(4R)-4,5-dihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-enyl)-3-oxocyclohexa-1,5-dien-1-olate

Details

• Internal ID: 1f21bd13-bf80-4dbe-8e13-da6115f41942
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Acyloins
• IUPAC Name: (4R)-4,5-dihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-enyl)-3-oxocyclohexa-1,5-dien-1-olate
• SMILES (Canonical): CC(C)CC(=O)C1=C(C(=C(C(C1=O)(CC=C(C)C)O)O)CC=C(C)C)[O-]
• SMILES (Isomeric): CC(C)CC(=O)C1=C(C(=C([C@@](C1=O)(CC=C(C)C)O)O)CC=C(C)C)[O-]
• InChI: InChI=1S/C21H30O5/c1-12(2)7-8-15-18(23)17(16(22)11-14(5)6)20(25)21(26,19(15)24)10-9-13(3)4/h7,9,14,23-24,26H,8,10-11H2,1-6H3/p-1/t21-/m1/s1
• InChI Key: VMSLCPKYRPDHLN-OAQYLSRUSA-M
• Popularity: 64 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₉O₅-
• Molecular Weight: 361.50 g/mol
• Exact Mass: 361.20149902 g/mol
• Topological Polar Surface Area (TPSA): 97.70 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.05
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9269	92.69%
Caco-2	+	0.5177	51.77%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7643	76.43%
OATP2B1 inhibitior	-	0.5705	57.05%
OATP1B1 inhibitior	+	0.8745	87.45%
OATP1B3 inhibitior	+	0.9359	93.59%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8448	84.48%
P-glycoprotein inhibitior	-	0.8623	86.23%
P-glycoprotein substrate	-	0.6472	64.72%
CYP3A4 substrate	+	0.5150	51.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8801	88.01%
CYP3A4 inhibition	-	0.8816	88.16%
CYP2C9 inhibition	-	0.8693	86.93%
CYP2C19 inhibition	-	0.7233	72.33%
CYP2D6 inhibition	-	0.9015	90.15%
CYP1A2 inhibition	-	0.9114	91.14%
CYP2C8 inhibition	-	0.8950	89.50%
CYP inhibitory promiscuity	-	0.9672	96.72%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6526	65.26%
Eye corrosion	-	0.9815	98.15%
Eye irritation	-	0.5769	57.69%
Skin irritation	-	0.6266	62.66%
Skin corrosion	-	0.9137	91.37%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6798	67.98%
Micronuclear	-	0.6641	66.41%
Hepatotoxicity	+	0.6929	69.29%
skin sensitisation	-	0.5780	57.80%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.7340	73.40%
Acute Oral Toxicity (c)	III	0.4092	40.92%
Estrogen receptor binding	+	0.6003	60.03%
Androgen receptor binding	+	0.5259	52.59%
Thyroid receptor binding	-	0.5495	54.95%
Glucocorticoid receptor binding	+	0.7939	79.39%
Aromatase binding	+	0.6482	64.82%
PPAR gamma	+	0.7915	79.15%
Honey bee toxicity	-	0.8550	85.50%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9775	97.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.16%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.02%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.55%	91.11%
CHEMBL301	P24941	Cyclin-dependent kinase 2	92.42%	91.23%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	86.56%	83.10%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.83%	91.24%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.41%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	84.91%	90.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.70%	89.34%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.31%	96.90%
CHEMBL3038469	P24941	CDK2/Cyclin A	82.63%	91.38%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.36%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	80.79%	94.73%

Plants that contains it

• Humulus lupulus
• Leuzea carthamoides

Cross-Links

• PubChem: 25203320
• NPASS: NPC221953