(4aR)-7-hydroxy-2,2-dimethyl-4a,8-bis(3-methylbut-2-enyl)-6-(2-methylpropanoyl)chromen-5-one

Details

• Internal ID: 13c9349f-9ea1-4490-845e-332583aa2976
• Taxonomy: Organoheterocyclic compounds > Pyrans
• IUPAC Name: (4aR)-7-hydroxy-2,2-dimethyl-4a,8-bis(3-methylbut-2-enyl)-6-(2-methylpropanoyl)chromen-5-one
• SMILES (Canonical): CC(C)C(=O)C1=C(C(=C2C(C1=O)(C=CC(O2)(C)C)CC=C(C)C)CC=C(C)C)O
• SMILES (Isomeric): CC(C)C(=O)C1=C(C(=C2[C@](C1=O)(C=CC(O2)(C)C)CC=C(C)C)CC=C(C)C)O
• InChI: InChI=1S/C25H34O4/c1-15(2)9-10-18-21(27)19(20(26)17(5)6)22(28)25(12-11-16(3)4)14-13-24(7,8)29-23(18)25/h9,11,13-14,17,27H,10,12H2,1-8H3/t25-/m0/s1
• InChI Key: MJXCRNGPAMBYDU-VWLOTQADSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₄O₄
• Molecular Weight: 398.50 g/mol
• Exact Mass: 398.24570956 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.92
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9942	99.42%
Caco-2	+	0.6852	68.52%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7801	78.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8456	84.56%
OATP1B3 inhibitior	+	0.9288	92.88%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7238	72.38%
P-glycoprotein inhibitior	-	0.5818	58.18%
P-glycoprotein substrate	-	0.6917	69.17%
CYP3A4 substrate	+	0.5686	56.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8791	87.91%
CYP3A4 inhibition	-	0.8785	87.85%
CYP2C9 inhibition	-	0.7440	74.40%
CYP2C19 inhibition	-	0.8164	81.64%
CYP2D6 inhibition	-	0.9366	93.66%
CYP1A2 inhibition	-	0.8311	83.11%
CYP2C8 inhibition	-	0.8099	80.99%
CYP inhibitory promiscuity	-	0.7631	76.31%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9113	91.13%
Carcinogenicity (trinary)	Non-required	0.6572	65.72%
Eye corrosion	-	0.9805	98.05%
Eye irritation	-	0.5723	57.23%
Skin irritation	-	0.5541	55.41%
Skin corrosion	-	0.9269	92.69%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6812	68.12%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6445	64.45%
skin sensitisation	-	0.6237	62.37%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.8214	82.14%
Acute Oral Toxicity (c)	III	0.5750	57.50%
Estrogen receptor binding	+	0.8451	84.51%
Androgen receptor binding	-	0.4853	48.53%
Thyroid receptor binding	+	0.6460	64.60%
Glucocorticoid receptor binding	+	0.7486	74.86%
Aromatase binding	+	0.5733	57.33%
PPAR gamma	+	0.8451	84.51%
Honey bee toxicity	-	0.8545	85.45%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9759	97.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.09%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.33%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.00%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.57%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	91.71%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.42%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.41%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	82.47%	90.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.47%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.13%	99.23%

Plants that contains it

• Humulus lupulus
• Phlomoides rotata
• Phlomoides tuberosa

Cross-Links

• PubChem: 163190373
• LOTUS: LTS0014009
• wikiData: Q105224589