methyl (1S,4aR,5S,6R,6aR,7S,11aS,11bS)-1,5-diacetyloxy-4a,6-dihydroxy-4,4,11b-trimethyl-2,3,5,6,6a,7,11,11a-octahydro-1H-naphtho[2,1-f][1]benzofuran-7-carboxylate

Details

• Internal ID: 731ce147-9246-4269-9027-85030e31ca7e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: methyl (1S,4aR,5S,6R,6aR,7S,11aS,11bS)-1,5-diacetyloxy-4a,6-dihydroxy-4,4,11b-trimethyl-2,3,5,6,6a,7,11,11a-octahydro-1H-naphtho[2,1-f][1]benzofuran-7-carboxylate
• SMILES (Canonical): CC(=O)OC1CCC(C2(C1(C3CC4=C(C=CO4)C(C3C(C2OC(=O)C)O)C(=O)OC)C)O)(C)C
• SMILES (Isomeric): CC(=O)O[C@H]1CCC([C@]2([C@]1([C@H]3CC4=C(C=CO4)[C@H]([C@@H]3[C@H]([C@@H]2OC(=O)C)O)C(=O)OC)C)O)(C)C
• InChI: InChI=1S/C25H34O9/c1-12(26)33-17-7-9-23(3,4)25(30)21(34-13(2)27)20(28)19-15(24(17,25)5)11-16-14(8-10-32-16)18(19)22(29)31-6/h8,10,15,17-21,28,30H,7,9,11H2,1-6H3/t15-,17-,18+,19+,20+,21-,24-,25+/m0/s1
• InChI Key: NQRAYTDNIQRCFX-DKRRIRPNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₄O₉
• Molecular Weight: 478.50 g/mol
• Exact Mass: 478.22028266 g/mol
• Topological Polar Surface Area (TPSA): 133.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.12
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 3

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	-	0.5987	59.87%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7227	72.27%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.8926	89.26%
OATP1B3 inhibitior	+	0.8446	84.46%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6571	65.71%
BSEP inhibitior	+	0.7001	70.01%
P-glycoprotein inhibitior	+	0.7126	71.26%
P-glycoprotein substrate	-	0.5678	56.78%
CYP3A4 substrate	+	0.7153	71.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8141	81.41%
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	+	0.5921	59.21%
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	-	0.9084	90.84%
Skin irritation	-	0.6999	69.99%
Skin corrosion	-	0.8966	89.66%
Ames mutagenesis	-	0.6340	63.40%
Human Ether-a-go-go-Related Gene inhibition	-	0.4179	41.79%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.5052	50.52%
skin sensitisation	-	0.8755	87.55%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.4946	49.46%
Acute Oral Toxicity (c)	III	0.3661	36.61%
Estrogen receptor binding	+	0.8060	80.60%
Androgen receptor binding	+	0.7347	73.47%
Thyroid receptor binding	+	0.5246	52.46%
Glucocorticoid receptor binding	+	0.7282	72.82%
Aromatase binding	+	0.6585	65.85%
PPAR gamma	+	0.6209	62.09%
Honey bee toxicity	-	0.7648	76.48%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.26%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.17%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.86%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.70%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.39%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.83%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.48%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	86.98%	91.19%
CHEMBL2581	P07339	Cathepsin D	86.20%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.61%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.59%	86.33%
CHEMBL4208	P20618	Proteasome component C5	83.86%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.86%	97.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.61%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.37%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.82%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.75%	91.07%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.54%	89.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.20%	97.25%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.77%	100.00%

Plants that contains it

• Dendrolirium tomentosum
• Eucalyptus froggattii
• Pistacia mexicana

Cross-Links

• PubChem: 10743269
• NPASS: NPC292545
• LOTUS: LTS0219689
• wikiData: Q105184044