
Glucocorticoid receptor binding	+	0.6154	61.54%
Aromatase binding	+	0.5979	59.79%
PPAR gamma	-	0.5649	56.49%
Honey bee toxicity	-	0.6539	65.39%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9939	99.39%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.90%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.39%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.99%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	96.96%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.08%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	93.39%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.51%	95.50%
CHEMBL2581	P07339	Cathepsin D	89.44%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.99%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.99%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.86%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.37%	97.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.02%	91.07%
CHEMBL340	P08684	Cytochrome P450 3A4	84.66%	91.19%
CHEMBL299	P17252	Protein kinase C alpha	82.99%	98.03%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.73%	95.71%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.33%	89.50%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.17%	97.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.38%	95.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.77%	96.47%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.39%	82.50%

Plants that contains it

• Gaillardia pulchella

Cross-Links

• PubChem: 163040383
• LOTUS: LTS0049723
• wikiData: Q103787155