(5aS)-2,2,4,4-Tetramethyl-5abeta-isopropyl-7-(3-methylbutanoyl)-8,10-dihydroxy-1,2,3,4,5a,10bbeta-hexahydrobenzofuro[2,3-b]benzofuran-1,3-dione

Details

• Internal ID: b1146ab3-84f4-40f2-a50c-932fa9e403ae
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Butyrophenones
• IUPAC Name: (5aR,10bR)-8,10-dihydroxy-2,2,4,4-tetramethyl-7-(3-methylbutanoyl)-5a-propan-2-yl-10bH-[1]benzofuro[2,3-b][1]benzofuran-1,3-dione
• SMILES (Canonical): CC(C)CC(=O)C1=C(C=C(C2=C1OC3(C2C4=C(O3)C(C(=O)C(C4=O)(C)C)(C)C)C(C)C)O)O
• SMILES (Isomeric): CC(C)CC(=O)C1=C(C=C(C2=C1O[C@@]3([C@H]2C4=C(O3)C(C(=O)C(C4=O)(C)C)(C)C)C(C)C)O)O
• InChI: InChI=1S/C26H32O7/c1-11(2)9-13(27)16-14(28)10-15(29)17-19-18-21(30)24(5,6)23(31)25(7,8)22(18)33-26(19,12(3)4)32-20(16)17/h10-12,19,28-29H,9H2,1-8H3/t19-,26+/m1/s1
• InChI Key: BTVCDTWMBDQZMY-BCHFMIIMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₇
• Molecular Weight: 456.50 g/mol
• Exact Mass: 456.21480336 g/mol
• Topological Polar Surface Area (TPSA): 110.00 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 4.64
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• (5aS)-2,2,4,4-Tetramethyl-5abeta-isopropyl-7-(3-methylbutanoyl)-8,10-dihydroxy-1,2,3,4,5a,10bbeta-hexahydrobenzofuro[2,3-b]benzofuran-1,3-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9788	97.88%
Caco-2	-	0.5559	55.59%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7877	78.77%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.7970	79.70%
OATP1B3 inhibitior	+	0.9376	93.76%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5529	55.29%
P-glycoprotein inhibitior	+	0.5902	59.02%
P-glycoprotein substrate	-	0.6838	68.38%
CYP3A4 substrate	+	0.5996	59.96%
CYP2C9 substrate	-	0.8021	80.21%
CYP2D6 substrate	-	0.8604	86.04%
CYP3A4 inhibition	-	0.7442	74.42%
CYP2C9 inhibition	+	0.7629	76.29%
CYP2C19 inhibition	-	0.6833	68.33%
CYP2D6 inhibition	-	0.8702	87.02%
CYP1A2 inhibition	-	0.6124	61.24%
CYP2C8 inhibition	-	0.6545	65.45%
CYP inhibitory promiscuity	+	0.7637	76.37%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9643	96.43%
Carcinogenicity (trinary)	Danger	0.5853	58.53%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.7647	76.47%
Skin irritation	-	0.6572	65.72%
Skin corrosion	-	0.9046	90.46%
Ames mutagenesis	-	0.5282	52.82%
Human Ether-a-go-go-Related Gene inhibition	-	0.6074	60.74%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.6796	67.96%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6040	60.40%
Acute Oral Toxicity (c)	I	0.4687	46.87%
Estrogen receptor binding	+	0.7786	77.86%
Androgen receptor binding	+	0.7895	78.95%
Thyroid receptor binding	+	0.6859	68.59%
Glucocorticoid receptor binding	+	0.7266	72.66%
Aromatase binding	+	0.6076	60.76%
PPAR gamma	+	0.7558	75.58%
Honey bee toxicity	-	0.8579	85.79%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9946	99.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.82%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.82%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.66%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.44%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.89%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.52%	85.14%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	91.55%	93.40%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.24%	91.24%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.96%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	86.71%	94.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.75%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	85.16%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.58%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.54%	97.25%
CHEMBL332	P03956	Matrix metalloproteinase-1	82.87%	94.50%
CHEMBL236	P41143	Delta opioid receptor	82.18%	99.35%
CHEMBL221	P23219	Cyclooxygenase-1	82.00%	90.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.45%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.43%	86.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.31%	95.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.21%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.72%	82.69%

Plants that contains it

• Acacia sparsiflora
• Achyranthes bidentata
• Agave shawii
• Ambrosia grayi
• Astrantia major
• Camellia sasanqua
• Carpinus cordata
• Cassia javanica subsp. agnes
• Convallaria keiskei
• Dirca occidentalis
• Drypetes littoralis
• Edgeworthia gardneri
• Eucalyptus regnans
• Euphorbia iberica
• Grindelia hirsutula
• Hopea jucunda
• Khaya grandifoliola
• Plumbago pulchella
• Plumeria alba
• Polygala ruwenzoriensis
• Rhodomyrtus tomentosa
• Rumex conglomeratus
• Senecio glaucus subsp. coronopifolius
• Silene vulgaris
• Syzygium jambos
• Tainia latifolia
• Thesium humile
• Tilia europaea
• Xenophyllum decorum

Cross-Links

• PubChem: 102521923
• NPASS: NPC153344
• LOTUS: LTS0050411
• wikiData: Q104945876