methyl (4aR,5S,6R,6aR,7S,11aS,11bR)-5-acetyloxy-4a,6-dihydroxy-4,4,11b-trimethyl-1-oxo-2,3,5,6,6a,7,11,11a-octahydronaphtho[2,1-f][1]benzofuran-7-carboxylate

Details

• Internal ID: 803abd41-a9ec-44de-901d-3a703848ea32
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: methyl (4aR,5S,6R,6aR,7S,11aS,11bR)-5-acetyloxy-4a,6-dihydroxy-4,4,11b-trimethyl-1-oxo-2,3,5,6,6a,7,11,11a-octahydronaphtho[2,1-f][1]benzofuran-7-carboxylate
• SMILES (Canonical): CC(=O)OC1C(C2C(CC3=C(C2C(=O)OC)C=CO3)C4(C1(C(CCC4=O)(C)C)O)C)O
• SMILES (Isomeric): CC(=O)O[C@H]1[C@@H]([C@@H]2[C@H](CC3=C([C@H]2C(=O)OC)C=CO3)[C@@]4([C@@]1(C(CCC4=O)(C)C)O)C)O
• InChI: InChI=1S/C23H30O8/c1-11(24)31-19-18(26)17-13(10-14-12(7-9-30-14)16(17)20(27)29-5)22(4)15(25)6-8-21(2,3)23(19,22)28/h7,9,13,16-19,26,28H,6,8,10H2,1-5H3/t13-,16+,17+,18+,19-,22-,23+/m0/s1
• InChI Key: IRQDLEBBCDCFMG-SVBHYKRNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₀O₈
• Molecular Weight: 434.50 g/mol
• Exact Mass: 434.19406791 g/mol
• Topological Polar Surface Area (TPSA): 123.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.76
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9429	94.29%
Caco-2	-	0.5599	55.99%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7227	72.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8933	89.33%
OATP1B3 inhibitior	+	0.8446	84.46%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6571	65.71%
BSEP inhibitior	-	0.4756	47.56%
P-glycoprotein inhibitior	+	0.5796	57.96%
P-glycoprotein substrate	-	0.6179	61.79%
CYP3A4 substrate	+	0.7139	71.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8169	81.69%
CYP3A4 inhibition	-	0.6274	62.74%
CYP2C9 inhibition	-	0.6722	67.22%
CYP2C19 inhibition	-	0.8041	80.41%
CYP2D6 inhibition	-	0.9217	92.17%
CYP1A2 inhibition	+	0.5305	53.05%
CYP2C8 inhibition	+	0.4920	49.20%
CYP inhibitory promiscuity	-	0.8715	87.15%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6015	60.15%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9161	91.61%
Skin irritation	-	0.6999	69.99%
Skin corrosion	-	0.8966	89.66%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6501	65.01%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8755	87.55%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5908	59.08%
Acute Oral Toxicity (c)	III	0.3661	36.61%
Estrogen receptor binding	+	0.6735	67.35%
Androgen receptor binding	+	0.7336	73.36%
Thyroid receptor binding	+	0.5873	58.73%
Glucocorticoid receptor binding	+	0.7202	72.02%
Aromatase binding	+	0.6041	60.41%
PPAR gamma	+	0.5617	56.17%
Honey bee toxicity	-	0.7591	75.91%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9774	97.74%

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	99.12%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.80%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.72%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.12%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.50%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.48%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.42%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.70%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.65%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.20%	94.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.70%	97.25%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.66%	92.62%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.76%	91.07%
CHEMBL4208	P20618	Proteasome component C5	84.12%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.33%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.21%	100.00%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	80.73%	96.39%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.65%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.51%	89.00%

Plants that contains it

• Dendrolirium tomentosum
• Eucalyptus froggattii
• Pistacia mexicana

Cross-Links

• PubChem: 10622703
• NPASS: NPC193230
• LOTUS: LTS0275373
• wikiData: Q105119026