(4R)-4-[(1R,2R)-1-(1,3-benzodioxol-5-yl)-1-hydroxypropan-2-yl]-4,5-dimethoxy-2-prop-2-enylcyclohexa-2,5-dien-1-one

Details

• Internal ID: abedc7fd-a628-4ee9-92b4-0706c8a49d34
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Bicyclic monoterpenoids
• IUPAC Name: (4R)-4-[(1R,2R)-1-(1,3-benzodioxol-5-yl)-1-hydroxypropan-2-yl]-4,5-dimethoxy-2-prop-2-enylcyclohexa-2,5-dien-1-one
• SMILES (Canonical): CC(C(C1=CC2=C(C=C1)OCO2)O)C3(C=C(C(=O)C=C3OC)CC=C)OC
• SMILES (Isomeric): C[C@H]([C@H](C1=CC2=C(C=C1)OCO2)O)[C@@]3(C=C(C(=O)C=C3OC)CC=C)OC
• InChI: InChI=1S/C21H24O6/c1-5-6-15-11-21(25-4,19(24-3)10-16(15)22)13(2)20(23)14-7-8-17-18(9-14)27-12-26-17/h5,7-11,13,20,23H,1,6,12H2,2-4H3/t13-,20-,21-/m1/s1
• InChI Key: YZPIXMCJIWJICJ-OBVPDXSSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₆
• Molecular Weight: 372.40 g/mol
• Exact Mass: 372.15728848 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.09
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9889	98.89%
Caco-2	+	0.6099	60.99%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7287	72.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8928	89.28%
OATP1B3 inhibitior	+	0.8938	89.38%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.6851	68.51%
P-glycoprotein inhibitior	+	0.7129	71.29%
P-glycoprotein substrate	-	0.7047	70.47%
CYP3A4 substrate	+	0.5498	54.98%
CYP2C9 substrate	-	0.8022	80.22%
CYP2D6 substrate	-	0.8427	84.27%
CYP3A4 inhibition	+	0.9239	92.39%
CYP2C9 inhibition	+	0.6906	69.06%
CYP2C19 inhibition	+	0.8539	85.39%
CYP2D6 inhibition	-	0.7114	71.14%
CYP1A2 inhibition	-	0.6086	60.86%
CYP2C8 inhibition	-	0.8063	80.63%
CYP inhibitory promiscuity	+	0.8591	85.91%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4811	48.11%
Eye corrosion	-	0.9847	98.47%
Eye irritation	-	0.9428	94.28%
Skin irritation	-	0.7209	72.09%
Skin corrosion	-	0.9472	94.72%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4401	44.01%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	+	0.5534	55.34%
skin sensitisation	-	0.5647	56.47%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.4755	47.55%
Acute Oral Toxicity (c)	III	0.4425	44.25%
Estrogen receptor binding	+	0.8001	80.01%
Androgen receptor binding	+	0.7391	73.91%
Thyroid receptor binding	+	0.6463	64.63%
Glucocorticoid receptor binding	+	0.7959	79.59%
Aromatase binding	+	0.6640	66.40%
PPAR gamma	-	0.5473	54.73%
Honey bee toxicity	-	0.7276	72.76%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9862	98.62%

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	99.68%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	99.42%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.27%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.45%	94.45%
CHEMBL2581	P07339	Cathepsin D	98.39%	98.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	97.41%	94.80%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.51%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.35%	95.56%
CHEMBL240	Q12809	HERG	92.85%	89.76%
CHEMBL2039	P27338	Monoamine oxidase B	90.78%	92.51%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.61%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.65%	92.62%
CHEMBL4208	P20618	Proteasome component C5	89.42%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.12%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.55%	95.89%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	84.39%	85.30%
CHEMBL3401	O75469	Pregnane X receptor	83.04%	94.73%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.17%	100.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	81.60%	80.96%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.59%	90.71%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.67%	93.40%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.54%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.40%	91.07%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.32%	90.24%

Plants that contains it

• Piper wightii

Cross-Links

• PubChem: 162909009
• LOTUS: LTS0201046
• wikiData: Q105369386